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Carotenoid


DATA No : VCA1012 INFORMANT : Norihiko Misawa

NAME : (3S,5R,6S,3'R)-5,6-Epoxy-5,6-dihydro-b,b-carotene-3,3'-diol

COMMON NAME: Antheraxanthin
SYMBOL:
FORMULA: C40H56O3 MOL.WT (average) : 584.871


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BIOLOGICAL ACTIVITY

PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:197 degC(Ref. 1090)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:lmax (nm) (e): diethyl ether/isopentane/ethanol (5:5:2) 269 (20.5), 332 (13.5), 422 (94.0), 445 (136.0), 473 (122.0)(Ref. 1090)

IR SPECTRA:

NMR SPECTRA:1H-NMR (CDCl3): 0.980 s (16-H3), 1.074 s (16', 17'-H3), 1.151 s (17-H3), 1.189 s (18-H3), 1.34 d (J=5 Hz; 3'-OH), 1.737 s (18'-H3), 1.927 s (19-H3), 1.965 s (20-H3), 1.968 s (19'-H3), 1.973 s (20'-H3), 3.88 (3-Hax), ca. 4.00 (3'-Hax), 5.88 (7-H) (Ref. 1090/0079) (Ref. 1329)

MASS SPECTRA:

OTHER SPECTRA:CD l nm (de) diethyl ether/isopentane/ethanol (5:5:2) 180 degC: 217 (-38.1), 242 (36.4), 280 (-55.0), 330 (6.2), 345 (10.6), 408 (2.3), 435 (2.8 , 465 (3.8), 493 (5.2); RT: 216 ()-13.2, 239 (10.3), 275 (-21.1), 335 (5.7) (Ref. 1090/0079) (Ref. 1329)
CHROMATOGRAM DATA

SOURCE
Plants.
(3S,5R,6S,3'R) and (3S,5S,6R,3'R) antheraxanthin are found from the common freshwater goby Rhinogobius brunneus (Ref. 1329).
CHEMICAL SYNTHESIS

METABOLISM
Antheraxanthin is an intermediate through epoxydation reaction from zeaxanthin to violaxanthin by biosynthesis and through de-epoxidation reaction from violaxanthin to zeaxanthin by xanthophyll-cycle.
Antheraxanthin is the substrate of violaxanthin de-epoxidase (Ref. 1143/1144).
[Table 1032]
GENETIC INFORMATION

NOTE

REFERENCES
[0079]
AUTHOR:Bjfrnland,T., Borch,G., and Liaaen-Jensen,S.
TITLE:Algal carotenoids: 29. Configurational studies on red algae carotenoids
JOURNAL:Phytochemistry
VOL:23 PAGE : 1711 -1715 (1984)
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[1090]
AUTHOR:M&anml;rki-Fischer, E., Buchecker, R., Eugster, C.H., Englert, G., Noack, K. and Vecchi, M.
TITLE:Absolute configuration of antheraxanthin, 'cis-antheraxanthin' and of the stereoisomeric mutatoxanthins
JOURNAL:Helv. Chim. Acta
VOL:65 PAGE : 2198 -2221 (1982)
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[1143]
AUTHOR:Grotz, B., Molnár, P, Stransky, H., and Hager, A.
TITLE:Substrate specificity and functional aspects of violaxanthin-de-epoxidase, an enzyme of the xanthophyll cycle
JOURNAL:J. Plant Physiol.
VOL:154 PAGE : 437 -446 (1999)
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[1144]
AUTHOR:Yamamoto, H. Y., and Higashi, R. M.
TITLE:Violaxanthin de-epoxidase. Lipid composition and substrate specificity PubMed ID:102251
JOURNAL:Arch Biochem Biophys.
VOL:190 PAGE : 514-522 (1978)
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[1329]
AUTHOR:Tsushima, M., Mune, E., Maoka, T., and Matsuno, T.
TITLE:Isolationof stereoisomeric epoxy carotenoids and new acetylenic carotenoid from the common freshwater goby Rhinogobius brunneus PubMed ID:10924174
JOURNAL:J Nat Prod.
VOL:63 PAGE : 960-964 (2000)
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