LipidBank - Carotenoid

No	Structure	COMMON NAME	NAME	DATA No	INFORMANT	SYMBOL	FORMULA	MOL.WT(ave)	Download	BIOOGICAL ACTIVITY	PHYSICAL AND CHEMICAL PROPERTIES						SPECTRAL DATA					CHROMATOGRAM DATA	SOURCE	CHEMICAL SYNTHESIS	METABOLISM	GENETIC INFORMATION	NOTE	REFERENCES
No	Structure	COMMON NAME	NAME	DATA No	INFORMANT	SYMBOL	FORMULA	MOL.WT(ave)	Download	BIOOGICAL ACTIVITY	MELTING POINT	BOILING POINT	DENSITY	REFRACTIVE INDEX	OPTICAL ROTATION	SOLUBILITY	UV SPECTRA	IR SPECTRA	NMR SPECTRA	MASS SPECTRA	OTHER SPECTRA	CHROMATOGRAM DATA	SOURCE	CHEMICAL SYNTHESIS	METABOLISM	GENETIC INFORMATION	NOTE	REFERENCES
1		b-Carotene/ b,b-Carotene	b,b-Carotene	VCA0001	Masayoshi Ito	BC	C₄₀H₅₆	536.873		Spinach D1-D2-cyt b559 complex contains 2 b-carotene, 6 chlorophyll a and 2 pheophytin a (Ref. 1137). Crystal structure of photosystem II from Thermosynechococcus vulcanus (cyanobacterium) contains 2 b-carotene and 36 chlorophyll a (Ref. 1289), and that from Thermosynechococcus elongatus contains 7 b-carotene and 36 chlorophyll a (Ref. 1290) and 9 b-carotene, 36 chlorophyll a and 2 pheophytin a (Ref. 1336). Crystal structure of photosystem I from Thermosynechococcus elongatus (cyanobacterium) contains 22 b-carotene and 96 chlorophyll a (Ref. 1288). Purified cytochrome b₆f complex from spinach contains 0.77 mol b-carotene and 0.97 mol chlorophyll a, Mastigocladau laminosus (cyanobacterium) 1.02 and 1.65, and Chlamydomonas reinhardtii (green alga) 0.55 and 1.37, respectively. (Ref. 1099) Crystal structure of dimeric cytochrome b₆f complex from M.laminosus (Ref. 1294) and C.reinhardtii (Ref. 1292) contain 2 mol b-carotene and 2 mol chlorophyll a. Fucoxanthin-chlorophyll a/c-protein assembly (FCPA) with energy transfer activity from fucoxanthin to chlorophyll a and from chlorophyll c to chlorophyll a isolated from Dictyota dichotoma (brown alga); 10 fucoxanthin, 1 violaxanthin, no b-carotene, 3 chlorophyll c, 13 chlorophyll a and a 54 kDa protein to form a 4.8 S complex (Ref. 1115). Pro-vitamin A(Ref. 0102/0216). Singlet oxygen-quenching activity (Ref. 0088/0230/0438/0441). Antioxidant activity (Ref. 0090/0091/0092/0093/0103/0214/0226/0437). Anti-tumor activity (Ref. 0099/0100/0101/0217/0229). Effects raising the incidence of lung cancer in smokers (Ref. 1006). Both lycopene and b-carotene showed no inhibitory effect on the development of rat urinary bladder carcinomas, while combination of carotenoids with NSAID decreased numbers and incidences of cancers (Ref. 1211). Palm carotene and b-carotene inhibited pancreatic carcinogenesis in hamsters, but a-carotene showed no effects (Ref. 1212). A cellular carotenoid-binding protein of 67 kDa from ferret (mammalian) liver is purified and characterized with a high degree of specificity for binding only carotenoids with at least one unsubstituted b-end group (Ref. 1160).	180-182C (Ref. 0023) 177-180C (Ref. 0024)						lmax (nm): hexane 425, 450, 478 [Spectrum 0001] (Ref. 0060/0063); methanol 341, 429 (shoulder), 449, 475, %III/II=24.6 [Spectrum 1101] (Ref. 1052); acetonitrile/methanol/THF (58:35:7) 278, 353, 429 (shoulder), 453, 479, %III/II=26 [Spectrum 1001] (Ref. 1057); hexane, chloroform and CS₂ [Spectrum 1052]	nmax(KBr)/cm^-¹: 1629 and 1599w (C=C) and 965s (CH) [Spectrum 0002] (Ref. 0065)	¹H-NMR d(270 MHz, CDCl3): 6.16 (7, 7'-H), 6.15 (8, 8'-H), 6.15 (10, 10'-H), 6.65 (11, 11'-H), 6.35 (12, 12'-H), ca. 6.25 (14, 14'-H), ca. 6.63 (15, 15'-H), 1.028 (1, 1'-gem-Me), 1.719 (5, 5'-Me), 1.972 (9, 9', 13, 13'-Me) (Ref. 0062/0066) ¹³C-NMR d(CDCl3): 34.3 (1, 1'), 39.7 (2, 2'), 19.3 (3, 3'), 33.2 (4, 4'), 129.3 (5, 5'), 138.0 (6, 6'), 126.7 (7, 7'), 137.8 (8, 8'), 136.0 (9, 9'), 130.8 (10, 10'), 125.0 (11, 11'), 137.3 (12, 12'), 136.4 (13, 13'), 132.4 (14, 14'), 130.0 (15, 15'), 29.0 (1, 1'-gem-Me), 21.7 (5, 5'-Me), 12.7 (9, 9'-Me), 12.7 (13, 13'-Me) (Ref. 0061).	m/z: 536 (M, 100%), 444 (M-92, 10%), 430 (M-106, 0.6%) (Ref. 0058/0060) (70 eV) m/z (ion, intensity relative to base peak in %): 536 (M, 45), 444 (16), 430 (4), 219 (13),197 (12), 157 (26), 145 (34), 133 (32), 119 (72), 105 (62), 95 (51), 91 (45), 81 (48), 69 (100), 55 (60), 41 (48) (Ref. 0066) FD-MS m/z: 536 (100%) (Ref. 1053)		RF-TLC on 0.25 mm RP-18 layers (Merck, Art. 15423) using several ratio of light petroleum (bp 40-60C)-acetonitrile-methanol ex: 1:6:3 Rf=0.09, 3:1:6 Rf=0.20 (Ref. 0135) HPLC (column: calcium hydroxide (Nakarai) 0.430 cm, eluent: acetone-hexane 99.9:0.1, flow: 0.5 ml/min) tR = ca. 28 min (all-E isomer) [Chromatogram 0001] (Ref. 0062) HPLC (column: Spherisorb A5Y (alumina) 0.2825 cm, eluent: hexane with controlled water content) tR = ca. 32 min (all-E isomer) [Chromatogram 0002] (Ref. 0066) HPLC (column: Vydac 218TP54, acetonitrile-methanol-tetrahydrofuran 40:56:4, flow: 1 ml/min) tR = ca. 11 min (all-E isomer) [Chromatogram 0003] (Ref. 0067) HPLC (columun: TSK gel ODS-80Ts (Tosoh) 0.4615 cm, eluent and flow: 1.0 ml/min, H2O-MeOH 5:95 for 5 min, follwed by 5 min-linear gradient MeOH-THF 7:3, and then MeOH-THF 7:3 for 5 min) b-carotene, echinenone, b-cryptoxanthin, 3-hydroxy-echinenone, cantaxanthin, 3'-hydroxy-echinenone, cis-adonixanthin, adonirubin, adonixanthin and astaxanthin were separated. tR = 14.98 min for b-carotene (Ref. 0208) A reversed-phase HPLC procedure for quantitative measurement in serum of seven carotenoids (lutein, zeaxanthin, canthaxanthin, b-cryptoxanthin, lycopenes, a-c arotene and b-carotene) has been developed. (Ref. 0227) Retinol, a-tocoherol, lutein, all-trans-lycopene, and a- and b-carotenes were determined in human plasma by reversed-phase HPLC. (Ref. 0228) HPLC (column; Novapak C18 (Waters) 8 X 100 mm: eluelnt; acetonitrile/methanol/THF 58:35:7: flow 2.0 ml/min) Rt=19.5 min (Ref. 1057)	Bacteria, algae, higher plants (Ref. 0409) Animals (Ref. 0410) Bangia fucopurupurea, Nemalion helminthoides, Bonnemaisonia hamifera, Gigartina stellata, Rhodymenia palmata, Ceramium rubrum, Polysiphonia brodiaei, Polysiphonia urceolata (Red algae) (Ref. 0058) Anacystis nidulans (Cyanobacterium) (Ref. 1077) Chloroflexus aurantiacus (Ref. 1105) and Chloroflexus aggregans (S. Takaichi) (Ref. 1106) (green filamentous bacteria)	The Wittig olefination of the C10-dialdehyde with 2 equivalents of the C15-phosphonium salt and of the retinlylphosphonium salt with retinal is described. b-Carotene is obtained in 80-85% yield after thermal isomerisation. (Ref. 0020) Retinyl phosphonate was condensed with retinal to afford b-carotene in good yield. (Ref. 0021) The di-Grignard reagent of acetylene was reacted with 2 equivalents of the C19-aldehyde to give the C40-acetylenic diol, from which b-carotene was obtained by dehydration, Lindlar hydrogenation, and isomerisation. (Ref. 0015/0020/0022) The reductive coupling of retinal on treatment with low-valent titanium species, formed in situ TiCl3 and LiAlH4, provided b-carotene in high yield. (Ref. 0015/0023) The reductive coupling of retinal to give b-carotene is also possible with TiCl4 and LiAlH4 in the presence of 1,8-bis(dimethylamino)naphthalene as a proton sponge. (Ref. 0015/0024) 2 Equivalents of the C15-sulphone was coupled with the C10-dialdehyde using BuLi as a base, acetylated in situ, and treated with aqueous NaOH to provide all-E-11,11'-bis[(p-chlorophenyl)-sulphonyl]-b,b-carotene in high yield. Subsequent elimination of the sulphonyl group then gave all-E-b-carotene. (Ref. 0014/0017/0026) 2 Equivalents of the C13-sulphone was reacted with the C14-acetylenic dichloride to give 15,15'-didehydro-b-carotene, which was transformed by a twofold isomerisation and partial reduction to b-carotene. (Ref. 0014/0017/0026) Crystalline all-trans-b-carotene was obtained in 65% yield by simply refluxing a mixture of 2.6 equivalents of b-ionylideneethanol (C15-alcohol), phenyl isocyanate and tributylphosphine, 1 equivalent of the C10-dialdehyde, and 10 mol% of Pd(PPh3)4 in CH3CN for 5 h. (Ref. 0015/0025)	b-Carotene is synthesized from lycopene through two-step cyclization reactions by way of g-carotene by carotenogenic organisms such as higher plants (CrtL-b), algae, cyanobacteria (CrtL), and bacteria Erwinia species (CrtY) (Ref. 1002/1003/1004/1005). [Table 1025] b-Carotene is metabolized to retinal by b,b-carotene-15,15'-dioxygenase in animals. The gene encoding this enzyme has been cloned and functionally identified from chicken (Ref. 1044), Drosophila melanogaster (fly) (Ref. 1122), mouse (Ref. 1123/1233) and human (Ref. 1231). b,b-Carotene-9',10'-dioxygenase is functionally identified from mouse, and its homolog is found from human and zebrafish (Ref. 1185). b-Carotene is cleaved to crocetindial and b-cyclocitral by b-carotene 7,8(7',8') oxygenase of Microcystis (cyanobacterium) by freezing the cell pellet. The enzyme requires O₂ and iron, but is sensitive to sulfhydryl reagents, antioxidants and chelation reagents, and is membrane bound (Ref. 1266).	Genes required for the biosynthesis of b-carotene from farnesyl diphosphate (FPP) were clarified in epiphytic bacteria Erwinia species for the first time in the beginning of the 1990's (Ref. 0201/1001). b-Carotene is synthesized from FPP by four crt gene products, CrtE, CrtB, CrtI, and CrtY (Ref. 1002). [Table 0001] Nowadays, many corresponding genes are isolated from various organisms such as higher plants, cyanobacteria, fungi, and yeasts as well as bacteria, and the functions of the genes are elucidated (Ref. 0202/0233/1002/1003/1004/1005). Lycopene is the direct substrate for the synthesis of b-carotene by the way of g-carotene, catalyzed by lycopene cyclase (CrtY, LCY) (Ref. 0232/0234/1018). Lycopene cyclases are divided into three types (Ref. 1258). (1) CrtY and CrtL type: Higher plants (Lcy-b, CrtL-b), cyanobacteria (CrtL), purple bacteria, and bacteria including Erwinia and Paracoccus species (CrtY) (Ref. 1002/1003/1004/1005). They and also lycopene e-cyclase (CrtL-e, plants), lycopene b-monocyclase (CrtLm and CrtYm, bacteria) and capsanthin-caprorubin synthase (CCS, plants) have homology and five conserved regions (Ref. 1258). Erwinia CrtY has NADPH binding domain, but hydrogen atom introduced at C-2 comes from water not from NADPH (Ref. 1313). (2) CrtYc and CrtYd type: They are divided into three groups, and they among threegroups have homology (Ref. 1310/1311). A heterodimer of two peptides (CrtYc and CrtYd) is found in Brevibacterium linens (Ref. 1124) and Mycobacterium aurum A+ (Ref. 1127) (Actinomycetales). A fusion-type of CrtYc and CrtYd is found in Halobacterim salinarum (CrtY) (Ref. 1310) and Sulfolobus solfataricus (Ref. 1311) (archaeon). A bifunctional enzyme involved lycopene cyclase activity (CrtY) located in N-terminus domain and phytoene synthase activity (CrtB) located in C-terminus domain is found Xanthophyllomyces dendrorhous (crtYB) (Ref. 1172), Mucor circinelloides (carRP) (Ref. 1173), Phycomyces blakesleeanus (carRA) (Ref. 1174), Neurospora crassa (al-2) (Ref. 1176), and Blakeslea trispora (CarRA) (Ref. 1312) (fungus). CrtY region is also a fusion of CrtYc and CrtYd. (3) CruA type: Recently, a new type CruA is found in Chlorobium tepidum (green sulfur bacteria). From sequence homology, this is also found in some cyanobacteria.	Biotechnological achievement has recently been made for purposes of supplying b-carotene (provitamin A) to vitamin A-deficient children, by a Swiss and German group, i. e., transgenic rice plants 'Golden rice', which accumulate b-carotene in the endosperm, have been constructed by using the plant- and Erwinia-derived carotenogenic genes (Ref. 1017). Transgenic tomato plants, in which the b-carotene content has increased about threefold to 45% of the total carotenoid content, have also been constructed using the Erwinia crtI gene by an English, German, and Japanese group (Ref. 1066). Gel filtration of carrot root chromoplasts yields one major carotenoprotein, in which one unit contains one a-carotene and two b-carotene in 54-kDa peptide (Ref. 1272). Semi-empirical molecular orbital calculations using AM1 Hamiltonian (MNDO-AM1 method) were performed in order to predict their stable structures (Ref. 1337)	[0014] / [0015] / [0017] / [0020] / [0021] / [0022] / [0023] / [0024] / [0025] / [0026] / [0058] / [0060] / [0061] / [0062] / [0063] / [0065] / [0066] / [0067] / [0088] / [0090] / [0091] / [0092] / [0093] / [0099] / [0100] / [0101] / [0102] / [0103] / [0135] / [0201] / [0202] / [0208] / [0214] / [0216] / [0217] / [0226] / [0227] / [0228] / [0229] / [0230] / [0232] / [0233] / [0234] / [0409] / [0410] / [0437] / [0438] / [0441] / [1001] / [1002] / [1003] / [1004] / [1005] / [1006] / [1017] / [1018] / [1044] / [1052] / [1053] / [1057] / [1066] / [1077] / [1099] / [1105] / [1106] / [1115] / [1122] / [1123] / [1124] / [1127] / [1137] / [1160] / [1172] / [1173] / [1174] / [1176] / [1185] / [1211] / [1212] / [1231] / [1233] / [1258] / [1266] / [1272] / [1288] / [1289] / [1290] / [1292] / [1294] / [1310] / [1311] / [1312] / [1313] / [1336] / [1337]
2		Astaxanthin/ (3S,3'S)-Astaxanthin	(3S,3'S)-3,3'-Dihydroxy-b,b-carotene-4,4'-dione	VCA0002	Masayoshi Ito		C₄₀H₅₂O₄	596.838		Antioxidant activity (Ref. 0092/0093/0215). Singlet oxygen quenching activity (Ref. 0088/0230/0441). Immunomodulating action (Ref. 0213). Chemoprevention of carcinogenesis (Ref. 0218/0219). Astaxanthin in cyst cells of Haematococcus pluvialis (green alga) functions as an antioxidant agent against oxidative stress (singlet oxygen, superoxide anion radical, hydrogen peroxide and peroxy radical) (Ref. 1140). Astaxanthin inhibited liver tumorigenesis in mouse (Ref. 1207). a-Crustacyanin from Homarus gammarus (lobster) shell consists of five kinds of peptides; CRTC (A1, C1 and C2 peptides) and CRTA (A2 and A3 peptides) (Ref. 1273). b-Crustacyanin is a heterodimer of one CRTA and one CRTC, and two molecules of astaxanthin are located between two peptides. a-Crustacyanin is octamer of b-crustacyanin (totally 16 peptides and 16 astaxanthin), and has a molecular weight of about 320 kDa. Absorption maximum of astaxanthin in organic solvent is ca. 480 nm, that of b-crustacyanin is ca. 580 nm, and that of a-crustacyanin is ca. 630 nm. Keto group is essential to bind peptide and spectral shift (Ref. 1275/1276). 3D-Structure of b-crustacyanin (A1 and A2 dimer) is investigated (Ref. 1274).	216-218C (Ref. 0010)						lmax (nm) (e): CHCl3 225 (15000), 251 (14500), 285sh (14000), 298 (15000), 324 (14500), 488 (125000) (Ref. 0010/0077/0080); methanol [Spectrum 1102]	nmax(KBr)/cm^-¹: 3486m (OH), 1664s (conj. CO), 1607m, 1557s (C=C), 1399w, 1390m, 1366w (gem. Dimetyl), 1076s, 1039m (OH) and 969s (CH=CH, trans) [Spectrum 0003] (Ref. 0010/0077)	¹H-NMR d(500 MHz, CDCl3): 1.21 and 1.32 (each 6H, s, 1, 1'-gem-Me), 1.81 (2H, t, J 13, 2, 2'-Hax), 1.94 (6H, s, 5, 5'-Me), 1.98 and 2.00 (each 6H, s, 9, 9', 13, 13'-Me), 2.16 (2H, dd, J 6 and 13, 2, 2'-Heq), 3.67 (2H, d, J 2, 3, 3'-OH), 4.32 (2H, ddd, J 2, 6 and13, 3, 3'-H) and 6.20-6.70 (14H, m, olefinic-H) (Ref. 0068/0077/0202)	m/z: 596 (M), (M-16), (M-16-16), (M-79), (M-92), (M-106), (M-92-16), (M-106-16), (M-154), (M-167), (M-207), (M-219), (M-233) (Ref. 0058/0059/0077)	CD data in CH2Cl2 solution: De 224 (+12.8), 249 (-14.4), 280 (+12.5), 323 (-23.1), 384 (+6.7), 521 (-3.2) [Spectrum 0004] (Ref. 0064/0068/0078/0080) CD data in EPA solution (25C): De 240 (-20.0), 252 (0), 270 (+20.0), 284 (0), 314 (-34.0), 355 (0), 372 (+3.0) (Ref. 0421)	TLC (Kieselgel 60 Merck, CH2Cl2-acetone-formic acid 95:5:3) Rf = 0.3 (Ref. 0010) HPLC (column: Sumipax OA-2000 (10mm) 0.425 cm, eluent: hexane-CH2Cl2-EtOH 48:16:0.6, flow: 0.8 ml/min) tR = ca. 57 min (3R,3'R), ca. 60 min (meso), ca. 64 min (3S,3'S) [Chromatogram 0004] (Ref. 0032/0069/0070/0210) HPLC (column: LiChrosorb SI 60 (5 mm) 0.3250 cm, eluent: hexane-ethyl acetate-acetonitrile 88:10:2, flow: 0.8 ml/min) tR = ca. 42 min (diacetate of all-E isomer) [Chromatogram 0005] (Ref. 0071) HPLC (columun: TSK gel ODS-80Ts (Tosoh) 0.4615 cm, eluent and flow: 1.0 ml/min, H₂O-MeOH 5:95 for 5 min, follwed by 5 min-linear gradient MeOH-THF 7:3, and then MeOH-THF 7:3 for 5 min) b-carotene, echinenone, b-cryptoxanthin, 3-hydroxy-echinenone, cantaxanthin, 3'-hydroxy-echinenone, cis-adonixanthin, adonirubin, adonixanthin and astaxanthin were separated. tR = 6.30 min for astaxanthin (Ref. 0208). Separation of (3S,3'S), (3S,3'R) and (3R,3'R) astaxanthin by HPLC on a Pirkle covalent L-leucine column (Ref. 1164).	Homarus gammarus (lobster) (Ref. 0418) Salmo salar, Oncorhynchus (salmon) (Ref. 0419) Asterias rubens (starfish) (Ref. 0420) Shrimps and lobsters (Ref. 0421) Euphausia superba (antarctic krill) (Ref. 0422/0431/1256) Asterina pectinifera, Asterias amurensis (tarfish) (Ref. 0423) Watasenia scintilans, Sepia modokai, Sepia officinales (cuttlefish) (Ref. 0424) Octopus vulgaris, Octopus ocellatus, Octopus minor (octopus) (Ref. 0424) Adonis aestivalis (flower petals of higher plant) (Ref. 0433) Haematococcus pluvialis (green alga) (Ref. 1007) Agrobacterium aurantiacum, Alcaligenes sp. strain PC-1 (marine bacteria; present name Paracoccus sp. N81106 and MBIC03024, respectively) (Ref. 0068/0085) It has recently been shown that these marine bacteria belong to Paracoccus species according to their16S rDNA analysis, performed by T. Hamada of Marine Biotechnology Institute (DDBJ accession number: AB008114). Paracoccus marcusii (gram-negative bacterium, a-3 subclass of the Proteobacteria) (Ref. 1012)	The Wittig condensation of C10-dialdehyde with 2 equiv. of C15-phosphonium salt and subsequent thermal isomerization afforded astaxanthin. Racemic astaxanthin --- C15-phosphonium salt was prepared starting from 6-oxo-isophorone. (Ref. 0011) (3S,3'S)-Astaxanthin --- C15-phosphonium salt was prepared starting from (4R,6R)-4-hydroxy-2,2,6-trimethylcyclohexanone. (Ref. 0010/0016) (3S,3'S)- and (3R,3'R)-Astaxanthin --- Enantiomeric chiral blocks of C15-phosphonium salts were synthesized via three different routes. (Ref. 0012/0016) (3S,3'S)- and (3R,3'R)-Astaxanthin --- C15-Phosphonium salts were prepared from enantiomeric 3-acetoxy-4-oxo-b-ionones obtained by separation of the corresponding diastereomeric camphanates and by microbial resolution. (Ref. 0015/0073) (3S,3'S)-7,8-Didehydro- and 7,8,7',8'-tetradehydro-astaxanthins were synthesized starting from (4'S)-(2E)-5-(4'-hydroxy-2',6',6'-trimethyl-3'-oxo-1'-cyclohexenyl)-3-methyl-2-penten-4-ynal. (Ref. 0016/0143) The Wittig reaction between 2 equiv. of the phenoxyacetylated (S)-C15-phosphonium bromide and C10-dialdehyde or C10-acetylenic dialdehyde gave (3S,3'S)-astaxanthin or (3S,3'S)-15,15'-didehydroastaxanthin. (3S,3'S)-15,15'-Didehydroastaxanthin was transformed into (3S,3'S)-astaxanthin by partial reduction and subsequent isomerization. (Ref. 0143)	Rainbow trout and salmon: astaxanthin idoxanthin adonixanthin zeaxanthin zeaxanthin 5,6-epoxides (Ref. 0406/0407) Marine fish egg (Prognichthys aggo, Seriola quinqueradiata):astaxanthin idoxanthin b,b-carotene-3,4,3'-triol zeaxanthin 3-hydroxy-b,e-caroten-3'-one e,e-carotene-3,3'-dione 3-hydroxy-e,e-caroten-3'-dione tunaxanthin (Ref. 0408) Yellowtail (Seriola quinqueradiata): astaxanthin b-carotene-triol zeaxanthin 3'-epilutein tunaxanthin (Ref. 0430/0435) astaxanthin 3-dehydroretinal retinal (Ref. 0216) Red sea bream (Pagrus major): astaxanthin b-carotene-triol zeaxanthin 3'-epilutein tunaxanthin (Ref. 0432) astaxanthin idoxanthin 4-ketozeaxanthin (Ref. 0436) Tilapia (Tilapia nilotica): astaxanthin zeaxanthin 3,4-didehydroretinol (Ref. 0417/0216) Astaxanthin yield in various culture conditions of Haematococcus pluvialis (Chlorophyceae) (Ref. 1145) Astaxanthin and canthaxanthin are accumulated in lipoidal globules of Scenedesmus komarekii (Chlorophyceae, Chlorophyta) cultured under high light intensity and nitrogen limitaion (Ref. 1147).	Genes required for the biosynthesis of astaxanthin from b-carotene were isolated from the marine bacteria, Agrobacterium aurantiacum and Alcaligenes sp. strain PC-1 (present name: Paracoccus sp. N81106 and MBIC03024, respectively) (Ref. 0202/1008), and the functions of the genes were determined (Ref. 0202/0205/1009). b-Carotene is converted to astaxanthin by two dioxygenase enzymes CrtW (ketolase) and CrtZ (hydroxylase), which require O₂, Fe²⁺, and 2-oxoglutarate (Ref. 1002). [Table 0002] The corresponding genes were also isolated from the green alga Haematococcus pluvialis (Ref. 0203/1010/1011).	Almost the same stereochemical composition in astaxanthin, its monoester and its diester in krill are found: 62-71% (3R,3'R)-, 11-14% (3R,3'S; meso)- and 17-26% (3S,3'S)-astaxanthin (Ref. 0422). Those in Euphausia, Thysanoessa, Calanus, Acanthephyra and Cancer (Crustaceans) are also reported (Ref. 1257). Semi-empirical molecular orbital calculations using AM1 Hamiltonian (MNDO-AM1 method) were performed in order to predict their stable structures (Ref. 1337).	[0010] / [0011] / [0012] / [0015] / [0016] / [0032] / [0058] / [0059] / [0064] / [0068] / [0069] / [0070] / [0071] / [0073] / [0077] / [0078] / [0080] / [0085] / [0088] / [0092] / [0093] / [0143] / [0202] / [0203] / [0205] / [0208] / [0213] / [0215] / [0216] / [0218] / [0219] / [0230] / [0406] / [0407] / [0408] / [0417] / [0418] / [0419] / [0420] / [0421] / [0422] / [0423] / [0424] / [0430] / [0431] / [0432] / [0435] / [0436] / [0441] / [1002] / [1007] / [1008] / [1009] / [1010] / [1011] / [1012] / [1140] / [1145] / [1147] / [1164] / [1207] / [1256] / [1257] / [1273] / [1274] / [1275] / [1276] / [1337]
3		Fucoxanthin	(3S,5R,6S,3'S,5'R,6'R)-5,6-Epoxy-3'-ethanoyloxy-3,5'-dihydroxy-6',7'-didehydro-5,6,7,8,5',6'-hexahydro-b,b-caroten-8-one	VCA0003	Masayoshi Ito		C₄₂H₅₈O₆	658.906		Singlet oxygen quenching activity (Ref. 0230/0441). Anti-tumor acitivity (Ref. 0095/0096/0217/0235). Fucoxanthin inhibited tumor development in skin and duodenal carcinogenesis models of mouse (Ref. 1204). Fucoxanthin, lycopene and lutein decreased the number of aberrant crypt foci in colons in mice (Ref. 1206). Fucoxanthin showed anti-tumor promoting activity in mouse skin carcinogenesis (Ref. 1213). Fucoxanthin induces apoptosis and enhances the antiproliferative effect of the PPAR&gamma& ligand, troglitazone, on colon cancer cells (Ref. 1360). Fucoxanthin from edible seaweed, Undaria pinnatifida, shows antiobesity effect through UCP1 expression in white adipose tisues (Ref. 1361). Light-harvesting pigment (Ref. 0008/0009/0046/0220) Fucoxanthin-chlorophyll a/c-protein assembly (FCPA) with energy transfer activity from fucoxanthin to chlorophyll a and from chlorophyll c to chlorophyll a is isolated from Dictyota dichotoma (brown alga); 10 fucoxanthin, 1 violaxanthin, no b-carotene, 3 chlorophyll c, 13 chlorophyll a and a 54 kDa protein to form a 4.8 S complex (Ref. 1115). Fucoxanthin-chlorophyll proteins are purified from the centric diatom Cyclotella meneghiniana. They contain 18 and 19 kDa subunits, fucoxanthin, chlorophyll a and c, and have energy transfer activity (Ref. 1327).	164C (evacuated tube) (Ref. 0027/0029)						lmax (nm): ethanol 266, 449, 467 sh; hexane 264, 426, 448, 477 [Spectrum 0005] (Ref. 0006); hexane 428 sh, 446, 475, %III/II=40; acetone 420 sh, 444, 467, %III/II=5; HPLC eluent 330, 427 sh, 445, 471, %III/II=6 (Ref. 0029); methanol [Spectrum 1103]	nmax(KBr)/cm^-¹: 3440 (OH), 1929 (allene), 1734 (OAc), 1658 (conj. CO) and 1608 (C=C) (Ref. 0006) nmax(KBr)/cm^-¹: 3483(OH), 3030-2856 (CH), 1930 (allene), 1732 (C=O acetate), 1654 (conj. CO), 1607, 1576, 1530, 1471, 1456 (CH2), 1385 and 1367 (gem-Me), 1335, 1261, 1245 (C-O acetate), 1201, 1175-1157, 1071, 1053, 1032, 958 (trans disubstituted C=C), 917 (Ref. 0029/0033)	¹H-NMR d(500 MHz, CDCl3): 0.96 (3H, s, 1eq-Me), 1.04 (3H, s, 1ax-Me), 1.07 (3H, s, 1'eq-Me), 1.22 (3H, s, 5-Me), ca. 1.35 (2ax-H), 1.35 (3H, s, 5'-Me), 1.39 (3H, s, 1'ax-Me), 1.41 (1H, t, J 12, 2'ax-H), ca. 1.49 (2eq-H), 1.51 (1H, t, J 13, 4'ax-H), 1.79 (1H, dd, J 14, 9, 4ax-H), 1.82 (3H, s, 9'-Me), 1.95 (3H, s, 9-Me), 1.99 (6H, s, 13-, 13'-Me), ca. 2.00 (2'eq-H), 2.04 (3H, s, OAc), 2.29 (1H, ddd, J 13, 4, 2, 4'eq-H), 2.32 (1H, br dd, J 14, 4.5, 4eq-H), 2.60 and 3.66 (each 1H, d, J 18, 7-H2), 3.82 (1H, m, 3-H), 5.38 (1H, m, 3'-H), 6.06 (1H, s, 8'-H), 6.13 (1H, dd-like, J 11, 1, 10'-H), 6.27 (1H, br d, J 11.5, 14'-H), 6.35 (1H, d, J 15, 12'-H), 6.41 (1H, br d, J 11.5, 14-H), 6.57 (1H, dd, J 15, 11, 11-H), 6.60 (1H, dd, J 15, 11, 11'-H), 6.64 (1H, dd, J 14.5, 11.5, 15-H), 6.67 (1H, d, J 15, 12-H), 6.75 (1H, dd, J 14.5, 11.5, 15'-H) and 7.15 (1H, br d, J 11, 10-H) [Spectrum 0006] (Ref. 0006/0028/0029) ¹³C-NMR d(100.6 MHz, CDCl3): 35.79, 35.17 (1, 1'), 47.11, 45.45 (2, 2'), 64.35, 68.01 (3, 3'), 41.69, 45.25 (4, 4'), 66.16, 72.71 (5, 5'), 67.09, 117.53 (6, 6'), 40.83, 202.37 (7, 7'), 197.87, 103.39 (8, 8'), 134.55, 132.51 (9, 9'), 139.11, 128.55 (10, 10'), 123.40, 125.70 (11, 11'), 145.04, 137.16 (12, 12'), 135.55, 138.09 (13, 13'), 136.55, 132.19 (14, 14'), 129.44, 132.51 (15, 15'), 25.06, 29.21 (16-ax, 16'-ax), 28.15, 32.10 (17-eq, 17'-eq), 21.18, 31.31 (18, 18'), 11.84, 14.03 (19, 19'), 12.78, 12.93 (20, 20') (Ref. 0028/0061)	(210C, 70 eV) m/z (ion, intensity relative to base peak in %): 658 (M, 23), 640 (M-18, 37), 622 (M-18-18, 26), 580 (M-18-60, 21), 578 (M-80, 7), 562 (M-18-18-60, 13), 560 (M-18-80, 6), 488 (9), 484 (7), 482 (8), 237 (27), 221 (43), 212 (51), 197 (100) [Spectra 0007 ] (Ref. 0029)	CD data in EPA solution: [Spectrum 0008] (Ref. 0006/0028/0029) Fluorescence properties (Ref. 1162)	TLC (silica plates, 0.5 mm, Kieselgel 60 Merck, hexane-acetone 7:3) Rf = 0.26 (Ref. 0029) HPLC (column: Spherisorb S 5-W, eluent: hexane-isopropyl acetate-isopropyl alcohol-N-ethyl-diisopropylamine 83.9:14:2:0.1, flow: 1.5 ml/min) tR = ca. 35 min [Chromatogram 0006] (Ref. 0002/0030) HPLC (column: CHIRALCEL OD; DAICEL IND., LTD., 1.025 cm, eluent: EtOH-hexane 15:85, temp.: 37C, flow: 2.2 ml/min) tR = 20 min [Chromatogram 0007] (Ref. 0005/0006)	Brown algae (Fucus serratus) (Ref. 0027/0033) Macroalgae (Pheophyceae) (Ref. 0033) Marine Phytoplankton (Bacilliarophyceae, Dinophyceae, Prymnesiophyceae, Prasinophyceae, Chlorophyceae, Cryptophyceae, Rhodophyceae, Cyanophyceae) (Ref. 0033/0034) Sea squirts (Halocynthia roretzi) (Ref. 0035/0401/0402/0411) Shell fish (Tapes philippinarum) (Ref. 0403) (Mytilus edulis) (Ref. 0426) Shell fish (Ref. 0411) All-E (3S,5R,6S,3'S,5'R,6'R)-fucoxanthin is the only naturally occurring stereoisomer in brown algae (Ref. 1163).	Double Wittig condensations of the C10-dialdehyde with the 8-oxo-C15-phosphonium salt and the allenic C15-phosphonium salt provided the C40-skeletal compound, which was treated with MCPBA to afford fucoxanthin. These phosphonium salts were derived from the common intermediate, the C15-a-acetytlenic alcohol, which was synthesized via the coupling reaction of protected (4R,6R)-4-hydroxy-2,2,6-trimethylcyclohexanone with the protected (E)-3-methylpent-2-en-4-yn-1-ol. Key step was effective conversion of the C15-a-acetytlenic alcohol into the C15-8-oxo-compound using oxo-metallic catalyst and subsequent iodine-catalysed double-bond shift. (Ref. 0005/0006)	Sea squirt: Fucoxanthin fucoxanthinol halocynthiaxanthin mytiloxanthin mytiloxanthinone (Ref. 0401) Fucoxanthin fucoxanthinol amarouciaxanthin A amarouciaxanthin B (Ref. 0401) Shell fish (Mytilus edulis): Fucoxanthin fucoxanthinol halocynthiaxanthin mytiloxanthin (Ref. 0404) In lying hens, fucoxanthin in Fucus serratus (brown algae) is metabolized to fucoxanthinol, and then fucoxanthinol 3'-sulphate and paracentrone (Ref. 1309).		The keto group at C-8 of fucoxanthin is single-bond trans-conformation for the conjugated double bond determined by NMR (Ref. 0028).	[0002] / [0005] / [0006] / [0008] / [0009] / [0027] / [0028] / [0029] / [0030] / [0033] / [0035] / [0046] / [0061] / [0095] / [0096] / [0217] / [0220] / [0230] / [0235] / [0401] / [0402] / [0403] / [0404] / [0411] / [0426] / [0441] / [1115] / [1162] / [1163] / [1204] / [1206] / [1213] / [1309] / [1327] / [1360] / [1361]
4		Halocynthiaxanthin	(3S,5R,6S,3'R)-5,6-Epoxy-3,3'-dihydroxy-7',8'-didehydro-5,6,7,8-tetrahydro-b,b-caroten-8-one	VCA0004	Masayoshi Ito		C₄₀H₅₄O₄	598.854		Anti-neoplastic effect (anti-tumor promotion) (Ref. 0223). Inhibitotory effect on Epstein-Barr virus activation (anti-tumor promotion) (Ref. 0217) Inhibotor of the reverse transcriptases of HIV type 1 and 2 (Ref. 0224). Singlet oxygen quenching activity (Ref. 0230). Suppressing efect of generation of superoxide and nitric oxide (Ref. 1097).	158-160C (Ref. 0035)						lmax (nm): ethanol 279, 423sh, 453, and 475sh (Ref. 0006); hexane 277, 428sh, 452, 477sh [Spectrum 0009] (Ref. 0006); ether 430, 452, and 470 (Ref. 0035)	nmax(KBr)/cm^-¹: 3420 (OH), 2190 (acetylene), 1660 (conj. CO), and 1610 (C=C) (Ref. 0006) nmax(KBr)/cm^-¹: 3350 (OH), 2165 (acetylene), 1645 (conj. CO), and 960 (trans CH=CH) (Ref. 0035)	¹H-NMR d(500 MHz, CDCl3): 0.97 (3H, s, 1eq-Me), 1.04 (3H, s, 1ax-Me), 1.15 (3H, s, 1'ax-Me), 1.20, 1.22 (each 3H, s, 1'eq-, 5-Me), 1.35 (1H, dd, J 12.5, 11, 2ax-H), 1.46 (1H, t, J 12.5, 2'ax-H), 1.52 (1H, m, 2eq-H), 1.79 (1H, dd, J 14, 9.5, 4ax-H), 1.84 (1H, ddd, J 12.5, 3.5, 2, 2'eq-H), 1.93 (3H, s, 5'-Me), 1.95 (3H, s, 9-Me), 1.98 (3H, s, 13'-Me), 2.00 (3H, s, 13-Me), 2.02 (3H, s, 9'-Me), 2.07 (1H, ddd-like, J 17.5, 9.5, 1.5, 4'ax-H), 2.32 (1H, br dd, J 14, 4.5, 4eq-H), 2.43 (1H, br dd, J 17.5, 5.5, 4'eq-H), 2.60, 3.65 (each 1H, d, J 18.5, 7-H2), 3.82 (1H, m, 3-H), 3.99 (1H, m, 3'-H), 6.29 (1H, br d, J 12, 14'-H), 6.36 (1H, d, J 15, 12'-H), 6.41 (1H, d, J 11.5, 14-H), 6.46 (1H, dd-like, J 12, 1, 10'-H), 6.57 (1H, dd, J 15, 12, 11'-H), 6.58 (1H, dd, J 15, 11, 11-H), 6.65 (1H, dd, J 14.5, 11.5, 15-H), 6.67 (1H, d, J 15, 12-H), 6.75 (1H, dd, J 14.5, 12, 15'-H), 7.15 (1H, dd-like, J 11, 1, 10-H) (Ref. 0006)	598 (M), 582 (M-16), 580 (M-18), 565 (M-18-15), 562 (M-18-18), 506 (M-92), 490 (M-92-16), 488 (M-92-18) [Spectrum 0010] (Ref. 0035)		HPLC (column: CHIRALCEL OD; DAICEL IND., LTD., 1.025 cm, eluent: EtOH-hexane 15:85, temp.: 37C, flow: 2.4 ml/min) tR = 14.5 min (Ref. 0006)	Sea squirts (Halocynthia roretzi) (Ref. 0035/0401/0402) Shell fish (Mytilus edulis) (Ref. 0426)	Double Wittig condensations of the C10-dialdehyde with the 8-oxo-C15-phosphonium salt and the acetylenic C15-phosphonium salt provided the C40-skeletal compound, which was treated with MCPBA to afford holocynthiaxanthin. These phosphonium salts were derived from the common intermediate, the C15-a-acetytlenic alcohol, which was synthesized via the coupling reaction of protected (4R,6R)-4-hydroxy-2,2,6-trimethylcyclohexanone with the protected (E)-3-methylpent-2-en-4-yn-1-ol. Key step was effective conversion of the C15-a-acetytlenic alcohol into the C15-8-oxo-compound using oxo-metallic catalyst and subsequent iodine-catalysed double-bond shift. (Ref. 0006)	Sea squirt: fucoxanthin fucoxanthinol halocynthiaxanthin (Ref. 0401)			[0006] / [0035] / [0217] / [0223] / [0224] / [0230] / [0401] / [0402] / [0426] / [1097]
5		Peridinin	(3S,5R,6S,3'S,5'R,6'R)-5,6-Epoxy-3'-ethanoyloxy-3,5'-dihydroxy-6',7'-didehydro-5,6,5',6'-tetrahydro-12',13',20'-trinor-b,b-caroten-19,11-olide	VCA0005	Masayoshi Ito		C₃₉H₅₀O₇	630.810		Anti-tumor activity (Ref. 0097/0217). Quencher of singlet oxygen in Gonyaulax polyedra (Ref. 1269). Light-harvesting pigment (Ref. 0008/0009/0042/0043/0044/0046/0221/0222). An energy transfer pathway in a peridinin-chlorophyll a protein complex (PCP) of Alexandrium tamarense (dinoflagellate) is studied by the femtosecond up-conversion method (Ref. 1114). A peridinin-chlorophyll a protein complex (PCP) of Alexandrium cohorticula (dinoflagellate) contains 37 kDa peptide, 12 peridinin and 2 chlorophyll a molecules per monomer (Ref. 1167).	107-109C (Ref. 0042) 127-131C (Ref. 0041)						lmax (nm): ethanol 472 (Ref. 0002); EtOH 475 (E ¹^%₁_c_m = 1325) (Ref. 0033); hexane 431sh, 456 and 485 (Ref. 0002); acetone 465 (Ref. 0033); hexane/acetone/methanol (89:10:1) 427 sh, 457, 479 sh; hexane 425 sh, 453, 482, %III/II=61 (Ref. 1165); methanol [Spectrum 1104]	nmax(CD Cl3)/cm^-¹: 3600 and 3450 (OH), 1928 (allene) and 1742 (C=O) (Ref. 0002) nmax(KBr)/cm^-¹: 3427 (OH), 3023-2958, 2853 (CH), 1927 (allene), 1739 (C=O), 1640, 1617, 1596, 1521, 1450 (CH2), 1377 and 1364 (gem-Me), 1247 (C-O acetate), 1182, 1161, 1124, 1070, 1046, 1029, 963 (trans disubstituted C=C), 956, 940, 904 (Ref. 0033)(Ref. 1269)	¹H-NMR d(500 MHz, CDCl3): 0.97, 1.20, 1.21 (each 3H, s, 1'-gem-Me and 5'-Me), 1.07 and 1.35 (each 3H, s, 1-gem-Me), 1.26 (1H, dd, J 12.5, 10.5, 2'ax-H), 1.38 (3H, s, 5-Me), 1.38 (1H, dd, J 12, 6, 2ax-H), 1.50 (1H, t-like, J 13, 4ax-H), 1.63 (1H, br d-like, J 12.5, 2'eq-H), 1.64 (1H, dd, J 14.5, 9, 4'ax-H), 1.80 (3H, s, 9-Me), 1.99 (1H, ddd, J 12, 4, 2, 2eq-H), 2.04 (3H, s, OAc), 2.23 (3H, s, 13'-Me), 2.28 (1H, ddd, J 13, 4, 2, 4eq-H), 2.40 (1H, ddd, J 14.5, 4, 1.5, 4'eq-H), 3.90 (1H, m, 3'-H), 5.38 (1H, tt, J 12, 4, 3-H), 5.73 (1H, s, 12'-H), 6.05 (1H, s, 8-H), 6.11 (1H, d, J 12, 10-H), 6.37 (1H, d, J 15.5, 8'-H), 6.38 (1H, dd, J 14, 11, 12-H), 6.45 (1H, d, J 12, 14'-H), 6.51 (1H, dd, J 14, 11, 15-H), 6.61 (2H, dd, J 14, 12, 11-H and 15'-H), 7.02 (1H, s, 10'-H), 7.17 (1H, d, J 15.5, 7'-H) [Spectrum 0011] (Ref. 0002/0036/0037) Previously reported ¹H-NMR assignments of all-trans-(6'R)-peridinin are partly corrected (Ref. 1165). (Ref. 1269) ¹³C-NMR d(100.5 MHz, CDCl3): 35.79, 35.31 (1, 1'), 45.43, 47.07 (2, 2'), 68.04, 64.13 (3, 3'), 45.26, 40.90 (4, 4'), 72.60, 67.56 (5, 5'), 117.57, 70.49 (6, 6'), 202.67, 133.62 (7, 7'), 130.29, 121.78 (8, 8'), 133.93, 124.75 (9, 9'), 128.12, 136.34 (10, 10'), 131.51, 146.76 (11, 11'), 133.00, 119.26 (12, 12'), 133.94 (13'), 138.06 (14'), 128.92, 137.25 (15, 15'), 32.07, 29.52 (16, 16'), 29.15, 24.90 (17, 17'), 31.21, 19.88 (18, 18'), 14.00, 168.78 (19, 19'), 15.40 (20'), 170.50 and 21.40 (AcO) (Ref. 0036/0037) Previously reported ¹³H-NMR assignments of all-trans-(6'R)-peridinin are partly corrected (Ref. 1165).	(210C, 70 eV) m/z (ion, intensity relative to base peak in %): 630 (M, 36), 612 (M-18, 30), 594 (M-18-18, 2), 586 (M-44, 1), 570 (M-60, 9), 568 (M-18-44, 2), 552 (M-18-60, 8), 538(M-92, 6), 221 (10), 181 (33) (Ref. 0033/0037/0041)	CD data in EPA solution: De 220 (-7.1), 241 (-4.9), 270 (-4.0), 296 (-0.2), 328(-2.3), 350 (0), 365 (0.5), 404 (0.3) [Spectrum 0012] (Ref. 0002/0033/3006/0047)	TLC (silica plates, 0.5 mm, Kieselgel 60 Merck, hexane-acetone 7:3) Rf = 0.2 (Ref. 0033) HPLC (column: LiChrosorb CN(7 mm) 0.425 cm, eluent: MeOH-acetone-hexane 1:10:89, flow: 1.5 ml/min) tR = 28 min (Ref. 0002/0003/0004) HPLC (column: Ultrasphere 5CN 0.4625 cm, eluent: hexane-isopropyl acetate-acetone-methnol 76:17:7:0.1, flow: 1.5 ml/min) tR = 11.39 min (Ref. 0033) HPLC (column: Silica Spheri 0.4625 cm, eluent: hexane-isopropyl acetate-acetone-methnol 76:17:7:0.1, flow: 2.0 ml/min) tR = 24.90 min (Ref. 0033)	Marine dinoflagellate (Gyrodinium resplendens, Amphidinium carterae, etc.) (Ref. 0039/0040/0042/0043) Marine phytoplankton (Bacilliarophyceae, Dinophyceae, Prymnesiophyceae, Prasinophyceae, Chlorophyceae, Cryptophyceae, Rhodophyceae, Cyanophyceae) (Ref. 0034) Sea squirt (Botrylloides violaceus) (Ref. 0041) Sea anemone (Anemonia sulcata) (Ref. 0045)	The C22-allenic sulphone and the C15-5,6-epoxy-formyl ester were synthesized from the common starting meterial, (4R,6R)-4-hydroxy-2,2,6-trimethylcyclohexanone, in 13 and 12 steps, respectively. Rection with the formyl ester with the sulphone in the presence of LDA at -78C provided peridinin accompanying with its 11'E-isomer.(Ref. 0001/0002/0031)	Shell fish (Mytilus edulis): Peridinin peridinoniol pyrrhoxanthinol Hydrate-pyrrhoxanthinol (Ref. 0404)		Numbering and stereochemistry are revised (Ref. 1165).	[0001] / [0002] / [0003] / [0004] / [0008] / [0009] / [0031] / [0033] / [0036] / [0037] / [0039] / [0040] / [0041] / [0042] / [0043] / [0044] / [0045] / [0046] / [0047] / [0097] / [0217] / [0221] / [0222] / [0404] / [1114] / [1165] / [1167] / [1269]
6		Pyrrhoxanthin	(3S,5R,6S,3'R)-5,6-Epoxy-3'-ethanoyloxy-3-hydroxy-7',8'-didehydro-5,6-dihydro-12',13',20'-trinor-b,b-caroten-19,11-olide	VCA0006	Masayoshi Ito		C₃₉H₄₈O₆	612.795									lmax (nm): ethanol 466 (Ref. 0002); hexane 437sh, 459, 487 (Ref. 0002); acetone (473), 485 (Ref. 0238); methanol 341, 427 (shoulder), 448, 475, %III/II=27.4 (Ref. 1052)	nmax(CD Cl3)/cm^-¹: 3600 and 3570 (OH), 2160 (acetylene) and 1745 (C=O) (Ref. 0002) nmax(KBr)/cm^-¹ (phyrroxanthin acetate): 3020, 2955, 2925 and 2855 (CH), 2170 (acetylene), 1756 and 1740 (CO), 1630, 1520 (C=C), 1460 (CH2), 1379 and 1366 (Me), 1244, 1231, 1127, 1043, 1030(C-O), 986 (trans -CH=CH-), 943, 905, 820, 768, 725, 643 (Ref. 0040)	¹H-NMR d(500 MHz, CDCl3): 0.94 (3H, s, 1'-Me), 1.14 (3H, s, 1-Me), 1.16 (6H, s, 1-, 5'-Me), 1.17 (3H, s, 1'-Me), 1.22 (1H, dd, J 12.5, 10, 2'ax-H), 1.53 (2ax-H), 1.60 (1H, br d-like, J 12.5, 2'eq-H), 1.60 (1H, dd, J 14.5, 9, 4'ax-H), 1.80 (1H, ddd, J 12.5, 3, 1.5, 2eq-H), 1.87 (3H, s, 5-Me), 1.96 (3H, s, 9-Me), 2.06 (3H, s, OAc), 2.10 (1H, dd, J 17, 9, 4ax-H), 2.19 (3H, s, 13'-Me), 2.36 (1H, ddd, J 14.5, 5, 1.5, 4'eq-H), 2.46 (1H, br dd, J 17, 5, 4eq-H), 3.87 (1H, m, 3'-H), 5.00 (1H, m, 3-H), 5.70 (1H, s, 12'-H), 6.34 (1H, d, J 15.5, 8'-H), 6.36 (1H, dd, J 14.5, 11.5, 12-H), 6.40 and 6.41 (each 1H, d, J 11.5, 10-H, 14'-H), 6.46 (1H, dd, 14, 11.5, 15-H), 6.54 (1H, dd, J 14.5, 11.5, 11-H), 6.60 (1H, dd, J 14, 11.5, 15'-H), 6.98 (1H, s, 10'-H) and 7.14 (1H, d, J 15.5, 7'-H) (Ref. 0002/0038) ¹³C-NMR d(100.6 MHz, CDCl3): 36.12, 35.31 (1, 1'), 42.29, 47.12 (2, 2'), 67.90, 67.52 (3, 3'), 37.54, 40.94 (4, 4'), 137.26, 67.52 (5, 5'), 124.27, 70.45 (6, 6'), 90.06, 133.74 (7, 7'), 98.54, 121.79 (8, 8'), 121.00, 124.91 (9, 9'), 134.63, 136.30 (10, 10'), 130.63, 146.93 (11, 11'), 133.74, 119.12 (12, 12'), 134.43 (13'), 137.83 (14'), 136.88, 129.85 (15, 15'), 32.07, 29.52 (16, 16'), 28.67, 24.89 (17, 17'), 22.41, 19.87 (18, 18'), 18.10, 168.73 (19, 19'), 15.43 (20'), 170.70 and 21.39 (AcO) (Ref. 0038)	m/z (ion, intensity relative to base peak in %) (phyrroxanthin acetate): 654 (M, 21.2), 526 (M-28, 0.7), 612 (M-42, 1.2), 594 (M-60, 5.0), 579 (M-75, 2.3), 574 (M-80, 1.0), 562 (M-92, 1.2), 478 (5.7), 450 (1.8), 303 (10.7), 285 (10.6), 233 (7.6), 223 (15.3) (Ref. 0040/0238)	CD data: De 215 (-7.3), 218 (-5.4), 224 (-6.3), 228 (-5.3), 233 (-5.4), 242 (-5.0), 252 (-6.6), 260 (-7.0), 285 (-2.1), 321 (-1.1) (Ref. 0081)	HPLC (column: LiChrosorb CN(7 mm) 0.725 cm, eluent: acetone-hexane 12:88, flow: 2.0 ml/min) tR = 20.5 min (Ref. 0002) TLC (silica plates, acetone-heptane, 2:8) Rf=0.11 (Ref. 0238) TLC (alkaline plates, acetone-heptane, 3:7) Rf=0.41 (Ref. 0238>	Marine dinoflagellate (Gyrodinium resplendens, Amphidinium carterae, etc.) (Ref. 0039/0040)	Rection with the C15-5,6-epoxy-formyl ester with the C22-acetylenic sulphone in the presence of LDA at -78C provided pyrroxanthin accompanying with its 11'E-isomer. (Ref. 0002)				[0002] / [0038] / [0039] / [0040] / [0081] / [0238] / [1052]
7		Zeaxanthin/ (3R,3'R)-Zeaxanthin	(3R,3'R)-b,b-Carotene-3,3'-diol	VCA0007	Masayoshi Ito		C₄₀H₅₆O₂	568.871		Antioxidant activity (Ref. 0092/0093/0215/0225/0226) Singlet oxygen quenching activity (Ref. 0215/0230) Reinforcement of phospholipid bilayer (Ref. 0237) Inhibitotory effect on Epstein-Barr virus activation (anti-tumor promotion) (Ref. 0217) Zeaxanthin inhibited the development of mouse spontaneous liver cancer (Ref. 1207). Zeaxanthin showed anticarcinogenic activity in liver in mice (Ref. 1208). Typical lutein and zeaxanthin levels in the human eye (Ref. 1301). (3R,3'R)-Zeaxanthin, meso-zeaxanthin and (3R,3'R,6'R)-lutein are located in human macular (Ref. 1168/1169). A membrane-associated xanthophyll-binding protein, which is a Pi isoform of human glutathione S-transferase (GSTP1), is purified from hman macula. It binds (3R,3'R)-zeaxanthin and (3R,3'S-meso)-zeaxanthin, but not lutein A (Ref. 1326). A water-soluble surface-associated complex from Prochlorothrix hallandica composed of two polypeptides of 56 and 58 kDa, zeaxanthin and lipopolysaccaride (Ref. 1161).	207-208C (Ref. 0014/0049)						lmax (nm) (e): hexane 452 (133692), 480 (116624) (Ref. 0014/0049); EPA (e) 273 (22000), 340 (7300), 450 (139300) (Ref. 0048); methanol 275, 341, 429 (shoulder), 448, 473, %III/II=22 [Spectrum 1105] (Ref. 1064)	nmax(KBr)/cm^-¹: [Spectrum 0013] (Ref. 0065)	¹H-NMR d(CDCl3): 1.48 (2, 2'ax-H), 1.77 (2,2'eq-H), ca. 4.00 (3, 3'-H), 2.04 (4, 4'ax-H), 2.39 (4,4'eq-H), 6.11 (7, 7'-H), 6.13 (8, 8'-H), 6.16 (10, 10'-H), 6.64 (11, 11'-H), 6.36 (12, 12'-H), ca. 6.26 (14, 14'-H), ca. 6.63 (15, 15'-H), 1.074 (1, 1'-gem-Me), 1.736 (5, 5'-Me), 1.967, 1.972 (9, 9', 13, 13'-Me), ca. 1.35 (OH) (Ref. 0048) More precise data (Ref. 1080) ¹³C-NMR d(CDCl3): 37.1 (1, 1'), 48.2 (2, 2'), 65.1 (3, 3'), 42.4 (4, 4'), 126.1 (5, 5'), 137.6 (6, 6'), 125.5 (7, 7'), 138.5 (8, 8'), 135.7 (9, 9'), 131.3 (10, 10'), 124.9 (11, 11'), 137.6 (12, 12'), 136.5 (13, 13'), 132.6 (14, 14'), 130.0 (15, 15'), 28.7, 30.2 (1, 1'-gem-Me), 21.7 (5, 5'-Me), 12.8 (9, 9'-Me), 12.8 (13, 13'-Me) (Ref. 0061).	m/z: 568 (M, 100%), 550 (M-18, 84%), 532 (M-18-18, 5%), 489 (M-79, 1%), 476 (M-92, 13%), 462 (M-106, 1%), 458 (M-18-92, 11%), 444 (M-18-106, 1%), 410 (M-158, 5%) (Ref. 0058/0059) FD-MS m/z: 568 (Ref. 1064)	CD data in EPA solution (25C): De 225 (-7.7), 254 (+8.1), 290 (-14.6), 348 (+3.7) [Spectrum 0014] (Ref. 0048/0064/0078) CD data in EPA solution (25C): De 224 (-18.0), 236 (0), 245 (+18.0), 260 (0), 284 (-24.0), 325 (0), 350 (+4.0), 380 (+0.5) (Ref. 0405)	HPLC (column: Spherisorb S5W 0.3150 cm, eluent: hexane-CH2Cl2-isopropyl alcohol-Hünig's base, 90.9:6.5:2.5:0.1) [Chromatogram 0008] (Ref. 0048) HPLC (columun: Sumipax OA-2000 (5mm) 0.830 cm, eluent: hexane-CH2Cl2-EtOH 90:10:0.1, flow: 1.5 ml/min) tR = ca. 40 min (meso), ca. 45 min (3R,3'R), ca. 50 min (3S,3'S) [Chromatogram 0009] (Ref. 0069/0405) A reversed-phase HPLC procedure for quantitative measurement in serum of seven carotenoids (lutein, zeaxanthin, canthaxanthin, b-cryptoxanthin, lycopene, a-carotene and b-carotene) has been developed (Ref. 0227). Separation of zeaxanthin and lutein by Novapak C₁₈ HPLC column (8 100 mm, RCM-type, Waters) (Ref. 1150) and by Spherisorb ODS-1 HPLC column (4.6 250 mm) (Ref. 1151).	Sea squirts (Halocynthia roretzi) (Ref. 0035) , Shell fishes (Ref. 0405/0410/0411) , Fishes (Ref. 0405/0410/0411) Anacystis nidulans (Cyanobacterium) (Ref. 1077), Cyanophora paradoxa (Glaucocystophyte) (Takaichi Shinichi), Red algae (Bangia fucopurupurea, Gigartina stellata, Ceramium rubrum, Polysiphonia brodiaei, Polysiphonia urceolata) (Ref. 0058), Higher plants (Ref. 0409) Paracoccus zeaxanthinifaciens R1534 (bacterium; previous name Flavobacterium sp.) (Ref. 1236) Erythrobacter longus (aerobic photosynthetic bacterium) (Ref. 1055)	The protected (4R,6R)-4-hydroxy-2,2,6-trimethylcyclohexanone was reacted with lithium acetylide and deprotected to give the acetylenic diol, which was acetylated and dehydrated to provide the 3-acetoxy-C11-terminal alkyne. This was converted into the C15-phosphonium salt via the intermediate vinyl carbinol in an overall yield of 72% from the starting hydroxyketone. Wittg condensation of the phosphonium salt with the C10-dialdehyde provided (3R,3'R)-zeaxanthin. (Ref. 0019/0053) (R)- and (S)-3-Hydroxy-b-cycloitrals prepared by hydroboration of safranol isopropenylether with (+)- and (-)-diisopinocampenylborane were transformed into (3R,3'R)-, (3S,3'S)- and (3R,3'S: meso)-zeaxanthin, via the Wittig condensation of the corresponding C15-phosphonium salt with the C10-dialdehyde. (Ref. 0019/0076)The protected (4R,6R)-4-hydroxy-2,2,6-trimethylcyclohexanone was reacted with dimethyl sulphonium methylide to give the allylic epoxide, which was transformed into (R)-3-hydroxy-b-cyclocitral. This was converted into the C15-phosphonium salt, then condensed with the C10-dialdehyde to give (3R,3'R)-zeaxanthin. (Ref. 0014/0057) The protected (4R,6R)-4-hydroxy-2,2,6-trimethylcyclohexanone was transformed with the protected (E)-3-methylpent-2-en-4-yn-1-ol into a C15-intermediate, which was converted into the C15-phosphonium salt. (Ref. 0049) The (R)-3-hydroxy-C15-sulphone was coupled with the C10-dialdehyde using BuLi as a base. The resulting dihydroxy compound was acetylated in situ and treated with aqueous NaOH to afford all-E-11,11'-bis-sulphonyl-zeaxanthin. Subsequent elimination of the sulphonyl group gave (3R,3'R)-zeaxanthin. (Ref. 0026)	The gene product catalyzes the conversion of b-carotene to zeaxanthin by way of b-cryptoxanthin under the presence of O₂, Fe²⁺, and 2-oxoglutarate (Ref. 0205). Capsicum annuum (pepper) fruits contain two kinds of b-carotene hydroxylase. Both enzymes require iron, ferredoxin and NADPH for activity, use iron activated oxygen to break the C-H bond, and introduce a hydroxyl group (Ref. 1134). Cofactors of zeaxanthin-epoxidase from spinach are FAD, NAD(P)H and O₂ (Ref. 1153). Zeaxanthin in Sphingobacterium multivorum is synthesized via non-mevalonate pathway (Ref. 1138). Zeaxanthin is accumulated in the cytoplasmic membranes of Synechococcus sp. strain PCC 7942 (cyanobacteria) grown under high light condition (Ref. 1146). [Table 1026] Zeaxanthin is cleavated to crocetindial and hydroxy-b-cyclocitral by b-carotene 7,8(7',8') oxygenase of Microcystis (cyanobacterium) by freezing the cell pellet. The enzyme requires O₂ and iron, but is sensitive to sulfhydryl reagents, antioxidants and chelation reagents, and is membrane bound (Ref. 1266). Carassius auratus (gold fish): Zeaxanthin -> b-carotene-3,4,3'-triol -> b-doradexanthin -> astaxanthin (Ref. 0415) Parasilurus asotus (Japanese common catfish): Zeaxanthin -> parasiloxanthin -> 7,8-dihydroparasiloxanthin (Ref. 0416) Tilapia nilotica (Tilapia): Zeaxanthin -> rhodoxanthin (Ref. 0417) Zeaxanthin -> 3,4-didehydroretinol (Ref. 0417/0216) Zeaxanthin -> e, e-carotene-3,3'-dione -> 3-hydroxy-e, e-caroten-3'-one (Ref. 0417) hen's egg yolk: zeaxanthin -> e,ee-carotene-3,3'-dione (Ref. 0428)	Genes required for the biosynthesis of zeaxanthin from farnesyl diphosphate (FPP) were clarified in epiphytic bacteria Erwinia species for the first time in the beginning of the 1990's (Ref. 0201/1001). Zeaxanthin is synthesized from FPP by five crt gene products, CrtE, CrtB, CrtI, CrtY, and CrtZ (Ref. 1002). [Table 0003] Nowadays, the b-carotene hydroxylase gene is isolated from various organisms such as gram-negative bacteria (crtZ), cyanobacteria (crtR), and higher plants (crtR-b), and some higher plants contain two kinds of b-carotene hydroxylase genes (Ref. 0202/0204/1013/1014/1133/1134/1279). Review of characteristics of zeaxanthin epoxidase and violaxanthin de-epoxidase (Ref. 1268) CrtZ from Thermus thermophilus (Gram-negtive bacteria) is P450-type monooxygenase, while other CrtZ and CrtR are non-heme type (Ref. 1283).	Highly deuterated zeaxanthin has recently been synthesized from fully deuterated mevalonolactone by using triply engineered Escherichia coli, which carries the five Erwinia crt genes from FPP to zeaxanthin and the genes involved in mevalonate pathway from mevalonate to isopentenyl diphosphate (IPP), by a Japanese group (Ref. 1084). This compound should be useful for various biological experiments for examining its metabolism. Semi-empirical molecular orbital calculations using AM1 Hamiltonian (MNDO-AM1 method) were performed in order to predict their stable structures (Ref. 1337).	[0014] / [0019] / [0026] / [0035] / [0048] / [0049] / [0053] / [0057] / [0058] / [0059] / [0061] / [0064] / [0065] / [0069] / [0076] / [0078] / [0092] / [0093] / [0201] / [0202] / [0204] / [0205] / [0215] / [0216] / [0217] / [0225] / [0226] / [0227] / [0230] / [0237] / [0405] / [0409] / [0410] / [0411] / [0415] / [0416] / [0417] / [0428] / [1001] / [1002] / [1013] / [1014] / [1055] / [1064] / [1077] / [1080] / [1084] / [1133] / [1134] / [1138] / [1146] / [1150] / [1151] / [1153] / [1161] / [1168] / [1169] / [1207] / [1208] / [1236] / [1266] / [1268] / [1279] / [1283] / [1301] / [1326] / [1337]
8		Mytiloxanthin	(3R,3'S,5'R)-3,3',8'-Trihydroxy-7,8-didehydro-b,k-carotene-6'-one	VCA0008	Masayoshi Ito		C₄₀H₅₄O₄	598.854		Inhibitotory effect on Epstein-Barr virus activation (anti-tumor promotion) (Ref. 0217)	147C (Ref. 0035/0051)						lmax (nm): ether 294, 469 (Ref. 0050); CS2 496 (Ref. 0051); ethanol 470 (Ref. 0051); benzene 480 (e 85700) (Ref. 0051); acetone 470 (Ref. 0238)	nmax(CD Cl3)/cm^-¹: 3680, 3610, 2950, 2920, 2850, 2170, 1605, 1560, 1460, 1380, 1100, 1050, 1030, 970 (Ref. 0051) nmax(CD Cl3)/cm^-¹ : 2170, 965 (Ref. 0051)	¹H-NMR d(300 MHz, CDCl3): 1.46 (dd, J 12, 12, 2ax-H), 1.84 (ddd, J 12, 3.5, 2), 3.99 (dddd, J 12, 9.5, 5.5, 3.5, 3-H), 2.07 (dd, J 17.5, 9.5, 4ax-H), 2.43 (dd, ddd, J 17.5, 5.5, 2, 4eq-H), 6.46 (d, J 11.5, 10-H), 6.54 (dd, J 14.5, 11.5, 11-H), 6.36 (d, J 14.5, 12-H), 6.28 (d, J 10.5, 14-H), 6.70 (d, J 14, 10.5, 15-H), 1.15 (s, 1ax-Me), 1.20 (s, 1eq-Me), 1.93 (s, 5-Me), 2.01 (s, 9-Me), 1.98 (s, 13-Me), 2.19 (dd, J 13.5, 8, 2'a-H), 1.72 (dd, J 13.5, 4.5, 2'b-H), 4.53 (dddd, J 8.5, 8, 4.5, 2.5, 3'-H), 2.88 (dd, J 14.5, 8.5, 4'a-H), 1.55 (dd, J 14.5, 2.5, 4'b-H), 5.86 (s, 7'-H), 7.23 (d, J 9.5, 10'-H), 6.62 (dd, J 15, 9.5, 11'-H), 6.65 (d, J 15, 12'H), 6.38 (d, J 10.5, 14'-H), 6.65 (dd, J 14, 10.5, 15'-H), 0.85 (s, 1'a-Me), 1.19 (s, 1'b-Me), 1.35 (s, 5'b-Me), 1.98 (s, 9'Me), 1.99 (s, 13'-Me), 16.30 (s, 8'-OH). (Ref. 0050)	EI-MS m/z (ion, intensity relative to base peak in %): 598 (M, 23), 580 (M-18, 5), 562 (M-36, 1), 471 (M-127, 1), 401 (M-197, 20), 197 (17), 179 (25), 109 (90), 92 (100) (Ref. 0035/0050/0238)	CD data in ether solution: De 225 (-0.5), 280 (0), 294 (+0.7), 305 (0), 360 (-1.0) (Ref. 0050/0051)	TLC (silica plates on alkaline plates, trichloroethane-MeOH, 100:5) Rf=0.36 (Ref. 0238) HPLC (columun: Shim-Pak Prep-ODS (Shimadzu) (5mm) 2.025 cm, eluent: CH2Cl2-MeCN 5:95, flow: 10 ml/min) tR = ca. 7 min [[Maoka Takashi]	Sea squirts (Halocynthia roretzi) (Ref. 0035) Mussel (Mytilus coruscus, Mytilus edulis, Mytilus californianus) (Ref. 0050/0051/0052/0426/0427/0434)	Condensation of 1-acetyl-1,2,2-trimethyl-4-trimethylsilyloxycyclopentane with methyl 12,12-ethylenedioxy-2,6,11-trimethyldodeca-2,4,6,8,10-pentaenoate, and removal of the protecting group, gave the b-diketone derivatives, which reacted with the C15-acetylenic Wittig salt to yield a cis-isomer of mytiloxanthin. Mytiloxanthin itself has not been synthesized. (Ref. 0051)				[0035] / [0050] / [0051] / [0052] / [0217] / [0238] / [0426] / [0427] / [0434]
9		a-Carotene/ b,e-Carotene	(6'R)-b,e-Carotene	VCA0009	Masayoshi Ito		C₄₀H₅₆	536.873		Singlet oxygen quenching activity (Ref. 0088) Anti-tumor activity (Ref. 0098/0217/0229) Antioxidant activity (Ref. 0092/0093) Preventive action against carcinogenesis (Ref. 0236) a-Carotene was more potent than b-carotene in suppressing tumorigenesis in skin and lung of mouse (Ref. 1204). The antitumorigenic activity of a-carotene was stronger than that of b-carotene, while both a- and b-carotene inhibited the tumorigenesis in skin, lung, liver and colon in mice (Ref. 1208). a-Carotene reduced the expression of N-myc gene and induced G0/G1 arrest in GOTO cells, and showed more potent inhibitory activity than b-carotene in skin carcinogenesis (Ref. 1209). The moderate dose of a- and b-carotenes and lycopene enhanced gap-junctional intercellular communication (Ref. 1210). Palm carotene and b-carotene inhibited pancreatic carcinogenesis in hamsters, but a-carotene showed no effects (Ref. 1212).	160-162C (racemate) (Ref. 0082) 178C (optical active) (Ref. 0083)				(6'S): [a]₆₄₃¹⁸ = -400 (benzene) (Ref. 0083) (6'S): [a] = -556 (benzene) (Ref. 0084) (6'R): [a]₆₄₃¹⁸ = +385 (benzene) (Ref. 0083)		lmax (nm): petro 420, 444, 473 (Ref. 0058/0079); methanol 335, 422 (shoulder), 442, 471, %III/II=61.2 [Spectrum 1106] (Ref. 1052); acetonitrile/methanol/THF (58:35:7) 272, 334, 426 (shoulder), 448, 476, %III/II=58 [Spectrum 1002] (Ref. 1057)	KBr disc or pellet: [Spectrum 0015] (Ref. 0065)	¹H-NMR d(400 MHz, CDCl3): 0.82 and 0.90 (each 3H, s, 1'-gem-Me), 1.03 (6H, s, 1-gem-Me), 1.58 (3H, br s, 5'-Me), 1.72 (3H, s, 5-Me), 1.91 (3H, s, 9'-Me), 1.96 and 1.97 (9H, s, 9-, 13-, 13'-Me), 2.18 (1H, d, J 9, 6'-H), 5.41 (1H, m, 4'-H), 5.52 (1H, dd, J 15.5, 9, 7'-H), 6.14 (2H, s, 7-, 8-H), 6.08-6.68 (ca. 11H, m, conj. olefinic). (Ref. 0079)	m/z: 536 (M, 53%), 480 (M-56, 2%), 444 (M-92, 12%), 430 (M-106, 2%) (Ref. 0058/0079)	CD in EPA solution: De 238 (4.2), 266 (4.0), 298 (0.4), 330 (1.1), 362 (0.1) and 400 (2.0) (Ref. 0079)	TLC (silica gel-G-Ca(OH)2-MgO-CaSO4 (10:4:3:1), petrol-acetone 97:3) Rf = 0.84 (Ref. 0079) HPLC (column: Vydac 218TP54, acetonitrile-methanol-tetrahydrofuran 40:56:4, flow: 1 ml/min) tR = ca. 10 min [Chromatogram 0003] (Ref. 0067) A reversed-phase HPLC procedure for quantitative measurement in serum of seven carotenoids (lutein, zeaxanthin, canthaxanthin, b-cryptoxanthin, lycopenes, a-c arotene and b-carotene) has been developed. (Ref. 0227) Retinol, a-tocoherol, lutein, all-trans-lycopene, and a- and b-carotenes were determined in human plasma by reversed-phase HPLC. (Ref. 0228) HPLC (column; Novapak C18 (Waters) 8 X 100 mm: eluelnt; acetonitrile/methanol/THF 58:35:7: flow 2.0 ml/min) Rt=17.7 min (Ref. 1057)	Nemalion helminthoides, Bonnemaisonia hamifera, Rhodymenia palmata, Ceramium rubrum (red algae) (Ref. 0058) carrot, palm (higher plants) (Ref. 0236)	Wittig reaction of dehydro-b-apo-12'-carotenal (C25) with a-ionylideneethyl-triphenylphosphonium chroride (C15) using NaOMe as base provided 15,15'-dehydro-a-carotene, which was transformed by partial reduction and isomerization to racemic a-carotene. (Ref. 0082) The enantiomerically pure a-ionone obtained via resolution of racemic (2,6,6-trimethylcyclohex-2-enyl)prop-2-enoic acid was reacted with vinyl magnesium chloride to give the C15-alcohol. This was converted into the phosphonium salt and then condensed with b-apo-12'-carotenel (C25) using NaOMe as base to give naturally occuring (6'R)-a-carotene in 45% referred to (6'R)-a-ionone. (6'S)-a-carotene has been synthesized in an analogous way. (Ref. 0019) By use of enantiomeric (S)- and (R)-a-ionones obtained by resolution of the racemate via the methylhydrazones, (6'S)- and (6'R)-a-ionones was synthesized for the first time. (Ref. 0019/0083)	[Table 1027]	In Arabidopsis, lycopene is at first cyclized to d-carotene by lycopene e-cyclase, and then to a-carotene by lycopene b-cyclase (Ref. 1015). CrtL-e from the marine cyanobacterium Prochlorococcus marinus MED4 has bifunctional activety (lycopene e- and b-cyclases), and poduces a-carotene (Ref. 1242).	Biotechnological achievement has recently been made in relations with the supply of a-carotene, by Calgene LLC, i. e., a transgenic canola (Brassica napus), which accumulates a great amount of a-carotene as well as b-carotene in seeds, has been constructed by over-expressing the Erwinia phytoene synthase gene crtB (Ref. 1016). Gel filtration of carrot root chromoplasts yields one major carotenoprotein, in which one unit contains one a-carotene and two b-carotene in 54-kDa peptide (Ref. 1272).	[0019] / [0058] / [0065] / [0067] / [0079] / [0082] / [0083] / [0084] / [0088] / [0092] / [0093] / [0098] / [0217] / [0227] / [0228] / [0229] / [0236] / [1015] / [1016] / [1052] / [1057] / [1204] / [1208] / [1209] / [1210] / [1212] / [1242] / [1272]
10		Lycopene	y,y-Carotene	VCA0010	Masayoshi Ito		C₄₀H₅₆	536.873		Inhibitory effect on colonic aberrant crypt foci formation (anti-tumor promotion) (Ref. 0229/1019) Effects on intrathymic T cell differentiation and peripheral CD4/CD8 ratio (Ref. 0231) Singlet oxygen quenching activity (Ref. 0088/0441) Inhibitotory effect on Epstein-Barr virus activation (anti-tumor promotion) (Ref. 0217) Effects lowering risk of prostate cancer (Ref. 1020) Biological activities of lycopene are antioxidant activity (singlet oxygen quenching and peroxyl radical scavenging), induction of cell-cell communication, and growth control, but no provitamin A activity. Epidemiological studies suggest protective effects of lycopene on some types of cancer, e.g., prostate cancer (Ref. 1154). Lycopene or tomato-rich diets decrease the prostate cancer risk. No study indicated that higher tomato consumption or lycopene blood levels statistically significantly increased the risk of cancer of any site (Ref. 1170). The crystal structure of the light-harvesting complex II (B800-850) from Rhodospirillum molischianum (present name; Phaeospirillum molischianum) (purple bacterium): 8* (one lycopene, one B800 BChl, two B850 BChl, one a-polypeptide and one b-polypeptide) (Ref. 1152). The administration of lycopene in drinking water inhibited the incidences and multiplicities of lung adenomas plus carcinomas combined in mouse multi-organ carcinogenesis model in male mice but not in females (Ref. 1197). The inhibitory effect of tomato juice rich in lycopene (17 ppm) was observed in rat colon carcinogenesis model (Ref. 1198). The tomato juice containing lycopene decreased the numbers, but not incidences, of urinary bladder transitional cell carcinomas in male rats (Ref. 1199). Lycopene (50 ppm in drinking water) had inhibitory effect on lung carcinogenesis in male mice (Ref. 1200). Long-term (6 to 76 weeks of age) administration of a diet containing 0.005% lycopene did not reduce the risk of hepatocarcinogenesis in a rat spontaneous liver carcinogenesis model (Ref. 1201). The inhibitory effect of lycopene containing diet was not seen in rat prostate carcinogenesis models (Ref. 1202). Fucoxanthin, lycopene and lutein decreased the number of aberrant crypt foci in colons in mice (Ref. 1206). Lycopene had anticarcinogenic activities in mammary gland, liver, skin and lung in mouse models, and also inhibited the development of aberrant crypt foci in rat colon (Ref. 1207). The moderate dose of a- and b-carotenes and lycopene enhanced gap-junctional intercellular communication (Ref. 1210). Both lycopene and b-carotene showed no inhibitory effect on the development of rat urinary bladder carcinomas, while combination of carotenoids with NSAID decreased numbers and incidences of cancers (Ref. 1211).	176C (Ref. 0056>						lmax (nm): hexane 286, 295, 425, 448, 476, 507 (Ref. 0056); methanol 293, 360, 442, 468, 499, %III/II=68.7 [Spectrum 1107] (Ref. 1052/1064); acetonitrile/methanol/THF (58:35:7) 296, 364, 447, 473, 504, %III/II=70 [Spectrum 1003] [Spectrum 1051] (Ref. 1057); n-hexane 443.0, 470.5, 502.0 (Ref. 1132)	KBr disc or pellet: [Spectrum 0016] (Ref. 0065)	¹H-NMR d(CDCl3): 5.11 (2, 2'-H), ca. 2.11 (3, 3'-H2), ca. 2.11 (4, 4'-H2), 5.95 (6, 6'-H), 6.49 (7, 7'-H), 6.25 (8, 8'-H), 6.18 (10, 10'-H), 6.64 (11, 11'-H), 6.35 (12, 12'-H), 6.25 (14, 14'-H), 6.62 (15, 15'-H), 1.688, 1.612 (1, 1'-gem-Me), 1.818 (5, 5'-Me), 1.968 (9, 9', 13, 13'-Me) (Ref. 0054) ¹³C-NMR d(CDCl3): 131.64 (1, 1'), 124.12 (2, 2'), 26.83 (3, 3'), 40.30 (4, 4'), 139.30 (5, 5'), 125.94 (6, 6'), 124.87 (7, 7'), 135.54 (8, 8'), 136.15 (9, 9'), 131.64 (10, 10'), 125.21 (11, 11'), 137.46 (12, 12'), 136.54 (13, 13'), 132.71 (14, 14'), 130.17 (15, 15'), 25.66, 17.70 (1, 1'-gem-Me), 16.97 (5, 5'-Me), 12.90 (9, 9'-Me), 12.81 (13, 13'-Me) (Ref. 0054) (CDCl3) (Ref. 1132) 1H- and 13C-NMR in CDCl3 (Ref. 1251)	m/z: 536 (M, 22%), 467 (M-69), 444 (M-92), 430 (M-106), 378 (M-158), 361 (M-106-69) (Ref. 0059/0060) FD-MS m/z: 536 (Ref. 1064)	Fluoresence (Ref. 1062) Raman spectrum in n-hexane (Ref. 1132)	RF-TLC on 0.25 mm RP-18 layers (Merck, Art. 15423) using several ratio of light petroleum (bp 40-60C)-acetonitrile-methanol ex: 1:6:3 Rf=0.16, 3:1:6 Rf=0.27 (Ref. 0135) HPLC (column: Nucleosil-300-5 0.450 cm, eluent: hexane-N-ethyldiisopropylamine, 2000:1, flow: 0.6 ml/min, detect : 469 nm) tR = ca. 27 min (all-E isomer) [Chromatogram 0010] (Ref. 0054) A reversed-phase HPLC procedure for quantitative measurement in serum of seven carotenoids (lutein, zeaxanthin, canthaxanthin, b-cryptoxanthin, lycopenes, a-c arotene and b-carotene) has been developed. (Ref. 0227) Retinol, a-tocoherol, lutein, all-trans-lycopene, and a- and b-carotenes were determined in human plasma by reversed-phase HPLC. (Ref. 0228) HPLC (column; Novapak C18 (Waters) 8 X 100 mm: eluelnt; acetonitrile/methanol/THF 58:35:7: flow 2.0 ml/min) Rt=11.4 min (Ref. 1057)	Phtosynthetic bacteria (Rhdospirillaceae, Chromatiaceae, Chrorobiaceae) (Ref. 0409) Non-photosynthetic bacteria (Mycobacteriacea) (Ref. 0409) Fungi (Phycomycetes, Axcomycetes, Deuteromycetes) (Ref. 0409) Lycopersicon esculentum (tomato) (Ref. 0409) Fruits, flowers, leaves, seeds of higher plant (Ref. 0409) Rhabdochromatium marinum (purple photosynthetic bacterium) accumulates lycopene (Ref. 1119).	Reaction of y-ionone (C13) with propagyl bromide in the presence of zinc gave the acetylenic alcohol, which was acetylated followed by elimination of acetic acid by treatment with potassium t-butoxide to provide the C16-terminal alkyne. This was transformed to the Grignard reagent, which was coupled with the C8-diketone to give the C40-acetylenic diol. The dehydration with NBS gave lycopene in overall yield of 18%. (Ref. 0018) Geranyl bromide, obtained from linalol and phosphorous tribromide, was converted with triphenylphosphine into the C10-phosphonium salt. The Wittig reaction with crocetindialdehyde (C20) and BuLi as base gave lycopene in an overall yield of 36%. (Ref. 0018/0055) y-Ionone was reacted with lithium acetylide to give the a-acetylenic alcohol, which was reduced with H2 and Lindlar catalyst to provide vinyl-y-ionol. This was converted with triphenylphosphine hydrobromide with the C15-phosphonium salt, and condensed with the C10-dialdehyde using sodium methoxide as base to give lycopene in an overall yield of 20%. (Ref. 0018/0056) Geranyldiethylamine was converted into geranylsulphone (C10) by reaction with ethyl chloroformate and sodium chlorophenylsulphate. Treatment of this sulphone with BuLi, crocetindialdehyde (C20), acetic anhydride and base led to the C40-disulphone with a di-cis configuration. Reduction with disodium dithionite gave all-E-lycopene. (Ref. 0018/0026)	[Table 1023] Lycopene is synthesized from phytoene and z-carotene through four-step (CrtI) and two-step (CrtQ, ZDS) dehydrogenation reactoins, by carotenogenic microorganisms such as bacteria Erwinia and Rhodobacter species and the fungus Neurospora crassa, and by plants including algae and cyanobacteria, respectively (Ref. 1002/1003/1004/1005). Carotene isomerase, CrtH from Synechocystis sp. PCC 6803 (cyanobacterium) (Ref. 1177/1178) and Chlorobium tepidum (green sulfur bacterium) (Ref. 1295) and CrtISO from Arabidopsis (Ref. 1179) and tomato (Ref. 1180), is involved in the synthesis of all-trans lycopene from poly-cis lycopene (Ref. 1230), and under the light condition, this process is catalyzed by light, photoisomerization. CrtI is inhibited by diphynylamine, and CrtQ/ZDS is inhibited by a herbicide J852 (Ref. 1004/1191). CrtQ is inhibited by 4-phenyl-3-(substituted benzylthio)-4H-1,2,4-triazoles in lettuse leaves (Ref. 1302). A plastid terminal oxidase (PTOX) is a cofactor of PDS and ZDS in plants, such as Arabidopsis, tomato, peper and rice (Ref. 1187/1188/1189). The first carotenoid in the normal spirilloxanthin pathway of purple photosynthetic bacteria (Ref. 1054). Rhabdochromatium marinum (purple photosynthetic bacterium) accumulates lycopene (Ref. 1119), and this may due to low activity of CrtC in the normal spirilloxanthin pathway (Ref. 1054). Lycopene is a substrate of CrtC from Rubrivivax gelatinosus and Rhodobacter capsulatus (photosynthetic bacteria) to produce rhodopin (Ref. 1255).	Genes required for the biosynthesis of lycopene from farnesyl diphosphate (FPP) were clarified in epiphytic bacteria Erwinia species for the first time in the beginning of the 1990's (Ref. 0201/1001). Lycopene is synthesized from FPP by three crt gene products, CrtE, CrtB, and CrtI (Ref. 1002/1064). [Table 0005] Nowadays, many corresponding genes are isolated from various organisms such as higher plants, cyanobacteria, fungi, and yeasts as well as bacteria, and the functions of the genes are elucidated (Ref. 0202/1002/1003/1004/1005). Phytoene is the direct substrate for the synthesis of lycopene, in the case catalyzed by phytoene desaturase (CrtI), which is derived from bacteria, fungi, and yeasts (Ref. 0206/1021). z-Carotene is the direct substrate for lycopene synthesis, in the case catalyzed by the plant-type desaturation enzyme, z-carotene desaturase (ZDS, CrtQ) (Ref. 1022/1131/1287). [Table 0004] Neurosporene is the major product of CrtI from Rubrivivax gelatinosus (purple photosynthetic bacterium) resulting in the synthesis of spheroidene, and lycopene is the minor resulting in the synthesis of spirilloxanthin (Ref. 1107). The crtI mutants by random and site-directed mutagenesis of Rhodobacter sphaeroides, which produces only neurosporene, change to prodece also lycopene (Ref. 1116).	Bond lengths, bond angles and dihedral angles determined by AM1 calculation (Ref. 1251).	[0018] / [0026] / [0054] / [0055] / [0056] / [0059] / [0060] / [0065] / [0088] / [0135] / [0201] / [0202] / [0206] / [0217] / [0227] / [0228] / [0229] / [0231] / [0409] / [0441] / [1001] / [1002] / [1003] / [1004] / [1005] / [1019] / [1020] / [1021] / [1022] / [1052] / [1054] / [1057] / [1062] / [1064] / [1107] / [1116] / [1119] / [1131] / [1132] / [1152] / [1154] / [1170] / [1177] / [1178] / [1179] / [1180] / [1187] / [1188] / [1189] / [1191] / [1197] / [1198] / [1199] / [1200] / [1201] / [1202] / [1206] / [1207] / [1210] / [1211] / [1230] / [1251] / [1255] / [1287] / [1295] / [1302]
