Back to HOME

Carotenoid


DATA No : VCA0001 INFORMANT : Masayoshi Ito

NAME : b,b-Carotene

COMMON NAME: b-Carotene/ b,b-Carotene
SYMBOL: BC
FORMULA: C40H56 MOL.WT (average) : 536.873


Download ChemDraw structure data
BIOLOGICAL ACTIVITY
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).
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:180-182degC (Ref. 0023)
177-180degC (Ref. 0024)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA: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]

IR SPECTRA:nmax(KBr)/cm-1: 1629 and 1599w (C=C) and 965s (CH)
[Spectrum 0002] (Ref. 0065)

NMR SPECTRA: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).

MASS SPECTRA: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)

OTHER SPECTRA:
CHROMATOGRAM DATA
RF-TLC on 0.25 mm RP-18 layers (Merck, Art. 15423) using several ratio of light petroleum (bp 40-60degC)-acetonitrile-methanol ex: 1:6:3 Rf=0.09, 3:1:6 Rf=0.20 (Ref. 0135)
HPLC (column: calcium hydroxide (Nakarai) 0.4times30 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) 0.28times25 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) 0.46times15 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)
SOURCE
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)
CHEMICAL SYNTHESIS
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)
METABOLISM
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).
GENETIC INFORMATION
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.
NOTE
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)
REFERENCES
[0014]
AUTHOR:Mayer,H. and Hengartner,U. (1996) Carotenoids Volume 2: Synthesis Chapter 1: General Aspects Part III: Characterization of Products (Britton,G.,Liaaen-Jensen,S., and Pfander,H., eds), pp15-26, Birkhäuser Verlag,Basel,Boston,Berlin
TITLE:
JOURNAL:
VOL: PAGE : - ()
[TOP]

[0015]
AUTHOR:Manchand,P.S. (1996) Carotenoids Volume 2: Synthesis Chapter 2: Coupling Reactions Part II: Organometallic Reactions (Britton,G.,Liaaen-Jensen,S., and Pfander,H., eds), pp55-78, Birkhäuser Verlag,Basel,Boston,Berlin
TITLE:
JOURNAL:
VOL: PAGE : - ()
[TOP]

[0017]
AUTHOR:Otera,J. (1996) Carotenoids Volume 2: Synthesis Chapter 2: Coupling Reactions Part IV: Sulphone Coupling (Britton,G.,Liaaen-Jensen,S., and Pfander,H., eds), pp103-114, Birkhäuser Verlag,Basel,Boston,Berlin
TITLE:
JOURNAL:
VOL: PAGE : - ()
[TOP]

[0020]
AUTHOR:Paust,J. (1996) Carotenoids Volume 2: Synthesis Chapter 3: Carotenoid Synthesis Part VII: Technical Synthesis (Britton,G.,Liaaen-Jensen,S., and Pfander,H., eds), pp259-274, Birkhäuser Verlag,Basel,Boston,Berlin
TITLE:
JOURNAL:
VOL: PAGE : - ()
[TOP]

[0021]
AUTHOR:Surmatis,J.D., and Thommen,R.
TITLE:The Synthesis of trans-b-Carotene from Retinyl Phosphonate by the Michaelis-Arbuzov Reaction
JOURNAL:J. Org. Chem.
VOL:34 PAGE : 559 -560 (1969)
[TOP]

[0022]
AUTHOR:Isler,O.,Lindlar,H.,Montavon,M., and Zeller,P.
TITLE:Synthesen in der Carotenoid-Reihe. Die techniche Synthese von b-Carotin
JOURNAL:Helv. Chim. Acta
VOL:39 PAGE : 249 -259 (1956)
[TOP]

[0023]
AUTHOR:Mc Murry, J. E., and Fleming, M. P.
TITLE:A new method for the reductive coupling of carbonyls to olefins. Synthesis of beta-carotene PubMed ID:4850242
JOURNAL:J Am Chem Soc.
VOL:96 PAGE : 4708-4709 (1974)
[TOP]

