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Carotenoid


DATA No : VCA0063 INFORMANT : Masayoshi Ito

NAME : (3S,5R,6S,3'S,5'R,6'R)-5,6:3',6'-Diepoxy-5,6,5',6'-tetrahydro-b,b-carotene-3,5'-diol

COMMON NAME: Cucurbitaxanthin B
SYMBOL:
FORMULA: C40H56O4 MOL.WT (average) : 600.870


Download ChemDraw structure data
BIOLOGICAL ACTIVITY

PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:lmax (nm): benzene 483, 453, 427 (Ref. 0505); ether 415, 438, 468(Ref. 0510)

IR SPECTRA:nmax(KBr)/cm-1: 3360m (OH), 2900s, 2850m, 1440w, 1379w, 1352w, 1292w, 1238w, 1085m, 1034m, 956s, 870w, 820w (Ref. 0510)

NMR SPECTRA:1H-NMR d(400 MHz, CDCl3): 0.88 (3H, s, 17-Me), 0.98 (3H, s, 16'-Me), 1.15 (3H, s, 17'-Me), 1.19 (3H, s, 18'-Me), 1.21 (3H, s, 18-Me), 1.24 (1H, m, 2-Hax), 1.43 (3H, s 16-Me), 1.61 (1H, d, J 11.6, 2-Heq), 1.67 (1H, d, J 12.1, 4-Heq), 1.73 (3H, s, 18'-Me), 1.77 (1H, ddd, J 12.0, 3.6, 2.1, 2'-Heq), 1.84 (1H, ddd, J 11.5, 6, 2.2, 2-Hax), 1.93 (3H, s, 19'-Me), 1.95 (3H, s, 19-Me), 1.96 (6H, s 20, 20'-Me), 2.06 (1H, ddd, J 12.1, 6.0, 2.2, 4-Hax), 2.39 (1H, ddd, J 14.3, 5.2, 1.8, 4-Heq), 3.91 (1H, m, 3'-H), 4.39 (1H, t, J 6.0, 3-H), 5.74 (1H, d, J 16.1, 7-H), 5.88 (1H, d, J 15.5, 7'-H), 6.20 (1H, d, J 11.4, 10'-H), 6.21 (1H, d, J 11.4, 10-H), 6.26 (2H, m, 14, 14'-H), 6.29 (1H, d, J 15.5, 8'-H), 6.36 (1H, d, J 14.7, 12-H), 6.37 (1H, d, J 16.1, 8-H),6.37 (1H, d, J 14.7, 12'-H), 6.60 (1H, dd, J 11.5, 14.7, 11'-H), 6.61 (1H, dd J 11.5, 14.7, 11-H), 6.63 (2H, m, 15, 15'-H) (Ref. 0505/0510)
13C-NMR d(100.6 MHz, CDCl3): 12.9 (C19, 19', 20, 20'), 20.1 (C18'), 25.1 (C16'), 25.9 (C16), 29.7 (C17'), 31.8 (C18), 32.3 (C17), 41.3 (C4'), 47.9 (C2'), 48.2 (C4), 48.9 (C2), 65.0 (C3'), 123.0 (C7), 123.9 (C7'),124.7 (C11'), 124.8 (C11), 130.1 (C15, 15'), 132.2 (C10, 10'), 132.8 (C14, 14'), 135.0 (C8), 137.6 (C8'), 138.3 (C12,12') (Ref. 0505)

MASS SPECTRA:m/z: 600 (50, M), 582 (9, M-H2O), 564 (3, M-2H2O), 520 (21), 508 (21), 287 (36), 286 (32), 221 (100), 181 (57), 160 (45), 155 (26), 119 (32), 105 (26), 55 (10), 43 (25) (Ref. 0505/0510)

OTHER SPECTRA:CD in EPA: De 228 (+2.13), 267 (-5.77), 327 (+0.94) (Ref. 0505)CD in EPA: De 210 (-6.8), 225 (0), 230 (+3.0), 236 (0), 267 (-19.0), 309 (0), 327 (+2.0), 340 (0) (Ref. 0510)
CHROMATOGRAM DATA

SOURCE
Cucurbita maxima (Pumpkin) (Ref. 0510)
Capsicum annuum (Red paprika) (Ref. 0508/0505/0506)
CHEMICAL SYNTHESIS

METABOLISM
Antheraxanthin -> cucurbitaxanthin A -> cucurbitaxanthin B in Capsicum annuum (Ref. 0511)
Cucurbitaxanthin B is the substrate of violaxanthin de-epoxidase (Ref. 1143).
GENETIC INFORMATION

NOTE
Note: Left and right end groups on the chemical structure have been reversed.
REFERENCES
[0505]
AUTHOR:Deli,J.,Molnar,P., Matus,Z.,Toth,G., and Steck,A.
TITLE:Reisolation of Carotenoid 3,6-Epoxides feom Red Paprika (Capsicum annuum)
JOURNAL:Helv. Chim. Acta.
VOL:79 PAGE : 1435 -1443 (1996)
[TOP]

[0506]
AUTHOR:Deli,J.,Matus,Z., and Toth,G.
TITLE:Carotenoid Composition in the Fruits of Capsicum annuum Cv. Szentesi Kosszarvu during Ripening
JOURNAL:J. Agric. Food Chem.
VOL:44 PAGE : 711 -716 (1996)
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[0508]
AUTHOR:Deli,J.,Molnar,P.,Toth,G.,Baumeler,A., and Eugster,C.H.
TITLE:Cycloviolaxanthin (=(3S,5R,6R,3'S,5'R,6'R)-3,6:3',6'-Diepoxy-5,6,5',6'-tetrhydro-b,b-carotin-5,5'-diol), eine neues Carotinoid aus Paprika (Capsicum annuum)
JOURNAL:Helv. Chim. Acta
VOL:74 PAGE : 819 -824 (1991)
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[0510]
AUTHOR:Matsuno,T.,Tani,Y.,Maoka,T.,Matsuo,K., and Komori,T.
TITLE:Isolation and structural elucidation of cucurbitaxanthin A and B from pumpkin Cucurbita maxima
JOURNAL:Phytochemistry
VOL:25 PAGE : 2837 -2840 (1986)
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[0511]
AUTHOR:Hornero-Mendez,D., and Minguez-Mosquera,M.,I.
TITLE:Isolation and Identification of the Carotenoid Capsolutein from Capsicum annuum as Cucurbitaxanthin A
JOURNAL:J. Agric. Food Chem.
VOL:46 PAGE : 4087 -4090 (1998)
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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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