11		meso-Zeaxanthin/ (3R,3'S)-Zeaxanthin	(3R,3'S)-b,b-Carotene-3,3'-diol	VCA0011	Masayoshi Ito		C₄₀H₅₆O₂	568.871		(3R,3'R)-Zeaxanthin, meso-zeaxanthin and (3R,3'R,6'R)-lutein are located in human macular (Ref. 1168/1169). A membrane-associated xanthophyll-binding protein, which is a Pi isoform of human glutathione S-transferase (GSTP1), is purified from hman macula. It binds (3R,3'R)-zeaxanthin and (3R,3'S-meso)-zeaxanthin, but not lutein A (Ref. 1326).	212-213 C (Ref. 0076)						lmax (nm) (e): hexane 273 (360), 403 (902), 430sh (1710), 449 (2410), 477 (2130) (Ref. 0076)	nmax(KBr)/cm^-¹: [Spectrum 0013] (Ref. 0065)	¹H-NMR d(CDCl3, 270 MHz): 1.073 (12H, s, 1,1'-gem-Me), 1.415 (2H, d, J 4, OH), 1.47 (2H, t, J 12, 2,2'ax-H), 1.738 (6H, s, 5,5'-Me), 1.765 (2H, dt, J 12, 2.5, 2,2'eq-H), 1.972 (12H, s, 9',9',13,13'-Me), 2.035 (2H, dd, J 17, 9.5, 4,4'ax-H), 2.385 (2H, dd, J 17, 5.5, 4,4'eq-H), 3.98 (2H, m, 3,3'-H), 6.117 (4H, s, 7,7',8,8'-H), 6.155 (2H, d, J 11, 10, 10,10'-H), 6.255 (2H, d, J 9, 14,14'-H), 6.360 (2H, d, J 15, 12,12'-H), 6.55-6.74 (4H, m, 11,11',15,15'-H) (Ref. 0076)	m/z: 568 (M, 100%), 550 (M-18, 84%), 532 (M-18-18, 5%), 489 (M-79, 1%), 476 (M-92, 13%), 462 (M-106, 1%), 458 (M-18-92, 11%), 444 (M-18-106, 1%), 410 (M-158, 5%) (Ref. 0058)	CD data in EPA solution (25C): no optical activity (Ref. 0405)	HPLC column: Spherisorb S5W 0.3150 cm, eluent: hexane-CH2Cl2-isopropyl alcohol-Hünig's base (90.9:6.5:2.5:0.1) [Chromatogram 0008] --- (3R,3'R)-zeaxanthin (Ref. 0048) HPLC columun: Sumipax OA-2000 (5mm) 0.830 cmeluent: hexane-CH2Cl2-EtOH 90:10:0.1, flow: 1.5 ml/min tR = ca. 40 min (meso)-zeaxamthin, ca. 45 min (3R,3'R), ca. 50 min (3S3'S) [Chromatogram 0009] (Ref. 0069/0405)	Shrimp (Paratya compressa compressa) (Ref. 0405) Fish (Oncorhynchus keta, Seriola quinqueraduata, Micropterus salmoides, Tilapia nilotica, Stephanolepis cirrhifer, Salmo gairdneri) (Ref. 0405) Fish (Salmo salar, Salmo gairdneri) (Ref. 0406/0407) Human macular (Ref. 1168/1169).	(R)- and (S)-3-Hydroxy-b-cycloitrals prepared by hydroboration of safranol isopropenylether with (+)- and (-)-diisopinocampenylborane were transformed into (3R,3'R)-, (3S,3'S)- and (3R,3'S: meso)-zeaxanthin, via the Wittig condensation of the corresponding C15-phosphonium salt with the C10-dialdehyde. (Ref. 0019/0076)			Semi-empirical molecular orbital calculations using AM1 Hamiltonian (MNDO-AM1 method) were performed in order to predict their stable structures (Ref. 1337).	[0019] / [0048] / [0058] / [0065] / [0069] / [0076] / [0405] / [0406] / [0407] / [1168] / [1169] / [1326] / [1337]
12		(3S,3'S)-Zeaxanthin	(3S,3'S)-b,b-Carotene-3,3'-diol	VCA0012	Masayoshi Ito		C₄₀H₅₆O₂	568.871			209-209.5C (Ref. 0076)						lmax (nm) (e): hexane 275 (404), 407sh (932), 432sh (1745), 453 (2500), 481 (2205) (Ref. 0076)	nmax(KBr)/cm^-¹: [Spectrum 0013] (Ref. 0065)	¹H-NMR d(CDCl3, 270 MHz): 1.073 (12H, s, 1,1'-gem-Me), 1.415 (2H, d, J 4, OH), 1.47 (2H, t, J 12, 2,2'ax-H), 1.738 (6H, s, 5,5'-Me), 1.765 (2H, dt, J 12, 2.5, 2,2'eq-H), 1.972 (12H, s, 9',9',13,13'-Me), 2.035 (2H, dd, J 17, 9.5, 4,4'ax-H), 2.385 (2H, dd, J 17, 5.5, 4,4'eq-H), 3.98 (2H, m, 3,3'-H), 6.117 (4H, s, 7,7',8,8'-H), 6.155 (2H, d, J 11, 10, 10,10'-H), 6.255 (2H, d, J 9, 14,14'-H), 6.360 (2H, d, J 15, 12,12'-H), 6.55-6.74 (4H, m, 11,11',15,15'-H) (Ref. 0076)	m/z: 568 (M, 100%), 550 (M-18, 84%), 532 (M-18-18, 5%), 489 (M-79, 1%), 476 (M-92, 13%), 462 (M-106, 1%), 458 (M-18-92, 11%), 444 (M-18-106, 1%), 410 (M-158, 5%) (Ref. 0058)	CD data: 225 (+9.72), 251 (-9.38), 289 (+13.65), 347 (-3.99) (Ref. 0076) CD data in EPA solution (25C): De 224 (+18.0), 236 (0), 245 (-18.0), 260 (0), 284 (+24.0), 325 (0), 350 (-4.0), 380 (-0.5) (Ref. 0405)	HPLC column: Spherisorb S5W 0.3150 cm, eluent: hexane-CH2Cl2-isopropyl alcohol-Hünig's base (90.9:6.5:2.5:0.1) [Chromatogram 0008] --- (3R,3'R)-zeaxanthin (Ref. 0048) HPLC columun: Sumipax OA-2000 (5mm) 0.830 cmeluent: hexane-CH2Cl2-EtOH 90:10:0.1, flow: 1.5 ml/min tR = ca. 40 min (meso)-zeaxamthin, ca. 45 min (3R,3'R), ca. 50 min (3S3'S) [Chromatogram 0009] (Ref. 0069/0405)	Shrimp (Paratya compressa compressa) (Ref. 0405) Fish (Oncorhynchus keta, Seriola quinqueraduata, Micropterus salmoides, Tilapia nilotica, Stephanolepis cirrhifer, Salmo gairdneri) (Ref. 0405) Fish (Salmo salar, Salmo gairdneri) (Ref. 0406/0407)	(R)- and (S)-3-Hydroxy-b-cycloitrals prepared by hydroboration of safranol isopropenylether with (+)- and (-)-diisopinocampenylborane were transformed into (3R,3'R)-, (3S,3'S)- and (3R,3'S: meso)-zeaxanthin, via the Wittig condensation of the corresponding C15-phosphonium salt with the C10-dialdehyde. (Ref. 0019/0076)			Semi-empirical molecular orbital calculations using AM1 Hamiltonian (MNDO-AM1 method) were performed in order to predict their stable structures (Ref. 1337).	[0019] / [0048] / [0058] / [0065] / [0069] / [0076] / [0405] / [0406] / [0407] / [1337]
13		Astaxanthin glucoside	(3S,3'S)-3-(b-D-Glucopyranosyloxy)-3'-hydroxy-b,b-carotene-4,4'-dione	VCA0013	Masayoshi Ito		C₄₆H₆₂O₉	758.979									lmax (nm): benzene 487 (Ref. 0085)		¹H-NMR d(CDCl3): 2.04 (t, J 14, 2-H), 2.15 (dd, J 14, 6, 2-H), 4.40 (dd, J 14, 6, 3-H), 1.23 and 1.35 (s, 1-gem-Me), 1.91 (s, 5-Me), 1.81 (t, J 13, 2'-H), 2.16 (dd, J 13, 6, 2'-H), 4.32 (ddd, 13, 6, 2, 3'-H), 1.21 and 1.32 (s, 1'-gem-Me), 1.94 (s, 5'-Me), 1.99-2.01 (s, 19,19',20,20'-Me), 6.20-6.70 (14H, m, olefinic-H), 4.57 (d, J 8, 1''-H), 3.45 (dd, J 9, 8, 2''-H), 3.61 (m, 3''-H), 3.61 (m, 4''-H), 3.41 (m, 5''-H), 3.83 and 3.93 (m, 6''-H₂) (Ref. 0085) ¹³C-NMR d(CDCl3): 37.4 (1), 44.7 (2), 77.6 (3), 199.3 (4), 127.9 (5), 162.4 (6), 123.0 (7), 142.7 (8), 134.4 (9), 135.5 (10), 124.5 (11), 140.0 (12), 136.8 (13), 134.0 (14), 130.6 (15), 26.6 and 30.6 (1-gem-Me), 14.1 (5-Me), 12.59 (9-Me), 12.84 (13-Me), 36.8 (1'), 45.5 (2'), 69.2 (3'), 200.4 (4'), 126.9 (5'), 162.2 (6'), 123.3 (7'), 142.3 (8'), 134.6 (9'), 135.1 (10'), 124.7 (11'), 139.7 (12'), 136.7 (13'), 133.8 (14'), 130.8 (15'), 26.2 and 30.8 (1'-gem-Me), 14.0 (5'-Me), 12.58 (9'-Me), 12.83 (13'-Me), 104.9 (1''), 74.3 (2''), 77.2 (3''), 70.3 (4''), 75.7 (5''), 62.7 (6'') (Ref. 0085)	HRFABMS m/z: 759.4474 [M+H]⁺ (Ref. 0085)	CD data: De 242 (-12.0), 274 (+10.1), 314 (-18.5) (Ref. 0085)	HPLC (columun: TSK gel ODS-80Ts (Tosoh) 0.4615 cm, eluent and flow: 1.0 ml/min, H2O-MeOH 5:95 for 5 min, then 5 min-linear gradient MeOH-THF 7:3) tR = 3.92 min [Chromatogram 0011] (Ref. 0085)	Agrobacterium aurantiacum (marine bacterium; present name, Paracoccus sp. N81106) (Ref. 0085) It has recently been shown that this bacterium belongs to Paracoccus species according to their16S rDNA analysis, performed by T. Hamada of Marine Biotechnology Institute (DDBJ accession number: AB008114).			Escherichia coli, which carries the Erwinia crtE, crtB, crtI, crtY, crtZ, and crtX genes and the crtW gene of Agrobacterium aurantiacum, accumulates astaxanthin-b-glucoside in addition to astaxanthin-b-D-diglucoside of the final product (Ref. 1027).		[0085] / [1027]
14		Adonixanthin/ 4-Ketozeaxanthin	(3S,3'R)-3,3'-Dihydroxy-b,b-caroten-4-one	VCA0014	Masayoshi Ito		C₄₀H₅₄O₃	582.855			(3R,3'R)-Isomer: 180-181C; (3R,3'S)-isomer: 181.5-182.5C; (3S,3'R)-isomer: 180-181C (Ref. 0077>						lmax (nm) (e): CHCl3 304 (16695), 480 (105444) (Ref. 0077); hexane 297 (18116), 459 (118149) (Ref. 0077); benzene 472 (116980) (Ref. 0077); ethanol 299 (16252), 465 (108660) (Ref. 0077)	nmax/cm^-¹:3433s (OH), 1658s (conj. CO), 1557m, 1516m (conj. C=C), 1074m, 1038m (sek. OH), 964s (trans CH=CH) (Ref. 0077)	¹H-NMR d(270 MHz, CDCl3): 1.075 (s, 1'-gem-Me), 1.213 (s, 1eq-Me), 1.322 (s, 1ax-Me), 1.48 (t, J 12, 2'ax-H), 1.738 (s, 5'-Me), 1.774 (m, 2'eq-H), 1.810 (t, J 13.5, 2ax-H), 1.948 (d, J 0.8, 5-Me), 1.974 (s, 9'-Me), ca. 1.983 (s, 13-, 13'-Me), 1.998 (s, 9-Me), 2.045 (dd, J 17.5, 10, 4'ax-H), 2.16 (dd, J 12.5, 5.5, 2eq-H), 2.39 (dd, J 17.5, 5, 4'eq-H), 3.704 (d, J 1.8, 3-OH), ca. 4.0 (br m, 3'ax-H), 4.33 (ddd, J 14, 6, 1.8, 3ax-H), ca. 6.13 (s, 7'-, 8'-H), 6.16 (d, J 11.5, 10'-H), 6.21 (d, J 16, 7-H), ca. 6.24-6.33 (m, 14-, 14'-, 10-H), 6.37 (d, J 15, 12'-H), 6.44 (d, J 16, 8-H), 6.45 (d, J 15, 12-H), ca. 6.65 (m, 11-, 11'-, 15-, 15'-H) (Ref. 0077) ¹³C-NMR d(100.6 MHz, CDCl3): 12.55 (9-Me), 12.76, 12.78, 12.85 (13-, 9'-13'-Me), 14.0 (5-Me), 21.62 (5'-Me), 26.14, 30.73 (1-gem-Me), 28.72 (1'ax-Me), 30.25 (1'eq-Me), 36.79 (C1), 37.11 (C1'), 42.54 (C4'), 45.38 (C2), 48.39 (C2'), 65.02 (C3'), 69.20 (C3), 123.11 (C7), 124.26 (C11), 125.26 (C11'), 125.75 (C7'), 126.23 (C5'), 126.72 (C5), 129.80, 130.94 (C15, C15'), 131.22 (C10'), 132.42 (C14'), 134.01 (C14), 134.29 (C9), 135.29 (C10), 135.94 (C9'), 136.07, 137.10 (C13, C13'), 137.42 (C12'), 137.71 (C6'), 138.42 (C8'), 139.86 (C12), 142.43 (C8), 162.27 (C6), 200.40 (C4) (Ref. 0077)	m/z (ion, intensity relative to base peak in %): 566 (M, 31), 564 (9), 548 (5), 474 (4), 412 (6), 203 (62), 159 (50), 145 (45), 119 (74), 105 (81), 91 (100), 69 (68), 55 (68), 41 (67) (Ref. 0077)	CD data in EPA solution De: (3R,3'S)-isomer: 363 (-2.94), 307 (20.75), 290sh (11.38), 264 (-12.43) , 238 (10.43); (3R,3'R)-isomer: 369 (3.74), 307 (4.68), 293sh (2.66), 285sh (1.26) , 263 (-2.50), 246 (-0.63); (3S,3'R)-isomer: 366 (2.40), 307 (-18.95), 292sh (-11.64), 264 (11.12) , 238 (-9.85); (3S,3'S)-isomer: 371 (-3.83), 329 (-0.29), 307 (-4.87), 293sh (-2.95) , 283sh (-1.32), 264 (1.71), 243 (-0.21) (Ref. 0064/0077/0078)	HPLC (columun: TSK gel ODS-80Ts (Tosoh) 0.4615 cm, eluent and flow: 1.0 ml/min, H2O-MeOH 5:95 for 5 min, then 5 min-linear gradient MeOH-THF 7:3) tR = 8.37 min [Chromatogram 0012] (Ref. 0085) HPLC (columun: TSK gel ODS-80Ts (Tosoh) 0.4615 cm, eluent and flow: 1.0 ml/min, H2O-MeOH 5:95 for 5 min, follwed by 5 min-linear gradient MeOH-THF 7:3, and then MeOH-THF 7:3 for 5 min) b-carotene, echinenone, b-cryptoxanthin, 3-hydroxy-echinenone, cantaxanthin, 3'-hydroxy-echinenone, cis-adonixanthin, adonirubin, adonixanthin and astaxanthin were separated. tR = 8.32 min for adnixanthin (Ref. 0208)	Adonis annua (flower petals of higher plant) (Ref. 0412) Pannulis japonicus (Spiny Lobster) (Ref. 0413) Carassius auratus (Gold fish) as b-doradexanthin (Ref. 0412/0415) Agrobacterium aurantiacum, Alcaligenes sp. strain PC-1 (marine bacteria; present name, Paracoccus sp. N81106 and MBIC03024, respectively) (Ref. 0068/0085) It has recently been shown that these marine bacteria belong to Paracoccus species according to their16S rDNA analysis, performed by T. Hamada of Marine Biotechnology Institute (DDBJ accession number: AB008114). Brevundimonas sp. SD212 (bacterium) (Ref. 1343)	The Wittig condensation of the enantiomeric C25-apocarotenal with the enantiomeric C15-phosphonium salt by use of NaOMe as base provided (3R,3'R)-, (3R,3'S)-, (3S, 3'R)-, (3S, 3'S)-adnixanthin in ca. 45 % yield. (Ref. 0077)		Escherichia coli, which carries the Erwinia crtE, crtB, crtI, and crtY genes and the crtZ and crtW genes derived from Erwinia species or Agrobacterium aurantiacum, accumulates adonixanthin as one of intermediary metabolites in addition to astaxanthin of the final product (Ref. 0202).		[0064] / [0068] / [0077] / [0078] / [0085] / [0202] / [0208] / [0412] / [0413] / [0415] / [1343]
15		Adonixanthin 3-glucoside/ Adonixanthin 3-b-D-glucoside	(3S,3'R)-3-(b-D-Glucopyranosyloxy)-3'-hydroxy-b,b-caroten-4-one	VCA0015	Masayoshi Ito		C₄₆H₆₄O₈	744.996									lmax (nm): benzene 476 (Ref. 0085)		¹H-NMR d(CDCl3): 2.04 (m, 2-H), 2.15 (dd, J 14, 6, 2-H), 4.40 (dd, J 14, 6, 3-H), 1.23 and 1.35 (s, 1-gem-Me), 1.91 (s, 5-Me), 1.48 (t, J 12, 2'-H), 1.77 (ddd, J 12, 4, 2, 2'-H), 4.00 (m, 3'-H), 2.05 (m, 4'-H), 2.39 (ddd, J 17, 6, 2, 4'-H), 1.08 (s, 1'-gem-Me), 1.74 (s, 5'-Me), 1.98-2.00 (s, 19,19',20,20'-Me), 6.10-6.70 (14H, m, olefinic-H), 4.57 (d, J 8, 1''-H), 3.45 (dd, J 9, 8, 2''-H), 3.61 (m, 3''-H), 3.61 (m, 4''-H), 3.41 (m, 5''-H), 3.83 and 3.93 (m, 6''-H₂) (Ref. 0085)	HRFABMS m/z: 745.4689 [M+H]⁺ (Ref. 0085)	CD data: De 234 (-14.2), 260 (+17.4), 301 (-21.4) (Ref. 0085)	HPLC (columun: TSK gel ODS-80Ts (Tosoh) 0.4615 cm, eluent and flow: 1.0 ml/min, H2O-MeOH 5:95 for 5 min, then 5 min-linear gradient MeOH-THF 7:3) tR = 4.84 min [Chromatogram 0012] (Ref. 0085)	Marine bacterium ---Agrobacterium aurantiacum (Rhizobiaceae; present name, Paracoccus sp. N81106) (Ref. 0085)					[0085]
16		Lutein/ Lutein A	(3R,3'R,6'R)-b,e-Carotene-3,3'-diol	VCA0016	Masayoshi Ito		C₄₀H₅₆O₂	568.871		Inhibitotory effect on Epstein-Barr virus activation (anti-tumor promotion) (Ref. 0217). Inhibitory effect on colonic aberrant crypt foci formation (anti-tumor promotion) (Ref. 0229). Singlet oxygen quenching activity (Ref. 0088/0230/0441). Scavenging effect against free radical (Ref. 0215). Lycopene and lutein showed the anti-tumor promoting activities in mouse two-stage skin carcinogenesis and decreased the number of aberrant crypt foci in rat colon (Ref. 1205). Fucoxanthin, lycopene and lutein decreased the number of aberrant crypt foci in colons in mice (Ref. 1206). Lutein and b-cryptoxanthin suppressed tumorigenesis in skin and colon in mice (Ref. 1208). A carotenoid binding protein is isolated from silk glands of Bombyx mori larvae. The Y (yellow hemolymph) gene (AF309498) encods this 33 kDa protein, and one lutein bonds (Ref. 1183). Typical lutein and zeaxanthin levels in the human eye (Ref. 1301). (3R,3'R)-Zeaxanthin, meso-zeaxanthin and (3R,3'R,6'R)-lutein are located in human macular (Ref. 1168/1169). A membrane-associated xanthophyll-binding protein, which is a Pi isoform of human glutathione S-transferase (GSTP1), is purified from hman macula. It binds (3R,3'R)-zeaxanthin and (3R,3'S-meso)-zeaxanthin, but not lutein A (Ref. 1326). Crystal structure of spinach major light-harvesting complex (LHCII) contains 2 lutein, 1 9'-cis neoxanthin, 1 (violaxanthin, antheraxanthin or zeaxanthin), 8 chlorophyll a, and 6 chlorophyll b per monomer (Ref. 1291).	183-185C (Ref. 0086) 174-178C (Ref. 1078)						lmax (nm) (e): dioxane 429 (1680), 453 (2515), 482 (2259) (Ref. 0086); methanol 330, 422 (shoulder), 443, 470, %III/II=61.7 [Spectrum 1108] (Ref. 1052)		¹H-NMR d(270 MHz, CDCl3): 0.849, 0.998 (6H, s, 1'-gem-Me), 1.074 (6H, s, 1-gem-Me), 1.37 (1H, dd, J 13, 7, 2'ax-H), 1.48 (1H, t, J 12, 2ax-H), 1.626 (3H, s, 5'-Me), 1.739 (3H, s, 5-Me), 1.84 (1H, dd, J 13, 6, 2'eq-H), 1.912 (3H, s, 9'-Me), 1.970 (9H, s, 9-, 13-, 13'-Me), 2.04 (1H, dd, J 17, 10, 4ax-H), ca. 2.33-2.45 (2H, m, 6'-, 4eq-H), ca. 4.0 (1H, m, 3-H), 4.25 (1H, 3'-H), 5.43 (1H, dd, J 15.5, 10, 7'-H), 5.55 (1H, s, 4'-H), ca. 6.12 (2H, s, 7-, 8-H), ca. 6.15 (3H, m, 8'-, 10-, 10'-H), ca. 6.26 (2H, m, 14-, 14'-H), 6.36 (2H, d, J 15, 12-, 12'-H), ca. 6.55-6.71 (4H, m, 11-, 11'-, 15-, 15'-H) (Ref. 0086/0128/1080) ¹³C-NMR d(CDCl3): 37.1 (C1), 48.4 (C2), 65.1 (C3), 42.5 (C4), 126.2 (C5), 137.6 (C6), 125.6 (C7), 138.5 (C8), 135.6 (C9), 131.3 (C10), 124.9 (C11), 137.6 (C12), 136.5 (C13), 132.6 (C14), 130.0 (C15), 28.7, 30.2 (1-gem-Me), 21.6 (5-Me), 12.7 (9-Me), 12.7 (13-Me), 34.0 (C1'), 44.7 (C2'), 65.9 (C3'), 125.6 (C4'), 137.8 (C5'), 55.0 (C6'), 128.6 (C7'), 137.8 (C8'), 135.0 (C9'), 130.8 (C10'), 124.5 (C11'), 137.6 (C12'), 136.5 (C13'), 132.6 (C14'), 130.0 (C15'), 24.3, 29.5 (1'-gem-Me), 22.8 (5'-Me), 13.2 (9'-Me), 12.7 (13'-Me) (Ref. 0061).	(Ref. 0059)	CD: 247.5 (+6.33), 288 (-2.39) (Ref. 0086) CD data in EPA solution (25C): De 220 (+2.0), 245 (+8.0), 275 (0), 284 (-4.5), 370 (-0.5) (Ref. 0117/0116)	RF-TLC on 0.25 mm RP-18 layers (Merck, Art. 15423) using several ratio of light petroleum (bp 40-60C)-acetonitrile-methanol ex: 1:6:3 Rf=0.30, 3:1:6 Rf=0.63 (Ref. 0135) A reversed-phase HPLC procedure for quantitative measurement in serum of seven carotenoids (lutein, zeaxanthin, canthaxanthin, b-cryptoxanthin, lycopenes, a-c arotene and b-carotene) has been developed. (Ref. 0227) Retinol, a-tocoherol, lutein, all-trans-lycopene, and a- and b-carotenes were determined in human plasma by reversed-phase HPLC. (Ref. 0228) HPLC (column: Spherisorb 5S, eluent: hexane-CH2Cl2-2-Propanol-NEt(iso-Pr)2 90.9:6.5:2.5:0.1) (Ref. 0128) Separation of zeaxanthin and lutein by Novapak C₁₈ HPLC column (8 100 mm, RCM-type, Waters) (Ref. 1150) and by Spherisorb ODS-1 HPLC column (4.6 250 mm) (Ref. 1151).	Algae (Chlorophyta) (Ref. 0409) Fruits, flowers, leaves, seeds of higher plant (Ref. 0409) Birds, birds' egg yolk, fish, fish eggs, shellfish, insect, reptiles (Ref. 0410) Parnus major (bird) (Ref. 0429) Lutein is the major carotenoid in the yellow facial skin of Egyptian vulture (bird), which includes ungulate faeces in its diet for cosmetic purposes (Ref. 1184).	Reaction of (S)-4-hydroxy-2,6,6-trimethylcyclohex-2-en-1-one with mesyl chloride followed by treatment with tetrabutylammonium acetate gave the acetoxyketone with complete inversion of configuration, which was readily transformed into the protected (R)-4-hydroxy-2,6,6-trimethylcyclohex-2-en-1-one. Diastereoselective epoxidation of this protected hydroxyketone with dimethyl sulphonium methylide followed by stereoselective opening of the epoxide with Grignard reagent gave the protected hydroxy-a-cyclocitral. This was converted into the C15-phosphonium chloride, which was condensed with C25-apocarotenal by use of KOH as base to give (3R,3'R,6'R)-lutein in 25% yield referred to apocarotenal. (Ref. 0014/0019/0086)	Carassius auratus (gold fish): Lutein 3'-epilutein a-carotene-3,4,3'-triol a-doradexanthin (Ref. 0415) Hen's egg yolk: Lutein e,e-carotene-3,3'-dione (Ref. 0427/0428) Tilapia (Tilapia nilotica): Lutein tunaxanthin (Ref. 0417) Lutein 3,4-didehydroretinol (Ref. 0417/0217) [Table 1028]	From a-carotene, b-carotene hydroxylase (CrtR-b) and e-carotene hydroxylase (LUT1, CrtR-e) produce lutein A (Ref. 1280>.		[0014] / [0019] / [0059] / [0061] / [0086] / [0088] / [0116] / [0117] / [0128] / [0135] / [0215] / [0217] / [0227] / [0228] / [0229] / [0230] / [0409] / [0410] / [0415] / [0417] / [0427] / [0428] / [0429] / [0441] / [1052] / [1078] / [1080] / [1150] / [1151] / [1168] / [1169] / [1183] / [1184] / [1205] / [1206] / [1208] / [1280] / [1291] / [1301] / [1326]
17		(3R,3'R)-Astaxanthin	(3R,3'R)-3,3'-Dihydroxy-b,b-carotene-4,4'-dione	VCA0017	Masayoshi Ito		C₄₀H₅₂O₄	596.838		Antioxidant activity (Ref. 0092/0093/0215) Singlet oxygen quenching activity (Ref. 0088/0230/0441) Immunomodulating action (Ref. 0213) Chemoprevention of carcinogenesis (Ref. 0218/0219)							lmax (nm) (e): CHCl 3492 (1920) (Ref. 0010/0077)	nmax(KBr)/cm^-¹: 3486m (OH), 1664s (conj. CO), 1607m, 1557s (C=C), 1399w, 1390m, 1366w (gem. Dimetyl), 1076s, 1039m (OH) and 969s (CH=CH, trans) [Spectrum 0003] (Ref. 0010/0077)	¹H-NMR d(500 MHz, CDCl3): 1.21 and 1.32 (each 6H, s, 1, 1'-gem-Me), 1.81 (2H, t, J 13, 2, 2'-Hax), 1.94 (6H, s, 5, 5'-Me), 1.98 and 2.00 (each 6H, s, 9, 9', 13, 13'-Me), 2.16 (2H, dd, J 6 and 13, 2, 2'-Heq), 3.67 (2H, d, J 2, 3, 3'-OH), 4.32 (2H, ddd, J 2, 6 and13, 3, 3'-H) and 6.20-6.70 (14H, m, olefinic-H) (Ref. 0068/0077)	m/z: 596 (M), (M-16), (M-16-16), (M-79), (M-92), (M-106), (M-92-16), (M-106-16), (M-154), (M-167), (M-207), (M-219), (M-233) (Ref. 0058/0077)	CD data in EPA solution (25C): De 240 (+20.0), 252 (0), 270 (-20.0), 284 (0), 314 (+34.0), 355 (0), 372 (-3.0) (Ref. 0421)	TLC (Kieselgel 60 Merck, CH2Cl2-acetone-formic acid 95:5:3) Rf = 0.3 --- (3S,3'S)-astaxanthin (Ref. 0010) HPLC (column: Sumipax OA-2000 (10mm) 0.425 cm, eluent: hexane-CH2Cl2-EtOH 48:16:0.6, flow: 0.8 ml/min) tR = ca. 57 min (3R,3'R), ca. 60 min (meso), ca. 64 min (3S,3'S) [Chromatogram 0004] (Ref. 0069/0070/0210) HPLC (column: LiChrosorb SI 60 (5 mm) 0.3250 cm, eluent: hexane-ethyl acetate-acetonitrile 88:10:2, flow: 0.8 ml/min) tR = ca. 42 min (diacetate of all-E isomer) [Chromatogram 0005] --- racemic astaxanthin (Ref. 0071) HPLC (columun: TSK gel ODS-80Ts (Tosoh) 0.4615 cm, eluent and flow: 1.0 ml/min, H2O-MeOH 5:95 for 5 min, follwed by 5 min-linear gradient MeOH-THF 7:3, and then MeOH-THF 7:3 for 5 min) b-carotene, echinenone, b-cryptoxanthin, 3-hydroxy-echinenone, cantaxanthin, 3'-hydroxy-echinenone, cis-adonixanthin, adonirubin, adonixanthin and astaxanthin were separated. tR = 6.30 min for astaxanthin (Ref. 0208). Separation of (3S,3'S), (3S,3'R) and (3R,3'R) astaxanthin by HPLC on a Pirkle covalent L-leucine column (Ref. 1164).	Phaffia rhodozyma (Xanthophyllomyces dendrorhous) (yeast) (Ref. 0425) Homarus gammarus (Lobster) (Ref. 0418) Salmo salar, Oncorhynchus (salmon) (Ref. 0419) Asterias rubens (starfish) (Ref. 0420) Shrimps and lobsters (Ref. 0421) Euphausia superba (antarctic krill) (Ref. 0422) Asterina pectinifera, Asterias amurensis (starfish) (Ref. 0423) Watasenia scintilans, Sepia modokai, Sepia officinales (cuttlefish) (Ref. 0424) Octopus vulgaris, Octopus ocellatus, Octopus minor (octopus) (Ref. 0424)	The Wittig condensation of C10-dialdehyde with 2 equiv. of C15-phosphonium salt and subsequent thermal isomerization afforded astaxanthin. (3S,3'S)- and (3R,3'R)-Astaxanthin --- Enantiomeric chiral blocks of C15-phosphonium salts were synthesized via three different routes. (Ref. 0012/0016) (3S,3'S)- and (3R,3'R)-Astaxanthin --- C15-Phosphonium salts were prepared from enantiomeric 3-acetoxy-4-oxo-b-ionones obtained by separation of the corresponding diastereomeric camphanates and by microbial resolution. (Ref. 0015/0073)	Only Phaffia rhodozyma (Xanthophyllomyces dendrorhous) (yeast) synthesizes (3R,3'R)-astaxanthin, while other organisms, such as bacteria and green algae, synthesize (3S,3'S)-form (Ref. 0425). b-Ionone, an end ring analog of b-carotene, inhibits astaxanthin synthesis from b-carotene in the Phaffia rhodozyma (Ref. 1267).		Almost the same stereochemical composition in astaxanthin, its monoester and its diester in krill are found: 62-71% (3R,3'R)-, 11-14% (3R,3'S; meso)- and 17-26% (3S,3'S)-astaxanthin (Ref. 0422). Those in Euphausia, Thysanoessa, Calanus, Acanthephyra and Cancer (Crustaceans) are also reported (Ref. 1257). Semi-empirical molecular orbital calculations using AM1 Hamiltonian (MNDO-AM1 method) were performed in order to predict their stable structures (Ref. 1337).	[0010] / [0012] / [0015] / [0016] / [0058] / [0068] / [0069] / [0070] / [0071] / [0073] / [0077] / [0088] / [0092] / [0093] / [0208] / [0213] / [0215] / [0218] / [0219] / [0230] / [0418] / [0419] / [0420] / [0421] / [0422] / [0423] / [0424] / [0425] / [0441] / [1164] / [1257] / [1267] / [1337]
18		meso-Astaxanthin/ (3R,3'S)-Astaxanthin	(3R,3'S)-3,3'-Dihydroxy-b,b-carotene-4,4'-dione	VCA0018	Masayoshi Ito		C₄₀H₅₂O₄	596.838		Antioxidant activity (Ref. 0092/0093/0215) Singlet oxygen quenching activity (Ref. 0088/0230/0441) Immunomodulating action (Ref. 0213) Chemoprevention of carcinogenesis (Ref. 0218/0219)	222-223C (Ref. 0077)						lmax (nm) (e): CHCl3 300 (17634), 490 (116386) (Ref. 0010/0077); hexane 294 (16946), 471 (126163) (Ref. 0077); benzene 485 (112876) (Ref. 0077); ethanol 250 (14002), 297 (15578), 471 (116570) (Ref. 0077)	nmax(KBr)/cm^-¹: 3486m (OH), 1664s (conj. CO), 1607m, 1557s (C=C), 1399w, 1390m, 1366w (gem. Dimetyl), 1076s, 1039m (OH) and 969s (CH=CH, trans) [Spectrum 0003] (Ref. 0010/0077)	¹H-NMR d(500 MHz, CDCl3): 1.21 and 1.32 (each 6H, s, 1, 1'-gem-Me), 1.81 (2H, t, J 13, 2, 2'-Hax), 1.94 (6H, s, 5, 5'-Me), 1.98 and 2.00 (each 6H, s, 9, 9', 13, 13'-Me), 2.16 (2H, dd, J 6 and 13, 2, 2'-Heq), 3.67 (2H, d, J 2, 3, 3'-OH), 4.32 (2H, ddd, J 2, 6 and13, 3, 3'-H) and 6.20-6.70 (14H, m, olefinic-H) (Ref. 0068/0077)	m/z: 596 (M), (M-16), (M-16-16), (M-79), (M-92), (M-106), (M-92-16), (M-106-16), (M-154), (M-167), (M-207), (M-219), (M-233) (Ref. 0058/0077)	CD data in EPA solution (25C): no optical activity (Ref. 0421)	TLC (Kieselgel 60 Merck, CH2Cl2-acetone-formic acid 95:5:3) Rf = 0.3 --- (3S,3'S)-astaxanthin (Ref. 0010) HPLC (column: Sumipax OA-2000 (10mm) 0.425 cm, eluent: hexane-CH2Cl2-EtOH 48:16:0.6, flow: 0.8 ml/min) tR = ca. 57 min (3R,3'R), ca. 60 min (meso), ca. 64 min (3S,3'S) [Chromatogram 0004] (Ref. 0032/0069/0070/0210) HPLC (column: LiChrosorb SI 60 (5 mm) 0.3250 cm, eluent: hexane-ethyl acetate-acetonitrile 88:10:2, flow: 0.8 ml/min) tR = ca. 42 min (diacetate of all-E isomer) [Chromatogram 0005] --- racemic astaxanthin (Ref. 0071) HPLC (columun: TSK gel ODS-80Ts (Tosoh) 0.4615 cm, eluent and flow: 1.0 ml/min, H2O-MeOH 5:95 for 5 min, follwed by 5 min-linear gradient MeOH-THF 7:3, and then MeOH-THF 7:3 for 5 min) b-carotene, echinenone, b-cryptoxanthin, 3-hydroxy-echinenone, cantaxanthin, 3'-hydroxy-echinenone, cis-adonixanthin, adonirubin, adonixanthin and astaxanthin were separated. tR = 6.30 min for astaxanthin (Ref. 0208). Separation of (3S,3'S), (3S,3'R) and (3R,3'R) astaxanthin by HPLC on a Pirkle covalent L-leucine column (Ref. 1164).	Homarus gammarus (Lobster) (Ref. 0418) Salmo salar, Oncorhynchus (salmon) (Ref. 0419) Asterias rubens (starfish) (Ref. 0420) Shrimps and lobsters (Ref. 0421) Euphausia superba (antarctic krill) (Ref. 0422) Asterina pectinifera, Asterias amurensis (starfish) (Ref. 0423) Watasenia scintilans, Sepia modokai, Sepia officinales (cuttlefish) (Ref. 0424) Octopus vulgaris, Octopus ocellatus, Octopus minor (octopus) (Ref. 0424)	The Wittig condensation of (R)-apoastaxanthinal (C25) with (S)-C15-phosphonium chloride in 1,2-epoxybutane provided meso-astaxanthin in 50-55% yield. (Ref. 0077)			Almost the same stereochemical composition in astaxanthin, its monoester and its diester in krill are found: 62-71% (3R,3'R)-, 11-14% (3R,3'S; meso)- and 17-26% (3S,3'S)-astaxanthin (Ref. 0422). Those in Euphausia, Thysanoessa, Calanus, Acanthephyra and Cancer (Crustaceans) are also reported (Ref. 1257). Semi-empirical molecular orbital calculations using AM1 Hamiltonian (MNDO-AM1 method) were performed in order to predict their stable structures (Ref. 1337).	[0010] / [0032] / [0058] / [0068] / [0069] / [0070] / [0071] / [0077] / [0088] / [0092] / [0093] / [0208] / [0213] / [0215] / [0218] / [0219] / [0230] / [0418] / [0419] / [0420] / [0421] / [0422] / [0423] / [0424] / [0441] / [1164] / [1257] / [1337]
19		3,4-Didehydro-b-carotene	3,4-Didehydro-b,b-carotene	VCA0019	Masayoshi Ito		C₄₀H₅₈	538.889			186C (Ref. 0087)						lmax (nm): petrol 461 (E ¹^%₁_c_m = 2330) (Ref. 0087)							10-(2,6,6-Trimethylcyclohexen-1-yl)-4,8-dimethyl-4,6,8-decatrien-2-yn-3-ol was treated with ethyl magnesium bromide, and then reacted with the C19-dialdehyde to give the corresponding C40-acetylenic diol. Subsequent dehydration, Lindlar hydrogenation and isomerisation gave 3,4-detrahydro-b-carotene. (Ref. 0087)				[0087]
20		3,4,3',4'-Bisdehydro-b-carotene/ Bisdehydro-b-carotene/ Tetradehydro-b-carotene	3,4,3',4'-Tetradehydro-b,b-carotene	VCA0020	Masayoshi Ito		C₄₀H₆₀	540.904			190-191C (Ref. 0087)						lmax (nm): petrol 471 (E ¹^%₁_c_m = 2400) (Ref. 0087)							The di-Grignard reagent of acetylene was reacted with 2 equivalents of the 3,4-dehydro-C19-aldehyde to give the corresponding C40-acetylenic diol, from which 3,4,3',4'-tetradehydro-b-carotene was obtained by dehydration, Lindlar hydrogenation, and isomerisation. (Ref. 0087)				[0087]
21		Eschscholtzxanthin	(3S,3'S)-4',5',-Didehydro-4,5'-retro-b,b-carotene-3,3'-diol	VCA0021	Masayoshi Ito		C₄₂H₅₄O₂	590.877		Antioxidative activity (Ref. 0460) Inhibitotory effect on Epstein-Barr virus activation (anti-tumor promotion) (Ref. 0217)							lmax (nm): petrol 446, 472, 502 (Ref. 0120); hexane 442, 472, 502 (Ref. 0119); acetone 445, 474, 504 (Ref. 0119)	nmax(KBr)/cm^-¹: 3400 (OH) (Ref. 0120)	¹H-NMR d(300 MHz, CDCl3): 1.51 (dd, J 12 and 8, 2, 2'-ax-H), 1.81 (dd, J 12 and 5, 2, 2'-eq-H), 4.35 (m, 3, 3'-H), 5.75 (br s, 4,4'-H), 6.48 (d, J 12, 7,7'-H), 6.73 (d, J 12, 8,8'-H), 6.43 (d, J 15, 10,10'-H), 6.66 (dd, J 15 and 11, 11,11'-H), 6.23 (d, J 11, 12,12'-H), ca. 6.40 (m, 14,14'-H), ca. 6.41 (m, 15,15'-H), 1.25 (s, 16,16'-Me), 1.45 (s, 17,17'-Me), 1.97 (d, J 1.5, 18,18'-Me), 1.97 (s, 19,19'-Me), 1.97 (s, 20,20'-Me) (Ref. 0119/0125/0460) ¹³C-NMR d(75.4 MHz, CDCl3): 35.5 s (C1), 50.4 t (C2), 65.6 d (C3), 128.8 d (C4), 134.8 s (C5), 144.1 s (C6), 121.9 d (C7), 131.6 d (C8), 136.1 s (C9), 138.8 d (C10), 125.0 d (C11), 132.6 d (C12), 135.4 s (C13), 137.4 d (C14), 129.1 d (C15), 27.3 t (C16), 31.7 t (C17), 21.4 t (C18), 12.8 t (C19), 12.2 t (C20), 35.5 s (C1'), 50.4 t (C2'), 65.6 d (C3'), 128.8 d (C4'), 134.8 s (C5'), 144.1 s (C6'), 121.9 d (C7'), 131.6 d (C8'), 136.1 s (C9'), 138.8 d (C10'), 125.0 d (C11'), 132.6 d (C12'), 135.4 s (C13'), 137.4 d (C14'), 129.1 d (C15'), 27.3 t (C16'), 31.7 t (C17'), 21.4 t (C18'), 12.8 t (C19'), 12.2 t (C20') (Maoka Takashi)	m/z: 566 (M), 506 (M-56), 493 (M-79), 474 (M-92), 460 (M-106), 427 (M-139), and 412 (M-152) (Ref. 0119)	CD data in EPA solution [Spectra 0020/0021] (Ref. 0119/0125) CD data in ether solution: De 213 (+10.3), 235 (0), 266 (24.7), 278(0), 307(-17.5), 382 (0), 367 (+13.0), 380(+20.2) (Ref. 0125)	HPLC (columun: YMC AL-313 (YMC Ltd., Kyoto) 0.625 cm, eluent and flow: 1.5 ml/min, MeOH for 10 min, then 10 min-linear gradient MeOH to EtOH) tR = ca. 8 min (Ref. 0125)	Buxus semperivirens (leaves) (Ref. 0125) Eschscholtia californica (petals) (Ref. 0119/0461) Taxus caspidata (berries) (Ref. 0460)	Treatment of the diacetate of (3R,3'R)-zeaxanthin with NBS, followed by dehydrobromination with morpholine gave eschscholtzxanthin diacetate, which was subsequently hydrolysed to give the free eschscholtzxanthin. (Ref. 0019)	in Buxus semperrivirens Eschscholtzxanthin monoanhydroeschscholtzxanthin anhydroeschscholtzxanthin (Ref. 0125) in Taxus caspidata Eschscholtzxanthin eschscholtzxanthone rhodoxanthin(Ref. 0460) in Eschscholtzia californica Zeaxanthin antheraxanthin eschscholtzxanthin (Ref. 0119)			[0019] / [0119] / [0120] / [0125] / [0217] / [0460] / [0461]
22		Rhodoxanthin	4',5',-Didehydro-4,5'-retro-b,b-carotene-3,3'-dione	VCA0022	Masayoshi Ito		C₄₀H₅₀O₂	562.824		Antioxidative activity (Ref. 0460), Inhibitotory effect on Epstein-Barr virus activation (anti-tumor promotion) (Ref. 0217)	208-209C (Ref. 0122) 212-214C (Ref. 0124) 194C (Ref. 0121)						lmax (nm): hexane 505 (E ¹^%₁_c_m = 2350) (Ref. 0122); CHCl3 493s (E ¹^%₁_c_m = 2140), 511 (2420) and 533s (2030) (Ref. 0124); cyclohexane 472 (E ¹^%₁_c_m = 2550), 443 (2530), 417 (1605) (Ref. 0121)	nmax(KBr)/cm^-¹: 1659s (conj. CO), 1576m, 1536m (conj. C=C), 992m, 978m (CH=CH, trans) (Ref. 0122/0124)	¹H-NMR d(60 MHz, CDCl3) [Spectrum 0022] (Ref. 0121) ¹H-NMR d(400 MHz, CDCl3) all-trans:1.39 (s, 16,17,16',17'-Me), 2.00 (s, 20, 20'-Me), 2.03 (s, 19, 19'-Me), 2.16 (d J 1, 18,18'-Me), 2.39 (s, 2,2'-H2), 5.94 (brs, 4,4'-H), 6.26 (d, J 11.5, 12,12'-H), ca 6.43 (m, 14, 14', 15, 15'-H), 6.46 (d, J 15.5, 10,10'-H), 6.79 (dd, J 14.5, J 12, 11,11'-H), 6.80 (d, J 12.5, 8,8'-H), 6.90 (d, J 12.7, 7,7'-H). 6-cis: 1.25 (s, 16,17-Me), 1.39 (s, 16',17'-Me), 1.99 (s, 20'-Me), 1.993 (s, 20'-Me), 2.016 (s, 19-Me), 2.029 (s, 19'-Me), 2.304 (d, J 1.2, 18-Me), 2.16 (d, J 1, 18'-Me), 2.34 (s, 2-H2), 2.39 (s, 2'-H2), 5.94 (brs, 4,4'-H), 6.24 (d, J 11.5, 12-H), 6.26 (d, J 11.5, 12'-H), ca 6.43 (m, 14, 14', 15, 15'-H), 6.40 (d, J 14.5, 10-H), 6.46 (d, J 14.5, 10'-H), 6.74 (dd, J 15, J 11.5, 11,H), 6.78 (dd, 11'-H), 6.55 (d, J 12.2, 8'-H), 6.80 (d, J 12.3, 8'-H), 6.67 (d, J 12.2, 7'-H), 6.90 (d J 12.3, 7'-H). (Ref. 0474) all-trans ¹³C-NMR d(100MHz, CDCl3): 12.41 (19), 12.91 (20), 22.31 (18), 29.87 (16, 17), 38.56 (1), 54.37 (2), 126.05 (4), 129.93 (11), 128.15 (7), 128.32 (8), 129.85 (15), 132.56 (12), 137.51 (13), 137.68 (14), 138.04 (10), 141.32 (9), 142.70 (6), 154.74 (5), 198.95 (3) (Ref. 0474) 6,6'-dicis ¹³C-NMR d(100MHz, CDCl3): 12.42 (19), 12.88 (20), 25.42 (18), 28.30 (16, 17), 41.26 (1), 52.50 (2), 125.48 (4), 126.40 (11), 128.79 and 128.83 (4) and (8),129.60 (15), 132.47 (12), 137.87, 137.54 and 137.05 (10), (13) and (14), 139.58 (9), 143.83 (6), 155.46 (5), 198.99 (3) (Ref. 0474)	m/z: 562 (M), 506 (M-56), 470 (M-92), 456 (M-106) (Ref. 0059/0122)		TLC (Kieselgel, CH2Cl2-ether 9:1) Rf = 0.33 (Ref. 0124) HPLC (column: Spherisorb S 5-CN, eluent: n-hexane-isopropyl acetate-acetone (76:17:7), flow rate: 1ml/min (Ref. 0474)	Taxus baccata (berries) (Ref. 0462) Taxus caspidata (berries) (Ref. 0460) Ricinus communis (cell cultures) (Ref. 0463) Aloe vera (leaves) (Ref. 0464) Cryptomeria japonica (leaves) (Ref. 0465) Metasequoia glyptostroboides (leaves) (Ref. 0465) Tilapia nilotica (integuments) (Ref. 0466/0417)	Rhodoxanthin was synthesized by the Wittig condensation of the C12-dialdehyde with 2 equiv. of the 3-oxo-retro-dehydro-C14-phosphorane, which was prepared in several steps starting from 6-oxoisophorone via 3-oxo-retro-dehydro-C11-aldehyde. (Ref. 0122) The Wittig condensation of the 2 equiv. of 5-(4,4-ethylenedioxy-2,6,6-trimethyl-1-cyclohexen-1-yl)-3-methyl-2,4-pentadienal (C15) or 5-(2,6,6-trimethyl-4-ethoxy1,3-cyclohexadien-1-yl)-3-methyl-2,4-pentadienal (C15) with 2,7-dimethyl-2,4,6-octatrienylene-bis-(triphenylphosphonium bromide), followed by hydrolysis with acid provided rhodoxanthin. (Ref. 0121) The key intermediate for the synthesis of rhodoxanthin, [3-methyl-5-(2,6,6-trimethyl-4-oxo-2-cyclohexen-1-yl)-2,4-pentadienyl]triphenylphosphonium bromide was synthesized starting from 6-oxo-isophorone via 3-oxo-cyclocitral and 3-oxo-ionone derivatives. (Ref. 0123) The key intermediate for the synthesis of rhodoxanthin, [3-methyl-5-(2,6,6-trimethyl-4-oxo-2-cyclohexen-1-yl)-2,4-pentadienyl]triphenylphosphonium bromide was synthesized via the reaction of 6-oxo-isophorone with the protected (E)-methylpent-2-en-4-yn-1-ol, simultaneous elimination of the tertiary hydroxy group and the partial reduction of the triple bond with Zn/acetic acid. This phosphonium salt was reacted with the C10-dialdehyde to give 6,6'-dihydrorhodoxanthin which was dehydrogenatede to provide rhodoxanthin. (Ref. 0019/0124)	Taxus caspidata (tree) Eschscholtzxanthin eschscholtzxanthone rhodoxanthin(Ref. 0460) Tilapia nilotica (fish) Zeaxanthin rhodoxanthin <0467>>			[0019] / [0059] / [0121] / [0122] / [0123] / [0124] / [0217] / [0417] / [0460] / [0462] / [0463] / [0464] / [0465] / [0466] / [0474]
23		Anhydroeschscholtzxanthin	2,3,2',3',4',5'-Hexadehydro-4,5'-retro-b,b-carotene	VCA0023	Masayoshi Ito		C₄₀H₅₀	530.825			196C (Ref. 0126)						lmax (nm): CS2 578, 539, 503 (Ref. 0126); diethylether 500, 530 (Ref. 0125)	nmax(KBr)/cm^-¹: 3030 (CH3), 2961 (CH3), 2920 (CH3), 1454 (CH3), 974 (olefin), 952 (olefin), 738 (Ref. 0125)	¹H-NMR d(300 MHz, CDCl3): 5.49 (d, J 9.5, 2, 2'-H), ca. 5.79 (dm, J 9.5, 3,3'-H), 5.79 (m, 4,4'-H), 6.60 (d, J 13, 7,7'-H), 6.87 (d, J 13, 8,8'-H), 6.45 (d, J 15, 10,10'-H), 6.64 (dd, J 15 and 11, 11,11'-H), 6.25 (d, J 11, 12,12'-H), ca. 6.40 (m, 14,14'-H), ca. 6.41 (m, 15,15'-H), 1.39 (s, 16,16'-Me), 1.39 (s, 17,17'-Me), 1.97 (s, 18,18'-Me), 1.97 (s, 19,19'-Me), 1.97 (s, 20,20'-Me) (Ref. 0125) ¹³C-NMR d(75.4 MHz, CDCl3): 38.5 s (C1), 140.9 d (C2), 118.3 d (C3), 123.2 d (C4), 133.5 s (C5), 145.9 s (C6), 123.5 d (C7), 130.3 d (C8), 136.2 s (C9), 138.8 d (C10), 124.6 d (C11), 132.8 d (C12), 135.8 s (C13), 137.4 d (C14), 129.0 d (C15), 29.8 t (C16), 29.8 t (C17), 21.0 t (C18), 12.8 t (C19), 12.0 t (C20), 38.5 s (C1'), 140.9 d (C2'), 118.3 d (C3'), 123.2 d (C4'), 133.5 s (C5'), 145.9 s (C6'), 123.5 d (C7'), 130.3 d (C8'), 136.2 s (C9'), 138.8 d (C10'), 124.6 d (C11'), 132.8 d (C12'), 135.8 s (C13'), 137.4 d (C14'), 129.0 d (C15'), 29.8 t (C16'), 29.8 t (C17'), 21.0 t (C18'), 12.8 t (C19'), 12.0 t (C20') (Maoka Takashi)			HPLC (columun: YMC AL-313 (YMC Ltd., Kyoto) 0.625 cm, eluent and flow: 1.5 ml/min, MeOH for 10 min, then 10 min-linear gradient MeOH to EtOH) tR = ca. 24 min (Ref. 0125)	Buxus semperivirens (leaves) (Ref. 0125/0468)	Partial synthesis of anhydroeschschlotzxanthin by dehydration of eschschlotzxanthin was discribed. (Ref. 0126)	in Buxus semperrivirens Eschscholtzxanthin monoanhydroeschscholtzxanthin anhydroeschscholtzxanthin (Ref. 0125)		Anhydroescholtzxanthin should be anhydroeschscholtzxanthin due to mistake.	[0125] / [0126] / [0468]
24		Monoanhydroeschscholtzxanthin	(3S)-2',3',4',5'-Tetradehydro-4,5'-retro-b,b-caroten-3-ol	VCA0024	Masayoshi Ito		C₄₀H₅₂O	548.840									lmax (nm): diethylether 458, 482, 515 (Ref. 0125)		¹H-NMR d(300 MHz, CDCl3): 1.51 (dd, J 12 and 8, 2-ax-H), 1.81 (dd, J 12 and 5, 2-eq-H), 4.35 (m, 3-H), 5.75 (br s, 4-H), 6.48 (d, J 12, 7-H), 6.73 (d, J 12, 8-H), 6.43 (d, J 15, 10-H), 6.66 (dd, J 15 and 11, 11-H), 6.23 (d, J 11, 12-H), ca. 6.40 (m, 14-H), ca. 6.41 (m, 15-H), 1.25 (s, 16-Me), 1.45 (s, 17-Me), 1.95 (d, J 1.5, 18-Me), 1.97 (s, 19-Me), 1.97 (s, 20-Me), 5.49 (d, J 9.5, 2'-H), ca. 5.79 (dm, J 9.5, 3'-H), ca. 5.79 (m, 4'-H), 6.60 (d, J 13, 7'-H), 6.87 (d, J 13, 8'-H), 6.45 (d, J 15, 10'-H), 6.64 (dd, J 15 and 11, 11'-H), 6.25 (d, J 11, 12'-H), ca. 6.40 (m, 14'-H), ca. 6.41 (m, 15'-H), 1.39 (s, 16'-Me), 1.39 (s, 17'-Me), 1.97 (s, 18'-Me), 1.97 (s, 19'-Me), 1.97 (s, 20'-Me) (Ref. 0125) ¹³C-NMR d(75.4 MHz, CDCl3): 35.5 s (C1), 50.4 t (C2), 65.6 d (C3), 128.8 d (C4), 134.8 s (C5), 144.1 s (C6), 121.9 d (C7), 131.6 d (C8), 136.1 s (C9), 138.8 d (C10), 125.0 d (C11), 132.6 d (C12), 135.4 s (C13), 137.4 d (C14), 129.1 d (C15), 27.3 t (C16), 31.7 t (C17), 21.4 t (C18), 12.8 t (C19), 12.2 t (C20), 38.5 s (C1'), 140.9 d (C2'), 118.3 d (C3'), 123.2 d (C4'), 133.5 s (C5'), 145.9 s (C6'), 123.5 d (C7'), 130.3 d (C8'), 136.1 s (C9'), 138.8 d (C10'), 124.5 d (C11'), 132.6 d (C12'), 135.7 s (C13'), 137.4 d (C14'), 129.0 d (C15'), 29.8 t (C16'), 29.8 t (C17'), 21.0 t (C18'), 12.8 t (C19'), 12.1 t (C20') (Maoka Takashi)	m/z: 548.4046 (M, C40H52O), 530 (M-18) (Ref. 0125)	CD data in EPA solution [Spectrum 0021] De 222 (+4.9), 248 (0), 281 (+2.9), 292 (0), 308 (0), 328 (-5,0), 345 (0), 382 (+4.6) (Ref. 0125)	HPLC (columun: YMC AL-313 (YMC Ltd., Kyoto) 0.625 cm, eluent and flow: 1.5 ml/min, MeOH for 10 min, then 10 min-linear gradient MeOH to EtOH) tR = ca. 16 min (Ref. 0125)	Buxus semperivirens (leaves) (Ref. 0125)	Partial synthesis of monoanhydroeschschlotzxanthin by dehydration of eschschlotzxanthin with dry hydrogen chloride in chloroform was discribed. (Ref. 0125)			Monoanhydroescholtzxanthin should be monoanhydroeschscholtzxanthin due to mistake.	[0125]
25		Fritschiellaxanthin/ (3S,3'R,6'R)-4-Ketolutein	(3S,3'R,6'R)-3,3'-Dihydroxy-b,e-caroten-4-one	VCA0025	Masayoshi Ito		C₄₀H₅₄O₃	582.855			178-180C (Ref. 0113)						lmax (nm): petrol 420, 443, 472 (Ref. 0113); hexane 458, 469 (Ref. 0117)	nmax(KBr)/cm^-¹: 3390 (OH), 2930, 2870 (CH), 1660 (conj. CO), 1555 (conj. C=C), 1440 (CH2), 1382, 1360 (CH3, gem. CH3), 985, 965 (trans disubst. C=C), 882, 828 (trans trisubst. C=C) (Ref. 0113)	¹H-NMR d(80 MHz, CDCl3) 0.85, 0.99 (each 3H, s, 16', 17'-Me), 1.21, 1.32 (each 3H, s, 16,17-Me), 1.62 (3H, s, 18'-Me), 1.91 (3H, s, 19'-Me), 1.94 (3H, s, 18-Me), 1.97 (9H, s, 19,20,20'-Me),4.24 (1H, m, 3'-H), 4.32 (1H, m, 3-H), 5.33 (1H, dd, H-7'), 5.48 (1H, br s, H-4'), 6.1-6.7 (13H, olefinic H) [Spectrum 0023] (Ref. 0113)	m/z: 582 (M, 35%), 564 (M-18, 100%), 546 (M-18-18, 10%), 490 (M-92, 5%), 476 (M-106, 3%), 472 (M-92-18, 1%), 458 (M-106-18, 1%) (Ref. 0113)	CD data in EPA solution [Spectrum 0024] (Ref. 0113) CD data in EPA solution (20C): De 235 (+3.0), 257 (+15.8), 272 (0), 294 (-8.0), 320 (-2.0), 354 (-6) (Ref. 0117)	TLC (Kieselguhr paper; acetone-petrol 10:90) Rf = 0.5 (Ref. 0113) HPLC (column: Sumipax OA-2000 (10mm) 0.425 cm, eluent: hexane-CH2Cl2-EtOH 48:16:0.6, flow: 0.8 ml/min) tR = ca. 46 min [Chromatogram 0004] (Ref. 0070)	Fritschiella tuberosa (Ref. 0116) Sesarma haematocheir (Ref. 0113) Paralithodes brevipes (Ref. 0469) Potamon dehaani (Ref. 0451>		Paralithodes brevipes: Lutein fritschiellaxanthin papilioerythrinone (Ref. 0469) Potamon dehaani: Lutein fritschiellaxanthin papilioerythrinone (Ref. 0451>			[0070] / [0113] / [0116] / [0117] / [0451] / [0469]
26		a-Doradexanthin/ (3S,3'S,6'R)-4-Ketolutein	(3S,3'S,6'R)-3,3'-Dihydroxy-b,e-caroten-4-one	VCA0026	Masayoshi Ito		C₄₀H₅₄O₃	582.855									lmax (nm): ether 453, 469 for a-doradexanthin-ester (Ref. 0116/0132)		¹H-NMR d(300 MHz, CDCl3) 0.85, 0.94 (each 3H, s, 16',17'-Me), 1.21, 1.32 (each 3H, s, 16,17-Me), 1.64 (3H, s, 18'-Me), 1.91 (6H, s,19'-Me), 1.94 (3H, s, 18-Me), 1.97 (9H, s, 19,20,20'-Me), 2.39 (1H, dd, H-2eq), 2.16 (1H, d, H-6'), 4.23 (1H, m, 3'-H), 4.32 (1H, m, 3-H), 5.53 (1H, dd, H-7'), 5.49 (1H, br s, H-4'), 6.1-6.7 (13H, olefinic H), 6.1-6.7 (13H, olefinic H) (Maoka Takashi)		CD data in ether solution: a-doradexanthin0ester De 227 (0), 243 (-), 250 (0), 273 (+), 313 (-), 340 (-) (Ref. 0454)	TLC (Kieselguhr paper; acetone-petrol 10:90) Rf = 0.4 (Ref. 0113) HPLC (column: Sumipax OA-2000 (10mm) 0.425 cm, eluent: hexane-CH2Cl2-EtOH 48:16:0.6, flow: 0.8 ml/min) tR = ca. 50 min [Chromatogram 0004] (Ref. 0070)	Carassius auratus (integuments) (Ref. 0116/0415/0470)		Carassius auratus: Lutein 3'-epilutein a-doradexanthin (Ref. 0415)			[0070] / [0113] / [0116] / [0132] / [0415] / [0454] / [0470]
27		6'-Epilutein/ Lutein F	(3R,3'R,6'S)-b,e-Carotene-3,3'-diol	VCA0027	Masayoshi Ito		C₄₀H₅₆O₂	568.871									lmax (nm): petrol 420, 444, 472 (Ref. 0408)		¹-NMR d (300MHz, CDCl3): 0.85 (3H, s, 16'-H), 0.94 (3H, s, H-17'), 1.07 (6H, s, H-16,17), 1.39 (1H, dd, H-2'ax), 1.48 (1H, dd, H-2ax), 1.64 (3H, s, H-18'), 1.65 (1H, dd, H-2'eq), 1.74 (3H, s, H-18), 1.91 (3H, s, H-19'), 1.97 (9H, s, H-19,20,20'), 2.04 (1H, dd, H-4ax), 2.39 (1H, dd, H-4eq), 2.16 (1H, d, H-6'), 4.00 (1H, m, H-3), 4.23 (1H, m, H-3'), 5.48 (1H, br s, H-4'), 5.53 (1H, dd, H-7'), 6.1-6.7 (13H, olefinic H) (Ref. 0452)	m/z: 568 (M), 550 (M-18), 532 (M-18-18) (Ref. 0408)	CD data in EPA solution: De 225 (-4.5), 240 (-6.8), 250 (-5.5), 272 (-10.0), 315 (-2.5), 332 (-4.5), 370 (-1.0) [Spectrum 0025] (Ref. 0452)		Branchiostegus japonicus japonicus (integuments) (Ref. 0452) Inimicus japonicus (integuments) (Ref. 0452) Platycephalus indicus (integuments) (Ref. 0452) Lagocephalus lunaris spadiceus (integuments) (Ref. 0452) Fugus vermiculare vermiculare (integuments) (Ref. 0452) Seriola quinqueradiata (integuments) (Ref. 0452) Pagrus major (integuments) (Ref. 0452) Coryphaena hippurus (integuments) (Ref. 0452) Eggs of Coryphaena hippurus (dolphin-fish) and Prognichthys agoo (flying fish) (Ref. 0408)	Partial synthesis of lutein F by reduction of (3R,6'RS)-3-hydroxy-b,e-caroten-3'-one with NaBH4 in methanol was discribed. (Ref. 0452)				[0408] / [0452]
28		3'-Epilutein/ Lutein B/ (Calthaxanthin)	(3R,3'S,6'R)-b,e-Carotene-3,3'-diol	VCA0028	Masayoshi Ito		C₄₀H₅₆O₂	568.871			151-152C (Ref. 0116) 162-163C (Ref. 0127)						lmax (nm): ether 419, 443, 473 (Ref. 0401); hexane (e) 268 (13800), 428 (77500), 444 (116400), 472 (105500) (Ref. 0119); hexane (e) 421 (90000), 444 (133000), 473 (127000) (Ref. 0127)		¹H-NMR d(270 MHz, CDCl3): 0.854, 0.944 (each 3H, s, 1'-gem-Me), 1.074 (6H, s, 1-gem-Me), 1.32 (d, J ca. 7), ca. 1.34 (OH), 1.477 (1H, t, J ca.12, 2b-H), 1.645 (3H, s, 5'-Me), 1.738 (3H, s, 5-Me), 1.907 (3H, s, 9'-Me), 1.968 (9H, s, 9-, 13-, 13'-Me), 2.05 (1H, dd, J ca. 17, 9.5, 4b-H), 2.16 (1H, d, J ca. 9.5, 6'-H), 2.39 (1H, dd, J ca. 17, 6, 4a-H), ca. 4.00 (1H, m, 3-H), 4.23 (1H, m, 3'-H), 5.49 (1H, s, 4'-H), 5.53 (1H, dd, J 15.5, 9.5, 7'-H), ca. 6.12 (2H, s, 7-, 8-H), 6.13 (1H, d, 8'-H), ca. 6.13 and ca. 6.16 (2H, 10-, 10'-H), 6.25 (2H, m, 14-, 14'-H), 6.35 and 6.36 ( each 1H, d, J ca. 15, 12-, 12'-H), 6.15-6.61 (4H, m, 11-, 11'-, 15-, 15'-H) (Ref. 0128/0116/0127)	m/z: 568 (M), 550 (M-18), 532 (M-18-18) (Ref. 0401/0116/0127)	CD data (ether-hexane 1:4): De 228 (0), 241 (+8.9), 264 (0), 288 (-5.8), 302 (0), 330 (+3.1) [Spectrum 0026] (Ref. 0408)	TLC (Mg2(OH)2CO3 plates, acetone-petrol 15:85) Rf=0.65 (Ref. 0401) HPLC (column: Spherisorb 5S, eluent: hexane-CH2Cl2-2-Propanol-NEt(iso-Pr)2 90.9:6.5:2.5:0.1) [Chromatogram 0016] (Ref. 0128)	Caltha palustris (petals) (Ref. 0127/0453), Rosa gallica (petals) (Ref. 0450) Carassius auratus (integuments) (Ref. 0415/0470) Integuments of several fishes (Ref. 0455)		Carassius auratus: Lutein 3'-epilutein a-doradexanthin (Ref. 0470)			[0116] / [0119] / [0127] / [0128] / [0401] / [0408] / [0415] / [0450] / [0453] / [0455] / [0470]
29		3',6'-Diepilutein/ Lutein D	(3R,3'S,6'S)-b,e-Carotene-3,3'-diol	VCA0029	Masayoshi Ito		C₄₀H₅₆O₂	568.871			154-155C (Ref. 0452)						lmax (nm): petrol 420, 444, 472 (Ref. 0408)		same as Lutein A ¹H-NMR d(270 MHz, CDCl3): 0.849, 0.998 (6H, s, 1'-gem-Me), 1.074 (6H, s, 1-gem-Me), 1.37 (1H, dd, J 13, 7, 2'ax-H), 1.48 (1H, t, J 12, 2ax-H), 1.626 (3H, s, 5'-Me), 1.739 (3H, s, 5-Me), 1.84 (1H, dd, J 13, 6, 2'eq-H), 1.912 (3H, s, 9'-Me), 1.970 (9H, s, 9-, 13-, 13'-Me), 2.04 (1H, dd, J 17, 10, 4ax-H), ca. 2.33-2.45 (2H, m, 6'-, 4eq-H), ca. 4.0 (1H, m, 3-H), 4.25 (1H, 3'-H), 5.43 (1H, dd, J 15.5, 10, 7'-H), 5.55 (1H, s, 4'-H), ca. 6.12 (2H, s, 7-, 8-H), ca. 6.15 (3H, m, 8'-, 10-, 10'-H), ca. 6.26 (2H, m, 14-, 14'-H), 6.36 (2H, d, J 15, 12-, 12'-H), ca. 6.55-6.71 (4H, m, 11-, 11'-, 15-, 15'-H) (Ref. 0086/0128/0452)	m/z: 568 (M), 550 (M-18), 532 (M-18-18) (Ref. 0408)	CD data in EPA solution: De 215 (-11.0), 220 (-13.0), 233 (0), 236 (+1.2), 256 (-13.0), 310 (0), 325 (+1.0), 380 (0) [Spectrum 0027] (Ref. 0452)		Branchiostegus japonicus japonicus (integuments) (Ref. 0452) Inimicus japonicus (integuments) (Ref. 0452) Platycephalus indicus (integuments) (Ref. 0452) Lagocephalus lunaris spadiceus (integuments) (Ref. 0452) Fugus vermiculare vermiculare (integuments) (Ref. 0452) Seriola quinqueradiata (integuments) (Ref. 0452) Pagrus major (integuments) (Ref. 0452) Coryphaena hippurus (integuments) (Ref. 0452) Eggs of Coryphaena hippurus (dolphin-fish) (Ref. 0408)	Partial synthesis of lutein D by reduction of (3R,6'RS)-3-hydroxy-b,e-caroten-3'-one with NaBH4 in methanol was discribed. (Ref. 0452)				[0086] / [0128] / [0408] / [0452]
30		Lactucaxanthin/ Tunaxanthin F	(3R,6R,3'R,6'R)-e,e-Carotene-3,3'-diol	VCA0030	Masayoshi Ito		C₄₀H₅₆O₂	568.871		Inhibitotory effect on Epstein-Barr virus activation (anti-tumor promotion) (Ref. 0217) Substantial amount of lactucaxanthin is found in photosystem II (LHC II) of Lactuca sativa (lettuce): LHC IIa (CP29), LHCP IIb and LHCP IIc (CP26) (Ref. 1149).							lmax (nm): petrol 414, 437, 467 (Ref. 0115); acetone 426, 440, 471 (Ref. 0129); ethanol 424, 438.5, 468 (Ref. 0129); ether 268, 418, 439 (Maoka Takashi)		¹H-NMR d(100 MHz, CDCl3): 0.85 (6H, s), 1.00 (6H, s), 1.62 (6H, s), 1.91 (6H, s), 1.96 (6H, s), ca. 5.4 (2H, m), 6.04-6.65 (ca 14H) (Ref. 0129) ¹H-NMR d(300 MHz, CDCl3): 0.85, 0.10 (each 6H, s, 16,16',17,17'-Me), 1.37 (2H, dd, 2,2'a-H), 1.63 (6H, s, 18,18'-Me), 1.85(2H, dd, 2, 2'b-H), 1.91 (6H, s, 19,19'-Me), 1.97 (6H, s, 20,20'-Me), 2.41 (2H, d, 6,6'-H), 4.25 (2H, m 3,3'-H), 5.42 (2H, dd, 7,7'-H), 5.55 (2H, br s, 4,4'-H), 6.1-6.7 (12H, olefinic H) (Maoka Takashi)	m/z: 568 (M), 550 (M-18), 532 (M-18-18), 476 (M-92), 462 (M-106) (Maoka Takashi)	CD data in EPA solution [Spectrum 0030] (Ref. 0115) CD data in EPA solution: De 215 (+4), 230 (+7), 264 (+17.5), 290 (+1.5), 325 (+2.5), 390 (0) (Ref. 0129)	HPLC (column: Spherisorb S-5 CN, eluent: hexane-CH2Cl2-MeOH-NEt(iso-Pr)2 80.4:17:2.5:0.1) [Chromatogram 0015] (Ref. 0128) HPLC (column: Sumipax OA-2000 (5mm) 0.425 cm, eluent: hexane-CH2Cl2-EtOH 54:10:0.3, flow: 0.6 ml/min) [Chromatogram 0017] (Ref. 0069/0130) HPLC (column: Sumipax OA-2000 (5mm) 0.830 cm, eluent: hexane-CH2Cl2-EtOH 54:10:0.1, flow: 1.2 ml/min)---separation of dibenzoate of tunaxanthins [Chromatogram 0018] (Ref. 0069/0130)	Lactuca sativa (Ref. 0129) Tilapia nilotica (integuments) (Ref. 0115)		Usually the substrate of lycopen e-cyclase is only lycopene and d-carotene and g-carotene are not, while lycopene e-cyclase from Lactuca sativa (romaine lettuce) can cyclize d-carotene to form e-carotene and the final product is lactucaxanthin. A single amino acid is found to act as a molecular switch: one e-ring or two (Ref. 1148).		Semi-empirical molecular orbital calculations using AM1 Hamiltonian (MNDO-AM1 method) were performed in order to predict their stable structures (Ref. 1337).	[0069] / [0115] / [0128] / [0129] / [0130] / [0217] / [1148] / [1149] / [1337]
31		Tunaxanthin H	(3R,6R,3'R,6'S)-e,e-Carotene-3,3'-diol	VCA0031	Masayoshi Ito		C₄₀H₅₆O₂	568.871									lmax (nm): ether 268, 418, 439 (Maoka Takashi)			m/z: 568 (M), 550 (M-18), 532 (M-18-18), 476 (M-92), 462 (M-106) (Maoka Takashi)		HPLC (column: Spherisorb S-5 CN, eluent: hexane-CH2Cl2-MeOH-NEt(iso-Pr)2 80.4:17:2.5:0.1) [Chromatogram 0015] (Ref. 0128) HPLC (column: Sumipax OA-2000 (5mm) 0.425 cm, eluent: hexane-CH2Cl2-EtOH 54:10:0.3, flow: 0.6 ml/min) [Chromatogram 0017] (Ref. 0069/0130) HPLC (column: Sumipax OA-2000 (5mm) 0.830 cm, eluent: hexane-CH2Cl2-EtOH 54:10:0.1, flow: 1.2 ml/min)---separation of dibenzoate of tunaxanthins [Chromatogram 0018] (Ref. 0069/0130)	Cyprinus carpio (integuments) (Ref. 0456)					[0069] / [0128] / [0130] / [0456]
32		Tunaxanthin I/ Chiriquixanthin A	(3R,6R,3'S,6'R)-e,e-Carotene-3,3'-diol	VCA0032	Masayoshi Ito		C₄₀H₅₆O₂	568.871									lmax (nm): acetone 417, 441, 470 (Ref. 0131); ether 268, 418, 439 (Maoka Takashi)		¹H-NMR d(100 MHz, CDCl3): 0.84 (6H, s 1,1'-Me), 0.94 (3H, s 1'-Me), 0.99 (3H, s 1-Me), 1.63 (6H, s, 5,5'-Me), 1.91 (6H, s, 9,9'-Me), 1.97 (6H, s, 13,13'-Me) (Ref. 0131/0133)	m/z: 568 (M), 550 (M-18), 532 (M-18-18), 476 (M-92), 462 (M-106) (Maoka Takashi)	CD cotton effect: De 268 nm (+15.0) (Ref. 0133)	HPLC (column: Spherisorb S-5 CN, eluent: hexane-CH2Cl2-MeOH-NEt(iso-Pr)2 80.4:17:2.5:0.1) [Chromatogram 0015] (Ref. 0128) HPLC (column: Sumipax OA-2000 (5mm) 0.425 cm, eluent: hexane-CH2Cl2-EtOH 54:10:0.3, flow: 0.6 ml/min) [Chromatogram 0017] (Ref. 0069/0130) HPLC (column: Sumipax OA-2000 (5mm) 0.830 cm, eluent: hexane-CH2Cl2-EtOH 54:10:0.1, flow: 1.2 ml/min)---separation of dibenzoate of tunaxanthins [Chromatogram 0018] (Ref. 0069/0130)	Atelopus chiriquiensis (skins) (Ref. 0131)					[0069] / [0128] / [0130] / [0131] / [0133]
33		Tunaxanthin E	(3R,6R,3'S,6'S)-e,e-Carotene-3,3'-diol	VCA0033	Masayoshi Ito		C₄₀H₅₆O₂	568.871									lmax (nm): ether 268, 418, 439 (Maoka Takashi)			m/z: 568 (M), 550 (M-18), 532 (M-18-18), 476 (M-92), 462 (M-106) (Maoka Takashi)		HPLC (column: Spherisorb S-5 CN, eluent: hexane-CH2Cl2-MeOH-NEt(iso-Pr)2 80.4:17:2.5:0.1) [Chromatogram 0015] (Ref. 0128) HPLC (column: Sumipax OA-2000 (5mm) 0.425 cm, eluent: hexane-CH2Cl2-EtOH 54:10:0.3, flow: 0.6 ml/min) [Chromatogram 0017] (Ref. 0069/0130) HPLC (column: Sumipax OA-2000 (5mm) 0.830 cm, eluent: hexane-CH2Cl2-EtOH 54:10:0.1, flow: 1.2 ml/min)---separation of dibenzoate of tunaxanthins [Chromatogram 0018] (Ref. 0069/0130)	Chaenogobius isaza (integuments) (Ref. 0457)					[0069] / [0128] / [0130] / [0457]
34		Tunaxanthin C/ Oxyxantin 58/ (ent. Chiriquixanthin B)	(3R,6S,3'R,6'S)-e,e-Carotene-3,3'-diol	VCA0034	Masayoshi Ito		C₄₀H₅₆O₂	568.871									lmax (nm): petrol 414, 437, 467 (Ref. 0114); ether 268, 418, 439 (Maoka Takashi)		¹H-NMR d(100 MHz, CDCl3): 0.84, 0.94 (each 6H, s 1,1'-Me), 1.63 (6H, s, 5,5'-Me), 1.91 (6H, s, 9,9'-Me), 1.97 (6H, s, 13,13'-Me) (Ref. 0131/0133) ¹H-NMR d(300 MHz, CDCl3): 0.85, 0.94 (each 6H, s, 16,16',17,17'-Me), 1.39 (2H, dd, 2,2'a-H),1.63 (6H, s, 18,18'-Me), 1.65 (2H, dd, 2,2'b-H), 1.91 (6H, s, 19,19'-Me), 1.97 (6H, s, 20,20'-Me), 2.16 (2H, d, 6,6'-H), 4.23 (2H, m, 3,3'-H), 5,49 (2H, brs, H-4,4'), 5.53 (2H, dd, 7,7'-H), 6.1-6.7 (12H, olefinic H) (Maoka Takashi)	m/z: 568 (M), 550 (M-18), 532 (M-18-18), 476 (M-92), 462 (M-106) (Maoka Takashi)	CD data in EPA solution [Spectrum 0029] De 268 nm (-18.0) (Ref. 0114) CD cotton effect: De 268 nm (-14.0) (Ref. 0133)	HPLC (column: Spherisorb S-5 CN, eluent: hexane-CH2Cl2-MeOH-NEt(iso-Pr)2 80.4:17:2.5:0.1) [Chromatograms 0015)] (Ref. 0128) HPLC (column: Sumipax OA-2000 (5mm) 0.425 cm, eluent: hexane-CH2Cl2-EtOH 54:10:0.3, flow: 0.6 ml/min) [Chromatogram 0017] (Ref. 0069/0130) HPLC (column: Sumipax OA-2000 (5mm) 0.830 cm, eluent: hexane-CH2Cl2-EtOH 54:10:0.1, flow: 1.2 ml/min)---separation of dibenzoate of tunaxanthins [Chromatogram 0018] (Ref. 0069/0130) HPLC (column: Sumipax OA-2000 (5mm) 0.425 cm, eluent: hexane-CH2Cl2-EtOH 54:10:0.3, flow: 0.6 ml/min) [Chromatogram 0019] (Ref. 0111) HPLC (column: Zorbax CN 0.425 cm, eluent: hexane-CH2Cl2-NEt(iso-Pr)2 90:10:0.1, flow: 4.0 ml/min) [Chromatogram 0020] (Ref. 0112)	Sebastes flavidus (integuments) (Ref. 0111/0112) Oxyjulis californica (integuments) (Ref. 0133) Sebastes inermis (integuments), Seriola quinqueradiata (integuments), Prognichthys agoo (integuments), Stephanolepis cirrhifer (integuments), Coryphaena hippurus (integuments) (Ref. 0112) integuments of several fishes (Ref. 0458)		Marine fish egg (Prognichthys aggo, Seriola quinqueradiata): astaxanthin idoxanthin b,b-carotene-3,4,3'-triol zeaxanthin 3-hydroxy-b,e-caroten-3'-one e,e-carotene-3,3'-dione 3-hydroxy-e,e-caroten-3'-dione tunaxanthin A, B and C (Ref. 0408) Yellowtail (Seriola quinqueradiata): astaxanthin b-carotene-triol zeaxanthin 3'-epilutein tunaxanthin A, B and C (Ref. 0430/0435) Red sea bream (Pagrus major): astaxanthin b-carotene-triol zeaxanthin 3'-epilutein tunaxanthin A, B, and C (Ref. 0432)		Semi-empirical molecular orbital calculations using AM1 Hamiltonian (MNDO-AM1 method) were performed in order to predict their stable structures (Ref. 1337).	[0069] / [0111] / [0112] / [0114] / [0128] / [0130] / [0131] / [0133] / [0408] / [0430] / [0432] / [0435] / [0458] / [1337]
35		Tunaxanthin D	(3R,6S,3'S,6'R)-e,e-Carotene-3,3'-diol	VCA0035	Masayoshi Ito		C₄₀H₅₆O₂	568.871									lmax (nm): petrol 418, 439, 468 (Ref. 0112); ether 268, 418, 439 (Maoka Takashi)		¹H-NMR d(300 MHz, CDCl3): 0.85, 0.94 (each 6H, s, 16,16',17,17'-Me), 1.39 (2H, dd, 2,2'a-H),1.63 (6H, s, 18,18'-Me), 1.65 (2H, dd, 2,2'b-H), 1.91 (6H, s, 19,19'-Me), 1.97 (6H, s, 20,20'-Me), 2.16 (2H, d, 6,6'-H), 4.23 (2H, m, 3,3'-H), 5,49 (2H, br s, 4,4'-H), 5.53 (2H, dd, 7,7'-H), 6.1-6.7 (12H, olefinic H) (Maoka Takashi)	m/z: 568 (M), 550 (M-18), 532 (M-18-18), 476 (M-92), 462 (M-106) (Maoka Takashi)	CD spectrum: no optical activity (Ref. 0112)	HPLC (column: Spherisorb S-5 CN, eluent: hexane-CH2Cl2-MeOH-NEt(iso-Pr)2 80.4:17:2.5:0.1) [Chromatogram 0015] (Ref. 0128) HPLC (column: Sumipax OA-2000 (5mm) 0.425 cm, eluent: hexane-CH2Cl2-EtOH 54:10:0.3, flow: 0.6 ml/min) [Chromatogram 0017] (Ref. 0069/0130) HPLC (column: Sumipax OA-2000 (5mm) 0.830 cm, eluent: hexane-CH2Cl2-EtOH 54:10:0.1, flow: 1.2 ml/min)---separation of dibenzoate of tunaxanthins [Chromatogram 0018] (Ref. 0069/0130) HPLC (column: Sumipax OA-2000 (5mm) 0.425 cm, eluent: hexane-CH2Cl2-EtOH 54:10:0.3, flow: 0.6 ml/min) [Chromatogram 0019] (Ref. 0111) HPLC (column: Zorbax CN 0.425 cm, eluent: hexane-CH2Cl2-NEt(iso-Pr)2 90:10:0.1, flow: 4.0 ml/min) [Chromatogram 0020] (Ref. 0112)	Sebastes inermis (integuments), Seriola quinqueradiata (integuments), Prognichthys agoo (integuments), Stephanolepis cirrhifer (integuments), Coryphaena hippurus (integuments) (Ref. 0112)				Semi-empirical molecular orbital calculations using AM1 Hamiltonian (MNDO-AM1 method) were performed in order to predict their stable structures (Ref. 1337).	[0069] / [0111] / [0112] / [0128] / [0130] / [1337]
36		Tunaxanthin J/ Chiriquixanthin B	(3S,6R,3'S,6'R)-e,e-Carotene-3,3'-diol	VCA0036	Masayoshi Ito		C₄₀H₅₆O₂	568.871									lmax (nm): acetone 417, 441, 470 (Ref. 0131); ether 268, 418, 439 (Maoka Takashi)		¹H-NMR d(100 MHz, CDCl3): 0.84, 0.94 (each 6H, s 1,1'-Me), 1.63 (6H, s, 5,5'-Me), 1.91 (6H, s, 9,9'-Me), 1.97 (6H, s, 13,13'-Me) (Ref. 0131/0133) ¹H-NMR d(300 MHz, CDCl3): 0.85, 0.94 (each 6H, s, 16,16',17,17'-Me), 1.39 (2H, dd, 2,2'a-H),1.63 (6H, s, 18,18'-Me), 1.65(2H, dd, 2,2'b-H), 1.91 (6H, s, 19,19'-Me), 1.97 (6H, s, 20,20'-Me), 2.16 (2H, d, 6,6'-H), 4.23 (2H, m, 3,3'-H), 5,49 (2H, br s, 4,4'-H), 5.53 (2H, dd, 7,7'-H), 6.1-6.7 (12H, olefinic H) (Maoka Takashi)	m/z: 568 (M), 550 (M-18), 532 (M-18-18), 476 (M-92), 462 (M-106) (Maoka Takashi)	CD cotton effect: De 268 nm (+9.5) (Ref. 0133) CD cotton effect: De 268nm (+20) (Ref. 0111)	HPLC (column: Spherisorb S-5 CN, eluent: hexane-CH2Cl2-MeOH-NEt(iso-Pr)2 80.4:17:2.5:0.1) [Chromatogram 0015] (Ref. 0128) HPLC (column: Sumipax OA-2000 (5mm) 0.425 cm, eluent: hexane-CH2Cl2-EtOH 54:10:0.3, flow: 0.6 ml/min) [Chromatogram 0017] (Ref. 0069/0130) HPLC (column: Sumipax OA-2000 (5mm) 0.830 cm, eluent: hexane-CH2Cl2-EtOH 54:10:0.1, flow: 1.2 ml/min)---separation of dibenzoate of tunaxanthins [Chromatogram 0018] (Ref. 0069/0130) HPLC (column: Sumipax OA-2000 (5mm) 0.425 cm, eluent: hexane-CH2Cl2-EtOH 54:10:0.3, flow: 0.6 ml/min) [Chromatogram 0019] (Ref. 0111)	Atelopus chiriquiensis (skins) (Ref. 0131) Sebastes flavidus (integuments) (Ref. 0111/0133)				Semi-empirical molecular orbital calculations using AM1 Hamiltonian (MNDO-AM1 method) were performed in order to predict their stable structures (Ref. 1337).	[0069] / [0111] / [0128] / [0130] / [0131] / [0133] / [1337]
37		Tunaxanthin B/ Oxyxanthin 51	(3R,6S,3'S,6'S)-e,e-Carotene-3,3'-diol	VCA0037	Masayoshi Ito		C₄₀H₅₆O₂	568.871									lmax (nm): ether 268, 418, 439 (Maoka Takashi)		¹H-NMR d(100 MHz, CDCl3): 0.84 (6H, s 1,1'-Me), 0.94 (3H, s 1'-Me), 0.99 (3H, s 1-Me), 1.63 (6H, s, 5,5'-Me), 1.91 (6H, s, 9,9'-Me), 1.97 (6H, s, 13,13'-Me) (Ref. 0133/0459) ¹H-NMR d(300 MHz, CDCl3): 0.85 (6H, s 16, 16'-Me), 0.94, 0.10 (each 3H, s, 17,17'-Me), 1.37 (1H, dd, 2'a-H), 1.39 (1H, dd, 2a-H),1.63 (6H, s, 18,18'-Me), 1.65(1H, dd 2b-H), 1.85 (2H, dd, 2'b-H), 1.91 (6H, s, 19,19'-Me), 1.97 (6H, s, 20,20'-Me), 2.16 (1H, d, 6-H), 2.41 (1H, d, 6'-H), 4.23 (1H, m, 3-H), 4.25 (1H, m,3'-H), 5.42 (1H, dd, 7'-H), 5,49 (1H, br.s, 4-H), 5.53 (1H, dd, 7-H), 5.55 (1H, br s, 4'-H), 6.1-6.7 (12H, olefinic H) (Maoka Takashi)	m/z: 568 (M), 550 (M-18), 532 (M-18-18), 476 (M-92), 462 (M-106) (Maoka Takashi)	CD cotton effect: De 268 nm (-14.0) (Ref. 0133)	HPLC (column: Sumipax OA-2000 (5mm) 0.425 cm, eluent: hexane-CH2Cl2-EtOH 54:10:0.3, flow: 0.6 ml/min) [Chromatogram 0017] (Ref. 0069/0130) HPLC (column: Sumipax OA-2000 (5mm) 0.830 cm, eluent: hexane-CH2Cl2-EtOH 54:10:0.1, flow: 1.2 ml/min)---separation of dibenzoate of tunaxanthins [Chromatogram 0018] (Ref. 0069/0130) HPLC (column: Zorbax CN 0.425 cm, eluent: hexane-CH2Cl2-NEt(iso-Pr)2 90:10:0.1, flow: 4.0 ml/min) [Chromatogram 0020] (Ref. 0112)	Sebastes inermis (integuments), Seriola quinqueradiata (integuments), Prognichthys agoo (integuments), Stephanolepis cirrhifer (integuments), Coryphaena hippurus (integuments) (Ref. 0112) Oxyjulis californica (integuments) (Ref. 0133) Thunnus thynnus (integuments), Amanses modestus (integuments) (Ref. 0459) integuments of several fishes (Ref. 0458)		marine fish egg (Prognichthys aggo, Seriola quinqueradiata): astaxanthin idoxanthin b,b-carotene-3,4,3'-triol zeaxanthin 3-hydroxy-b,e-caroten-3'-one e,e-carotene-3,3'-dione 3-hydroxy-e,e-caroten-3'-dione tunaxanthin A, B and C (Ref. 0408) Yellowtail (Seriola quinqueradiata): astaxanthin b-carotene-triol zeaxanthin 3'-epilutein tunaxanthin A, B and C (Ref. 0430/0435) Red sea bream (Pagrus major): astaxanthin b-carotene-triol zeaxanthin 3'-epilutein tunaxanthin A, B, and C (Ref. 0432)			[0069] / [0112] / [0130] / [0133] / [0408] / [0430] / [0432] / [0435] / [0458] / [0459]
38		Tunaxanthin G	(3S,6R,3'S,6'S)-e,e-Carotene-3,3'-diol	VCA0038	Masayoshi Ito		C₄₀H₅₆O₂	568.871									lmax (nm): ether 268, 418, 439 (Maoka Takashi)			m/z: 568 (M), 550 (M-18), 532 (M-18-18), 476 (M-92), 462 (M-106) (Maoka Takashi)		HPLC (column: Spherisorb S-5 CN, eluent: hexane-CH2Cl2-MeOH-NEt(iso-Pr)2 80.4:17:2.5:0.1) [Chromatogram 0015] (Ref. 0128) HPLC (column: Sumipax OA-2000 (5mm) 0.425 cm, eluent: hexane-CH2Cl2-EtOH 54:10:0.3, flow: 0.6 ml/min) [Chromatogram 0017] (Ref. 0069/0130)HPLC (column: Sumipax OA-2000 (5mm) 0.830 cm, eluent: hexane-CH2Cl2-EtOH 54:10:0.1, flow: 1.2 ml/min)---separation of dibenzoate of tunaxanthins [Chromatogram 0018] (Ref. 0069/0130)	Cyprinus carpio (integuments) (Ref. 0456)					[0069] / [0128] / [0130] / [0456]