[0024]
AUTHOR:Ishida,A. and Mukaiyama,T.
TITLE:A convenient method for the preparation of symmetrical polyolefins; synthesis of b-carotene
JOURNAL:Chem. Lett.
VOL: PAGE : 1127 -1130 (1976)
[TOP]

[0025]
AUTHOR:Okukado,N.,Uchikawa,O., and Nakamura,Y.
TITLE:Palladium-Catalyzed Allylidenation of Aldehyde. A Simple and Convenient Method for the Preparation of Conjugated Diene and Polyene Compounds
JOURNAL:Chem. Lett.
VOL: PAGE : 1449 -1452 (1988)
[TOP]

[0026]
AUTHOR:Bernhard,K. and Mayer,H.
TITLE:Recent advances in the synthesis of achiral carotenoids
JOURNAL:Pure Appl. Chem.
VOL:63 PAGE : 35 -44 (1991)
[TOP]

[0058]
AUTHOR:Bjfrnland,T. and Aguilar-Martinez,M.
TITLE:Carotenoids in red algae
JOURNAL:Phytochemistry
VOL:15 PAGE : 291 -296 (1976)
[TOP]

[0060]
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)
[TOP]

[0061]
AUTHOR:Moss,G.P.
TITLE:Carbon-13 NMR spectra of carotenoids
JOURNAL:Pure Appl. Chem.
VOL:2047 PAGE : 97 -102 (1976)
[TOP]

[0062]
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)
[TOP]

[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 : - ()
[TOP]

[0065]
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:
VOL: PAGE : - ()
[TOP]

[0066]
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)
[TOP]

[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)
[TOP]

[0088]
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)
[TOP]

[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)
[TOP]

[0091]
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)
[TOP]

[0092]
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)
[TOP]

[0093]
AUTHOR:Terao, J.
TITLE:Antioxidant activity of beta-carotene-related carotenoids in solution PubMed ID:2779372
JOURNAL:Lipids.
VOL:24 PAGE : 659-661 (1989)
[TOP]

[0099]
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)
[TOP]

[0100]
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)
[TOP]

[0101]
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)
[TOP]

[0102]
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)
[TOP]

[0103]
AUTHOR:Burton, G. W.
TITLE:Antioxidant action of carotenoids PubMed ID:2643692
JOURNAL:J Nutr.
VOL:119 PAGE : 109-111 (1989)
[TOP]

[0135]
AUTHOR:Isaksen,M., and Francis,G.W.
TITLE:Reversed-phase thin-layer chromatography of carotenoids
JOURNAL:J. Chromatogr.
VOL:355 PAGE : 358 -362 (1986)
[TOP]

[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)
[TOP]

[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)
[TOP]

[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)
[TOP]

[0214]
AUTHOR:Mathews-Roth,M.M.
TITLE:Recent Progress in the Medical Applications of Carotenoid
JOURNAL:Pure Appl. Chem.
VOL:63 PAGE : 147 -156 (1991)
[TOP]

[0216]
AUTHOR:Matsuno,T.
TITLE:Xanthophylls as Precursors of Retinoids
JOURNAL:Pure Appl. Chem.
VOL:63 PAGE : 81 -88 (1991)
[TOP]

[0217]
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)
[TOP]

[0226]
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)
[TOP]

[0227]
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)
[TOP]

[0228]
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)
[TOP]

[0229]
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)
[TOP]

[0230]
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)
[TOP]

[0232]
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)
[TOP]

[0233]
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)
[TOP]

[0234]
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)
[TOP]

[0409]
AUTHOR:Goodwin T. W. (1980) The biochemistry of the carotenoids, Volume I, Plants, Chapman and Hall, London and New York
TITLE:
JOURNAL:
VOL: PAGE : - ()
[TOP]

[0410]
AUTHOR:Goodwin T. W. (1984) The biochemistry of the carotenoids, Volume II, Animals, Chapman and Hall, London and New York
TITLE:
JOURNAL:
VOL: PAGE : - ()
[TOP]

[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)
[TOP]

[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)
[TOP]

[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)
[TOP]

