astaxanthin from lipid bank

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Carotenoid DATA No : VCA0002 INFORMANT : Masayoshi Ito NAME : (3S,3'S)-3,3'-Dihydroxy-,-carotene-4,4'-dione COMMON NAME : Astaxanthin/ (3S,3'S)- Astaxanthin SYMBOL : FORMULA : C 40 H 52 O 4 MOL.WT (average) : 596.838 Download ChemDraw structure data BIOLOGICAL ACTIVITY 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 ). -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 ). -Crustacyanin is a heterodimer of one CRTA and one CRTC, and two molecules of astaxanthin are located between two peptides. -Crustacyanin is octamer of -

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Page 1: astaxanthin from lipid bank

Carotenoid

DATA No : VCA0002 INFORMANT : Masayoshi Ito

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

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

Download ChemDraw structure data

BIOLOGICAL ACTIVITY

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).

-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). -Crustacyanin is a heterodimer of one CRTA and one CRTC, and two molecules of astaxanthin are located between two peptides. -Crustacyanin is octamer of -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 -crustacyanin is ca. 580 nm, and that of -crustacyanin is ca. 630 nm. Keto group is essential to bind peptide and spectral shift (Ref. 1275/1276). 3D-Structure of -crustacyanin (A1 and A2 dimer) is investigated (Ref. 1274).

PHYSICAL AND CHEMICAL PROPERTIES

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MELTING POINT

: 216-218 C (Ref. 0010)

BOILING POINT :

REFRACTIVE INDEX

:

OPTICAL ROTATION

:

DENSITY :

SOLUBILITY :

SPECTRAL DATA

UV SPECTRA :

max (nm) (): CHCl3 225 ( 15000), 251 (14500), 285sh (14000), 298 (15000), 324 (14500), 488 (125000) (Ref. 0010/0077/0080); methanol [Spectrum 1102]

IR SPECTRA :

max(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 (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)

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OTHER SPECTRA

:

CD data in CH2Cl2 solution: 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 (25 C): 240 (-20.0), 252 (0), 270 (+20.0), 284 (0), 314 (-34.0), 355 (0), 372 (+3.0) (Ref. 0421)

CHROMATOGRAM DATATLC (Kieselgel 60 Merck, CH2Cl2-acetone-formic acid 95:5:3) Rf = 0.3 (Ref. 0010) HPLC (column: Sumipax OA-2000 (10m) 0.4 25 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 m) 0.32 50 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) 0.46 15 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) -carotene, echinenone, -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).

SOURCE

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, -3 subclass of the Proteobacteria) (Ref. 1012)

CHEMICAL SYNTHESIS

Page 4: astaxanthin from lipid bank

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--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)

METABOLISM

Rainbow trout and salmon: astaxanthin idoxanthin adonixanthin zeaxanthin zeaxanthin 5,6-epoxides (Ref. 0406/0407) Marine fish egg (Prognichthys aggo, Seriola quinqueradiata):astaxanthin idoxanthin ,-carotene-3,4,3'-triol zeaxanthin 3-hydroxy-,-caroten-3'-one ,-carotene-3,3'-dione 3-hydroxy-,-caroten-3'-dione tunaxanthin (Ref. 0408) Yellowtail (Seriola quinqueradiata): astaxanthin -carotene-triol zeaxanthin 3'-epilutein tunaxanthin (Ref. 0430/0435) astaxanthin 3-dehydroretinal retinal (Ref. 0216) Red sea bream (Pagrus major): astaxanthin -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).

GENETIC INFORMATION

Genes required for the biosynthesis of astaxanthin from -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). -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).

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NOTE

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).

REFERENCES

[0010]

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)

[TOP]

[0011]

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)

[TOP]

[0012]

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)

[TOP]

[0015]

AUTHOR : Manchand,P.S. (1996) Carotenoids Volume 2: Synthesis Chapter 2:

Page 6: astaxanthin from lipid bank

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]

[0016]

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

TITLE :JOURNAL :VOL : PAGE : - ()

[TOP]

[0032]

AUTHOR : Matsuno,T.

TITLE :Structure and Characterization of Carotenoids from Various Habitats and Natural Sources

JOURNAL : Methods Enzymol. VOL : 213 PAGE : 22 -31 (1992)

[TOP]

[0058]

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

[TOP]

[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)

[TOP]

Page 7: astaxanthin from lipid bank

[0064]

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 :VOL : PAGE : - ()

[TOP]

[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)

[TOP]

[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 :VOL : PAGE : - ()

[TOP]

[0070]

AUTHOR : Maoka,T.,Komori,T., and Matsuno,T.