39		Tunaxanthin A/ Oxyxanthin 45/ (ent. Lactucaxanthin)	(3S,6S,3'S,6'S)-e,e-Carotene-3,3'-diol	VCA0039	Masayoshi Ito		C₄₀H₅₆O₂	568.871									lmax (nm): petrol 414, 437, 467 (Ref. 0115); ether 268, 418, 439 (Maoka Takashi)		¹H-NMR d(100 MHz, CDCl3): 0.84, 0.99 (each 6H, s 1,1'-Me), 1.63 (6H, s, 5,5'-Me), 1.91 (6H, s, 9,9'-Me), 1.97 (6H, s, 13,13'-Me) (Ref. 0133) ¹H-NMR d(300 MHz, CDCl3): 0.85, 0.10 (each 6H, s, 16,16',17,17'-Me), 1.37 (2H, d, 2,2'a-H), 1.63 (6H, s, 18,18'-Me), 1.85(2H, d, 2,2'b-H), 1.91 (6H, s, 19,19'-Me), 1.97 (6H, s, 20,20'-Me), 2.41 (2H, d, 6,6'-H), 4.25 (2H, m 3,3'-H), 5.42 (2H, d, 7,7'-H), 5.55 (2H, br s, 4,4'-H), 6.1-6.7 (12H, olefinic H) (Maoka Takashi)	m/z: 568 (M), 550 (M-18), 532 (M-18-18), 476 (M-92), 462 (M-106) (Maoka Takashi)	CD cotton effect (in EPA): De 268nm (-24.0) [Spectrum 0030] (Ref. 0115) CD cotton effect: De 268 nm (-9.2) (Ref. 0133)	HPLC (column: Spherisorb S-5 CN, eluent: hexane-CH2Cl2-MeOH-NEt(iso-Pr)2 80.4:17:2.5:0.1) [Chromatogram 0015] (Ref. 0128) HPLC (column: Sumipax OA-2000 (5mm) 0.425 cm, eluent: hexane-CH2Cl2-EtOH 54:10:0.3, flow: 0.6 ml/min) [Chromatogram 0017] (Ref. 0069/0130) HPLC (column: Sumipax OA-2000 (5mm) 0.830 cm, eluent: hexane-CH2Cl2-EtOH 54:10:0.1, flow: 1.2 ml/min)---separation of dibenzoate of tunaxanthins [Chromatogram 0018] (Ref. 0069/0130) HPLC (column: Zorbax CN 0.425 cm, eluent: hexane-CH2Cl2-NEt(iso-Pr)2 90:10:0.1, flow: 4.0 ml/min) [Chromatogram 0020] (Ref. 0112)	Sebastes inermis (integuments), Seriola quinqueradiata (integuments), Prognichthys agoo (integuments), Stephanolepis cirrhifer (integuments), Coryphaena hippurus (integuments) (Ref. 0112) Oxyjulis californica (integuments) (Ref. 0133) integuments of several fishes (Ref. 0458)		Marine fish egg (Prognichthys aggo, Seriola quinqueradiata): astaxanthin idoxanthin b,b-carotene-3,4,3'-triol zeaxanthin 3-hydroxy-b,e-caroten-3'-one e,e-carotene-3,3'-dione 3-hydroxy-e,e-caroten-3'-dione tunaxanthin A, B and C (Ref. 0408) Yellowtail (Seriola quinqueradiata): astaxanthin b-carotene-triol zeaxanthin 3'-epilutein tunaxanthin A, B and C (Ref. 0430/0435) Red sea bream (Pagrus major): astaxanthin b-carotene-triol zeaxanthin 3'-epilutein tunaxanthin A, B, and C (Ref. 0432)		Semi-empirical molecular orbital calculations using AM1 Hamiltonian (MNDO-AM1 method) were performed in order to predict their stable structures (Ref. 1337).	[0069] / [0112] / [0115] / [0128] / [0130] / [0133] / [0408] / [0430] / [0432] / [0435] / [0458] / [1337]
40		Canthaxanthin	b,b-Carotene-4,4'-dione	VCA0040	Masayoshi Ito		C₄₀H₅₂O₂	564.840		Antioxidant activity (Ref. 0092/0093/0215/0226/0489/0490/0491) Singlet oxygen quenching activity (Ref. 0230/0441/0492) Immunomodulating action (Ref. 0213) Chemoprevention of carcinogenesis (Ref. 0219) Inhibitotory effect on Epstein-Barr virus activation (anti-tumor promotion) (Ref. 0217)	212-213C (Ref. 0121) 216-217C (Ref. 0138)						lmax (nm): cyclohexane 469 (E ¹^%₁_c_m = 2200) (Ref. 0121); hexane 466 (Ref. 0136); benzene 476 (Ref. 0136); petrol 465-467 (E ¹^%₁_c_m = 2200) (Ref. 0138); methanol [Spectrum 1109]	nmax(KBr)/cm^-¹: 3020, 2950, 2910, 2850 (CH), 1650 (CO), 1575, 1550, 1450, 1385, 1360, 1350, 1340, 1320, 1300, 1250, 1178, 1072, 958, 946 (Ref. 0136)	¹H-NMR d(CDCl3): 1.195 (s, ca. 12H, 1,1'-gem-Me), 1.853 (t, J 6.7, 4H, 2,2'-H2), 1.873 (s, 6H, 5,5'-Me), 1.983 (s, 6H, 13,13'-Me), 2.003 (s, 6H, 9,9'-Me), 2.508 (t, J 6.7, 4H, 3,3'-H2), 6.24 (d, J 16, 2H, 7,7'-H), 6.28 (d, J 12, 2H, 10,10'-H), ca. 6.30 (m, 2H, 14,14'-H), 6.35 (d, J 16, 2H, 8,8'-H), 6.43 (d, J 14.8, 2H, 12,12'-H), ca. 6.65 (m, 4H, 11,11',15,15'-H) (Ref. 0420) ¹³C-NMR d(CDCl3): 35.7 (1, 1'), 37.7 (2, 2'), 34.3 (3, 3'), 198.7 (4, 4'), 129.9 (5, 5'), 160.9 (6, 6'), 124.2 (7, 7'), 141.1 (8, 8'), 134.8 (9, 9'), 134.3 (10, 10'), 124.7 (11, 11'), 139.3 (12, 12'), 136.6 (13, 13'), 133.6 (14, 14'), 130.5 (15, 15'), 27.7 (1, 1'-gem-Me), 13.7 (5, 5'-Me), 12.5 (9, 9'-Me), 12.7 (13, 13'-Me) (Ref. 0061)	m/z: 564 (M, 100%), 549 (M-15, 20.6%), 508 (M-56, 8.4%), 484 (M-80, 9.4%), 472 (M-92, 44.9%), 458 (M-106, 12.2%) (Ref. 0059/0136) FD-MS m/z: 564 (100%), 282 (M²⁺, 1%) (Ref. 1053)		RF-TLC on 0.25 mm RP-18 layers (Merck, Art. 15423) using several ratio of light petroleum (bp 40-60C)-acetonitrile-methanol ex: 1:6:3 Rf=0.29, 3:1:6 Rf=0.57 (Ref. 0135) HPLC (column: Sperisorb S 5-CN 0.3150 cm, eluent: hexane/isopropyl ethanoate/2-propanol/N-ethyldiiopropylamine 82.4:17:0.5:0.1, flow: 1.0 ml/min) Retention time: 610 sec (Ref. 0420)	Phoenicoparrus andinus, Phoenicoparrus jamesi, Phoenicoparrus ruber (plasma, feathers) (Ref. 0476), Eudocimus ruber (plasma, shin, feathers) (Ref. 0477) Daphinia madna (Ref. 0478/0481), Hydra littoralis, Hydra pirardi (Ref. 0479), Artemia salina (Ref. 0483/0482), Stichopus japonicus, Holothuria leucospilota, Holothuria moebi, Holothuria pervicax, Cucumaria japonica, Cucumaria echinata, Pentacta australis (Ref. 0454) Psolus fabrichii (Ref. 0471) Thamnocephalus platyurus, Streptocephalus torvicornis, Branchinella kugenumaenis, Branchinecta lindahli, Chirocephalus diaphanus (Ref. 0484), Botryococcus braunii (Ref. 1081) Oncoryhnchus rhodurus (integuments and muscle) (Ref. 0472) Oncoryhnchus masou macrostomus , Salmo gairdneri (integuments) (Ref. 0473) Bradyrhizobium sp. strains (aerobic photosynthetic bacteria) (Ref. 1121/1156)	Racemic a-ionone was transformed into the the 4-oxo-b-ionone via the 4,5-epoxide. Successive Grignard reaction with vinyl magnesium chloride, halogenation, and reaction with a sodium sulphinate gave the 4-oxo-C15-sulphone, which was transformed to the corresponding ketal. Reaction with the C10-dialdehyde, reduction with sodium dithionite/NH3, deprotection, and isomerization gave (all-E)-canthaxanthin. (Ref. 0019) 4-Oxo-C15-phosphonium salt was prepared via the reaction of 2,6,6-3-isobutoxy-2-cyclohexenone with the protected (E)-methylpent-2-en-4-yn-1-ol, or via the reaction of 2,6,6-trimethyl-2-cyclohexenone with 3-(1-ethoxyethoxy)-3-methyl-1-penten-4-yne. Wittig reaction with the C15-phosphonium salt with the C10-dialdehyde provided canthaxanthin. (Ref. 0134) 6-Ethylenedioxy-3,3-diemthyloctan-2-one, derived from the half-ester acid chloride of a,a-dimethylglutaric acid, was condensed with crocetin-dial, deprotected and then cylized with alkali to provide canthaxanthin. (Ref. 0139) b-Ionone was transformed into dehydro-retro-C19-aldehyde, which was condensed with acetylene using i-PrMgBr and treated with AcOH to provide 4,4-diacetoxy-15,15'-dehydro-b-carotene. Hydrolysis, Oppennauer-oxidation, partial hydrogenation and successive isomerization gave canthaxanthin. (Ref. 0138) 4-Acetoxy-retinal was condensed with retinyltriphenylphosphonium sulfate to yield the acetate of isocryptoxanthin, which was treated with 68% HBr to give dehydro-retro-carotene. This was treated with NBS and AcOH to yield the acetate of isozeaxanthin, which was converted to canthaxanthin. (Ref. 0121)	Phoenicoparrus ruber (flamingo): b-Carotene echinenone canthaxanthin (Ref. 0480) Daphinia madna: b-Carotene echinenone canthaxanthin (Ref. 0481) Artemia salina (brine shrimp): b-Carotene echinenone canthaxanthin (Ref. 0482/0483) Botryococcus braunii (green alga): b-Carotene echinenone canthaxanthin (Ref. 0485) Salmo gairdneri (rainbow trout): canthaxanthin echinenone b-carotene (Ref. 0487/0406/0407) Salmo salar (salomn): canthaxanthin echinenone b-carotene (Ref. 0406/0407) Tilapia nilotica (tilapia): canthaxanthin b-carotene retinol (Ref. 0417/0216) Micropterus salmoides (black bass): canthaxanthin 3-dehydroretinol (Ref. 0216) Plecoglossus altivelis (ayu): canthaxanthin 3-dehydroretinol (Ref. 0216) Rat: canthaxanthin 3-dehydroretinol (Ref. 0216) Astaxanthin and canthaxanthin are accumulated in lipoidal globules of Scenedesmus komarekii (Chlorophyceae, Chlorophyta) cultured under high light intensity and nitrogen limitaion (Ref. 1147).	A gene required for the biosynthesis of canthaxanthin from b-carotene was isolated from the marine bacteria, Agrobacterium aurantiacum and Alcaligenes sp. strain PC-1 (present name; Paracoccus sp. N81106 and MBIC03024, respectively), and the function of the gene was determined (Ref. 0202/1008). b-Carotene is converted to canthaxanthin by the dioxygenation enzyme CrtW (b-carotene ketolase) by way of echinenone under the presence of O₂, Fe²⁺, and 2-oxoglutarate (Ref. 0205/1002). The corresponding gene was also isolated from Haematococcus pluvialis (green alga) (Ref. 0203/1011). All of the genes for canthaxanthin synthesis (crtE, crtB, crtI, crtY and crtW) is isolated from Bradyrhizobium sp. strain ORS278 (aerobic photosynthetic bacterium) and functionaly identified (Ref. 1121), and this bacterium also has spirilloxanthin synthesis genes (Ref. 1284).	Semi-empirical molecular orbital calculations using AM1 Hamiltonian (MNDO-AM1 method) were performed in order to predict their stable structures (Ref. 1337).	[0019] / [0059] / [0061] / [0092] / [0093] / [0121] / [0134] / [0135] / [0136] / [0138] / [0139] / [0202] / [0203] / [0205] / [0213] / [0215] / [0216] / [0217] / [0219] / [0226] / [0230] / [0406] / [0407] / [0417] / [0420] / [0441] / [0454] / [0471] / [0472] / [0473] / [0476] / [0477] / [0478] / [0479] / [0480] / [0481] / [0482] / [0483] / [0484] / [0487] / [0489] / [0490] / [0491] / [0492] / [1002] / [1008] / [1011] / [1053] / [1081] / [1121] / [1147] / [1156] / [1284] / [1337]
41		Lutein G	(3S,3'R,6'S)-b,e-Carotene-3,3'-diol	VCA0041	Masayoshi Ito		C₄₀H₅₆O₂	568.871			145-147C (Ref. 0452)						lmax (nm): petrol 420, 444, 472 (Ref. 0452)		¹-NMR d (300MHz, CDCl3): 0.85 s (3H, 16'-H), 0.94 s (3H, H-17'), 1.07 s (6H, H-16, 17), 1.39 d,d (1H, H-2'ax), 1.48 d,d (1H, H-2ax), 1.64 s (3H, H-18'), 1.65 d,d(1H, H-2'eq), 1.74 s (3H, H-18), 1.91 s (3H, H-19'), 1.97 s (9H, H-19, 20, 20'), 2.04 d,d (1H, H-4ax), 2.39 d,d (1H, H-4eq), 2.16 d (1H, H-6'), 4.00 m (1H, H-3), 4.23 m (1H, H-3'), 5.48 br.s (1H, H-4'), 5.53 d,d (1H, H-7'), 6.1-6.7 (13H, olefinic H) (Ref. 0452)	m/z: 568 (M), 550 (M-18), 532 (M-18-18) (Ref. 0452)	CD data in EPA solution: De 220 (-2.0), 245 (-11.2), 272 (0), 288 (+5.5), 308 (0), 333 (-3.1), 370 (-0.5) [Spectrum 0028] (Ref. 0452)		Podothecus sachi (integuments) (Ref. 0452), Epinephelus fario (integuments) (Ref. 0452)					[0452]
42		Eschscholtzxanthone	(3'S)-3'-Hydroxy-4',5'-didehydro-4,5'-retro-b,b-caroten-3-one	VCA0042	Masayoshi Ito		C₄₂H₅₂O₂	588.861		Antioxidative activity (Ref. 0460)							lmax (nm): ether 480 (Ref. 0460)	nmax(KBr)/cm^-¹: 3400 (OH), 1660 (conj. C=O), 973, 950 (retro type olefin) (Ref. 0450)	¹H-NMR d(300 MHz, CDCl3): 1.25 (3H, s, 16'-Me), 1.39(6H, s, 16',17'-Me), 1.45 (3H, s, 17'-Me), 1.51 (1H, dd J 12, 8, 2'ax-H), 1.81 (1H, dd J 12, 5, 2'eq-H), 1.95 (3H, d J1.5, 18'-Me), 1.97 (6H, s, 19', 20'-Me), 2.00 (3H, s, 20'-Me), 2.03 (3H, s, 19'-Me), 2.159 (3H, d J 1, 18-Me), 2.40 (2H, s, 2-H), 4.35 (1H, m, H-3'), 5.94 (1H, br.s, 4-H), 6.26-6.91 (14H, olefinic H) (Ref. 0460)	m/z: 564 (M, 18%), 546 (20%), 532 (8%), 454 (6%), 119 (100%), 107 (76%), 91(78%) (Ref. 0460)	CD data in ether solution: De 232 (+4.0), 240 (0), 272 (+5.7), 285(0), 318(-7.2), 345 (0), 390 (+5.0) (Ref. 0460)		Taxus caspidata (berries) (Ref. 0460)		Taxus caspidata: Eschscholtzxanthin eschscholtzxanthone rhodoxanthin(Ref. 0460>			[0450] / [0460]
43		4-Ketolutein D	(3S,3'S,6'S)-3,3'-Dihydroxy-b,e-caroten-4-one	VCA0043	Masayoshi Ito		C₄₀H₅₄O₃	582.855									lmax (nm): ether 454 - 470 (Ref. 0475)		¹H-NMR d(300 MHz, CDCl3): 0.85 (3H, s, 16'-Me), 1.00 (3H, s, 17'-Me), 1.21 (3H, s, 16-Me), 1.32(3H, s, 17-Me), 1.63 (3H, d, 18'-Me), 1.95 (3H, s, 18-Me), 3.68 (1H, d, OH), 4.32 (1H, dd, H-3), H1.97 (6H, s, 19', 20'-Me), 2.00 (3H, s, 20'-Me), 2.03 (3H, s, 19'-Me), 2.159 (3H, d J 1, 18-Me), 2.40 (2H, s, 2-H), 4.25 (1H, m, 3'-H), 5.43 (1H, dd, 7'-H), 5.55 (1H, br.s, 4-H), 6.1-6.7 (13H, olefinic H) (Ref. 0475)	m/z: 582 (M), 564 (M-18) (Ref. 0475)	CD data in ether solution: De 220 (10.0), 240 (0), 252 (+1), 260(0), 290(-13.5), 335 (0), 355 (+1.0) (Ref. 0475)		Branchiostegus japonicus (integuments) (Ref. 0475)		Branchiostegus japonicus: Astaxanthins 4-ketozeaxanthins 4-ketoluteins luteins tunaxanthins (Ref. 0475)			[0475]
44		4-Ketolutein F	(3S,3'R,6'S)-3,3'-Dihydroxy-b,e-caroten-4-one	VCA0044	Masayoshi Ito		C₄₀H₅₄O₃	582.855									lmax (nm): ether 454 - 470 (Ref. 0475)			m/z: 582 (M), 564 (M-18) (Ref. 0475)	CD data in ether solution: De 225 (-2.0), 248 (-6.0), 260(0), 275(-5.5), 335 (-2), 360 (-5.5) (Ref. 0475)		Branchiostegus japonicus (integuments) (Ref. 0475)		Branchiostegus japonicus: Astaxanthins 4-ketozeaxanthins 4-ketoluteins luteins tunaxanthins (Ref. 0475)			[0475]
45		Capsanthin	(3R,3'S,5'R)-3,3'-Dihydroxy-b,k-caroten-6'-one	VCA0045	Masayoshi Ito		C₄₀H₅₆O₃	584.871		Inhibitotory effect on Epstein-Barr virus activation (anti-tumor promotion) (Ref. 0217) Singlet oxygen quenching activity (Ref. 0441) Anti-tumore promoting effect (Ref. 1095) Anti-oxidative activity (Ref. 1096) Suppressing efect of generation of superoxide and nitric oxide (Ref. 1097)	178C (Ref. 0140)						lmax (nm) (E ¹^%₁_c_m): hexane 288 (353), 355 (147), 452sh (1675), 470 (1965), 497 (1560) (Ref. 0140)	nmax(KBr)/cm^-¹: 3446m (OH), 1666m (conj. C=O), 1580s, 1555s, 1518s (conj. C=C), 1053s, 1009s, 967s (Ref. 0140)	¹H-NMR d(400 MHz, CDCl3): 0.84 (3H, s, 16'-Me), 1.08 (6H, s, 16,17-Me), 1.21 (3H, s, 17'-Me), 1.37(3H, s, 18'-Me), 1.74 (3H, s, 18-Me), 1.96 (3H, s, 19'-Me), 1.97 (6H, s, 19,20-Me), 1.99 (3H, s, 20'-Me), 2.39 (1H, ddd, J 17, 6, 1.5, 4a-H), 2.96 (1H, dd, J 15.5, 9, 4'a-H), ca. 4.00 (1H, br m, 3-H), 4.52 (1H, m, 3'-H), 6.13 (2H, s, 7,8-H), 6.16 (1H, d, J 11.6, 10-H), 6.26 (1H, d, J 11, 14-H), 6.35 (1H, d, J 11, 14'-H), 6.36 (1H, d, J 15, 12-H), 6.45 (1H, d, J 15, 7'-H), 6.52 (1H, d, J 15, 12'-H), 6.55 (1H, d, J 11, 10'-H), ca. 6.6-6.8 (4H, m, 11,11',15,15'-H), 7.33 (1H, d, J 15, 8'-H) (Ref. 0140) ¹³C-NMR d(100.6 MHz, CDCl3): 12.75 (C19), 12.79 (C20), 12.84 (C19'), 12.90 (C20'), 21.39 (C18'), 21.63 (C18), 25.16 (C17'), 25.95 (C16'), 28.80 (C16), 30.32 (C17), 42.69 (C4), 44.01 (C1'), 45.49 (C4'), 48.61 (C2), 51.06 (C2'), 59.01 (C5'), 65.14 (C3), 70.44 (C3'), 121.04 (C7'), 124.13 (C11'), 125.58 (C11), 125.93 (C7), 126.30 (C5), 129.74 (C15'), 131.27 (C10), 131.68 (C15'), 132.39 (C14), 133.69 (C9'), 135.24 (C14'), 135.93 (C13'), 137.46 (C12), 137.60 (C13), 137.85 (C6), 138.51 (C8), 140.63 (C10'), 141.97 (C12'), 146.86 (C8'), 202.82 (C6') (Ref. 0140)	m/z: 584 (75, M), 478 (62), 429 (6), 145 (51), 127 (36), 109 (100), 106 (31), 105 (44), 91 (65), 83 (56) (Ref. 0140)	CD in dioxane: De 356 (+1.65), 337sh (+0.51), 319sh (-0.92), 300 (-6.48), 294 sh (-5.91), 276sh (-1.30), 256 (+4.55), 247sh (+3.25), 240sh (+0.99), 226 (-3.71) (Ref. 0140)	TLC [Kieselgel F254 (Merck); CHCl3-acetone 9:1) Rf = 0.22 (Ref. 0140) HPLC (columun: Chromsil C18 6mm end-capped, detection at 450nm, eluent 12% (v/v) H2O in MeOH (A), MeOH (B), 50% (v/v) acetone in MeOH (C). The gradient program was 100% A, 8min, to 80% A/20% B in 8 min, to 50% A/50% B in 8min, to 100% B in 7 min, 100% B, 2min, to 100% C in 6min, 100% C, 5min (linear steps), The flow rate was 1.5 mL/min. capsanthin 3,6-epoxide tR=16 min, capsanthin tR=17min, cryptpcapsin tR=32 min. (Ref. 0506) HPLC (columun: Sheriosorb ODS 2, 250X4mm i.d. 5 mm, flow rate 1.5ml/min, detection 450nm, solvent system (A) hexane-EtOAc-EtOH-acetone (96:3:2:2); (B) light petrolum ether -acetone-diethylamine (10:4:1); (C) CH2Cl2-EtOAc (4:1), solvent A, B, C gradient, gradient program in text, capsorubin tR=3.49, capsanthin tR=6.35 min, capsanthin tR=17min, cryptpcapsin tR=11.85 min. (Ref. 0507)	Capsicum annuum (red paprika) (Ref. 0142)	Aldol condensation between (3R)-3-hydroxy-8'-b-apo-carotenal and [(1R,4S)-4-hydroxy-1,2,2-trimethylcyclopentyl]methylketone with sodium hydride as a base provided capsanthin. (Ref. 0140)	Zeaxanthin antheraxanthin capsanthin in Capsicum annuum (Ref. 0515) in Caosicum annuum chrmoplastes (Ref. 0514) Changes in carotenoid composition and content during ripening of selective cultivars for paprika (Capsicum annuum) production (Ref. 1271).	The capsanthin-capsorubin synthase (CCS) gene was isolated from Capsicum annuum (red pepper) in 1994 (Ref. 1023). It is considered that capsanthin is synthesized from antheraxanthin by CCS.		[0140] / [0217] / [0441] / [0506] / [0507] / [0514] / [0515] / [1023] / [1095] / [1096] / [1097] / [1271]
46		Capsorubin	(3S,5R,3'S,5'R)-3,3'-Dihydroxy-k,k-carotene-6,6'-dione	VCA0046	Masayoshi Ito		C₄₀H₅₆O₄	600.870		Singlet oxygen quenching activity (Ref. 0441) Anti-tumore promoting effect (Ref. 1095) Anti-oxidative activity (Ref. 1096) Suppressing efect of generation of nitric oxide (Ref. 1097)	214-216C (Ref. 0140) 216-217C (Ref. 0141)						lmax (nm) (E ¹^%₁_c_m): hexane 297 (310), 423sh (845), 445 (1528), 471 (2218), 505 (1985) (Ref. 0140); benzene 303 (284), 435sh (746), 445 (1528), 461 (1303), 487 (1838), 521 (1635) (Ref. 0140/0141>	nmax(KBr)/cm^-¹: 3464s (OH), 1669s (conj. C=O), 1588s, 1556s (conj. C=C), 1055s, 983s (Ref. 0140/0141)	¹H-NMR d(400 MHz, CDCl3): 0.84 (6H, s, 16,16'-Me), 1.21 (6H, s, 17,17'-Me), 1.37 (6H, s, 18,18'-Me), 1.48 (2H, dd, J 14.5, 4, 4b,4'b-H), 1.71 (2H, dd, J 13.5, 4, 2b,2'b-H), 1.96 (6H, s, 19,19'-Me), 1.99 (6H, s, 20,20'-Me), 2.00 (2H, dd, J 13.5, 7, 2a,2'a-H), 2.96 (2H, dd, J 14.5, 8.5, 4a,4'a-H), 4.51 (2H, m, 3,3'-H), 6.36 (2H, m, 14,14'-H), 6.45 (2H, d, J 15, 7,7'-H), 6.52 (2H, d, J 14.5, 12,12'-H), 6.55 (2H, d, J 11, 10,10'-H), 6.64 (2H, dd, J 14.7, 11, 11,11'-H), 6.69 (2H, m, 15,15'-H), 7.32 (2H, d, J 15, 7,7'-H) (Ref. 0140) ¹³C-NMR d(100.6 MHz, CDCl3): 12.88 (C19,19',20,20'), 21.37, 25.15, 25.93 (C16,16',17,17',18,18'), 44.02 (C1,1'), 45.44 (C4,4'), 51.02 (C2,2'), 59.03 (C6,6'), 70.42 (C3,3'), 121.23 (C7,7'), 124.67 (C11,11'), 146.76 (C8,8'), 202.87 (C6,6') (Ref. 0140/0061)	m/z: 600 (10, M), 494 (9), 445 (5), 221 (10), 145 (16), 127 (48), 109 (100), 106 (15), 105 (15), 91 (28), 83 (46) (Ref. 0140/0141)	CD in dioxane: De 374 (-3.13), 366sh (-2.94), 358sh (-2.64), 339sh (-1.30), 331sh (-0.91), 301 (+6.14), 290sh (+4.10), 268sh (+0.11), 258sh (-1.00), 252 (-1.47), 249 (-1.41), 239sh (-1.13), 224sh (+0.61) (Ref. 0140/0141)	TLC [Kieselgel F254 (Merck); CHCl3-acetone 9:1) Rf = 0.15 (Ref. 0140) HPLC (columun: Chromsil C18 6mm end-capped, detection at 450nm, eluent 12% (v/v) H2O in MeOH (A), MeOH (B), 50% (v/v) acetone in MeOH (C). The gradient program was 100% A, 8min, to 80% A/20% B in 8 min, to 50% A/50% B in 8min, to 100% B in 7 min, 100% B, 2min, to 100% C in 6min, 100% C, 5min (linear steps), The flow rate was 1.5 mL/min. capsanthin 3,6-epoxide tR=16 min, capsanthin tR=17min, cryptpcapsin tR=32 min. (Ref. 0506) HPLC (columun: Sheriosorb ODS 2, 250X4mm i.d. 5 mm, flow rate 1.5ml/min, detection 450nm, solvent system (A) hexane-EtOAc-EtOH-acetone (96:3:2:2); (B) light petrolum ether -acetone-diethylamine (10:4:1); (C) CH2Cl2-EtOAc (4:1), solvent A, B, C gradient, gradient program in text, capsorubin tR=3.49, capsanthin tR=6.35 min, capsanthin tR=17min, cryptpcapsin tR=11.85 min. (Ref. 0507)	Capsicum annuum (red paprika) (Ref. 0142)	Aldol condensation between crocetindialdehyde and [(1R,4S)-4-hydroxy-1,2,2-trimethylcyclopentyl]methylketone with sodium hydride as a base provided capsorbin. (Ref. 0019/0140)	Zeaxanthin violaxanthin capsorubin in Capsicum annuum (Ref. 0515) in Caosicum annuum chrmoplastes (Ref. 0514) Changes in carotenoid composition and content during ripening of selective cultivars for paprika (Capsicum annuum) production (Ref. 1271).	The capsanthin-capsorubin synthase (CCS) gene was isolated from Capsicum annuum (red pepper) in 1994 (Ref. 1023). It is considered that capsorubin is synthesized from violaxanthin by CCS.		[0019] / [0061] / [0140] / [0141] / [0441] / [0506] / [0507] / [0514] / [0515] / [1023] / [1095] / [1096] / [1097] / [1271]
47		Cryptocapsin	(3'S,5'R)-3'-Hydroxy-b,k-caroten-6'-one	VCA0047	Masayoshi Ito		C₄₀H₅₆O₂	568.871			172-174C (Ref. 0140)						lmax (nm) (E ¹^%₁_c_m): hexane 284 (390), 354 (260), 452sh (1780), 472 (2110), 494sh (1685) (Ref. 0140); benzene 289 (328), 462sh (1510), 485 (1810), 506sh (1525) (Ref. 0140)	nmax(KBr)/cm^-¹: 3440m (OH), 1668s (conj. C=O), 1580s, 1558s,1516s (conj. C=C), 1055s,1007s, 968s (Ref. 0140)	¹H-NMR d(400 MHz, CDCl3): 0.84 (3H, s, 16'-Me), 1.03 (6H, s, 16,17-Me), 1.21 (3H, s, 17'-Me), 1.37 (3H, s, 18'-Me), 1.72 (3H, s, 18-Me), 1.96 (3H, s, 19'-Me), 1.98 (6H, s, 19,20-Me), 1.99 (3H, s, 20'-Me), 2.96 (1H, dd, J 14.5, 8.7, 4'a-H), 4.51 (1H, m, 3'-H), 6.14 (1H, d, J 16.3, 8-H), ca. 6.15 (1H, 10-H), 6.19 (1H, d, J 16.3, 7-H), 6.26 (1H, br d, J 11, 14-H), ca. 6.36 (2H, m, 12,14'-H), 6.44 (1H, d, J 15, 7'-H), 6.52 (1H, d, J 15, 12'-H), 6.55 (1H, d, J 11, 10'-H), ca. 6.58-6.74 (4H, m, 11,11',15,15'-H), 7.33 (1H, d, J 15, 8'-H) (Ref. 0140) ¹³C-NMR d(100.6 MHz, CDCl3): 12.72, 12.78, 12.82, 12.87 (C19,19'20,20'), 19.28 (C3), 21.35 (C18'), 21.77 (C18), 25.10, 25.89 (C16',17'), 28.99 (C16, 17), 33.14 (C4), 34.28 (C1), 39.69 (C2), 43.95 (C1'), 45.31 (C4'), 50.89 (C2'), 58.91 (C5'), 70.24 (C3'), 120.91 (C7'), 124.04 (C11'), 125.71 (C11), 126.97 (C7), 129.46 (C5), 129.60 (C15), 130.82 (C10), 131.73 (C15'), 132.22 (C14), 133.58 (C9'), 135.36 (C14'), 135.79 (C13'), 136.47 (C9), 137.09 (C12?), 137.68 (C13), 137.74 (C8?), 137.94 (C6), 140.76 (C10'), 142.05 (C12'), 146.90 (C8'), 202.94 (C6') (Ref. 0140)	[Spectrum 0032] Maoka Takashi	CD in dioxane: De 365 (-1.14), 355sh (-0.90), 348sh (-0.74), 332sh (-0.30), 318sh (-0.04), 294 (+2.52), 289sh (+2.37), 268sh (+0.45), 257sh (-0.37), 254 (-0.45), 241sh (-0.45), 238 (-0.84), 229 (+0.11) (Ref. 0140)	TLC [Kieselgel F254 (Merck); CHCl3-acetone 9:1) Rf = 0.45 (Ref. 0140) HPLC (columun: Chromsil C18 6mm end-capped, detection at 450nm, eluent 12% (v/v) H2O in MeOH (A), MeOH (B), 50% (v/v) acetone in MeOH (C). The gradient program was 100% A, 8min, to 80% A/20% B in 8 min, to 50% A/50% B in 8min, to 100% B in 7 min, 100% B, 2min, to 100% C in 6min, 100% C, 5min (linear steps), The flow rate was 1.5 mL/min. capsanthin 3,6-epoxide tR=16 min, capsanthin tR=17min, cryptpcapsin tR=32 min. (Ref. 0506) HPLC (columun: Sheriosorb ODS 2, 250X4mm i.d. 5 mm, flow rate 1.5ml/min, detection 450nm, solvent system (A) hexane-EtOAc-EtOH-acetone (96:3:2:2); (B) light petrolum ether -acetone-diethylamine (10:4:1); (C) CH2Cl2-EtOAc (4:1), solvent A, B, C gradient, gradient program in text, capsorubin tR=3.49, capsanthin tR=6.35 min, capsanthin tR=17min, cryptpcapsin tR=11.85 min. (Ref. 0507)	Capsicum annuum (red paprika) (Ref. 0142)	Aldol condensation between 8'-b-apo-carotenal and [(1R,4S)-4-hydroxy-1,2,2-trimethylcyclopentyl]methylketone with sodium hydride as a base provided cryptocapsin. (Ref. 0140)				[0140] / [0506] / [0507]
48		Capsanthin 3,6-epoxide	(3S,5R,6R,3'S,5'R)-3,6-Epoxy-5,3'-dihydroxy-5,6-dihydro-b,k-caroten-6'-one	VCA0048	Masayoshi Ito		C₄₀H₅₆O₄	600.870		Anti-tumore promoting effect (Ref. 1095) Anti-oxidative activity (Ref. 1096) Suppressing efect of generation of superoxide and nitric oxide (Ref. 1097)	169-170C (Ref. 0504)						lmax (nm) : benzene 507, 481 (Ref. 0505)		¹H-NMR d(400 MHz, CDCl3): 0.84 (3H, s, 16'-Me), 0.88 (3H, s 17-Me), 1.20 (3H, s 17'-Me), 1.21 (3H, s, 18-Me), 1.36 (3H, s, 18'-Me), 1.43 (3H, s 16-Me), 1.48 (1H, dd, J 14.5, 3.3, 4'-Hb), 1.61 (1H, d, J 11.6, 2-Heq), 1.67 (1H, d, J 11.9, 4-Heq), 1.71 (1H, dd, J 13.8, 4.7, 2-Hb), 1.84 (1H, ddd, J 11.6, 6, 2.4, 2-Hax), 1.99 (1H, dd, J 13.8, 7.8, 2-Heq), 1.95 (6H, s, 19, 19'-Me), 1.97 (3H, s, 20'-Me), 1.98 (3H, s, 20-Me), 2.00 (1H, dd, J 13.5, 7, , 2'-Ha), 2.06 (1H, ddd, J 11.9, 6.0, 2.4, 4-Hax), 2.95 (1H, dd, J 14.5, 8.5, 4'-Ha),4.39 (1H, t, J 6, 3-H), 4.51 (1H, m, 3'-H), 5.75 (1H, d, J16.1, 7-H), 6.20 (1H, d, J 11.5, 10-H), 6.26 (1H, m, 14-H), 6.35 (1H, m, 14'-H), 6.36 (1H, d, J 14.7, 12-H), 6.37 (1H, d, J 16.1, 8-H), 6.44 (1H, d, J 15.2, 7'-H), 6.51 (1H, d, J 14.5, 12'-H), 6.61 (1H, dd, J 11, 14.5, 11'-H), ca. 6.62 (1H, m, 15-H), 6.65(1H, dd, J11.5, 14.7, 11-H), 6.69 (1H, m, 15'-H), 7.33 (1H, d, J 15.2, 8'-H) (Ref. 0505) ¹³C-NMR d(100.6 MHz, CDCl3): 12.73 (C20'), 12.84 (C20), 12.86 (C19,19'), 21.28 (C18'), 25.08 (C17'), 25.72 (C16), 25.85 (C16'), 31.57 (C18), 32.15 (C17), 43.96 (C1'), 43.98 (C 1), 45.30 (C4'), 47.71 (C4), 48.49 (C2), 58.85 (C2'), 58.93 (C5'), 70.36 (C3'), 75.73 (C3), 82.47 (C5), 91.64 (C6), 120.87 (C7'), 123.10 (C7), 124.08 (C11'), 125.40 (C11), 129.72 (C15), 131.51 (C15'), 131.61 (C10), 132.43 (C14), 133.63 (C9'), 134.82 (C8), 135.20 (C9), 135.23 (C14'), 135.92 (C13), 137.51 (C13'), 137.60 (C12), 140.70 (C10'), 141.96 (C12'), 146.86 (C8'), 202.91 (C6') (Ref. 0505)	m/z: 600 (8, M), 582 (2), 494 (13), 229 (8), 286 (7), 221 (28), 181 (16), 160 (14), 155 (14), 145 (28), 119 (22), 109 (100) (Ref. 0505)	CD in EPA: De 243 (-1.34), 281 (+3.38), 353 (-1.31)(Ref. 0505)	HPLC (columun: Chromsil C18 6mm end-capped, detection at 450nm, eluent 12% (v/v) H2O in MeOH (A), MeOH (B), 50% (v/v) acetone in MeOH (C). The gradient program was 100% A, 8min, to 80% A/20% B in 8 min, to 50% A/50% B in 8min, to 100% B in 7 min, 100% B, 2min, to 100% C in 6min, 100% C, 5min (linear steps), The flow rate was 1.5 mL/min. capsanthin 3,6-epoxide tR=16 min, capsanthin tR=17min, cryptpcapsin tR=32 min. (Ref. 0506)	Capsicum annuum (red paprika) (Ref. 0504/0505)		Zeaxanthin antheraxanthin capsanthin capsanthin 5,6-epoxide capsanthin 3,6-epoxide in Capsicum annuum (red paprika) (Ref. 0504/0506)			[0504] / [0505] / [0506] / [1095] / [1096] / [1097]
49		7,8-Didehydroastaxanthin	(3S,3'S)-3,3'-dihydroxy-7,8-Didehydro-b,b-carotene-4,4'-dione	VCA0049	Masayoshi Ito		C₄₀H₅₀O₄	594.823			211-212C (Ref. 0143)						lmax (nm) (e): benzene 300sh (16,466), 330 (16,481), 493 (102,913) (Ref. 0143); pyridine 324 (20,175), 496 (109,336), 520sh (96,320) (Ref. 0143); CS2 480sh (83,718), 507 (103,546), 540sh (81,515) (Ref. 0143)	nmax(KBr)/cm^-¹: 3506m (OH), 2160m (acetylene), 1664s (conj. C=O), 1564m (conj. C=C), 1374m, 1365m (gem. dimethyl), 1079s (OH), 970s (trans CH=CH) (Ref. 0143)	¹H-NMR d(400 MHz, CDCl3): 1,211, 1.323 (16',17'-Me), 1.312, 1.356 (16,17-Me), 1.801 (t, J 13.4, 2ax-H), 1.811 (t, J 13.4, 2'ax-H), 1.945 (18'-Me), 1.976 (20-Me), 1.999 (20'-Me), 2.003 (19'-Me), 2.026 (8-Me), 2.047 19-Me), 2.16 (dd, J 12.6, 5.6, 2'eq-H), 2.22 (dd, J 12.6, 5.5, 2eq-H), 3.610 (d, J 1.6, 3-OH), 3.682 (d, J 1.8, 3'-OH), 4.30-4.36 (2H, m, 3'ax, 3ax-H), 6.222 (d, J 16, 7'-H), 6.28-6.70 (11H, 10',14,14',8',12,12',11,10,11',15,15'-H) (Ref. 0143) ¹³C-NMR d(67.892 MHz, CDCl3): 12.59 (19'Me), 12.74, 12.85 (20,20'-Me), 13.99 (18'-Me), 14.33 (18-Me), 17.60 (19-Me), 26.15, 30.74 (16',17'-Me), 26.18, 31.04 (16,17-Me), 36.63 (1C), 36.80 (1'C), 44.20 (2C), 45.47 (2'C), 69.21, 69.32 (3,3'C), 88.01, 110.99 (7,8C), 117.43 (9C), 123.41, 123.77, 124.86, 126.87, 130.52, 131.27, 133.60, 133.72, 134.73, 134.95, 135.14, 136.32, 137.13, 138.99, 139.65, 140.62, 142.30 (9',11,11',15,15',5,5',14,14',13,13',10,10',12,12',8',7'C), 147.71 (6C), 162.18 (6'C), 199.28 (4C) (Ref. 0143)	m/z: 594 (65, M), 592 (26), 578 (18), 576 (19), 203 (93), 119 (67), 105 (70), 91 (100) (Ref. 0143)	CD: De 372 (+4.02), 317 (-14.13), 300sh (-11.3), 275 (+3.78), 263sh (+1.0), 247 (-3.35), 224 (+4.10) (Ref. 0143)	TLC [Kieselgel F254 (Merck); CH2Cl2-ether 4:1) Rf = 0.20 (Ref. 0143) HPLC (column: Spherisorb S 5-CN 0.3150 cm, eluent: hexane/isopropyl ethanoate/2-propanol/N-ethyldiisopropylamine, 82.4:17:0.5:0.1, flow rate: 1 ml/min) [Chromatogram 0021] --- di-(-)-camphanate tR = 1168 sec [all-E-(3R,3'S)], 1406 sec [all-E-(3S,3'S)] (Ref. 0420) HPLC (column: Sperisorb S 5-CN 0.3150 cm, eluent: hexane/isopropyl ethanoate/2-propanol/N-ethyldiiopropylamine 82.4:17:0.5:0.1, flow: 1.0 ml/min) Retention time: 914 sec (Ref. 0420)	Asterias rubens (Starfish) (Ref. 0420) Asterina pectinifera, Asterias amurensis (Starfish) (Ref. 0423) Watasenia scintilans, Sepia modokai, Sepia officinales (cuttlefish) (Ref. 0424) Octopus vulgaris, Octopus ocellatus, Octopus minor (octopus) (Ref. 0424) Salmo salar, Oncorhynchus sp. (Salmon) (Ref. 0419) Paralithodes brevipes (crab) (Ref. 0469)	Wittig condensation between (3S)-3-hydroxy-4-oxo-C15-phosphonium salt and (3S)-3-Hydroxy-7,8-didehydro-4-oxo-12'-apo-b-carotenal provided 7,8-didehydroastaxanthin. (Ref. 0143)	Doatoxanthin 7,8-didehydroastaxanthin Asterias rubens (Starfish) (Ref. 0420) Diatoxanthin 4,4'-dihydroxydiatoxanthin 4-keto-4'-hydroxydiatoxanthin 7,8-didehydroastaxanthin in Asterina pectinifera, Asterias amurensis (Starfish) (Ref. 0423)			[0143] / [0419] / [0420] / [0423] / [0424] / [0469]
50		7,8,7',8'-Tetradehydroastaxanthin	(3S,3'S)-3,3'-Dihydroxy-7,8,7',8'-tetradehydro-b,b-carotene-4,4'-dione	VCA0050	Masayoshi Ito		C₄₀H₄₈O₄	592.807			216-218C (Ref. 0143)						lmax (nm) (e): benzene 300 (16,818), 326 (16,820), 466sh (85,489), 493 (111,417), 524 (89,974) (Ref. 0143); CHCl3 300 (19,416), 330 (19,420), 498 (119,729), 526sh (99,666) (Ref. 0143)	nmax(KBr)/cm^-¹: 3495m (OH), 2160m (acetylene), 1669s (conj. C=O), 1580m, 1560m (conj. C=C), 1379m, 1365m (gem. dimethyl), 1079s (OH), 970s (trans CH=CH) (Ref. 0143)	¹H-NMR d(400 MHz, CDCl3): 1.311, 1.355 (each 6H, s, 16,16',17,17'-Me), 1.805 (t, J 13.3, 2ax,2'ax-H), 1.811 (t, J 13.4, 2'ax-H), 1.984 (20,20'-Me), 2.026 (18,18'-Me), 2.048 19,19'-Me), 2.220 (dd, J 12.8, 5.6, 2eq,2'eq-H), 3.610 (d, J 1.5, 3,3'-OH), 4.33 (ddd, J 13.4, 5.6, 1.4, 3ax,3'ax-H), 6.34 (d, J 9, 14,14'-H), 6.44-6.65 (6H, 12,12',11,11',10,10'-H), 6.69 (dd, J 8,3, 15,15'-H) (Ref. 0143) ¹³C-NMR d(67.892 MHz, CDCl3): 12.80 (20,20'-Me), 14.31 (18,18'-Me), 17.62 (19,19'-Me), 26.28, 31.11 (16,16',17,17'-Me), 36.71 (1,1'C), 44.44 (2,2'C), 69.42 (3,3'C), 88.12, 110.87 (7,7',8,8'C), 117.76 (9,9'C), 124.04 (11,11'C), 131.14 (15,15'C), 133.84 (5,5'C), 134.78 (14,14'C), 136.77 (13,13'C), 138.87, 140.56 (10,10',12,12'C), 147.64 (6,6'C), 199.29 (4,4'C) (Ref. 0143)	m/z: 592 (75, M), 590 (57), 486 (7), 296 (20), 145 (40), 106 (47), 105 (49), 91 (100), 83 (52) (Ref. 0143)	CD: De 359 (+1.31), 313 (-4.45), 279sh (-3.2), 255 (+4.19) (Ref. 0143)	TLC [Kieselgel F254 (Merck); CH2Cl2-ether 4:1) Rf = 0.22 (Ref. 0143) HPLC (column: Spherisorb S 5-CN 0.3150 cm, eluent: hexane/isopropyl ethanoate/2-propanol/N-ethyldiisopropylamine, 82.4:17:0.5:0.1, flow rate: 1 ml/min) [Chromatogram 0021] --- di-(-)-camphanate tR = 1071 sec [all-E-(3R,3'S)], 1289 sec [all-E-(3S,3'S)] (Ref. 0420) HPLC (column: Sperisorb S 5-CN 0.3150 cm, eluent: hexane/isopropyl ethanoate/2-propanol/N-ethyldiiopropylamine 82.4:17:0.5:0.1, flow: 1.0 ml/min) Retention time: 798 sec (Ref. 0420)	Asterias rubens (Starfish) (Ref. 0420) Asterina pectinifera, Asterias amurensis (Starfish) (Ref. 0423) Watasenia scintilans, Sepia modokai, Sepia officinales (cuttlefish) (Ref. 0424) Octopus vulgaris, Octopus ocellatus, Octopus minor (octopus) (Ref. 0424) Salmo salar, Oncorhynchus sp. (Salmon) (Ref. 0419) Paralithodes brevipes (crab) (Ref. 0469)	Wittig condensation between the C10-diphosphonium salt and (3S)-3-acyloxy-7,8-didehydro-4-oxo-C15-aldehyde provided 7,8,7',8'-tetradehydroastaxanthin. (Ref. 0143)	Alloxanthin 7,8,7',8'-tetradehydroastaxanthin Asterias rubens (Starfish) (Ref. 0420) Alloxanthin 4,4'-dihydroxyalloxanthin 4-keto-4'-hydroxyalloxanthin 7,8,7',8'-tetradehydroastaxanthin in Asterina pectinifera, Asterias amurensis (Starfish) (Ref. 0423)			[0143] / [0419] / [0420] / [0423] / [0424] / [0469]
51		Alloxanthin/ Tetradehydrozeaxanthin / (Cynthiaxanthin)/ (Pectenoxanthin)	(3R,3'R)-7,8,7',8'-Tetradehydro-b,b-carotene-3,3'-diol	VCA0051	Masayoshi Ito		C₄₀H₅₂O₂	564.840		Inhibitotory effect on Epstein-Barr virus activation (anti-tumor promotion) (Ref. 0217)	186C (Ref. 0145)						lmax (nm): hexane 480, 451 (Ref. 0145); ethanol 481, 452 (Ref. 0145); benzene (e) 492, 462 (131,000) (Ref. 0145); methanol [Spectrum 1152]	nmax(KBr)/cm^-¹: 3350, 2170vw, 1560, 1450, 1050, 1020, 960, 950	¹H-NMR d(CDCl3): 1.14, 1.19 (1-gem-Me), 1.90 (5-Me), 1.99 (9-Me), 1.94 (13-Me), 1.94 (13'-Me), 1.99 (9'-Me), 1.90 (5'-Me), 1.19, 1.14 (1'-gem-Me), 1.50 (2H, s), 2.29 (4H, d, J 7) (Ref. 0145) ¹³C-NMR d(CDCl3): 36.9 (1,1'C), 46.7 (2,2'C), 64.8 (3,3'C), 41.5 (4,4'C), 137.2 (5,5'C), 124.3 (6,6'C), 89.1 (7,7'C), 98.8 (8,8'C), 119.1 (9,9'C), 138.0 (10,10'C), 124.3 (11,11'C), 135.2 (12,12'C), 136.4 (13,13'C), 133.4 (14,14'C), 130.3 (15,15'C), 24.8 and 30.5 (1,1'-gem-Me), 22.4 (5,5'-Me), 18.0 (9,9'-Me), 12.7 (13,13'-Me) (Ref. 0061)	m/z: 564 (10, M), 549 (1), 546 (<0.5, M-18), 528 (<0.5, M-18-18), 472 (4, M-92), 457 (1), 406 (3), 105 (12), 92 (75), 91 (100) (Ref. 0145)	CD in EPA: De 210 (-7.0), 280 (-3.0), 325 (-1.8), 492 (0) (Ref. 0426) 255 (0), 290 (-2), 350 (+0.5) (Ref. 0518)		Cynthia roretzi (Sea squirt) (Ref. 0493) Halocynthia roretzi (Sea suirt) (Ref. 0401/0402) Mytilus edulis (Shell fish) (Ref. 0426) Mytilus corusucus (Ref. 0427) Patinopecten yessoensis (Scallop) (Ref. 0494) Pecten maximus (Scallop) (Ref. 0496) Scapharca broughtonii (Shell fish) (Ref. 0495) Marine Shell Fishes (Ref. 0430) Asterina pectinifera, Asterias amurensis (Starfish) (Ref. 0423) Carassius auratus (gold fish) (integuments) (Ref. 0470) Oncorhynchus masou macrostomus, Salmo gairdneri (trout) (Ref. 0473)	The Wittig reaction between the C10-dialdehyde and an excess of the 3-acetoxy-7,8-didehydro-C10-phosphonium salt in the presence of KOH in propan-2-ol at -30C leads to the racemic all-E alloxanthin and its 9Z isomer. (Ref. 0145)				[0061] / [0145] / [0217] / [0401] / [0402] / [0423] / [0426] / [0427] / [0430] / [0470] / [0473] / [0493] / [0494] / [0495] / [0496] / [0518]
52		Diatoxanthin/ 7,8-Didehydrozeaxanthin	(3R,3'R)-7,8-Didehydro-b,b-carotene-3,3'-diol	VCA0052	Masayoshi Ito		C₄₀H₅₄O₂	566.856		Inhibitotory effect on Epstein-Barr virus activation (anti-tumor promotion) (Ref. 0217)	203C (Ref. 0146)						lmax (nm): hexane 479, 450 (Ref. 0145); acetone 430, 453 (E ¹^%₁_c_m=2720, e=154000), 480, %III/II=42 (Ref. 0146)	nmax(KBr)/cm^-¹: 3376s (OH), 3027-2825s (CH), 2171w (acetylene), 1446m, 1360m, 1050s, 959s (Ref. 0146)	¹H-NMR d(CDCl3): 1.16, 1.21 (1-gem-Me), 1.91 (5-Me), 1.99 (9-Me), 1.96 (13-Me), 1.96 (13'-Me), 1.96 (9'-Me), 1.74 (5'-Me), 1.09 (1'-gem-Me), 1.50 (2H, s) (Ref. 0145) ¹H-NMR d(CDCl3): 1.073 (16',17'-Me), 1.147 (16-Me), 1.200 (17-Me), 1.45 (m, 2ax-H), 1.48 (m, 27ax-H), 1.736 (18'-Me), 1.77 (m, 2'eq-H), 1.84 (m, 2eq-H), 1.923 (18-Me), 1.952 (20-Me), 1.968 (20'-Me), 1.975 (19'-Me), 2.005 (20-Me), 2.00-2.10 (m, 4ax,4'ax-H), 2.38 (dd, J 15.6, 5.4, 4'eq-H), 2.43 (dd, J 16.6, 4.4, 4eq-H), 4.00 (m, 3,3'-H), 6.10-6.25 (m, 7',8'-H), 6.16 (d, J 11.2, 10'-H), 6.25 (d, J 10.3, 14'-H), 6.27 (d, J 10.8, 14-H), 6.35 (d, J 14.8, 12-H), 6.36 (d, J 15.1, 12'-H), 6.46 (d, J 11.3, 10-H), 6.52 (dd, J 14.2, 11.3, 11-H), 6.62-6.68 (m, 11',15,15'-H) (Ref. 0146) ¹³C-NMR d(CDCl3): 12.8 (19',20,20'-Me), 18.1 (19-Me), 21.7 (18'-Me), 22.5 (18-Me), 28.7 (16,16'-Me), 30.3 (17,17'-Me), 36.6 (1C), 37.1 (1'C), 41.4 (4C), 42.5 (4'C), 46.7 (2C), 48.4 (2'C), 64.8 (3C), 65.2 (3'C), 89.0 (7C), 98.6 (8C), 118.9 (9C), 124.1 (11C), 124.2 (6C), 125.1 (11'C), 125.6 (7'C), 126.2 (14'C), 129.9 (15'C), 130.5 (15C), 131.3 (10'C), 132.5 (14'C), 133.5 (14C), 135.2 (10C), 135.8 (9'C), 136.1 (13'C), 136.8 (13C), 137.3 (5C), 137.5 (12'C), 137.7 (6'C), 138.1 (12C), 138.5 (8'C) (Ref. 0146)		CD: De 216 (-6.5), 224 (-5.9), 239 (0), 252 (+4.5), 264 (0), 289 (-10.1), 319 (0), 347 (+2.8) (Ref. 0146)		Halocynthia roretzi (Sea suirt) (Ref. 0401/0402) Mytilus edulis (Shell fish) (Ref. 0426) Asterina pectinifera, Asterias amurensis (Starfish) (Ref. 0423) Carassius auratus (gold fish) (integuments) (Ref. 0470) Oncorhynchus masou macrostomus, Salmo gairdneri (trout) (Ref. 0473) Mytilus edulis (Shell fish) (Ref. 0426) Mytilus corusucus (Ref. 0427) Pecten maximus (Scallop) (Ref. 0238) Patinopecten yessoensis (Scallop) (Ref. 0494) Scapharca broughtonii (Shell fish) (Ref. 0495) Marine Shell Fishes (Ref. 0430) Bacillariophyceae (Diatoms) (Ref. 0497)	The Wittig reaction between the (3R)-3-hydroxy-C25-phosphonium salt and the (3R)-3-hydroxy-7,8-didehydro-C15-aldehyde in the presence of NaH in CH2Cl2 leads to (3R,3'R)-diatoxanthin (Ref. 0146).	Diatoxanthin - pectenolone (Pecten maximus) (Ref. 0238)			[0145] / [0146] / [0217] / [0238] / [0401] / [0402] / [0423] / [0426] / [0427] / [0430] / [0470] / [0473] / [0494] / [0495] / [0497]
53		Fucoxanthinol	(3S,5R,6S,3'S,5'R,6'R)-5,6-Epoxy-3,3',5'-trihydroxy-6',7'-didehydro-5,6,7,8,5',6'-hexahydro-b,b-caroten-8-one	VCA0053	Masayoshi Ito		C₄₀H₅₆O₅	616.870		Inhibitotory effect on Epstein-Barr virus activation (anti-tumor promotion) (Ref. 0217)							lmax (nm): acetone (420), 445, (465) (Ref. 0148)	nmax(KBr)/cm^-¹: 3248s (OH), 3031-2734s (CH), 1929w (C=C=C), 1726w, 1650m (conj. C=O), 1606s, 1530w, 1385s (gem Me), 1294w, 1270w, 1149m, 1123m, 1071m, 1052m, 965w (trans CH=CH) (Ref. 0148)	¹H-NMR d(CDCl3): 0.9631, 1.035 (1-gem-Me), 3.82 (3-H), 1.79 (4ax-H), 2.30 (4eq-H), 1.220 (5-Me), 2.60, 3.66 (7-H2), 1.943 (9-Me), 7.15 (10-H), 6.58 (11-H), 6.67 (12-H), 1.990 (13-Me), 6.41 (14-H), 6.64 (15-H), 6.75 (15'-H), 6.27 (14'-H), 1.990 (13'-Me), 6.35 (12'-H), 6.61 (11'-H), 6.12 (10'-H), 1.810 (9'-Me), 6.03 (8'-H), 1.336 (5'-Me), 4.32 (3'-H), 1.351, 1.070 (1'-gem-Me) (Ref. 0148) (Ref. 1309)			TLC [Kieselgel 60 (Merck Art. 7731)]: acetone-hexane 3:7, Rf = 0.08; acetone-hexane 1:1, Rf = 0.20 (Ref. 0148)	Tapes philippinarum (Clam) (Ref. 0403) Psammechinus miliaris (sea-urchin) (Ref. 0500) Algae (Ref. 0409)		Fucoxanthin - Fucoxanthinol in Psammechinus miliaris (sea-urchin) (Ref. 0500) In lying hens, fucoxanthin in Fucus serratus (brown algae) is metabolized to fucoxanthinol, and then fucoxanthinol 3'-sulphate and paracentrone (Ref. 1309).			[0148] / [0217] / [0403] / [0409] / [0500] / [1309]
54		19'-Hydroxyfucoxanthin 19'-hexanoate/ 19'-Hexanoyloxyfucoxanthin	(3S,5R,6S,3'S,5'R,6'S)-5,6-Epoxy-3'-ethanoyloxy-19'-hexanoyloxy-3,5'-dihydroxy-6',7'-didehydro-5,6,7,8,5',6'-hexahydro-b,b-caroten-8-one	VCA0054	Masayoshi Ito		C₄₈H₆₈O₈	773.049									lmax (nm): acetone 423, 450, (478) (Ref. 0149); acetone 445, (480) (Ref. 0151); methanol 443 (Ref. 0149)	nmax(KBr)/cm^-¹: 3400 (OH), 3040-2860 (CH), 1930 (allene), 1730 (C=O ester), 1660 (conj. C=O), 1640, 4580, 1530, 1460, 1380, 1360, 1250 (ester), 1200, 1160 (tert. OH), 1040 (OH and ester), 970 (trans CH=CH), 920, 730 (Ref. 0149)	¹H-NMR d(CDCl3): 0.97, 1.04 (16, 17-Me), 1.20 (18-Me), 1.92 (19-Me), 1.96 (20, 20'-Me), 4.78 (19'-CH2), 1.37 (18'-Me), 1.10 (17'-Me), 1.26 (16'-Me), 2.66, 3.63 (each d, 7-CH2), 6.04 (8-H), 2.00 (OAc), 8.2 (ca 2H, t, J 7, CH2COO) (Ref. 0149)	m/z: 772 (M), M-18, M-20, M-34, M-36, M-60, M-78, M-96, M-110, M-114, M-116, M-132, M-134, M-150, M-174, M-194 (Ref. 0149) m/z: 792 (0.2, M), 754 (0.4, M-18), 274 (59), 178 (100) (Ref. 0426)	CD spactrum in EPA [Spectrum 0031] (Ref. 0150)	TLC [special plate]: hexane-acetone-iso propanol 68.5:30:1.5, Rf = 0.30 (Ref. 0426) HPLC (nitrile columun, hexane-isopropyl acetate-acetone-methanol 77:17:7:0.5) Rt=6.53 (Ref. 0426)	Coccolithus huxleyi (haptophyte algae) (Ref. 0149) Phaenocystis sp. (Prymnesiophcea algae) (Ref. 0498) Mytilus edulis (Shell fish) (Ref. 0404)					[0149] / [0150] / [0404] / [0426] / [0498]
55		19'-Hydroxyfucoxanthinol 19'-hexanoate/ 19'-Hexanoyloxyfucoxanthinol	(3S,5R,6S,3'S,5'R,6'R)-5,6-Epoxy-19'-hexanoyloxy-3,3',5'-trihydroxy-6',7'-didehydro-5,6,7,8,5',6'-hexahydro-b,b-caroten-8-one	VCA0055	Masayoshi Ito		C₄₈H₆₈O₈	773.049									lmax (nm): acetone 444, 468 (Ref. 0426)			m/z: 730 (20, M), 712 (9, M-18), 111 (100) (Ref. 0426)		TLC [special plate]: hexane-acetone-iso propanol 68.5:30:1.5, Rf = 0.20 (Ref. 0426) HPLC (nitrile columun, hexane-isopropyl acetate-acetone-methanol 77:17:7:0.5) Rt=10.08 (Ref. 0426)	Phaenocystis sp. (Prymnesiophcea algae) (Ref. 0498) Mytilus edulis (Shell fish) (Ref. 0404)					[0404] / [0426] / [0498]
56		19'-Hydroxyisomytiloxanthin 19'-hexanoate/ 19'-Hexanoyloxyisomytiloxanthin	(5R,6R,3'R)-19'-Hexanoyloxy-6,3'-dihydroxy-7',8'-didehydro-5,6,7,8-tetrahydro-b,b-carotene-3,8-dione	VCA0056	Masayoshi Ito		C₄₆H₆₄O₆	712.997									lmax (nm): acetone 450, (470) (Ref. 0426)		¹H-NMR (400 MHz, CDCl3) in mixture with excess isomytiloxanthin showed a singlet at d 4.95, attributed to 19'-CH2 (Ref. 0426)	m/z: 712 (2, M), 694 (2, M-18), 281 (100) (Ref. 0426)		TLC [SiO2]: 40% acetone in hexane, Rf = 0.68 (Ref. 0426) HPLC (nitrile columun, hexane-isopropyl acetate-acetone-methanol 77:17:7:0.5) Rt=5.37 (Ref. 0426)	Mytilus edulis (Edible Mussel)(Ref. 0426)					[0426]
57		19'-Hydroxyfucoxanthin 19'-butanoate/ 19'-Butanoyloxyfucoxanthin	(3S,5R,6S,3'S,5'R,6'S)-5,6-Epoxy-3'-ethanoyloxy-19'-butanoyloxy-3,5'-dihydroxy-6',7'-didehydro-5,6,7,8,5',6'-hexahydro-b,b-caroten-8-one	VCA0057	Masayoshi Ito		C₄₆H₆₄O₈	744.996									lmax (nm): hexane (426), 446, 473 (Ref. 0147); acetone (423), 446, 472 (Ref. 0147); CHCl3 456, 481 (Ref. 0147)	nmax(KBr)/cm^-¹:3430s (OH), 2960s, 2930s, 2860s (CH), 1930w (C=C=C), 1730s (C=O, ester), 1660m (conj. C=O), 1610m, 1580w (C=C), 1530m, 1465s (CH2), 1380m, 1365m (CH3), 1250m (CO-O-C), 1190w, 1175m (tert. OH), 1080w, 1055w, 1030m (sec. OH), 970s (trans CH=CH) (Ref. 0147)	¹H-NMR d(400 MHz, CDCl3): 1.354 (2ax-H), 1.500 (2eq-H), 3.820 (3-H), 1.785 (4ax-H), 2.324 (4eq-H), 2.603, 3.658 (7-H2), 7.149 (10-H), 6.590 (11-H), 6.673 (11-H), 6.415 (14-H), 6.663 (15-H), 1.037 (16ax-Me), 0.964 (17eq-Me), 1.222 (18-Me), 1.948 (19-Me), 1.999 (20-Me), 1.386 (2'ax-H), 1.976 (2'eq-H), 5.367 (3'H), 1.490 (4'ax-H), 2.263 (4'eq-H), 6.060 (8'-H), 6.308 (10'-H), 6.679 (11'-H), 6.422 (12'-H), 6.308 (14'-H), 6.749 (15'-H), 1.384 (16'ax-Me), 1.078 (17'eq-H), 1.378 (18'-Me), 4.810, 4.758 (19'-H2), 1.977 (20'-Me), 2.282 (t, J 7.4), 1.655 (sext., J 7.4), 0.942 (t, J 7.4) (COCH2CH2CH3) (Ref. 0028/0147) ¹³C-NMR d(CDCl3): 35.96, 36.27 (1,1'C), 47.08, 45.20 (2,2'C), 64.33, 67.86 (3,3'C), 41.67, 45.32 (4,4'C), 66.12, 72.70 (5,5'C), 67.05, 118.40 (6,6'C), 40.82, 201.67 (7,7'C), 197.86, 101.13 (8,8'C), 134.74, 129.49 (9,9'C), 138.96, 132.95 (10,10'C), 123.68, 124.51 (11,11'C), 144.86, 139.92 (12,12'C), 135.95, 137.67 (13,13'C), 136.40, 133.56 (14,14'C), 130.23, 132.20 (15,15'C), 25.04, 29.06 (16ax,16'ax-Me), 28.12, 31.85 (17eq,17'eq-Me), 21.16, 30.97 (18,18'-Me), 11.83, 59.20 (19-Me, 19'-CH2), 12.79, 12.93 (20,20'-Me) (Ref. 0028)	m/z: 744 (M, 0.8), 726 (M-18, 6), 710 (M-16-18, 2), 708 (M-18-18, 3), 666 (M-18-60, 0.9), 664 (M-80, 0.4), 656 (M-88, 0.5), 650 (M-16-18-60, 0.6), 648 (M-18-18-60, 0.7, 640 (M-16-88, 0.3), 638 (M-18-88, 0.2), 630 (1), 622 (M-16-18-88, 1), 620 (M-18-18-88, 0.6), 580 (M-16+60-88, 0.6), 562 (M-16-18-60-88, 0.7), 560 (M-18-18-60-88, 0.8), 536 (1), 298 (33), 221 (20), 195 (100) (Ref. 0147)	CD in EPA: De 218 (-0.4), 227 (0), 233 (+0.3), 243 (0), 271 (-0.5), 291 (0), 332 (+0.5), ca. 355-410 (0) (Ref. 0147)	HPLC (column: Si-5 4.6250 mm, eluent: 20% acetone in hexane-0.1% MeOH, flow rate: 1.5 ml/min) Rt=19.2 min (Ref. 0147)	Mytilus edulis (Edible Mussel) (Ref. 0426) Phaenocystis sp. (Prymnesiophcea algae) (Ref. 0498)					[0028] / [0147] / [0426] / [0498]
58		Echinenone/ (Myxoxanthin)	b,b-Caroten-4-one	VCA0058	Masayoshi Ito		C₄₀H₅₄O₁	550.856		Inhibitotory effect on Epstein-Barr virus activation (anti-tumor promotion) (Ref. 0217). Native subunit cytochrome b₆ is purified from a monomeric cytochrome b₆f complex of Synechocystis sp. PCC 6803 (cyanobacterium), and it containes one echinenone, one chlorophyll a and two b-type hemes (Ref. 1098). The cytochrome b₆f complex from the crtO-less mutant of Synechocystis sp. PCC 6803 contains b-carotene, b-cryptoxanthin or zeaxanthin insted of echinenone (Ref. 1335). By feeding experiments of Pseudocentrotus depressus (sea urchin), echinenone increases the fertilization, hatching and survival rate, and decreases the malformation rates (Ref. 1285).	178-179C (Ref. 0121) 187C (Ref. 0139)						lmax (nm): cyclohexane 461 (E ¹^%₁_c_m = 2110) (Ref. 0121); ethanol 466 (Ref. 0152); methanol 460 (Ref. 1222/1346); methanol [Spectrum 1110]	nmax(KBr)/cm^-¹: 1657s (conj. CO), 1550m (C=C), 1003m, 966vs (trans CH=CH) (Ref. 0139)	¹H-NMR d(300 MHz, CDCl3): allE-isomer, 6.23 (7-H), 6.17 (7'-H), 6.38 (8-H), 6.16 (8'-H), 6.28 (10-H), 6.15 (10'-H), 6.66 (11-H), 6.65 (11'-H), 6.44 (12-H), 6.36 (12'-H), 6.31 (14'-H), 6,25 (15-H), 6.64 (15'-H), 1.201 (16, 17-Me), 1.035 (16', 17'-Me), 1.880 (18-Me), 1.725 (18'-Me), 2.005 (19-Me), 1.981 (19'-Me), 1.984 (20-Me), 1.984 (20'-Me) (Ref. 0523) ¹H-NMR d(300 MHz, CDCl3): 9'Z-isomer, 6.23 (7-H), 6.20 (7'-H), 6.38 (8-H), 6.68 (8'-H), 6.28 (10-H), 6.06 (10'-H), 6.66 (11-H), 6.77 (11'-H), 6.43 (12-H), 6.29 (12'-H), 6.31 (14'-H), 6,25 (15-H), 6.64 (15'-H), 1.201 (16, 17-Me), 1.035 (16', 17'-Me), 1.881 (18-Me), 1.762 (18'-Me), 2.005 (19-Me), 1.981 (19'-Me), 1.984 (20-Me), 1.984 (20'-Me) (Ref. 0523)	m/z: 564 (100, M), 458 (6) (Ref. 0152)(Ref. 0059)			Rhizobium lupini (soil and root nodule bacterium) (Ref. 0152) Botryococcus braunii (Botryococcaceae, Chlorococcales) (Ref. 1081) Synechocystis sp. PCC 6803 (Ref. 1222), Anabaena sp. PCC 7120, Anabaena variabilis IAM M3 and Nostoc punctiforme PCC 73102 (Ref. 1346), Gloeobacter violaceus (Ref. 1347) (cyanobacteria). Psammechinus miliaris (Ref. 0500), Pseudocentrotus depressus (Ref. 0501), and 9-Z-Echinenone Pseudocentrotus depressus (sea-urchin) (Ref. 0523). Sea-urchins (Ref. 0410/0502/0503).	6-Ethylenedioxy-3,3-diemthyloctan-2-one, derived from the half-ester acid chloride of a,a-dimethylglutaric acid, was condensed with 8'-b-apo-carotenal, deprotected and then cylized with alkali to provide echinenone. (Ref. 0139) 4-Acetoxy-retinal was condensed with retinyltriphenylphosphonium sulfate to yield the acetate of isocryptoxanthin, which was saponified and then oxidized by the Oppenauer method to yield echinenone. (Ref. 0014/0121)	b-carotene - echinenone in Psammechinus miliaris (sea-urchin) (Ref. 0500) in Pseudocentrotus depressus (sea-urchin) (Ref. 0501)	The b-carotene ketolase gene (crtO), which was isolated from the cyanobacterium Synechocystis PCC6803, encoded an enzyme catalyzing the conversion of b-carotene to echinenone (Ref. 1024/1222).		[0014] / [0059] / [0121] / [0139] / [0152] / [0217] / [0410] / [0500] / [0501] / [0502] / [0503] / [0523] / [1024] / [1081] / [1098] / [1222] / [1285] / [1335] / [1346] / [1347]
59		Neoxanthin	(3S,5R,6R,3'S,5'R,6'S)-5',6'-Epoxy-6,7-didehydro-5,6,5',6'-tetrahydro-b,b-carotene-3,5,3'-triol	VCA0059	Masayoshi Ito		C₄₀H₅₆O₄	600.870		Component of LHC II in higher plants (Ref. 0154). Crystal structure of spinach major light-harvesting complex (LHCII) contains 2 lutein, 1 9'-cis neoxanthin, 1 (violaxanthin, antheraxanthin or zeaxanthin), 8 chlorophyll a, and 6 chlorophyll b per monomer (Ref. 1291). A light-harvesting pigment-protein complex (LHC) of Pseudoscourfieldia marina (Micromonadophyceae = Pracinophyceae) contains 5 prasinoxanthin, 2 neoxanthin, 1 unknown carotenoid, 9 Chl b, 6 Chl a, 2 MgDV (mol) (Ref. 1136). Inhibitotory effect on Epstein-Barr virus activation (anti-tumor promotion) (Ref. 0217). Singlet oxygen quenching activity (Ref. 0441) .	136-139C (Ref. 0153)						lmax all-E form (nm) (e): ethanol 471 (137900), 442, (142810), 418 (96180), 329 (10560), 265 (33930) (Ref. 0153); benzene 482 (111520), 452 (117070), 426 (77590), 336 (8172), 274 (16450) (Ref. 0153) lmax 9'-cis form: MeOH/water (9/1) 413, 435, 464 ; all-trans form: 417, 440, 470 [Spectrum 1111] (Ref. 0154) lmax 9'-cis form: benzene 418, 442, 472 nm, %III/II=84; acetone 414, 438, 466 nm, %III/II=73 (Ref. 1182)		¹H-NMR d(400 MHz, CDCl3) all-E form: 4.32 (m, 3-H), 3.92 (m, 3'-H), 2.27 (ddd, J 12.8, 4.1, 2.1, 4eq-H), 2.39 (ddd, J 14.2, 5.0, 1.8, 4'eq-H), 5.88 (d, J 15.5, 7'-H), 6.04 (s, 8-H), 6.30 (d, J 15.5, 8'-H), 6.12 (d, J 11.3, 10-H), 6.20 (d, J 11.6, 10'-H), 6.34 (d, J 15.6, 12-H), 6.38 (d, J 14.5, 12'-H), 6.25 (d, J 11.1, 14-H), 6.25 (d, J 11.1, 14'-H), 6.63 (m, 15-H), 6.63 (m, 15'-H), 1.07 (16-Me), 0.98 (16'-Me), 1.34 (17-Me), 1.16 (17'-Me), 1.35 (18-Me), 1.19 (18'-Me), 1.81 (19-Me), 1.93 (19'-Me), 1.97 (20-Me), 1.97 (20'-Me) and 9'-Z form (Ref. 0153) ¹H-NMR d(400 MHz, CDCl3 and CD3OD) 9'-E form (Ref. 1182) ¹H-NMR d (500 MHz, CDCl3) 9'-cis form: ca. 1.93 (2eq-H), 1.63 (dd, 2'eq-H), 1.36 (2ax-H), 1.235 (d, J 3.0, 2'-ax-H), 4.32 (m, 3-H), 1.29 (d, J 1.5, 3-OH), 3.92 (m, 3'-H), ca. 1.26 (3'-OH), 2.263 (ddd, J 12.9, 4.1, 2.1, 4eq-H), 2.408 (ddd, J 14.3, 5.0, 1.8, 4'eq-H), 1.406 (4ax-H), 1.66 (dd, 4'ax-H), 5.935 (d, J 15.5, 7'-H), 6.032 (s, 8-H), 6.836 (d, J 15.5, 8'-H), 6.116 (d, J 10.5, 10-H), 6.075 (d, J 11.5, 10'-H), 6.544 (dd, J 11.5, 15.0, 11-H), 6.759 (dd, J 11.8, 14.8, 11'-H), 6.339 (d, J 15.0, 12-H), 6.292 (d, J 15.0, 12'-H), 6.242 (d, J 9.5, 14-H), 6.242 (d, J 9.5, 14'-H), 6.62 (m, 15-H), 6.62 (m, 15'-H), 1.068 (16-Me), 1.008 (16'-Me), 1.334 (17-Me), 1.165 (17'-Me), 1.350 (18-Me), 1.255 (18'-Me), 1.800 (19-Me), 1.933 (19'-Me), 1.957 (20-Me), 1.963 (20'-Me) (Ref. 0154)	FD-MS m/z: 600 (Ref. 0154)	CD in EPA all-E form: De 219 (0), 225 (-1.8), 243 (-0.7), 265 (-2.8), 293 (-0.6), 311 (-0.8), ca. 350 (+0.1) (Ref. 0153) CD in EtOH: De 227 (-2.7), 241 (-1.28), 266 (-4.77), 303 (-0.57), 313 (-0.77), 335 (0), 341 (+2.4), ca. 359 (0), 377 (+3.9), 400 (+0.68), 419 (+0.79), 441 (+1.17), 463 (+0.71) ca. 479 (0) (Ref. 0153) Excited-state dynamics of all-trans and 9'-cis neoxanthin were investigated using the fluorescence up-conversion method: their absorption spectra and the fluorescence lifetimes of the second singlet excited-state were the same (Ref. 1112).	HPLC, mBondapak C18 column (8*100 mm, RCM type, Waters), eluent methanol/water 9/1, 2.0 ml/min: all-trans form 7.9 min, 9'-cis form 8.5 min (Ref. 0154) HPLC of Mesostigma viride (Prasinophyceae) (Ref. 1250)	Major carotenoids of oxygenic phototrophs: the 9'-cis form, but not the all-trans form, is found in chloroplasts of seed plants, ferns, mosses and green algae, all of which contain chlorophylls a and b. In contrast, neoxanthin is not found in other algal classes, such as Heterokontophyta, Rhodophyta and onygenic phototrophic prokaryotes. In non-photosynthetic organs, such as petals and fruits, the presence of neoxanthin is classified into four types; those having only the 9'-cis form, those with only the all-trans form, those with both forms, and those without either form (Ref. 0154). Botryococcus braunii (Green algae) (Ref. 1081) Higher plants (Ref. 0409) green algae (Ref. 0409) Prasinophytes (algae) (Ref. 0513)	The optically active 3-hydroxy-5,6-epoxy-C15-aldehyde was reacted with the acetylenic C10-diphosphonate and the resulting C25-phosphonate was next condensed with the optically active C15-allenic aldehyde to give the 15,15'-didehydro-neoxanthin which, after partial hydrogenation and isomerization, gave all-E neoxanthin. (Ref. 0019)	All-trans neoxanthin is the substrate of violaxanthin de-epoxidase, but 9'-cis neoxanthin is not (Ref. 1143/1144). 9-Cis epoxy-carotenoids (9'-cis neoxanthin and 9-cis violaxanthin) are cleaved to xanthoxin, which is a precursor of abscisic acid (plant hormone), by nine-cis epoxy-carotenoid dioxygenase (NCED) or neoxanthin cleavage enzyme (NCE) of maize and tomato (Ref. 1157/1158/1159). Similar enzyme, carotenoid cleavage dioxygenase (CCD), cleaves carotenoids symmetrically to produce a C14 dialdehyde and two C13 products (Ref. 1159). [Table 1029]	A gene for neoxanthin synthase (NSY and NXS) is cloned and functionaly identified from Lycopersicum esculentum (tomato) and Solanum tuberosum (potato), respectively, and both have homology to lycopene b-cyclase (CrtL-b or LCY-b) and capsanthin capsorubin synthase (CCS) (Ref. 1125/1126). This enzyme synthesises neoxanthin from violaxanthin, but it seems not to have isomerise activity, all-trans form to 9-cis form (S. Takaichi).	All-trans form is isolated from pumpkin fruit, and 9'-cis from leaves (Ref. 0154/1112). Mesostigma viride (Prasinophyceae) has only all-trans form not 9'-cis form (Ref. 1250).	[0019] / [0153] / [0154] / [0217] / [0409] / [0441] / [0513] / [1081] / [1112] / [1125] / [1126] / [1136] / [1143] / [1144] / [1157] / [1158] / [1159] / [1182] / [1250] / [1291]
60		Violaxanthin	(3S,5R,6S,3'S,5'R,6'S)-5,6:5',6'-Diepoxy-5,6,5',6'-tetrahydro-b,b-carotene-3,3'-diol	VCA0060	Masayoshi Ito		C₄₀H₅₆O₄	600.870		Inhibitotory effect on Epstein-Barr virus activation (anti-tumor promotion) (Ref. 0217) Singlet oxygen quenching activity (Ref. 0441) Fucoxanthin-chlorophyll a/c-protein assembly (FCPA) with energy transfer activity from fucoxanthin to chlorophyll a and from chlorophyll c to chlorophyll a isolated from Dictyota dichotoma (brown alga); 10 fucoxanthin, 1 violaxanthin, no b-carotene, 3 chlorophyll c, 13 chlorophyll a and a 54 kDa protein to form a 4.8 S complex (Ref. 1115).	198-199C (Ref. 0155)						lmax (nm) (e): EPA 265.5 (37500), 414.5 (102600), 437 (152500), 467 (150000) (Ref. 0155); methanol 326, 415, 436, 466, %III/II=89.9 [Spectrum 1112] (Ref. 1052)		¹H-NMR d(400 MHz, CDCl3): 0.98 (s, 16-Me), 1.16 (s, 17-Me), 1.19 (s, 18-Me), 1.25 (dd, J 12.5, 11, 2ax-H), 1.63 (dd, J 14.5, 8.8, 4ax-H), 1.63 (ddd, J 12.5, 3.5, 1.8, 2eq-H), 1.93 (s, 19-Me), 1.97 (s, 20-Me), 2.39 (ddd, J 14.3, 5, 1.8, 4eq-H), 3.92 (m, 3-H), 5.88 (d, J 15.5, 7-H), 6.20 (d, J 11, 10-H), 6.27 (m, 14-H), 6.30 (d, J 15.5, 8-H), 6.37 (d, J 15, 12-H), 6.61 (dd, J 15, 11, 11-H), 6.64 (m, 15-H) (Ref. 0155) ¹³C-NMR d(CDCl3, 25.16 MHz): 35.49 (1), 47.93 (2), 63.19 (3), 41.86 (4), 67.19 (5), 70.55 (6), 125.51 (7), 137.52 (8), 134.86 (9), 132.70 (10), 125.45 (11), 138.62 (12), 138.62 (13), 133.56 (14), 130.94 (15), 25.45 (16), 29.76 (17), 20.39 (18), 13.07 (19), 12.86 (20) (Ref. 0061/0156) 15-cis form (Ref. 0156)	CI-MS m/z: 601 (57, M+1), 583 (36, M+1-H2O), 565 (22, M-2H2O), 510 (35), 509 (M+1-toluene), 491 (30), 232 (15), 211 (27), 181 (100), 165 (21), 121 (20) (Ref. 0155) FD-MS m/z: 600 (100%) (Ref. 1053)	CD in EPA: De 212.5 (-6.2), 217.8 (0), 230 (+9.8), 240 (0), 264.5 (-27.9), 292 (0), 325 (5), 347 (0) (Ref. 0155); figure (Ref. 1235)		Botryococcus braunii (Green alage) (Ref. 1081) Higher plants (Ref. 0409) Prasinophytes (algae) (Ref. 0513)	The optically active 3-hydroxy-5,6-epoxy-C15-aldehyde was reacted with the acetylenic C10-diphosphonate to give the 15,15'-didehydro-violaxanthin which, after hydrogenation and iomerization, gave all-E violaxanthin. (Ref. 0019/0155)	zeaxanthin -> antheraxanthin -> violaxanthin (xanthophyll-cycle) in plant (Ref. 0512). Xanthophyll cycle is catalyzed by violaxanthin de-epoxidase, which is present in lumen of chloroplast in plant leaves, and whose pH optimum is pH 5.2 and requires ascorbate. pI is 5.4 (Ref. 1141). All-trans violaxanthin is the substrate of violaxanthin de-epoxidase, but cis forms are not (Ref. 1143/1144). 9-Cis epoxy-carotenoids (9'-cis neoxanthin and 9-cis violaxanthin) are cleaved to xanthoxin, which is a precursor of abscisic acid (plant hormone), by nine-cis epoxy-carotenoid dioxygenase (NCED) or neoxanthin cleavage enzyme (NCE) of maize and tomato (Ref. 1157/1159). Similar enzyme, carotenoid cleavage dioxygenase (CCD), cleaves carotenoids symmetrically to produce a C14 dialdehyde and two C13 products (Ref. 1159). [Table 1030]	The zeaxanthin epoxidase gene, which was isolated from higher plants, Nicotiana plumbaginifolia and Capsicum annuum (red pepper), encoded an enzyme catalyzing the conversion of zeaxanthin to violaxanthin by way of antheraxanthin under the presence of O₂, ferredoxin, and NADPH-ferredoxin redactase (Ref. 1025/1026). A gene of violaxanthin de-epoxidase, which catalyzes the conversion of violaxanthin to zeaxanthin by way of antheraxanthin (xanthophyll cycle), is cloned from romaine lettuce and expressed in Escherichia coli (Ref. 1142). Review of characteristics of zeaxanthin epoxidase and violaxanthin de-epoxidase (Ref. 1268)	Semi-empirical molecular orbital calculations using AM1 Hamiltonian (MNDO-AM1 method) were performed in order to predict their stable structures (Ref. 1337).	[0019] / [0061] / [0155] / [0156] / [0217] / [0409] / [0441] / [0512] / [0513] / [1025] / [1026] / [1052] / [1053] / [1081] / [1115] / [1141] / [1142] / [1143] / [1144] / [1157] / [1159] / [1235] / [1268] / [1337]
61		Cycloviolaxanthin	(3S,5R,6R,3'S,5'R,6'R)-3,6:3',6'-Diepoxy-5,6,5',6'-tetrahydro-b,b-carotene-5,5'-diol	VCA0061	Masayoshi Ito		C₄₀H₅₆O₄	600.870		Anti-oxidative activity (Ref. 1096)							lmax (nm): dioxan 332.2, 422.8, 446.4 476.8 (Ref. 0508); benzene 427, 453, 483 (Ref. 0509)		¹H-NMR d(600 MHz, CDCl3): 0.897 (6H, s 17,17'-Me), 1.226 (6H, s, 18,18'-Me), 1.447 (6H, s 16,16'-Me), 1.623 (2H, d, J 11.4, 2, 2'-Hendo), 1.685 (2H, d, J 12.1, 4, 4'-Hendo), 1.85 (2H, ddd, J 11.6, 6, 2.4, 2, 2'-Hexo), 1.961 (6H, s, 19, 19'-Me), 1.977 (6H, s, 20,20'-Me), 2.067 (2H, ddd, J 12.2, 6.1, 2.5, 4, 4'-Hexo), 4.402 (2H, t, J 6, 3,3'-H), 5.750 (2H, d, J 16.1, 7,7'-H), 6.207 (2H, d, J 11.1, 10,10'-H), 6.268 (2H, br. d, 14,14'-H), 6.367 (2H, d, J 15.0, 12,12'-H), 6.385 (2H, d, J 15.8, 8,8'-H), 6.62 (4H, m, 11,11',15,15'-H) (Ref. 0508) ¹³C-NMR d(100.6 MHz, CDCl3): 12.81 (C20, 20'), 12.85 (C19,19'), 25.73 (C17, 17'), 25.85 (C16, 16'), 31.60 (C18, 18'), 32.17 (C16, 16'), 44.01 (C1, 1'), 47.75 (C4, 4'), 48.53 (C2, 2'), 75.37 (C3, 3'), 82.50 (C5, 5'), 91.66 (C6, 6'), 124.83 (C11, 11'), 122.84 (C7, 7'), 130.11 (C15, 15'), 131.62 (C10, 10'), 132.67 (C14, 14'), 134.77 (C8, 8'), 134.89 (C9, 9'), 136.43 (C13, 13'), 137.81 (C12, 12') (Ref. 0509)	m/z: 600, 520, 221, 181(Ref. 0508)	CD in EPA: De 237 (-0.80), 272 (+0.81), 331 (-1.03), 417 (-1.13), 425 (-0.82), 446 (-1.84), 460 (-0.98), 472(-1.80) (Ref. 0508/0509)		Capsicum annuum (Red paprika) (Ref. 0508/0505)		Violaxanthin - cycloviolaxanthin in Capsicum annuum (Ref. 0511) Antheraxanthin - cucurbitaxanthin A - cucurbitaxanthin B - cycloviolaxanthinin in Capsicum annuum (Ref. 0511)			[0505] / [0508] / [0509] / [0511] / [1096]
62		Cucurbitaxanthin A	(3R,3'S,5'R,6'R)-3',6'-Epoxy-5',6'-dihydro-b,b-carotene-3,5'-diol	VCA0062	Masayoshi Ito		C₄₀H₅₆O₃	584.871		Inhibitotory effect on Epstein-Barr virus activation (anti-tumor promotion) (Ref. 0217) Anti-tumore promoting effect (Ref. 1095)							lmax (nm): benzene 487, 457, 434 (Ref. 0505); ether 423, 445, 473(Ref. 0510)	nmax(KBr)/cm^-¹: 3360m (OH), 2900s, 2850m, 1440w, 1379w, 1352w, 1292w, 1238w, 1085m, 1034m, 956s, 870w, 820w (Ref. 0510)	¹H-NMR d(400 MHz, CDCl3): 0.88 (3H, s, 17-Me), 1.07 (6H, s, 16', 17'-Me), 1.21 (3H, s, 18-Me), 1.43 (3H, s, 16-Me), 1.48 (1H, dd, J 12.0, 2'-Hax), 1.61 (1H, d, J 11.6, 2-Heq), 1.67 (1H, d, J 12.1, 4-Heq), 1.73 (3H, s, 18'-Me), 1.77 (1H, ddd, J 12.0, 3.6, 2.1, 2'-Heq), 1.84 (1H, ddd, J 11.5, 6, 2.2, 2-Hax), 1.95 (3H, s, 19-Me), 1.96 (9H, s, 20, 19', 20'-Me), 2.04 (1H, dd, J 16.1, 9.8 4'-Hax), 2.06 (1H, ddd, J 12.1, 6.0, 2.2, 4-Hax), 4.00 (1H, m, 3'-H), 4.39 (1H, t, J 6.0, 3-H), 5.74 (1H, d, J 16.1, 7-H), 6.09 (1H, AB, J 16.8, 7'-H), 6.14 (1H, AB, J 16.8, 8'-H), 6.15 (1H, d, J 11.3, 10'-H), 6.20 (1H, d, J 11.4, 10-H), 6.25 (1H, m, 14, 14'-H), 6.36 (2H, d, 12, 12'-H), 6.37 (1H, d, J 16.1, 8-H), 6.62 (1H, dd, J 11.4, 14.7, 11-H), 6.63 (2H, m, 15, 15'-H), 6.64(1H, dd, J 11.3, 14.1, 11'-H) (Ref. 0505/0510) ¹³C-NMR d(100.6 MHz, CDCl3): 12.75 (C20'), 12.80 (C19), 12.81 (C19'), 12.84 (C20), 21.62 (C18'), 25.72 (C16), 25.72 (C16'), 30.25 (C17'), 31.58 (C18), 32.16 (C17), 37.12 (C1'), 42.56 (C4'), 43.98 (C 1), 47.71 (C4), 48.43 (C2'), 48.50 (C2), 65.09 (C3'), 70.37 (C3), 82.48 (C5), 91.64 (C6), 122.83 (C7), 124.81 (C11), 124.91 (C11'), 125.56 (C7'), 126.15 (C5'), 130.05 (C15), 130.10 (C15'), 131.31 (C10'), 131.60 (C10), 132.58 (C14), 132.66 (C14'), 134.77 (C8), 134.86 (C9), 135.40 (C13), 136.40 (C9'), 136.49 (C13'), 137.57 (C12), 137.76 (C12'), 137.78 (C6'), 138.50 (C8') (Ref. 0505/0510)	m/z: 584 (33, M), 566 (3, M-H2O), 504 (6), 492 (2), 299 (7), 286 (16), 221 (29), 181 (239, 160 (39), 155 (30), 119 (53), 105 (43), 55 (35), 105 (43), 55 (35), 43(100) (Ref. 0505/0510)	CD in EPA: De 230 (+3.08), 278 (-6.15), 390 (-11.32), 426 (+2.38), 476 (-1.51) (Ref. 0505) CD in EPA: De 223 (0), 239 (+2.3), 254 (0), 275 (-7.6), 305 (-1.5), 335 (-2.1) (Ref. 0510)		Cucurbita maxima (Pumpkin) (Ref. 0510) Capsicum annuum (Red paprika) (Ref. 0504/0508/0505/0506/0511)		Antheraxanthin - cucurbitaxanthin A in Capsicum annuum (Ref. 0511) Changes in carotenoid composition and content during ripening of selective cultivars for paprika (Capsicum annuum) production (Ref. 1271).		Note: Left and right end groups on the chemical structure have been reversed.	[0217] / [0504] / [0505] / [0506] / [0508] / [0510] / [0511] / [1095] / [1271]
63		Cucurbitaxanthin B	(3S,5R,6S,3'S,5'R,6'R)-5,6:3',6'-Diepoxy-5,6,5',6'-tetrahydro-b,b-carotene-3,5'-diol	VCA0063	Masayoshi Ito		C₄₀H₅₆O₄	600.870									lmax (nm): benzene 483, 453, 427 (Ref. 0505); ether 415, 438, 468(Ref. 0510)	nmax(KBr)/cm^-¹: 3360m (OH), 2900s, 2850m, 1440w, 1379w, 1352w, 1292w, 1238w, 1085m, 1034m, 956s, 870w, 820w (Ref. 0510)	¹H-NMR d(400 MHz, CDCl3): 0.88 (3H, s, 17-Me), 0.98 (3H, s, 16'-Me), 1.15 (3H, s, 17'-Me), 1.19 (3H, s, 18'-Me), 1.21 (3H, s, 18-Me), 1.24 (1H, m, 2-Hax), 1.43 (3H, s 16-Me), 1.61 (1H, d, J 11.6, 2-Heq), 1.67 (1H, d, J 12.1, 4-Heq), 1.73 (3H, s, 18'-Me), 1.77 (1H, ddd, J 12.0, 3.6, 2.1, 2'-Heq), 1.84 (1H, ddd, J 11.5, 6, 2.2, 2-Hax), 1.93 (3H, s, 19'-Me), 1.95 (3H, s, 19-Me), 1.96 (6H, s 20, 20'-Me), 2.06 (1H, ddd, J 12.1, 6.0, 2.2, 4-Hax), 2.39 (1H, ddd, J 14.3, 5.2, 1.8, 4-Heq), 3.91 (1H, m, 3'-H), 4.39 (1H, t, J 6.0, 3-H), 5.74 (1H, d, J 16.1, 7-H), 5.88 (1H, d, J 15.5, 7'-H), 6.20 (1H, d, J 11.4, 10'-H), 6.21 (1H, d, J 11.4, 10-H), 6.26 (2H, m, 14, 14'-H), 6.29 (1H, d, J 15.5, 8'-H), 6.36 (1H, d, J 14.7, 12-H), 6.37 (1H, d, J 16.1, 8-H),6.37 (1H, d, J 14.7, 12'-H), 6.60 (1H, dd, J 11.5, 14.7, 11'-H), 6.61 (1H, dd J 11.5, 14.7, 11-H), 6.63 (2H, m, 15, 15'-H) (Ref. 0505/0510) ¹³C-NMR d(100.6 MHz, CDCl3): 12.9 (C19, 19', 20, 20'), 20.1 (C18'), 25.1 (C16'), 25.9 (C16), 29.7 (C17'), 31.8 (C18), 32.3 (C17), 41.3 (C4'), 47.9 (C2'), 48.2 (C4), 48.9 (C2), 65.0 (C3'), 123.0 (C7), 123.9 (C7'),124.7 (C11'), 124.8 (C11), 130.1 (C15, 15'), 132.2 (C10, 10'), 132.8 (C14, 14'), 135.0 (C8), 137.6 (C8'), 138.3 (C12,12') (Ref. 0505)	m/z: 600 (50, M), 582 (9, M-H2O), 564 (3, M-2H2O), 520 (21), 508 (21), 287 (36), 286 (32), 221 (100), 181 (57), 160 (45), 155 (26), 119 (32), 105 (26), 55 (10), 43 (25) (Ref. 0505/0510)	CD in EPA: De 228 (+2.13), 267 (-5.77), 327 (+0.94) (Ref. 0505)CD in EPA: De 210 (-6.8), 225 (0), 230 (+3.0), 236 (0), 267 (-19.0), 309 (0), 327 (+2.0), 340 (0) (Ref. 0510)		Cucurbita maxima (Pumpkin) (Ref. 0510) Capsicum annuum (Red paprika) (Ref. 0508/0505/0506)		Antheraxanthin -> cucurbitaxanthin A -> cucurbitaxanthin B in Capsicum annuum (Ref. 0511) Cucurbitaxanthin B is the substrate of violaxanthin de-epoxidase (Ref. 1143).		Note: Left and right end groups on the chemical structure have been reversed.	[0505] / [0506] / [0508] / [0510] / [0511] / [1143]
64		4-Oxomytiloxanthin	3,3',8'-Trihydroxy-7,8-didehydro-b,k-carotene-4,6'-dione	VCA0064	Masayoshi Ito		C₄₀H₅₂O₅	612.838									lmax (nm): hexane/isopropyl ethanoate/acetone (76:17:7, v/v) 447, 473, 502 (Ref. 0420)		¹H-NMR d(400 MHz, CDCl3): 0.852 (3H, s 16'-Me), 1.191 (3H, s 17'-Me), 1.311 (3H, s, 16-Me), 1.351 (3H, s 18'-Me), 1.355 (3H, s, 17-Me), 1.55 (1H, dd, J 14.3, 3, 4'-Hb), 1.72 (1H, dd, J 13.5, 4.5, 2'-Hb), 1.80 (1H, t, J 13, 2-Hax), 1.990 (3H, s, 19'-Me), 1.984 (3H, s, 20-Me), 2.004 (3H, s, 20'-Me), 2.052 (3H, s, 19-Me), 2.027 (3H, s, 18-Me), 2.09 (1H, dd, J 13.5, 7.5, 2'-Ha), 2.22 (1H, dd, J 12.8, 5.5, 2-Heq), 2.88 (1H, dd, J 14.3, 8.5, 4'-Ha), 4.33 (1H, ddd, J 14, 6, 1.8, 3-H), 4.53 (1H, m, 3'-H), 5.862 (1H, s, 7'-H), 6.34-7.24 olefinic H (Ref. 0420)	m/z: 612(1, M), 594 (1, M-H2O), 576 (1, M-2H2O), 413 (2), 383 (2), 83 (64), 41 (100) (Ref. 0420)		HPLC (columun: Sherisorb S 5-CN, detection : 450nm, mobile phase: hexana/isopropyl ethanoate/2-propanol/N-ethyldiisopropylamine 82.4:17:0.5:0.1 (v/v), flow rate : 1 mL/min. 7,8,7',8'-tetradehydroastaxanthin tR=798 sec, 7,8-didehydroastaxanthin tR=914 sec, astaxanthin tR=1042 sec, 4-oxomytiloxanthin tR=1712 sec) (Ref. 0420)	Asterias rubens (Starfish) (Ref. 0420)		Mytiloxanthin - 4-oxomytiloxanthin in Asterias rubens (Starfish) (Ref. 0420)			[0420]