[1001]
AUTHOR:Sandmann, G., and Misawa, N.
TITLE:New functional assignment of the carotenogenic genes crtB and crtE with constructs of these genes from Erwinia speicies
JOURNAL:FEMS Microbiol. Lett.
VOL:90 PAGE : 253 -258 (1992)
[TOP]

[1002]
AUTHOR:Misawa, N., and Shimada, H.
TITLE:Metabolic engineering for the production of carotenoids in non-carotenogenic bacteria and yeasts PubMed ID:9519479
JOURNAL:J Biotechnol.
VOL:59 PAGE : 169-181 (1997)
[TOP]

[1003]
AUTHOR:Misawa, N., Masamoto, K., Hori, T., Ohtani, T., Böger, P., and Sandmann, G.
TITLE:Expression of an Erwinia phytoene desaturase gene not only confers multiple resistance to herbicides interfering with carotenoid biosynthesis but also alters xanthophyll metabolism in transgenic plants
JOURNAL:Plant J.
VOL:6 PAGE : 481 -489 (1994)
[TOP]

[1004]
AUTHOR:Sandmann, G.
TITLE:Carotenoid biosynthesis in microorganisms and plants PubMed ID:8033911
JOURNAL:Eur J Biochem.
VOL:223 PAGE : 7-24 (1994)
[TOP]

[1005]
AUTHOR:Armstrong, G. A., and Hearst, J. E.
TITLE:Carotenoids 2: Genetics and molecular biology of carotenoid pigment biosynthesis PubMed ID:8641556
JOURNAL:Faseb J.
VOL:10 PAGE : 228-237 (1996)
[TOP]

[1006]
AUTHOR:The Alpha-Tocopherol, Beta Carotene Cancer Prevention Study Group
TITLE:The effect of vitamin E and beta carotene on the incidence of lung cancer and other cancer in male smokers
JOURNAL:New England J. Medicine
VOL:330 PAGE : 1029 -1035 (1994)
[TOP]

[1017]
AUTHOR:Ye, X., Al-Babili, S., Kloti, A., Zhang, J., Lucca, P., Beyer, P., and Potrykus, I.
TITLE:Engineering the provitamin A (beta-carotene) biosynthetic pathway into (carotenoid-free) rice endosperm PubMed ID:10634784
JOURNAL:Science.
VOL:287 PAGE : 303-305 (2000)
[TOP]

[1018]
AUTHOR:Schnurr, G., Misawa, N., and Sandmann, G.
TITLE:Expression, purification and properties of lycopene cyclase from Erwinia uredovora PubMed ID:8645170
JOURNAL:Biochem J.
VOL:315 (Pt 3) PAGE : 869-874 (1996)
[TOP]

[1044]
AUTHOR:Wyss, A., Wirtz, G., Woggon, W., Brugger, R., Wyss, M., Friedlein, A., Bachmann, H., and Hunziker, W.
TITLE:Cloning and expression of beta,beta-carotene 15,15'-dioxygenase PubMed ID:10799297
JOURNAL:Biochem Biophys Res Commun.
VOL:271 PAGE : 334-336 (2000)
[TOP]

[1052]
AUTHOR:Takaichi, S. and Shimada, K.
TITLE:Characterization of carotenoids in photosynthetic bacteria
JOURNAL:Methods Enzymol.
VOL:213 PAGE : 374 -385 (1992)
[TOP]

[1053]
AUTHOR:Takaichi, S.
TITLE:Usefulness of field desorption mass spectrometry in determining molecular masses of carotenoids, natural carotenoid derivatives and their chemical derivatives
JOURNAL:Org. Mass Spectrom.
VOL:28 PAGE : 785 -788 (1993)
[TOP]

[1057]
AUTHOR:Takaichi, S.
TITLE:Characterization of carotenes in a combination of a C18 HPLC column with isocratic elution and absorption spectra with a photodiode-array detector
JOURNAL:Photosynth. Res.
VOL:65 PAGE : 93 -99 (2000)
[TOP]

[1066]
AUTHOR:Romer, S., Fraser, P. D., Kiano, J. W., Shipton, C. A., Misawa, N., Schuch, W., and Bramley, P. M.
TITLE:Elevation of the provitamin A content of transgenic tomato plants PubMed ID:10835607
JOURNAL:Nat Biotechnol.
VOL:18 PAGE : 666-669 (2000)
[TOP]

