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Carotenoid


DATA No : VCA0013 INFORMANT : Masayoshi Ito

NAME : (3S,3'S)-3-(b-D-Glucopyranosyloxy)-3'-hydroxy-b,b-carotene-4,4'-dione

COMMON NAME: Astaxanthin glucoside
SYMBOL:
FORMULA: C46H62O9 MOL.WT (average) : 758.979


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BIOLOGICAL ACTIVITY

PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:lmax (nm): benzene 487 (Ref. 0085)

IR SPECTRA:

NMR SPECTRA:1H-NMR d(CDCl3): 2.04 (t, J 14, 2-H), 2.15 (dd, J 14, 6, 2-H), 4.40 (dd, J 14, 6, 3-H), 1.23 and 1.35 (s, 1-gem-Me), 1.91 (s, 5-Me), 1.81 (t, J 13, 2'-H), 2.16 (dd, J 13, 6, 2'-H), 4.32 (ddd, 13, 6, 2, 3'-H), 1.21 and 1.32 (s, 1'-gem-Me), 1.94 (s, 5'-Me), 1.99-2.01 (s, 19,19',20,20'-Me), 6.20-6.70 (14H, m, olefinic-H), 4.57 (d, J 8, 1''-H), 3.45 (dd, J 9, 8, 2''-H), 3.61 (m, 3''-H), 3.61 (m, 4''-H), 3.41 (m, 5''-H), 3.83 and 3.93 (m, 6''-H2) (Ref. 0085)
13C-NMR d(CDCl3): 37.4 (1), 44.7 (2), 77.6 (3), 199.3 (4), 127.9 (5), 162.4 (6), 123.0 (7), 142.7 (8), 134.4 (9), 135.5 (10), 124.5 (11), 140.0 (12), 136.8 (13), 134.0 (14), 130.6 (15), 26.6 and 30.6 (1-gem-Me), 14.1 (5-Me), 12.59 (9-Me), 12.84 (13-Me), 36.8 (1'), 45.5 (2'), 69.2 (3'), 200.4 (4'), 126.9 (5'), 162.2 (6'), 123.3 (7'), 142.3 (8'), 134.6 (9'), 135.1 (10'), 124.7 (11'), 139.7 (12'), 136.7 (13'), 133.8 (14'), 130.8 (15'), 26.2 and 30.8 (1'-gem-Me), 14.0 (5'-Me), 12.58 (9'-Me), 12.83 (13'-Me), 104.9 (1''), 74.3 (2''), 77.2 (3''), 70.3 (4''), 75.7 (5''), 62.7 (6'') (Ref. 0085)

MASS SPECTRA:HRFABMS m/z: 759.4474 [M+H]+ (Ref. 0085)

OTHER SPECTRA:CD data: De 242 (-12.0), 274 (+10.1), 314 (-18.5) (Ref. 0085)
CHROMATOGRAM DATA
HPLC (columun: TSK gel ODS-80Ts (Tosoh) 0.46times15 cm, eluent and flow: 1.0 ml/min, H2O-MeOH 5:95 for 5 min, then 5 min-linear gradient MeOH-THF 7:3) tR = 3.92 min
[Chromatogram 0011] (Ref. 0085)
SOURCE
Agrobacterium aurantiacum (marine bacterium; present name, Paracoccus sp. N81106) (Ref. 0085) It has recently been shown that this bacterium belongs to Paracoccus species according to their16S rDNA analysis, performed by T. Hamada of Marine Biotechnology Institute (DDBJ accession number: AB008114).
CHEMICAL SYNTHESIS

METABOLISM

GENETIC INFORMATION
Escherichia coli, which carries the Erwinia crtE, crtB, crtI, crtY, crtZ, and crtX genes and the crtW gene of Agrobacterium aurantiacum, accumulates astaxanthin-b-glucoside in addition to astaxanthin-b-D-diglucoside of the final product (Ref. 1027).
NOTE

REFERENCES
[0085]
AUTHOR:Yokoyama,A.,Adachi,K., and Shizuri,Y.
TITLE:New Carotenoid Glucosides, Astaxanthin Glucoside and Adonixanthin Glucoside, Isolation from the Astaxanthin-Producing Marine Bacterium Agrobacterium aurantiacum
JOURNAL:J. Nat. Prod.
VOL:58 PAGE : 1929 -1933 (1995)
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[1027]
AUTHOR:Yokoyama, A., Shizuri, Y., and Misawa, N.
TITLE:Production of new carotenoids, astaxanthin glucosides, by Escherichia coli transformants carrying carotenoid biosynthetic genes
JOURNAL:Tetrahedron Lett.
VOL:39 PAGE : 3709 -3712 (1998)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.