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Carotenoid


DATA No : VCA0006 INFORMANT : Masayoshi Ito

NAME : (3S,5R,6S,3'R)-5,6-Epoxy-3'-ethanoyloxy-3-hydroxy-7',8'-didehydro-5,6-dihydro-12',13',20'-trinor-b,b-caroten-19,11-olide

COMMON NAME: Pyrrhoxanthin
SYMBOL:
FORMULA: C39H48O6 MOL.WT (average) : 612.795


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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): ethanol 466 (Ref. 0002); hexane 437sh, 459, 487 (Ref. 0002); acetone (473), 485 (Ref. 0238); methanol 341, 427 (shoulder), 448, 475, %III/II=27.4 (Ref. 1052)

IR SPECTRA:nmax(CD Cl3)/cm-1: 3600 and 3570 (OH), 2160 (acetylene) and 1745 (C=O) (Ref. 0002)
nmax(KBr)/cm-1 (phyrroxanthin acetate): 3020, 2955, 2925 and 2855 (CH), 2170 (acetylene), 1756 and 1740 (CO), 1630, 1520 (C=C), 1460 (CH2), 1379 and 1366 (Me), 1244, 1231, 1127, 1043, 1030(C-O), 986 (trans -CH=CH-), 943, 905, 820, 768, 725, 643 (Ref. 0040)

NMR SPECTRA:1H-NMR d(500 MHz, CDCl3): 0.94 (3H, s, 1'-Me), 1.14 (3H, s, 1-Me), 1.16 (6H, s, 1-, 5'-Me), 1.17 (3H, s, 1'-Me), 1.22 (1H, dd, J 12.5, 10, 2'ax-H), 1.53 (2ax-H), 1.60 (1H, br d-like, J 12.5, 2'eq-H), 1.60 (1H, dd, J 14.5, 9, 4'ax-H), 1.80 (1H, ddd, J 12.5, 3, 1.5, 2eq-H), 1.87 (3H, s, 5-Me), 1.96 (3H, s, 9-Me), 2.06 (3H, s, OAc), 2.10 (1H, dd, J 17, 9, 4ax-H), 2.19 (3H, s, 13'-Me), 2.36 (1H, ddd, J 14.5, 5, 1.5, 4'eq-H), 2.46 (1H, br dd, J 17, 5, 4eq-H), 3.87 (1H, m, 3'-H), 5.00 (1H, m, 3-H), 5.70 (1H, s, 12'-H), 6.34 (1H, d, J 15.5, 8'-H), 6.36 (1H, dd, J 14.5, 11.5, 12-H), 6.40 and 6.41 (each 1H, d, J 11.5, 10-H, 14'-H), 6.46 (1H, dd, 14, 11.5, 15-H), 6.54 (1H, dd, J 14.5, 11.5, 11-H), 6.60 (1H, dd, J 14, 11.5, 15'-H), 6.98 (1H, s, 10'-H) and 7.14 (1H, d, J 15.5, 7'-H) (Ref. 0002/0038)
13C-NMR d(100.6 MHz, CDCl3): 36.12, 35.31 (1, 1'), 42.29, 47.12 (2, 2'), 67.90, 67.52 (3, 3'), 37.54, 40.94 (4, 4'), 137.26, 67.52 (5, 5'), 124.27, 70.45 (6, 6'), 90.06, 133.74 (7, 7'), 98.54, 121.79 (8, 8'), 121.00, 124.91 (9, 9'), 134.63, 136.30 (10, 10'), 130.63, 146.93 (11, 11'), 133.74, 119.12 (12, 12'), 134.43 (13'), 137.83 (14'), 136.88, 129.85 (15, 15'), 32.07, 29.52 (16, 16'), 28.67, 24.89 (17, 17'), 22.41, 19.87 (18, 18'), 18.10, 168.73 (19, 19'), 15.43 (20'), 170.70 and 21.39 (AcO) (Ref. 0038)