[1077]
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
VOL:15 PAGE : 1015 -1018 (1976)
[TOP]

[1099]
AUTHOR:Zhang, H., Huang, D., and Cramer, W. A.
TITLE:Stoichiometrically bound beta-carotene in the cytochrome b6f complex of oxygenic photosynthesis protects against oxygen damage PubMed ID:9880536
JOURNAL:J Biol Chem.
VOL:274 PAGE : 1581-1587 (1999)
[TOP]

[1105]
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
JOURNAL:Plant Cell Physiol.
VOL:36 PAGE : 773 -778 (1995)
[TOP]

[1106]
AUTHOR:Hanada, S., Hiraishi, A., Shimada, K., and Matsuura, K.
TITLE:Chloroflexus aggregans sp. nov., a filamentous phototrophic bacterium which forms dense cell aggregates by active gliding movement PubMed ID:7547286
JOURNAL:Int J Syst Bacteriol.
VOL:45 PAGE : 676-681 (1995)
[TOP]

[1115]
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
JOURNAL:Biochim. Biophys. Acta
VOL:976 PAGE : 233 -240 (1989)
[TOP]

[1122]
AUTHOR:von Lintig, J., and Vogt, K.
TITLE:Filling the gap in vitamin A research. Molecular identification of an enzyme cleaving beta-carotene to retinal PubMed ID:10766819
JOURNAL:J Biol Chem.
VOL:275 PAGE : 11915-11920 (2000)
[TOP]

[1123]
AUTHOR:Redmond, T. M., Gentleman, S., Duncan, T., Yu, S., Wiggert, B., Gantt, E., and Cunningham, F. X., Jr.
TITLE:Identification, expression, and substrate specificity of a mammalian beta-carotene 15,15'-dioxygenase PubMed ID:11092891
JOURNAL:J Biol Chem.
VOL:276 PAGE : 6560-6565 (2001)
[TOP]

[1124]
AUTHOR:Krubasik, P., and Sandmann, G.
TITLE:A carotenogenic gene cluster from Brevibacterium linens with novel lycopene cyclase genes involved in the synthesis of aromatic carotenoids PubMed ID:10821176
JOURNAL:Mol Gen Genet.
VOL:263 PAGE : 423-432 (2000)
[TOP]

[1127]
AUTHOR:Viveiros, M., Krubasik, P., Sandmann, G., and Houssaini-Iraqui, M.
TITLE:Structural and functional analysis of the gene cluster encoding carotenoid biosynthesis in Mycobacterium aurum A+ PubMed ID:10828407
JOURNAL:FEMS Microbiol Lett.
VOL:187 PAGE : 95-101 (2000)
[TOP]

[1137]
AUTHOR:Mimuro, M., Tomo, T., Nishimura, Y., Yamazaki, I. and Satoh, K.
TITLE:Identification of a photochemically inactive pheophytin molecule in the spinach D1-D2-cytb559 complex
JOURNAL:Biochim. Biophys. Acta
VOL:1232 PAGE : 81 -88 (1995)
[TOP]

[1160]
AUTHOR:Rao, M. N., Ghosh, P., and Lakshman, M. R.
TITLE:Purification and partial characterization of a cellular carotenoid-binding protein from ferret liver PubMed ID:9305906
JOURNAL:J Biol Chem.
VOL:272 PAGE : 24455-24460 (1997)
[TOP]

[1172]
AUTHOR:Verdoes, J. C., Krubasik, K. P., Sandmann, G., and van Ooyen, A. J.
TITLE:Isolation and functional characterisation of a novel type of carotenoid biosynthetic gene from Xanthophyllomyces dendrorhous PubMed ID:10589832
JOURNAL:Mol Gen Genet.
VOL:262 PAGE : 453-461 (1999)
[TOP]