TITLE :Direct diastereomeric resolution of carotenoids I. 3-Hydroxy-4-oxo--end group

JOURNAL : J. Chromatogr. VOL : 318 PAGE : 122 -124 (1985)

[TOP]

[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

Page 8: astaxanthin from lipid bank

JOURNAL : Helv. Chim. Acta VOL : 63 PAGE : 1711 -1718 (1980)

[TOP]

[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 -Jonon. I. Erschliessung der enantiomeren C15-Wittig salze durch chemische und mikrobiologishe Racematspaltung von ( )-3-Acetoxy-4-oxo--jonon

JOURNAL

: Helv. Chim. Acta

VOL : 64 PAGE : 2419 -2435 (1981)[TOP]

[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)[TOP]

[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)

[TOP]

[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)

Page 9: astaxanthin from lipid bank

[TOP]

[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)

[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]

[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]

[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)

Page 10: astaxanthin from lipid bank

JOURNAL : Helv. Chim. Acta VOL : 63 PAGE : 1473 -1490 (1980)

[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]

[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)

[TOP]

[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)

[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]

[0213]

Page 11: astaxanthin from lipid bank

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)

[TOP]

[0215]

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

[TOP]

[0216]

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

[TOP]

[0218]

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)

[TOP]

[0219]

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)

[TOP]

[0230]

AUTHOR : Shimidzu,N.,Goto,M., and Miki,W.

Page 12: astaxanthin from lipid bank

TITLE : Carotenooids as Singlet Oxygen Quenchers in Marine Organisms. JOURNAL : Fisheries Sci. VOL : 62 PAGE : 134 -137 (1996)

[TOP]

[0406]

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)

[TOP]

[0407]

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)

[TOP]

[0408]

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)

[TOP]

[0417]

AUTHOR : Katsuyama,M., and Matsuno,T.

TITLE :Carotenoid and vitanin A, and metabplism of carotenoids, -carotene, canthaxanthin, astaxanthin, zeaxanthin, lutein and tunaxanthin in tilapia Tilapia nilotica

JOURNAL : Comp. Biochem. Physiol. VOL : 90 PAGE : 131 -139 (1988)

[TOP]

[0418]

AUTHOR : Rønneberg,H.,Renstrom,B.,Aareskjold,K.,Liaaen-

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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)

[TOP]

[0419]

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)

[TOP]

[0420]

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)

[TOP]

[0421]

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)

[TOP]

[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)

[TOP]

[0423]

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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)

[TOP]

[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)

[TOP]

[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)[TOP]

[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)

[TOP]

[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)

[TOP]

Page 15: astaxanthin from lipid bank

[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)[TOP]

[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)

[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]

[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]

[1007]

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

[TOP]

Page 16: astaxanthin from lipid bank

[1008]

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)

[TOP]

[1009]

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)

[TOP]

[1010]

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)

[TOP]

[1011]

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

JOURNAL : FEBS Lett.VOL : 364 PAGE : 125-128 (1995)

[TOP]

[1012]

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.

Page 17: astaxanthin from lipid bank

VOL : 48 Pt 2 PAGE : 543-548 (1998)[TOP]

[1140]

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)

[TOP]

[1145]

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

[TOP]

[1147]

AUTHOR : Hanagata, N. and Dubinsky, Z.

TITLE :Secondary carotenoid accumulation in Scenedesmus komarekii (Chlorophyceae, Chlorophyta)

JOURNAL : J. Phycol. VOL : 35 PAGE : 960 -966 (1999)

[TOP]

[1164]

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)

[TOP]

[1207]

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

Page 18: astaxanthin from lipid bank

JOURNAL : Pure Appl. Chem. VOL : 71 PAGE : 2273 -2278 (1999)

[TOP]

[1256]

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)

[TOP]

[1257]

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)

[TOP]

[1273]

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)

[TOP]

[1274]

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)

[TOP]

[1275]

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.

Page 19: astaxanthin from lipid bank

TITLE :Unravelling the structural chemistry of the colouration mechanism in lobster shell

JOURNAL : Acta Cryst. VOL : 59 PAGE : 2072 -2082 (2003)

[TOP]

[1276]

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)

[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]

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