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DATA No : VCA0002 INFORMANT : Masayoshi Ito

NAME : (3S,3'S)-3,3'-Dihydroxy-b,b-carotene-4,4'-dione

COMMON NAME: Astaxanthin/ (3S,3'S)-Astaxanthin
FORMULA: C40H52O4 MOL.WT (average) : 596.838

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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).
MELTING POINT:216-218degC (Ref. 0010)





UV SPECTRA:lmax (nm) (e): CHCl3 sim225 (sim15000), 251 (14500), sim285sh (sim14000), 298 (15000), 324 (14500), 488 (125000) (Ref. 0010/0077/0080); methanol
[Spectrum 1102]

IR SPECTRA: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)

NMR SPECTRA: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)

MASS SPECTRA: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)

OTHER SPECTRA: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 (25degC): 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) 0.4times25 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) 0.32times50 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) 0.46times15 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 = 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 a_right idoxanthin a_right adonixanthin a_right zeaxanthin a_right zeaxanthin 5,6-epoxides (Ref. 0406/0407) Marine fish egg (Prognichthys aggo, Seriola quinqueradiata):astaxanthin a_right idoxanthin a_right b,b-carotene-3,4,3'-triol a_right zeaxanthin a_right 3-hydroxy-b,e-caroten-3'-one a_right e,e-carotene-3,3'-dione a_right 3-hydroxy-e,e-caroten-3'-dione a_right tunaxanthin (Ref. 0408) Yellowtail (Seriola quinqueradiata): astaxanthin a_right b-carotene-triol a_right zeaxanthin a_right 3'-epilutein a_right tunaxanthin (Ref. 0430/0435)
astaxanthin a_right a_right 3-dehydroretinal a_right retinal (Ref. 0216) Red sea bream (Pagrus major): astaxanthin a_right b-carotene-triol a_right zeaxanthin a_right 3'-epilutein a_right tunaxanthin (Ref. 0432) astaxanthin a_right idoxanthin a_right 4-ketozeaxanthin (Ref. 0436) Tilapia (Tilapia nilotica): astaxanthin a_right zeaxanthin a_right 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).
AUTHOR:Widmer,E., Zell,R., Lukác,T., Casadei,M.,S chönholzer,P., and Broger,E.A.
TITLE:Technische Verfahren zur Synthese von Carotinoiden und verwandten Verbindungen aus Oxo-isophoron. I. Modifizierung der Kienzle-Mayer-Synthese von (3S,3'S)-Astaxanthin
JOURNAL:Helv. Chim. Acta
VOL:64 PAGE : 2405 -2418 (1981)

AUTHOR:Widmer,E., Zell,R., Broger,E.A., Crameri,Y., Wagner,H.P., Dinkel,J., Schlageter,M., and Lukác,T.
TITLE:Technische Verfahren zur Synthese von Carotinoiden und verwandten Verbindungen aus 6-Oxo-isophoron. II. Ein neues Konzept für die Synthese von (3RS,3'RS)-Astaxanthin
JOURNAL:Helv. Chim. Acta
VOL:64 PAGE : 2436 -2446 (1981)

AUTHOR:Zell,R., Widmer,E., Lukác,T., Leuenberger,H.G.W., Schönholzer,P., and Broger,E.A.
TITLE:Technische Verfahren zur Synthese von Carotinoiden und verwandten Verbindungen aus 6-Oxo-isophoron. III. Ein neues Konzept für die Synthese der enantiomeren Astaxanthine
JOURNAL:Helv. Chim. Acta
VOL:64 PAGE : 2447 -2462 (1981)

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
VOL: PAGE : - ()

AUTHOR:Ernst,H. (1996) Carotenoids Volume 2: Synthesis Chapter 2: Coupling Reactions Part III: Wittig Olefination (Britton,G.,Liaaen-Jensen,S., and Pfander,H., eds), pp79-102, Birkhäuser Verlag,Basel,Boston,Berlin
VOL: PAGE : - ()

TITLE:Structure and Characterization of Carotenoids from Various Habitats and Natural Sources
JOURNAL:Methods Enzymol.
VOL:213 PAGE : 22 -31 (1992)

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

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)

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
VOL: PAGE : - ()

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)

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
VOL: PAGE : - ()

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)

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)

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 (pm)-3-Acetoxy-4-oxo-b-jonon
JOURNAL:Helv. Chim. Acta
VOL:64 PAGE : 2419 -2435 (1981)

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)

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

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)

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)

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)

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)

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

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)

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)

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)

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)

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)

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)

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

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

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
VOL:15 PAGE : 15-19 (1994)

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)

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)

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)

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)

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)

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)

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)

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)

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)

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)

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)

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)

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)

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)

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)

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)

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)

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)

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

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)

AUTHOR:Johnson, E.A., and An, G .-H.
TITLE:Astaxanthin from microbial sources
JOURNAL:Crit. Rev. Biotechnol.
VOL:11 PAGE : 297 -326 (1991)

AUTHOR:Misawa, N., Kajiwara, S., Kondo, K., Yokoyama, A., Satomi, Y., Saito, T., Miki, W., and Ohtani, T.
TITLE:Canthaxanthin biosynthesis by the conversion of methylene to keto groups in a hydrocarbon beta-carotene by a single gene PubMed ID:7733978
JOURNAL:Biochem Biophys Res Commun.
VOL:209 PAGE : 867-876 (1995)

