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Carotenoid


DATA No : VCA0008 INFORMANT : Masayoshi Ito

NAME : (3R,3'S,5'R)-3,3',8'-Trihydroxy-7,8-didehydro-b,k-carotene-6'-one

COMMON NAME: Mytiloxanthin
SYMBOL:
FORMULA: C40H54O4 MOL.WT (average) : 598.854


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BIOLOGICAL ACTIVITY
Inhibitotory effect on Epstein-Barr virus activation (anti-tumor promotion) (Ref. 0217)
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:147degC (Ref. 0035/0051)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:lmax (nm): ether 294, 469 (Ref. 0050); CS2 496 (Ref. 0051); ethanol 470 (Ref. 0051); benzene 480 (e 85700) (Ref. 0051); acetone 470 (Ref. 0238)

IR SPECTRA:nmax(CD Cl3)/cm-1: 3680, 3610, 2950, 2920, 2850, 2170, 1605, 1560, 1460, 1380, 1100, 1050, 1030, 970 (Ref. 0051)
nmax(CD Cl3)/cm-1 : 2170, 965 (Ref. 0051)

NMR SPECTRA:1H-NMR d(300 MHz, CDCl3): 1.46 (dd, J 12, 12, 2ax-H), 1.84 (ddd, J 12, 3.5, 2), 3.99 (dddd, J 12, 9.5, 5.5, 3.5, 3-H), 2.07 (dd, J 17.5, 9.5, 4ax-H), 2.43 (dd, ddd, J 17.5, 5.5, 2, 4eq-H), 6.46 (d, J 11.5, 10-H), 6.54 (dd, J 14.5, 11.5, 11-H), 6.36 (d, J 14.5, 12-H), 6.28 (d, J 10.5, 14-H), 6.70 (d, J 14, 10.5, 15-H), 1.15 (s, 1ax-Me), 1.20 (s, 1eq-Me), 1.93 (s, 5-Me), 2.01 (s, 9-Me), 1.98 (s, 13-Me), 2.19 (dd, J 13.5, 8, 2'a-H), 1.72 (dd, J 13.5, 4.5, 2'b-H), 4.53 (dddd, J 8.5, 8, 4.5, 2.5, 3'-H), 2.88 (dd, J 14.5, 8.5, 4'a-H), 1.55 (dd, J 14.5, 2.5, 4'b-H), 5.86 (s, 7'-H), 7.23 (d, J 9.5, 10'-H), 6.62 (dd, J 15, 9.5, 11'-H), 6.65 (d, J 15, 12'H), 6.38 (d, J 10.5, 14'-H), 6.65 (dd, J 14, 10.5, 15'-H), 0.85 (s, 1'a-Me), 1.19 (s, 1'b-Me), 1.35 (s, 5'b-Me), 1.98 (s, 9'Me), 1.99 (s, 13'-Me), 16.30 (s, 8'-OH). (Ref. 0050)

MASS SPECTRA:EI-MS m/z (ion, intensity relative to base peak in %): 598 (M, 23), 580 (M-18, 5), 562 (M-36, 1), 471 (M-127, 1), 401 (M-197, 20), 197 (17), 179 (25), 109 (90), 92 (100) (Ref. 0035/0050/0238)

OTHER SPECTRA:CD data in ether solution: De 225 (-0.5), 280 (0), 294 (+0.7), 305 (0), 360 (-1.0) (Ref. 0050/0051)
CHROMATOGRAM DATA
TLC (silica plates on alkaline plates, trichloroethane-MeOH, 100:5) Rf=0.36 (Ref. 0238)
HPLC (columun: Shim-Pak Prep-ODS (Shimadzu) (5mm) 2.0times25 cm, eluent: CH2Cl2-MeCN 5:95, flow: 10 ml/min) tR = ca. 7 min [[Maoka Takashi]
SOURCE
Sea squirts (Halocynthia roretzi) (Ref. 0035)
Mussel (Mytilus coruscus, Mytilus edulis, Mytilus californianus) (Ref. 0050/0051/0052/0426/0427/0434)
CHEMICAL SYNTHESIS
Condensation of 1-acetyl-1,2,2-trimethyl-4-trimethylsilyloxycyclopentane with methyl 12,12-ethylenedioxy-2,6,11-trimethyldodeca-2,4,6,8,10-pentaenoate, and removal of the protecting group, gave the b-diketone derivatives, which reacted with the C15-acetylenic Wittig salt to yield a cis-isomer of mytiloxanthin. Mytiloxanthin itself has not been synthesized. (Ref. 0051)
METABOLISM

GENETIC INFORMATION

NOTE

REFERENCES
[0035]
AUTHOR:Matsuno,T.,Ookubo,M.,Nishizawa,T., and Shimizu,I.
TITLE:Carotenoids of Sea Squirts. I. New Marine Carotenoids, Halocynthiaxanthin and Mytiloxanthinone from Halocynthia reretzi
JOURNAL:J. Chromatogr.
VOL:32 PAGE : 4309 -4315 (1984)
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[0050]
AUTHOR:Maoka,T. and Fujiwara,Y.
TITLE:Absolute Configurations of Mytiloxanthin and 9-E-Mytiloxanthin
JOURNAL:J. Jpn. Oil Chem. Soc.
VOL:45 PAGE : 667 -970 (1996)
[TOP]

[0051]
AUTHOR:Chopra,A.K.,Khare,A.,Moss,G.P., and Weedon,B.C.L.
TITLE:Carotenoids and related compounds. Part 41. Structure of mytiloxanthin and synthesis of a cis-isomer
JOURNAL:J. Chem. Soc., Perkin Trans. 1
VOL: PAGE : 1383 -1388 (1988)
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[0052]
AUTHOR:Sheer,B.T.
TITLE:Some features of the metabolism of the carotenoid pigments in the California sea mussel (Mytilus californianus)
JOURNAL:J. Biol. Chem.
VOL:136 PAGE : 275 -299 (1940)
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[0217]
AUTHOR:Tsushima, M., Maoka, T., Katsuyama, M., Kozuka, M., Matsuno, T., Tokuda, H., Nishino, H., and Iwashima, A.
TITLE:Inhibitory effect of natural carotenoids on Epstein-Barr virus activation activity of a tumor promoter in Raji cells. A screening study for anti-tumor promoters PubMed ID:7742789
JOURNAL:Biol Pharm Bull.
VOL:18 PAGE : 227-233 (1995)
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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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[0426]
AUTHOR:Hertzberg,S.,Partali,V., and Liaaen-Jensen,S.
TITLE:Animal carotenoids. 32. Carotenoids of Mytilus edulis (Edible mussel)
JOURNAL:Acta Chem. Scand.
VOL:42 PAGE : 495 -503 (1988)
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[0427]
AUTHOR:Matsuno,T., and Maoka,T.
TITLE:Isolation of a new carotenoid, 3,4,3'-trihydroxy-7',8'-didehydro-b-carotene-3,4,3'-triol from dea mussels
JOURNAL:Bull. Jap. Soc. Sci. Fish.
VOL:47 PAGE : 377 -384 (1981)
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[0434]
AUTHOR:Khare,A.,Moss,G.P., and Weedon,B.C.L.
TITLE:Mytiloxanthin and isomytiloxanthin, two novel acetylenic carotenoids
JOURNAL:Tetrahedron Lett.
VOL: PAGE : 3921 -3924 (1973)
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