65		4-Hydroxymytiloxanthin	(3S,4S,3'S,5'R)-3,4,3',8'-Tetrahydroxy-7,8-didehydro-b,k-caroten-6'-one	VCA0065	Masayoshi Ito		C₄₀H₅₄O₅	614.854									lmax (nm): ether 470 (Ref. 0423)		¹H-NMR d(300 MHz, CDCl3): 0.852 (3H, s 16'-Me), 1.191 (9H, s 16, 17, 17'-Me), 1.351 (3H, s 18'-Me), 1.55 (1H, dd, J 14.3, 3, 4'-Hb), 1.72 (1H, dd, J 13.5, 4.5, 2'-Hb), 1.995 (3H, s, 19'-Me), 1.978 (3H, s, 20-Me), 2.001 (3H, s, 20'-Me), 2.006 (3H, s, 18-Me), 2.016 (3H, s, 19-Me), 2.09 (1H, dd, J 13.5, 7.5, 2'-Ha), 2.88 (1H, dd, J 14.3, 8.5, 4'-Ha), 3.78 (1H, m, 3-H), 4.53 (1H, m, 3'-H), 5.862 (1H, s, 7'-H), 6.34-7.24 olefinic H, 16.288 (1H, s, enol-H) (Ref. 0423)	m/z: 614.3992 (M C40H54O5) (Ref. 0423)	CD in EPA: De 225 (-1.0), 298 (+1.8), 350 (-0.8) (Ref. 0423)		Asterina pectinifera, Asterias amurensis (Starfish) (Ref. 0423)		Mytiloxanthin - 4-hydroxymytiloxanthin - 4-oxomytiloxanthin in Asterina pectinifera, Asterias amurensis (Starfish) (Ref. 0423)			[0423]
66		Pectenolone	(3S,3'R)-3,3'-Dihydroxy-7',8'-didehydro-b,b-caroten-4-one	VCA0066	Masayoshi Ito		C₄₀H₅₂O₃	580.839		Inhibitotory effect on Epstein-Barr virus activation (anti-tumor promotion) (Ref. 0217)							lmax (nm): petroleum ether 459-462 (Ref. 0494/0496)	nmax(KBr)/cm^-¹: 3300m (OH), 2165w (acetylene), 1660s (conj. carbonyl), 960s (Ref. 0494/0496)	¹H-NMR d(80 MHz, CDCl3): 1.14 (3H, s, 16'-Me), 1.20 (6H, s, 16, 17'-Me), 1.32 (3H, s 17-Me), 1.94 (12H, s, 18, 20, 18', 20'-Me), 1.99 (6H, s, 19, 19'-Me), 4.00 (1H, m, 3'-H), 4.35 (1H, dd, 3-H), 6.1-6.8 olefinic H (Ref. 0494/0495/0496) ¹³C-NMR d(50 MHz, CDCl3): 36.6 (C-1), 45.4 (C-2), 69.2 (C-3), 200.4 (C-4), 126.8 (C-5), 162.3 (C-6), 123.2 (C-7), 142.4 (C-8), 134.4 (C-9), 135.1 (C-10), 124.4 (C-11), 139.8 (C-12), 136.7 (C-13), 133.9 (C-14), 130.8 (C-15), 26.2 (C-16), 30.8 (C-17), 14.0 (C-18), 12.6 (C-19)< 12.8 (C-20), 36.8 (C-1'), 46,7 (C-2'), 64.9 (C-3'), 41.5 (C-4'), 137.4 (C-5'), 124.2 (C-6'), 89.2 (C-7'), 98.6 (C-8'), 119.2 (C-9'), 138.0 (C-10'), 124.4 (C-11'), 135.3 (C-12'), 136.4 (C-13'), 133.3 (C-14'), 130.2 (C-15'), 28.8 (C-16'), 30.5 (C-17'), 22.5 (C-18'), 18.1 (C-19'), 12.8 (C-20') (Ref. 0516)	m/z: 580 (M) , 562 (M-18), 544 (M-18-18), 488, 474 (Ref. 0494/0496)	CD in EPA: De 222 (0), 234 (-5.9), 244 (0), 263 (+7.0), 271 (0), 302 (-11.8), 327 (0), 350 (+1.3), 387 (0) (Ref. 0516)		Patinopecten yessoensis (Scallop) (Ref. 0494) Pecten maximus (Scallop) (Ref. 0496) Scapharca broughtonii (Shell fish) (Ref. 0495) Asterina pectinifera, Asterias amurensis (Starfish) (Ref. 0423)		Diatoxanthin - Pectenol A and B - Pectenolonein Mytilus coruscus (Sea Mussel) (Ref. 0518)			[0217] / [0423] / [0494] / [0495] / [0496] / [0516] / [0518]
67		Pectenol A/ (Pectenol)	(3S,4R,3'R)-7',8'-Didehydro-b,b-carotene-3,4,3'-triol	VCA0067	Masayoshi Ito		C₄₀H₅₄O₃	582.855		Inhibitotory effect on Epstein-Barr virus activation (anti-tumor promotion) (Ref. 0217)							lmax (nm): petroleum ether 425 (sh), 451, 479 (Ref. 0427/0517/0518)	nmax(KBr)/cm^-¹: 3300m (OH), 2165w (acetylene), 960s (Ref. 0427)	¹H-NMR d(80 MHz, CDCl3): 1.06 (3H, s, 16-Me), 1.08 (3H, s, 17-Me), 1.14 (3H, s, 16'-Me), 1.20 (3H, s, 17'-Me), 1.89 (3H, s 18-Me), 1.92 (3H, s, 18'-Me), 1.96 (9H, s, 19, 20, 20'-Me), 4.00 (3H, m, 3, 4, 3'-H), 6.1-6.8 olefinic H (Ref. 0427) ¹H-NMR d(300 MHz, CDCl3): 1.068 (3H, s, 16-Me), 1.091 (3H, s, 17-Me), 1.147 (3H, s, 16'-Me), 1.201 (3H, s, 17'-Me), 1.896 (3H, s 18-Me), 1.924 (3H, s, 18'-Me), 1.956 (3H, s, 20-Me), 1.967 (3H, s, 19-Me), 1.977 (3H, s, 20'-Me), 2.006 (3H, s, 19'-Me), 3.87 (1H, m 3-H), 3.96 (1H, d, J 3.5, 4-H), 3.99 (1H, m, 3'-H), 6.1-6.8 olefinic H (Ref. 0517/0518)	m/z: 582 (M) , 564 (M-18), 562 (M-18-18), 546, 528, 490, 476 (Ref. 0427/0517)	CD in EPA: De 224 (-5.6), 235 (0), 246 (+5.6), 262 (0), 285 (-10.9), 310 (0), 340 (+3.7) (Ref. 0517)		Mytilus coruscus (Sea Mussel) (Ref. 0427/0517/0518) Patinopecten yessoensis (Scallop) (Ref. 0494) Scapharca broughtonii (Shell fish) (Ref. 0495) Marine Shell Fishes (Ref. 0430) Mytilus edulis (Edible Mussel) (Ref. 0426) Asterina pectinifera, Asterias amurensis (Starfish) (Ref. 0423)	Partial synthesis of pectenol A by NaBH4 reduction of pectenolone was discribed. (Ref. 0517/0518)	Diatoxanthin - Pectenol A and B - Pectenolonein Mytilus coruscus (Sea Mussel) (Ref. 0518)			[0217] / [0423] / [0426] / [0427] / [0430] / [0494] / [0495] / [0517] / [0518]
68		Pectenol B	(3S,4S,3'R)-7',8'-Didehydro-b,b-carotene-3,4,3'-triol	VCA0068	Masayoshi Ito		C₄₀H₅₄O₃	582.855		Inhibitotory effect on Epstein-Barr virus activation (anti-tumor promotion) (Ref. 0217)							lmax (nm): ether 425 (sh), 451, 479 (Ref. 0518)	nmax(KBr)/cm^-¹: 3300m (OH), 2165w (acetylene), 960s (Ref. 0518)	¹H-NMR d(300 MHz, CDCl3): 1.078 (3H, s, 16-Me), 1.094 (3H, s, 17-Me), 1.147 (3H, s, 16'-Me), 1.201 (3H, s, 17'-Me), 1.813 (3H, s 18-Me), 1.925 (3H, s, 18'-Me), 1.957 (3H, s, 20-Me), 1.966 (3H, s, 19-Me), 1.977 (3H, s, 20'-Me), 2.006 (3H, s, 19'-Me), 3.79 (1H, m 3-H), 3.94 (1H, d, J 7.5, 4-H), 3.99 (1H, m, 3'-H), 6.1-6.8 olefinic H (Ref. 0518)	m/z: 582.4055 (M, C4054O3) , 564 (M-18), 562 (M-18-18), 546, 528, 490, 476 (Ref. 0518)	CD in EPA: De 224 (-9.0), 235 (0), 246 (+6.0), 262 (0), 285 (-21.5), 310 (0), 340 (+2.0) (Ref. 0518)		Mytilus coruscus (Sea Mussel) (Ref. 0427/0517/0518) Asterina pectinifera, Asterias amurensis (Starfish) (Ref. 0423)	Partial synthesis of pectenol B by NaBH4 reduction of pectenolone was discribed. (Ref. 0517/0518)	Diatoxanthin - Pectenol A and B - Pectenolonein Mytilus coruscus (Sea Mussel) (Ref. 0518)			[0217] / [0423] / [0427] / [0517] / [0518]
69		(4R)-4-Hydroxyalloxanthin/ (3S,4R,3'R)-4-Hydroxyalloxanthin	(3S,4R,3'R)-7,8,7',8'-Tetradehydro-b,b-carotene-3,4,3'-triiol	VCA0069	Masayoshi Ito		C₄₀H₅₂O₃	580.839									lmax (nm): ether 426 (sh), 452, 480 (Ref. 0518)	nmax(KBr)/cm^-¹: 3300m (OH), 2165w (acetylene), 960s (Ref. 0518)	¹H-NMR d(300 MHz, CDCl3): 1.146 (3H, s, 16'-Me), 1.153 (3H, s, 16-Me), 1.201 (3H, s, 16'-Me), 1.208 (3H, s, 17'-Me), 1.924 (3H, s, 18'-Me), 1.962 (3H, s, 19-Me), 1.977 (3H, s, 20'-Me), 2.004 (6H, s, 18, 20'-Me), 2.006 (3H, s, 19'-Me), 2.060 (3H, s, 18-Me), 3.87 (1H, m 3-H), 3.98 (1H, d, J 3.5, 4-H), 3.99 (1H, m, 3'-H), 6.1-6.8 olefinic H (Ref. 0518)	m/z: 580.3912 (M, C4052O3) , 562 (M-18), 560 (M-18-18), 544, 522, 488 (Ref. 0518)	CD in EPA: De 255 (0), 290 (-2), 350 (+0.5) (Ref. 0518)		Mytilus coruscus (Sea Mussel) (Ref. 0427/0517/0518) Asterina pectinifera, Asterias amurensis (Starfish) (Ref. 0423)	Partial synthesis of (3S,4R,3'R)-4-hydroxyalloxanthin by NaBH4 reduction of (3S,3'R)-4-ketoalloxanthin was discribed. (Ref. 0518)	Alloxanthin - 4-hydroxyalloxanthin -4-ketoalloxanthin in Mytilus coruscus (Sea Mussel) (Ref. 0518)			[0423] / [0427] / [0517] / [0518]
70		(4S)-4-Hydroxyalloxanthin/ (3S,4S,3'R)-4-Hydroxyalloxanthin	(3S,4S,3'R)-7,8,7',8'-Tetradehydro-b,b-carotene-3,4,3'-triol	VCA0070	Masayoshi Ito		C₄₀H₅₂O₃	580.839									lmax (nm): ether 426 (sh), 452, 480 (Ref. 0518)	nmax(KBr)/cm^-¹: 3300m (OH), 2165w (acetylene), 960s (Ref. 0518)	¹H-NMR d(300 MHz, CDCl3): 1.191 (6H, s, 16, 17-Me), 1.146 (3H, s, 16'-Me), 1.201 (3H, s, 17'-Me), 1.924 (3H, s, 18'-Me), 1.961 (3H, s, 19-Me), 1.977 (3H, s, 20'-Me), 2.004 (6H, s, 18, 20'-Me), 2.006 (3H, s, 19'-Me), 3.77 (1H, m 3-H), 3.98 (1H, d, J 7.5, 4-H), 3.99 (1H, m, 3'-H), 6.1-6.8 olefinic H (Ref. 0518)	m/z: 580.3912 (M, C4052O3) , 562 (M-18), 560 (M-18-18), 544, 522, 488 (Ref. 0518)	CD in EPA: De 255 (0), 290 (-2), 350 (+0.5) (Ref. 0518)		Mytilus coruscus (Sea Mussel) (Ref. 0427/0517/0518) Asterina pectinifera, Asterias amurensis (Starfish) (Ref. 0423)	Partial synthesis of (3S,4S,3'R)-4-hydroxyalloxanthin by NaBH4 reduction of (3S,3'R)-4-ketoalloxanthin was discribed. (Ref. 0518)	Alloxanthin - 4-hydroxyalloxanthin -4-ketoalloxanthin in Mytilus coruscus (Sea Mussel) (Ref. 0518)			[0423] / [0427] / [0517] / [0518]
71		4-Ketocynthiaxanthin/ 4-Ketoalloxanthin	(3S,3'R)-3,3'-Dihydroxy-7,8,7',8'-tetradehydro-b,b-caroten-4-one	VCA0071	Masayoshi Ito		C₄₀H₅₀O₃	578.823									lmax (nm): ether 469 (Ref. 0518)	nmax(KBr)/cm^-¹: 3300m (OH), 2165w (acetylene), 1660 (conj. carbonyl), 960s (Ref. 0518)	¹H-NMR d(300 MHz, CDCl3): 1.146 (3H, s, 16'-Me), 1.201 (3H, s, 17'-Me), 1.309 (3H, s, 16-Me), 1.354 (3H, s, 17-Me), 1.925 (3H, s, 18'-Me), 1.970 (3H, s, 20-Me), 1.977 (3H, s, 20'-Me), 2.006 (3H, s, 19'-Me), 2.025 (3H, s, Me-18), 2.043 (3H, s, Me-19), 3.99 (1H, m, 3'-H), 4.33 (1H, dd, J 14, 6, 3-H), 6.1-6.8 olefinic H (Ref. 0518)	m/z: 578.3762 (M, C4050O3) , 560 (M-18), 542, 522, 486 (Ref. 0518)	CD in EPA: De 230 (+4.0), 240 (0), 302 (-5.2), 312 (0) (Ref. 0518)		Mytilus coruscus (Sea Mussel) (Ref. 0518) Asterina pectinifera, Asterias amurensis (Starfish) (Ref. 0423)		Alloxanthin - 4-hydroxyalloxanthin -4-ketoalloxanthin in Mytilus coruscus (Sea Mussel) (Ref. 0518)			[0423] / [0518]
72		(4S,4'S)-4,4'-Dihydroxydiatoxanthin/ 4,4'-Dihydroxydiatoxanthin	(3S,4S,3'S,4'S)-7,8-Didehydro-b,b-carotene-3,4,3',4'-tetrol	VCA0072	Masayoshi Ito		C₄₀H₅₄O₄	598.854									lmax (nm): ether 425 (sh), 451, 479 (Ref. 0423)		¹H-NMR d(300 MHz, CDCl3): 1.078 (3H, s, 16-Me), 1.094 (3H, s, 17-Me), 1.191 (6H, s, 16', 17'-Me), 1.813 (3H, s 18-Me), 1.957 (3H, s, 20-Me), 1.961 (3H, s, 20-Me), 1.966 (3H, s, 19-Me), 2.004 (6H, s, 18', 19'-Me), 3.79 (2H, m, 3, 3'-H), 3.94 (1H, d, J 7.5, 4-H), 3.98 (1H, d, J 7.5, 3'-H), 6.1-6.8 olefinic H (Ref. 0423)	m/z: 598.4017 (M, C4054O4) (Ref. 0423)	CD in EPA: De 224 (-5.0), 235 (0), 246 (+6.0), 262 (0), 285 (-12.5), 310 (0), 340 (+3.0) (Ref. 0423)		Asterina pectinifera, Asterias amurensis (Starfish) (Ref. 0423)		Diatoxanthin - 4,4'-dihydroxydiatoxanthin - 4-keto-4'-hydroxydiatoxanthin - 7,8-didehydroastaxanthin in Asterina pectinifera, Asterias amurensis (Starfish) (Ref. 0423)			[0423]
73		(4S,4'S)-4,4'-Dihydroxyalloxanthin/ 4,4'-Dihydroxyalloxanthin	(3S,4S,3'S,4'S)-7,8,7',8'-Tetradehydro-b,b-carotene-3,4,3',4'-tetrol	VCA0073	Masayoshi Ito		C₄₀H₅₂O₄	596.838									lmax (nm): ether 426 (sh), 452, 480 (Ref. 0423)		¹H-NMR d(300 MHz, CDCl3): 1.191 (12H, s, 16, 17, 16', 17'-Me), 1.961 (6H, s 20, 20'-Me), 2.004 (12H, s, 18, 19, 18', 19'-Me), 3.78 (2H, m, 3, 3'-H), 3.98 (2H, d, J 7.5, 4-H), 6.1-6.8 olefinic H (Ref. 0423)	m/z: 596.3871 (M, C4052O4) (Ref. 0423)	CD in EPA: De 255 (0), 290 (-5), 350 (+0.5) (Ref. 0423)		Asterina pectinifera, Asterias amurensis (Starfish) (Ref. 0423)		Alloxanthin - 4,4'-dihydroxyalloxanthin - 4-keto-4'-hydroxyalloxanthin - 7,8,7',8'-tetradehydroastaxanthin in Asterina pectinifera, Asterias amurensis (Starfish) (Ref. 0423)			[0423]
74		4-Keto-4'-hydroxydiatoxanthin	(3S,3'S,4'S)-3,3',4'-Trihydroxy-7,8-didehydro-b,b-caroten-4-one	VCA0074	Masayoshi Ito		C₄₀H₅₂O₄	596.838									lmax (nm): ether 454-473 (Ref. 0423)		¹H-NMR d(300 MHz, CDCl3): 1.191 (6H, s, 16', 17'-Me), 1.211 (3H, s. 16-Me), 1.321 (3H, s, 17-Me), 1.944 (3H, s, 18-Me), 1.968 (3H, s, 20-Me), 1.988 (3H, s, 20'-Me), 2.000 (9H, s, 19, 18', 19'-Me), 3.78 (2H, m,3'-H), 3.98 (1H, d, J 7.5, 3'-H), 4.33 (1H, dd, J 18, 6, 3-H), 6.1-6.8 olefinic H (Ref. 0423) (3S,3'S,4'R) form (Ref. 1299)	m/z: 596.3866 (M, C4052O4) (Ref. 0423)	CD in EPA: De 222 (0), 234 (-5.9), 244 (0), 263 (+7.0), 271 (0), 302 (-13.8), 327 (0) (Ref. 0423) (3S,3'S,4'R) form (Ref. 1299)		Asterina pectinifera, Asterias amurensis (Starfish) (Ref. 0423) (3S,3'S,4'R) form from Carassius auratus (goldfish) (Ref. 1299)		Diatoxanthin - 4,4'-dihydroxydiatoxanthin - 4-keto-4'-hydroxydiatoxanthin - 7,8-didehydroastaxanthin in Asterina pectinifera, Asterias amurensis (Starfish) (Ref. 0423)			[0423] / [1299]
75		4-Keto-4'-hydroxyalloxanthin	(3S,3'S,4'S)-3,3',4'-Trihydroxy-7,8,7',8'-tetradehydro-b,b-caroten-4-one	VCA0075	Masayoshi Ito		C₄₀H₅₀O₄	594.823									lmax (nm): ether 446, 496 (sh) (Ref. 0423)		¹H-NMR d(300 MHz, CDCl3): 1.191 (6H, s, 16', 17'-Me), 1.310 (3H, s. 16-Me), 1.354 (3H, s, 17-Me), 1.972 (3H, s, 20-Me), 1.999 (3H, s, 20'-Me), 2.052 (6H, s, 18, 18', 19'-Me), 2.064 (3H, s, 19-Me), 3.78 (2H, m,3'-H), 3.98 (1H, d, J 7.5, 3'-H), 4.33 (1H, dd, J 18, 6, 3-H), 6.1-6.8 olefinic H (Ref. 0423) (3S,3'S,4'R) form (Ref. 1299)	m/z: 594.3720 (M, C4050O4) (Ref. 0423)	CD in EPA: De 230 (+4.0), 240 (0), 302 (85.2), 312 (0) (Ref. 0423) (3S,3'S,4'R) form (Ref. 1299)		Asterina pectinifera, Asterias amurensis (Starfish) (Ref. 0423) (3S,3'S,4'R) form from Carassius auratus (goldfish) (Ref. 1299)		Alloxanthin - 4,4'-dihydroxyalloxanthin - 4-keto-4'-hydroxyalloxanthin - 7,8,7',8'-tetradehydroastaxanthin in Asterina pectinifera, Asterias amurensis (Starfish) (Ref. 0423)			[0423] / [1299]
76		Amarouciaxanthin A	(3S,5R,6R,6'S)-3,5,6'-Trihydroxy-6,7-didehydro-5,6,7',8'-tetrahydro-b,e-carotene-3',8'-dione	VCA0076	Masayoshi Ito		C₄₀H₅₄O₅	614.854									lmax (nm): ether 455-460 (Ref. 0519)	nmax(KBr)/cm^-¹: 3350 (OH), 1928 (allene), 1660 (conj. carbonyl), 1650 (conj. carbonyl), 960 (trans olefin) (Ref. 0519)	¹H-NMR d(270 MHz, CDCl3): 1.05 (3H, s, 16-Me), 1.08 (6H, s. 17, 16'-Me), 1.34 (6H, s, 17', 18'-Me), 1.81 (3H, s, 19'-Me),1.89 (3H, s, 18-Me), 1.95 (3H, s, 19-Me), 1.98 (6H, s, 20, 20'-Me), 2.35 (1H, AB, J 18, H-2ax), 2.48 (1H, AB, J 18, H-2eq), 2.96 (1H, AB, J 15, H-7), 3.06 (1H, AB, J 15, H-7),4.20 (1H, m, 3'-H), 5.81 (1H, s, 4-H), 6-7 olefinic H (Ref. 0519)	m/z: 614 (1, M), 596 (2, M-H2O), 578 (4, M-2H2O), 462 (100), 445 (23), 444 (50) (Ref. 0519)	CD in EPA: De 220 (0), 245 (-44.9), 260 (0), 270 (+16.7) (Ref. 0519)		Amaroucium pliciferum (Tunicate) (Ref. 0401/0519) Paphia euglypta (Shellfish) (Ref. 0521)		Fucoxanthin - fucoxanthinol - amarouciaxanthin A - amarouciaxanthin B in Amaroucium pliciferum (Tunicate) (Ref. 0401/0519)		Note: Semisystematic name, and left and right end groups on the chemical structure have been changed.	[0401] / [0519] / [0521]
77		Amarouciaxanthin B/ Sidnyaxanthin	(3R,6'S)-3,6'-Dihydroxy-7,8-didehydro-7',8'-dihydro-b,e-carotene-3',8'-dione	VCA0077	Masayoshi Ito		C₄₀H₅₂O₄	596.838		Inhibitotory effect on Epstein-Barr virus activation (anti-tumor promotion) (Ref. 0217)							lmax (nm): ether 463 (Ref. 0519)	nmax(KBr)/cm^-¹: 3350 (OH), 2165 (acetylene), 1660 (conj. carbonyl), 1650 (conj. carbonyl), 960 (trans olefin) (Ref. 0519)	¹H-NMR d(270 MHz, CDCl3): 1.05 (3H, s, 16-Me), 1.08 (3H, s. 17-Me), 1.14 (3H, s, 16'-Me), 1.20 (3H, s, 17'-Me), 1.89 (3H, s, 18-Me), 1.90 (3H, s, 18'-Me),1.95 (3H, s, 19-Me), 1.98 (9H, s, 20, 19', 20'-Me), 2.35 (1H, AB, J 18, H-2ax), 2.48 (1H, AB, J 18, H-2eq), 2.96 (1H, AB, J 15, H-7), 3.06 (1H, AB, J 15, H-7),4.00 (1H, m, 3'-H), 5.81 (1H, s, 4-H), 6-7 olefinic H (Ref. 0519) ¹³C-NMR d(50 MHz, CDCl3): 11.6 (C19), 12.7 (C-20'), 12.9 (C-20), 18.1 (C-19'), 20.7 (C-18), 23.3 (C-16), 24.8 (C-17), 38.7 (C-7), 42.0 (C-1), 49.8 (C-2), 78.5 (C-6), 89.5 (C-7'), 98.6 (C-8'), 120.0 (C-9'), 123.1 (C-11), 125.3 (C-11'), 126.0 (C-4), 129.6 (C-15'), 132.9 (C-14'), 133.2 (C-15), 135.0 (C-9, 12'), 135.4 (C-13), 137.6 (C-13'), 137.7 (C-14), 138.0 (C-10'), 142.2 (C-10), 147.1 (C-12), 167.9 (C-5), 197.6 (C-8), 203.4 (C-3) (Ref. 0519)	m/z: 596 (1, M), 444 (100) (Ref. 0519)	CD in EPA: De 220 (0), 245 (-35.0), 260 (0), 270 (+16.7) (Ref. 0519)		Amaroucium pliciferum (Tunicate) (Ref. 0401/0519)		Fucoxanthin - fucoxanthinol - amarouciaxanthin A - amarouciaxanthin B in Amaroucium pliciferum (Tunicate) (Ref. 0401/0519)		Note: Semisystematic name, and left and right end groups on the chemical structure have been changed.	[0217] / [0401] / [0519]
78		Mytiloxanthinone	3,8'-Dihydroxy-7,8-didehydro-b,k-carotene-3',6'-dione	VCA0078	Masayoshi Ito		C₄₀H₅₂O₄	596.838		Inhibitotory effect on Epstein-Barr virus activation (anti-tumor promotion) (Ref. 0217)							lmax (nm): ether 475 (Ref. 0035/0520)	nmax(KBr)/cm^-¹: 3390 (OH), 2165 (acetylene), 1738 (carbonyl), 1610, 1595, 1588 (enolic b-diketone), 960 (trans olefin) (Ref. 0035/0520)	¹H-NMR d(80 MHz, CDCl3): 1.03 (3H, s, 16'-Me), 1.14 (3H, s. 16-Me), 1.20 (3H, s, 17-Me), 1.22 (3H, s, 17'-Me), 1.34 (3H, s, 18'-Me), 1.92 (3H, s, 18-Me),1.99 (12H, s, 19, 20, 19', 20'-Me), 1.98 (9H, s, 20, 19', 20'-Me), 5.90 (1H, s, 7'-H), 6-7 olefinic H, 16.25 (enol H) (Ref. 0035/0520)	m/z: 596.3862 (M, C40H52O4), 578 (M-H2O), 560 (M-2H2O), 471 (M-125), 401 (M-125), 195 (M-401), 125 (Ref. 0035/0520)			Malocynthia roretzi (Sea suirt) (Ref. 0035/0401)		Fucoxanthin - fucoxanthinol - halocynthiaxanthin - mytiloxanthin -mytiloxanthinone (Ref. 0035/0401)			[0035] / [0217] / [0401] / [0520]
79		Phoenicopterone/ a-Echinenone	(6'R)-b,e-Caroten-4-one	VCA0079	Masayoshi Ito		C₄₀H₅₄O	550.856									lmax (nm): ether 449, 470 (Ref. 0502)		¹H-NMR d(300 MHz, CDCl3): 0.82 (3H, s, 16'-Me), 0.90 (3H, s, 17'-Me), 1.03 (6H, s, 16,17-H), 1.58 (3H, s, 18'-Me), 1.85 (2H, t, J 7, 2-H), 1.87 (3H, s, 18-Me), 1.91 (3H, s, 19'-Me), 1.97 (3H, s, 20'-Me), 1.98 (3H, s 20-Me), 2.00 (3H, s, 19-Me), 2.02 (2H, t, J 7, H-4'), 2.51 (2H, t, J 7, 4-H), 5.41 (1H, br. s, 4'-H), 5.54 (1H, dd, J 15.5, 7, H-7'), 6.1-6.7 (olefinic H) (Ref. 0502)	m/z: 550 (M) (Ref. 0502)	CD in EPA: De 225 (+1), 260 (+10), 285 (0), 345 (+2.5) (Ref. 0502)		Sea-urchins (Ref. 0502)		a-Carotene - a-echinenone in Sea-urchins (Ref. 0502)			[0502]
80		4-Ketocapsanthin	(3S,3'S,5'R)-3,3'-Dihydroxy-b,k-carotene-4,6'-dione	VCA0080	Masayoshi Ito		C₄₀H₅₄O₄	598.854									lmax (nm): ether 473 (Ref. 0522)		¹H-NMR d(300 MHz, CDCl3): 0.84 (3H, s, 16'-Me), 1.21 (3H, s, 16, 17'-Me), 1.32 (3H, s, 17-Me), 1.37(3H, s, 18'-Me), 1.74 (3H, s, 18-Me), 1.81 (1H, dd, 2-Hb), 1.95 (1H, s 18-Me), 1.96 (3H, s, 19'-Me), 1.99 (3H, s, 20'-Me), 2.03 (6H, s, 19, 20-Me), 2.16 (1H, dd, 2-Ha), 2.39 (1H, ddd, J 17, 6, 1.5, 4a-H), 2.96 (1H, dd, J 15.5, 9, 4'a-H), 3.68 (1H, s, OH), 4.33 (1H, m, 3-H), 4.52 (1H, m, 3'-H), 6.13-6.8 (olefinic H), 7.33 (1H, d, J 15, 8'-H) (Ref. 0522)	m/z: 550 (M) (Ref. 0522)	CD in EPA: De 225 (0), 240 (-7.0), 252 (0), 260 (+2.5), 266 (0), 310 (-12.0), 335 (-2.5), 370 (-7.5) (Ref. 0522)		Carrassius auratus (Goldfih, feed on paprika pigment) (Ref. 0522)		Capsanthin - 4-ketocapsanthin in Carrassius auratus (Goldfih, feed on paprika pigment) (Ref. 0522)			[0522]
81		Phytoene	15-cis-7,8,11,12,7',8',11'12'-Octahydro-y,y-carotene	VCA1001	Norihiko Misawa		C₄₀H₆₄	544.936		The transfer of crtB gene from Erwinia uredovora in mammalian cells produced phytoene, and the cells were protective against oxidative stress and H-ras induced transformation (Ref. 1205). The cancer preventive activity of phytoene was confirmed in phytoene producing mammalian cells (Ref. 1207). Transgenic mice carrying the phytoene synthase gene crtB produce phytoene and induce connexin 26 (Ref. 1349).							lmax (nm): acetonitrile/methanol/THF (58:35:7) 278 (shoulder), 288, 298 [Spectrum 1004] [Spectrum 1051] (Ref. 1057) methanol 276 (shoulder), 284, 294 (shoulder) (15-cis) [Spectrum 1113] (Ref. 1052)		1H- and 13C-NMR in CDCl3 (Ref. 1265). 13C-NMR in CDCl3 (Ref. 0061)			HPLC (column; Novapak C18 (Waters) 8 X 100 mm: eluelnt; acetonitrile/methanol/THF 58:35:7: flow 2.0 ml/min) Rt=28.2 min (all-trans), 26.9 min (15-cis) (Ref. 1057)	The crtI mutant of Rhodobacter sphaeroides (purple photosynthetic bacteria) (Ref. 1089) Myxococcus sp. MY-18 (fruiting gliding myxobacterium) accumulats (Ref. 1353).		Phytoene is the first colorless carotenoid, which is formed form two molecules of geranylgeranyl diphosphate (GGPP) by phytoene synthase in all carotenogenic organisms (Ref. 1001/1029/1030). This reaction is reported to be a rate-limiting step for carotenoid biosynthesis in a higher plant and a carotenogenic bacterium (Ref. 1016/1031). All carotenoids, except for C₃₀ special ones, are synthesized from phytoene as the starting carotenoid substrate (Ref. 1003/1004/1005). Chloroflexus aurantiacus (green filamentous photosynthetic bacterium) accumulates phytoene in the culture with 2-hydroxybiphenyl, and this compound inhibits carotenoid formation by inhibiting the flow of electrons liberated in the course of the desaturase reaction (Ref. 1166). The genes from Xanthophyllomyces dendrorhous (crtYB) (Ref. 1172), Mucor circinelloides (carRP) (Ref. 1173), and Phycomyces blakesleeanus (carRA) (Ref. 1174) (fungus) encode a bifunctional protein involved phytoene synthase activity located in C-terminus domain and lycopene cyclase activity located in N-terminus domain. An Escherichia coli transformant carrying the Erwinia uredovora crtE and crtB genes (Ref. 0201/1002). [Table 1019] Phytoene desaturase (PDS) inhibitor (Ref. 1252)	Phytoene synthase genes (crtB or psy), which mediate the formation of phytoene from GGPP, have been cloned from the photosynthetic bacteria Rhodobacter species (Ref. 1032/1033), the nonphotosynthetic bacteria Erwinia species (Erwinia uredovara and E. herbicola) (Ref. 0201/0233/1034) and Thermus thermophilus (Ref. 1031), the cyanobacterium Synechococcus PCC7942 (Ref. 1029), the fungus Neurospora crassa (Ref. 1035), and higher plants such as tomato and red pepper (Ref. 1036/1037/1038/1039). In tomato, PSY1 transcripts predominate in seedlings and in late stages of fruit ripeing, whereas PSY2 transcripts are relatively more abundant in mature leaves (Ref. 1036/1186/1190).	Biotechnological achievement has been made in metabolic engineering of caroteoids in animal cells, by the group of H. Nishino in 1995, i. e., a transgenic mammalian cells, which accumulates phytoene, has been constructed by expressing the Erwinia phytoene synthase gene crtB (Ref. 1028). The photophysics of two lowest lying singlet excited states in 15-cis-phytoene and 15-cis-phytofluene by means of steady-state fluorescence spectroscopy (Ref. 1113)	[0061] / [0201] / [0233] / [1001] / [1002] / [1003] / [1004] / [1005] / [1016] / [1028] / [1029] / [1030] / [1031] / [1032] / [1033] / [1034] / [1035] / [1036] / [1037] / [1038] / [1039] / [1052] / [1057] / [1089] / [1113] / [1166] / [1172] / [1173] / [1174] / [1186] / [1190] / [1205] / [1207] / [1252] / [1265] / [1349] / [1353]
82		Phytofluene	7,8,11,12,7',8'-Hexahydro-y,y-carotene	VCA1002	Norihiko Misawa		C₄₀H₆₂	542.920		The photophysics of two lowest lying singlet excited states in 15-cis-phytoene and 15-cis-phytofluene by means of steady-state fluorescence spectroscopy (Ref. 1113)							lmax (nm): acetonitrile/methanol/THF (58:35:7) 255, 334, 349, 368, %III/II=71 [Spectrum 1005] [Spectrum 1051] (Ref. 1057) methanol 254, 329, 346, 365, %III/II=85.0 [Spectrum 1114] (Ref. 1052)				Fluoresence (Ref. 1062)	HPLC (column; Novapak C18 (Waters) 8 X 100 mm: eluelnt; acetonitrile/methanol/THF 58:35:7: flow 2.0 ml/min) Rt=20.5 min (all-trans), 19.3 min (15-cis) (Ref. 1057)			Phytofluene is synthesized from phytoene by the one desaturation reaction. [Table 1020]			[1052] / [1057] / [1062] / [1113]
83		z-Carotene/ Symmetric z-Carotene/ 7,8,7',8'-Tetrahydrolycopene	7,8,7',8'-Tetrahydro-y,y-carotene	VCA1003	Norihiko Misawa		C₄₀H₆₀	540.904									lmax (nm): acetonitrile/methanol/THF (58:35:7) 237, 294, 381, 401, 426, %III/II=100 [Spectrum 1006] [Spectrum 1051] (Ref. 1057) methanol 295, 377, 398, 422, %III/II=95.0 [Spectrum 1115] (Ref. 1052) hexane 358, 378, 399.5, 424.5 (Ref. 1073)				Fluoresence (Ref. 1062)	HPLC (column; Novapak C18 (Waters) 8 X 100 mm: eluelnt; acetonitrile/methanol/THF 58:35:7: flow 2.0 ml/min) Rt=16.3 min (all-trans), 15.1 min (15-cis) (Ref. 1057) Silicagel G TLC, benzene-hexane (3:17): Rf=0.36 (Ref. 1073)	Rhodobacter capsulatus, Rhobacter sphaeroides, Rubrivax gelatinosus (purple photosynthetic bacteria); Chlorobium limicola, Pelodictyon luteolum (green sulfur photosynthetic bacteria); Rhoseobacter denitrificans (=Erythrobacter sp. OCh 114) (aerobic photosynthetic bacteria) (Ref. 1054/1073) Carrot root (Ref. 1055)		z-Carotene is synthesized from phytoene through two-step desaturation reactions with phytoene desaturase (plant-type; CrtP/PDS) via phytofluene in carotenogenic organisms such as cyanobacteria, algae, and higher plants (Ref. 1003/1004/1005/1046). In these organisms, z-carotene is metabolized to lycopene by further two-step desaturation reactions with z-carotene desaturase (CrtQ/ZDS) by way of neurosporene (Ref. 1003/1004/1005/1022/1131). A plastid terminal oxidase (PTOX) is a cofactor of PDS and ZDS in plants, such as Arabidopsis, tomato, peper and rice (Ref. 1187/1188/1189). Plastoquinone and ubiquinone are the cofactor of ZDS from peper (Ref. 1022). CrtP/ZDS is inhibited by norflurazon and a herbicide J852, and CrtQ/ZDS by the J852 (Ref. 1004/1191). CrtQ is inhibited by 4-phenyl-3-(substituted benzylthio)-4H-1,2,4-triazoles in lettuse leaves (Ref. 1302). An Escherichia coli transformant carrying the Erwinia uredovora crtE and crtB and Synechococcus PCC7942 pds (crtP) genes (Ref. 1046). [Table 1021] z-Carotene desaturase (ZDS) inhibitor (Ref. 1252)	Phytoene desaturase genes (pds, crtP), which mediate the formation of z-carotene from phytoene, have been cloned from the cyanobacterium Synechococcus PCC7942 (Ref. 1045), and higher plants such as tomato and soybean (Ref. 1038/1047/1048).		[1003] / [1004] / [1005] / [1022] / [1038] / [1045] / [1046] / [1047] / [1048] / [1052] / [1054] / [1055] / [1057] / [1062] / [1073] / [1131] / [1187] / [1188] / [1189] / [1191] / [1252] / [1302]
84		Neurosporene	7,8-Dihydro-y,y-carotene	VCA1004	Norihiko Misawa		C₄₀H₅₈	538.889									lmax (nm): acetonitrile/methanol/THF (58:35:7) 269, 333, 418, 442, 470, %III/II=91 [Spectrum 1007] [Spectrum 1051] (Ref. 1057); methanol 328, 413, 436, 465, %III/II=90.2 [Spectrum 1116] (Ref. 1052); hexane 415, 438, 468 (Ref. 1073)				Fluorescence spectra in n-hexane and CS₂ (Ref. 1060/1061) Fluoresence (Ref. 1062)	HPLC (column; Novapak C18 (Waters) 8 X 100 mm: eluelnt; acetonitrile/methanol/THF 58:35:7: flow 2.0 ml/min) Rt=13.4 min (Ref. 1057) Silicagel G TLC, benzene-hexane (3:17): Rf=0.31 (Ref. 1073)	Accumulation in Rhodobacter sphaeroides Ga and G1C mutants(Ref. 1054). Rhodobaca bogoriensis (purple photosynthetic bacteria) (Ref. 1100). Roseobacter denitrificans (=Erythrobacter sp. OCh 114) (aerobic photosynthetic bacterium) (Ref. 1073).		[Table 1022] Neurosporene is synthesized from phytoene through three-step desaturation reactions with phytoene desaturase (Rhodobacter-type) via phytofluene and z-carotene in the purple photosynthetic bacteria Rhodobacter species (Ref. 1005/1032). The first carotenoid in the spheroidene pathway of purple photosynthetic bacteria (Ref. 1054). Rhodobacter sphaeroides Ga and G1C mutants accumulate neurosporene (Ref. 1054). The crtC mutant of Rba. sphaeroides cultured under anaerobic conditions also accumulates neurosporene, and the crtD mutant accumulatates neurosporene, chloroxanthin and methoxyneurosporene (Ref. 1089). An Escherichia coli transformant carrying the Erwinia uredovora crtE and crtB and Rhodobacter capsulatus crtI genes (Ref. 1046). An Escherichia coli transformant carrying the Staphylococcus aureus crtN and the Erwinia uredovora crtE and crtB genes (Ref. 1215). Neurosporene is a substrate of CrtC from Rubrivivax gelatinosus and Rhodobacter capsulatus (photosynthetic bacteria) to produce chloroxanthin (OH-neurosporene) (Ref. 1255).	Phytoene desaturase genes (crtI), which mediate the formation of neurosporene from phytoene, have been cloned from the purple photosynthetic bacteria Rhodobacter capsulatus and Rba. sphaeroides (Ref. 1032/1033). Neurosporene is the major product of CrtI from Rubrivivax gelatinosus (purple photosynthetic bacterium) resulting in the synthesis of spheroidene, and lycopene is the minor resulting in the synthesis of spirilloxanthin (Ref. 1107). The crtI mutants by random and site-directed mutagenesis of Rhodobacter sphaeroides, which produces only neurosporene, change to prodece also lycopene (Ref. 1116).		[1005] / [1032] / [1033] / [1046] / [1052] / [1054] / [1057] / [1060] / [1061] / [1062] / [1073] / [1089] / [1100] / [1107] / [1116] / [1215] / [1255]
85		3,4-Dehydrolycopene/ 3,4-Didehydrolycopene	3,4-Didehydro-y,y-carotene	VCA1005	Norihiko Misawa		C₄₀H₅₄	534.857									lmax (nm): acetonitrile/methanol/THF (58:35:7) 320, 394, 470, 497, 530, %III/II=64 [Spectrum 1008] [Spectrum 1051] (Ref. 1057/1064)			FD-MS m/z: 534 (Ref. 1064)	Fluoresence (Ref. 1062)	HPLC (column; Novapak C18 (Waters) 8 X 100 mm: eluelnt; acetonitrile/methanol/THF 58:35:7: flow 2.0 ml/min) Rt=10.4 min (Ref. 1057)			3,4-Dehydrolycopene is synthesized from phytoene through five-step desaturation reactions with a phytoene desaturase enzyme derived from carotenogenic fungi such as Neurospora (Ref. 1064/1091/1135). This enzyme is NAD dependent (Ref. 1135). 3,4-Didehydrolycopene may be cyclized to torulene by the gene products of Neurospora crassa (al-2) (Ref. 1176) and Fusarium fujikuroi (carRA) (Ref. 1175) (fungus), which are bifunctional protein involved carotene cyclase and phytoene synthase activities. an Escherichia coli transformant carrying the Erwinia uredovora crtE and crtB and Neurospora crassa al-1 genes (Ref. 1064)	A phytoene desaturase gene (al-1), which mediate the formation of 3,4-dehydrolycopene from phytoene, has been cloned from the carotenogenic fungus Neurospora crassa (Ref. 1064/1091/1135).		[1057] / [1062] / [1064] / [1091] / [1135] / [1175] / [1176]
86		Torulene	3',4'-Didehydro-b,y-carotene	VCA1006	Norihiko Misawa		C₄₀H₅₄	534.857									lmax (nm): acetonitrile/methanol/THF (58:35:7) 309, 382, 467 (shoulder), 489, 520, %III/II=46 [Spectrum 1009] (Ref. 1057) methanol 309, 379, 463 (shoulder), 484, 516, %III/II=41 [Spectrum 1117]					HPLC (column; Novapak C18 (Waters) 8 X 100 mm: eluelnt; acetonitrile/methanol/THF 58:35:7: flow 2.0 ml/min) Rt=13.8 min (Ref. 1057)	Neurospora crassa (Ref. 1135)		The Escherichia coli transformant carrying the Erwinia uredovora crtE and crtB genes, the crtI gene (crtI14) shuffled between the corresponding genes of E. uredovora and E. herbicola, and the crtY gene (crtY2) shuffled between the corresponding genes of E. uredovora and E. herbicola produces torulene (Ref. 1049). Phytoene is desaturated to 3,4-didehydrolycopene by a five-step desaturase, Al-1, from Neurospora crassa. Since g-carotene is not substrate of Al-1, torulene must be produced from 3,4-didehydrolycopene by cyclization (Ref. 1135). 3,4-Didehydrolycopene may be cyclized to torulene by the gene products of Neurospora crassa (al-2) (Ref. 1176) and Fusarium fujikuroi (carRA) (Ref. 1175) (fungus), which are bifunctional protein involved carotene cyclase and phytoene synthase activities.	A special phytoene desaturase gene (crtI14), which has been shuffled between the crtI genes of the epiphytic bacteria Erwinia uredovora and E. herbicola, combined with a special lycopene cyclase gene (crtY2), which has been shuffled between the crtY genes of E. uredovora and E. herbicola, has mediated the synthetic reaction of torulene from phytoene as the substrate(Ref. 1049).	DNA shuffling technology has made it possible to create torulene-producing E. coli by shuffling the crtI and crtY genes between Erwinia species (Ref. 1049).	[1049] / [1057] / [1135] / [1175] / [1176]
87		g-Carotene/ b,y-Carotene	b,y-Carotene	VCA1007	Norihiko Misawa		C₄₀H₅₆	536.873									lmax (nm): acetonitrile/methanol/THF (58:35:7) 284, 356, 440 (shoulder), 462, 492, %III/II=41.7 [Spectrum 1010] (Ref. 1057/1103); methanol 459, 485 [Spectrum 1118] (Ref. 1055)		¹H-NMR (CDCl3) (Ref. 1103)	FD-MS m/z: 536 (Ref. 1103/1105)		HPLC (column; Novapak C18 (Waters) 8 X 100 mm: eluelnt; acetonitrile/methanol/THF 58:35:7: flow 2.0 ml/min) Rt=14.8 min (Ref. 1057)	Chloroflexus aurantiacus (Ref. 1105) and Chloroflexus aggregans (S. Takaichi) (Ref. 1106) (green filamentous bacteria) Chlorobium (present name, Chlorobaculum) tepidum (green sulfer bacteria) (Ref. 1103) Rhodococcus rhodochrous (Nocardioform actinomycetes) (Ref. 1111) Erythrobacter longus (aerobic photosynthetic bacterium) (Ref. 1055)		g-Carotene is the biosynthetic intermediate through cyclization reactions from lycopene to b-carotene. A mutant of Rhodococcus rhodochrous accumulats g-karotene and 4-keto-g-karotene (Ref. 1111). [Table 1031]	A lycopene b-monocyclase gene crtYm is isolated from a unique marine bacterium that produces myxol (Ref. 1241), and crtLm is isolated from Rhodococcus erythropolis and Deinococcus radiodurans (bacteria) (Ref. 1278).		[1055] / [1057] / [1103] / [1105] / [1106] / [1111] / [1241] / [1278]
88		b-Zeacarotene	7',8'-Dihydro-b,y-carotene	VCA1008	Norihiko Misawa		C₄₀H₅₈	538.889									lmax (nm): acetonitrile/methanol/THF (58:35:7) 254, 321, 408 (shoulder), 429, 453, %III/II=52.6 [Spectrum 1011] (Ref. 1056/1057); methanol 314, 405 (shoulder), 426, 451 %III/II=52 [Spectrum 1119]			FD-MS m/z: 538 (Ref. 1056)		HPLC (column; Novapak C18 (Waters) 8 X 100 mm: eluelnt; acetonitrile/methanol/THF 58:35:7: flow 2.0 ml/min) Rt=18.3 min (Ref. 1056/1057)			b-Zeacarotene is the biosynthetic intermediate through cyclization reactions by lycopene b-cyclase from neurosporene to 7,8-dihyro-b-carotene (Ref. 1056). In E. coli neurosporene background, lycopene b-cyclase from Arabidopsis produces b-zeacarotene (Ref. 1015).			[1015] / [1056] / [1057]
89		Dihydro-b-carotene/ 7,8-Dihydro-b-carotene	7,8-Dihydro-b,b-carotene	VCA1009	Norihiko Misawa		C₄₀H₅₈	538.889									lmax (nm): acetonitrile/methanol/THF (58:35:7) 255, 324, 410 (shoulder), 429, 454, %III/II=54.0 [Spectrum 1012] (Ref. 1056/1057)		¹H-NMR (CDCl₃): 1.01 s (16, 17-H₃), 1.03 s (16', 17'-H₃), 1.43 (2-H₂), 1.47 (2'-H₂), 1.58 (3-H₂), 1.62 s (18-H₃), 1.72 s (18'-H₃), 1.86 s (19-H₃), 1.92 t (J=7.0 Hz; 4-HH₂), 1.95 s (20-H₃), 1.97 s (19', 20'-H₃), 2.02 t (J=6.5 Hz; 4'-H₂), 2.12 (7, 8-H₂), 5.98 d (J=11.0 Hz; 10-H), 6.50 dd (J=11.0, 15.0 Hz; 11-H) (Ref. 1056)	FD-MS m/z: 538 (Ref. 1056)		HPLC (column; Novapak C18 (Waters) 8 X 100 mm: eluelnt; acetonitrile/methanol/THF 58:35:7: flow 2.0 ml/min) Rt=24.1 min (Ref. 1056/1057)	Chlorobium phaeobacteroides 1549 (new name, Chlorobaculum limnaeum 1549; green-sulfur photosynthetic bacterium), the content of this carotenoid incleases under high light culture (Ref. 1282).		An Escherichia coli transformant carrying the Erwinia uredovora crtE and crtB and Rhodobacter capsulatus crtI genes, and lycopene cyclase gene (E. uredovora crtY or Capsicum annuum (higher plant) lcy) (Ref. 1056)	Escherichia coli, which carries the crtE, crtB and crtY genes from the epiphytic bacterium Erwinia uredovora, and the crtI gene from the purple photosynthetic bacterium Rhodobacter capsulatus, has synthesized 7,8-Dihydro-b-carotene from farnesyl diphosphate (FPP). (Ref. 1056) When the lycopene cyclase gene from the epiphytic bacterium Erwinia uredovara (crtY) or a higher plant red papper Capsicum annuum (lcy-beta) has been expressed in Escherichia coli with a neurospore background, this unnatural carotenoid has been produced (Ref. 1056). The lcy-beta (crtL) genes from Synechococus sp. PCC 7942 and Lycopersicon esculentum (tomato) have also seemed to have the same characteriatics. This result shows that the substrate of CrtY or Lcy-beta (Crt-L) is not only y end group but also 7,8-dihydro-y end group. When the substrate is z-carotene, the product is tetrahydro-b-carotene (Ref. 1056).		[1056] / [1057] / [1282]
90		Parasiloxanthin/ 7,8-Dihydrozeaxanthin	(3R,3'R)-7,8-Dihydro--b,b-carotene-3,3'-diol	VCA1010	Norihiko Misawa		C₄₀H₅₈O₂	570.887			202 C (Ref. 1058)						lmax (nm): methanol 408 (shoulder), 428, 453, %III/II=64.5 [Spectrum 1120] (Ref. 1056) petroleum ether 405, 427, 452 (Ref. 1058)			¹H-NMR (CDCl₃): 1.04 s (16-H₃), 1.07 s (16', 17'-H₃), 1.08 s (17-H₃), 1.32 d (J=4.6 Hz; 3-OH), 1.36 d (J=4.4 Hz; 3'-OH), 1.44 t (J=12.0 Hz; 2-Hax), 1.48 t (J=11.8 Hz; 2'-Hax), 1.65 s (18-H₃), 1.72 td (2-Heq), 1.74 s (18'-H₃), 1.77 td (J=2.9, 12.5 Hz; 2'-Heq), 1.86 s (19-H₃), 1.95 s (20-H₃), 1.97 s (19', 20'-H₃), 2.00 dd (J=6.0, 15.0 Hz; 4-Hax), 2.06 dd (J=4.3, 12.6 Hz; 4'-Hax), ca. 2.13 (7, 8-H₂), 2.25 dd (J=4.8, 15.8 Hz; 4-Heq), 2.39 dd (J=5.3, 16.8 Hz; 4'-Heq), 3.94 m (3-H), 4.00 m (3'-H), 5.98 d (J=11.0 Hz; 10-H), 6.50 dd (J=11.0, 15.0 Hz; 11-H) (Ref. 1056)	FD-MS m/z: 570 (Ref. 1056) MS m/z: 570 (M), 552 (M-18), 478 (M-92), 417 (M-153), 399 (M-153-18), 325 (M-153-92) (Ref. 1058)		Fin and skin of Parasilurus asotus (Japanese catfish ) (Ref. 1058)		an Escherichia coli transformant carrying the Erwinia uredovora crtE, crtB, crtY and crtZ and Rhodobacter capsulatus crtI genes (Ref. 1056)	Escherichia coli, which carries the crtE, crtB, crtY and crtZ genes from the epiphytic bacterium Erwinia uredovora, and the crtI gene from the purple photosynthetic bacterium Rhodobacter capsulatus, has synthesized parasiloxanthin from farnesyl diphosphate (FPP). (Ref. 1056)		[1056] / [1058]
91		7,8-Dihydroparasiloxanthin/ 7,8,7',8'-Tetrahydrozeaxanthin	7,8,7',8'-Tetrahydro--b,b-carotene-3,3'-diol	VCA1011	Norihiko Misawa		C₄₀H₆₀O₂	572.903									lmax (nm): petroleum ether 380, 401, 426 (Ref. 1058)		¹H-NMR (CDCl₃): 1.04 s (16-H₃), 1.08 s (17-H₃), 1.65 s (18-H₃), 1.86 s (19-H₃), 1.94 s (20-H₃), 2.11 (7, 8-H₂) (Ref. 1058)				Fin and skin of Parasilurus asotus (Japanese catfish) (Ref. 1058)					[1058]
92		Antheraxanthin	(3S,5R,6S,3'R)-5,6-Epoxy-5,6-dihydro-b,b-carotene-3,3'-diol	VCA1012	Norihiko Misawa		C₄₀H₅₆O₃	584.871			197 C(Ref. 1090)						lmax (nm) (e): diethyl ether/isopentane/ethanol (5:5:2) 269 (20.5), 332 (13.5), 422 (94.0), 445 (136.0), 473 (122.0)(Ref. 1090)		¹H-NMR (CDCl₃): 0.980 s (16-H₃), 1.074 s (16', 17'-H₃), 1.151 s (17-H₃), 1.189 s (18-H₃), 1.34 d (J=5 Hz; 3'-OH), 1.737 s (18'-H₃), 1.927 s (19-H₃), 1.965 s (20-H₃), 1.968 s (19'-H₃), 1.973 s (20'-H₃), 3.88 (3-Hax), ca. 4.00 (3'-Hax), 5.88 (7-H) (Ref. 1090/0079) (Ref. 1329)		CD l nm (de) diethyl ether/isopentane/ethanol (5:5:2) 180 C: 217 (-38.1), 242 (36.4), 280 (-55.0), 330 (6.2), 345 (10.6), 408 (2.3), 435 (2.8 , 465 (3.8), 493 (5.2); RT: 216 ()-13.2, 239 (10.3), 275 (-21.1), 335 (5.7) (Ref. 1090/0079) (Ref. 1329)		Plants. (3S,5R,6S,3'R) and (3S,5S,6R,3'R) antheraxanthin are found from the common freshwater goby Rhinogobius brunneus (Ref. 1329).		Antheraxanthin is an intermediate through epoxydation reaction from zeaxanthin to violaxanthin by biosynthesis and through de-epoxidation reaction from violaxanthin to zeaxanthin by xanthophyll-cycle. Antheraxanthin is the substrate of violaxanthin de-epoxidase (Ref. 1143/1144). [Table 1032]			[0079] / [1090] / [1143] / [1144] / [1329]
93		b-Cryptoxanthin	(3R)-b,b-Caroten-3-ol	VCA1013	Norihiko Misawa		C₄₀H₅₆O	552.872		Induced colon tumor of rats was lowered by the diet supplemented with 25 ppm b-cryptoxanthin (Ref. 1203). The cancer preventive activity of phytoene was confirmed in phytoene producing mammalian cells (Ref. 1207). Lutein and b-cryptoxanthin suppressed tumorigenesis in skin and colon in mice (Ref. 1208).							lmax (nm): methanol 272, 447, 473, %III/II=16 [Spectrum 1121] (Ref. 1055)		¹H-NMR (CDCl₃): 1.03 s (16', 17'-H₃), 1.07 s (16, 17-H₃), 1.35 d (J=5.1 Hz; 3-OH), ca. 1.46 (2'-H₂), 1.48 dd (2-Hax), ca. 1.62 (3'-H₂), 1.72 s (18'-H₃), 1.74 s (18-H₃), ca. 1.77 (2-Heq), 1.97 s (19, 20, 19', 20'-H₃), ca. 2.02 (4'-H₂), 2.04 dd (4-Hax), 2.39 dd (4-Heq), 4.00 m (3-Hax) (Ref. 1055)	FD-MS m/z: 552 (Ref. 1055)	CD spectrum is the same with that of (3R,3'R)-zeaxanthin (Ref. 1055)		Erythrobacter longus (aerobic photosynthetic bacterium) (Ref. 1055) Anacystis nidulans (cyanobacterium) (Ref. 1077)		b-Cryptoxanthin is the biosynthetic intermediate through hydroxylation reactions from b-carotene to zeaxanthin. [Table 1033]			[1055] / [1077] / [1203] / [1207] / [1208]
94		Adonirubin/ Phoenicoxanthin/ 3-Hydroxycanthaxanthin	(3S)-3-Hydroxy-b,b-carotene-4,4'-dione	VCA1014	Norihiko Misawa		C₄₀H₅₂O₃	580.839									lmax (nm): benzene 483 (Ref. 0208); ethanol 477 (Ref. 0152)				CD l nm (de) diethyl ether/isopentane/ethanol (5:5:2): 242 (-14.0), 271 (4.0), 314 (-18.3), 367 (2.0) (Ref. 0208)		Agrobacterium aurantiacum (marine bacterium) (Ref. 0208) Rhizobium lupini (soil and root nodule bacterium) (Ref. 0152)		Phoenicoxanthin is one of biosynthetic intermediates through hydroxylation and ketolation reactions from b-carotene to astaxanthin (Ref. 0202). an Escherichia coli transformant carrying the Erwinia uredovora crtE, crtB, crtI, crtY and crtZ and A. aurantiacum crtW genes, and an E. coli transformant carrying the E. uredovora crtE, crtB, crtI and crtY and A. aurantiacum crtZ and crtW genes (Ref. 0202)			[0152] / [0202] / [0208]
95		3-Hydroxyechinenone/ 3-OH-Echinenone	(3S)-3-Hydroxy-b,b-caroten-4-one	VCA1015	Norihiko Misawa		C₄₀H₅₄O₂	566.856									lmax (nm): ethanol 460 (Ref. 1082); ethanol 466 (Ref. 0152); benzene 477 (Ref. 0208)			566 [M], [M-16], [M-18], [M-92], [M-106], [M-154] (Ref. 1082)	CD l nm (de) diethyl ether/isopentane/ethanol (5:5:2): 259 (1.4), 300 (-15.2) (Ref. 0208)	3'-OH-Echinenone is eluted faster than 3-OH-echinenone on C18-HPLC.	Aphanocapsa strain PCC 6714 (cyanobacterium) (Ref. 1082) Agrobacterium aurantiacum (marine bacterium) (Ref. 0208) Rhizobium lupini (soil and root nodule bacterium) (Ref. 0152)		3-Hydroxyechinenone is one of biosynthetic intermediates through hydroxylation and ketolation reactions from b-carotene to astaxanthin (Ref. 0202). an Escherichia coli transformant carrying the Erwinia uredovora crtE, crtB, crtI, crtY and crtZ and A. aurantiacum crtW genes, and an E. coli transformant carrying the E. uredovora crtE, crtB, crtI and crtY and A. aurantiacum crtZ and crtW genes (Ref. 0202)			[0152] / [0202] / [0208] / [1082]
96		3'-Hydroxyechinenone/ 3'-OH-Echinenone	(3'R)-3'-Hydroxy-b,b-caroten-4-one	VCA1016	Norihiko Misawa		C₄₀H₅₄O₂	566.856		A water-soluble orange carotenoid protein (OCP) isolated from Arthrospira maxima contains 3'-hydroxyechinenone, and the crystal structure is determined at a resolution of 2.1 A. OCP forms a homodimer with one carotenoid molecule per monomer (Ref. 1240).							lmax (nm): acetone 459, 471 (shoulder) (Ref. 1081); acetone 430 (shoulder), 458, 475 (shoulder); hexane 420 (shoulder), 450, 470 (shoulder); methanol 458, 465 (shoulder) (Ref. 1083); benzene 469 (Ref. 0208); methanol [Spectrum 1122]		¹H-NMR (CDCl₃): 1.07 s (16', 17'-H₃), 1.19 s (16, 17-H₃), 1.74 s (18'-H₃), 1.85 t (J=7 Hz, 2-H), 1.87 s (18-H₃), 1.97 s (19'-H₃), 1.98 s (20, 20'-H₃), 2.00 s (19-H₃), 2.51 t (J=7 Hz, 3-H) (Ref. 1081)	566 [M], [M-18], [M-151], [M-153] (Ref. 1083)	CD l nm (de) isopropanol: 214 (18), 237 (-4.6), 250 (0), 263 (1.4), 273 (0), 303 (-5.2), 360 (0), 440 (-1.7), 460 (0), 501 (3.0) (Ref. 1081); diethyl ether/isopentane/ethanol (5:5:2): 234 (-11.3), 259 (4.9), 299 (-14.1), 359 (1.9) (Ref. 0208)	3'-OH-Echinenone is eluted faster than 3-OH-echinenone on C18-HPLC.	Botryococcus braunii (Botryococcaceae, Chlorococcales) (Ref. 1081) Spirulina maxima, Aphanizomenon flos-aquae, Microcystis aeruginosa, Oscillatoria rubescens and Anthrospira sp. (Ref. 1083), Synechocystis sp. PCC 6803 (Ref. 1222), Arthrospora maxima (Ref. 1240) (cyanobacteria) Agrobacterium aurantiacum (marine bacterium) (Ref. 0208)		3'-Hydroxyechinenone is one of biosynthetic intermediates through hydroxylation and ketolation reactions from b-carotene to astaxanthin (Ref. 0202). an Escherichia coli transformant carrying the Erwinia uredovora crtE, crtB, crtI, crtY and crtZ and A. aurantiacum crtW genes, and an E. coli transformant carrying the E. uredovora crtE, crtB, crtI and crtY and A. aurantiacum crtZ and crtW genes (Ref. 0202) This is produced by CrtR from echinenone and one of end products in Synechocystis sp. PCC 6803 (Ref. 1222).		Main carotenoid of the water soluble carotenoprotein of cyanobacteria, Spirulina maxima, Aphanizomenon flos-aquae and Microcystis aeruginosa (Ref. 1083) This carotenoid is bound to a water soluble protein, which is encoded by gene slr 1963 in the Kazusa DNA sequence data bank containing the Synechosystis sp. PCC 6803 genome (Ref. 1130).	[0202] / [0208] / [1081] / [1083] / [1130] / [1222] / [1240]
97		Zeaxanthin diglucoside/ Zeaxanthin b-D-diglucoside	(3R,3'R)-3,3'-Di(b-D-glucopyranosyloxy)-b,b-carotene	VCA1017	Norihiko Misawa		C₅₂H₇₆O₁₂	893.153															Erwinia uredovora and E. herbicola (epiphytic nonphotosynthetic bacteria) (Ref. 0201)		Zeaxanthin b-D-diglucoside is synthesized from zeaxanthin and UDP-glucose with zeaxanthin glucosyltransferase (the Erwinia crtX gene product) (Ref. 1051). an Escherichia coli transformant carrying the intact crt gene cluster from E. uredovora or E. herbicola (Ref. 0201/1002)	Escherichia coli, which carries the crtE, crtB, crtI, crtY, crtZ, and crtX genes derived from the epiphytic bacteria Erwinia species, has produced zeaxanthin b-D-diglucoside (Ref. 1002/1050).		[0201] / [1002] / [1050] / [1051]
98		Astaxanthin diglucoside/ Astaxanthin b-D-diglucoside	(3S,3'S)-3,3'-Di(b-D-glucopyranosyloxy)-b,b-carotene-4,4'-dione	VCA1018	Norihiko Misawa		C₅₂H₇₂O₁₄	921.120									lmax (nm): CHCl3-MeOH (2:1) 492 (Ref. 1027)		¹H-NMR d(400 MHz, CDCl3-CD3OD 2:1): 1.19 (6H, s, 17 and 17'-Me), 1.31 (6H, s, 16 and 16'-Me), 1.86 (6H, s, 18 and 18'-Me), 1.94 (2H, m, 2 and 2'-H), 1.95-1.97 (12H, s, 19, 20, 19', 20'-Me), 2.18 (2H, m, 2 and 2'-H), 3.27 (2H, m, 5""-H), 3.36 (2H, dd, J 8, 9, 2""-H), 3.41 (2H, t, J 9, 4""-H), 3.43 (2H, t, J 9, 3""-H), 3.70 (2H, dd, J 5, 12, 6""-H), 3.83 (2H, dd, J 3, 12, 6""-H), 4.49 (2H, d, J 8, 1""-H), 4.77 (2H, m, 3 and 3'-H), 6.18-6.67 (14H, m, olefinic-H) (Ref. 1027)	FABMS (pos.) m/z: 921 [M+H]⁺(Ref. 1027)					an Escherichia coli transformant carrying the intact crt gene cluster from Erwinia uredovora and the Agrobacterium aurantiacum crtW gene (Ref. 1027)	Escherichia coli, which carries the crtE, crtB, crtI, crtY, crtZ and crtX genes derived from the epiphytic bacterium Erwinia uredovora and the crtW gene derived from the marine bacterium Agrobacterium aurantiacum, has produced astaxanthin b-D-diglucoside in addition to astaxanthin b-glucoside (Ref. 1002/1027).		[1002] / [1027]
99		Adonixanthin 3'-b-D-glucoside/ Adonixanthin 3'-glucoside	(3S,3'R)-3-Hydroxy-3'-(b-D-glucopyranosyloxy)-b,b-caroten-4-one	VCA1019	Norihiko Misawa		C₄₆H₆₄O₈	744.996									lmax (nm): CHCl3-MeOH (2:1) 487 (Ref. 1027)		¹H-NMR d(400 MHz, CDCl3-CD3OD 2:1): 1.03 (6H, s, 16' and 17'-Me), 1.18 (3H, s, 17-Me), 1.29 (3H, s, 16-Me), 1.52 (1H, t, J 12, 2'-H), 1.69 (3H, s, 18'-Me), 1.79 (1H, m, 2-H), 1.83 (1H, m, 2'-H), 1.87 (3H, s, 18-Me), 1.92-1.96 (12H, s, 19, 20, 19', and 20'-Me), 2.06 (1H, m, 2-H), 2.08 (1H, m, 4'-H), 2.42 (1H, dd, J 4 and 17, 4'-H), 3.19 (1H, m, 2""-H), 3.27 (1H, m, 5""-H), 3.38 (2H, m, 3"" and 4""-H), 3.72 (1H, dd, J 5 and 12, 6""-H), 3.83 (1H, dd, J 3 and 12, 6""-H), 4.05 (1H, m, 3'-H), 4.28 (1H, dd, J 6 and 14, 3-H), 4.42 (1H, d, J 8 , 1""-H), 6.05-6.70 (14H, olefinic protons) (Ref. 1027)	FABMS (pos.) m/z: 745 [M+H]⁺ (Ref. 1027)					an Escherichia coli transformant carrying the intact crt gene cluster except for crtZ from Erwinia uredovora and the Agrobacterium aurantiacum crtZ and crtW genes (Ref. 1027)	Escherichia coli, which carries the crtE, crtB, crtI, crtY and crtX genes derived from the epiphytic bacterium Erwinia uredovora, and the crtZ and crtW genes derived from the marine bacterium Agrobacterium aurantiacum, has produced adonixanthin 3?-b-D-glucoside (Ref. 1027).		[1027]
100		Flexixanthin/ 4-Oxosaproxanthin	(3S)-3,1'-Dihydroxy-3',4'-didehydro-1',2'-dihydro-b,y-caroten-4-one	VCA1020	Norihiko Misawa		C₄₀H₅₄O₃	582.855									lmax (nm): acetone 483, 510 (Ref. 1085); acetone 478, 503 (Ref. 1086)		¹H-NMR (CDCl₃): 1.21 and 1.32 s (16,17-H₃), 1.24 s (16', 17'-H₃), 1.95 s (18-H₃), 1.98 s (19, 20, 18', 19', 20'-H₃), 2.32 d (J=7 Hz; 2'-H₂), 4.31 dd (J=6, 14 Hz; 3-H), 5.80 m (J=7, 16 Hz; 3'-H) (Ref. 1088)		CD (Ref. 1088)		Flexibacter sp. (Ref. 1085) Flexibacter strain NIVA BR6-64 (non-gliding bacterium) (Ref. 1086/1088)				Upon alkali treatment, flexixanthin is autoxidized to dehydro-flexixanthin (Ref. 1085).	[1085] / [1086] / [1088]
101		2'-Hydroxyflexixanthin/ Ketomyxol	(3S,2'S)-3,1',2'-Trihydroxy-3',4'-didehydro-1',2'-dihydro-b,y-caroten-4-one	VCA1021	Norihiko Misawa		C₄₀H₅₄O₄	598.854									lmax (nm): acetone 478, 504 (Ref. 1086); methanol 293, 317, (452), 479, 503 (Ref. 1346)		¹H-NMR (CDCl₃): 1.21 and 1.32 s (16,17-H₃), 1.95 s (18-H₃), 1.98 s (19, 20, 18', 19', 20'-H₃), 4.00 d (J=7 Hz; 2'-H), 4.31 dd (3-H), 5.71 dd (J=7, 16 Hz; 3'-H) (Ref. 1088)	MS (Ref. 1217/1218/1346)	CD in EPA of ketomyxol 2'-rhamnoside and 2'-hydroxyflexixanthin (Ref. 1219), and 4-ketomyxol 2'-fucoside (Ref. 1346)		Flexibacter strain NIVA BR6-64 (non-gliding bacterium) (Ref. 1086/1088) (3S,2'R)-2'-Hydroxyflexixanthin from Taxeobacter (gliding bacteria) (Ref. 1281) 4-Ketomyxol 2'-glycoside is found only in cyanobacteria, and the determination of the sugar moieties, including the L- or D-type and the a- or b-linkage, has been done only for a few species. (3S,2'S)-4-ketomyxol 2'-methylpentoside from Oscillatoria limosa (Ref. 1217/1219), 4-ketomyxol 2'-rhamnoside from Anacystis nidulans (Ref. 1218) and (3S,2'S)-4-ketomyxol 2'-a-L-fucoside from Anabaena sp. PCC 7120, Anabaena variabilis IAM M3 and Nostoc punctiforme PCC 73102 (Ref. 1346)				Since the name ketomyxoxanthophyll can not specify the sugar moiety and the identification of the sugar moiety is unfeasible in many cyanobacteria, the following naming convention is proposed by (Ref. 1222): when the sugar moiety is unknown, the name is ketomyxol 2'-glycoside, when known, as in the case of rhamnose and a-L-fucose, they should be named ketomyxol 2'-rhamnoside and ketomyxol 2'-a-L-fucoside, respectively.	[1086] / [1088] / [1217] / [1218] / [1219] / [1222] / [1281] / [1346]
102		Nostoxanthin	(2R,3R,2'R,3'R)-b,b-Carotene-2,3,2',3'-tetrol	VCA1022	Norihiko Misawa		C₄₀H₅₆O₄	600.870									lmax (nm): methanol 275, 341, 425 (shoulder), 448, 475, %III/II=30.9 [Spectrum 1123] (Ref. 1052/1055); acetone 431 (shoulder), 453, 480.5 (Ref. 1077); CHCl₃/methanol (2:1) (e) 456 (91.3), 484 (78.1) (Ref. 1040); ethanol 429, 449, 477 (Ref. 1345)	n_m_a_x(KBr) cm^-¹: 3390 m, 3030 w, 2960 s, 2930 s, 2860 s, 1465 m, 1445 m, 1440 w, 1380 m, 1365 m, 1265 w, 1175 w, 1125 w, 1050 m, 970 s (Ref. 1077)	¹H-NMR (CDCl₃): 1.00 s (16-H₃), 1.13 s (17-H₃), 1.72 s (18-H₃), 1.97 s (19, 20-H₃), 2.14 dd (4-Hax), 2.48 dd (4-Heq), 3.33 d (J=10.1 Hz; 2-Hax), 3.84 m (3-Hax) (Ref. 1055); CDCl₃ (Ref. 1344)	FD-MS m/z: 600 (100%), 582 (M-18, 2%) (Ref. 1053/1055)	CD spectrum is the same with that of (3R,3'R)-zeaxanthin (Ref. 1055) CD l nm (de) diethyl ether/isopentane/ethanol (5:5:2): 340 (+ 3.5), 313 (0), 282 (- 16.7), 261 (0), 245 (+ 8.8), 232 (0), 220 (- 11.9), 208 (0) (Ref. 1077); CHCl₃/methanol (2:1): 287 (-6.9), 386 (0.4) (Ref. 1040)		Erythrobacter longus (aerobic photosynthetic bacterium) (Ref. 1055) Porphyrobacter tepidarius (thermophilic aerobic photosynthetic bacterium) (Ref. 1214) Erythromicrobium based on TLC (Ref. 1237) Anacystis nidulans (cyanobacterium) (Ref. 1077) Brevundimonas sp. SD212 (marine bacterium) (Ref. 1040) Rhizobium lupini (soil and root nodule bacterium) (Ref. 1345)			Reaction products of Brevundimonas crtG expessed in E.coli with zeaxanthin background (crtE, crtB, crtI, crtY and crtZ from Pantoea) (Ref. 1344)		[1040] / [1052] / [1053] / [1055] / [1077] / [1214] / [1237] / [1344] / [1345]
103		Nostoxanthin 3-sulfate	Sodium (2R,3R,2'R,3'R)-2,2',3'-trihydroxy-b,b-Caroten-3-yl sulfate	VCA1023	Norihiko Misawa		C₄₀H₅₅O₇SNa	702.916									lmax (nm): CHCl3-MeOH (2:1) 458 and 487(Ref. 1040)	n_m_a_x(KBr)/cm^-¹: 3428 (O-H), 1253 (S=O), 1064, 965 (Ref. 1040)	¹H-NMR d(500 MHz, CDCl3-CD3OD 2:1): 0.94 and 1.06 (s, 16' and 17'-Me), 0.99 and 1.10 (s, 16 and 17-Me), 1.66 (s, 18 and 18""-Me), 1.92-1.93 (s, 19, 20, 19', and 20'-Me), 2.07 (1H, dd, J 10, 17, 4'-H), 2.28 (1H, dd, J 10, 18, 4-H), 2.39 (1H, dd, J 6, 17, 4'-H), 2.68 (1H, dd, J 7, 18, 4-H), 3.21 (1H, d, J 10, 2'-H), 3.42 (1H, d, J 10, 2-H), 3.73 (1H, dt, J 6, 10, 3'-H), 4.50 (1H, dt, J 7, 10, 3-H), 6.0-6.7 (14H, m, olefinic-H) (Ref. 1040)	FABMS (pos.) m/z: 703 [M+H]⁺ (Ref. 1040)	CD data: De 341(+1.6), 286 (-10.6) (Ref. 1040)		Flavobacterium sp. strain PC-6 (Ref. 1040)					[1040]
104		4-Ketonostoxanthin	(2R,3S,2'R,3'R)-2,3,2',3'-Tetrahydroxy-b,b-caroten-4-one	VCA1024	Norihiko Misawa		C₄₀H₅₄O₅	614.854									lmax (nm): CHCl₃/methanol (2:1) (e) 474 (80.1) (Ref. 1040); ethanol 457, 475 reduced form 429, 449, 477 (Ref. 1345)		¹H-NMR (CDCl₃/CD₃OD 2:1): 0.94 and 1.06 s (16', 17'-H₃), 1.20 and 1.22 s (16, 17-H₃), 1.66 s (18?-H₃), 1.87 s (18-H₃), 1.93-1.97 s (19, 20, 19?, 20?-H₃), 2.07 dd (J=10, 17 Hz; 4?-H), 2.39 dd (J=6, 17 Hz; 4?-H), 3.21 d (J=10 Hz; 2?-H), 3.45 d (J=11.5 Hz; 2-H), 3.73 dt (J=6, 10 Hz; 3?-H), 4.11 d (J=11.5 Hz; 3-H) (Ref. 1040); (CDCl3) (Ref. 1343)	EIMS (Ref. 1343)	CD l nm (de) CHCl₃/methanol (2:1): 304 (-7.5), 394 (0.4) (Ref. 1040); EPA (Ref. 1343); acetylated in dioxane (Ref. 0152)		Pseudomonas paucimobilis IFO 13935 (Sphingomonas paucimobilis) (Ref. 1040) Brevundimonas sp. SD212 (marine bacterium) (Ref. 1343) Rhizobium lupini (soil and root nodule bacterium) (Ref. 0152/1345)					[0152] / [1040] / [1343] / [1345]
105		Thermozeaxanthin-13/ Zeaxanthin glucoside ester	(3R,3'R)-3'-[(6-O-11-Methyldodecanoyl-b-D-gluycopyranosyl)oxy]-b,b-caroten-3-ol	VCA1025	Norihiko Misawa		C₅₉H₉₀O₈	927.341									lmax (nm): acetone 452(Ref. 1042)		¹H-NMR d (500 MHz, CDCl₃) (G: glucoside moiety, F: fatty acid moiety): 0.86 (6H, d, J=6 Hz, F12, F13-H₃), 1.07 (12H, s, 16, 17, 16', 17'-H₃), 1.15 (2H, m, F10-H₂), 1.23-1.34 (bulk methylenes of fatty acid moiety), 1.48 (1H, m, 2'-H), 1.50 (1H, m, F11-H), 1.58 (1H, m, 2-H), 1.62 (2H, m, F3-H₂), 1.74 (6H, s, 18, 18'-H₃), 1.77 (1H, m, 2'-H), 1.89 (1H, m, 2-H), 1.96-1.98 (12H, s, 19, 20, 19', 20'-H₃), 2.04 (1H, m, 4'-H), 2.13 (1H, m, 4-H), 2.36 (2H, t, J=8 Hz, F2-H₂), 2.39 (1H, m, 4'-H), 2.43 (1H, m, 4-H), 3.37 (1H, dd, J=8, 9 Hz, G2-H), 3.41 (1H, t, J=9 Hz, G4-H), 3.48 (1H, m, G5-H), 3.59 (1H, t, J=9 Hz, G3-H), 4.00 (1H, m, 3'-H), 4.03 (1H, m, 3-H), 4.31 (1H, dd, J=2, 12 Hz, G6-H), 4.44 (1H, d, J=8 Hz, G1-H), 4.48 (1H, dd, J=5, 12 Hz, G6-H), 6.1-6.7 (14H, olefinic-H) (Ref. 1042)		CD data: De 286 (-11.3), 248 (7.6) (Ref. 1042)	HPLC (column: TSK gel ODS-80Ts (Tosoh) 0.4615 cm, eluent and flow: 1.0 ml/min, H2O-MeOH 5:95 for 5 min, then 5 min-linear gradient MeOH-THF 7:3) tR=11.6 min (Ref. 1041)	Thermus themophilus (thermophilic eubacterium)(Ref. 1042)	Stabilization of liposomal membrans (Ref. 1043)			DELETD 1	[1041] / [1042] / [1043]
106		Thermozeaxanthin-15/ Zeaxanthin glucoside ester	(3R,3'R)-3'-[(6-O-13-Methyltetradecanoyl-b-D-gluycopyranosyl)oxy]-b,b-caroten-3-ol	VCA1026	Norihiko Misawa		C₆₁H₉₄O₈	955.394		Stabilization of liposomal membrans (Ref. 1043)							lmax (nm): acetone 452 (Ref. 1042)		¹H-NMR d (500 MHz, CDCl₃) (G: glucoside moiety, F: fatty acid moiety): 0.86 (6H, d, J=6 Hz, F14, F15-H₃), 1.07 (12H, s, 16, 17, 16', 17'-H₃), 1.15 (2H, m, F12-H₂), 1.23-1.34 (bulk methylenes of fatty acid moiety), 1.48 (1H, m, 2'-H), 1.50 (1H, m, F13-H), 1.58 (1H, m, 2-H), 1.62 (2H, m, F3-H₂), 1.74 (6H, s, 18, 18'-H₃), 1.77 (1H, m, 2'-H), 1.89 (1H, m, 2-H), 1.96-1.98 (12H, s, 19, 20, 19', 20'-H₃), 2.04 (1H, m, 4'-H), 2.13 (1H, m, 4-H), 2.36 (2H, t, J=8 Hz, F2-H₂), 2.39 (1H, m, 4'-H), 2.43 (1H, m, 4-H), 3.37 (1H, dd, J=8, 9 Hz, G2-H), 3.41 (1H, t, J=9 Hz, G4-H), 3.48 (1H, m, G5-H), 3.59 (1H, t, J=9 Hz, G3-H), 4.00 (1H, m, 3'-H), 4.03 (1H, m, 3-H), 4.31 (1H, dd, J=2, 12 Hz, G6-H), 4.44 (1H, d, J=8 Hz, G1-H), 4.48 (1H, dd, J=5, 12 Hz, G6-H), 6.1-6.7 (14H, olefinic-H) (Ref. 1042)	HRFABMS (pos.) m/z: 955.7029 [M+H]⁺ (Ref. 1042)		HPLC (column: TSK gel ODS-80Ts (Tosoh) 0.4615 cm, eluent and flow: 1.0 ml/min, H2O-MeOH 5:95 for 5 min, then 5 min-linear gradient MeOH-THF 7:3) tR=11.9 min (Ref. 1041)	Thermus themophilus (thermophilic eubacterium) (Ref. 1042)					[1041] / [1042] / [1043]
107		Thermozeaxanthin-17/ Zeaxanthin glucoside ester	(3R,3'R)-3'-[(6-O-15-Methylhexadecanoyl-b-D-gluycopyranosyl)oxy]-b,b-caroten-3-ol	VCA1027	Norihiko Misawa		C₆₃H₉₈O₈	983.447		Stabilization of liposomal membrans (Ref. 1043)							lmax (nm): acetone 452 (Ref. 1042)		¹H-NMR d (500 MHz, CDCl₃) (G: glucoside moiety, F: fatty acid moiety): 0.86 (6H, d, J=6 Hz, F16, F17-H₃), 1.07 (12H, s, 16, 17, 16', 17'-H₃), 1.15 (2H, m, F14-H₂), 1.23-1.34 (bulk methylenes of fatty acid moiety), 1.48 (1H, m, 2'-H), 1.50 (1H, m, F15-H), 1.58 (1H, m, 2-H), 1.62 (2H, m, F3-H₂), 1.74 (6H, s, 18, 18'-H₃), 1.77 (1H, m, 2'-H), 1.89 (1H, m, 2-H), 1.96-1.98 (12H, s, 19, 20, 19', 20'-H₃), 2.04 (1H, m, 4'-H), 2.13 (1H, m, 4-H), 2.36 (2H, t, J=8 Hz, F2-H₂), 2.39 (1H, m, 4'-H), 2.43 (1H, m, 4-H), 3.37 (1H, dd, J=8, 9 Hz, G2-H), 3.41 (1H, t, J=9 Hz, G4-H), 3.48 (1H, m, G5-H), 3.59 (1H, t, J=9 Hz, G3-H), 4.00 (1H, m, 3'-H), 4.03 (1H, m, 3-H), 4.31 (1H, dd, J=2, 12 Hz, G6-H), 4.44 (1H, d, J=8 Hz, G1-H), 4.48 (1H, dd, J=5, 12 Hz, G6-H), 6.1-6.7 (14H, olefinic-H) (Ref. 1042)	HRFABMS (pos.) m/z: 983.7336 [M+H]⁺ (Ref. 1042)		HPLC (column: TSK gel ODS-80Ts (Tosoh) 0.4615 cm, eluent and flow: 1.0 ml/min, H2O-MeOH 5:95 for 5 min, then 5 min-linear gradient MeOH-THF 7:3) tR=12.3 min (Ref. 1041)	Thermus themophilus (thermophilic eubacterium) (Ref. 1042)					[1041] / [1042] / [1043]
108		Thermobiszeaxanthin-13-13/ Zeaxanthin diglucoside diester	(3R,3'R)-3,3'-Di[(6-O-11-methyldodecanoyl-b-D-gluycopyranosyl)oxy]-b,b-carotene	VCA1028	Norihiko Misawa		C₇₈H₁₂₄O₁₄	1285.811									lmax (nm): acetone 452 (Ref. 1042)		¹H-NMR d (500 MHz, CDCl₃) (G: glucoside moiety, F: fatty acid moiety): 0.86 (12H, d, J=6 Hz, F12, F13-H₃), 1.07 (12H, s, 16, 17-H₃), 1.15 (4H, m, F10-H₂), 1.23-1.34 (bulk methylenes of fatty acid moiety), 1.50 (2H, m, F11-H), 1.58 (2H, m, 2-H), 1.62 (4H, m, F3-H₂), 1.74 (6H, s, 18-H₃), 1.89 (2H, m, 2-H), 1.96-1.98 (12H, s, 19, 20-H₃), 2.13 (2H, m, 4-H), 2.36 (4H, t, J=8 Hz, F2-H₂), 2.43 (2H, m, 4-H), 3.37 (2H, dd, J=8, 9 Hz, G2-H), 3.41 (2H, t, J=9 Hz, G4-H), 3.48 (2H, m, G5-H), 3.59 (2H, t, J=9 Hz, G3-H), 4.03 (2H, m, 3-H), 4.31 (2H, dd, J=2, 12 Hz, G6-H), 4.44 (2H, d, J=8 Hz, G1-H), 4.48 (2H, dd, J=5, 12 Hz, G6-H), 6.1-6.7 (14H, olefinic-H) (Ref. 1042)	HRFABMS (pos.) m/z: 1285.9069 [M+H]⁺ (Ref. 1042)	CD data: De 284 (-13.5), 248 (+5.8) (Ref. 1042)	HPLC (column: TSK gel ODS-80Ts (Tosoh) 0.4615 cm, eluent and flow: 1.0 ml/min, H2O-MeOH 5:95 for 5 min, then 5 min-linear gradient MeOH-THF 7:3) tR=12.5 min (Ref. 1041)	Thermus themophilus (thermophilic eubacterium) (Ref. 1042)					[1041] / [1042]
109		Thermobiszeaxanthin-13-15/ Zeaxanthin diglucoside diester	(3R,3'R)-3-[(6-O-13-Methyltetradecanoyl-b-D-gluycopyranosyl)oxy]-3'-[(6-O-11-methyldodecanoyl-b-D-gluycopyranosyl)oxy]-b,b-carotene	VCA1029	Norihiko Misawa		C₈₀H₁₂₈O₁₄	1313.864									lmax (nm): acetone 452 (Ref. 1042)		¹H-NMR d (500 MHz, CDCl₃) (G: glucoside moiety, F: fatty acid moiety): 0.86 (12H, d, J=6 Hz, F14, F15, F12', F13'-H₃), 1.07 (12H, s, 16, 17-H₃), 1.15 (4H, m, F12, F10'-H₂), 1.23-1.34 (bulk methylenes of fatty acid moiety), 1.50 (2H, m, F13, F11'-H), 1.58 (2H, m, 2-H), 1.62 (4H, m, F3-H₂), 1.74 (6H, s, 18-H₃), 1.89 (2H, m, 2-H), 1.96-1.98 (12H, s, 19, 20-H₃), 2.13 (2H, m, 4-H), 2.36 (4H, t, J=8 Hz, F2-H₂), 2.43 (2H, m, 4-H), 3.37 (2H, dd, J=8, 9 Hz, G2-H), 3.41 (2H, t, J=9 Hz, G4-H), 3.48 (2H, m, G5-H), 3.59 (2H, t, J=9 Hz, G3-H), 4.03 (2H, m, 3-H), 4.31 (2H, dd, J=2, 12 Hz, G6-H), 4.44 (2H, d, J=8 Hz, G1-H), 4.48 (2H, dd, J=5, 12 Hz, G6-H), 6.1-6.7 (14H, olefinic-H) (Ref. 1042)			HPLC (column: TSK gel ODS-80Ts (Tosoh) 0.4615 cm, eluent and flow: 1.0 ml/min, H2O-MeOH 5:95 for 5 min, then 5 min-linear gradient MeOH-THF 7:3) tR=12.7 min (Ref. 1041)	Thermus themophilus (thermophilic eubacterium) (Ref. 1042)				1	[1041] / [1042]
110		Thermobiszeaxanthin-15-15/ Zeaxanthin diglucoside diester	(3R,3'R)-3,3'-Di[(6-O-13-methyltetradecanoyl-b-D-gluycopyranosyl)oxy]-b,b-carotene	VCA1030	Norihiko Misawa		C₈₂H₁₃₂O₁₄	1341.917									lmax (nm): acetone 452 (Ref. 1042)		¹H-NMR d (500 MHz, CDCl₃) (G: glucoside moiety, F: fatty acid moiety): 0.86 (12H, d, J=6 Hz, F14, F15-H₃), 1.07 (12H, s, 16, 17-H₃), 1.15 (4H, m, F12-H₂), 1.23-1.34 (bulk methylenes of fatty acid moiety), 1.50 (2H, m, F13-H), 1.58 (2H, m, 2-H), 1.62 (4H, m, F3-H₂), 1.74 (6H, s, 18-H₃), 1.89 (2H, m, 2-H), 1.96-1.98 (12H, s, 19, 20-H₃), 2.13 (2H, m, 4-H), 2.36 (4H, t, J=8 Hz, F2-H₂), 2.43 (2H, m, 4-H), 3.37 (2H, dd, J=8, 9 Hz, G2-H), 3.41 (2H, t, J=9 Hz, G4-H), 3.48 (2H, m, G5-H), 3.59 (2H, t, J=9 Hz, G3-H), 4.03 (2H, m, 3-H), 4.31 (2H, dd, J=2, 12 Hz, G6-H), 4.44 (2H, d, J=8 Hz, G1-H), 4.48 (2H, dd, J=5, 12 Hz, G6-H), 6.1-6.7 (14H, olefinic-H) (Ref. 1042)			HPLC (column: TSK gel ODS-80Ts (Tosoh) 0.4615 cm, eluent and flow: 1.0 ml/min, H2O-MeOH 5:95 for 5 min, then 5 min-linear gradient MeOH-THF 7:3) tR=12.9 min (Ref. 1041)	Thermus themophilus (thermophilic eubacterium) (Ref. 1042)				1	[1041] / [1042]
111		Chloroxanthin/ Hydroxyneurosporene/ OH-Neurosporene	1,2,7',8'-Tetrahydro-y,y-caroten-1-ol	VCA1031	Norihiko Misawa		C₄₀H₆₀O	556.904									lmax (nm): methanol 328, 412, 437, 465, %III/II=87.1 [Spectrum 1124] (Ref. 1052)						Rhodobacter, Rhodovulum, Rhodobaca, Rhodoferax, Rubrivivax and Roseobacrer species (purple photosynthetic bacteria); Rhodobacter sphaeroides Ga mutant (Ref. 1054)		This carotenoid is an intermediate in the spheroidene pathway of purple photosynthetic bacteria. The Rhodobacter sphaeroides Ga mutant also accumulates chloroxanthin (Ref. 1054). The crtD mutant of Rhodobacter sphaeroides cultured under anaerobic conditions accumulates neurosporene, chloroxanthin and methoxyneurosporene (Ref. 1089). Chloroxanthin is the substrate of CrtD of Rhodobacter sphaeoides and Rubrivivax gelatinosus in vitro. The hydrogen acceptor in this reaction is molecular oxygen (Ref. 1118/1192). An Escherichia coli transformant carrying the Erwinia uredovora crtE and crtB and Rhodobacter capsulatus crtI and crtC genes (Ref. 1065). Neurosporene is a substrate of CrtC from Rubrivivax gelatinosus and Rhodobacter capsulatus (photosynthetic bacteria) to produce chloroxanthin. Chloroxanthin is changed to dihydroxyneurosporene by CrtC from Rvi. gelatinosus, not by that from Rba. capusulatus (Ref. 1255). [Table 1018]	Escherichia coli, which carries the crtE and crtB genes from the epiphytic bacterium Erwinia uredovora, and the crtI and crtC genes from the purple photosynthetic bacterium Rhodobacter capsulatus, has produced chloroxanthin (Ref. 1065).		[1052] / [1054] / [1065] / [1089] / [1118] / [1192] / [1255]