[1173]
AUTHOR:Velayos, A., Eslava, A. P., and Iturriaga, E. A.
TITLE:A bifunctional enzyme with lycopene cyclase and phytoene synthase activities is encoded by the carRP gene of Mucor circinelloides PubMed ID:10951210
JOURNAL:Eur J Biochem.
VOL:267 PAGE : 5509-5519 (2000)
[TOP]

[1174]
AUTHOR:Arrach, N., Fernandez-Martin, R., Cerda-Olmedo, E., and Avalos, J.
TITLE:A single gene for lycopene cyclase, phytoene synthase, and regulation of carotene biosynthesis in Phycomyces PubMed ID:11172012
JOURNAL:Proc Natl Acad Sci U S A.
VOL:98 PAGE : 1687-1692 (2001)
[TOP]

[1176]
AUTHOR:Arrach, N., Schmidhauser, T. J., and Avalos, J.
TITLE:Mutants of the carotene cyclase domain of al-2 from Neurospora crassa PubMed ID:11862485
JOURNAL:Mol Genet Genomics.
VOL:266 PAGE : 914-921 (2002)
[TOP]

[1185]
AUTHOR:Kiefer, C., Hessel, S., Lampert, J. M., Vogt, K., Lederer, M. O., Breithaupt, D. E., and von Lintig, J.
TITLE:Identification and characterization of a mammalian enzyme catalyzing the asymmetric oxidative cleavage of provitamin A PubMed ID:11278918
JOURNAL:J Biol Chem.
VOL:276 PAGE : 14110-14116 (2001)
[TOP]

[1211]
AUTHOR:Okajima, E., Ozono, S., Endo, T., Majima, T., Tsutsumi, M., Fukuda, T., Akai, H., Denda, A., Hirao, Y., Okajima, E., et al.
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
JOURNAL:Jpn J Cancer Res.
VOL:88 PAGE : 543-552 (1997)
[TOP]

[1212]
AUTHOR:Majima, T., Tsutsumi, M., Nishino, H., Tsunoda, T., and Konishi, Y.
TITLE:Inhibitory effects of beta-carotene, palm carotene, and green tea polyphenols on pancreatic carcinogenesis initiated by N-nitorsobis(2-oxopropyl)amine in Syrian golden hamsters PubMed ID:9436857
JOURNAL:Pancreas.
VOL:16 PAGE : 13-18 (1998)
[TOP]

[1231]
AUTHOR:Yan, W., Jang, G. F., Haeseleer, F., Esumi, N., Chang, J., Kerrigan, M., Campochiaro, M., Campochiaro, P., Palczewski, K., and Zack, D. J.
TITLE:Cloning and characterization of a human beta,beta-carotene-15,15'-dioxygenase that is highly expressed in the retinal pigment epithelium PubMed ID:11401432
JOURNAL:Genomics.
VOL:72 PAGE : 193-202 (2001)
[TOP]

[1233]
AUTHOR:Paik, J., During, A., Harrison, E. H., Mendelsohn, C. L., Lai, K., and Blaner, W. S.
TITLE:Expression and characterization of a murine enzyme able to cleave beta-carotene. The formation of retinoids PubMed ID:11418584
JOURNAL:J Biol Chem.
VOL:276 PAGE : 32160-32168 (2001)
[TOP]

[1258]
AUTHOR:Krubasik, P., and Sandmann, G.
TITLE:Molecular evolution of lycopene cyclases involved in the formation of carotenoids with ionone end groups PubMed ID:11171215
JOURNAL:Biochem Soc Trans.
VOL:28 PAGE : 806-810 (2000)
[TOP]

[1266]
AUTHOR:Jüttner, F., Höflacher, B.
TITLE:Evidence of b-carotene 7,8(7',8') oxygenase (b-cyclocitral, crocetindial generating) in Microcystis
JOURNAL:Arch. Microbiol.
VOL:141 PAGE : 337 -343 (1985)
[TOP]

[1272]
AUTHOR:Bryant, J.D., McCord, J.D., Unlu, L. K., Erdman, Jr., J.W.
TITLE:Isolation and partial characterization of a- and b-carotene-containing carotenoprotein from carrot (Daucus carota L.) root chromoplasts
JOURNAL:J. Agric. Food Chem.
VOL:40 PAGE : 545 -549 (1992)
[TOP]