AUTHOR:Fraser, P. D., Shimada, H., and Misawa, N.
TITLE:Enzymic confirmation of reactions involved in routes to astaxanthin formation, elucidated using a direct substrate in vitro assay PubMed ID:9523693
JOURNAL:Eur J Biochem.
VOL:252 PAGE : 229-236 (1998)

AUTHOR:Linden, H.
TITLE:Carotenoid hydroxylase from Haematococcus pluvialis: cDNA sequence, regulation and functional complementation PubMed ID:10524195
JOURNAL:Biochim Biophys Acta.
VOL:1446 PAGE : 203-212 (1999)

AUTHOR:Lotan, T., and Hirschberg, J.
TITLE:Cloning and expression in Escherichia coli of the gene encoding beta-C-4-oxygenase, that converts beta-carotene to the ketocarotenoid canthaxanthin in Haematococcus pluvialis PubMed ID:7750556
VOL:364 PAGE : 125-128 (1995)

AUTHOR:Harker, M., Hirschberg, J., and Oren, A.
TITLE:Paracoccus marcusii sp. nov., an orange gram-negative coccus PubMed ID:9731296
JOURNAL:Int J Syst Bacteriol.
VOL:48 Pt 2 PAGE : 543-548 (1998)

AUTHOR:Kobayashi, M.
TITLE:In vivo antioxidant role of astaxanthin under oxidative stress in the green alga Haematococcus pluvialis PubMed ID:11092631
JOURNAL:Appl Microbiol Biotechnol.
VOL:54 PAGE : 550-555 (2000)

AUTHOR:Margalith, P. Z.
TITLE:Production of ketocarotenoids by microalgae PubMed ID:10341427
JOURNAL:Appl Microbiol Biotechnol.
VOL:51 PAGE : 431-438 (1999)

AUTHOR:Hanagata, N. and Dubinsky, Z.
TITLE:Secondary carotenoid accumulation in Scenedesmus komarekii (Chlorophyceae, Chlorophyta)
JOURNAL:J. Phycol.
VOL:35 PAGE : 960 -966 (1999)

AUTHOR:Turujman, S.A.
TITLE:Rapid direct resolution of the stereoisomers of all-trans astaxanthin on a Pirkle covalent L-leucine column
JOURNAL:J. Chromatogr.
VOL:631 PAGE : 197 -199 (1993)

AUTHOR:Nishino, H., Tokuda , H., Satomi, Y., Masuda, M., Bu, P., Onozuka, M., Yamaguchi, S., Okuda, Y., Takayasu, J., Tsurata, J., Okada, M., Ichiishi, E., Murakoshi, M., Kato, T., Misawa, N., Narisawa, T., Takasuka, N., and Yano, M.
TITLE:Cancer prevention by carotenoids
JOURNAL:Pure Appl. Chem.
VOL:71 PAGE : 2273 -2278 (1999)

AUTHOR:Takaichi, S., Matsui, K., Nakamura, M., Muramatsu, M., and Hanada, S.
TITLE:Fatty acids of astaxanthin esters in krill determined by mild mass spectrometry PubMed ID:14529757
JOURNAL:Comp Biochem Physiol B Biochem Mol Biol.
VOL:136 PAGE : 317-322 (2003)

AUTHOR:Foss, P., Renstrøn, B., Liaaen-Jensen, S.
TITLE:Natural occurrence of enantiomeric and meso astasanthin: 7. Crustaceans including zooplankton
JOURNAL:Comp. Biochem. Physiol. B
VOL:86 PAGE : 313 -314 (1987)

AUTHOR:Quarmby, R., Norden, D.A., Zagalsky, P.F., Ceccaldi, H.J., Daumas, R.
TITLE:Studies on the quaternary structure of the lobster exoskeleton carotenoprotein, crustacyanin
JOURNAL:Comp. Biochem. Physiol.
VOL:56 PAGE : 55 -61 (1977)

AUTHOR:Cianci, M., Rizkallah, P. J., Olczak, A., Raftery, J., Chayen, N. E., Zagalsky, P. F., and Helliwell, J. R.
TITLE:The molecular basis of the coloration mechanism in lobster shell: beta-crustacyanin at 3.2-A resolution PubMed ID:12119396
JOURNAL:Proc Natl Acad Sci U S A.
VOL:99 PAGE : 9795-9800 (2002)

AUTHOR:Chayen, N.E., Cianci, M., Grossmann, J.G., Habash, J., Helliwell, J.R., Nneji, G.A., Raftery, J., Rizkallah, P.J., Zagalsky, P.F.
TITLE:Unravelling the structural chemistry of the colouration mechanism in lobster shell
JOURNAL:Acta Cryst.
VOL:59 PAGE : 2072 -2082 (2003)

AUTHOR:Britton, G., Weesie, R.J., Askin, D., Warburton, J.D., Gallardo-Guerrero, L., Jansen, F.J., de Groot, H.J.M., Lugtenburg, J., Cornard, J.-P., Merlin, J.-C.
TITLE:Carotenoid blues: structural studies on carotenoproteins
JOURNAL:Pure Appl. Chem.
VOL:69 PAGE : 2075 -2084 (1997)

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)

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