112		Rhodopin/ OH-Lycopene	1,2-Dihydro-y,y-caroten-1-ol	VCA1032	Norihiko Misawa		C₄₀H₅₈O	554.888									lmax (nm): methanol 293, 362, 444, 470, 500, %III/II=73 (Ref. 1064) HPLC eluent 447, 474, 505, %III/II=77 [Spectrum 1125] (Ref. 1067) n-hexane 446.0, 471.0, 501.5 (Ref. 1132)		¹H-NMR (CDCl3) (Ref. 1108/1132) 1H- and 13C-NMR in CDCl3 (Ref. 1251)	FD-MS m/z: 554 (Ref. 1064/1067)(Ref. 0059)	Ramann spectrum in n-hexane (Ref. 1132)		Rhodospirillum photometricum, Rhodospirillum molischianum, Rhodospirillum fulvum, Rhodopseudomonas palustris, Rhodopseudomonas cryptolactis, Rhodomicrobium vannielii, Thiospirillum jenense, Chromatium tepidum, Thiorhodococcus minus, Ectothiorhodospira marismortui (purple photosynthetic bacteria) (Ref. 1054)		An intermediate in the normal spirilloxanthin pathway of purple photosynthetic bacteria (Ref. 1054). Rhodopin is accumulated in many purple photosynthetic bacteria due to the low activity of CrtD; Rhodospirillum photometricum, Rhodospirillum molischianum, Rhodospirillum fulvum, Rhodopseudomonas palustris, Rhodopseudomonas cryptolactis, Rhodomicrobium vannielii, Thiospirillum jenense, Chromatium tepidum, Thiorhodococcus minus, and Ectothiorhodospira marismortui (Ref. 1054). Rhodopin is the substrate of CrtD of Rubrivivax gelatinosus in vitro (Ref. 1192). Lycopene is a substrate of CrtC from Rubrivivax gelatinosus and Rhodobacter capsulatus (photosynthetic bacteria) to produce rhodopin. Rhodopin is changed to dihydroxylycopene by CrtC from Rvi. gelatinosus, not by that from Rba. capusulatus (Ref. 1255). [Table 1003]		Bond lengths, bond angles and dihedral angles determined by AM1 calculation (Ref. 1251).	[0059] / [1054] / [1064] / [1067] / [1108] / [1132] / [1192] / [1251] / [1255]
113		3,4-Dehydrorhodopin/ 3,4-Didehydrorhodopin/ 1-Hydroxy-3,4-didehydrolycopene	3,4-Didehydro-1,2-dihydro-y,y-caroten-1-ol	VCA1033	Norihiko Misawa		C₄₀H₅₆O	552.872			m.p. 194 C (Ref. 1341)						lmax (nm): methanol 305, 373, 456, 481, 513, %III/II=59 (Ref. 1064); petrol 455, 482, 517; acetone 459, 486, 520 (e 133, 195, 175 *10³) (Ref. 1341)			FD-MS m/z: 552 (Ref. 1064)			Rhodospirillum photometricum, Rhodospirillum molischianum, Rhodospirillum fulvum, Rhodopseudomonas palustris, Rhodopseudomonas cryptolactis, Rhodomicrobium vannielii, Thiospirillum jenense, Chromatium tepidum, Thiorhodococcus minus, Ectothiorhodospira marismortui (purple photosynthetic bacteria) (Ref. 1054)	(Ref. 1341)	An intermediate in the normal spirilloxanthin pathway of purple photosynthetic bacteria (Ref. 1054). [Table 1004] 3,4-Dehydrorhodopin is changed to 1,1'-(OH)₂-3,4-didehydrolycopene by CrtC from Rvi. gelatinosus, not by that from Rba. capusulatus (Ref. 1255).			[1054] / [1064] / [1255] / [1341]
114		Dihydroxylycopene/ OH-Rhodopin	1,2,1',2'-Tetrahydro-y,y-carotene-1,1'-diol	VCA1034	Norihiko Misawa		C₄₀H₆₀O₂	572.903									lmax (nm): methanol 293, 360, 443, 469, 500, %III/II=71 (Ref. 1064)			FD-MS m/z: 572 (Ref. 1064)(Ref. 0059)					Dihydroxylycopene is not the substrate of CrtD from Rubrivivax gelatinosus in vitro (Ref. 1192). an Escherichia coli transformant carrying the Erwinia uredovora crtE, crtB and crtI and Rhodobacter capsulatus crtC genes (Ref. 1064/1065). Rhodopin is changed to dihydroxylycopene by CrtC from Rvi. gelatinosus, not by that from Rba. capusulatus (Ref. 1255).	Escherichia coli, which carries the crtE, crtB and crtI genes from the epiphytic bacterium Erwinia uredovora, and the crtC gene from the purple photosynthetic bacterium Rhodobacter capsulatus, has synthesized 1,1'-dihydroxylycopene (Ref. 1064/1065).		[0059] / [1064] / [1065] / [1192] / [1255]
115		3-Hydroxy-b-zeacarotene/ 3-OH-b-Zeacarotene	(3R)-7',8'-Dihydro-b,y-caroten-3-ol	VCA1035	Norihiko Misawa		C₄₀H₅₈O	554.888																		Escherichia coli, which carries the crtE, crtB, crtY and crtZ genes from the epiphytic bacterium Erwinia uredovora, and the crtI gene from the purple photosynthetic bacterium Rhodobacter capsulatus, has synthesized 3-hydroxy-b-zeacarotene as an intermediate (Ref. 1056).		[1056]
116		1'-Hydroxy-g-carotene/ 1'-OH-g-Carotene/ (Carotenoid B)	1',2'-Dihydro-b,y-caroten-1'-ol	VCA1036	Norihiko Misawa		C₄₀H₅₈O	554.888									lmax (nm): methanol 281, 346, 436 (shoulder), 458, 487, %III/II=44.3 [Spectrum 1126] (Ref. 1052/1064/1105); hexane 433, 457, 487, %III/II=37.6 (Ref. 1108)		¹H-NMR (CDCl3) (Ref. 1108)	FD-MS m/z: 554 (Ref. 1053/1064/1103/1105/1108)			Chlorobium (present name, Chlorobaculum) tepidum strain TNO (green sulfur bacterium) (Ref. 1103) Chloroflexus aurantiacus (Ref. 1105) and Chloroflexus aggregans (S. Takaichi) (Ref. 1106) (green filamentous bacteria) Rhodococcus rhodochrous (Nocardioform actinomycetes) (Ref. 1094/1111)		Influence of growth temperature on carotenoid content and composition in Rhodococcus rhodochrous (Ref. 1109)	1'-OH-g-Carotene is produced by CrtC, carotenoid 1',2'-hydrotase, from g-Carotene in Chlorobium tepidum (green sulfur bcterium) (Ref. 1295).		[1052] / [1053] / [1064] / [1094] / [1103] / [1105] / [1106] / [1108] / [1109] / [1111] / [1295]
117		Spheroidene	1-Methoxy-3,4-didehydro-1,2,7',8'-tetrahydro-y,y-carotene	VCA1037	Norihiko Misawa	SE	C₄₁H₆₀O	568.914		Carotenoid compositions in the RC-LH1 and LH2 complexes from the anaerobic and semi-aerobic cultures of the purple photosynthetic bacterium, Rubrivivax gelatinosus (Ref. 1076)							lmax (nm): methanol 279, 344, 427, 452, 482, %III/II=78.5 [Spectrum 1127] (Ref. 1052/1100)			FD-MS m/z: 568 (Ref. 1100)	Fluorescence spectra in n-hexane and CS₂ (Ref. 1060)		Rhodobaca bogoriensis (Ref. 1100), Rhodovulum sulfidophilum (Ref. 1350), Rhodobacter, Rhodoferax, Rubrivivax and Roseobacrer species (purple phtosynthetic bacteria) (Ref. 1054)		Rhodobacter, Rhodovulum and Rhodobaca have only the spheroidene pathway, while Rubrivivax, Rhodoferax and Roseobacter have both the spheroidene and spirilloxanthin pathway (Ref. 1054). Spheroidene is one of final products in the spheroidene pathway under the anaerobic conditions of the purple photosynthetic bacteria such as Rhodobacter, Rhodovulum, Rhodobaca, Rhodoferax, Rubrivivax, and Roseobacrer species (Ref. 1054). The crtA mutant of Rhodobacter sphaeroides cultured under anaerobic conditions also accumulatates spheroidene and OH-spheroidene (Ref. 1089). The methyl residue in the methoxy group of spheroidene has been shown to originate from S-adenosylmethionine in Rhodobacter sphaeroides (Ref. 1101) and Rhodobacter capsulatus (Ref. 1102/1259). Water is a source of oxygen for the 1-methoxy group of spheroidene in Rhodobacter (Ref. 1155). Spheroidene is changed to OH-shperoidene by CrtC from Rvi. gelatinosus, not by that from Rba. capsulatus (Ref. 1255). [Table 1011]	The crt gene cluster for spheroidene biosynthesis has been cloned from Rhodobacter capsulatus, and its DNA sequence has been published in 1989 for the first time (Ref. 1032).		[1032] / [1052] / [1054] / [1060] / [1076] / [1089] / [1100] / [1101] / [1102] / [1155] / [1255] / [1259] / [1350]
118		Demethylspheroidene/ (Demethylated spheroidene)	3,4-Didehydro-1,2,7',8'-tetrahydro-y,y-caroten-1-ol	VCA1038	Norihiko Misawa	DMS	C₄₀H₅₈O	554.888									lmax (nm): methanol 279, 345, 427, 452, 482, %III/II=75 [Spectrum 1128] (Ref. 1064/1100)			FD-MS m/z: 554 (Ref. 1064/1260)			Rhodobaca bogoriensis (Ref. 1100), Rhodovulum sulfidophilum (Ref. 1350), Rhodobacter, Rhodoferax, Rubrivivax and Roseobacrer species (purple photosynthetic bacteria) (Ref. 1054)		An intermediate in the spheroidene pathway of purple photosynthetic bacteria (Ref. 1054). Demethylspheroidene is changed to OH-demethylshperoidene by CrtC from Rvi. gelatinosus, not by that from Rba. capusulatus (Ref. 1255). [Table 1012]	Escherichia coli, which carries the crtE and crtB genes from the epiphytic bacterium Erwinia uredovora, the crtI and crtC genes from the purple photosynthetic bacterium Rhodobacter capsulatus and the crtD gene from Rhodobacter sphaeroides, has synthesized demethylspheroidene (Ref. 1065). The crtF mutant of Rhodobacter capsulatus accumulats DMS and DMSO (Ref. 1102). The crtA and crtF mutant of Rubrivivax gelatinosus (photosynthetic bacteria) produces this carotenoid (Ref. 1260).		[1054] / [1064] / [1065] / [1100] / [1102] / [1255] / [1260] / [1350]
119		Spheroidenone	1-Methoxy-3,4-didehydro-1,2,7',8'-tetrahydro-y,y-caroten-2-one	VCA1039	Norihiko Misawa	SO	C₄₁H₅₈O₂	582.898		Carotenoid compositions in the RC-LH1 and LH2 complexes from the anaerobic and semi-aerobic cultures of the purple photosynthetic bacterium, Rubrivivax gelatinosus (Ref. 1076). In the reaction center of Rhodobacter sphaeroides, conformation of spheroidenone is 15-cis form from the X-ray crystal structure (Ref. 1139).							lmax (nm): hexane 482, 513; benzene 499, 532 (shoulder) (Ref. 1073); methanol 298, 377, 483 [Spectrum 1129] (Ref. 1075/1100), reduced form 297, 345, 428, 452, 482 %III/II=67 [Spectrum 1129] (Ref. 1100)		¹H-NMR (CDCl₃): 1.34 s (16, 17-H₃), 1.59 s (16'-H₃), 1.60 s (18'-H₃), 1.67 s (17'-H₃), 1.81 s (19'-H₃), 1.95 s (20'-H₃), 1.96 s (20-H₃), 1.99 s (18, 19-H₃), 2.04 (3'-H₂), 2.12 (4', 7', 8'-H₂), 3.21 s (1-O-CH₃), 5.08 t (J=7 Hz; 2'-H), 5.11 t (J=8 Hz; 6'-H), 5.95 d (J=11 Hz; 10'-H), 6.75 d (J=16 Hz; 3-H), 7.46 d (J=16 Hz; 4-H) (Ref. 1075)	FD-MS m/z: 582 (Ref. 1075/1100)(Ref. 0059)		Silicagel G TLC, benzene-acetone (20:3): Rf=0.57 (Ref. 1073)	Rhodobaca bogoriensis (Ref. 1100), Rhodovulum sulfidophilum (Ref. 1350), Rhodobacter, Rhodoferax, Rubrivivax and Roseobacrer species (the purple photosynthetic bacteria) (under semi-aerobic culture) (Ref. 1054) Major carotneoid of Roseobacter denitrificans (=Erythrobacter sp. OCh 114) (Ref. 1073) and Dinoroseobacter shibae (Ref. 1348) (aerobic photosynthetic bacterium)		Rhodobacter, Rhodovulum and Rhodobaca have only the spheroidene pathway, while Rubrivivax, Rhodoferax and Roseobacter have both the spheroidene and spirilloxanthin pathway (Ref. 1054). Spheroidenone is one of final products in the spheroidene pathway under semi-aerobic culture of purple photosynthetic bacteria such as Rhodobacter, Rhodovulum, Rhodobaca, Rhodoferax, Rubrivivax and Roseobacrer species. (Ref. 1054). The methyl residue in the methoxy group of spheroidenone is originated from S-adenosylmethionine in Rhodobacter sphaeroides (Ref. 1101). Water is a source of oxygen for the 1-methoxy group of spheroidenone in Rhodobacter, but water and CO₂ are not that for the 2-oxo group (Ref. 1155). [Table 1013]		The keto group at C-2 of spheroidenone is single bond cis-fonformation for the conjugated double bond determined by NMR (Ref. 1075).	[0059] / [1054] / [1073] / [1075] / [1076] / [1100] / [1101] / [1139] / [1155] / [1348] / [1350]
120		Spirilloxanthin	1,1'-Dimethoxy-3,4,3',4'-tetradehydro-1,2,1',2'-tetrahydro-y,y-carotene	VCA1040	Norihiko Misawa		C₄₂H₆₀O₂	596.925		Carotenoid compositions in the RC-LH1 and LH2 complexes from the anaerobic and semi-aerobic cultures of Rubrivivax gelatinosus (purple photosynthetic bacterium) (Ref. 1076). 15-Cis form is bound to the reaction center complex, and all-trans one is bound to the light-harvesting complex of Rhodospirillum rubrum S1 (purple photosynthetic bacterium) (Ref. 1120).	m.p. 219.5-220 C (Ref. 1341)						lmax (nm): methanol 315, 385, 464, 492, 524, %III/II=63.8 [Spectrum 1130] (Ref. 1052/1055); HPLC eluent 469, 498, 531, %III/II=64 (Ref. 1067); n-hexane (all-trans) 365, 386, 463, 492, 526; n-hexane (13-cis) 368, 386, 460, 488, 520; n-hexane (15-cis) 367, 385, 462, 490, 524 (Ref. 1120); n-hexane 464.0, 492.5, 527.0 (Ref. 1132); HPLC eluent (hexane/ethylisopropylamine/acetone 98.5/0.05/1.5) (all-E) 388, 466, 494, 528, %III/II=73, %D_B/D_I_I=8; (13Z; 5Z,13'Z; 5Z,13Z; 5Z,9'Z; 9Z; 5Z,9Z; 5Z) (Ref. 1181); benzene 480, 510, 546 (e 118, 169, 146 *10³) (Ref. 1341)	(Ref. 1341)	¹H-NMR (CDCl3): 1.16 s (16, 17-H₃), 1.93 s (18-H₃), 1.98 s (19-H₃), 1.99 s (20-H₃), 2.32 d (J=7.3 Hz; 2-H₂), 3.23 s (1-O-CH₃) (Ref. 1071); (CDCl3) (Ref. 1132); (CDCl3) all-E, 5Z, 9Z (Ref. 1181) 1H- and 13C-NMR in CDCl3 (Ref. 1251)	FD-MS m/z: 596 (Ref. 1053/1055/1067)(Ref. 0059)	Ramann spectrum in n-hexane (Ref. 1132)	All-E and some Z isomers produced by the iodine-catalyzed stereo mutation mixture are separated by preparative HPLC (Chromosphere SI-5, 250 X 10 mm) (Ref. 1181).	Rhodospirillum rubrum, Rhodovibrio (=Rhodospirillum) sodomense, Rhodopseudomonas julia, Thiocapsa (=Amoebobacter) roseus, Thiocapsa roseopersicina, Halorhodospira halophila (purple phtosynthetic bacteria) (Ref. 1054) Erythrobacter longus (aerobic photosynthetic bacterium) (Ref. 1055) Bradyrhizobium sp. strains (aerobic photosynthetic bacteria) (Ref. 1156)	(Ref. 1341)	Spirilloxanthin is the end product of the normal spirilloxanthin pathway, and more than half species of the purple photosynthetic bacteria have spirilloxanthin as major carotenoid. These bacterial species are Rhodospirillum rubrum, Rhodovibrio (=Rhodospirillum) sodomense, Rhodopseudomonas julia, Thiocapsa (=Amoebobacter) roseus, Thiocapsa roseopersicina, and Halorhodospira halophila (Ref. 1054). [Table 1008]	Two distinct crt gene clusters for spirilloxanthin (crtE.s, crtB.s, crtI.s, crtC, crtD and crtF) and canthaxanthin (crtE.c, crtB.c, crtI.c, crtY and crtW) synthesis are isolated from Bradyrhizobium sp. strain ORS278 (aerobic photosynthetic bacterium) and functionaly identified (Ref. 1121/1284).	Bond lengths, bond angles and dihedral angles determined by AM1 calculation (Ref. 1251).	[0059] / [1052] / [1053] / [1054] / [1055] / [1067] / [1071] / [1076] / [1120] / [1121] / [1132] / [1156] / [1181] / [1251] / [1284] / [1341]
121		b-Isorenieratene	b,f-Carotene	VCA1041	Norihiko Misawa		C₄₀H₅₂	532.841														HPLC (column; Novapak C18 (Waters) 8 X 100 mm: eluelnt; acetonitrile/methanol/THF 58:35:7: flow 2.0 ml/min) Rt=12.0 min (Ref. 1057)	Chlorobium phaeobacteroides 1549 (new name, Chlorobaculum limnaeum 1549; green-sulfur photosynthetic bacterium), the content of this carotenoid incleases under low light culture (Ref. 1282).		b-Isorenieratene is the biosynthetic intermediate through desaturation reactions from b-carotene to isorenieratene (Ref. 1093).			[1057] / [1093] / [1282]
122		Isorenieratene/ (Leprotene)	f,f-Carotene	VCA1042	Norihiko Misawa		C₄₀H₄₈	528.809			198-199 C (Ref. 1332)						lmax (nm): acetonitrile/methanol/THF (58:35:7) 283, 352, 431 (shoulder), 452, 472, %III/II=26 [Spectrum 1013] (Ref. 1057); benzene 443, 465, 493 (Ref. 1316); petroleum ether (425), 450, 477 (Ref. 1332)	(Ref. 1332)	(Ref. 1316/1332)	(Ref. 1332)		HPLC (column; Novapak C18 (Waters) 8 X 100 mm: eluelnt; acetonitrile/methanol/THF 58:35:7: flow 2.0 ml/min) Rt=8.2 min (Ref. 1057)	Streptomyces griseus (actinomycetes) (Ref. 1093), Brevibacterium linens (Gram-positive coryneform bacterium) (Ref. 1134). Chlorobium phaeobacteroides 1549 (new name, Chlorobaculum limnaeum 1549; green-sulfur photosynthetic bacterium), the content of this carotenoid incleases under low light culture (Ref. 1282). Reniera japonica (sea sponge) (Ref. 1331). Suberites sericeus (sea sponge) contains isorenieratene, isorenieracistene (7-cis isorenieratene) and isorenieradicistene (7,7'-dicis isorenieratene) (Ref. 1332).	(Ref. 1316/1331)		Genes involved in the synthesis of isorenieratene have been clone from Streptomyces griseus (Ref. 1093), Brevibacterium linens (Ref. 1124) and Mycobacterium aurum (Ref. 1127). CrtU synthesises isorenieratene from b-carotene (Ref. 1093/1124/1127).		[1057] / [1093] / [1124] / [1127] / [1134] / [1282] / [1316] / [1331] / [1332]
123		d-Carotene/ e,y-Carotene	(6R)-e,y-Carotene	VCA1043	Norihiko Misawa		C₄₀H₅₆	536.873																	[Table 1034]	Lycopene e-cyclase CrtL-e from plants, such as, Arabidopsis, tomato, potato and marigold, adds only one ring to lycopene, forming the monocyclic d-carotene, but can not add a second ring to form e-carotene. When combined, lycopene b- and e-cyclases convert lycopene to a-carotene, a carotenoid with one b and one e ring (Ref. 1015/1239). Exceptionally, lycopene e-cyclase from lettuce produces e-carotene (Ref. 1148). Lycopene e- and b-cyclases, neoxanthin synthase (NSY) and capsanthin-capsorubin synthase (CCS) have high homology (Ref. 1015/1148/1239). CrtL-e from the marine cyanobacterium Prochlorococcus marinus MED4 has bifunctional activety; lycopene e- and b-cyclases (Ref. 1242).		[1015] / [1148] / [1239] / [1242]
124		e-Carotene/ e,e-Carotene	(6R,6'R)-e,e-Carotene	VCA1044	Norihiko Misawa		C₄₀H₅₆	536.873									lmax (nm): acetonitrile/methanol/THF (58:35:7) 266, 329, 417, 441, 470, %III/II=89 [Spectrum 1014] (Ref. 1057)					HPLC (column; Novapak C18 (Waters) 8 X 100 mm: eluelnt; acetonitrile/methanol/THF 58:35:7: flow 2.0 ml/min) Rt=16.2 min (Ref. 1057)				Usually the substrate of lycopen e-cyclase from plants is only lycopene, and d-carotene and g-carotene are not, while lycopene e-cyclase from Lactuca sativa (romaine lettuce) can cyclize d-carotene to form e-carotene and the final product is lactucaxanthin (tunaxanthin F). A single amino acid is found to act as a molecular switch: one e-ring or two (Ref. 1148).		[1057] / [1148]
125		Bisdehydrolycopene/ Tetradehydrolycopene	3,4,3',4'-Tetradehydro-y,y-carotene	VCA1045	Norihiko Misawa		C₄₀H₅₂	532.841									lmax (nm): HPLC eluent 480, 510, 540 (Ref. 1049)			(Ref. 0059)					an Escherichia coli transformant carrying the Erwinia uredovora crtE and crtB genes, and the crtI gene (crtI14) shuffled between the corresponding genes of E. uredovora and E. herbicola (Ref. 1049)	A special phytoene desaturase gene (crtI14), which has been shuffled between the crtI genes of Erwinia uredovora and E. herbicola, has mediated the synthesis of bisdehydrolycopene that is a six-step-desaturation product from phytoene (Ref. 1049).		[0059] / [1049]
126		Rubixanthin/ 3-Hydroxy-g-carotene/ 3-OH-g-Carotene	(3R)-b,y-Caroten-3-ol	VCA1046	Norihiko Misawa		C₄₀H₅₆O	552.872									lmax (nm): methanol 282, 346, 436 (shoulder), 458, 489, %III/II=48.1 [Spectrum 1131] (Ref. 1052/1055)			FD-MS m/z: 552 (Ref. 1055)(Ref. 0059)			Erythrobacter longus (aerobic photosynthetic bacterium) (Ref. 1055)					[0059] / [1052] / [1055]
127		Asymmetric z-carotene/ Asym. z-carotene/ 7,8,11,12-Tetrahydrolycopene	7,8,11,12-Tetrahydro-y,y-carotene	VCA1047	Norihiko Misawa		C₄₀H₆₀	540.904									lmax (nm): acetonitrile/methanol/THF (58:35:7) 238, 298, 377, 397, 421, %III/II=89 [Spectrum 1006] (Ref. 1057); methanol 295, 374, 395, 419, %III/II=89.9 [Spectrum 1115] (Ref. 1052)					HPLC (column; Novapak C18 (Waters) 8 X 100 mm: eluelnt; acetonitrile/methanol/THF 58:35:7: flow 2.0 ml/min) Rt=16.8 min (Ref. 1057)	Rhdospirillum rubrum, Rhodopila glabiformis, Rhodomicrobium vannielii, Blastochloris viridis (Purple photosynthetic bacteria). Chlorobium tepidum (Green sulfur photosynthetic bacteria). Chloroflexus aurantiacus (Green filamentous photosynthetic bacteria) (Ref. 1054). Erythrobacter longus (aerobic photosynthetic bacteria) (Ref. 1055)		[Table 1024]			[1052] / [1054] / [1055] / [1057]
128		Rhodopin glucoside/ Rhodopin b-D-glucoside	1-b-D-Glucopyranosyloxy-1,2-dihydro-y,y-carotene	VCA1048	Norihiko Misawa		C₄₆H₆₈O₆	717.029		One component of the light-harvesting antenna comples (LH2, B800-850) from the purple photosynthetic bacterium, Rhodopseudomonas acidophilla strain 10050; 9 X (one rhodopin glucoside, one B800 BChl, two B850 BChl, one a-polypeptide and one b-polypeptide) (Ref. 1059). Van der Waals contacts of rhodopin glucoside with bacteriochlorophyll (B800) are studied, and the hydrogen positions are determined from quantum chemical calculations at the Hartree-Fock level (Ref. 1232). Apoprotein contacts to the rhodopin glucoside chromophore (Ref. 1304).										FD-MS: 716 (S. Takaichi)			Rhodopseudomonas acidophilla strain 10050 (present name: Rhodoblastus acidophilus; purple photosynthetic bacterium) (Ref. 1059/1304) Strain 10050: high light culture (160 mmols/s/m²), rhodopin glucoside 80%; strain 7050: high light culture, rhodopin glucoside 34%, low light culture (10 mmols/s/m²), rhodopinal 5%, rhodopin goucoside 1%, rhodopinol glucoside 7% and rhodopinal glucoside 61%; strain 7750: high light culture, rhodopin glucoside 53%, low light culture, rhodopin goucoside 24% (Ref. 1054).				Glycoside moiety is b-D-glucoside by 1H-NMR (S. Takaichi).	[1054] / [1059] / [1232] / [1304]
129		4,4'-Diapophytoene/ Dehydrosqualene	7,8,11,12,7',8',11',12'-Octahydro-4,4'-diapo-y,y-carotene	VCA1049	Norihiko Misawa		C₃₀H₄₈	408.702									lmax (nm): acetonitrile/methanol/THF (58:35:7) 277 (shoulder), 287, 296 (shoulder) [Spectrum 1015] (Ref. 1057/1069); petroleum 275, 286 (Ref. 1364/1368), 297; ethanol (277), 286, 298 (Ref. 1364)			FD-MS m/z: 408 (Ref. 1069); (Ref. 1368)		HPLC (column; Novapak C18 (Waters) 8 X 100 mm: eluelnt; acetonitrile/methanol/THF 58:35:7: flow 2.0 ml/min) Rt=10.0 min (Ref. 1057/1069)	Heliobacillus mobilis, Heliophilum fasciatum, Hebacterium chlorum, Heliobacteirum modesticaldum (Heliobacteria) (Ref. 1069) Streptococcus faecium UNH 564P 43% of total) (Ref. 1363/1368) Staphylococcus aureus 209P (75% of total) (Ref. 1364)		The symmetrical carbon skeleton is reduced from biosynthetic labelling studies in Streptococcus faecium UNH 564P (Ref. 1363/1369).	A 4,4'-diapophytoene synthase gene (crtM), which mediates the synthetic reaction from farnesyl diphosphate (FPP) to 4,4'-diapophytoene (dehydrosqualene), has been cloned from Staphylococcus aureus (Ref. 1092). The gene diapophytoene desaturase crtN is found from Heliobacillus mobilis based on the sequence similarity. (Ref. 1070)		[1057] / [1069] / [1070] / [1092] / [1363] / [1364] / [1368] / [1369]
130		4,4'-Diaponeurosporene	7,8-Dihydro-4,4'-diapo-y,y-carotene	VCA1050	Norihiko Misawa		C₃₀H₄₂	402.654									lmax (nm): acetonitrile/methanol/THF (58:35:7) 267, 331, 416, 439, 468, %III/II=95 [Spectrum 1016] (Ref. 1057/1069); HPLC eluent 416, 438, 468 (Ref. 1117); methanol [Spectrum 1132] ; petroleum (390), 412, 436, 466; ethanol (391), 414, 438, 467.5 (Ref. 1364); petroleum (390), 412, 435, 465 (Ref. 1368)			FD-MS m/z: 402 (Ref. 1069); LC/MS m/z: 403 [M+H]⁺ (Ref. 1117); (Ref. 1368)		HPLC (column; Novapak C18 (Waters) 8 X 100 mm: eluelnt; acetonitrile/methanol/THF 58:35:7: flow 2.0 ml/min) Rt=5.9 min (Ref. 1057/1069)	Major carotenoid of Heliobacillus mobilis, Heliophilum fasciatum, Hebacterium chlorum, Heliobacteirum modesticaldum, Heliobacterium gestii (heliobacteria) (Ref. 1069); and alkaliphilic heliobacteria, Heliorestis daurensis and Heliorestis baculata, produces 4,4'-diaponeurosporen and OH-diaponeurosporene glucoside esters (Ref. 1270). Staphylococcus aureus Newman (Ref. 1092), Staphylococcus aureus 209P (1% of total) (Ref. 1364), Streptococcus faecium UNH 564P (13% of total) (Ref. 1363), and Staphylococcus carnosus, Lactobacillus plantarum, Enterococcus mundtii, Enterococcus sulfureus (Ref. 1117).		Characteristics of CrtN from Staphylococcus aureus; membrane protein, 52 kDa single peptide, substrate specificity, FAD-dependent and diphenylamine inhibition (Ref. 1128/1129). An Escherichia coli transformant carrying the S. aureus crtM and crtN genes produces 4,4'-diaponeurosporene (Ref. 1092/1215). The symmetrical carbon skeleton is reduced from biosynthetic labelling studies in Streptococcus faecium UNH 564P (Ref. 1363/1369).	A 4,4'-diapophytoene desaturase gene (crtN), which mediates the desaturation reactions from 4,4'-diapophytoene (dehydrosqualene) to 4,4'-diaponeurosporene, has been cloned from Staphylococcus aureus (Ref. 1092). Another crtN gene has also been found in Heliobacillus mobilis based on the sequence similarity (Ref. 1070).		[1057] / [1069] / [1070] / [1092] / [1117] / [1128] / [1129] / [1215] / [1270] / [1363] / [1364] / [1368] / [1369]
131		h-Carotene/ Tetrahydro-b-carotene	7,8,7',8'-Tetrahydro-b,b-carotene	VCA1051	Shinichi Takaichi		C₄₀H₆₀	540.904									lmax (nm): acetonitrile/methanol/THF (58:35:7) 234, 293, 381, 402, 427, %III/II=103 [Spectrum 1017] (Ref. 1056/1057)		¹H-NMR (CDCl₃): 1.01 s (16, 17-H₃), 1.61 s (18-H₃), 1.83 s (19-H₃), 1.93 s (20-H₃) (Ref. 1056/1063)	FD-MS m/z: 540 (Ref. 1056)		HPLC (column; Novapak C18 (Waters) 8 X 100 mm: eluelnt; acetonitrile/methanol/THF 58:35:7: flow 2.0 ml/min) Rt=31.3 min (Ref. 1056/1057)				When lycopene cyclase from Erwinia uredovara (crtY) was expressed in Escherichia coli with a %z-carotene background, this carotenoid was produced. The substrate of crtY is not only y end group but 7,8-dihydro-y end group. (Ref. 1056)		[1056] / [1057] / [1063]
132		Caloxanthin	(2R,3R,3'R)-b,b-Carotene-2,3,3'-triol	VCA1052	Shinichi Takaichi		C₄₀H₅₆O₃	584.871									lmax (nm): methanol 273, 339, 427 (shoulder), 448, 475, %III/II=31.6 [Spectrum 1133] (Ref. 1052/1055); acetone 430 (shoulder), 453.5, 480.5 (Ref. 1077)	n^K^B^r_m_a_x cm^-¹: 3400 m, 3030 w, 2960 s, 2930 s, 2860 s, 1465 m, 1440 m, 1380 w, 1180 w, 1120 m, 1075 w, 1055 m, 970 m (Ref. 1077)	¹H-NMR (CDCl₃): 1.00 s (16-H₃), 1.07 s (16', 17'-H₃), 1.13 s (17-H₃), 1.38 d (3'-OH), 1.48 dd (2'-Hax), 1.72 s (18-H₃), 1.74 s (18'-H₃), ca. 1.77 (2'-Heq), 1.97 s (19, 20, 19', 20'-H₃), 2.05 dd (4-Hax), ca. 2.20 (4'-Hax), 2.39 dd (4'-Heq), 2.48 dd (4-Heq), 3.33 d (J=10.1 Hz; 2-Hax), 3.84 m (3-Hax), 4.00 m (3'-Hax) (Ref. 1055); CDCl₃ (Ref. 1344)	FD-MS m/z: 584 (Ref. 1055)	CD spectrum is the same with that of (3R,3'R)-zeaxanthin (Ref. 1055) CD l nm (de) diethyl ether/isopentane/ethanol (5:5:2): 337 (+ 4.6), 312 (0), 283 (- 16), 260 (0), 244 (+ 8.8), 231 (0), 222 (- 10.4), 212 (0) (Ref. 1077)		Porphyrobacter, Erythrobacter, and Erythromicrobium based on TLC (aerobic photosynthetic bacteria) (Ref. 1237) Erythrobacter longus (aerobic photosynthetic bacterium) (Ref. 1055)			Reaction products of Brevundimonas crtG expessed in E.coli with zeaxanthin background (crtE, crtB, crtI, crtY and crtZ from Pantoea) (Ref. 1344)		[1052] / [1055] / [1077] / [1237] / [1344]
133		Anhydrorhodovibrin	1-Methoxy-3,4-didehydro-1,2-dihydro-y,y-carotene	VCA1053	Shinichi Takaichi	AHRV	C₄₁H₅₈O	566.899									lmax (nm): methanol 304, 372, 454, 480, 513, %III/II=65.2 [Spectrum 1134] (Ref. 1052/1055); n-hexane 453.5, 481.5, 514.5 (Ref. 1132)		¹H-NMR (CDCl3) (Ref. 1132) 1H- and 13C-NMR in CDCl3 (Ref. 1251)	FD-MS m/z: 566 (Ref. 1055)(Ref. 0059)	Ramann spectrum in n-hexane (Ref. 1132)		Purple photosynthetic bacteria. (Ref. 1054) Erythrobacter longus (aerobic photosynthetic bacterium) (Ref. 1055)		An intermediate in the normal spirilloxanthin pathway of purple photosynthetic bacteria (Ref. 1054/1055). [Table 1005]		Bond lengths, bond angles and dihedral angles determined by AM1 calculation (Ref. 1251).	[0059] / [1052] / [1054] / [1055] / [1132] / [1251]
134		Rhodovibrin	1'-Methoxy-3',4'-didehydro-1,2,1',2'-tetrahydro-y,y-caroten-1-ol	VCA1054	Shinichi Takaichi	RV	C₄₁H₆₀O₂	584.914									lmax (nm): methanol 304, 372, 479, 496, 511, %III/II=45 [Spectrum 1135]; n-hexane 454.0, 481.5, 514.5 (Ref. 1132)		¹H-NMR (CDCl3) (Ref. 1132) 1H- and 13C-NMR in CDCl3 (Ref. 1251)	(Ref. 0059)	Ramann spectrum in n-hexane (Ref. 1132)		Purple photosynthetic bacteria. (Ref. 1054)		An intermediate in the normal spirilloxanthin pathway of purple photosynthetic bacteria (Ref. 1054). [Table 1006]		Bond lengths, bond angles and dihedral angles determined by AM1 calculation (Ref. 1251).	[0059] / [1054] / [1132] / [1251]
135		Monodemetyl spirilloxanthin/ Hydroxyspirilloxanthin/ OH-Spirilloxanthin	1'-Methoxy-3,4,3',4'-tetradehydro-1,2,1',2'-tetrahydro-y,y-caroten-1-ol	VCA1055	Shinichi Takaichi		C₄₁H₅₈O₂	582.898			m.p. 214-214.5 C (Ref. 1341)						lmax (nm): acetone 469, 498, 531 (e 128, 184, 161 *10³) (Ref. 1341)			(Ref. 0059)			Purple photosynthetic bacteria. (Ref. 1054)	(Ref. 1341)	An intermediate in the normal spirilloxanthin pathway of purple photosynthetic bacteria (Ref. 1054). [Table 1007]			[0059] / [1054] / [1341]
136		3,4-Dihydroanhydrorhodovibrin	1-Methoxy-1,2-dihydro-y,y-carotene	VCA1056	Shinichi Takaichi		C₄₁H₆₀O	568.914									lmax (nm): HPLC eluent 447, 474, 505, %III/II=74 (Ref. 1067)		¹H-NMR (benzene): 1.06 (16, 17-H₃), 1.41 (2-H₂), 1.57 (17'-H₃), 1.58 (3-H₂), 1.68 (16'-H₃), 1.75 (18'-H₃), 1.76 (18-H₃), 1.88 (20, 20'-H₃), 1.93 (19'-H₃), 1.94 (19-H₃), 2.09 (4-H₂), 2.19 (3', 4'-H₂), 3.04 (1-O-CH₃), 6.18 (6'-H), 6.20 (6-H) (Ref. 1067)	FD-MS m/z: 568 (Ref. 1067)			Rhodospirillum rubrum ST4 mutant (purple photosynthetic bacterium) (Ref. 1067)		This carotenoid seems to be by-product in the normal spirilloxanthin pathway of purple photosynthetic bacteria (Ref. 1054). In Rhodospirillum rubrum ST4 mutant, crtD may be mutated, but 7,8-dihydro-y end group can unusually be the substrate of CrtF (Ref. 1067).	In Rhodospirillum rubrum ST4 mutant, crtD may be mutated, but 7,8-dihydro-y end group can unusually be the substrate of CrtF. (Ref. 1067)		[1054] / [1067]
137		3',4'-Dihydrorhodovibrin	1'-Methoxy-1,21',2'-tetrahydro-y,y-caroten-1-ol	VCA1057	Shinichi Takaichi		C₄₁H₆₂O₂	586.930									lmax (nm): HPLC eluent 447, 474, 505, %III/II=76 [Spectrum 1136] (Ref. 1067)		¹H-NMR (benzene): 0.59 (1-OH), 1.03 (16, 17-H₃), 1.06 (16', 17'-H₃), 1.32 (2-H₂), 1.41 (2'-H₂), 1.49 (3-H₂), 1.58 (3'-H₂), 1.75 (18-H₃), 1.76 (18'-H₃), 1.88 (20, 20'-H₃), 1.95 (19-H₃), 1.94 (19'-H₃), 2.06 (4-H₂), 2.09 (4'-H₂), 3.04 (1-O-CH₃), 6.18 (6-H), 6.19 (6'-H) (Ref. 1067)	FD-MS m/z: 586 (Ref. 1067)			Rhodospirillum rubrum ST4 mutant (purple photosynthetic bacterium) (Ref. 1067)		In Rhodospirillum rubrum ST4 mutant, crtD may be mutated, but 7,8-dihydro-y end group can unusually be the substrate of CrtF. (Ref. 1067)	In Rhodospirillum rubrum ST4 mutant, crtD may be mutated, but 7,8-dihydro-y end group can unusually be the substrate of CrtF. (Ref. 1067)		[1067]
138		3,4,3',4'-Tetrahydrospirilloxanthin	1,1'-Dimethoxy-1,2,1',2'-tetrahydro-y,y-carotene	VCA1058	Shinichi Takaichi		C₄₂H₆₄O₂	600.956									lmax (nm): HPLC eluent 447, 474, 505, %III/II=75 [Spectrum 1137] (Ref. 1067)		¹H-NMR (benzene): 1.06 (16, 17-H₃), 1.41 (2-H₂), 1.58 (3-H₂), 1.76 (18-H₃), 1.88 (20-H₃), 1.94 (19-H₃), 2.09 (4-H₂), 3.04 (1-O-CH₃), 6.19 (6-H) (Ref. 1067)	FD-MS m/z: 600 (Ref. 1067/1068)(Ref. 0059)			Rhodospirillum rubrum ST4 mutant (Ref. 1067), Rhodospira trueperi, Thioalkalicoccus limnaeus, Thioflavicoccus mobilis, Halorhodospira abdelmalekii, Halorhodospira halochloris (purple photosynthetic bacteria) (Ref. 1054/1068), a major carotenoid of Thiococcus (=Thiocapsa) pfennigii (Ref. 1319).		The final product in the unusual spirilloxanthin pathway of purple photosynthetic bacteria (no activity of CrtD or crtD mutant) (Ref. 1054). In Rhodospirillum rubrum ST4 mutant, crtD may be mutated, but 7,8-dihydro-y end group can unusually be the substrate of CrtF. (Ref. 1067)	In Rhodospirillum rubrum ST4 mutant, crtD mutant may be mutated, but 7,8-dihydro-y end group can unusually be the substrate of CrtF. (Ref. 1067)		[0059] / [1054] / [1067] / [1068] / [1319]
139		4,4'-Diapophytofluene	7,8,11,12,7',8'-Hexahydro-4,4'-diapo-y,y-carotene	VCA1059	Shinichi Takaichi		C₃₀H₄₆	406.686									lmax (nm): acetonitrile/methanol/THF (58:35:7) 255, 333, 349, 368 %III/II=83 [Spectrum 1018] (Ref. 1057/1069); petroleum (316), 330, 347, 366 (Ref. 1364/1368); ethanol (316), 331, 345, 367 (Ref. 1364)			FD-MS m/z: 406 (Ref. 1069); (Ref. 1368)		HPLC (column; Novapak C18 (Waters) 8 X 100 mm: eluelnt; acetonitrile/methanol/THF 58:35:7: flow 2.0 ml/min) Rt=7.6 min (Ref. 1057/1069)	Heliobacillus mobilis, Heliophilum fasciatum, Heliobacterium gestii (Heliobacteria) (Ref. 1069) Staphylococcus aureus Newman (Ref. 1092), Staphylococcus aureus 209P (2% of total) (Ref. 1364), Streptococcus faecium UNH 564P (12% of total) (Ref. 1363)		an Escherichia coli transformant carrying the S. aureus crtM gene (Ref. 1092). The symmetrical carbon skeleton is reduced from biosynthetic labelling studies in Streptococcus faecium UNH 564P (Ref. 1363/1369).	A 4,4'-diapophytoene (dehydrosqualene) synthase gene (crtM), which mediates synthesis of 4,4'-diapophytoene (dehydrosqualene) from farnesyl diphosphate, has been cloned from Staphylococcus aureus (Ref. 1092).		[1057] / [1069] / [1092] / [1363] / [1364] / [1368] / [1369]
140		4,4'-Diapo-z-carotene	7,8,7',8'-Tetrahydro-4,4'-diapo-y,y-carotene	VCA1060	Shinichi Takaichi		C₃₀H₄₄	404.670									lmax (nm): acetonitrile/methanol/THF (58:35:7) 234, 295, 380, 401, 426 %III/II=94 [Spectrum 1019] (Ref. 1057/1069); petroleum (358), 378, 400, 425 (Ref. 1364/1368); ethanol (360), 379, 401, 426 (Ref. 1364)			FD-MS m/z: 404 (Ref. 1069); (Ref. 1368)		HPLC (column; Novapak C18 (Waters) 8 X 100 mm: eluelnt; acetonitrile/methanol/THF 58:35:7: flow 2.0 ml/min) Rt=6.5 min (Ref. 1057/1069)	Heliobacillus mobilis, Heliophilum fasciatum, Heliobacterium gestii (Heliobacteria) (Ref. 1069) Streptococcus faecium UNH 564P (4% of total) (Ref. 1363/1368), Staphylococcus aureus 209P (2% of total) (Ref. 1364).		The symmetrical carbon skeleton is reduced from biosynthetic labelling studies in Streptococcus faecium UNH 564P (Ref. 1363/1369).			[1057] / [1069] / [1363] / [1364] / [1368] / [1369]
141		4,4'-Diapolycopene	4,4'-Diapo-y,y-carotene	VCA1061	Shinichi Takaichi		C₃₀H₄₀	400.639									lmax (nm): acetonitrile/methanol/THF (58:35:7) 294, 361, 445, 470, 501 %III/II=67 [Spectrum 1020] (Ref. 1057/1069); ethanol 440, 467, 498 (Ref. 1366)			FD-MS m/z: 400 (Ref. 1069); MS (Ref. 1366)		HPLC (column; Novapak C18 (Waters) 8 X 100 mm: eluelnt; acetonitrile/methanol/THF 58:35:7: flow 2.0 ml/min) Rt=5.4 min (Ref. 1057/1069)	Heliobacteria: Heliobacillus mobilis, Heliophilum fasciatum, Heliobacteirum modesticaldum, Heliobacterium gestii (Ref. 1069) Methylobacterium rhodinum (formerly Pseudomonas rhodos) (Ref. 1366)		an Escherichia coli transformant carrying the Staphylococcus aureus crtM and Erwinia uredovora crtE and crtI genes (Ref. 1215)			[1057] / [1069] / [1215] / [1366]
142		Bacteriorubuxanthin	(3R)-1'-Methoxy-3',4'-didehydro-1',2'-dihydro-b,y-caroten-3-ol	VCA1062	Shinichi Takaichi		C₄₁H₅₈O₂	582.898									lmax (nm): methanol 293, 361, 446 (shoulder), 468, 499, %III/II=46.2 [Spectrum 1138] (Ref. 1052/1071)		¹H-NMR (CDCl₃): 1.07 s (16, 17-H₃), 1.16 s (16', 17'-H₃), 1.36 d (J=4.8 Hz; 3-OH), 1.48 t (2-Hax), 1.74 s (18-H₃), 1.78 m (2-Heq), 1.93 s (18'-H₃), 1.97 s (19, 19'-H₃), 1.98 s (20, 20'-H₃), 2.05 m (4-Hax), 2.34 d (J=7.3 hZ; 2'-H₂), 2.39 dd (4-Heq), 3.23 s (1'-O-CH₃), 3.99 m (3-Hax) (Ref. 1071)	FD-MS m/z: 582 (Ref. 1071)	CD (Ref. 1071)		Erythrobacter longus (aerobic photosynthetic bacterium) (Ref. 1071)					[1052] / [1071]
143		Bacteriorubixanthinal	(3R)-9'-cis-3-Hydroxy-1'-methoxy-3',4'-didehydro-1',2'-dihydro-b,y-caroten-19'-al	VCA1063	Shinichi Takaichi		C₄₁H₅₆O₃	596.882		Bacteriorubixanthinal and zeaxanthin are major carotenoids in the RC-B865 pigment-protein complex of Erythrobacter longus, and have a high efficiency of energy transfer to bactriochlorophyll. Resonance Raman spectra of these two carotenoids show some characteristics of interactions with proteins or bacteriochlorophyll. (Ref. 1074)							lmax (nm): methanol 280, 306, 361, 510 [Spectrum 1139] (Ref. 1071)		¹H-NMR (CDCl₃): 1.07 s (16, 17-H₃), 1.16 s (16', 17'-H₃), 1.36 d (J=4.8 Hz; 3-OH), 1.47 t (2-Hax), 1.74 s (18-H₃), 1.77 m (2-Heq), 1.98 s (19, 20-H₃), 2.01 s (18'-H₃), 2.03 s (20'-H₃), 2.05 m (4-Hax), 2.34 d (J=7.6 hZ; 2'-H₂), 2.38 m (4-Heq), 3.24 s (1'-O-CH₃), 3.98 m (3-Hax), 9.54 d (J=1.9 Hz; 19'-H aldehyde) (Ref. 1071)	FD-MS m/z: 596 (Ref. 1053/1071)	CD (Ref. 1071) Resonance Raman spectra, and fluorescence excitaiton specta (Ref. 1074)		Erythrobacter longus (aerobic photosynthetic bacterium) (Ref. 1071) Porphyrobacter tepidarius (thermophilic aerobic photosynthetic bacterium) (Ref. 1214) Porphyrobacter cryptus, Porphyrobacter neustonensis, Erythrobacter litoralis, Erythromicrobium ramosum based on TLC (aerobic photosynthetic bacterium) (Ref. 1237)					[1053] / [1071] / [1074] / [1214] / [1237]
144		Erythroxanthin	(3S,2'R,3'R)-3,2',3'-Trihydroxy-b,b-caroten-4-one	VCA1064	Shinichi Takaichi		C₄₀H₅₄O₄	598.854									lmax (nm): methanol 460 (Ref. 1072)		¹H-NMR (CDCl₃): 0.99 s (16'-H₃), 1.12 s (17'-H₃), 1.20 s (16-H₃), 1.31 s (17-H₃), 1.71 s (18'-H₃), 1.93 s (18-H₃), 1.96 s (19'-H₃), 1.97 s (20, 20'-H₃), 1.99 s (19-H₃), 1.80 t (J=13 Hz; 2-Hax), 2.13 dd (J=10 17 Hz; 4'-Hax), 2.14 dd (J=6, 13 Hz; 2-Heq), 2.47 dd (J=6, 17 Hz; 4'-Heq), 3.31 d (J=10 Hz; 2'-Hax), 3.82 ddd (J=7, 10, 10 Hz; 3'-Hax), 4.31 dd (J=6, 14 Hz; 3-Hax) (Ref. 1072) (Ref. 1343)	FD-MS m/z: 598 (Ref. 1072); EIMS, HR-EIMS (Ref. 1343)	CD in EPA(Ref. 1072/1343)		Erythrobacter longus (aerobic photosynthetic bacterium) (Ref. 1072) Brevundimonas sp. SD212 (bacterium) (Ref. 1343)					[1072] / [1343]
145		Erythroxanthin sulfate	Sodium (3S,2'R,3'R)-2',3'-dihydroxy-4-oxo-b,b-caroten-3-yl sulfate	VCA1065	Shinichi Takaichi		C₄₀H₅₄O₇S	678.919		Erythroxanthin sulfate is a dominant carotenoid species in the membranes of Erythrobacter longus, but does not transfer the absorbed light energy to bacteriochlorophyll. Resonance Raman spectra indicate that this carotenoid does not interact with either bacteriochlorophyll or proteins in the membranes. (Ref. 1074)							lmax (nm): methanol/H₂O (4:1) 40 mM NH₄OH, 469 (Ref. 1072)	Sulfate residue; n^K^B^r_m_a_x cm^-¹: 618 s (S-O str.), 1120 vs (S=O str.), 3400 vs (O-H str.) (Ref. 1072)	¹H-NMR (CDCl₃/CD₃OD 3:1): 0.98 s (16'-H₃), 1.11 s (17'-H₃), 1.24 s (16-H₃), 1.37 s (17-H₃), 1.71 s (18'-H₃), 1.91 s (18-H₃), 1.97 s (19'-H₃), 1.98 s (20, 20'-H₃), 2.00 s (19-H₃), 2.03 t (J=14 Hz; 2-Hax), 2.11 dd (J=10, 17 Hz; 4'-Hax), 2.37 dd (J=5, 13 Hz; 2-Heq), 2.43 dd (J=7, 17 Hz; 4'-Heq), 3.25 d (J=10 Hz; 2'-Hax), 3.78 ddd (J=7, 10, 10 Hz; 3'-Hax), 5.08 dd (J=5, 14 Hz; 3-Hax) (Ref. 1072)	FD-MS m/z: 692 methyl ester (Ref. 1053/1072)	CD (Ref. 1072) Resonance Raman spectra, and fluorescence excitaiton specta (Ref. 1074)		Erythrobacter longus (aerobic photosynthetic bacterium) (Ref. 1072)				Sulfate is easily removed by the treatment in 0.6 M HCl/THF for 10 min at room temperature. Erythroxanthin sulfate is methylated with diazomethane. (Ref. 1072)	[1053] / [1072] / [1074]
146		Caloxanthin 3-sulfate	Sodium (3R,2'R,3'R)-2',3'-dihydroxy-b,b-caroten-3-yl sulfate	VCA1066	Shinichi Takaichi		C₄₀H₅₆O₆S	664.935									lmax (nm): methanol/H₂O (4:1) 40 mM NH₄OH, 344, 450, 475, %III/II=29 (Ref. 1072)		¹H-NMR (CDCl₃/CD₃OD 3:1): 0.98 s (16-H₃), 1.07 s (16', 17'-H₃), 1.11 s (17-H₃), 1.60 t (J=12 Hz; 2-Hax), 1.71 s (18-H₃), 1.72 s (17'-H₃), 1.97 s (19, 20, 19', 20'-H₃), ca. 2.02 (2'-Heq), 2.11 dd (J=10, 17 Hz; 4-Hax), 2.24 dd (J=10, 16 Hz; 4-Hax), 2.59 dd (J=5, 17 Hz; 4-Heq), 2.44 dd (J=6, 17 Hz; 4-Heq), 3.25 d (J=10 Hz; 2-Hax), 3.78 ddd (J=7, 10, 10 Hz; 3-Hax), 4.70 m (3-Hax) (Ref. 1072)	FD-MS m/z: 678 methyl ester (Ref. 1072)	CD (Ref. 1072)		Erythrobacter longus (aerobic photosynthetic bacterium) (Ref. 1072)					[1072]
147		3,4-Dihydrospheroidene/ Methoxyneurosporene	1-Methoxy-1,2,7',8'-tetrahydro-y,y-carotene	VCA1067	Shinichi Takaichi		C₄₁H₆₂O	570.930									lmax (nm): methanol 329, 413, 437, 465, %III/II=87.6 [Spectrum 1140] (Ref. 1052)						Rhodobacter, Rhodovulum, Rhodobaca, Rhodoferax, Rubrivivax, Roseobacrer species, and Rhodobacter sphaeroides Ga mutant (purple photosynthetic bacteria) (Ref. 1054)		This carotenoid seems to be by-product in the spheroidene pathway of purple photosynthetic bacteria. Rhodobacter sphaeroides Ga mutant accumulats this carotenoid (Ref. 1054). The crtD mutant of Rhodobacter sphaeroides cultured under anaerobic conditions accumulats neurosporene, chloroxanthin and methoxyneurosporene (Ref. 1089). Methoxyneurosporene is not the substrate of CrtD of Rhodobacter sphaeoides and Rubrivivax gelatinosus in vitro (Ref. 1118/1192). [Table 1014]			[1052] / [1054] / [1089] / [1118] / [1192]
148		Hydroxyspheroidene/ OH-Spheroidene	1'-Methoxy-3',4'-didehydro-1,2,7,8,1',2'-hexahydro-y,y-caroten-1-ol	VCA1068	Shinichi Takaichi	OH-SE	C₄₁H₆₂O₂	586.930		Carotenoid compositions in the RC-LH1 and LH2 complexes from the anaerobic and semi-aerobic cultures of the purple photosynthetic bacterium, Rubrivivax gelatinosus (Ref. 1076)							lmax (nm): methanol 344, 426, 451, 482, %III/II=78.2 [Spectrum 1141] (Ref. 1052)						Carotenoid of the spheroidene pathway of the purple photosynthetic bacteria. (Ref. 1054)		One of the final products in the spheroidene pathway of purple photosynthetic bacteria (Ref. 1054). The crtA mutant of Rhodobacter sphaeroides cultured under anaerobic conditions acculatates spheroidene and OH-spheroidene (Ref. 1089). Spheroidene is changed to OH-shperoidene by CrtC from Rvi. gelatinosus, not by that from Rba. capusulatus (Ref. 1255). [Table 1015]			[1052] / [1054] / [1076] / [1089] / [1255]
149		Hydroxyspheroidenone/ OH-Spheroidenone	1'-Hydroxy-1-methoxy-3,4-didehydro-1,2,1',2',7',8'-hexahydro-y,y-caroten-2-one	VCA1069	Shinichi Takaichi	OH-SO	C₄₁H₆₀O₃	600.913		Carotenoid compositions in the RC-LH1 and LH2 complexes from the anaerobic and semi-aerobic cultures of the purple photosynthetic bacterium, Rubrivivax gelatinosus (Ref. 1076)							lmax (nm): hexane 482, 513; benzene: 499, 531 (shoulder) (Ref. 1073); methanol [Spectrum 1142]					Silicagel G TLC, benzene-hexane-acetone (5:5:1): Rf=0.27 (Ref. 1073)	Roseobacter denitrificans (=Erythrobacter sp. OCh 114) (aerobic photosynthetic bacterium) (Ref. 1073) Carotenoid of the spheroidene pathway under semi-aerobic culture of the purple photosynthetic bacteria. (Ref. 1054)		One of the final products in the spheroidene pathway of purple photosynthetic bacteria under semi-aerobic conditions (Ref. 1054). [Table 1016]			[1054] / [1073] / [1076]
150		Demethylspheroidenone	1-Hydroxy-3,4-didehydro-1,2,7',8'-tetrahydro-y,y-caroten-2-one	VCA1070	Shinichi Takaichi	DMSO	C₄₀H₅₆O₂	568.871									lmax (nm): methanol 299, 374, 485; reduced form 279, 345, 428, 451, 481, %III/II=59 [Spectrum 1143] (Ref. 1100)			FD-MS m/z: 568 (Ref. 1100/1260)			Rhodobaca bogoriensis (Ref. 1100), Rhodovulum sulfidophilum (Ref. 1350) (purple photosynthetic bacterium)		An intermediate in the spheroidene pathway of purple photosynthetic bacteria (Ref. 1054).	The crtF mutant of Rhodobacter capsulatus accumulats DMS and DMSO (Ref. 1102). The crtF mutant of Rubrivivax gelatinosus (photosynthetic bacteria) produces this carotenoid (Ref. 1260).		[1054] / [1100] / [1102] / [1260] / [1350]
151		2-Ketospirilloxanthin	1,1'-Dimethoxy-3,4,3',4'-tetradehydro-1,2,1',2'-tetrahydro-y,y-caroten-2-one	VCA1071	Shinichi Takaichi		C₄₂H₅₈O₃	610.908		Carotenoid compositions in the RC-LH1 and LH2 complexes from the anaerobic and semi-aerobic cultures of the purple photosynthetic bacterium, Rubrivivax gelatinosus (Ref. 1076)							lmax (nm): methanol 287, 334, 408, 507, 527 (shoulder), reduced form 368, 384, 463, 491, 524, %III/II=61 (Ref. 1076)			FD-MS m/z: 610 (Ref. 1076)			Rubrivivax gelatinosus (purple photosynthetic bacterium) (Ref. 1076)		[Table 1009] (Ref. 1076)			[1076]
152		2,2'-Diketospirilloxanthin/ Diketospirilloxanthin	1,1'-Dimethoxy-3,4,3',4'-tetradehydro-1,2,1',2'-tetrahydro-y,y-carotene-2,2'-dione	VCA1072	Shinichi Takaichi		C₄₂H₅₆O₄	624.892		Carotenoid compositions in the RC-LH1 and LH2 complexes from the anaerobic and semi-aerobic cultures of the purple photosynthetic bacterium, Rubrivivax gelatinosus (Ref. 1076)							lmax (nm): hexane 487, 518, 555; benzene 540, 578 (Ref. 1073); methanol 304, 352, 431 (shoulder), 522, 548 (shoulder), reduced form 369, 384, 464, 491, 524, %III/II=58 (Ref. 1076)			FD-MS m/z: 624 (Ref. 1076) (Ref. 0059)		Silicagel G TLC, benzene-hexane-acetone (5:5:1): Rf=0.51 (Ref. 1073)	Roseobacter denitrificans (=Erythrobacter sp. OCh 114) (aerobic photosynthetic bacterium) (Ref. 1073) Rubrivivax gelatinosus (purple photosynthetic bacterium) (Ref. 1076)		In Rhodobacter sphaeroides, replacing the native 3-step CrtI with the 4-step enzyme from Erwinia herbicola results in significant flux down the spirilloxanthin pathway, and diketospirilloxanthin is the major carotenoid (Ref. 1194). [Table 1010] (Ref. 1076)			[0059] / [1073] / [1076] / [1194]
153		3,4-Dihydrospheroidenone	1-Methoxy-1,2,7',8'-tetrahydro-y,y-caroten-2-one	VCA1073	Shinichi Takaichi		C₄₁H₆₀O₂	584.914									lmax (nm): methanol 328, 414, 436, 465, %III/II=89.1 [Spectrum 1144]; reduced form 329, 414, 436, 465, %III/II=82.9 (Ref. 1052/1075)		¹H-NMR (CDCl₃): 1.28 s (16, 17-H₃), 1.59 s (16'-H₃), 1.60 s (18'-H₃), 1.67 s (17'-H₃), 1.82 s (18, 19'-H₃), 1.95 s (20'-H₃), 1.96 s (19-H₃), 1.97 s (20-H₃), 2.04 (3'-H₂), ca. 2.1 (4', 8'-H₂), 2.12 (7'-H₂), 2.34 m (4--H₂), 2.75 t (J=8 Hz; 3--H₂), 3.21 s (1-O-CH₃), 5.08 t (J=7 Hz; 2'-H), 5.11 t (J=7 Hz; 6'-H), 5.95 d (J=11 Hz; 10'-H), 5.96 d (J=10 Hz; 6-H) (Ref. 1075)	FD-MS m/z: 584 (Ref. 1075)			Roseobacter denitrificans (=Erythrobacter sp. OCh 114) (aerobic photosynthetic bacterium) (Ref. 1075)		When the aerobic photosynthetic bacteirum, Roseobacter denitrificans (=Erythrobacter sp. OCh 114), is cultured in the dark, then subjected to illumination under anaerobic conditions, many unknown yellow pigments appeared and a considerable amount of spheroidenone disappeared. One of the yellow carotenoid is 3,4-dihydrospheroidenone. Presumably, over-reduction of the photosynthetic apparatus interfered with normal photosynthetic electron transfer and resulted in photoreduction of C=C double bond at the 3,4-position of spheroidenone. (Ref. 1075)			[1052] / [1075]
154		Loroxanthin/ 19-Hydroxylutein	(3R,3'R,6'R)-b,e-Carotene-3,19,3'-triol	VCA1074	Shinichi Takaichi		C₄₀H₅₆O₃	584.871									lmax (nm): diethyl ether/isopentane/ethanol (5:5:2) 262, 326, 418, 438, 465 (Ref. 1078); acetone 420, 443, 469, %III/II=39 (Ref. 1081); methanol/H₂O (9:1) 266, 332, 423 (shoulder), 445, 473, %III/II=50 [Spectrum 1145]		¹H-NMR (CDCl₃): 0.85 s (17'-H₃), 1.00 s (16'-H₃), 1.09 s (16, 17-H₃), 1.63 s (18'-H₃), 1.75 s (18-H₃, all-trans), 1.79 s (18-H₃, 9-cis), 1.84 dd (J=6, 13 Hz; H-2), 1.91 s (19'-H₃), 1.97 s (20, 20'-H₃), 2.07 (4-Hax), 2.38 dd (J=6, 16 Hz; 4-Heq), 2.40 d (J=10 Hz; 6'-H), 4.03 m (3-Hax), 4.25 m (3'-H), 4.39 s (19-H₂, 9-cis), 4.55 s (19-H₂, all-trans), 5.436 dd (J=10, 16 Hz; 7'-H), 5.547 m (4'-H), 6.048 d (J=16 Hz; 8-H), 6.138 d (J=16 Hz; 8'-H), 6.349 d (J=16 Hz; 7-H) (Ref. 1078/1081)		CD (Ref. 1078); CD l nm (de) pentane: 195 (- 5.8), 210 (0), 220 (1.4), 240 (1.3), 265 (1.4) (Ref. 1081)		Chlorella vulgaris (Ref. 1078); Botryococcus braunii (Botryococcaceae, Chlorococcales) (Ref. 1081); Cladophorales (Ulvophyceae, Chlorophyta) (Ref. 1330)		Biosynthesis might be in Cladophorales (Ulvophyceae, Chlorophyta): a-carotene lutein loroxanthin siphonaxanthin. Most species produce loroxanthin and no siphonaxanthin, while some produce siponaxanthin and some produce only lutein without loroxanthin and siphonaxanthin. Relationship between carotenoid types and molecular phylogeny is discussed (Ref. 1330>.		Loroxanthin in Botryococcus braunii were purified after saponification. (Ref. 1081)	[1078] / [1081] / [1330]
155		Loroxanthin ester/ Loroxanthin dodecenoate	(3R,3'R,6'R)-19-(trans-Dodec-2-enoyloxy)-b,e-carotene-3,3'-diol	VCA1075	Shinichi Takaichi		C₅₂H₇₆O₄	765.157									lmax (nm): methanol 445, 471, %III/II=42 (Ref. 1080)		¹H-NMR (CDCl₃): 0.83 s (17'-H₃), 0.98 s (16'-H₃), 1.03 s (16-H₃), 1.04 s (17-H₃), 1.35 dd (J=7, 13 Hz; 2'-Hax), ca. 1.41 (3'-OH), 1.45 dd (J=12, 12 Hz; 2-Hax), 1.61 s (18'-H₃), 1.71 s (18-H₃), 1.84 dd (J=6, 13 Hz; 2'-Heq), 1.89 s (19'-H₃), 1.95 s (20, 20'-H₃), 2.02 dd (J=10, 17 Hz; 4-Hax), 2.37 dd (J=7, 17 Hz; 4-Heq), 2.39 d (J=8 Hz; 6'-H), 3.98 m (3-Hax), 4.23 m (3'-H), 5.04 s (19-H₂), 5.42 dd (J=10, 16 Hz; 7'-H), 5.53 brs (4'-H), 6.04 d (J=16 Hz; 8-H), 6.19 d (J=17 Hz; 7-H), fatty acid moiety 0.86 t (J=7 Hz; terminal CH₃), 1.23 (CH₂), 1.41 (5-H₂), 2.16 dddd (J=1.4, 7.1, 7.2, 7.3 Hz; 4-H₂), 5.80 ddd (J=105, 1.7, 15.6 Hz; 1-H), 6.97 ddd (J=6.8, 7.1, 15.6 Hz; 2-H) (Ref. 1080)	FD-MS m/z: 764 (100%), [M-18]⁺ (2%) (Ref. 1053/1080)	CD (Ref. 1080)		Pyramimonas parkeae NIES 254 (Prasinophyceae) and a chlorarachniophycean alga (Ref. 1080)					[1053] / [1080]
156		Siphonaxanthin	(3R,3'R,6'R)-3,19,3'-Trihydroxy-7,8-dihydro-b,e-caroten-8-one	VCA1076	Shinichi Takaichi	Sx	C₄₀H₅₆O₆	632.869		Siphonaxanthin in the chloroplasts ofgreen alga Codium fragile exhibits a new absorption band at approximately 535 nm, and this might originat a nwe excited state (S_x) between the S₂ and S₁ states based on fluorescence anisotrophy decay (Ref. 1286).							lmax (nm): methanol 451, and reduced form 309, 397, 419, 446, %III/II=97.7 [Spectrum 1146] (Ref. 1052/1079); acetone 441, (461) (Ref. 1248)		1H-NMR in CDCl3 (Ref. 1248)	FD-MS m/z: 600 (Ref. 1079) EI-MS (Ref. 1248)		HPLC of Mesostigma viride (Prasinophyceae) (Ref. 1250)	Chlamydomonas parkeae NIES 441 (Ref. 1079), Codium (Ref. 1248), Mesostigma (Prasinophyceae) (Ref. 1250), Cladophorales (Ulvophyceae, Chlorophyta) (Ref. 1330).		Biosynthesis might be in Cladophorales (Ulvophyceae, Chlorophyta): a-carotene lutein loroxanthin siphonaxanthin. Most species produce loroxanthin and no siphonaxanthin, while some produce siponaxanthin and some produce only lutein without loroxanthin and siphonaxanthin. Relationship between carotenoid types and molecular phylogeny is discussed (Ref. 1330>.		Identical with xanthophyll K1S. Some green alga have siphonaxanthin ester(s), usually 2-trans-dodecenoate (Ref. 1079).	[1052] / [1079] / [1248] / [1250] / [1286] / [1330]
157		Siphonaxanthin ester/ Siphonaxanthin dodecenoate/ (Siphonein)	(3R,3'R,6'R)-19-(trans-Dodec-2-enoyloxy)-3,3'-dihydroxy-7,8-dihydro-b,e-caroten-8-one	VCA1077	Shinichi Takaichi	Sx-FA	C₅₂H₇₆O₅	781.157		6'-Hydroxysiphonaxanthin ester and siphonaxanthin ester have function as antenna pigments in Pterosperma (Ref. 1249). Siphonaxanthin ester has function as antenna pigments in Mesostigma (Ref. 1250).							lmax (nm): acetone 448, (463) (Ref. 1248); methanol 455 and its reduced form 402, 425, 452, %III/II=93 (Ref. 1249); methanol [Spectrum 1147]		1H-NMR in CDCl3 (Ref. 1248) 1H- and 13C-NMR in CDCl3 (Ref. 1249/1250)	FD-MS m/z: 724 for C8:1 (Ref. 1352), 780 for C12:1 (Ref. 1079/1352), 808 for C14:1 (Ref. 1249/1352) 782 for C12:0 and 810 for C14:0 (Ref. 1250); EI-MS (Ref. 1248)	CD in hexane (Ref. 1248)	HPLC of Pterosperma cristatum (Ref. 1249), and Mesostigma viride (Ref. 1250) (Prasinophyceae, Chlorophyta).	Chlamydomonas parkeae NIES 441, Codium divaricatum, Codium latum, Bryopsis maxima, Caulerpa sertularioides and Caulerpa serrulata (green algae) (Ref. 1079) Codium and Pyramimonas (Ref. 1248) Pterosperma, Mesostigma and Nephroslmis (Prasinophyceae) (Ref. 1249/1250/1352)				Identical with xanthophyll K1. Esterified fatty acids in Chlamydomonas parkeae are 2-trans-dodecenoate, 2-trans-decenoate and 2-trans-octenoate, while other species have only 2-trans-dodecenoate. Since the name ""siphonein"" can not specify the fatty acid moiety, siphonaxanthin ester is proposed (Ref. 1079). Pyraminonas amylifera has 2-trans-dodecenoate and 2-trans-decenoate as esterified fatty acids (Ref. 1248). Pterosperma cristatum has 2-trans-tetradecenoate as esterified fatty acid (Ref. 1249). Mesostigma viride has saturated fatty acids, dodecanoate and tetradecanoate, as esterified ones (Ref. 1250). Majors in Nephroselmis astigmatica, N. pyriformis and Nephroselmis sp. MBIC 11158 are siphonaxanthin C14:1 ester, while that in Nephroselmis sp. MBIC 11149 is siphonaxanthin C8:1 ester (Ref. 1352). The keto group at C-8 of siphonaxanthin is single-bond trans-conformation for the conjugated double bond, and the double bond at C-2'' of fatty acid is trans-conformation determined by NMR (Ref. 1249).	[1079] / [1248] / [1249] / [1250] / [1352]
158		4-Ketonostoxanthin 3'-sulfate	Sodium (2R,3R,2'R,3'S)-2,2',3'-Trihydroxy-4-oxo-b,b-caroten-3-ul sulfate	VCA1078	Shinichi Takaichi		C₄₀H₅₄O₈SNa	717.908									lmax (nm): CHCl₃/methanol (2:1) (e) 478 (87.6) (Ref. 1040)	n^K^B^r_m_a_x cm^-¹: 3424(O-H), 1657 (C=O), 1386, 1253 (S=O), 1048, 965 (Ref. 1040)	¹H-NMR (CDCl₃/CD₃OD 2:1): 0.99 and 1.09 s (16', 17'-H₃), 1.20 and 1.23 s (16, 17-H₃), 1.66 s (18'-H₃), 1.87 s (18-H₃), 1.93-1.97 s (19, 20, 19', 20'-H₃), 2.28 dd (J=10, 18 Hz; 4'-H), 2.67 dd (J=7, 18 Hz; 4'-H), 3.42 d (J=10 Hz; 2'-H), 3.45 d (J=11.5 Hz; 2-H), 4.12 d (J=11.5 Hz; 3-H), 4.50 dt (J=7, 10 Hz; 3'-H) (Ref. 1040)	FABMS (pos.) m/z: 693 [M+H]⁺ (Ref. 1040)	CD l nm (de) CHCl₃/methanol (2:1): 262 (3.5), 304 (-10.3), 343 (0.1), 388 (-0.6) (Ref. 1040)		Flavobacterium sp. strain PC-6 (Ref. 1040)					[1040]
159		Deoxyflexixanthin/ 4-Keto-1'-hydroxytorulene/ Keto-myxocoxanthin	1'-Hydroxy-3',4'-didehydro-1',2'-dihydro-b,y-caroten-4-one	VCA1079	Shinichi Takaichi		C₄₀H₅₄O₂	566.856			150-160 C (Ref. 1085); 155-160 C (Ref. 1355); 135-136 C (chemical synthesis) (Ref. 1077)						lmax (nm): acetone 480.5, 508; petroleum ether 476.5, 503; methanol 477.5, 500 (shoulder) (Ref. 1085); light petroleum 474, 504; benzene 490, 520; chloroform 490, 519 (Ref. 1087); methanol [Spectrum 1148] ; petroleum ether or hexane 477, (504) (Ref. 1355); ethanol 480, (504) (Ref. 1359)	n^K^B^r_m_a_x cm^-¹: 1650, 960 (Ref. 1087/1355)	¹H-NMR (CDCl₃): 1.20 s (16, 17-H₃), 1.23 s (16', 17'-H₃), 1.87 s (18-H₃), 1.95 s (18'-H₃), 1.98 s (19, 20, 19', 20'-H₃), ca. 2.4 (4, 2'-H₂) (Ref. 1087)	FD-MS: 566 (Ref. 1354); HR-MS (Ref. 1355)			Flexibacter sp. (Ref. 1085), Flexibacter strain NIVA BR6-64 (Ref. 1086/1088) (non-gliding bacterium) Aerobic dark and anaerobic light cultures of Roseiflexus castenholzii (thermophilic filamentous photosynthetic bacterium) (Ref. 1354) Major carotenoid of a halophilic sperochete (spirochete RS1) (Ref. 1355), and minor one of Stigmatella aurantiaca strain Sg a1 (Myxobacteriles) (Ref. 1359).	Chemical synthesis (Ref. 1087)				[1077] / [1085] / [1086] / [1087] / [1088] / [1354] / [1355] / [1359]
160		1',2'-Dihydro-g-carotene	1',2'-Dihydro-b,y-carotene	VCA1080	Shinichi Takaichi		C₄₀H₅₈	538.889									lmax (nm): acetonitrile/methanol/THF (58:35:7) 440 (shoulder), 461, 491, %III/II=38 (Ref. 1057)		¹H-NMR (CDCl3) (Ref. 1103)	FD-MS m/z: 538 (Ref. 1103)		HPLC (column; Novapak C18 (Waters) 8 X 100 mm: eluelnt; acetonitrile/methanol/THF 58:35:7: flow 2.0 ml/min) Rt=17.8 min (Ref. 1057)	Chlorobium (present name, Chlorobaculum) tepidum strain TNO (green sulfur bacterium) (Ref. 1103)					[1057] / [1103]
161		Chlorobactene	f,y-Carotene	VCA1081	Shinichi Takaichi		C₄₀H₅₂	532.841		Chlorobactene is mainly distributed in chlorosomes, and 2 moles/ P840 is found in FMO-RC from Chlorobium tepidum strain TLS (Ref. 1104). The ratio chlorobactene to 1',2'-dihydrochlorobactene decreased from 5 to 0.7 in the light-limited cultures of Chlorobium tepidum cells (Ref. 1171).							lmax (nm): acetonitrile/methanol/THF (58:35:7) 287, 354, 440 (shoulder), 461, 490, %III/II=38.3 [Spectrum 1021] (Ref. 1057/1103); methanol [Spectrum 1149]		¹H-NMR (CDCl3) (Ref. 1103)	FD-MS m/z: 532 (Ref. 1103) (Ref. 0059)		HPLC (column; Novapak C18 (Waters) 8 X 100 mm: eluelnt; acetonitrile/methanol/THF 58:35:7: flow 2.0 ml/min) Rt=9.8 min (Ref. 1057)	Chlorobium (present name, Chlorobaculum) tepidum (green sulfur bacterium) (Ref. 1103)			Chlorobactene is produced by CrtU, g-carotene desaturase, from g-carotene in Chlorobium tepidum (green sulfur bcterium) (Ref. 1295).		[0059] / [1057] / [1103] / [1104] / [1171] / [1295]
162		1',2'-Dihydrochlorobactene	1',2'-Dihydro-f,y-carotene	VCA1082	Shinichi Takaichi		C₄₀H₅₄	534.857		Dihydrochlorobactene is mainly distributed in chlorosomes from Chlorobium tepidum strain TLS (Ref. 1104). The ratio chlorobactene to 1',2'-dihydrochlorobactene decreased from 5 to 0.7 in the light-limited cultures of Chlorobium tepidum cells (Ref. 1171).							lmax (nm): acetonitrile/methanol/THF (58:35:7) 287, 352, 439 (shoulder), 461, 490, %III/II=47.1 [Spectrum 1022] (Ref. 1057/1103)		¹H-NMR (CDCl3) (Ref. 1103)	FD-MS m/z: 534 (Ref. 1103)		HPLC (column; Novapak C18 (Waters) 8 X 100 mm: eluelnt; acetonitrile/methanol/THF 58:35:7: flow 2.0 ml/min) Rt=12.3 min (Ref. 1057)	Chlorobium (present name, Chlorobaculum) tepidum (green sulfur bacterium) (Ref. 1103)					[1057] / [1103] / [1104] / [1171]
163		Hydroxychlorobactene/ OH-Chlorobactene	1',2'-Dihydro-f,y-caroten-1-ol	VCA1083	Shinichi Takaichi		C₄₀H₅₄O	550.856									lmax (nm): methanol 283, 348, 438 (shoulder), 459, 488, %III/II=52.2 (S. Takaichi) (Ref. 1103)			FD-MS m/z: 550 (Ref. 1103)			Chlorobium (present name, Chlorobaculum) tepidum (green sulfur bacterium) (Ref. 1103)			1'-OH-Chlorobactene is produced by CrtC, carotenoid 1',2'-hydrotase, from chlorobactene in Chlorobium tepidum (green sulfur bcterium) (Ref. 1295).		[1103] / [1295]
164		Hydroxychlorobactene glucoside/ OH-Chlorobactene glucoside	1'-b-D-glucopyranosyloxy-1',2'-dihydro-f,y-carotene	VCA1084	Shinichi Takaichi		C₄₆H₆₄O₆	712.997															Chlorobium (present name, Chlorobaculum) tepidum strain S.Pte (green sulfur bacterium) (Ref. 1103)					[1103]
165		Hydroxychlorobactene glucoside ester/ OH-Chlorobactene glucoside ester	1'-[(6-O-Acyl-b-D-glucopyranosyl)oxy]-1',2'-dihydro-f,y-carotene	VCA1085	Shinichi Takaichi					This is mainly distributed in chlorosome-free membranes, and 1.9 moles/ P840 is found in FMO-RC from Chlorobium tepidum strain TLS (Ref. 1104).							lmax (nm): methanol 286, 351, 437 (shoulder), 459, 489, %III/II=49.7 (S. Takaichi) (Ref. 1103)			FD-MS m/z: 898 (laurate) (Ref. 1103)			Chlorobium (present name, Chlorobaculum) tepidum strain TNO and MET (green sulfur bacterium) has only C12:0 ester(Ref. 1103). Chlorobium phaeobacteroides 1549 (new name, Chlorobaculum limnaeum 1549; green-sulfur bacterium) has trace amount of this carotenoid, and esterified fatty acid is only C12:0 (Ref. 1282).				In Chlorobium tepidum, the esterified fatty acid is only laurate determined by GLC (Ref. 1103).	[1103] / [1104] / [1282]
166		1'-Hydroxy-g-carotene glucoside/ 1'-OH-g-Carotene glucoside/ (Carotenoids B-G)	1'-b-D-glucopyranosyloxy-1',2'-dihydro-b,y-carotene	VCA1086	Shinichi Takaichi	B-G	C₄₆H₄₈O₆	696.870									lmax (nm): methanol 437 (shoulder), 458, 486, %III/II=33.0 (Ref. 1105)			FD-MS m/z: 716 (Ref. 1053/1105)			Chloroflexus aurantiacus (Ref. 1105) and Chloroflexus aggregans (S. Takaichi) (Ref. 1106) (green filamentous bacteria) Rhodococcus rhodochrous (Nocardioform actinomycetes) (Ref. 1094/1111)					[1053] / [1094] / [1105] / [1106] / [1111]
167		1'-Hydroxy-g-carotene glucoside ester/ 1'-OH-g-Carotene glucoside ester/ (Carotenoid B-G-FA)	1'-[(6-O-Acyl-b-D-glucopyranosyl)oxy]-1',2'-dihydro-b,y-carotene	VCA1087	Shinichi Takaichi	B-G-FA				This is mainly distributed in chlorosome-free membranes, and 2.6 moles/ P840 is found in FMO-RC from Chlorobium tepidum strain TLS (Ref. 1104).							lmax (nm): methanol 282, 351, 438 (shoulder), 459, 489, %III/II=49.4 (S. Takaichi) (Ref. 1103), 437 (shoulder), 458, 487, %III/II=26.3 (Ref. 1105)		¹H-NMR (CDCl3) (Ref. 1105)	FD-MS m/z: 894 (laurate) (Ref. 1103) FD-MS m/z: 954 (C16:0), 952 (C16:1) (Ref. 1105)			Chlorobium (present name, Chlorobaculum) tepidum strain TNO and MET (green sulfur bacterium) has only C12:0 ester(Ref. 1103). Chlorobium phaeobacteroides 1549 (new name, Chlorobaculum limnaeum 1549; green-sulfur bacterium) has trace amount of this carotenoid, and esterified fatty acid is only C12:0 (Ref. 1282). Chloroflexus aurantiacus has mainly C16:0 and C16:1 esters(Ref. 1105) and Chloroflexus aggregans has mainly C16:0 and C18:1 esters (S. Takaichi) (Ref. 1106) (green filamentous bacteria). Rhodococcus rhodochrous (Nocardioform actinomycetes) (Ref. 1094/1111)				In Chlorobium tepidum, the esterified fatty acid is only laurate determined by GLC (Ref. 1103). In Chloroflexus aurantiacua strains J-10-fl and OK-70-fl, the major esterified fatty acid is C16:0 and C16:1 (Ref. 1105), and that is C16:0, C16:1, C18:0 and C18:1 in Chloroflexus aggregans (S. Takaichi) (Ref. 1106).	[1094] / [1103] / [1104] / [1105] / [1106] / [1111] / [1282]
168		1'-Hydroxy-g-carotene glucoside mycolic acid ester/ 1'-OH-g-Carotene glucoside mycolic acid ester/ (Carotenoid B-G-Myc)	1'-[(6-O-Mycoloyl-b-D-glucopyranosyl)oxy]-1',2'-dihydro-b,y-carotene	VCA1088	Shinichi Takaichi	B-G-Myc											lmax (nm): methanol 442 (shoulder), 461, 490 (Ref. 1110)			FD-MS m/z: 1278, 1306, 1332, 1334, 1360, 1362, 1388 (These are main molecular ion peaks and each corresponds to the different esterified mycolic acids.) (Ref. 1110)			Rhodococcus rhodochrous (Nocardioform actinomycetes) (Ref. 1111)					[1110] / [1111]
169		4-Keto-g-carotene/ Keto-g-carotene	b,y-Caroten-4-one	VCA1089	Shinichi Takaichi		C₄₀H₅₄O	550.856									lmax (nm): methanol 269, 307, (438), 466, (485) [Spectrum 1150]; NaBh4 reduced form 285, 348, (436), 458, 488, %III/II=44 (Ref. 1354)			FD-MS: 550 (Ref. 1354)			Rhodococcus rhodochrous (Nocardioform actinomycetes) (Ref. 1111), Rhodococcus erythropolis (Ref. 1094) One of major carotenods in anaerobic light culture of Roseiflexus castenholzii (thermophilic filamentous photosynthetic bacterium) (Ref. 1354)		A mutant of Rhodococcus rhodochrous accumulats g-karotene and 4-keto-g-karotene (Ref. 1111).	b-Carotene ketolasse from g-carotene to 4-keto-g-carotene is functionally identified from Rhodococcus erythropolice, and can produce canthaxanthin (Ref. 1333).		[1094] / [1111] / [1333] / [1354]
170		1',2'-Dihydro-1'-hydroxy-4-keto-g-carotene/ 1'-OH-4-Keto-g-carotene/ (Carotenoid K)	1'-Hydroxy-1',2'-dihydro-b,y-caroten-4-one	VCA1090	Shinichi Takaichi		C₄₀H₅₆O₂	568.871									lmax (nm): hexane 463, 488 (shoulder); reduced form 432, 456, 487, %III/II=38.1 [Spectrum 1151] (Ref. 1108)		¹H-NMR (CDCl3) (Ref. 1108)	FD-MS m/z: 568 (Ref. 1053/1108)			Rhodococcus rhodochrous (Nocardioform actinomycetes) (Ref. 1094/1111)		Influence of growth temperature on carotenoid content and composition in Rhodococcus rhodochrous (Ref. 1109)			[1053] / [1094] / [1108] / [1109] / [1111]
171		1'-Hydroxy-4-keto-g-carotene glucoside/ 1'-OH-4-Keto-g-carotene glucoside/ (Carotenoid K-G)	1'-b-D-glucopyranosyloxy-1',2'-dihydro-b,y-caroten-4-one	VCA1091	Shinichi Takaichi	K-G	C₄₆H₆₆O₇	731.012											¹H-NMR (CDCl3) (Ref. 1108)	FD-MS m/z: 730 (Ref. 1108)			Rhodococcus rhodochrous (Nocardioform actinomycetes) (Ref. 1094/1111)		Influence of growth temperature on carotenoid content and composition in Rhodococcus rhodochrous (Ref. 1109)			[1094] / [1108] / [1109] / [1111]
172		1'-Hydroxy-4-keto-g-carotene glucoside ester/ 1'-OH-4-Keto-g-carotene glucoside ester/ (Carotenoid K-G-FA)	1'-[(6-O-Acyl-b-D-glucopyranosyl)oxy]-1',2'-dihydro-b,y-caroten-4-one	VCA1092	Shinichi Takaichi	K-G-FA													¹H-NMR (CDCl3) (Ref. 1108)	FD-MS m/z: 968-1036 (depend on the esterified fatty acid species) (Ref. 1053/1108)			Rhodococcus rhodochrous (Nocardioform actinomycetes) (Ref. 1094/1111)		Influence of growth temperature on carotenoid content and composition in Rhodococcus rhodochrous (Ref. 1109)		After saponifying these carotenoids in a methanolic KOH solution, the carotenoid moiety is carotenoid K-G. After acidic methanolysis of these, fatty acid methyl esters are identified by GLC and major ones are C16:0, C17:0, C18:0, C19:0, C18:1, C19:1, C20:1, C21:1 and 10-methyl C19:0 (Ref. 1108).	[1053] / [1094] / [1108] / [1109] / [1111]