[1288]
AUTHOR:Jordan, P., Fromme, P., Witt, H. T., Klukas, O., Saenger, W., and Krauss, N.
TITLE:Three-dimensional structure of cyanobacterial photosystem I at 2.5 A resolution PubMed ID:11418848
JOURNAL:Nature.
VOL:411 PAGE : 909-917 (2001)
[TOP]

[1289]
AUTHOR:Kamiya, N., and Shen, J. R.
TITLE:Crystal structure of oxygen-evolving photosystem II from Thermosynechococcus vulcanus at 3.7-A resolution PubMed ID:12518057
JOURNAL:Proc Natl Acad Sci U S A.
VOL:100 PAGE : 98-103 (2003)
[TOP]

[1290]
AUTHOR:Ferreira, K. N., Iverson, T. M., Maghlaoui, K., Barber, J., and Iwata, S.
TITLE:Architecture of the photosynthetic oxygen-evolving center PubMed ID:14764885
JOURNAL:Science.
VOL:303 PAGE : 1831-1838 (2004)
[TOP]

[1292]
AUTHOR:Stroebel, D., Choquet, Y., Popot, J. L., and Picot, D.
TITLE:An atypical haem in the cytochrome b(6)f complex PubMed ID:14647374
JOURNAL:Nature.
VOL:426 PAGE : 413-418 (2003)
[TOP]

[1294]
AUTHOR:Kurisu, G., Zhang, H., Smith, J. L., and Cramer, W. A.
TITLE:Structure of the cytochrome b6f complex of oxygenic photosynthesis: tuning the cavity PubMed ID:14526088
JOURNAL:Science.
VOL:302 PAGE : 1009-1014 (2003)
[TOP]

[1310]
AUTHOR:Peck, R. F., Johnson, E. A., and Krebs, M. P.
TITLE:Identification of a lycopene beta-cyclase required for bacteriorhodopsin biogenesis in the archaeon Halobacterium salinarum PubMed ID:12003928
JOURNAL:J Bacteriol.
VOL:184 PAGE : 2889-2897 (2002)
[TOP]

[1311]
AUTHOR:Hemmi, H., Ikejiri, S., Nakayama, T., Nishino, T.
TITLE:Fusion-type lycopene b-cyclase from a thermoacidophilic archaeon Sulfolobus solfataricus PubMed ID:12763034
JOURNAL:Biochem. Biophys. Res. Com.
VOL:305 PAGE : 586 -591 (2003)
[TOP]

[1312]
AUTHOR:Rodriguez-Saiz, M., Paz, B., De La Fuente, J. L., Lopez-Nieto, M. J., Cabri, W., and Barredo, J. L.
TITLE:Blakeslea trispora genes for carotene biosynthesis PubMed ID:15345447
JOURNAL:Appl Environ Microbiol.
VOL:70 PAGE : 5589-5594 (2004)
[TOP]

[1313]
AUTHOR:Hornero-Mendez, D., and Britton, G.
TITLE:Involvement of NADPH in the cyclization reaction of carotenoid biosynthesis PubMed ID:11943208
JOURNAL:FEBS Lett.
VOL:515 PAGE : 133-136 (2002)
[TOP]

[1336]
AUTHOR:Kern, J., Loll, B., Lüneberg, C., DiFiore, D., Biesiadka, J., Irrgang, K.-D., Zouni, A.
TITLE:Purification, characterisation and crystallisation of photosystem II from Thermosynechococcus elongatus cultivated in a new type of photobioreactor PubMed ID:15620375
JOURNAL:Biochim. Biophys. Acta
VOL:1706 PAGE : 147 -157 (2005)
[TOP]

[1337]
AUTHOR:Hashimoto, H., Yoda, T., Kobayashi, T., Young, A.J.
TITLE:Molecular structures of carotenoids as predicted by MNDO-AM1 molecular orbital calculations
JOURNAL:J. Mol. Struct.
VOL:604 PAGE : 125 -146 (2002)
[TOP]

Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.