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Carotenoid


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
SYMBOL:
FORMULA: C40H52O4 MOL.WT (average) : 596.838


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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).

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).
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:216-218degC (Ref. 0010)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:

DENSITY:

SOLUBILITY:
SPECTRAL DATA
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)
CHROMATOGRAM DATA
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).
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, a-3 subclass of the Proteobacteria) (Ref. 1012)
CHEMICAL SYNTHESIS
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)
METABOLISM
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).
GENETIC INFORMATION
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).
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).
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