173		1'-Hydroxy-4-keto-g-carotene glucoside mycolic acid ester/ 1'-OH-4-Keto-g-carotene glucoside mycolic acid ester/ (Carotenoid K-G-Myc)	1'-[(6-O-Mycoloyl-b-D-glucopyranosyl)oxy]-1',2'-dihydro-b,y-caroten-4-one	VCA1093	Shinichi Takaichi	K-G-Myc											lmax (nm): methanol 470, 490 (shoulder); reduced form 440 (shoulder), 460, 490 (Ref. 1110)		¹H-NMR and ¹³H-NMR (CDCl3) (Ref. 1110)	FD-MS m/z: 1292, 1320, 1346, 1348, 1374, 1402 (These are main molecular ion peaks and each corresponds to the different esterified mycolic acids.) (Ref. 1110)			Rhodococcus rhodochrous (Nocardioform actinomycetes) (Ref. 1111)					[1110] / [1111]
174		3,4-Dihydrospirilloxanthin	1,1'-Dimethoxy-3,4-didehydro-1,2,1',2'-tetrahydro-y,y-carotene	VCA1094	Shinichi Takaichi		C₄₂H₆₂O₂	598.940		The light-harvesting complex of Rhodospirillum rubrum (Ref. 1120)							lmax (nm): n-hexane 372, 382, 454, 482, 515 (Ref. 1120)			EI-MS m/z: 598 [M], [M-30], [M-32], [M-106-30], [M-160-32] (Ref. 1120)			Rhodospirillum rubrum S1 (purple photosynthetic bacterium) (Ref. 1120)		This carotenoid seems to be by-product in the normal spirilloxanthin pathway of purple photosynthetic bacteria (Ref. 1054).			[1054] / [1120]
175		1-OH-3',4'-Didehydrolycopene/ 3',4'-Dehydrorhodopin	3',4'-Didehydro-1,2-dihydro-y,y-caroten-1-ol	VCA1095	Shinichi Takaichi		C₄₀H₅₆O	552.872									lmax (nm): methanol 318, 388, 466, 492, 526, %III/II=59 (Ref. 1064)			FD-MS m/z: 552 (Ref. 1064)					Escherichia coli, which carries the crtE, crtB, crtI, crtY and crtZ genes from the epiphytic bacterium Erwinia uredovora and the crtC gene from the purple photosynthetic bacterium Rhodobacter capsulatus, has synthesized this carotenid (Ref. 1064).			[1064]
176		3,1'-Dihydroxy-g-Carotene/ 3,1'-(OH)₂-g-Carotene	(3R)-1',2'-Dihydro-b,y-carotene-3,1'-diol	VCA1096	Shinichi Takaichi		C₄₀H₅₈O₂	570.887									lmax (nm): methanol 282, 349, (437), 459, 486, %III/II=54 (Ref. 1064)			FD-MS m/z: 570 (Ref. 1064)	CD (Ref. 1064)					Escherichia coli, which carries the crtE and crtB genes from the epiphytic bacterium Erwinia uredovora, the al-1 gene from Neurospora and the crtC gene from the purple photosynthetic bacterium Rhodobacter capsulatus, has synthesized this carotenid (Ref. 1064).		[1064]
177		Didemethylspirilloxanthin/ 1,1'-(OH)₂-3,4,3',4'-Tetradehydrolycopene	3,4,3',4'-Tetradehydro-1,2,1',2'-tetrahydro-y,y-carotene-1,1'-diol	VCA1097	Shinichi Takaichi		C₄₀H₅₆O₂	568.871			m.p. 225 C (Ref. 1341)						lmax (nm): methanol 316, 386, 466, 492, 525, %III/II=59 (Ref. 1064); acetone 469, 497, 531 (e 112, 157, 135 *10³) (Ref. 1341); methanol 468, 494, 528 ; ethanol 306, 317, 371, 388, 468, 494, 528 (Ref. 1342)	(Ref. 1341/1342)	1H-NMR in CDCl3 and pyridine (Ref. 1342)	FD-MS m/z: 568 (Ref. 1064/1260); EI-MS, CI-MS (Ref. 1342)			Polyangium fumosum (Myxobacteria, bacteria) (Ref. 1342)	(Ref. 1341)	Escherichia coli, which carries the crtE, crtB and crtI genes from the epiphytic bacterium Erwinia uredovora, the crtC gene from the purple photosynthetic bacterium Rhodobacter capsulatus and the crtD gene from Rhodobacter sphaeroides, has synthesized this carotenid (Ref. 1064).	The crtA and crtF mutant of Rubrivivax gelatinosus (photosynthetic bacteria) produces this carotenoid (Ref. 1260).	Didemethylspirilloxanthin glucoside and didemethylspirilloxanthin glucoside esters are also present (Ref. 1342).	[1064] / [1260] / [1341] / [1342]
178		1,1'-Dihydroxy-3,4-didehydrolycopene/ 1,1'-(OH)₂-3,4-Didehydrolycopene	3,4-Didehydro-1,2,1',2'-tetrahydro-y,y-carotene-1,1'-diol	VCA1098	Shinichi Takaichi		C₄₀H₅₈O₂	570.887									lmax (nm): methanol 305, 373, 456, 481, 513, %III/II=59 (Ref. 1064/1193)			FD-MS m/z: 570 (Ref. 1064/1093)					Escherichia coli, which carries the crtE, crtB and crtI genes from the epiphytic bacterium Erwinia uredovora, the crtC gene from the purple photosynthetic bacterium Rhodobacter capsulatus and the crtD gene from Rhodobacter sphaeroides, has synthesized this carotenid (Ref. 1064). 3,4-Dehydrorhodopin is changed to 1,1'-(OH)₂-3,4-didehydrolycopene by CrtC from Rvi. gelatinosus, not by that from Rba. capusulatus (Ref. 1255).			[1064] / [1093] / [1193] / [1255]
179		1-OH-3,4,3',4'-Tetradehydrolycopene/ 3,4,3',4'-Tetradehydrorhodopin	3,4,3',4'-Tetradehydro-1,2-dihydro-y,y-caroten-1-ol	VCA1099	Shinichi Takaichi		C₄₀H₅₄O	550.856									lmax (nm:) methanol 466, 500, 535 (Ref. 1193)			FD-MS m/z: 550 (Ref. 1193)					Escherichia coli, which carries the crtE and crtB genes from the epiphytic bacterium Erwinia uredovora, the al-1 gene from Neurospora,the crtC gene from the purple photosynthetic bacterium Rhodobacter capsulatus and the crtD gene from Rubrivivax gelatinosus, has synthesized this carotenid, while CrtD from Rhodobacter sphaeroides has no functions (Ref. 1193).			[1193]
180		Deinoxanthin	(2R)-2,1'-Dihydroxy-3',4'-didehydro-1',2'-dihydro-b,y-caroten-4-one	VCA1100	Shinichi Takaichi		C₄₀H₅₄O₃	582.855		antioxidation (Ref. 1196)							lmax (nm): methanol (451), 479, (506); chloroform (453), 492, (524); CS₂ (479), 509, 544; reduced form in ethanol 458, 474, 505 (Ref. 1195); acetone (454), 480, (507) (Ref. 1196)		1H-NMR in CDCl3 (Ref. 1195/1196) 13C-NMR (Ref. 1196)	APCI-MS (Ref. 1195) EI-MS (Ref. 1196)	CD in ether/isopentane/ethanol (5:5:2) (Ref. 1195/1196)		Deinococcus radiodurans (extremely radioresistant archaebacterum) (Ref. 1195/1196)			Lycopene b-cyclase (CrtLm) (Ref. 1278) and b-carotene ketolase (CrtO) (Ref. 1333) are functionally identified, and phytoene synthase (CrtB) and phytoene desaturase (CrtI) are homologically suggested (Ref. 1334) from Deinococcus radiodurans R1 (extremely radioresistant bacterum).		[1195] / [1196] / [1278] / [1333] / [1334]
181		Myxol	(3R,2'S)-3',4'-Didehydro-1',2'-dihydro-b,y-carotene-3,1',2'-triol	VCA1101	Shinichi Takaichi		C₄₀H₅₆O₃	584.871									lmax (nm): benzene 462, 488, 522 (Ref. 1216)		1H-NMR, 13C-NMR in CDCl3 (Ref. 1216)		CD in EPA(Ref. 1216)		Flavobacterium sp. P99-3 (MBIC 03313) (Ref. 1216) Agricone of myxol 2'-glycoside (myxoxanthophyll) in cyanobacteria.			On the biosynthesis of myxol in a marin bcterium strain P99-3, lycopene b-monocyclase (CrtYm) produces g-carotene from lycopene (Ref. 1241), and 1-hydroxy monocyclic carotenoid 3,4-dehydrogenase (CrtD) produces 1'-OH-torulene from 1'-OH-g-carotene (Ref. 1293). A gene cluster for myxol synthesis is sequenced from a marin bcterium strain P99-3, crtB, crtI, crtYm, crtD, crtA, crtZ, orf1 and orf2 (Ref. 1241), and two of them are functionally confirmed, crtYm and crtD. CrtD (Slr1293) is also functionally found from Synechocystis sp. strain PCC 6803 (cyanobacterium) (Ref. 1300).	Since the name myxoxanthophyll can not specify the sugar moiety and the identification of the sugar moiety is unfeasible in many cyanobacteria, the following naming convention is proposed by (Ref. 1222): when the sugar moiety is unknown, the name is myxol 2'-glycoside, when known, as in the case of rhamnose and a-L-fucose, they should be named myxol 2'-rhamnoside and myxol 2'-a-L-fucoside, respectively.	[1216] / [1222] / [1241] / [1293] / [1300]
182		Myxol glycoside/ (Myxoxanthophyll)	(3R,2'S)-2'-Glycosyloxy-3',4'-didehydro-1',2'-dihydro-b,y-carotene-3,1'-diol	VCA1102	Shinichi Takaichi												lmax (nm): methanol 294, 365, 448, 473, 503, %III/II=58 (Ref. 1222)	(Ref. 1228)	1H-NMR in CDCl3 (Ref. 1220/1221/1228), 1H-NMR, 13C-NMR in CDCl3 (Ref. 1222) 1H-NMR data in CDCl3 of the glycoside moiety of acetylated myxol 2'-glycosides (fucose, rhamnose and chinovose) (Ref. 1346)	(Ref. 1217/1218/1220/1222/1228/1346)	CD in EPA(Ref. 1219/1222/1346)		Myxol 2'-glycoside is found only in cyanobacteria, and the determination of the sugar moieties, including the L- or D-type and the a- or b-linkage, has been done only for a few species. (3R,2'S)-myxol 2'-O-methyl-methylpentoside from Oscillatoria limosa (Ref. 1217/1219) myxol 2'-a-L-chinovoside and myxol 2'-a-L-fucoside from Oscillatoria limnotica (Ref. 1221) myxol 2'-a-L-chinovoside from Oscillatoria agardhii (Ref. 1220) myxol 2'-(3-O-methyl-a-L-fucoside) from Oscillatoria bornetii (Ref. 1220> (3R,2'S)-myxol 2'-rhamnoside from Phormidium luridum (Ref. 1219) myxol 2'-rhamnoside from Anacystis nidulans (Ref. 1218) and Arthrospira sp. (Ref. 1228) (3R,2'S)-myxol 2'-(2,4-di-O-methyl-a-L-fucoside) from Synechocystis sp. PCC 6803 (Ref. 1222) (3R,2'S)-myxol 2'-a-L-fucoside from Anabaena sp. PCC 7120, Anabaena variabilis IAM M3 and Nostoc punctiforme PCC 73102 (Ref. 1346)				Since the name myxoxanthophyll can not specify the sugar moiety and the identification of the sugar moiety is unfeasible in many cyanobacteria, the following naming convention is proposed by (Ref. 1222): when the sugar moiety is unknown, the name is myxol 2'-glycoside, when known, as in the case of rhamnose and a-L-fucose, they should be named myxol 2'-rhamnoside and myxol 2'-a-L-fucoside, respectively. Glycoside is determined by GLC (Ref. 1220/1221), and GLC, TLC and paper chromatography (Ref. 1228).	[1217] / [1218] / [1219] / [1220] / [1221] / [1222] / [1228] / [1346]
183		Deoxymyxol/ (2'S)-Plectaniaxanthin	(2'S)-3',4'-Didehydro-1',2'-dihydro-b,y-carotene-1',2'-diol	VCA1103	Shinichi Takaichi		C₄₀H₅₆O₂	568.871										(2'S)-plectaniaxanthin (Ref. 1224).	1H-NMR, 13C-NMR in CDCl3 of deoxymyxol 2'-dimethyl fucoside (Ref. 1222). 1H-NMR in CDCl3 of (2'S)-plectaniaxanthin (Ref. 1224).	FD-MS (deoxymyxol 2'-dimethyl fucoside) (Ref. 1222)	CD in EPA of deoxymyxol 2'-dimethyl fucoside and phleixanthophyll (Ref. 1222) are the mirror image of that of (2'R)-plectaniaxanthin (Ref. 1219/1225). (2'S)-Plectaniaxanthin (Ref. 1224).		(2'S)-Deoxymyxol 2'-(2,4-di-O-methyl-aL-fucoside) from the wild and the CrtR mutant of Synechocystis sp. PCC 6803 (Ref. 1222)	(2'S)-Plectaniaxanthin = (2'S)-deoxymyxol (Ref. 1224)			Note: Although deoxymyxol from cyanobacteria and aglycon of phleixanthophyll from Mycobacterium phlei have the same structure including stereochemistry, the glycosilated positions are 2'-OH and 1'-OH, respectively. Although deoxymyxol and plectaniaxanthin have the same structure, the stereochemistry of 2'-OH is (2'S) and (2'R), respectively. CD of (2'S)-deoxymyxol 2'-dimethyl fucoside (Ref. 1222) is the same with that of (2'S)-phleixanthophyll and the mirror image of that of (2'R)-plectaniaxanthin (Ref. 1219/1225).	[1219] / [1222] / [1224] / [1225]
184		Plectaniaxanthin/ (2'R)-Plectaniaxanthin	(2'R)-3',4'-Didehydro-1',2'-dihydro-b,y-carotene-1',2'-diol	VCA1104	Shinichi Takaichi		C₄₀H₅₆O₂	568.871									lmax (nm): hexane 448, 472, 503 (Ref. 1224); ether: 450, 474, 503 (Ref. 1225)	(Ref. 1224)	1H-NMR in CDCl3 (Ref. 1224)	MS (Ref. 0059/1224)	CD in EPA of (2'R)-plectaniaxanthin (Ref. 1219/1225) is the mirror image of that of deoxymyxol 2'-dimethyl fucoside (Ref. 1222) and phleixanthophyll. CD of synthetic (2'S)-plectaniaxanthin (Ref. 1224).		(2'R)-Plectaniaxanthin from Plectania coccinea (fungi) (Ref. 1225)	(2'S)-Plectaniaxanthin (Ref. 1224)			Note: Although deoxymyxol and plectaniaxanthin have the same structure, the stereochemistry of 2'-OH is (2'S) and (2'R), respectively. CD of (2'R)-plectaniaxanthin (Ref. 1225) is the mirror image of that of (2'S)-deoxymyxol 2'-dimethyl fucoside (Ref. 1222) and (2'S)-phleixanthophyll (Ref. 1219).	[0059] / [1219] / [1222] / [1224] / [1225]
185		Oscillol	(2R,2'R)-3,4,3',4'-Tetradehydro-1,2,1',2'-tetrahydro-y,y-carotene-1,2,1',2'-tetrol	VCA1105	Shinichi Takaichi		C₄₀H₅₆O₄	600.870			mp 225 C (Ref. 1277)						lmax (nm): methanol 464, 492, 524 (Ref. 1226), 315, 388, 468, 493, 523 (Ref. 1277)		H, C-NMR in CDCl3 (Ref. 1277)	(Ref. 1277/1347)	CD in EPA at 180 C (Ref. 1277)		Agricone of oscillol diglycoside (oscillaxanthin) in cyanobacteria. (2S,2'S)-oscillol 2,2'-di(a-L-fucoside) from Gloeobacter violaceus (Ref. 1347)	(all-E, 2R,2?R)-oscillol (Ref. 1277)			Since the name oscillaxanthin can not specify the sugar moiety and the identification of the sugar moiety is unfeasible in many cyanobacteria, the following naming convention is proposed by (Ref. 1222): when the sugar moiety is unknown, the name is oscillol diglycoside, when known, as in the case of rhamnose, it should be named oscillol 2,2'-dirhamnoside.	[1222] / [1226] / [1277] / [1347]
186		Oscillol diglycoside/ Oacillol bisglycoside/ (Oscillaxanthin)	(2R,2'R)-2,2'-Di-(glycosyloxy)-3,4,3',4'-tetradehydro-1,2,1',2'-tetrahydro-y,y-carotene-1,1'-diol	VCA1106	Shinichi Takaichi												lmax (nm): acetone 467, 496, 529 (Ref. 1226)		1H-NMR in CDCl3 (Ref. 1221/1229)	MS (Ref. 1217/1220/1229)	CD in EPA (Ref. 1226)		Oscillol 2,2'-diglycoside is found only in cyanobacteria, and the determination of the sugar moieties, including the L- or D-type and the a- or b-linkage, has been done only for a few species. oscillol 2,2'-di(O-methyl-methylpentoside) from Oscillatoria limosa (Ref. 1217) (2R,2'R)-oscillol 2,2'-di(a-L-chinovoside) from Oscillatoria agardhii (Ref. 1220/1226) oscillol 2,2'-di(3-O-methyl-a-L-fucoside) from Oscillatoria bornetii (Ref. 1220> oscillol 2,2'-dirhamnoside from Arthrospira sp. (Ref. 1229) oscillol 2,2'-di(a-L-chinovoside) and oscillol 2,2'-di(a-L-fucoside) from Spirulina platemsis (Ref. 1221)				Since the name oscillaxanthin can not specify the sugar moiety and the identification of the sugar moiety is unfeasible in many cyanobacteria, the following naming convention is proposed by (Ref. 1222): when the sugar moiety is unknown, the name is oscillol 2,2'-diglycoside, when known, as in the case of rhamnose, it should be named oscillol 2,2'-dirhamnoside. The stereochemistry of 2-OH and 2'-OH in oscillol 2,2'-diglycoside was proposed to be (2R,2'R), while that of 2'-OH in myxol 2'-glycoside is determined to be (2'S) (Ref. 1219/1222). From the carotenogenesis, oscillol and myxol should heve the same stereochemistry, but the experimental evidence does not give a clear conclusion (S. Takaichi). Glycoside is determined by GLC (Ref. 1221) and paper chromatography (Ref. 1229).	[1217] / [1219] / [1220] / [1221] / [1222] / [1226] / [1229]
187		4'-Apo-3,4-didehydrolycopene/ (4-Apo-3',4'-didehydrolycopene)	3,4-Didehydro-4'-apo-y,y-carotene	VCA1107	Shinichi Takaichi		C₃₅H₄₆	466.740									lmax (nm): HPLC eluent 465, 490, 527 (Ref. 1215)								an Escherichia coli transformant carrying the Erwinia uredovora crtE and crtI and Staphylococcus aureus crtM-mutant genes (Ref. 1215)			[1215]
188		4-Hydroxymyxol/ 4-OH-myxol/ (Aphanizophyll)	3',4'-Didehydro-1',2'-dihydro-b,y-carotene-3,4,1',2'-tetrol	VCA1108	Shinichi Takaichi		C₄₀H₅₆O₄	600.870			m.p. 172-173 C (glycoside) (Ref. 1223)						lmax (nm): methanol 444, 475, 507 (Ref. 1223)			MS (Ref. 1223)			Agricone of 4-OH myxol 2'-glycoside (aphanizophyll) in cyanobacteria. Aphanizomenon flos-aquae, Microcystis aeruginosa, Oscillatoria tenui and Anabaena aerulosa oscillatoriaoides (cyanobacteria) (Ref. 1223)				Since the name aphanizophyll can not specify the sugar moiety and the identification of the sugar moiety is unfeasible in many cyanobacteria, the following naming convention is proposed by (Ref. 1222) and S. Liaaen-Jensen: when the sugar moiety is unknown, the name is 4-hydroxymyxol 2'-glycoside, when known, as in the case of rhamnose, it should be named 4-hydroxymyxol 2'-rhamnoside.	[1222] / [1223]
189		4-Ketophleixanthophyll/ 1',2'-Dihydroxy-4-ketotoruelene	(2'S)-1'-b-D-glucopyranosyloxy-2'-hydroxy-3',4'-didehydro-1',2'-dihydro-b,y-caroten-4-one	VCA1109	Shinichi Takaichi		C₄₆H₆₄O₈	744.996										4-ketophleixanthophyll pentaacetate (Ref. 1227)	1H-NMR in CDCl3 (Ref. 1227)		CD in EPA (Ref. 1219)		Mycobacterium phlei (Mycobacteriaceae) (Ref. 1219/1227).					[1219] / [1227]
190		Salinixanthin/ 1',2'-Dihydroxy-4-ketotorulene 1'-glucoside ester	(2'S)-1'-[6-O-(13-Methyltetradecanoyl)-b-D-glycopyranosyloxy]-2'-hydroxy-3',4'-didehydro-1',2'-dihydro-b,y-caroten-4-one	VCA1110	Shinichi Takaichi		C₆₁H₉₂O₉	969.378									lmax (nm): acetone/MeOH (7:3) (453), 482, 508, %III/II=4; benzene (462), 493, 524, %III/II=9 (Ref. 1234)		1H-NMR in CDCl3/CD3OD (1:1) (Ref. 1234)	EI-MS (Ref. 1234)	CD in ethanol of salinixanthin and its tetraacetate (Ref. 1234)		Salinibacter ruber (halophilic eubacterium) (Ref. 1234)					[1234]
191		Salmoxanthin/ Trollixanthin	(3S,5R,6S,3'S,6'R)-5,6-Epoxy-5,6-dihydro-b,e-carotene-3,3',6'-triol	VCA1111	Shinichi Takaichi		C₄₀H₅₆O₄	600.870									lmax (nm): ether 416, 440, 470 (Ref. 1235)		1H-NMR in CDCl3 (Ref. 1235)		CD in EPA (Ref. 1235)		Oncorhynchus keta (salmon, fish) (Ref. 1235)					[1235]
192		Deepoxysalmoxanthin	(3R,3'S,6'R)-b,e-Carotene-3,3',6'-triol	VCA1112	Shinichi Takaichi		C₄₀H₅₆O₃	584.871									lmax (nm): ether (421), 444, 473 (Ref. 1235)		1H-NMR in CDCl3 (Ref. 1235)		CD in EPA (Ref. 1235)		Oncorhynchus keta (salmon, fish) (Ref. 1235)					[1235]
193		Gobiusxanthin/ 7,8-Didehydrodeepoxysalmoxanthin	(3R,3'S,6'R)-7,8-Didehydro-b,e-carotene-3,3',6'-triol	VCA1113	Shinichi Takaichi		C₄₀H₅₄O₃	582.855									lmax (nm): ether 420, 445, 475 (Ref. 1235/1329)			EIMS (Ref. 1329)	CD (Ref. 1329)		Oncorhynchus keta (salmon, fish) (Ref. 1235), Rhinogobius brunneus (freshwater goby, fish) (Ref. 1329).					[1235] / [1329]
194		3'-Hydroxy-3-keto-e-carotene/ 3'-OH-3-keto-e-carotene	(6R,3'R,6'R)-3'-Hydroxy-e,e-caroten-3-one	VCA1114	Shinichi Takaichi		C₄₀H₅₄O₂	566.856									lmax (nm): ether 417, 439, 468 (Ref. 0428)			MS (Ref. 0428). Negative CI-MS with methane (Ref. 1238).	CD in EPA (Ref. 0428)		e,e-Carotene-3,3'-dione and 3'-hydroxy-e,e-caroten-3-one are main pigments in feathers of Carduelis and Serinus (bird) (Ref. 1238). Small amounts of both carotenoids are found in hen's egg yolk, while lutein A is major (Ref. 0428). Eggs of Coryphaena hippurus (dolphin-fish) and Prognichthys agoo (flying fish) (Ref. 0408).		This may be produced from lutein in Carduelis and Serinus (bird)(Ref. 1238). This may be produced from lutein A in hen's egg (Ref. 0428). [Table 1001]		(6R,3'R,6'R) and (6S,3'R,6'R) forms are found in hen's egg yolk and are the same with the right half structure of lutein A (Ref. 0428).	[0408] / [0428] / [1238]
195		(6R,6'R)-3,3'-Diketo-e-carotene	(6R,6'R)-e,e-Carotene-3,3'-dione	VCA1115	Shinichi Takaichi		C₄₀H₅₂O₂	564.840									lmax (nm): ether 418, 440, 469 (Ref. 0428)			MS (Ref. 0428). Negative CI-MS with methane (Ref. 1238).	CD in EPA (Ref. 0428)		e,e-Carotene-3,3'-dione and 3'-hydroxy-e,e-caroten-3-one are main pigments in feathers of Carduelis and Serinus (bird) (Ref. 1238). Small amounts of both carotenoids are found in hen's egg yolk, while lutein A is major (Ref. 0428). Eggs of Coryphaena hippurus (dolphin-fish) and Prognichthys agoo (flying fish) (Ref. 0408).		This may be produced from lutein via 3'-hydroxy-e,e-caroten-3-one in Carduelis and Serinus (bird) (Ref. 1238). This may be produced from lutein A and zeaxanthin via 3'-hydroxy-e,e-caroten-3-one and 3-hydroxy-b,e-caroten-3'-one in heb's egg (Ref. 0428). [Table 1002]		(6S,6'S), (6S,6'R) and (6R,6'R) forms are found in hen's egg yolk (Ref. 0428).	[0408] / [0428] / [1238]
196		3'-Dehydrolutein/ Philosamiaxanthin/ 3-Hydroxy-b,e-caroten-3'-one	(3R,6'R)-3-Hydroxy-b,e-caroten-3'-one	VCA1116	Shinichi Takaichi		C₄₀H₅₄O₂	566.856									lmax (nm): ether 420, 444, 472 (Ref. 0428); hexane 267, 334, 421, 445, 472 (Ref. 0127); benzene 456-8, 486-7 (Ref. 1314); pet. ether 420, 444, 472 (Ref. 0408); HPLC eluent (424), 448, 476 (Ref. 1315)		1H-NMR (Ref. 0127>	MS (Ref. 0059/0127/0428)	CD in EPA (Ref. 0127/0428)		Small amounts of both (3R,6'R) and (3R,6'S) forms are found in hen's egg yolk, while lutein A is major (Ref. 0428). Eggs of Coryphaena hippurus (dolphin-fish) and Prognichthys agoo (flying fish) have (3R,6'S) form (Ref. 0408). Haemolymph of Philosamia cynthia pryeri (silkworm) (Ref. 1314). Flowers of Caltha palustris (Ref. 0127). Human and monkey retinas (Ref. 1315).		This may be produced from lutein A and zeaxanthin in hen's egg (Ref. 0428). [Table 1017]			[0059] / [0127] / [0408] / [0428] / [1314] / [1315]
197		a-Zeacarotene/ 7',8'-Dihydro-d-carotene	(6R)-7',8'-Dihydro-e,y-carotene	VCA1117	Shinichi Takaichi		C₄₀H₅₈	538.889																	In E. coli neurosporene background, lycopene e-cyclase from Arabidopsis produces a-zeacarotene (Ref. 1015).			[1015]
198		Prasinoxanthin	(3S,6R,3'R,6'R)-3,6,3'-Trihydroxy-7,8-dihydro-g,e-caroten-8-one	VCA1118	Shinichi Takaichi		C₄₀H₅₆O₄	600.870		A light-harvesting pigment-protein complex (LHC) of Pseudoscourfieldia marina (Micromonadophyceae = Pracinophyceae) contains 5 prasinoxanthin, 2 neoxanthin, 1 unknown carotenoid, 9 Chl b, 6 Chl a, 2 MgDV (mol) (Ref. 1136).							lmax (nm): ether 446 (466) (Ref. 1243); acetone (426), 449, (473); hexane (429), 452, (480) (Ref. 1246); acetone (427), 448, (468); CHCl3: 462 (Ref. 1247)	IR in KBr (Ref. 1243)	1H-NMR in CDCl3 (Ref. 1243/1245) 13C-NMR in CDCl3 (Ref. 1245)	(Ref. 0513/1243/1247)	CD in EPA (Ref. 1243) in ethanol (Ref. 0513)		Clone w 48-23 (Prasinophyceae) (Ref. 1243) Clones BT-5, 1326.1 and 266 G (Prasinophyceae) (Ref. 1244) Bathycoccus, Micromonas, Mantoniella, Pseudoscourfieldia and a clone IIA2 (Prasinophyceae) (Ref. 0513/1246/1247) Prasinococcus (Prasinophyceae) (Ref. 1248)				Identical with xanthophyll K. The hydroxy groups of the g-end group were shown to be cis-configutated (3S,6R) assuming 3S-chirality by 1H- and 13C-NMR (Ref. 1245).	[0513] / [1136] / [1243] / [1244] / [1245] / [1246] / [1247] / [1248]
199		Preprasinoxanthin	(3S,5R,6S,3'R,6'R)-5,6-Epoxy-3,3'-dihydroxy-5,6,7,8-tetrahydro-b,e-caroten-8-one	VCA1119	Shinichi Takaichi		C₄₀H₅₆O₄	600.870									lmax (nm): acetone 445, 466, %III/II=8; hexane (423), 447, 473, %III/II=29 (Ref. 1246)		1H-NMR in CDCl3 (Ref. 1246)	EI-MS (Ref. 1246)	CD in ethanol (Ref. 1246)		Clone IIA2 (Pracenophyceae) (Ref. 1246) Prasinococcus (Prasinophyceae) (Ref. 1248)					[1246] / [1248]
200		Micromonal	(3R,3'R,6'R)-3,3'-Dihydroxy-7',8'-dihydro-b,e-caroten-19'-al	VCA1120	Shinichi Takaichi		C₄₀H₅₆O₃	584.871									lmax (nm): acetone (423), 449, (472); diethylether (422), 447, (470); hexane (425), 449, (474); CHCl3 462, (483) (Ref. 1246/1247)		1H-NMR in CDCl3 (Ref. 1246)	EI-MS (Ref. 0513/1246/1247)	CD in ethanol (Ref. 1246)		Bathycoccus, Micromonas, Mantoniella and Pseudoscourfieldia (Prasinophyceae) (Ref. 0513/1246/1247)					[0513] / [1246] / [1247]
201		Uriolide	(3S,5R,6S,3'R,6'R)-5,6-Epoxy-3,3'-dihydroxy-5,6,7',8'-tetrahydro-b,e-caroten-19',11'-olide	VCA1121	Shinichi Takaichi		C₄₀H₅₄O₅	614.854									lmax (nm): acetone 448, 472, %III/II=11; methanol 448, 470, %III/II=2; hexane (427), 448, 478, %III/II=38 (Ref. 1244); CHCl3 (433), 462, 483, %III/II=1 (Ref. 1247)		1H-NMR in CDCl3 (Ref. 1244)	(Ref. 0513/1244/1247)	Cd in EPA (Ref. 1244)		Clone 266 G (Prasinophyceae) (Ref. 1244) Bathycoccus (Prasinophyceae) (Ref. 1247) Micromonas, Mantoniella and Pseudoscourfieldia (Prasinophyceae) (Ref. 0513) Prasinococcus (Prasinophyceae) (Ref. 1248)					[0513] / [1244] / [1247] / [1248]
202		6'-Hydroxysiphonaxanthin/ 6'-OH-Siphonaxanthin	(3R,3'R,6'?)-3,19,3',6'-Tetrahydroxy-7,8-dihydro-b,e-caroten-8-one	VCA1122	Shinichi Takaichi	OH-Sx	C₄₀H₅₆O₅	616.870									lmax (nm): acetone 442, (463); CHCl3 461 (Ref. 1248)		1H-NMR in CDCl3 (Ref. 1248)	EI-MS (Ref. 1248)			Pyramimonas (Pracenophyceae) (Ref. 1248)				Identical with xanthophyll K2S.	[1248]
203		6'-Hydroxysiphonaxanthin ester/ 6'-OH-siphonaxanthin/ 6'-Hydroxysiphonaxanthin dodecenoate	(3R,3'R,6'?)-19-(trans-Dodec-2-enoyloxy)-3,3',6'-trihydroxy-7,8-dihydro-b,e-caroten-8-one	VCA1123	Shinichi Takaichi	OH-Sx-FA	C₅₂H₇₆O₆	797.156		6'-Hydroxysiphonaxanthin ester and siphonaxanthin ester have function as antenna pigments in Pterosperma (Ref. 1249).							lmax (nm): acetone 449, (466); methanol 452, (465); heptane 452, (478); CHCl3 463 (Ref. 1248); methanol 455 and its reduced form 402, 425, 451, %III/II=93 (Ref. 1249)		1H-NMR in CDCl3 (Ref. 1248) 1H- and 13C-NMR in CDCl3 (Ref. 1249)	EI-MS (Ref. 1248); FD-MS 824 for C14:1 (Ref. 1249)		HPLC of Pterosperma cristatum (Ref. 1249), and Nephroselmis astigmatica, N. phriformis and Nephroselmis sp. MBIC 11158 (Ref. 1352) (Prasinophyceae, Chlorophyta).	Pyramimonas (Ref. 1248), Pterosperma (Ref. 1249), Nephroselmis (Ref. 1352) (Prasinophyceae).				Identical with xanthophyll K2. Pyraminonas amylifera has 2-trans-dodecenoate and 2-trans-decenoate as esterified fatty acids (Ref. 1248). Pterosperma cristatum has 2-trans-tetradecenoate as esterified fatty acid (Ref. 1249). Nephroselmis astigmatica, N. phriformis and Nephroselmis sp. MBIC 11158 have OH-Sx-C12:1 and C14:1 esters (Ref. 1352)	[1248] / [1249] / [1352]
204		Neurosporaxanthin	4'-Apo-b,y-caroten-4'-oic acid	VCA1124	Shinichi Takaichi		C₃₅H₄₆O₂	498.739									lmax (nm): diethylether 475 (Ref. 1253)		1H- and 13C-NMR in CDCl3 (Ref. 1253)	EI-MS, HR-EI-MS (Ref. 1253) (Ref. 0059)			Neurospora crassa (Ref. 1176), Fusarium fujikuroi (previous name, Gibberella fujikuroi) (Ref. 1175), and Fusarium strain T-1 (Ref. 1253) (fungus).					[0059] / [1175] / [1176] / [1253]
205		Neurosporaxanthin b-D-glucopyranoside	4'-Apo-b-caroten-4'-oic acid b-D-glucopyranoside	VCA1125	Shinichi Takaichi		C₄₁H₅₆O₇	660.879									lmax (nm): diethylether 475 (Ref. 1253)		1H-NMR in CDCl3/CD3OD (4:1) (Ref. 1253)	FAB-MS, HR-FAB-MS (Ref. 1253)			Fusarium strain T-1 (fungus) (Ref. 1253).					[1253]
206		Bixindial/ Bixin aldehyde	6,6'-Diapocarotene-6,6'-dial	VCA1126	Shinichi Takaichi		C₂₄H₂₈O₂	348.478															Seeds of Bixa orellana (plant) (Ref. 1254).			Lycopene is cleavaged to bixindial by lycopene cleavage dioxygenase (BoLCD), and bixindial is oxidized to norbixin by bixin aldehyde dehydrogenase (BoBADH) with NAD in Bixa orellana seeds (plant) (Ref. 1254). [Table 1035]		[1254]
207		Norbixin	6,6'-Diapocarotene-6,6'-dioic acid	VCA1127	Shinichi Takaichi		C₂₄H₂₈O₄	380.477															Seeds of Bixa orellana (plant) (Ref. 1254).			Bixindial is oxidized to norbixin by bixin aldehyde dehydrogenase (BoBADH) with NAD, and norbixin is methylated to bixin and methyl bixin by norbixin methyltransferase (BonBMT) with S-adenosylmethionine in Bixa orellana seeds (plant) (Ref. 1254). [Table 1036]		[1254]
208		Bixin	6-Methyl hydrogen 6,6'-diapocarotene-6,6'-dioate	VCA1128	Shinichi Takaichi		C₂₅H₃₀O₄	394.503									[Spectrum 1153]			FD-MS m/z=394 (Ref. 1053)			Seeds of Bixa orellana (plant) (Ref. 1254).			Norbixin is methylated to bixin and methyl bixin by norbixin methyltransferase (BonBMT) with S-adenosylmethionine in Bixa orellana seeds (plant) (Ref. 1254). [Table 1037]	Bixin, also known as annatto, is a seed-specific pigment widely used in foods and cosmetics since pre-Columbian times. Natural bixin is 9'-cis form.	[1053] / [1254]
209		Methyl bixin/ (Bixin dimethyl ester)	Dimethyl 6,6'-diapocarotene-6,6'-dioate	VCA1129	Shinichi Takaichi		C₂₆H₃₂O₄	408.530												FD-MS m/z=408 (Ref. 1053)			Seeds of Bixa orellana (plant) (Ref. 1254).			Norbixin is methylated to bixin and methyl bixin by norbixin methyltransferase (BonBMT) with S-adenosylmethionine in Bixa orellana seeds (plant) (Ref. 1254). [Table 1038]		[1053] / [1254]
210		Dihydroxyneurosporene/ OH-Chloroxanthin	1,2,7,8,1',2'-Hexahydro-y,y-carotene-1,1'-diol	VCA1130	Shinichi Takaichi		C₄₀H₆₂O₂	574.919									lmax (nm): HPLC eluent 415, 440, 470 (Ref. 1255)								Chloroxanthin is changed to dihydroxyneurosporene by CrtC from Rvi. gelatinosus, not by that from Rba. capusulatus (Ref. 1255).			[1255]
211		OH-Demethylspheroidene/ Hydroxydemethylspheroidene	3,4-Didehydro-1,2,1',2',7',8'-hexahydro-y,y-carotene-1,1'-diol	VCA1131	Shinichi Takaichi	OH-DMS	C₄₀H₆₀O₂	572.903									lmax (nm): HPLC eluent 430, 455, 485 (Ref. 1255)			FD-MS m/z=572 (Ref. 1260)					Demethylspheroidene is changed to OH-demethylshperoidene by CrtC from Rvi. gelatinosus, not by that from Rba. capusulatus (Ref. 1255).	The crtA and crtF mutant of Rubrivivax gelatinosus (photosynthetic bacteria) produces this carotenoid (Ref. 1260).		[1255] / [1260]
212		Astaxanthin ester/ Astaxanthin monoester/ Astaxanthin diester	3,3'-Dihydroxy-b,b-carotene-4,4'-dione monoester and diester	VCA1132	Shinichi Takaichi															FD-MS 778 (C12:0), 806 (C14:0), 832 (C16:1), 834 (C16:0), 860 (C18:1); FAB-MS, SI-MS (Ref. 1256)			Euphausia superba (Antarctic krill) (Ref. 1256) Euphausia, Thysanoessa, Calanus, Acanthephyra and Cancer (Crustaceans) (Ref. 1257)				Composition of astaxanthin, its monoester and its diester in krill are 20%, 34% and 46% (Ref. 1256), and 7-8%, 25-27% and 62-64% (Ref. 0422). Those in Euphausia, Thysanoessa, Calanus, Acanthephyra and Cancer (Crustaceans) are also reported (Ref. 1257). Only five kinds of fatty acids are found in astaxanthin monoester and diester in krill: C12:0 (17%), C14:0 (20%), C16:0 (29%), C16:1 (9%) and C18:1 (25%) in monoester (Ref. 1256). Almost the same stereochemical composition in astaxanthin, its monoester and its diester in keill are found: 62-71% (3R,3'R)-, 11-14% (3R,3'S; meso)- and 17-26% (3S,3'S)-astaxanthin (Ref. 0422).	[0422] / [1256] / [1257]
213		Phillipsiaxanthin/ 1,1'-(OH)₂-2,2'-diketo-3,4,3',4'-tetradehydrolycopene	1,1'-Dihydroxy-3,4,3',4'-tetradehydro-1,2,1',2'-tetrahydro-y,y-carotene-2,2'-dione	VCA1133	Shinichi Takaichi		C₄₀H₅₂O₄	596.838												FD-MS m/z=596 (Ref. 1260)						The crtF mutant of Rubrivivax gelatinosus (photosynthetic bacteria) produces this carotenoid (Ref. 1260).		[1260]
214		Ketotetradehydrolycopene/ 1,1'-(OH)₂-2-keto-3,4,3',4'-tetradehydrolycopene	1,1'-Dihydroxy-3,4,3',4'-tetradehydro-1,2,1',2'-tetrahydro-y,y-caroten-2-one	VCA1134	Shinichi Takaichi		C₄₀H₅₄O₃	582.855												FD-MS m/z=582 (Ref. 1260)						The crtF mutant of Rubrivivax gelatinosus (photosynthetic bacteria) produces this carotenoid (Ref. 1260).		[1260]
215		OH-Demethylspheroidenone/ Hydroxydemethylspheroidenone	1,1'-Dihydroxy-3,4-didehydro-1,2,1',2',7',8'-hexahydro-y,y-caroten-2-one	VCA1135	Shinichi Takaichi	OH-DMSO	C₄₀H₅₈O₃	586.887												FD-MS m/z=586 (Ref. 1260)						The crtF mutant of Rubrivivax gelatinosus (photosynthetic bacteria) produces this carotenoid (Ref. 1260).		[1260]
216		1,2-Dihydroneurosporene	1,2,7,8-Tetrahydro-y,y-carotene	VCA1136	Shinichi Takaichi		C₄₀H₆₀	540.904		Rps. viridis reaction center contains one 15-cis 1,2-dihydroneurosporene, better than the original model with 13-cis form (Ref. 1263).							lmax (nm): light petroleum 414, 439, 468 (Ref. 1261/1262); acetonitrile/methanol/THF (58:35:7) 267, 331, 417, 441, 470, %III/II=89 [Spectrum 1023] (Ref. 1057)		1H-NMR 0.88, J=6 (Ref. 1261)	AEI-MS m/z=540 (Ref. 1261/1262)		HPLC (column; Novapak C18 (Waters) 8 X 100 mm: eluelnt; acetonitrile/methanol/THF 58:35:7: flow 2.0 ml/min) Rt=15.3 min (Ref. 1057)	Rhodopseudomonas viridis (present name, Blastochloris viridis) (photosynthetic bacterium) (Ref. 1261/1262)				Composition is neurosporene (3%), 1,2-dihydroneurosporene (72%), lycopene (1%), 1,2-dihydrolycopene (17%), 1,2-dihydro-3,4-dehydrolycopene (5%) and others (2%) in Rps. viridis (Ref. 1262).	[1057] / [1261] / [1262] / [1263]
217		1,2-Dihydrolycopene	1,2-Dihydro-y,y-carotene	VCA1137	Shinichi Takaichi		C₄₀H₅₈	538.889									lmax (nm): light petroleum 444, 470, 502 (Ref. 1261/1262); acetonitrile/methanol/THF (58:35:7) 294, 363, 446, 473, 503, %III/II=72 [Spectrum 1024] (Ref. 1057)		1H-NMR 0.88, J=6 (Ref. 1261)	AEI-MS m/z=538 (Ref. 1261/1262)		HPLC (column; Novapak C18 (Waters) 8 X 100 mm: eluelnt; acetonitrile/methanol/THF 58:35:7: flow 2.0 ml/min) Rt=14.2 min (Ref. 1057)	Rhodopseudomonas viridis (present name, Blastochloris viridis) (photosynthetic bacterium) (Ref. 1261/1262), nicotin-inhibited culture of Chlorobium (present name, Chlorobaculum) tepidum (Ref. 1103).					[1057] / [1103] / [1261] / [1262]
218		1,2-Dihydro-3,4-dehydrolycopene	3,4-Didehydro-1,2-dihydro-y,y-carotene	VCA1138	Shinichi Takaichi		C₄₀H₅₆	536.873									lmax (nm): light petroleum 457, 483, 518 (Ref. 1261/1262); acetonitrile/methanol/THF (58:35:7) 306, 375, 458, 484, 517, %III/II=69 [Spectrum 1025] (Ref. 1057)			AEI-MS m/z=536 (Ref. 1261/1262)		HPLC (column; Novapak C18 (Waters) 8 X 100 mm: eluelnt; acetonitrile/methanol/THF 58:35:7: flow 2.0 ml/min) Rt=12.5 min (Ref. 1057)	Rhodopseudomonas viridis (present name, Blastochloris viridis) (photosynthetic bacterium) (Ref. 1261/1262)					[1057] / [1261] / [1262]
219		1,2,1',2'-Tetrahydrolycopene	1,2,1',2'-Tetrahydro-y,y-carotene	VCA1139	Shinichi Takaichi		C₄₀H₆₀	540.904									lmax (nm): light petroleum 444, 470, 502 (Ref. 1262); acetonitrile/methanol/THF (58:35:7) 294, 361, 447, 471, 502, %III/II=74 (Ref. 1057)		13C-NMR in CDCl3 (Ref. 0061)	AEI-MS m/z=540 (Ref. 1262)		HPLC (column; Novapak C18 (Waters) 8 X 100 mm: eluelnt; acetonitrile/methanol/THF 58:35:7: flow 2.0 ml/min) Rt=17.7 min (Ref. 1057)	Rhodopseudomonas viridis (present name, Blastochloris viridis) (photosynthetic bacterium) (Ref. 1262), nicotin-inhibited culture of Chlorobium (present name, Chlorobaculum) tepidum (Ref. 1103).					[0061] / [1057] / [1103] / [1262]
220		Crocetindial/ Crocetin dialdehyde	8,8'-Diapocarotene-8,8'-dial	VCA1140	Shinichi Takaichi		C₂₀H₂₄O₂	296.403									lmax (nm): hexane 405, 430, 458 (Ref. 1264); benzene 444, 473; petrol ether 427, 455; ethanol 443 (Ref. 1266)		13C-NMR in CDCl3 (Ref. 0061)	M⁺=296 (Ref. 1264/1266) (Ref. 0059)			Crocus (Crocus sativus, plant) (Ref. 1264)		b-Carotene is cleaved to crocetindial and b-cyclocitral, and zeaxanthin is to crocetindial and hydroxy-b-cyclocitral by b-carotene 7,8(7',8') oxygenase of Microcystis (cyanobacterium) by freezing the cell pellet. The enzyme requires O₂ and iron, but is sensitive to sulfhydryl reagents, antioxidants and chelation reagents, and is membrane bound (Ref. 1266).	Zeaxanthin is changed to one crocetindial and two hydroxy-b-cyclocitral by zeaxanthin 7,8(7',8')-cleavage dioxygenase (CsZDS) from crocus chromoplast (Ref. 1264).		[0059] / [0061] / [1264] / [1266]
221		Crocetin	8,8'-Diapocarotene-8,8'-dioic acid	VCA1141	Shinichi Takaichi		C₂₀H₂₄O₄	328.402															Crocus (Crocus sativus, plant) (Ref. 1264)					[1264]
222		OH-Diaponeurosporene glucoside ester	5-[(6-O-Acyl-b-D-glucopyranosyl)oxy]-5,6,7,8-tetrahydro-4,4'-diapocarotene	VCA1142	Shinichi Takaichi														1H- and 13C-NMR in CDCl3 (Ref. 1270)	FD-MS for C16:0, 820; C16:1, 818 (Ref. 1270)			Alkaliphilic heliobacteria of the genus Heliorestis, H. daurensis, H. baculata and an undescribed species heliorestis strain HH (heliobacteria) (Ref. 1270)				Carotenoid compositions are 30-40 mol% 4,4'-diaponeurosporene, 10-20 mol% OH-diaponeurosporene glucoside C16:1 ester, and 40-50 mol % OH-diaponeurosporene glucoside C16:0 ester in three Heliorestis (Ref. 1270).	[1270]
223		Phleixanthophyll/ Deoxymyxol 1'-glucoside	(2'S)-1'-(b-D-Glucopyranosyloxy)-3',4'-didehydro-1',2'-dihydro-b,y-caroten-2'-ol	VCA1143	Shinichi Takaichi		C₄₆H₆₆O₇	731.012			m.p. 209 C (Ref. 1227)							phleixanthophyll (Ref. 1227)	1H-NMR in CDCl3 of phleixanthophyll (Ref. 1227)		CD in EPA of deoxymyxol 2'-dimethyl fucoside and phleixanthophyll (Ref. 1222) are the mirror image of that of (2'R)-plectaniaxanthin (Ref. 1219/1225).		The structure of phleixanthophyll from Mycobacterium phlei is (2'S)-deoxymyxol 1'-(b-D-glucoside) (Ref. 1219/1227).				Note: Although deoxymyxol from cyanobacteria and aglycon of phleixanthophyll from Mycobacterium phlei have the same structure including stereochemistry, the glycosilated positions are 2'-OH and 1'-OH, respectively. Although deoxymyxol and plectaniaxanthin have the same structure, the stereochemistry of 2'-OH is (2'S) and (2'R), respectively.	[1219] / [1222] / [1225] / [1227]
224		1',2'-Dihydroxy-4-ketotoruelene/ Deoxyketomyxol/ 3-Deoxy-2'-hydroxyflexixanthin	(2'S)-1',2'-dihydroxy-3',4'-didehydro-1',2'-dihydro-b,y-caroten-4-one	VCA1144	Shinichi Takaichi		C₄₀H₅₄O₃	582.855			mp 204 (Ref. 1281)						lmax (nm): hexane 314, 474, 500 (Ref. 1281)		1H, 13C-NMR in CDCl3(Ref. 1281)	MS m/z 582 (Ref. 1281)	CD in EPA (Ref. 1281)		(2'S)-Form is the carotenoid moiety of 4-ketophleixanthophyll and salinixanthin. (2'R)-3-Deoxy-2'-hydroxyflexixanthin from Taxeobacter (gliding bacteria) (Ref. 1281)	(2'R)-3-Deoxy-2'-hydroxyflexixanthin(Ref. 1144)				[1144] / [1281]
225		4-Hydroxyzeaxanthin	(3S,4R,3'R)-b,b-Carotene-3,4,3'-triol	VCA1145	Shinichi Takaichi		C₄₀H₅₆O₃	584.871									(Ref. 1296/1297/1298)		(3S,4R,3'R)-b,b-Carotene-3,4,3'-triol and (3S,4S,3'R) form (Ref. 1296/1297/1298)	(Ref. 1296/1297/1298)	CD (Ref. 1296)		Minor carotenoid in six species of chitons (Ref. 1296). Gudgeon, Pseudogobio esocinus (Crpriniformes) (Ref. 1298). Folkatal bulhead (Siluriformes), coho salmon and dog salmon (Salmoniformes) (Ref. 1297).		This might be an intermediate from zeaxanthin to astaxanthin (Ref. 1298). Since mixtures of (3S,4R,3'R) and (3S,4S,3'R) forms are found in folkatal bulhead, coho salmon and dog salmon, these might be intermediates in the reductive metabolic pathway from (3S,3'S)-astaxanthin to (3R,3'R)-zeaxanthin (Ref. 1297).			[1296] / [1297] / [1298]
226		4-Hydroxylutein	(3S,4R,3'R,6'R)-b,e-Carotene-3,4,3'-triol	VCA1146	Shinichi Takaichi		C₄₀H₅₆O₃	584.871									(Ref. 1296)		(3S,4R,3'R,6'R)-b,e-Carotene-3,4,3'-triol and (3S,4S,3'R,6'R) form (Ref. 1296), (3S,4R,3'S,6'R) form (Ref. 1299)	(Ref. 1296)	CD (Ref. 1296), (3S,4R,3'S,6'R) form (Ref. 1299)		Minor carotenoid in six species of chitons (Ref. 1296). (3S,4R,3'S,6'R) form from Carassius auratus (goldfish) (Ref. 1299).					[1296] / [1299]
227		Crustaxanthin/ 4,4'-Dihydroxyzeaxanthin	(3S,4R,3'S,4'R)-b,b-Carotene-3,4,3',4'-tetrol	VCA1147	Shinichi Takaichi		C₄₀H₅₆O₄	600.870									(Ref. 1298)		(Ref. 1298)	(Ref. 1298)			Gudgeon, Pseudogobio esocinus (Crpriniformes) (Ref. 1298). Coho salmon and dog salmon (Salmoniformes) (Ref. 1297).		This might be an intermediate from zeaxanthin to astaxanthin (Ref. 1298). Since mixtures of (3S,4R,3'S,4'R), (3S,4S,3'S,4'R) and (3S,4S,3'S,4'S) forms are found in coho salmon and dog salmon, these might be intermediates in the reductive metabolic pathway from (3S,3'S)-astaxanthin to (3R,3'R)-zeaxanthin (Ref. 1297).		Stereochemistry of hydroxy groups in crustaxanthin is mostly not determined.	[1297] / [1298]
228		Aaptopurpurin	3-Methoxy-b,c-carotene	VCA1148	Shinichi Takaichi		C₄₁H₅₄O	562.867			138-140 C (Ref. 1303)						lmax (nm): petroleum ether 436, 458, 478 (Ref. 1303)		(Ref. 1303)	CDCl3 (Ref. 1303)			Aaptos aaptos (sea sponge) (Ref. 1303)				The chirality at C3 was not established.	[1303]
229		Dehydroophioxanthin	Disodium 3,3'-dihydroxy-7,8-didehydro-5,6,5',6'-tetrahydro-b,b-carotene-4,4'-diyl disulphate	VCA1149	Shinichi Takaichi		C₄₀H₅₆O₁₀S₂Na₂	806.978									lmax (nm): methanol 410, 432, 461 (Ref. 1308)	(Ref. 1308)	1H-NMR (Ref. 1308)	FAB-MS (Ref. 1308)			A minor carotenoid of Ophiocomina nigra (ophiuroid) (Ref. 1308).					[1308]
230		Ophioxanthin	Disodium 3,3'-dihydroxy-5,6,5',6'-tetrahydro-b,b-carotene-4,4'-diyl disulphate	VCA1150	Shinichi Takaichi		C₄₀H₅₈O₁₀S₂Na₂	808.994									lmax (nm): methanol 415 (e=46640), 435 (56320), 465 (48960) (Ref. 1307)	(Ref. 1307)	1H-, 13C-NMR (CD3OD) (Ref. 1307)				A minor carotenoid of Ophioderma longicaudum (Ref. 1307) and Ophiuroid ophiocomina nigra (ophiuroid) (Ref. 1308)					[1307] / [1308]
231		Bastaxanthin D/ Bastaxanthol	Sodium (3R,1'R,3'R,5'R)-19,3',17'-trihydrooxy-6'-oxo-7,8-didehydro-b,k-caroten-3-yl sulphate	VCA1151	Shinichi Takaichi		C₄₀H₅₃O₈SNa	716.900									lmax (nm): acetone (360), 468, (490); methanol 468, (490) (Ref. 1305)	(Ref. 1305)	1H-NMR (CD3OD, CDCl3) (Ref. 1305)	(Ref. 1305)	CD (CD3OD) (Ref. 1305)		Ianthella basta (marine sponge) (Ref. 1305/1306)					[1305] / [1306]
232		Bastaxanthin C/ Bastaxanthin	Sodium (3R,1'R,5'R)-19,17'-dihydrooxy-3',6'-dioxo-7,8-didehydro-b,k-caroten-3-yl sulphate	VCA1152	Shinichi Takaichi		C₄₀H₅₁O₈SNa	714.884			190 C (Ref. 1306)						lmax (nm): methanol 360, 474; acetone 474 (Ref. 1306)	(Ref. 1306)	1H-, 13C-NMR (CD3OD) (Ref. 1306)	(Ref. 1306)	CD (methanol) (Ref. 1306)		Ianthella basta (marine sponge) (Ref. 1305/1306)					[1305] / [1306]
233		Fucoxanthinol 3'-sulphate	Sodium (3S,5R,6R,3'S,5'R,6'S)-5',6'-epoxy-5,3'-dihydroxy-8'-ono-6,7-didehydro-5,6,5',6',7',8'-hexahydro-b,b-caroten-3-yl sulphate	VCA1153	Shinichi Takaichi		C₄₀H₅₅O₈SNa	718.916									lmax (nm): HPLC eluent 456 (Ref. 1309)		1H-NMR (CD3OD) (Ref. 1309)	(Ref. 1309)			Isolated from egg yolks from laying hens fed a brown algae (Ref. 1309).		In lying hens, fucoxanthin in Fucus serratus (brown algae) is metabolized to fucoxanthinol, and then fucoxanthinol 3'-sulphate and paracentrone (Ref. 1309).			[1309]
234		Renieratene	f,c-Carotene	VCA1154	Shinichi Takaichi		C₄₀H₄₈	528.809			184-185 C (Ref. 1317/1331)						lmax (nm): benzene 457, 476, 507; CS2 467, 497, 532 (Ref. 1316); 463, 495, 532 (Ref. 1317)		(Ref. 1316)				A major carotenoid of Reniera japonica (sea sponge) (Ref. 1317)	(Ref. 1316/1331)				[1316] / [1317] / [1331]
235		Renierapurpurin	c,c-Carotene	VCA1155	Shinichi Takaichi		C₄₀H₄₈	528.809			229-230 C (Ref. 1317/1331)						lmax (nm): benzene 464, 487, 519; CS2 477, 504, 544 (Ref. 1316); CS2 475, 504, 544 (Ref. 1317/1331)	(Ref. 1331)	(Ref. 1316)				A major carotenoid of Reniera japonica (sea sponge) (Ref. 1317)	(Ref. 1316/1331)				[1316] / [1317] / [1331]
236		Vaucheriaxanthin	(3S,5R,6R,3'S,5'R,6'S)-5',6'-Epoxy-6,7-didehydro-5,6,5',6'-tetrahydro-b,b-carotene-3,5,3',19'-tetrol	VCA1156	Shinichi Takaichi		C₄₀H₅₆O₅	616.870									lmax (nm): ethanol 418, 436, 466 (Ref. 1318)	(Ref. 1318)	(Ref. 1318)	(Ref. 1318)	CD (E.S. Egeland)		Free and esterified forms from Nannochloropsis salina (Eustigmatophyceae alga) (E.S. Egeland), and only esterified form from Vaucheria terrestris (Xanthophyceae alga) (S. Takaichi) after saponification.				Free form may be released from the natural esters by saponification. Some studies reported the location of the primary hydroxy group at C-19, but this has been revised at C-19' (Ref. 1318).	[1318]
237		Vaucheriaxanthin 3-acetate 19'-octanoate	(3S,5R,6S,3'S,5'R,6'R)-5,6-Epoxy-3'-ethanoyloxy-19-octanoyloxy-6',7'-didehydro-5,6,5',6'-tetrahydro-b,b-carotene-3,5'-diol	VCA1157	Shinichi Takaichi		C₅₀H₇₂O₇	785.102									lmax (nm): acetone 422, 445, 472, %III/II=33 (E.S. Egeland)			FD-MS: 784 (Takaichi Shinichi), MS: 784 and 812 (E.S. Egeland)			Free and esterified forms from Nannochloropsis salina (Eustigmatophyceae alga) (E.S. Egeland), and only esterified form from Vaucheria terrestris (Xanthophyceae alga) (S. Takaichi) after saponification.				Free form may be released from the natural esters by saponification. The natural esters from Nannochloropsis salina are 3-acetate 19'-octanoate and 3-acetate 19'-decanoate in the ratio 7:3 (E.S. Egeland). That from Vaucheria terrestris is acetate octanoate, whose attached hydroxy groups are not deternined (S. Takaichi).
238		Zeinoxanthin/ (a-Cryptoxanthin)	(3R,6'R)-b,e-caroten-3-ol	VCA1158	Shinichi Takaichi		C₄₀H₅₆O	552.872			179-181 C						lmax (nm): hexane 267, 335, 422, 445, 474 (Ref. 0127)		(Ref. 0127)	(Ref. 0127)	CD (Ref. 0127)		Zeinoxanthin is a very rare carotenoid. Flowers of Caltha palustris (Magnoliatae, Ranunclales) (Ref. 0127).		Lutein A is produced via a-cryptoxanthin (LUT1, CrtR-e) or zeinoxanthin (CrtR-b) from a-carotene. The LUT1 (CrtR-e) mutant of Arabidopsis accumulates zeinoxanthin (Ref. 1280).	The LUT1 (CrtR-e) from Arabidopsis is the e-carotene hydroxylase belong to the cytochrome P450-type monooxygenase (Ref. 1280).		[0127] / [1280]
239		a-Cryptoxanthin	(3'R,6'R)-b,e-caroten-3'-ol	VCA1159	Shinichi Takaichi		C₄₀H₅₆O	552.872									lmax (nm): petrol 420, 444, 473, %III/II=73 (Ref. 0079)		(Ref. 0079)	(Ref. 0079)	CD (Ref. 0079)		A minor carotenoid from Antithamnion plumula and Ceramium rubrum (Rhodophyceae, red algae) (Ref. 0079)		Lutein A is produced via a-cryptoxanthin (LUT1, CrtR-e) or zeinoxanthin (CrtR-b) from a-carotene.			[0079]
240		Lycopen-20-ol/ Lycopenol/ (Anhydrowarmingol)	13-cis-y,y-Caroten-20-ol	VCA1160	Shinichi Takaichi		C₄₀H₅₆O	552.872									lmax (nm): petroleum ether 345, 362, 440, 466, 495 (Ref. 1320)						Lycopenol contents is Thiocystis violacea 2311 (4%) and Lamprocystis roseopersicina 3012 (27%) (purple photosynthetic bacteria), while rhodopinal is a mojor carotneoid (Ref. 1054/1320).					[1054] / [1320]
241		Lycopen-20-al/ Lycopenal/ (Anhydrowarmingone)	13-cis-y,y-Caroten-20-al	VCA1161	Shinichi Takaichi		C₄₀H₅₄O	550.856												(Ref. 1321)			Lycopenal is a minor carotenoid (1-10%) in 6 species of purple photosynthetic bacteria, such as Rhodocyclus purpureu and Thiodictyon bacillosum, while rhodopinal is a major one (Ref. 1054).					[1054] / [1321]
242		Rhodopinol	13-cis-1,2-Dihydro-y,y-carotene-1,20-diol	VCA1162	Shinichi Takaichi		C₄₀H₅₈O₂	570.887									lmax (nm): petroleum ether 345, 362, 445, 471, 503 (Ref. 1320)			(Ref. 1321)			Rhodopinol is a minor carotenoid (3-36%) in 9 species of purple photosynthetic bacteria, such as Rhodocyclus purpureu and Thiodictyon elegans, while rhodopinal is a major one (Ref. 1054/1320).					[1054] / [1320] / [1321]
243		Rhodopin-20-al/ Rhodopinal/ (Warmingone)	13-cis-1-Hydroxy-1,2-dihydro-y,y-caroten-20-al	VCA1163	Shinichi Takaichi		C₄₀H₅₆O₂	568.871									lmax (nm): petroleum ether 345, 362, 498 (Ref. 1320)			(Ref. 1321)			Rhodopinal is a major carotenoid in 9 species of purple photosynthetic bacteria (Ref. 1054/1320).					[1054] / [1320] / [1321]
244		Rhodopinol glucoside	13-cis-1-Glucopyranosyloxy-1,2-dihydro-y,y-caroten-20-ol	VCA1164	Shinichi Takaichi		C₄₆H₆₈O₇	733.028									The same absorption spectrum with rhodopin (S. Takaichi).						Rhodopseudomonas acidophilla strain 7050 (present name: Rhodoblastus acidophilus; purple photosynthetic bacterium): high light culture (160 mmols/s/m²); rhodopin glucoside 34%, low light culture (10 mmols/s/m²); rhodopinal 5%, rhodopin goucoside 1%, rhodopinol glucoside 7% and rhodopinal glucoside 61% (Ref. 1054).					[1054]
245		Rhodopin-20-al glucoside/ Rhodopinal glucoside	13-cis-1-Glucopyranosyloxy-1,2-dihydro-y,y-caroten-20-al	VCA1165	Shinichi Takaichi		C₄₆H₆₆O₇	731.012									The same absorption spectrum with rhodopinal (S. Takaichi).						Rhodopseudomonas acidophilla strain 7050 (present name: Rhodoblastus acidophilus; purple photosynthetic bacterium): high light culture (160 mmols/s/m²); rhodopin glucoside 34%, low light culture (10 mmols/s/m²); rhodopinal 5%, rhodopin goucoside 1%, rhodopinol glucoside 7% and rhodopinal glucoside 61% (Ref. 1054).					[1054]
246		3,4,3',4'-Tetrahydrospirilloxanthin-20-al/ Tetrahydrospirilloxanthinal	13-cis-1,1'-Dimethoxy-1,2,1',2'-tetrahydro-y,y-caroten-20-al	VCA1166	Shinichi Takaichi		C₄₂H₆₂O₃	614.940												(Ref. 1321)			A minor carotenoid of Thiococcus (=Thiocapsa) pfennigii (Ref. 1054/1319).					[1054] / [1319] / [1321]
247		Methoxylycopenal	13-cis-1-Methoxy-1,2-dihydro-y,y-caroten-20-al	VCA1167	Shinichi Takaichi		C₄₁H₅₈O₂	582.898									lmax (nm): petroleum ether 345, 362, 498 (Ref. 1320)			(Ref. 1321)			A major carotenoid of Lamprocystis roseopersicina 3012 (Ref. 1054/1320).					[1054] / [1320] / [1321]
248		Lycoxanthin/ Lycopen-16-ol	y,y-Caroten-16-ol	VCA1168	Shinichi Takaichi		C₄₀H₅₆O	552.872			173-174 C						lmax (nm): acetone 448, 476, 508 (Ref. 1322); acetone 448, 474, 505; petroleum ether 443, 469, 500 (Ref. 1324)	(Ref. 1322/1324)	(Ref. 1322/1323/1324)	(Ref. 0059/1324)			Ripe berries of Solanum dulcamara (Ref. 1322/1323)	(Ref. 1324)			Lycoxanthin is a rare carotenoid, while rhodopin is found in purple photosynthetic bacteria.	[0059] / [1322] / [1323] / [1324]
249		Lycophyll/ Lycopene-16,16'-diol	y,y-Carotene-16,16'-diol	VCA1169	Shinichi Takaichi		C₄₀H₅₆O₂	568.871			191 C						lmax (nm): acetone (420)m 447, 473.5, 504.5 (Ref. 1324)	(Ref. 1322/1324)	(Ref. 1323/1324)	(Ref. 0059/1324)			Ripe berries of Solanum dulcamara (Ref. 1322/1323)	(Ref. 1324)				[0059] / [1322] / [1323] / [1324]
250		Okenone	1'-Methoxy-1',2'-dihydro-c,y-caroten-4'-one	VCA1170	Shinichi Takaichi		C₄₁H₅₄O₂	578.866		The energy transfer from okenone to bacteriochlorophyll a in the light harvesting complex B800-830 and the membrane of Chromatium purpuratum (purple photosynthetic bacterium) is studied by steady-state fluorescence and femtosecond transient absorption spectrscopy (Ref. 1328).							lmax (nm): n-hexane 307, 377, 457, 483, 516; and some cis forms (Ref. 1325)		in benzene-d6 of all-trans and some cis forms (Ref. 1325)	(Ref. 0059)	resonance-Raman of all-trans and some cis forms (Ref. 1325)	HPLC for all-trans and some cis forms (Ref. 1325)	Major or sole carotenoid in 9 species of Chromatiaceae, such as Chromatium okenii and Thiocystis gelatinosa (purple sulfer photosynthetic bacteria) (Ref. 1054)				The keto group at C-4' of okenone is single-bond trans-conformation for the conjugated double bond determined by NMR (Ref. 1325).	[0059] / [1054] / [1325] / [1328]
251		Rhodobacterioxanthin/ Spirilloxanthin-20-al	13-cis-1,1'-Dimethoxy-3,4,3',4'-tetradehydro-12,1',2'-tetrahydro-y,y-caroten-20-al	VCA1171	Shinichi Takaichi		C₄₂H₅₈O₃	610.908		A strong antioxidant effect on lipid peroxidation induced by a free radical and a singlet oxygen (Ref. 1338).							lmax (nm): diethylether 331, 389, 514 (Ref. 1338)		1H-NMR (Ref. 1338)	HR-EI-MS (Ref. 1338)			Rhodobacter capusulatus (purple photosynthetic bacterium) (Ref. 1338); identification of this strain is doubtful.					[1338]
252		b-Carotene 5,6-epoxide	5,6-Epoxy-5,6-dihydro-b,b-carotene	VCA1172	Shinichi Takaichi		C₄₀H₅₆O	552.872		b-Carotene 5,6-epoxide is present in the thyakoid membranes, especially in the PSII particles, of spinach and Synechococcus vulcanus (cyanobacteria). Both epoxidation and de-epoxidation reactions take place in intact spinach leaves, while epoxidation alone takes place in the purified membranes of both organisms (Ref. 1339). The carotenoid from barley is found only when chloroplasts and thylakoid are exposed to high light. It is associated with the PSI reaction centers (CP1 and CP1a) and not with the PSII reaction center (CPa). Since its circular dichroism is opticaly inactive, it is not produced enzymatically but is a product of photooxidation (Ref. 1340).							lmax (nm): n-hexane 425, 446, 477 (Ref. 1339); HPLC eluent 423, 449, 478 (Ref. 1340)			EI-MS: 552 (Ref. 1339/1340)	Raman spectroscopy (Ref. 1339)		Spinach and Synechococcus vulcanus (cyanobacteria) (Ref. 1339). Hordeum vulgare (barley) (Ref. 1340).					[1339] / [1340]
253		Didemethylspirilloxanthin glucoside	1'-(b-D-Glucopyranosyloxy)-3,4,3',4'-tetradehydro-1,2,1',2'-tetrahydro-y,y-caroten-1-ol	VCA1173	Shinichi Takaichi		C₄₆H₆₆O₇	731.012									lmax (nm): ethanol 306, 317, 371, 388, 468, 495, 529 (Ref. 1342)		1H- and 13C-NMR in pyridine (Ref. 1342)	FAB-MS, EI-MS (Ref. 1342)			Polyangium fumosum (Myxobacteria, bacteria) (Ref. 1342)				Didemethylspirilloxanthin and didemethylspirilloxanthin glucoside esters are also present (Ref. 1342).	[1342]
254		Didemethylspirilloxanthin glucoside ester	1'-(6-O-acyl-b-D-Glucopyranosyloxy)-3,4,3',4'-tetradehydro-1,2,1',2'-tetrahydro-y,y-caroten-1-ol	VCA1174	Shinichi Takaichi												lmax (nm): ethanol 306, 318, 371, 388, 469, 496, 530 (Ref. 1342)	(Ref. 1342)	1H- and 13C-NMR in CDCl3 (Ref. 1342)	FAB-MS, EI-MS (Ref. 1342)			Polyangium fumosum (Myxobacteria, bacteria) (Ref. 1342)				Attached fatty acids are only C14:0 and iso-C13:0. Didemethylspirilloxanthin and didemethylspirilloxanthin glucoside are also present (Ref. 1342).	[1342]
255		2-Hydroxyastaxanthin	(2R,3S,3'S)-2,3,3'-Trihydroxy-b,b-carotene-4,4'-dione	VCA1175	Shinichi Takaichi		C₄₀H₅₂O₅	612.838									lmax (nm): benzene 487 (Ref. 1343)		1H- and 13C-NMR in CDCl3 (Ref. 1343)	EI-MS, HR-EIMS (Ref. 1343)	CD in EPA (Ref. 1343)		Brevundimonas sp. SD212 (bacterium) (Ref. 1343)			Reaction products of Brevundimonas crtG expessed in E.coli with astaxanthin background (crtE, crtB, crtI, crtY and crtZ from Pantoea, and crtW from Paracoccus) (Ref. 1344)		[1343] / [1344]
256		2-Hydroxyadonixanthin	(2R,3S,3'S)-2,3,3'-Trihydroxy-b,b-caroten-4-one	VCA1176	Shinichi Takaichi		C₄₀H₅₄O₄	598.854									lmax (nm): benzene 476 (Ref. 1343)		1H-NMR in CDCl3 (Ref. 1343)	EI-MS, HR-EIMS (Ref. 1343)	CD in EPA (Ref. 1343)		Brevundimonas sp. SD212 (bacterium) (Ref. 1343)					[1343]
257		2,2'-Dihydroxyastaxanthin	(2R,3S,2'R,3'S)-2,3,2',3'-Tetrahydroxy-b,b-carotene-4,4'-dione	VCA1177	Shinichi Takaichi		C₄₀H₅₂O₆	628.837									lmax (nm): benzene 488 (Ref. 1343); ethanol 477, reduced form 429, 449, 477 (Ref. 0152)		1H-NMR in CDCl3 (Ref. 1343)	EI-MS (Ref. 1343)	CD in EPA (Ref. 1343); acetylated in CH2Cl2 (Ref. 0152)		Brevundimonas sp. SD212 (bacterium) (Ref. 1343) Rhizobium lupini (soil and root nodule bacterium) (Ref. 0152)					[0152] / [1343]
258		2-Hydroxycanthaxanthin	(2R)-2-Hydroxy-b,b-carotene-4,4'-dione	VCA1178	Shinichi Takaichi		C₄₀H₅₂O₃	580.839		Inhibitory effects on lipid peroxidation in a rat brain homogenate (Ref. 1344)							lmax (nm): 474 (Ref. 1344)		1H-NMR in CDCL3 (Ref. 1344)							Reaction products of Brevundimonas crtG expessed in E.coli with canthaxanthin background (crtE, crtB, crtI and crtY from Pantoea, and crtW from Paracoccus) (Ref. 1344)		[1344]
259		2,2'-Dihydroxycanthaxanthin	(2R,2'R)-2,2'-Dihydroxy-b,b-carotene-4,4'-dione	VCA1179	Shinichi Takaichi		C₄₀H₅₂O₄	596.838		Inhibitory effects on lipid peroxidation in a rat brain homogenate (Ref. 1344)							lmax (nm):?HPLC eluent 472 (Ref. 1344)		1H-NMR in CDCL3 (Ref. 1344)							Reaction products of Brevundimonas crtG expessed in E.coli with canthaxanthin background (crtE, crtB, crtI and crtY from Pantoea, and crtW from Paracoccus) (Ref. 1344)		[1344]
260		Saproxanthin	(3R)-3',4'-Didehydro-1',2'-dihydro-b,y-carotene-3,1'-diol	VCA1180	Shinichi Takaichi		C₄₀H₅₆O₂	568.871			178-179 C (Ref. 1351)						lmax (nm): acetone 451, 478.5, 509, %III/II=61, e478.5 = 162000 (Ref. 1351)	(Ref. 1351)					Major carotenoid of Saprospira grandis (nonfruiting gliding bacterium) (Ref. 1351)					[1351]
261		19-Methoxy siphonaxanthin	(3R,3'R,6'R)-3,3'-Dihydroxy-19-methoxy-7,8-dihydro-b,e-caroten-8-one	VCA1181	Shinichi Takaichi	Me-Sx	C₄₁H₅₈O₄	614.897									lmax (nm): HPLC eluent 451 (Ref. 1352)		1H-NMR, 13C-NMR in CDCl3 (Ref. 1352)	FD-MS: 614 (Ref. 1352)		HPLC of Nephroselmis sp. (Prasinophyceae) (Ref. 1352)	Nephroselmis sp. NIES 486, NIES-PS 535 and MBIC 10871 (Prasinophyceae, Chlorophyta) (Ref. 1352)					[1352]
262		1'-Hydroxytorulene/ 1'-OH-Torulene/ Myxocoxanthin	3',4'-Didehydro-1',2'-dihydro-b,y-caroten-1'-ol	VCA1182	Tokuji Takeda		C₄₀H₅₆O	552.872									lmax (nm): petroleum ether or hexane (361), (446-450), 473, 502 (Ref. 1355)			FD-MS: 552 (Ref. 1354); HR-MS (Ref. 1355)			Anaerobic light culture of Roseiflexus castenholzii (thermophilic filamentous photosynthetic bacterium) (Ref. 1354) Major carotenoid in Spirochaeta aurantia strain J1 and minor one in spirochete RS1 (Ref. 1355)					[1354] / [1355]
263		1',2'-Dihydro-1'-hydroxytorulene glucoside/ Myxocoxanthin glucoside	1'-(b-D-Glucopyranosyloxy)-3',4'-didehydro-1',2'-dihydro-b,y-carotene	VCA1183	Shinichi Takaichi	M-G	C₄₆H₆₆O₆	715.013												FD-MS: 714 (Ref. 1353)			Myxococcus sp. MY-18 (fruiting gliding myxobacterium) (Ref. 1353)					[1353]
264		1',2'-Dihydro-1'-hydroxytorulene rhamnoside/ Myxocoxanthin rhamnoside	1'-Rhamnosyloxy-3',4'-didehydro-1',2'-dihydro-b,y-carotene	VCA1184	Shinichi Takaichi	M-R	C₄₆H₆₆O₅	699.013									lmax (nm): ethanol 449, 472, 503 (Ref. 1358)			MS: peracetate 824 (Ref. 1358)			Sorangium compositum (Myxobacteriales) (Ref. 1358)				Rhamnose was identified after hydrolysis by TLC (Ref. 1358), and insufficient data for identification.	[1358]
265		1',2'-Dihydro-1'-hydroxytorulene glucoside ester/ Myxocoxanthin glucoside ester	1'-(6-O-Acyl-b-D-glucopyranosyloxy)-3',4'-didehydro-1',2'-dihydro-b,y-carotene	VCA1185	Shinichi Takaichi	M-G-FA											lmax (nm): methanol (449), 472, 503, %III/II=44 (Ref. 1353)			FD-MS: 896, 910 (iso C13:0), 924, 938 (Ref. 1353)			Myxococcus sp. MY-18 (fruiting gliding myxobacterium) (Ref. 1353) One of major carotenods in anaerobic light culture of Roseiflexus castenholzii (thermophilic filamentous photosynthetic bacterium) (Ref. 1354)				Major fatty acid is isoC13:0, and others are C12:0, C14:0, and iso C15:0 (Ref. 1353).	[1353] / [1354]
266		Myxobactone/ Keto-myxocoxanthin glucoside	1'-(b-D-Glucopyranosyloxy)-3',4'-didehydro-1',2'-dihydro-b,y-caroten-4-one	VCA1186	Shinichi Takaichi	KM-G	C₄₆H₆₄O₇	728.996												FD-MS: 728 (Ref. 1353/1354)			Myxococcus sp. MY-18 (fruiting gliding myxobacterium) (Ref. 1353) Aerobic dark and anaerobic light cultures of Roseiflexus castenholzii (thermophilic filamentous photosynthetic bacterium) (Ref. 1354)					[1353] / [1354]
267		Myxobactone ester/ Keto-myxocoxanthin glucoside ester	1'-(6-O-Acyl-b-D-Glucopyranosyloxy)-3',4'-didehydro-1',2'-dihydro-b,y-caroten-4-one	VCA1187	Shinichi Takaichi	KM-G-FA											lmax (nm): methanol (450), 475, (496); NaBH4 reduced form (448), 470, 500, %III/II=42 (Ref. 1353); methanol 280, 318, (453), 477, (501); NaBH4 reduced form 294, 364, (449), 472, 502, %III/II=50 (Ref. 1354)		H-NMR in CDCl3 (Ref. 1353) H- and C-NMR in CDCl3 (Ref. 1354)	FD-MS: 910, 924 (iso C13:0), 938, 952 (Ref. 1353)(Ref. 1354)			Major carotenoid of Myxococcus sp. MY-18 (fruiting gliding myxobacterium) (Ref. 1353). One of major carotenods in aerobic dark and anaerobic light cultures of Roseiflexus castenholzii (thermophilic filamentous photosynthetic bacterium) (Ref. 1354)				Major fatty acid is isoC13:0, and others are C12:0, C14:0, and iso C15:0 (Ref. 1353).	[1353] / [1354]
268		3,4-Dehydrorhodopin glucoside	1-(b-D-Glucopyranosyloxy)-3,4-didehydro-1,2-dihydro-y,y-carotene	VCA1188	Shinichi Takaichi		C₄₆H₆₆O₆	715.013															Carotenoid glucoside of 3,4-dehydrorhodopin glucoside esters in the nicotin added culture of Myxococcus sp. MY-18 (fruiting gliding myxobacterium) (Ref. 1353) and Chondromyces apiculatus strain Cm a2 (myxobacteria) (Ref. 1357)					[1353] / [1357]
269		3,4-Dehydrorhodopin glucoside ester	1-(6-O-Acyl-b-D-glucopyranosyloxy)-3,4-didehydro-1,2-dihydro-y,y-carotene	VCA1189	Shinichi Takaichi												lmax (nm): methanol 458, 481, 513, %III/II=51 (Ref. 1353)		H-NMR in CDCl3 (Ref. 1353)	FD-MS: 896, 910 (iso C13:0), 924, 938 (Ref. 1353)			Nicotin added culture of Myxococcus sp. MY-18 (fruiting gliding myxobacterium) (Ref. 1353) Minor carotenoid of Chondromyces apiculatus strain Cm a2 (myxobacteria) (Ref. 1357)				Glucose was identified after hydrolysis by TLC, and fatty acids were determined as their methyl esters by GLC (mainly C14:0, C16:0, C16:1, C18:0, C18:1) (Ref. 1357).	[1353] / [1357]
270		1'-Methoxy-3',4'-dehydro-g-carotene/ Methoxy-myxocoxanthin	1'-Methoxy-3',4'-didehydro-1',2'-dihydro-b,y-carotene	VCA1190	Shinichi Takaichi	Me-M	C₄₁H₅₈O	566.899									lmax (nm): petroleum ether 447, 473, 505 (Ref. 1356)			MS (Ref. 1356)			A minor carotenoid of Rhodomicrobium vannielii (Rhodospirillaceae) (Ref. 1356)					[1356]
271		Methoxy-keto-myxocoxanthin	1'-Methoxy-3',4'-didehydro-1',2'-dihydro-b,y-caroten-4-one	VCA1191	Shinichi Takaichi	Me-KM	C₄₁H₅₆O₂	580.882											H- and C-NMR in CDCl3 (Ref. 1354)	FD-MS: 580 (Ref. 1354)			One of major carotenods in aerobic dark culture of Roseiflexus castenholzii (thermophilic filamentous photosynthetic bacterium) (Ref. 1354)					[1354]
272		4,4'-Diaponeurosporen-4-al	7',8'-Dihydro-4,4'-diapo-y,y-caroten-4-al	VCA1192	Shinichi Takaichi		C₃₀H₄₀O	416.638									lmax (nm): light petroleum (444), 466, 496; reduced form (386), 413, 435, 465; ethanol 468; chloroform 470 (Ref. 1362)			(Ref. 1362)			Minor carotenoid (0.3%) of Streptococcus faecium UNH 564P (Gram-positive bacterium) (Ref. 1362)		The symmetrical carbon skeleton is reduced from biosynthetic labelling studies in Streptococcus faecium UNH 564P (Ref. 1363).			[1362] / [1363]
273		4,4'-Diaponeurosporen-4-oic acid	7',8'-Dihydro-4,4'-diapo-y,y-caroten-4-oic acid	VCA1193	Shinichi Takaichi		C₃₀H₄₀O₂	432.637									lmax (nm): light petroleum (441), 464, 490; diethyl ether 460, 483; 95% ethanol 463 (Ref. 1364)	(Ref. 1364)		(Ref. 1364)			Major carotenoid (11.5%) of Staphylococcus aureus 209P (Ref. 1364). Methylomonas sp. strain 16a (Ref. 1367)					[1364] / [1367]
274		4,4'-Diaplycopen-4-al	4,4'-Diapo-y,y-caroten-4-al	VCA1194	Shinichi Takaichi		C₃₀H₃₈O	414.622									lmax (nm): light petroleum (454), 476, 506; reduced form (404), 426, 452, 482; ethanol 477; chloroform 488 (Ref. 1362); ethanol 491; reduced form 442, 468, 500 (Ref. 1366)			(Ref. 1362/1366)			Minor carotenoid (0.5%) of Streptococcus faecium UNH 564P (Gram-positive bacterium) (Ref. 1362) Minor carotenoid from Methylobacterium rhodinum (formerly Pseudomonas rhodos) mutant (Ref. 1366)		The symmetrical carbon skeleton is reduced from biosynthetic labelling studies in Streptococcus faecium UNH 564P (Ref. 1363).			[1362] / [1363] / [1366]
275		4,4'-Diaplycopenedial	4,4'-Diapo-y,y-carotene-4,4'-dial	VCA1195	Shinichi Takaichi		C₃₀H₃₆O₂	428.606									lmax (nm): ethanol 501; reduced form 442, 468, 501 (Ref. 1366); HPLC eluent 507 (Ref. 1367)			(Ref. 1366)			Minor carotenoid from Methylobacterium rhodinum (formerly Pseudomonas rhodos) mutant (Ref. 1366)					[1366] / [1367]
276		4,4'-Diaplycopen-4'-al-4-oic acid/ 4,4'-Diapocaroten-4'-al-4-oic acid	4'-Oxo-4,4'-diapo-y,y-caroten-4-oic acid	VCA1196	Shinichi Takaichi		C₃₀H₃₆O₃	444.605									lmax (nm): ethanol 494; reduced form 445, 471, 503 (Ref. 1366)						Minor carotenoid from Methylobacterium rhodinum (formerly Pseudomonas rhodos) mutant (Ref. 1366)				Formation of a monomethyl etyher upon methylation using diazomethane (Ref. 1366).	[1366]
277		4,4'-Diaplycopene-4,4'-dioic acid	4,4'-Diapo-y,y-carotene-4,4'-dioic acid	VCA1197	Shinichi Takaichi		C₃₀H₃₆O₄	460.604									lmax (nm): HPLC luent 4465, 490, 519 (Ref. 1367)						Methylomonas sp. strain 16a (Ref. 1367)					[1367]
278		4,4'-Diaplycopenoic acid/ 4,4'-Diapocarotenoic acid	4,4'-Diapo-y,y-caroten-4-oic acid	VCA1198	Shinichi Takaichi		C₃₀H₃₈O₂	430.622									lmax (nm): ethanol (456), 477, 508 (Ref. 1365)		(Ref. 1365)	(Ref. 1365)			Minor carotenoid (8%) from Methylobacterium rhodinum (formerly Pseudomonas rhodos) (Ref. 1365)					[1365]
279		4,4'-Diapo-7,8,11,12-tetrahydrolycopene/ Asymmetric 4,4'-diapo-z-carotene	7,8,11,12-Tetrahydro-4,4'-diapo-y,y-carotene	VCA1199	Shinichi Takaichi		C₃₀H₄₄	404.670									lmax (nm): petroleum (354), 374, 395, 419 (Ref. 1368)			(Ref. 1368)			Streptococcus faecium UNH 564P (1% of total) (Ref. 1368)		The symmetrical carbon skeleton is reduced from biosynthetic labelling studies in Streptococcus faecium UNH 564P (Ref. 1369).			[1368] / [1369]
280		4-Hydroxy-4,4'-diaponeurosporene	7',8'-Dihydro-4,4'-diapo-y,y-caroten-4-ol	VCA1200	Shinichi Takaichi		C₃₀H₄₂O	418.654									lmax (nm): petroleu? (386), 413, 435, 465 (Ref. 1370)	(Ref. 1370)		(Ref. 1370)			Streptococcus faecium UNH 564P (Ref. 1370)		The symmetrical carbon skeleton is reduced from biosynthetic labelling studies in Streptococcus faecium UNH 564P (Ref. 1363/1369).			[1363] / [1369] / [1370]
281		4-(D-Glucopyranosyloxy)-7',8'-dihydro-4,4'-diaponeurosporene	4-(D-Glucopyranosyloxy)-7',8'-dihydro-4,4'-diapo-y,y-carotene	VCA1201	Shinichi Takaichi		C₃₆H₅₂O₆	580.794									lmax (nm): ethanol (391), 416, 439, 468; diethyl ether (390), 414, 437, 466; CHCl3 (400), 424, 450, 479 (Ref. 1370)			(Ref. 1370)			Streptococcus faecium UNH 564P (Ref. 1370)				D-Glucose moiety is identified by silica gel G TLC, paper chromatography, and a D-glucose oxidase-peroxidase system (Ref. 1370).	[1370]