MASS SPECTRA:m/z (ion, intensity relative to base peak in %) (phyrroxanthin acetate): 654 (M, 21.2), 526 (M-28, 0.7), 612 (M-42, 1.2), 594 (M-60, 5.0), 579 (M-75, 2.3), 574 (M-80, 1.0), 562 (M-92, 1.2), 478 (5.7), 450 (1.8), 303 (10.7), 285 (10.6), 233 (7.6), 223 (15.3) (Ref. 0040/0238)

OTHER SPECTRA:CD data: De 215 (-7.3), 218 (-5.4), 224 (-6.3), 228 (-5.3), 233 (-5.4), 242 (-5.0), 252 (-6.6), 260 (-7.0), 285 (-2.1), 321 (-1.1) (Ref. 0081)
CHROMATOGRAM DATA
HPLC (column: LiChrosorb CN(7 mm) 0.7times25 cm, eluent: acetone-hexane 12:88, flow: 2.0 ml/min) tR = 20.5 min (Ref. 0002)
TLC (silica plates, acetone-heptane, 2:8) Rf=0.11 (Ref. 0238)
TLC (alkaline plates, acetone-heptane, 3:7) Rf=0.41 (Ref. 0238>
SOURCE
Marine dinoflagellate (Gyrodinium resplendens, Amphidinium carterae, etc.) (Ref. 0039/0040)
CHEMICAL SYNTHESIS
Rection with the C15-5,6-epoxy-formyl ester with the C22-acetylenic sulphone in the presence of LDA at -78degC provided pyrroxanthin accompanying with its 11'E-isomer. (Ref. 0002)
METABOLISM

GENETIC INFORMATION

NOTE

REFERENCES
[0002]
AUTHOR:Yamano,Y. and Ito,M.
TITLE:First Total Synthesis of pm-Peridinin, pm-Pyrrhoxanthin and the Optically Active Peridinin
JOURNAL:J. Chem. Soc., Perkin Trans. 1
VOL: PAGE : 1599 -1610 (1993)
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[0038]
AUTHOR:Englert,G.,Aakermann,T., and Liaaen-Jensen,S.
TITLE:NMR Studies on Natural All-trans-(9'Z,11'Z)-(3R,3'S,5'R,6'R)-Pyrrhoxanthin, an Acetylenic C37-Skeletal Nor-Carotenoid Butenolide
JOURNAL:Magn. Reson. Chem.
VOL:31 PAGE : 910 -915 (1993)
[TOP]

[0039]
AUTHOR:Loeblich,III,A.R. and Smith,V.E.
TITLE:Chloroplast Pigments of the Marine Dinoflagellate Gyrrodinium resplendens
JOURNAL:Lipids
VOL:3 PAGE : 5 -13 (1968)
[TOP]

[0040]
AUTHOR:Johansen,J.E.,Svec,W.A.,Liaaen-Jensen,S., and Haxo,F.T.
TITLE:Carotenoids of the Dinophyceae
JOURNAL:Phytochemistry
VOL:13 PAGE : 2261 -2271 (1974)
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[0081]
AUTHOR:Aakermann,T., and Liaaen-Jensen,S.
TITLE:Pyrrhoxanthin, reisolation and absolute configuration
JOURNAL:Phytochemistry
VOL:31 PAGE : 1779 -1782 (1992)
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[0238]
AUTHOR:Bjerkeng,B., Hertzberg,S., and Liaaen-Jensen,S.
TITLE:Carotenoids in Food Chain Studies - V. Carotenoids of the Bivalves Modiolus Modiolus and Pecten maximus - Structural, Metabolic and Food Chain Aspects.
JOURNAL:Comp. Biochem. Physiol.
VOL:106 PAGE : 243 -250 (1993)
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[1052]
AUTHOR:Takaichi, S. and Shimada, K.
TITLE:Characterization of carotenoids in photosynthetic bacteria
JOURNAL:Methods Enzymol.
VOL:213 PAGE : 374 -385 (1992)
[TOP]

Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.