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AUTHOR	:	Strain,H.H.,Svec,W.A.,Aitzetmüller,K.,Grandolfo,M.C.,Katz,J.J.,Kjfsen,H., Norgård,S.,Liaaen-Jensen,S.,Haxo,F.T, and Rapoport, P.W.F.
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[0047]

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[0054]

AUTHOR	:	Hengartner,U.,Bernhard,K.,Meyer,K.,Englert,G., and Glinz,E.
TITLE	:	Synthesis, Isolation, and NMR-Spectroscopic Characterization of Fourteen (Z)-Isomers of Lycopene and Some Acetylenic Didehydro- and Tetrahydrolycopenes
JOURNAL	:	Helv. Chim. Acta
VOL	:	75 PAGE : 1848-1865 (1992)

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AUTHOR	:	Isler,O.,Gutmann,H.,Lindlar,H.,Montavon,M.,Rüegg,R., and Zeller,P.
TITLE	:	Synthesen in der Carotinoid-Reihe. Synthese von Crocetindialdehyd und Lycopin
JOURNAL	:	Helv. Chim. Acta
VOL	:	39 PAGE : 463-473 (1956)

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AUTHOR	:	Manchand,P.S.,Rüegg,R.,Schwieter,U.,Siddons,P.T., and Weedon,B.C.L.
TITLE	:	Carotenoid and Related Compounds. Part XI. Syntheses of d-Carotene and e-Carotene
JOURNAL	:	J. Chem. Soc., Pert II
VOL	:	PAGE : 2019-2026 (1965)

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AUTHOR	:	Mayer,H.
TITLE	:	Synthesis of optically active carotenoids and related compounds
JOURNAL	:	Pure Appl. Chem.
VOL	:	51 PAGE : 535-564 (1979)

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[0058]

AUTHOR	:	Bjfrnland,T. and Aguilar-Martinez,M.
TITLE	:	Carotenoids in red algae
JOURNAL	:	Phytochemistry
VOL	:	15 PAGE : 291-296 (1976)

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[0059]

AUTHOR	:	Enzell,C.R.,Francis,G.W., and Liaaen-Jensen,S.
TITLE	:	Mass Spectrometric Studies of Carotenoids 2. A Survey of Fragmentation Reactions
JOURNAL	:	Acta Chim. Scand.
VOL	:	23 PAGE : 727-750 (1969)

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AUTHOR	:	Schwieter,U.Englert,G.,Rigassi,N., and Vetter,W.
TITLE	:	Physical organic methods in carotenid research
JOURNAL	:	Pure Appl. Chem.
VOL	:	20 PAGE : 365-420 (1969)

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AUTHOR	:	Moss,G.P.
TITLE	:	Carbon-13 NMR spectra of carotenoids
JOURNAL	:	Pure Appl. Chem.
VOL	:	2047 PAGE : 97-102 (1976)

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AUTHOR	:	Koyama,Y.,Hosomi,M.,Miyata,A.,Hashimoto,H., and Reames,S.A.
TITLE	:	Supplementary and revised assignment of the peaks of the 7,9-, 9,9'-, 13,13'-, 9,13'-di-cis and 9,9',13-tri-cis isomers of b-carotene in high-performance liquid chromatography using a column of calcium hydroxide
JOURNAL	:	J. Chromatogr.
VOL	:	439 PAGE : 417-422 (1988)

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[0063]

AUTHOR	:	Britton,G. (1995) Carotenoids Volume 1B: Spectroscopy Chapter 2: UV/Visible Spectroscopy (Britton,G.,Liaaen-Jensen,S., and Pfander,H., eds), pp13-62, Birkhäuser Verlag,Basel,Boston,Berlin
TITLE	:
JOURNAL	:
VOL	:	PAGE : - ()

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AUTHOR	:	Buchecker,R., and Noack,K. (1995) Carotenoids Volume 1B: Spectroscopy Chapter 3: Circular Dichroism (Britton,G.,Liaaen-Jensen,S., and Pfander,H., eds), pp63-116, Birkhäuser Verlag,Basel,Boston,Berlin
TITLE	:
JOURNAL	:
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AUTHOR	:	Bernhard,K., and Grosjean,M. (1995) Carotenoids Volume 1B: Spectroscopy Chapter 4: Infrared Spectroscopy (Britton,G.,Liaaen-Jensen,S., and Pfander,H., eds), pp117-146, Birkhäuser Verlag,Basel,Boston,Berlin
TITLE	:
JOURNAL	:
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AUTHOR	:	Vecchi,M.,Englert,G.,Maurer,R., and Meduna,V.
TITLE	:	Trennung und Charakterisierung von b-Carotin-Isomeren
JOURNAL	:	Helv. Chim. Acta
VOL	:	64 PAGE : 2746-2758 (1981)

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[0067]

AUTHOR	:	Bushway,R.J.
TITLE	:	Determination of a- and b-Carotene in Some Raw Fruit and Vegetables by High-Performance Liquid Chromatography
JOURNAL	:	J. Agric. Food. Chem.
VOL	:	34 PAGE : 409-412 (1986)

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[0068]

AUTHOR	:	Yokoyama, A., Izumida, H., and Miki, W.
TITLE	:	Production of Astaxanthin and 4-Ketozeaxanthin by the Marine Bacterium, Agrobacterium aurantiacum
JOURNAL	:	Biosci. Biotechnol. Biochem.
VOL	:	58 PAGE : 1842-1844 (1994)

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[0069]

AUTHOR	:	Pfander,H., and Riesen,R. (1995) Carotenoids Volume 1A: Isolation and Analysis Chapter 6: Chromatography: Part IV High-Performance Liquid Chromatography (Britton,G.,Liaaen-Jensen,S., and Pfander,H., eds), pp145-190, Birkhäuser Verlag,Basel,Boston,Berlin
TITLE	:
JOURNAL	:
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[0070]

AUTHOR	:	Maoka,T.,Komori,T., and Matsuno,T.
TITLE	:	Direct diastereomeric resolution of carotenoids I. 3-Hydroxy-4-oxo-b-end group
JOURNAL	:	J. Chromatogr.
VOL	:	318 PAGE : 122-124 (1985)

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[0071]

AUTHOR	:	Englert,G., and Vecchi,M.
TITLE	:	trans/cis Isomerization of Astaxanthin Diacetate/Isolation by HPLC and Identification by ¹H-NMR Spectroscopy of Three Mono-cis- and Six Di-cis-Isomers
JOURNAL	:	Helv. Chim. Acta
VOL	:	63 PAGE : 1711-1718 (1980)

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[0073]

AUTHOR	:	Becher,E.,Albrecht,R.,Bernhard,K.,Leuenberger,H.G.W.,Mayer,H.,Müller,R.K.,Schüep,W., and Wagner,H.P.
TITLE	:	Synthese von Astaxanthin aus b-Jonon. I. Erschliessung der enantiomeren C15-Wittig salze durch chemische und mikrobiologishe Racematspaltung von ()-3-Acetoxy-4-oxo-b-jonon
JOURNAL	:	Helv. Chim. Acta
VOL	:	64 PAGE : 2419-2435 (1981)

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[0076]

AUTHOR	:	Rüttimann,A., and Mayer,H.
TITLE	:	Synthese von optisch aktiven, natürlichen Carotenoiden und strukturell verwandten Naturprodukten V. Synthese von (3R,3'R)-, (3S,3'S)- und (3R,3'S;meso)-Zeaxanthin durch asymmetrische Hydroborierung. Ein neuer Sugang zu optisch aktiven Carotinoidbausteinen
JOURNAL	:	Helv. Chim. Acta
VOL	:	63 PAGE : 1456-1462 (1980)

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[0077]

AUTHOR	:	Bernhard,K.,Englert,G.,Mayer,H.,Müller,R.K.,Rüttimann,A.,Vecchi,M.,Widmer,E., and Zell,R.
TITLE	:	Synthese von optisch aktiven, natürlichen Carotenoiden und strukturell verwandten Naturprodukten IX. Synthese von (3R)-Hydroxyechinenon, (3R,3'R)- und (3R,3'S)-Adnixanthin, (3R)-Adonirubin, deren optischen Antipoden und verwandten Verbindungen
JOURNAL	:	Helv. Chim. Acta
VOL	:	64 PAGE : 2469-2484 (1981)

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[0078]

AUTHOR	:	Noack,K.
TITLE	:	Temperaturabhängiger Circulardichroismus von (3S,3'R)- und (3S,3'S)-Adnixanthin
JOURNAL	:	Helv. Chim. Acta
VOL	:	64 PAGE : 1833-136 (1981)

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[0079]

AUTHOR	:	Bjfrnland,T., Borch,G., and Liaaen-Jensen,S.
TITLE	:	Algal carotenoids: 29. Configurational studies on red algae carotenoids
JOURNAL	:	Phytochemistry
VOL	:	23 PAGE : 1711-1715 (1984)

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[0080]

AUTHOR	:	Englert,G., Kienzle,F., and Noack,K.
TITLE	:	¹H-NMR., ¹³C-NMR., UV. and CD. spectral data of synthetic (3S,3'S)-astaxanthin, its 15-cis isomer, and some related compounds
JOURNAL	:	Helv. Chim. Acta
VOL	:	60 PAGE : 1209-1219 (1977)

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AUTHOR	:	Aakermann,T., and Liaaen-Jensen,S.
TITLE	:	Pyrrhoxanthin, reisolation and absolute configuration
JOURNAL	:	Phytochemistry
VOL	:	31 PAGE : 1779-1782 (1992)

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[0082]

AUTHOR	:	Rüegg,R.,Schwieter,U.,Ryser,G.,Schudel,P., und Isler,O.
TITLE	:	Synthesen in der Carotinoid-Reihe g-Carotin sowie d,l-a- und b-Carotin aus Dehydro-b-apo-12'-carotenal (C25)
JOURNAL	:	Helv. Chim. Acta
VOL	:	44 PAGE : 985-993 (1961)

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[0083]

AUTHOR	:	Tscharner,C.,Eugster,C.H., and Karrer,P.
TITLE	:	Synthese der optisch activen a-Carotin .Carotinoidsynthesen XX
JOURNAL	:	Helv. Chim. Acta
VOL	:	40 PAGE : 1676-1677 (1957)

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[0084]

AUTHOR	:	Buchecker,R.,Egli,R.,Regel-Wild,H.,Tscharner,C.,Eugster,C.H.,Uhde,G., and Ohloff,G.
TITLE	:	Absolute Konfiguration der enantiomeren a-Cyclogeranium-säuren
JOURNAL	:	Helv. Chim. Acta
VOL	:	56 PAGE : 2548-2563 (1973)

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[0085]

AUTHOR	:	Yokoyama,A.,Adachi,K., and Shizuri,Y.
TITLE	:	New Carotenoid Glucosides, Astaxanthin Glucoside and Adonixanthin Glucoside, Isolation from the Astaxanthin-Producing Marine Bacterium Agrobacterium aurantiacum
JOURNAL	:	J. Nat. Prod.
VOL	:	58 PAGE : 1929-1933 (1995)

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[0086]

AUTHOR	:	Mayer,H., and Rüttimann,A.
TITLE	:	Synthese von optisch aktiven, natürlichen Carotinoiden und strukturell verwandeten Naturprodukten IV. Synthese von (3R,2'R,6'R)-Lutein
JOURNAL	:	Helv. Chim. Acta
VOL	:	63 PAGE : 1451-1455 (1980)

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[0087]

AUTHOR	:	Isler,O.,Lindlar,H.,Montavon,M.,Rüegg,R., and Zeller,P.
TITLE	:	Synthesen in der Carotinoid-Reihe. Die Synthese von 3,4; 3',4'-Bisdehydro-b-carotin und 3,4-Monodehydro-b-carotin
JOURNAL	:	Helv. Chim. Acta
VOL	:	39 PAGE : 274-282 (1956)

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AUTHOR	:	Di Mascio, P., Kaiser, S., and Sies, H.
TITLE	:	Lycopene as the most efficient biological carotenoid singlet oxygen quencher PubMed ID:2802626
JOURNAL	:	Arch Biochem Biophys.
VOL	:	274 PAGE : 532-538 (1989)

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[0090]

AUTHOR	:	Kennedy, T. A., and Liebler, D. C.
TITLE	:	Peroxyl radical scavenging by beta-carotene in lipid bilayers. Effect of oxygen partial pressure PubMed ID:1537849
JOURNAL	:	J Biol Chem.
VOL	:	267 PAGE : 4658-4663 (1992)

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AUTHOR	:	Vile, G. F., and Winterbourn, C. C.
TITLE	:	Inhibition of adriamycin-promoted microsomal lipid peroxidation by beta-carotene, alpha-tocopherol and retinol at high and low oxygen partial pressures PubMed ID:3169265
JOURNAL	:	FEBS Lett.
VOL	:	238 PAGE : 353-356 (1988)

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AUTHOR	:	Lim, B. P., Nagao, A., Terao, J., Tanaka, K., Suzuki, T., and Takama, K.
TITLE	:	Antioxidant activity of xanthophylls on peroxyl radical-mediated phospholipid peroxidation PubMed ID:1627620
JOURNAL	:	Biochim Biophys Acta.
VOL	:	1126 PAGE : 178-184 (1992)

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AUTHOR	:	Terao, J.
TITLE	:	Antioxidant activity of beta-carotene-related carotenoids in solution PubMed ID:2779372
JOURNAL	:	Lipids.
VOL	:	24 PAGE : 659-661 (1989)

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AUTHOR	:	Okuzumi,J.,Takahashi,T.,Yamane,T.,Kitao,Y.,Inagake,M.,Ohya,K.,Nishino,H., and Tanaka,Y.
TITLE	:	Inhibitory effects of fucoxanthin, a natural carotenoid, on N-ethyl-N'-nitro-N-nitrosoguanidine-induced mouse duodenal carcinogenesis PubMed ID:8443788
JOURNAL	:	Cancer Lett.
VOL	:	68 PAGE : 159-168 (1993)

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AUTHOR	:	Okuzumi,J.
TITLE	:	Antiproliferative and antitumor promoting activities of fucoxanthin, a natural carotenoid
JOURNAL	:	J. Kyoto Pref. Univ. Med.
VOL	:	100 PAGE : 551-566 (1991)

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AUTHOR	:	Nishino,H.,Satomi,Y.,Tokuda,H.,Nishino,A.,Iwashima,A.,Tanaka,Y.,Yamano,Y.,Shibata,Y.,Torihara,M.,Tamai,Y., and Ito,M.
TITLE	:	Anti-tumor activity of peridinin and its structurally related butenolide compounds
JOURNAL	:	J. Kyoto Pref. Univ. Med.
VOL	:	100 PAGE : 831-835 (1991)

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AUTHOR	:	Murakoshi, M., Takayasu, J., Kimura, O., Kohmura, E., Nishino, H., Iwashima, A., Okuzumi, J., Sakai, T., Sugimoto, T., Imanishi, J., et al.
TITLE	:	Inhibitory effects of alpha-carotene on proliferation of the human neuroblastoma cell line GOTO PubMed ID:2795693
JOURNAL	:	J Natl Cancer Inst.
VOL	:	81 PAGE : 1649-1652 (1989)

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AUTHOR	:	Seifter, E., Rettura, G., Padawer, J., and Levenson, S. M.
TITLE	:	Moloney murine sarcoma virus tumors in CBA/J mice: chemopreventive and chemotherapeutic actions of supplemental beta-carotene PubMed ID:6279952
JOURNAL	:	J Natl Cancer Inst.
VOL	:	68 PAGE : 835-840 (1982)

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AUTHOR	:	Suda, D., Schwartz, J., and Shklar, G.
TITLE	:	Inhibition of experimental oral carcinogenesis by topical beta carotene PubMed ID:3084114
JOURNAL	:	Carcinogenesis.
VOL	:	7 PAGE : 711-715 (1986)

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AUTHOR	:	Temple, N. J., and Basu, T. K.
TITLE	:	Protective effect of beta-carotene against colon tumors in mice PubMed ID:3473257
JOURNAL	:	J Natl Cancer Inst.
VOL	:	78 PAGE : 1211-1214 (1987)

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AUTHOR	:	Olson, J. A.
TITLE	:	Provitamin A function of carotenoids: the conversion of beta-carotene into vitamin A PubMed ID:2643691
JOURNAL	:	J Nutr.
VOL	:	119 PAGE : 105-108 (1989)

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AUTHOR	:	Burton, G. W.
TITLE	:	Antioxidant action of carotenoids PubMed ID:2643692
JOURNAL	:	J Nutr.
VOL	:	119 PAGE : 109-111 (1989)

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AUTHOR	:	Ikuno,Y.,Shimizu,M.,Koshino,Y.,Maoka,T., and Matsuno,T.
TITLE	:	Stereochemical Investigation of Carotenoids from Yellow-tail Rocfish Sebastes flavidus
JOURNAL	:	Bull. Japan. Soc. Sci. Fish.
VOL	:	51 PAGE : 2033-2035 (1985)

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[0112]

AUTHOR	:	Maoka,T., and Matsuno,T.
TITLE	:	The First Isolation and Identification of Tunaxanthin D, [(3S,6R,3'R,6'S)-e,e-carotene-3,3'-diol] from Marine Fishes
JOURNAL	:	Bull. Japan. Soc. Sci. Fish.
VOL	:	51 PAGE : 1349-1351 (1985)

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[0113]

AUTHOR	:	Matsuno,T., and Ookubo,M.
TITLE	:	The First Isolation and Identification of Fritschiellaxanthin from a Crab Sesarma haematocheir (AKATEGANI in Japanese)
JOURNAL	:	Bull. Japan. Soc. Sci. Fish.
VOL	:	48 PAGE : 653-659 (1982)

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[0114]

AUTHOR	:	Matsuno,T.,Maoka,T., and Katsuyama,M.
TITLE	:	The Identity of Tunaxanthin C and (3R,6S,3'R,6'S)-e,e-Caroene-3,3'-diol (Oxyxanthin 58)
JOURNAL	:	Bull. Japan. Soc. Sci. Fish.
VOL	:	50 PAGE : 1445-1445 (1984)

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[0115]

AUTHOR	:	Matsuno,T.,Katsuyama,M., and Maoka,T.
TITLE	:	Isolation of Lactucaxanthin from Tilapia Tilapia nilotica
JOURNAL	:	Bull. Japan. Soc. Sci. Fish.
VOL	:	50 PAGE : 1735-1737 (1984)

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AUTHOR	:	Buchecker,R.,Eugster,C.H., and Weber,A.
TITLE	:	Absolute Konfiguration von a-Doradexanthin und con Fritshiellaxanthin, einem neuen Carotinoid aus Fritchiella tuberosa IYENG.
JOURNAL	:	Helv. Chim. Acta
VOL	:	61 PAGE : 1962-1968 (1978)

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[0117]

AUTHOR	:	Matsuno,T.,Maoka,T., and Ikuno,Y.
TITLE	:	Comparative biochemical studies of carotenoids in fish: 27. Carotenoids in the eggs of three species of Cyprindae
JOURNAL	:	Comp. Biochem. Physiol.
VOL	:	83 PAGE : 335-337 (1986)

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AUTHOR	:	Andrews,A.G.,Englert,G.,Borch,G.,Strain,H.H., and Liaaen-Jensen,S.
TITLE	:	Absolute configuration of eschscholtzxanthin
JOURNAL	:	Phytochemistry
VOL	:	18 PAGE : 303-309 (1979)

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[0120]

AUTHOR	:	Strain,H.H.,Thomas,M.R., and Kats,J.J.
TITLE	:	Spectra of Eschscholtzxanthin and Other Carotenoid Pigment
JOURNAL	:	J. Org. Chem.
VOL	:	26 PAGE : 5061-5064 (1961)

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AUTHOR	:	Surmatis,J.D.,Walser,A.,Gibas,J.,Schwieter,U., and Thommen,R.
TITLE	:	New Methods for the Synthesis of Oxygenated Carotenoids
JOURNAL	:	Helv. Chim. Acta
VOL	:	53 PAGE : 974-990 (1976)

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[0122]

AUTHOR	:	Mayer,H.,Montavon,M.,Rüegg,R., and Isler,O.
TITLE	:	Synthesen in der Carotinoid-Reiche Totalsynthese von Rhodoxanthin
JOURNAL	:	Helv. Chim. Acta
VOL	:	50 PAGE : 1606-1618 (1967)

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AUTHOR	:	Widmer,E.,Soukup,M.,Zell,R.,Broger,E.,Lohri,B.,Marbet,R., and Lukác,T.
TITLE	:	Technische Verfahren zur Synthese von Carotinoiden und verwandten Verbindungen aus 6-Oxo-isophoron. VI. Synthese von Rhodoxanthin und (3RS,3'RS)-Zeaxanthin; Zugänge zur C15-Ringkomponente über 3-Oxo-jonon-Derivate
JOURNAL	:	Helv. Chim. Acta
VOL	:	65 PAGE : 944-957 (1982)

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AUTHOR	:	Widmer,E.,Zell,R.,Grass,H., and Marbet,R.
TITLE	:	Technische Verfahren zur Synthese von Carotinoiden und verwandten Verbindungen aus 6-Oxo-isophoron. VII. Synthese von Rhodoxanthin und (3RS,3'RS)-Zeaxanthin aus der C15-Ringkomponente
JOURNAL	:	Helv. Chim. Acta
VOL	:	65 PAGE : 958-966 (1982)

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[0125]

AUTHOR	:	Ida,K.,Masamoto,K.,Maoka,T.,Fujiwara,Y.,Takeda,S., and Hasegawa,E.
TITLE	:	The Leaves of the Common Box, Buxus sempervirens (Buxaceae), Become Red as the Level of a Red Carotenoid, Anhydroeschscholtzxanthin, Increases
JOURNAL	:	J. Plant Res.
VOL	:	108 PAGE : 369-376 (1995)

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[0126]

AUTHOR	:	Karrer,P., and Leumann,E.
TITLE	:	Eschscholtzxanthin und Anhydro-eschscholtzxanthin
JOURNAL	:	Helv. Chim. Acta
VOL	:	34 PAGE : 445-453 (1951)

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[0127]

AUTHOR	:	Buchecker,R., and Eugster,C.H.
TITLE	:	Search for the presence in egg yolk, in flowers of Caltha palustris and in autumn leaves of 3'-epilutein (= (3R,3'S,6'R)-b,e-carotene-3,3'-diol) and 3',O-didehydrolutein (= (3R,6'R)-3-hydroxy-b,e-carotene-3'-one)
JOURNAL	:	Helv. Chim. Acta
VOL	:	62 PAGE : 2817-2824 (1979)

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[0128]

AUTHOR	:	Vecchi,M.,Englert,G., and Mayer,H.
TITLE	:	Chromatographische Trennung und Identifizierung diastereomerer Carotinoide mit grossem räumlichem Abstand der chiralen Zentren""
JOURNAL	:	Helv. Chim. Acta
VOL	:	65 PAGE : 1050-1058 (1982)

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AUTHOR	:	Siefermann-Harms,D.,Hertzberg,S.,Borch,G., and Liaaen-Jensen,S.
TITLE	:	Lactucaxanthin, an e,e-carotene-3,3'-diol from Lactuca sativa
JOURNAL	:	Phytochemistry
VOL	:	20 PAGE : 85-88 (1981)

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[0130]

AUTHOR	:	Ikuno,Y.,Maoka,T.,Shimizu,M.,Komori,T., and Matsuno,T.
TITLE	:	Direct diastereomeric resolution of carotenoids II. All ten stereoisomers of tunaxanthin (e,e-caroten-3,3'-diol
JOURNAL	:	J. Chromatogr.
VOL	:	328 PAGE : 387-391 (1985)

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AUTHOR	:	Bingham,A.,Mosher,H.S., and Andrews,A.G.
TITLE	:	Epimeric 3,3'-Dihydroxy-e,e-carotenes from the Skin of the Yellow Costa Rican Frog, Atelopus chiriquiensis
JOURNAL	:	J. Chem. Soc., Chem. Commun.
VOL	:	PAGE : 96-97 (1977)

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[0132]

AUTHOR	:	Castillo,R., and Lenel,R.
TITLE	:	DETERMINATION AND METABOLISM OF CAROTENOID PIGMENTS IN THE HERMIT CRAB CLIBAN ARIUS ERYTHROPUS LATREILLE (1818) [SYN. Cl. MISANTHROPUS HELLER (1863)]
JOURNAL	:	Comp. Biochem. Physiol.
VOL	:	59 PAGE : 67-73 (1978)

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AUTHOR	:	Bingham,A.Jr,Wilkie,D.W., and Mosher,H.S.
TITLE	:	Tunaxanthin: occurrence and absolute stereochemistry
JOURNAL	:	Comp. Biochem. Physiol.
VOL	:	62 PAGE : 489-495 (1979)

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AUTHOR	:	Rosenberger,M.,McDougal,P., and Bahr,J.
TITLE	:	Canthaxanthin. A New Total Synthesis
JOURNAL	:	J. Org. Chem.
VOL	:	47 PAGE : 2130-2134 (1982)

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AUTHOR	:	Isaksen,M., and Francis,G.W.
TITLE	:	Reversed-phase thin-layer chromatography of carotenoids
JOURNAL	:	J. Chromatogr.
VOL	:	355 PAGE : 358-362 (1986)

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AUTHOR	:	Philip,T., and Francis,F.J.
TITLE	:	Isolation and chemical properties of capsanthin and derivatives
JOURNAL	:	J. Food Sci.
VOL	:	36 PAGE : 823-827 (1971)

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AUTHOR	:	Eller,P.,Bader,F.,Lindlar,H.,Montavon,M.,Müller,P.,Rüegg,R.,Ryser,G.,Saucy,G.,Schaeren,S.F.,Schwieter,U.,Stricker,K.,Tamm,R.,Zürcher,P., and Isler,O.
TITLE	:	Synthesen in der Carotinoid-Reihe Synthese von Canthaxanthin
JOURNAL	:	Helv. Chim. Acta
VOL	:	42 PAGE : 841-847 (1959)

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AUTHOR	:	Warren,C.K., and Weedon,B.C.L.
TITLE	:	Carotenoids and Related compounds. Part VII. Synthesis of Canthaxanthin and Echinenone
JOURNAL	:	J. Chem. Soc.
VOL	:	PAGE : 3986-3993 (1958)

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AUTHOR	:	Rüttimann,A.,Englert,G.,Mayer,H.,Moss,G.P., and Weedon,B.C.L.
TITLE	:	Synthese von optisch aktiven, natürlichen Carotinoiden und strukturell verwandten Naturprodukten. X. Synthese von (3R,3'S,5'R)-Capsanthin, (3S,5R,3'S,5'R)-Capsorbin, (3'S,5'R)-Kryptocapsin und einigen verwandten Verbindungen. Ein neuer Zugang zu optisch aktiven Fünfring-Carotinoidbausteinen durch Hydroborierung
JOURNAL	:	Helv. Chim. Acta
VOL	:	66 PAGE : 1939-1960 (1983)

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[0141]

AUTHOR	:	Bowden,R.D.,Cooper,R.D.G.,Harris,C.H.,Moss,G.P.,Weedon,B.C.L., and Jackman,L.M.
TITLE	:	Carotenoids and Related Compounds. Part 37. Stereochemistry and Synthesis of Capsorubin
JOURNAL	:	J. Chem. Soc., Perkin Trans. 1
VOL	:	PAGE : 1465-1474 (1983)

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[0143]

AUTHOR	:	Bernhard,K., Kienzle,F., Mayer,H., and Müller, R.K.
TITLE	:	Synthesis of optically active natural carotenoids and structurally related compounds. VIII. Synthesis of (3S,3'S)-7,8,7',8'-tetradehydroastaxanthin and (3S,3'S)-7,8-didehydroastaxanthin (asterinic acid)
JOURNAL	:	Helv. Chim. Acta
VOL	:	63 PAGE : 1473-1490 (1980)

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[0145]

AUTHOR	:	Davies,A.,Khare,A.,Mallams,A.K.,Massy-Westropp,R.A.,Moss,G.P., and Weedon,B.C.L.
TITLE	:	Carotenoids and Related Compounds. Part 38. Synthesis of (3RS,3'RS)-Alloxanthin and Other Acetylenes
JOURNAL	:	J. Chem. Soc., Perkin Trans. 1
VOL	:	PAGE : 2147-2157 (1984)

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[0146]

AUTHOR	:	Haugan,A.J. and Liaaen-Jensen,S.
TITLE	:	Total Synthesis of Acetylenic Carotenoids. 2. Synthesis of (all-E)-(3R,3'R)-Diatoxanthin and (all-E)-(3R)-7,8-Dehydrocryptoxanthin
JOURNAL	:	Acta Chem. Scand.
VOL	:	48 PAGE : 899-904 (1994)

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[0147]

AUTHOR	:	Bjfrnland,T.,Liaaen-Jensen,S., and Throndsen,J.
TITLE	:	Carotenoids of the marine Chrysophyte pelagococcus subviridis
JOURNAL	:	Phytochemistry
VOL	:	28 PAGE : 3347-3353 (1989)

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[0148]

AUTHOR	:	Haugan,A.J.,Englert,G., and Liaaen-Jensen,S.
TITLE	:	Algal Carotenoids 50. Alkali Lability of Fucoxanthin - Reactions and Products
JOURNAL	:	Acta. Chem. Scand.
VOL	:	46 PAGE : 614-624 (1992)

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[0149]

AUTHOR	:	Arpin,N.,Svec,W.A., and Liaaen-Jensen,S.
TITLE	:	New fucoxanthin - related carotenoids from Coccolithus huxleyi
JOURNAL	:	Phytochemistry
VOL	:	15 PAGE : 529-532 (1976)

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[0150]

AUTHOR	:	Hertzberg,S.,Mortensen,T.,Borch,G.,Siegelman,H.W., and Liaaen-Jensen,S.
TITLE	:	On the absolute configuration of 19'-hexanoyloxyfucoxanthin
JOURNAL	:	Phytochemistry
VOL	:	16 PAGE : 587-590 (1977)

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[0152]

AUTHOR	:	Beyer, P., Kleinig, H., Englert, G., Meister, W., and Noack, K.
TITLE	:	Carotenoids of Rhizobia. IV. Isolation and Structre Elucidation of the Carotenoids of a Mutant of Rhizobium lupini
JOURNAL	:	Helv. Chim. Acta
VOL	:	62 PAGE : 2551-2557 (1979)

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[0153]

AUTHOR	:	Baumeler,A., and Eugster,C.H.
TITLE	:	Synthese von (6R,all-E)-Neoxanthin und verwandten Allen-Carotinoiden
JOURNAL	:	Helv. Chim. Acta
VOL	:	75 PAGE : 773-790 (1992)

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[0154]

AUTHOR	:	Takaichi,S., and Mimuro,M.
TITLE	:	Distribution and Geometric Isomerization of Neoxanthin in Oxygenic Phototrophs: 9'-Cis, a Sole Molecular Form
JOURNAL	:	Plant Cell Physiol.
VOL	:	39 PAGE : 968-977 (1998)

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[0155]

AUTHOR	:	Acemoglu,M.,Uebelhart,P.,Rey,M., and Eugster,C.H.
TITLE	:	Synthese von enantiomerenreinen Violaxanthine und verwandten Verbindungen
JOURNAL	:	Helv. Chim. Acta
VOL	:	71 PAGE : 931-956 (1988)

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[0156]

AUTHOR	:	Radics,L.,Molnár,P., and Szabolcs,J.
TITLE	:	¹³C NMR evidence for the central nono-cis stereochemistry of a naturally occurring violaxanthin isomer
JOURNAL	:	Phytochemistry
VOL	:	22 PAGE : 306-306 (1983)

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[0201]

AUTHOR	:	Misawa, N., Nakagawa, M., Kobayashi, K., Yamano, S., Izawa, Y., Nakamura, K., and Harashima, K.
TITLE	:	Elucidation of the Erwinia uredovora carotenoid biosynthetic pathway by functional analysis of gene products expressed in Escherichia coli PubMed ID:2254247
JOURNAL	:	J Bacteriol.
VOL	:	172 PAGE : 6704-6712 (1990)

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[0202]

AUTHOR	:	Misawa, N., Satomi, Y., Kondo, K., Yokoyama, A., Kajiwara, S., Saito, T., Ohtani, T., and Miki, W.
TITLE	:	Structure and functional analysis of a marine bacterial carotenoid biosynthesis gene cluster and astaxanthin biosynthetic pathway proposed at the gene level PubMed ID:7592436
JOURNAL	:	J Bacteriol.
VOL	:	177 PAGE : 6575-6584 (1995)

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[0203]

AUTHOR	:	Kajiwara, S., Kakizono, T., Saito, T., Kondo, K., Ohtani, T., Nishio, N., Nagai, S., and Misawa, N.
TITLE	:	Isolation and functional identification of a novel cDNA for astaxanthin biosynthesis from Haematococcus pluvialis, and astaxanthin synthesis in Escherichia coli PubMed ID:7579184
JOURNAL	:	Plant Mol Biol.
VOL	:	29 PAGE : 343-352 (1995)

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[0204]

AUTHOR	:	Pasamontes, L., Hug, D., Tessier, M., Hohmann, H. P., Schierle, J., and van Loon, A. P.
TITLE	:	Isolation and characterization of the carotenoid biosynthesis genes of Flavobacterium sp. strain R1534 PubMed ID:9034310
JOURNAL	:	Gene.
VOL	:	185 PAGE : 35-41 (1997)

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[0205]

AUTHOR	:	Fraser, P. D., Miura, Y., and Misawa, N.
TITLE	:	In vitro characterization of astaxanthin biosynthetic enzymes PubMed ID:9045623
JOURNAL	:	J Biol Chem.
VOL	:	272 PAGE : 6128-6135 (1997)

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AUTHOR	:	Fraser, P. D., Misawa, N., Linden, H., Yamano, S., Kobayashi, K., and Sandmann, G.
TITLE	:	Expression in Escherichia coli, purification, and reactivation of the recombinant Erwinia uredovora phytoene desaturase PubMed ID:1400305
JOURNAL	:	J Biol Chem.
VOL	:	267 PAGE : 19891-19895 (1992)

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[0208]

AUTHOR	:	Yokoyama, A., and Miki, W.
TITLE	:	Composition and Presumed Biosynthetic Pathway of Carotenoids in the Astaxanthin-Producing Bacterium Agrobacterium aurantiacum
JOURNAL	:	FEMS Microbiol. Lett.
VOL	:	128 PAGE : 139-144 (1995)

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[0213]

AUTHOR	:	Jyonouchi, H., Zhang, L., and Tomita, Y.
TITLE	:	Studies of immunomodulating actions of carotenoids. II. Astaxanthin enhances in vitro antibody production to T-dependent antigens without facilitating polyclonal B-cell activation PubMed ID:8346076
JOURNAL	:	Nutr Cancer.
VOL	:	19 PAGE : 269-280 (1993)

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AUTHOR	:	Mathews-Roth,M.M.
TITLE	:	Recent Progress in the Medical Applications of Carotenoid
JOURNAL	:	Pure Appl. Chem.
VOL	:	63 PAGE : 147-156 (1991)

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AUTHOR	:	Miki,W.
TITLE	:	Biological Functions and Activities of Animal Carotenoids
JOURNAL	:	Pure Appl. Chem.
VOL	:	63 PAGE : 141-146 (1991)

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AUTHOR	:	Matsuno,T.
TITLE	:	Xanthophylls as Precursors of Retinoids
JOURNAL	:	Pure Appl. Chem.
VOL	:	63 PAGE : 81-88 (1991)

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AUTHOR	:	Tsushima, M., Maoka, T., Katsuyama, M., Kozuka, M., Matsuno, T., Tokuda, H., Nishino, H., and Iwashima, A.
TITLE	:	Inhibitory effect of natural carotenoids on Epstein-Barr virus activation activity of a tumor promoter in Raji cells. A screening study for anti-tumor promoters PubMed ID:7742789
JOURNAL	:	Biol Pharm Bull.
VOL	:	18 PAGE : 227-233 (1995)

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AUTHOR	:	Tanaka, T., Morishita, Y., Suzui, M., Kojima, T., Okumura, A., and Mori, H.
TITLE	:	Chemoprevention of mouse urinary bladder carcinogenesis by the naturally occurring carotenoid astaxanthin PubMed ID:8293542
JOURNAL	:	Carcinogenesis.
VOL	:	15 PAGE : 15-19 (1994)

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AUTHOR	:	Tanaka, T., Makita, H., Ohnishi, M., Mori, H., Satoh, K., and Hara, A.
TITLE	:	Chemoprevention of rat oral carcinogenesis by naturally occurring xanthophylls, astaxanthin and canthaxanthin PubMed ID:7664280
JOURNAL	:	Cancer Res.
VOL	:	55 PAGE : 4059-4064 (1995)

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AUTHOR	:	Alberte, R. S., Friedman, A. L., Gustafson, D. L., Rudnick, M. S., and Lyman, H.
TITLE	:	Light-harvesting systems of brown algae and diatoms. Isolation and characterization of chlorophyll a/c and chlorophyll a/fucoxanthin pigment-protein complexes PubMed ID:7016188
JOURNAL	:	Biochim Biophys Acta.
VOL	:	635 PAGE : 304-316 (1981)

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AUTHOR	:	Hofmann, E., Wrench, P. M., Sharples, F. P., Hiller, R. G., Welte, W., and Diederichs, K.
TITLE	:	Structural basis of light harvesting by carotenoids: peridinin-chlorophyll-protein from Amphidinium carterae PubMed ID:8650577
JOURNAL	:	Science.
VOL	:	272 PAGE : 1788-1791 (1996)

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AUTHOR	:	Sharples, F. P., Wrench, P. M., Ou, K., and Hiller, R. G.
TITLE	:	Two distinct forms of the peridinin-chlorophyll a-protein from Amphidinium carterae PubMed ID:8816945
JOURNAL	:	Biochim Biophys Acta.
VOL	:	1276 PAGE : 117-123 (1996)

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AUTHOR	:	Nishino, H., Tsushima, M., Matsuno, T., Tanaka, Y., Okuzumi, J., Murakoshi, M., Satomi, Y., Takayasu, J., Tokuda, H., Nishino, A., et al.
TITLE	:	Anti-neoplastic effect of halocynthiaxanthin, a metabolite of fucoxanthin PubMed ID:1450444
JOURNAL	:	Anticancer Drugs.
VOL	:	3 PAGE : 493-497 (1992)

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AUTHOR	:	Loya, S., Kashman, Y., and Hizi, A.
TITLE	:	The carotenoid halocynthiaxanthin: a novel inhibitor of the reverse transcriptases of human immunodeficiency viruses type 1 and type 2 PubMed ID:1371377
JOURNAL	:	Arch Biochem Biophys.
VOL	:	293 PAGE : 208-212 (1992)

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AUTHOR	:	Woodall, A. A., Britton, G., and Jackson, M. J.
TITLE	:	Carotenoids and protection of phospholipids in solution or in liposomes against oxidation by peroxyl radicals: relationship between carotenoid structure and protective ability PubMed ID:9367186
JOURNAL	:	Biochim Biophys Acta.
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AUTHOR	:	Carpenter, K. L., van der Veen, C., Hird, R., Dennis, I. F., Ding, T., and Mitchinson, M. J.
TITLE	:	The carotenoids beta-carotene, canthaxanthin and zeaxanthin inhibit macrophage-mediated LDL oxidation PubMed ID:9013900
JOURNAL	:	FEBS Lett.
VOL	:	401 PAGE : 262-266 (1997)

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AUTHOR	:	Steghens, J. P., van Kappel, A. L., Riboli, E., and Collombel, C.
TITLE	:	Simultaneous measurement of seven carotenoids, retinol and alpha-tocopherol in serum by high-performance liquid chromatography PubMed ID:9234850
JOURNAL	:	J Chromatogr B Biomed Sci Appl.
VOL	:	694 PAGE : 71-81 (1997)

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AUTHOR	:	Bui, M. H.
TITLE	:	Simple determination of retinol, alpha-tocopherol and carotenoids (lutein, all-trans-lycopene, alpha- and beta-carotenes) in human plasma by isocratic liquid chromatography PubMed ID:8004234
JOURNAL	:	J Chromatogr B Biomed Appl.
VOL	:	654 PAGE : 129-133 (1994)

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AUTHOR	:	Narisawa, T., Fukaura, Y., Hasebe, M., Ito, M., Aizawa, R., Murakoshi, M., Uemura, S., Khachik, F., and Nishino, H.
TITLE	:	Inhibitory effects of natural carotenoids, alpha-carotene, beta-carotene, lycopene and lutein, on colonic aberrant crypt foci formation in rats PubMed ID:8913278
JOURNAL	:	Cancer Lett.
VOL	:	107 PAGE : 137-142 (1996)

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AUTHOR	:	Shimidzu,N.,Goto,M., and Miki,W.
TITLE	:	Carotenooids as Singlet Oxygen Quenchers in Marine Organisms.
JOURNAL	:	Fisheries Sci.
VOL	:	62 PAGE : 134-137 (1996)

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AUTHOR	:	Kobayashi, T., Iijima, K., Mitamura, T., Toriizuka, K., Cyong, J. C., and Nagasawa, H.
TITLE	:	Effects of lycopene, a carotenoid, on intrathymic T cell differentiation and peripheral CD4/CD8 ratio in a high mammary tumor strain of SHN retired mice PubMed ID:8740725
JOURNAL	:	Anticancer Drugs.
VOL	:	7 PAGE : 195-198 (1996)

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AUTHOR	:	Pecker, I., Gabbay, R., Cunningham, F. X., Jr., and Hirschberg, J.
TITLE	:	Cloning and characterization of the cDNA for lycopene beta-cyclase from tomato reveals decrease in its expression during fruit ripening PubMed ID:8624411
JOURNAL	:	Plant Mol Biol.
VOL	:	30 PAGE : 807-819 (1996)

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AUTHOR	:	To, K. Y., Lai, E. M., Lee, L. Y., Lin, T. P., Hung, C. H., Chen, C. L., Chang, Y. S., and Liu, S. T.
TITLE	:	Analysis of the gene cluster encoding carotenoid biosynthesis in Erwinia herbicola Eho13 PubMed ID:8180698
JOURNAL	:	Microbiology.
VOL	:	140 (Pt 2) PAGE : 331-339 (1994)

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AUTHOR	:	Cunningham, F. X., Jr., Chamovitz, D., Misawa, N., Gantt, E., and Hirschberg, J.
TITLE	:	Cloning and functional expression in Escherichia coli of a cyanobacterial gene for lycopene cyclase, the enzyme that catalyzes the biosynthesis of beta-carotene PubMed ID:8344419
JOURNAL	:	FEBS Lett.
VOL	:	328 PAGE : 130-138 (1993)

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AUTHOR	:	Okuzumi, J., Nishino, H., Murakoshi, M., Iwashima, A., Tanaka, Y., Yamane, T., Fujita, Y., and Takahashi, T.
TITLE	:	Inhibitory effects of fucoxanthin, a natural carotenoid, on N-myc expression and cell cycle progression in human malignant tumor cells PubMed ID:2245414
JOURNAL	:	Cancer Lett.
VOL	:	55 PAGE : 75-81 (1990)

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[0236]

AUTHOR	:	Murakoshi, M., Nishino, H., Satomi, Y., Takayasu, J., Hasegawa, T., Tokuda, H., Iwashima, A., Okuzumi, J., Okabe, H., Kitano, H., et al.
TITLE	:	Potent preventive action of alpha-carotene against carcinogenesis: spontaneous liver carcinogenesis and promoting stage of lung and skin carcinogenesis in mice are suppressed more effectively by alpha-carotene than by beta-carotene PubMed ID:1423303
JOURNAL	:	Cancer Res.
VOL	:	52 PAGE : 6583-6587 (1992)

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AUTHOR	:	Milon,A.,Wolff,G.,Ourisson,G., and Nakatani,Y.
TITLE	:	Organization of Carotenoid-Phospholipid Bilayer Systems. Incorporation of Zeaxanthin, Astaxanthin, and their C50 Homologues into Dimyristoylphosphatidylcholine Vesicles.
JOURNAL	:	Helv. Chim. Acta
VOL	:	69 PAGE : 12-24 (1986)

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AUTHOR	:	Bjerkeng,B., Hertzberg,S., and Liaaen-Jensen,S.
TITLE	:	Carotenoids in Food Chain Studies - V. Carotenoids of the Bivalves Modiolus Modiolus and Pecten maximus - Structural, Metabolic and Food Chain Aspects.
JOURNAL	:	Comp. Biochem. Physiol.
VOL	:	106 PAGE : 243-250 (1993)

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AUTHOR	:	Ookubo,M., and Matsuno,T.,
TITLE	:	Carotenoids of sea squirts - II. Comparative biochemical studies of carotenoids in sea squirts
JOURNAL	:	Comp. Biochem. Physiol.
VOL	:	81 PAGE : 137-141 (1985)

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AUTHOR	:	Matsuno,T. and Ookubo,M.
TITLE	:	A new carotenoid, halocynthiaxanthin from the sea squirt, Halocynthia roretzi
JOURNAL	:	Tetrahedron Lett.
VOL	:	22 PAGE : 4659-4660 (1981)

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AUTHOR	:	Matsuno,T.,Maoka,T.,Shiba,K., and Ookubo,M.
TITLE	:	Isolation of fucoxanthinol from short-necked clam Tapes philippinarum [Asari in Japanese]
JOURNAL	:	Bull. Jap. Soc. Sci. Fish.
VOL	:	52 PAGE : 167-167 (1986)

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[0404]

AUTHOR	:	Partali,V.,Tangen,K., and Liaaen-Jensen,S.
TITLE	:	Carotenoids in food chain studies - III Resorption and metabolic transformation of carotenoids in Mytilus edulis (Edible mussel)
JOURNAL	:	Comp. Biochem. Physiol.
VOL	:	92 PAGE : 239-246 (1989)

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[0405]

AUTHOR	:	Maoka,T.,Arai,A.,Shimizu,M., and Matsuno,T.
TITLE	:	The first isolation of enantiomeric and meso-zeaxanthin in nature
JOURNAL	:	Comp. Biochem. Physiol.
VOL	:	83 PAGE : 121-124 (1986)

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AUTHOR	:	Schiedt,K.,Leuenberger,F.J.,Vecchi,M., and Glinz,E.
TITLE	:	Absorption, retention and metabolic transformations of carotenoids in rainbow trout, salmon and chicken
JOURNAL	:	Pure Appl. Chem.
VOL	:	57 PAGE : 685-692 (1985)

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AUTHOR	:	Schiedt,K.,Vecchi,M.,Glinz,E., and Storebakken,T.
TITLE	:	Metabolism of carotenoids in salmonids Metabolism of astaxanthin and canthaxanthin in the skin of atlantic salmon (Salmo salar, L.)
JOURNAL	:	Helv. Chim. Acta
VOL	:	71 PAGE : 887-896 (1988)

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AUTHOR	:	Matsuno,T., Katsuyama,M., Maoka,T., Hirono,T., and Komori,T.
TITLE	:	Reductive metabolic pathways of carotenoids in fish (3S, 3'S)-astaxanthin to tunaxanthin A, B and C
JOURNAL	:	Comp. Biochem. Physiol.
VOL	:	80 PAGE : 779-789 (1985)

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AUTHOR	:	Goodwin T. W. (1980) The biochemistry of the carotenoids, Volume I, Plants, Chapman and Hall, London and New York
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AUTHOR	:	Goodwin T. W. (1984) The biochemistry of the carotenoids, Volume II, Animals, Chapman and Hall, London and New York
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AUTHOR	:	Matsuno, T. and Hirao, S. (1989) Marine carotenoids, In Marine Biogenic Lipids, Fats, and Oils (Edited by Ackman, R.G.) Vol. 1, pp 251-388, CRC Press, Boca Raton, FL.
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AUTHOR	:	Egger,K.
TITLE	:	Die Ketocarotinide In Adonis annua L.
JOURNAL	:	Phytochemistry
VOL	:	4 PAGE : 609-618 (1965)

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AUTHOR	:	Matsuno,T.,Kusumoto,T.,Watanabe,T., and Ishihara,Y.
TITLE	:	Carotenoid pigments of spiny lobster
JOURNAL	:	Bull. Jap. Soc. Sci. Fish.
VOL	:	39 PAGE : 43-50 (1973)

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[0415]

AUTHOR	:	Matsuno,T.,Matsutaka,H., and Nagata,S.
TITLE	:	Metabolism of lutein and zeaxanthin to ketocarotenoids in goldfish, Carassius auratus
JOURNAL	:	Bull. Jap. Soc. Sci. Fish.
VOL	:	47 PAGE : 605-611 (1981)

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[0416]

AUTHOR	:	Matsuno,T., and Nagata,S.
TITLE	:	Biosynthesis of characteristic, principal carotenoids of the Japanese common catfish, parasiloxanthin (7',8'-dihydrozeaxanthin) and 7,8-dihydroparasiloxanthin
JOURNAL	:	Bull. Jap. Soc. Sci. Fish.
VOL	:	46 PAGE : 1363-1367 (1980)

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AUTHOR	:	Katsuyama,M., and Matsuno,T.
TITLE	:	Carotenoid and vitanin A, and metabplism of carotenoids, b-carotene, canthaxanthin, astaxanthin, zeaxanthin, lutein and tunaxanthin in tilapia Tilapia nilotica
JOURNAL	:	Comp. Biochem. Physiol.
VOL	:	90 PAGE : 131-139 (1988)

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AUTHOR	:	Rønneberg,H.,Renstrom,B.,Aareskjold,K.,Liaaen-Jensen,S.,Veechi,M.,Leuenberger,F.J.,Müller,R.K., and Mayer,H.
TITLE	:	Natural occurrence of enatiomeric and meso-astaxanthin 1. Ex Lobster Eggs (Homarus gammarus)
JOURNAL	:	Helv. Chim. Acta
VOL	:	63 PAGE : 711-715 (1980)

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AUTHOR	:	Schiedt,K.,Leuenberger,F.J., and Vecchi,M.
TITLE	:	Natural Occurrences of enantiomeric and meso-astaxanthin 5, Ex Wild salmon (Salmo salar and Oncorynchus)
JOURNAL	:	Helv. Chim. Acta
VOL	:	64 PAGE : 449-457 (1981)

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AUTHOR	:	Bernhard,K.,Englert,G.,Meister,W.Vecchi,M.,Renstrom,B., and Liaaen-Jensen,S.
TITLE	:	Carotenoids of the carotenoprotein asteriarubin. Optical purity of asterinic acid
JOURNAL	:	Helv. Chim. Acta
VOL	:	65 PAGE : 2224-2229 (1982)

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AUTHOR	:	Matsuno,T.,Maoka,T.,Katsuyama, M.,Ookubo,M.,Katagiri,K., and Jimura,H.
TITLE	:	The occurence of enantiomeric and meso-astaxanthin in aquatic animals
JOURNAL	:	Bull. Jap. Soc. Sci. Fish.
VOL	:	50 PAGE : 1589-1592 (1984)

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[0422]

AUTHOR	:	Maoka,T.,Katsuyama,M.,Kaneko,N., and Matsuno,T.
TITLE	:	Stereochemical investigation of the carotenoids in the antarctic krill Euphausia superba
JOURNAL	:	Bull. Jap. Soc. Sci. Fish.
VOL	:	51 PAGE : 1671-1673 (1985)

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[0423]

AUTHOR	:	Maoka,T.,Tsushima,M., and Matsuno,T.
TITLE	:	New acetylenic carotenoids from the starfishes Asterina pectinifera and Asterias amurensis
JOURNAL	:	Comp. Biochem. Physiol.
VOL	:	93 PAGE : 829-834 (1989)

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[0424]

AUTHOR	:	Maoka,T.,Yokoi,S., and Matsuno,T.
TITLE	:	Comparative biochemical studies of carotenoids in nine species of cephalopoda
JOURNAL	:	Comp. Biochem. Physiol.
VOL	:	92 PAGE : 247-250 (1989)

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AUTHOR	:	Andrewes,A.G., and Starr,M.P.
TITLE	:	(3R,3'R)-Astaxanthin from the yeast Phaffia rhodozyma
JOURNAL	:	Phytochemistry
VOL	:	15 PAGE : 1009-1011 (1976)

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AUTHOR	:	Hertzberg,S.,Partali,V., and Liaaen-Jensen,S.
TITLE	:	Animal carotenoids. 32. Carotenoids of Mytilus edulis (Edible mussel)
JOURNAL	:	Acta Chem. Scand.
VOL	:	42 PAGE : 495-503 (1988)

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[0427]

AUTHOR	:	Matsuno,T., and Maoka,T.
TITLE	:	Isolation of a new carotenoid, 3,4,3'-trihydroxy-7',8'-didehydro-b-carotene-3,4,3'-triol from dea mussels
JOURNAL	:	Bull. Jap. Soc. Sci. Fish.
VOL	:	47 PAGE : 377-384 (1981)

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[0428]

AUTHOR	:	Matsuno,T.,Hirono,T.,Ikuno,Y.,Maoka,T.,Shimizu,M., and Komori,T.
TITLE	:	Isolation of three new carotenoids and proposed metabolic payhways of carotenoids in hen's egg yolk
JOURNAL	:	Comp. Biochem. Physiol.
VOL	:	84 PAGE : 477-481 (1986)

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[0429]

AUTHOR	:	Partali,V.,Liaaen-Jensen,S., Slagsvold,T., and Lifjeld,J.T.
TITLE	:	Carotenoids in food chain studies - II. The food chain of Parus spp. monitored by carotenoid analysis
JOURNAL	:	Comp. Biochem. Physiol.
VOL	:	87 PAGE : 885-888 (1987)

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[0430]

AUTHOR	:	Fujita,T.,Satake,M.,Hikichi,S.,Takeda,M.,Shimeno,S.,Kuwabara,H.,Miki,W.,Yamaguchi,K., and Konosu,S.
TITLE	:	Pigmentation of cultured yellowtail with krill oil
JOURNAL	:	Bull. Jap. Soc. Sci. Fish.
VOL	:	49 PAGE : 1595-1600 (1983)

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[0431]

AUTHOR	:	Yamaguchi,K., Miki,W., Toriu, N., Kondo,Y., Murakami,M., Konosu,S., Satake,M., and Fujita,T.
TITLE	:	The composition of carotenoid pigments in the antarctic krill Euphausia superba
JOURNAL	:	Bull. Jap. Soc. Sci. Fish.
VOL	:	49 PAGE : 1411-1415 (1983)

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[0432]

AUTHOR	:	Fujita,T.,Satake,M.,Watanabe,T.,Kitajima,C.,Miki,W.,Yamaguchi,K., and Konosu,S.
TITLE	:	Pigmentation of cultured red sea bream with astaxanthin diester purified from krill oil
JOURNAL	:	Bull. Jap. Soc. Sci. Fish.
VOL	:	49 PAGE : 1855-1861 (1983)

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[0434]

AUTHOR	:	Khare,A.,Moss,G.P., and Weedon,B.C.L.
TITLE	:	Mytiloxanthin and isomytiloxanthin, two novel acetylenic carotenoids
JOURNAL	:	Tetrahedron Lett.
VOL	:	PAGE : 3921-3924 (1973)

[TOP]

[0435]

AUTHOR	:	Miki,W.,Yamaguchi,K.,Konosu,S.,Takane,T.,Satake,M.,Fujita,T.,Kuwabara,H.,Shimeno,S., and Takeda,M.
TITLE	:	Origin of tunaxaqnthin in the integument pf yellowtail (Seriola quinqueradiata)
JOURNAL	:	Comp. Biochem, Physiol.
VOL	:	80 PAGE : 195-201 (1985)

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[0436]

AUTHOR	:	Miki,W.,Yamaguchi,K.,Konosu,S., and Watanabe,T.
TITLE	:	Metabolism of dietary carotenoids in eggs of red sea bream
JOURNAL	:	Comp. Biochem. Physiol.
VOL	:	77 PAGE : 665-668 (1984)

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[0437]

AUTHOR	:	Burton, G. W., and Ingold, K. U.
TITLE	:	beta-Carotene: an unusual type of lipid antioxidant PubMed ID:6710156
JOURNAL	:	Science.
VOL	:	224 PAGE : 569-573 (1984)

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[0438]

AUTHOR	:	Foote,C.S., and Denny,R.W.
TITLE	:	Chemistry of Singlet Oxygen. VII. Quenching by b-carotene
JOURNAL	:	J. Am. Chem. Soc.
VOL	:	90 PAGE : 6233-6235 (1968)

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[0441]

AUTHOR	:	Hirayama, O., Nakamura, K., Hamada, S., and Kobayasi, Y.
TITLE	:	Singlet oxygen quenching ability of naturally occurring carotenoids PubMed ID:8152349
JOURNAL	:	Lipids.
VOL	:	29 PAGE : 149-150 (1994)

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[0450]

AUTHOR	:	Märki-Fischer,E., and Eugster,C.H.
TITLE	:	Eine weitere, diesmal erfolgreiche Suche nach 3'-Epilutein in Pflanzen
JOURNAL	:	Helv. Chim. Acta
VOL	:	73 PAGE : 1205-1209 (1990)

[TOP]

[0451]

AUTHOR	:	Matsuno,T.,Wakasa,W., and Ookubo,M.
TITLE	:	Carotenoids of River Crab Potamon dehaani
JOURNAL	:	Bull. Jap. Soc. Sci. Fish.
VOL	:	48 PAGE : 661-666 (1982)

[TOP]

[0452]

AUTHOR	:	Matsuno, T., Maoka, T., Katsuyama, M., Hirono, T., Ikuno, Y., Shimizu, M., and Komori, T.
TITLE	:	Comparative biochemical studies of carotenoids in fishes--XXIX. Isolation of new luteins, lutein F and lutein G from marine fishes PubMed ID:3769462
JOURNAL	:	Comp Biochem Physiol B.
VOL	:	85 PAGE : 77-80 (1986)

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[0453]

AUTHOR	:	Dabbagh,A.G., and Egger,K.
TITLE	:	Calthaxanthin-Ein Stereoisomers des Lutein aus Caltha palustris
JOURNAL	:	Z. Pflanzenphysiol.
VOL	:	72 PAGE : 177-180 (1974)

[TOP]

[0454]

AUTHOR	:	Matsuno,T., and Tsushima,M.
TITLE	:	Comparative biochemical studies of carotenoids in sea cucumbers
JOURNAL	:	Comp. Biochem. Physiol.
VOL	:	111 PAGE : 597-605 (1995)

[TOP]

[0455]

AUTHOR	:	Matsuno,T.,Matsutaka,H.,Katsuyama,M., and Nagata,S.
TITLE	:	Occurrence of 3'-Epimer of Lutein (Calthaxanthin, 3'-Epilutein) from Fishes
JOURNAL	:	Bull. Jap. Soc. Sci. Fish.
VOL	:	46 PAGE : 337-340 (1980)

[TOP]

[0456]

AUTHOR	:	Maoka,T.,Masuda,M.,Ikuno,Y., and Matsuno,T.
TITLE	:	The First Isolation and Identification of Tunaxanthin G and Tunaxanthin H from Carp Cyprinus carpio
JOURNAL	:	Bull. Jap. Soc. Sci. Fish.
VOL	:	52 PAGE : 357- (1986)

[TOP]

[0457]

AUTHOR	:	Matsuno,T., and Yamashita,E.
TITLE	:	The First Isolation and Identification of the tenth Stereoisomer of Tunaxanthin, Tunaxanthin E from the Biwa Goby Chaenogobius isaza
JOURNAL	:	Nippon Suisan Gakkaishi
VOL	:	55 PAGE : 1667- (1989)

[TOP]

[0458]

AUTHOR	:	Matsuno,T.,Matsutaka,H.,Katsuyama,M., and Nagata,S.
TITLE	:	Isolation of Three Stereoisomers, Tunaxanthin A, Tunaxanthin B and Tunaxanthin C ftom Tunaxanthin Fraction in the Integuments of Fishes
JOURNAL	:	Bull. Jap. Soc. Sci. Fish.
VOL	:	46 PAGE : 333-336 (1980)

[TOP]

[0459]

AUTHOR	:	Ronneberg,H.,Borch,G.,Liaaen-Jensen,S.,Matsutaka,H., and Matsuno,T.,
TITLE	:	Animal Carotenoids. 16. Tunaxanthin
JOURNAL	:	Acta Chem. Scand.
VOL	:	32 PAGE : 621-623 (1978)

[TOP]

[0460]

AUTHOR	:	Maoka,T.,Ito,Y.,Fujiwara,Y., and Hashimoto,K.
TITLE	:	Structures and Antioxidative Activity of retro Carotenoids from the Berries of the Japanese Yew, Taxus cuspidata
JOURNAL	:	J. Jap. Oil Chem. Soc.
VOL	:	45 PAGE : 641-646 (1996)

[TOP]

[0461]

AUTHOR	:	Strain H.H.
TITLE	:	Eschscholtzxanthin : A New Xanthophyll from the Petals of the california poppy, Eschscholtzia californica
JOURNAL	:	J. Biol. Chem.
VOL	:	123 PAGE : 425-437 (1938)

[TOP]

[0462]

AUTHOR	:	Kuhn,R., and Brockmann,H.
TITLE	:	über Rhodoxanthin""
JOURNAL	:	Ber. Dtsch. Chem. Ges.
VOL	:	66 PAGE : 828-834 (1933)

[TOP]

[0463]

AUTHOR	:	Kayser,H.
TITLE	:	Hormon Induced Changes in Carotenoid Composition in Ricinus Cell Cultures. I. Identification of Rhodoxanthin
JOURNAL	:	Z. Naturforsch.
VOL	:	39 PAGE : 50-54 (1984)

[TOP]

[0464]

AUTHOR	:	Diaz,M.,Ball,E., and Luttge,U.
TITLE	:	Stress-induced accumulation of the xanthophyll rhodoxanthin in leaves of Aloe vera
JOURNAL	:	Plant Physiol. Biochem.
VOL	:	28 PAGE : 679-682 (1990)

[TOP]

[0465]

AUTHOR	:	Ida,K.,Saito,F., and Takeda,S.
TITLE	:	Isomers of Rhodoxanthin in Reddish Brown Leaves of Gymnosoerms and Effect of Daylight Intensity on the Contents of Pigments during Autumnal Coloration
JOURNAL	:	Bot. Mag. Tokyo
VOL	:	104 PAGE : 157-169 (1991)

[TOP]

[0466]

AUTHOR	:	Matsuno,T., and Katsuyama,M.
TITLE	:	Comparative Biochemical Studies of Carotenoids in Fishes-XIV. Carotenoids of Tilapia-I
JOURNAL	:	Bull. Jap. Soc. Sci. Fish.
VOL	:	45 PAGE : 1533-1538 (1979)

[TOP]

[0467]

AUTHOR	:	Matsuno,T., and Katsuyama,M.
TITLE	:	Metabolism of Zeaxanthin to Rhodoxanthin in Tilapia Tilapia nilotica
JOURNAL	:	Bull. Jap. Soc. Sci. Fish.
VOL	:	48 PAGE : 1491-1493 (1982)

[TOP]

[0468]

AUTHOR	:	Costes,C.
TITLE	:	Sur la presence d'anhydroeschscholtzxanthin dans les feuilles rouges de buis, Buxus semperivirens
JOURNAL	:	Bull. Soc. Franc. Physiol. Veget.
VOL	:	15 PAGE : 55-77 (1969)

[TOP]

[0469]

AUTHOR	:	Matsuno,T., and Maoka,T.
TITLE	:	The Carotenoids of Crab Paralithodes brevipes (Hanasakigani in Japanese)
JOURNAL	:	Nippon Suisan Gakkaishi
VOL	:	54 PAGE : 1437-1442 (1988)

[TOP]

[0470]

AUTHOR	:	Matsuno,T., and Matsutaka,M.
TITLE	:	Carotenoids of Four Species of Crucian Carp and Two Varieties of Goldfish
JOURNAL	:	Bull. Jap. Soc. Sci. Fish.
VOL	:	47 PAGE : 85-88 (1981)

[TOP]

[0471]

AUTHOR	:	Bullock,E., and Dawson,C.H.
TITLE	:	Carotenoid pigments of the holothurian Psolus fabrichii DüBEN and KOREN (The scarlet psolus)""
JOURNAL	:	Comp. Biochem. Pysiol.
VOL	:	34 PAGE : 799-804 (1970)

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[0472]

AUTHOR	:	Matsuno.T.,Katsuyma,M., and Nagata,S.
TITLE	:	Comparative Biochemical Studies of Carotenoids in Fishes - XIX Carotenoids of Chum Salmon, Coho Salmon, Biwa Trout, Red-spotted Masu Salmon, Masu Salmon, and Kokanee
JOURNAL	:	Bull. Jap. Soc. Sci. Fish.
VOL	:	46 PAGE : 879-884 (1980)

[TOP]

[0473]

AUTHOR	:	Matsuno,T.,Nagata.,S.,Katsuyama,M.,Matsutaka,H.,Maoka,M., and Akita,T.
TITLE	:	Comparative Biochemical Studies of Carotenoids in Fishes - XVIII Carotenoids of Cultured Fishes, Japanese Char, Brook Trout, Lake Trout, Masu Trout, Red-Spotted Masu Ttout, Rainbow Trout and Brown Trout
JOURNAL	:	Bull. Jap. Soc. Sci. Fish.
VOL	:	46 PAGE : 473-478 (1980)

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[0474]

AUTHOR	:	Englert,G., and Vecchi,M.
TITLE	:	High-performance liquid chromatographic separation and proton nuclear magnetic resonance identification of the 6-mono-cis and 6,6'-di-cis-isomers of rhodoxanthin
JOURNAL	:	J. Chromatogr.
VOL	:	235 PAGE : 197-203 (1982)

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[0475]

AUTHOR	:	Tsushima,M., and Matsuno,T.
TITLE	:	Carotenoid Composition and Two New 4-ketolutein Isomers in the Integuments of the Red Tilefish Branchiostegus japonicus
JOURNAL	:	Fisheries Science
VOL	:	64 PAGE : 464-468 (1998)

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[0476]

AUTHOR	:	Fox, D. L., and Hopkins, T. S.
TITLE	:	Comparative metabolic fractionation of carotenoids in three flamingo species PubMed ID:5943916
JOURNAL	:	Comp Biochem Physiol.
VOL	:	17 PAGE : 841-856 (1966)

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[0477]

AUTHOR	:	Fox,D.L., and Hopkins,T.S.
TITLE	:	Carotenoid fractionation in the scarlet ibis
JOURNAL	:	Comp. Biochem. Physiol.
VOL	:	19 PAGE : 267-278 (1966)

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[0478]

AUTHOR	:	Herring, P. J.
TITLE	:	The carotenoid pigments of Daphnia magna Straus. I. The pigments of animals fed.Chlorella pyrenoidosa and pure carotenoids PubMed ID:4296346
JOURNAL	:	Comp Biochem Physiol.
VOL	:	24 PAGE : 187-203 (1968)

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[0479]

AUTHOR	:	Krinsky, N. I., and Lenhoff, H. M.
TITLE	:	Some carotenoids in Hydra PubMed ID:4379504
JOURNAL	:	Comp Biochem Physiol.
VOL	:	16 PAGE : 189-198 (1965)

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[0480]

AUTHOR	:	Fox,D.L.,Wolfson,A.A., and McBeth,J.W.
TITLE	:	Metabolism of b-carotene in the american flamingo, Phoenicopterus ruber
JOURNAL	:	Comp. Biochem. Physiol.
VOL	:	29 PAGE : 1223-1229 (1969)

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[0481]

AUTHOR	:	Herring, P. J.
TITLE	:	The carotenoid pigments of Daphnia magna Straus. II. Aspects of pigmentary metabolism PubMed ID:5645509
JOURNAL	:	Comp Biochem Physiol.
VOL	:	24 PAGE : 205-221 (1968)

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[0482]

AUTHOR	:	Davies, B. H., Hsu, W. J., and Chichester, C. O.
TITLE	:	The mechanism of the conversion of beta-carotene into canthaxanthin by the brine shrimp, Artemia salina L. (Crustacea: Branchiopoda) PubMed ID:5445744
JOURNAL	:	Comp Biochem Physiol.
VOL	:	33 PAGE : 601-615 (1970)

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[0483]

AUTHOR	:	Hata,M., and Hata,M.
TITLE	:	Carotenoid metabolism in Artemia salina L.
JOURNAL	:	Comp. Biochem. Physiol.
VOL	:	29 PAGE : 985-994 (1969)

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[0484]

AUTHOR	:	Murugan,G.,Nelis,H.J.,Dumot,H.J., and De Leenheer,A.P.
TITLE	:	Cis- and all-trans-canthaxanthin levels in fairy shrimps
JOURNAL	:	Comp. Biochem. Physiol.
VOL	:	110 PAGE : 799-803 (1995)

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AUTHOR	:	Guillou,A.,Choubert,G.,Storebakken,T.,De La Noüe,J., and Kaushik,S.
TITLE	:	Bioconversion pathway of astaxanthin into retinol₂ in mature rainbow trout (Salmo gairdneri Rich.)
JOURNAL	:	Comp. Biochem. Physiol.
VOL	:	94 PAGE : 484-485 (1989)

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[0489]

AUTHOR	:	Palozza, P., and Krinsky, N. I.
TITLE	:	Astaxanthin and canthaxanthin are potent antioxidants in a membrane model PubMed ID:1497349
JOURNAL	:	Arch Biochem Biophys.
VOL	:	297 PAGE : 291-295 (1992)

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[0490]

AUTHOR	:	Palozza, P., Luberto, C., Ricci, P., Sgarlata, E., Calviello, G., and Bartoli, G. M.
TITLE	:	Effect of beta-carotene and canthaxanthin on tert-butyl hydroperoxide-induced lipid peroxidation in murine normal and tumor thymocytes PubMed ID:8561491
JOURNAL	:	Arch Biochem Biophys.
VOL	:	325 PAGE : 145-151 (1996)

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[0491]

AUTHOR	:	Yamauchi,R., and Kato,K.
TITLE	:	Products Formed by Peroxyl Radical-Mediated Oxidation of Canthaxanthin in Benzen and in Methyl linolate
JOURNAL	:	J. Agric. Food. Chem.
VOL	:	46 PAGE : 5006-5071 (1998)

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[0492]

AUTHOR	:	Murasecco-Suardi,P.,Oliveros,E., and Braun,A.M.
TITLE	:	Singlet-Oxygen Quenching by Carotenoids:Steady-State Luminescence Experiments
JOURNAL	:	Helv. Chim. Acta.
VOL	:	71 PAGE : 1005-1010 (1988)

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[0493]

AUTHOR	:	Tsuchiya,T., and Suzuki,Y.
TITLE	:	Biochemical studies of the ascidian, Cynthia roreti V. DRASHE IV. Carotenoids in test.
JOURNAL	:	Tohoku J. Agr. Res.
VOL	:	10 PAGE : 397-405 (1960)

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[0494]

AUTHOR	:	Matsuno,T.,Hiraoka,K., and Maoka,T.
TITLE	:	Carotenoids in the Gonad of Scallop
JOURNAL	:	Bull. Jap. Soc. Sci. Fish.
VOL	:	47 PAGE : 385-390 (1981)

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[0495]

AUTHOR	:	Matsuno,T., and Maoka,T.,
TITLE	:	Isolation of Diatoxanthin, Pectenoxanthin, Pectenolone and a New Carotenoid, 3,4,3'-trihydroxy-7',8'-didehydro-b-carotene from Arkshell and related Three Species of Bivalves
JOURNAL	:	Bull. Jap. Soc. Sci. Fish.
VOL	:	47 PAGE : 495-499 (1981)

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[0496]

AUTHOR	:	Campbell,S.A.,Mallams,A.K.,Waight,E.S.,Weedon,B.C.L.,Barbier,M.,Lederer,E., and Salaque,A.
TITLE	:	Pectenoxanthin, cynthiaxanthin, and a new acetylenic carotenoid pectenolone
JOURNAL	:	Chem. Comm.
VOL	:	PAGE : 941-942 (1967)

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[0497]

AUTHOR	:	Pennington,F.,Guillard,R.R.L., and Liaaen-Jensen,S.
TITLE	:	Carotenoid Distribution Patterns in Bacillariophyceae (Diatoms)
JOURNAL	:	Biochem. System. Ecol.
VOL	:	16 PAGE : 589-592 (1988)

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[0498]

AUTHOR	:	Bjfrnland,T.,Guillard,R.R.L., and Liaaen-Jensen,S.
TITLE	:	Phaeocystis sp. clone 677-3 - a tropical Marine Planktonic Prymnesiophyte with fucoxanthin and 19'-acyloxyfucoxanthin as Chemosystematic Carotenoid Makers
JOURNAL	:	Biochem. Syst. Ecol.
VOL	:	16 PAGE : 445-452 (1988)

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[0500]

AUTHOR	:	Hallenstvet,M.,Pyberg,E., and Liaaen-Jensen,S.
TITLE	:	Animal carotenoids - XIV Carotenoids of Psammechinus miliaris (sea-urchin)
JOURNAL	:	Comp. Biochem. Physiol.
VOL	:	60 PAGE : 173-175 (1978)

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[0501]

AUTHOR	:	Tsushima,M.,Kawakami,T., and Matsuno,T.
TITLE	:	Metabolism of carotenoids in sea-urchin Pseudocentrotus depressus
JOURNAL	:	Comp. Biochem. Physiol.
VOL	:	106 PAGE : 737-741 (1993)

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[0502]

AUTHOR	:	Tsushima,M., and Matsuno,T.
TITLE	:	Comparative biochemical studies of carotenoids in sea-urchins: 1.
JOURNAL	:	Comp. Biochem. Physiol.
VOL	:	96 PAGE : 801-810 (1990)

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[0503]

AUTHOR	:	Tsushima,M.,Amemiya,S., and Matsuno,T.
TITLE	:	Comparative biochemical studies of carotenoids in sea-urchins -II. The more primitive sea-urchins belonging to the orders Cidaroida, Echinothuriodia, Diadematoida and Arbacioida
JOURNAL	:	Comp. Biochem. Physiol.
VOL	:	106 PAGE : 729-753 (1993)

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[0504]

AUTHOR	:	Parkes,K.E.B., and Pattenden,G.
TITLE	:	Novel carotenoid 3,6-epoxides from red paprika
JOURNAL	:	Tetrahedron Lett.
VOL	:	27 PAGE : 2535-2538 (1986)

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[0505]

AUTHOR	:	Deli,J.,Molnar,P., Matus,Z.,Toth,G., and Steck,A.
TITLE	:	Reisolation of Carotenoid 3,6-Epoxides feom Red Paprika (Capsicum annuum)
JOURNAL	:	Helv. Chim. Acta.
VOL	:	79 PAGE : 1435-1443 (1996)

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[0506]

AUTHOR	:	Deli,J.,Matus,Z., and Toth,G.
TITLE	:	Carotenoid Composition in the Fruits of Capsicum annuum Cv. Szentesi Kosszarvu during Ripening
JOURNAL	:	J. Agric. Food Chem.
VOL	:	44 PAGE : 711-716 (1996)

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[0507]

AUTHOR	:	Minguenz-Mosquera,M.I., and Hornero-Mendez,D.
TITLE	:	Separation and Quantification of the Carotenoid Pigments in Red Peppers (Capsicum annuum L.), Paprika, and Oleoresin by Reversed-Phase HPLC
JOURNAL	:	J. Agric. Food Chem.
VOL	:	41 PAGE : 1616-1620 (1993)

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AUTHOR	:	Deli,J.,Molnar,P.,Toth,G.,Baumeler,A., and Eugster,C.H.
TITLE	:	Cycloviolaxanthin (=(3S,5R,6R,3'S,5'R,6'R)-3,6:3',6'-Diepoxy-5,6,5',6'-tetrhydro-b,b-carotin-5,5'-diol), eine neues Carotinoid aus Paprika (Capsicum annuum)
JOURNAL	:	Helv. Chim. Acta
VOL	:	74 PAGE : 819-824 (1991)

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[0509]

AUTHOR	:	Molnar,P.,Deli,J.,Matus,Z.,Toth,G., and Steck,A.
TITLE	:	Isomerisierung von (all-E)-Cycloviolaxanthin Herstellung und Charakterisierung von (9Z)- und (13Z)-Cycloviolaxanthin
JOURNAL	:	Helv. Chim. Acta
VOL	:	79 PAGE : 1444-1450 (1996)

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[0510]

AUTHOR	:	Matsuno,T.,Tani,Y.,Maoka,T.,Matsuo,K., and Komori,T.
TITLE	:	Isolation and structural elucidation of cucurbitaxanthin A and B from pumpkin Cucurbita maxima
JOURNAL	:	Phytochemistry
VOL	:	25 PAGE : 2837-2840 (1986)

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[0511]

AUTHOR	:	Hornero-Mendez,D., and Minguez-Mosquera,M.,I.
TITLE	:	Isolation and Identification of the Carotenoid Capsolutein from Capsicum annuum as Cucurbitaxanthin A
JOURNAL	:	J. Agric. Food Chem.
VOL	:	46 PAGE : 4087-4090 (1998)

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AUTHOR	:	Yamamoto,H.Y.
TITLE	:	Biochemistry of the Violaxanthin Cycle in Higher Plants
JOURNAL	:	Pure Appl. Chem.
VOL	:	51 PAGE : 639- (1979)

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AUTHOR	:	Egeland,E.S., Eikrem,W., Throndsen,J., Wilhelm,C., Zapata,M., Liaaen-Jensen,S.
TITLE	:	Algal carotenoids 61: Carotenoids from Prasinophyceae 6: Carotenpids from Further Prasinophytes (Erratum 24: 179-180 (1996))
JOURNAL	:	Biochem. Syst. Ecol.
VOL	:	23 PAGE : 747-755 (1995)

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AUTHOR	:	Camara,B.
TITLE	:	Carotenogenic enzymes from Capsicum chromoplasts
JOURNAL	:	Pure Appl. Chem.
VOL	:	57 PAGE : 675-677 (1985)

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AUTHOR	:	Camara,B.
TITLE	:	Biosynthesis of keto-carotenoids in Capsicum annuum fruits
JOURNAL	:	FEBS Lett.
VOL	:	118 PAGE : 315-318 (1980)

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AUTHOR	:	Hiraoka,K.,Matsuno,T.,Ito,M.,Tsukida,M.,Schichida,Y., and Yoshizawa,T.
TITLE	:	Absolute Configuration of Pectenolone
JOURNAL	:	Bull. Jap. Soc. Sci. Fish.
VOL	:	48 PAGE : 215-217 (1982)

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[0517]

AUTHOR	:	Matsuno,T.,Maoka,T.,Sakaguchi,S., and Nishizawa,T.
TITLE	:	The Absolute Configuration of Pectenol
JOURNAL	:	Bull. Jap. Soc. Sci. Fish.
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TITLE	:	Dihydroxylycopene diglucoside diesters: a novel class of carotenoids from the phototrophic purple sulfur bacteria Halorhodospira abdelmalekii and Halorhodospira halochloris PubMed ID:11357508
JOURNAL	:	Arch Microbiol.
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AUTHOR	:	Takaichi, S., Inoue, K., Akaike, M., Kobayashi, M., Oh-oka, H., and Madigan, M. T.
TITLE	:	The major carotenoid in all known species of heliobacteria is the C30 carotenoid 4,4'-diaponeurosporene, not neurosporene PubMed ID:9297464
JOURNAL	:	Arch Microbiol.
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AUTHOR	:	Xiong, J., Inoue, K., and Bauer, C. E.
TITLE	:	Tracking molecular evolution of photosynthesis by characterization of a major photosynthesis gene cluster from Heliobacillus mobilis PubMed ID:9843979
JOURNAL	:	Proc Natl Acad Sci U S A.
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AUTHOR	:	Takaichi, S., Shimada, K., and Ishidsu, J.
TITLE	:	Monocyclic cross-conjugated carotenal from an aerobic photosynthetic bacterium, Erythrobacter longus
JOURNAL	:	Phytochemistry
VOL	:	27 PAGE : 3605-3609 (1988)

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AUTHOR	:	Takaichi, S., Furihata, K., Ishidsu, J., and Shimada, K.
TITLE	:	Carotenoid sulphates from the aerobic photosynthetic bacterium, Erythrobacter longus
JOURNAL	:	Phytochemistry
VOL	:	30 PAGE : 3411-3415 (1991)

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AUTHOR	:	Harashima, K., and Nakada, H.
TITLE	:	Carotenoids and ubiquinone in aerobically grown cells of an aerobic photosynthetic bacterium, Erythrobacter species OCh 114
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VOL	:	47 PAGE : 1057-1063 (1983)

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AUTHOR	:	Noguchi, T., Hayashi, H., Shimada, K., Takaichi, S., and Tasumi, M.
TITLE	:	In vivo states and functions of carotenoids in an aerobic photosynthetic bacterium, Erythrobacter longus
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AUTHOR	:	Takaichi, S., Furihata, K., and Harashima, K.
TITLE	:	Light-induced changes of carotenoid pigments in anaerobic cells of the aerobic photosynthetic bacterium, Roseobacter denitrificans (Erythrobacter species OCh 114): reduction of spheroidenone to 3,4-dihydrospheroidenone
JOURNAL	:	Arch. Microbiol.
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AUTHOR	:	Takaichi, S., and Shimada, K.
TITLE	:	Pigment composition of two pigment-protein complexes derived from anaerobically and semi-aerobically grown Rubrivivax gelatinosus, and identification of a new keto-carotenoid, 2-ketospirilloxanthin
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AUTHOR	:	Buchecker, R., Liaaen-Jensen, S., Borch, G.l., and Siegelman, H.W.
TITLE	:	Carotenoids of Anacystis nidulans, structures of caloxanthin and nostoxanthin
JOURNAL	:	Phytochemistry
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AUTHOR	:	Märki-Fischer, E., Bütikofer, P.-A., Buchecker, R., and Eugster, C.H.
TITLE	:	Absolute configuration of loroxanthin (=(3R,3'R,6'R)-b,e-carotene-3,19,3'-triol)
JOURNAL	:	Helv. Chim. Acta
VOL	:	66 PAGE : 1175-1182 (1983)

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AUTHOR	:	Sasa, T., Suda, S., Watanabe, M. M., and Takaichi, S.
TITLE	:	A yellow marine Chlamydomonas: Morphology and pigment composition
JOURNAL	:	Plant Cell Physiol.
VOL	:	33 PAGE : 527-534 (1992)

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AUTHOR	:	Sasa, T., Takaichi, S., Hatakeyama, N., and Watanabe, M.M.
TITLE	:	A novel carotenoid ester, loroxanthin dodecenoate, from Pyramimonas parkeae
JOURNAL	:	Plant Cell Physiol.
VOL	:	33 PAGE : 921-925 (1992)

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AUTHOR	:	Grung, M., Metzger, P., and Liaaen-Jensen, S.
TITLE	:	Primary and secondary carotenoids in two races of the green alga Botryococcus braunii
JOURNAL	:	Biochem. System. Ecol.
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AUTHOR	:	Bramley, P.M., and Sandmann, G.
TITLE	:	In vitro and in vivo biosynthesis of xanthophylls by the cyanobacteirum Aphanocapsa
JOURNAL	:	Phytochemistry
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AUTHOR	:	Holt, T.K., and Krogmann, D.W.
TITLE	:	A carotenoid-protein from cyanobacteria
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AUTHOR	:	Aguilar-Martinez, M. and Liaen-Jensen, S.
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AUTHOR	:	Coman, R. E., and Weedon, B.C.L.
TITLE	:	Carotenoids and related compounds: XXXIII. Synthesis of dehydroflexixanthin and deoxyflexixanthin
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AUTHOR	:	Andrewes, A.G., Foss, P., Borch, G. and Liaaen-Jensen, S.
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AUTHOR	:	Lang, H. P., Cogdell, R. J., Takaichi, S., and Hunter, C. N.
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AUTHOR	:	Schmidhauser, T. J., Lauter, F. R., Russo, V. E., and Yanofsky, C.
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AUTHOR	:	Wieland, B., Feil, C., Gloria-Maercker, E., Thumm, G., Lechner, M., Bravo, J. M., Poralla, K., and Gotz, F.
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AUTHOR	:	Krugel, H., Krubasik, P., Weber, K., Saluz, H. P., and Sandmann, G.
TITLE	:	Functional analysis of genes from Streptomyces griseus involved in the synthesis of isorenieratene, a carotenoid with aromatic end groups, revealed a novel type of carotenoid desaturase PubMed ID:10395965
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AUTHOR	:	Takaichi, S. and Ishidsu, J.
TITLE	:	Carotenoid glycoside ester from Rhodococcus rhodochrous
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AUTHOR	:	Maoka, T., Mochida, K., Kozuka, M., Ito, Y., Fujiwara, Y., Hashimoto, K., Enjo, F., Ogata, M., Nobukuni, Y., Tokuda, H., et al.
TITLE	:	Cancer chemopreventive activity of carotenoids in the fruits of red paprika Capsicum annuum L PubMed ID:11566483
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AUTHOR	:	Murakami, A., Nakashima, M., Koshiba, T., Maoka, T., Nishino, H., Yano, M., Sumida, T., Kim, O. K., Koshimizu, K., and Ohigashi, H.
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TITLE	:	Accumulation of unusual carotenoids in the spheroidene pathway, demethylspheoridene and demethylspheroidenone, in an alkaliphilic purple nonsulfur bacterium Rhodobaca bogoriensis
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AUTHOR	:	Takaichi, S., Wang, Z. Y., Umetsu, M., Nozawa, T., Shimada, K., and Madigan, M. T.
TITLE	:	New carotenoids from the thermophilic green sulfur bacterium Chlorobium tepidum: 1',2'-dihydro-gamma-carotene, 1',2'-dihydrochlorobactene, and OH-chlorobactene glucoside ester, and the carotenoid composition of different strains PubMed ID:9297463
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AUTHOR	:	Takaichi, S. and Oh-oka, H.
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AUTHOR	:	Takaichi, S., Tsuji, K., Matsuura, K., and Shimada, K.
TITLE	:	A monocyclic carotenoid glucoside ester is a major carotenoid in the green filamentous bacterium Chloroflexus aurantiacus
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AUTHOR	:	Hanada, S., Hiraishi, A., Shimada, K., and Matsuura, K.
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AUTHOR	:	Harada, J., Nagashima, K. V., Takaichi, S., Misawa, N., Matsuura, K., and Shimada, K.
TITLE	:	Phytoene desaturase, CrtI, of the purple photosynthetic bacterium, Rubrivivax gelatinosus, produces both neurosporene and lycopene PubMed ID:11673627
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AUTHOR	:	Takaichi, S., Ishidsu, J., Seki, T., and Fukuda, S.
TITLE	:	Carotenoid pigments from Rhodococcus rhodochrous RNMS1: two monocyclic carotenoids, a carotenoid monoglycoside and carotenoid glycoside monoesters
JOURNAL	:	Agric. Biol. Chem.
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AUTHOR	:	Takaichi, S. and Ishidsu, J.
TITLE	:	Influence of growth temperature on comositions of carotenoids and fatty acids from carotenoid glucoside ester and from cellular lipids in Rhodococcus rhodochrous RNMS1
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AUTHOR	:	Takaichi, S., Tamura, Y., Azegami, K., Yamamoto, Y., and Ishidsu, J.
TITLE	:	Carotenoid glucoside mycolic acid esters from the Nocardioform actinomycetes, Rhodococcus rhodochrous
JOURNAL	:	Phytochemistry
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AUTHOR	:	Takaichi, S., Tamura, Y., Miyamoto, Ta., Azegami, K., Yamamoto, Y., and Ishidsu, J.
TITLE	:	Carotenogenesis pathway of novel carotenoid glucoside mycolic acid esters in Rhodococcus rhodochrous using carotenogenesis mutants and inhibitors
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AUTHOR	:	Mimuro, M., Akimoto, S., Takaichi, S., and Yamazaki, I.
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AUTHOR	:	Katoh, T., Mimuro, M., and Takaichi, S.
TITLE	:	Light-harvesting particles isolated from a brown alga, Dictyota dichotoma. A supramolecular assembly of fucoxanthin-chlorophyll-protein compleses
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AUTHOR	:	Wang, C. W., and Liao, J. C.
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AUTHOR	:	von Lintig, J., and Vogt, K.
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AUTHOR	:	Krubasik, P., and Sandmann, G.
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TITLE	:	Chemopreventive efficacy of piroxicam administered alone or in combination with lycopene and beta-carotene on the development of rat urinary bladder carcinoma after N-butyl-N-(4-hydroxybutyl)nitrosamine treatment PubMed ID:9263531
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TITLE	:	Carotenoids of blue-green algae: 6. New carotenoid glycosides from Oscillatoria limosa
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JOURNAL	:	Phytochemistry
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TITLE	:	Carotenoids of blue-green algae: 11. The carbohydrate moieties bound to the carotenoids myxol and oscillol and their chemosystematic applications
JOURNAL	:	Phytochemistry
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AUTHOR	:	Aakermann, T., Skulberg, O.M., and Liaaen-Jensen, S.
TITLE	:	Carotenoids of blue-green algae: 12. A comparison of the carotenoids of strains of Oscillatoria and Spirulina (cyanobacteria)
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TITLE	:	Myxoxanthophyll in Synechocystis sp. PCC 6803 is myxol 2'-dimethyl-fucoside, (3R,2'S)-myxol 2'-(2,4-di-O-methyl-a-L-fucoside), not rhamnoside PubMed ID:11479383
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TITLE	:	Synthesis of (S)-plectaniaxanthin
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AUTHOR	:	Hertzberg, S. and Liaaen-Jensen, S.
TITLE	:	Bacterial carotenoids: 20. The carotenoids of Mycobacterium phlei strain vera: 2. The structure of the phlei-xanthophylls: two novel tertiary glucoside
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AUTHOR	:	Hertzberg, S., Liaaen-Jensen, S.
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AUTHOR	:	Hertzberg, S., and Liaaen-Jensen, S.
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AUTHOR	:	Egeland, E.S., Johnsen, G., Eikrem, W., Throndsen, J., Liaaen-Jensen, S.
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AUTHOR	:	Yoshii, Y., Takaichi, S., Maoka, T., Hanada, S., Inouye, I.
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AUTHOR	:	D'Auria, M.V., Riccio, R., Minale, L.
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AUTHOR	:	Strand, A., Herstad, O., Liaaen-Jensen, S.
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TITLE	:	¹H NMR, electronic-absorption and resonance-Raman spectra of isomeric okenone as compared with those of isomeric b-carotene, canthaxanthin, b-apo-8'-carotenal and spheroidene
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AUTHOR	:	Tsushima, M., Mune, E., Maoka, T., and Matsuno, T.
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AUTHOR	:	Takaichi, S., Maoka, T., Yamada, M., Matsuura, K., Haikawa, Y., Hanada, S.
TITLE	:	Absence of carotenes and presence of a tertiary methoxy group in a carotenoid from a thermophilic filamentous photosynthetic bacterium Roseiflexus castenholzii PubMed ID:11773528
JOURNAL	:	Plant Cell Physiol.
VOL	:	42 PAGE : 1355-1362 (2001)

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AUTHOR	:	Greenberg, E.P., Canale-Parola, E.
TITLE	:	Carotenoid pigments of facultatively anaerobic spirochetes PubMed ID:1158846
JOURNAL	:	J. Bacteriol.
VOL	:	123 PAGE : 1006-1012 (1975)

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AUTHOR	:	Britton, G., Singh, R.K., Goodwin, T.W., Ben-Aziz, A.
TITLE	:	The carotenoids of Rhodomicrobium vannielii (Rhodospirillaceae) and the effect of diphenylamine on the carotneoid composition
JOURNAL	:	Phytochemistry
VOL	:	14 PAGE : 2427-2433 (1975)

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AUTHOR	:	Kleinig, H., Reichenbach, H.
TITLE	:	A new carotenoid glucoside ester from Chondromyces apiculatus
JOURNAL	:	Phytochemistry
VOL	:	12 PAGE : 2483-2485 (1973)

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AUTHOR	:	Kleinig, H., Reichenbach, H., Achenbach, H., Stadler, J.
TITLE	:	Carotenoid pigments of Sorangium compositum (Myxobacteriales) including two new carotenoid glucoside esters and two new carotenoid rhamnosides PubMed ID:5099150
JOURNAL	:	Arch. Mikrobiol.
VOL	:	78 PAGE : 224-233 (1971)

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AUTHOR	:	Kleinig, H., Reichenbach, H.
TITLE	:	Carotenoid pigments of Stigmatella aurantiaca (Myxobacterales): I. the minor carotenoids PubMed ID:4315734
JOURNAL	:	Arch. Mikrobiol.
VOL	:	68 PAGE : 210-217 (1969)

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AUTHOR	:	Hosokawa, M., Kudo, M., Maeda, H., Kohno, H., Tanaka, T., Miyashita, K.
TITLE	:	Fucoxanthin induces apoptosis and enhances the antiproliferative effect of the PPAR&gamma& ligand, troglitazone, on colon cancer cells PubMed ID:15535974
JOURNAL	:	Biochim. Biophys. Acta
VOL	:	1675 PAGE : 113-119 (2004)

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AUTHOR	:	Maeda, H., Hosokawa, M., Sashima, t., Funayama, K., Miyashita, K.
TITLE	:	Fucoxanthin from edible seaweed, Undaria pinnatifida, shows antiobesity effect through UCP1 expression in white adipose tisues PubMed ID:15896707
JOURNAL	:	Biochem. Biophys. Res. Commun.
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AUTHOR	:	Taylor, R.F., Davies, B.H.
TITLE	:	Triterpenoid carotenoids and related lipids: Triterpenoid carotenid aldehydes from Streptococcus faecium UNH 564P PubMed ID:1275886
JOURNAL	:	Biochem. J.
VOL	:	153 PAGE : 233-239 (1976)

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AUTHOR	:	Davies, B.H., Taylor, R.F.
TITLE	:	The biosynthesis of triterpenoid carotenoids in Streptococcus faecium UNH 564P PubMed ID:7116207
JOURNAL	:	Can. J. Biochem.
VOL	:	60 PAGE : 684-692 (1982)

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AUTHOR	:	Taylor, R.F., Davies, B.H.
TITLE	:	The triterpenoid carotenoids and related terpenoids in Staphylococcus aureus 209P PubMed ID:6627101
JOURNAL	:	Can. J. Biochem. Cell Biol.
VOL	:	61 PAGE : 892-905 (1983)

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AUTHOR	:	Kleinig, H., Schmitt, R., Meister, W., Englert, G., Thommen, H.
TITLE	:	New-C₃₀-carotenid acid glucosyl esters from Pseudomonas rhodos
JOURNAL	:	Z. Naturforsch.
VOL	:	34 PAGE : 181-185 (1979)

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AUTHOR	:	Kleinig, H., Schmitt, R.
TITLE	:	On the biosynthesis of C₃₀ carotenoic acid glucosyl esters in Pseudomonas rhodos. Analysis of car-mutants
JOURNAL	:	Z. Naturforsch.
VOL	:	37 PAGE : 758-760 (1982)

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AUTHOR	:	Tao, L., Schenzle, A., Odom, J.M., Cheng, Q.
TITLE	:	Novel carotenoid oxidase involved in biosynthesis of 4,4'-diaolycopene dialdehyde PubMed ID:15933032
JOURNAL	:	Appl. Environ. Microbiol.
VOL	:	71 PAGE : 3294-3301 (2005)

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AUTHOR	:	Taylor, R.F., Davies, B.H.
TITLE	:	Triterpenoid carotenoids and related lipids: The triterpenoid carotenes of Streptococcus faecium UNH 564P PubMed ID:4212486
JOURNAL	:	Biochem. J.
VOL	:	139 PAGE : 751-760 (1974)

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AUTHOR	:	Taylor, R.F., Davies, B.H.
TITLE	:	A cell-free system from Streptococcus fecium for studies on the biosynthesis of triterpenoid carotenoids PubMed ID:6749265
JOURNAL	:	Can. J. Biochem.
VOL	:	60 PAGE : 675-683 (1982)

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AUTHOR	:	Taylor, R.F., Davies, B.H.
TITLE	:	Triterpenoid carotenoids and related lipids: Triterpenoid monohydroxy- and monoglucosyloxy-carotenoids from Streptococcus faecium UNH 564P PubMed ID:4212487
JOURNAL	:	Biochem. J.
VOL	:	139 PAGE : 761-769 (1974)

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