Abstract
From the water-insoluble lipid fraction of the methylene chloride/methanol extract of the starfish Cosmasterias lurida, two new glucosylceramides together with a known glucosylceramide, ophidiacerebroside E, were isolated by chromatographic procedures and characterized by spectroscopic (1H and 13C nuclear magnetic resonance, mass spectrometry) methods. The new compounds were identified as (2S, 3R, 4E, 8E, 10E)-1-(β-d-glucopyranosyloxy)-3-hydroxy-2-[(R)-2-hydroxyheptadecanoyl)amino]-9-methyl-4,8,10-octadecatriene (3) and (2S,3R,4E,8E,10E)-1-(β-d-glucopyranosyloxy)-3-hydroxy-2-[(R)-2-hydroxyoctadecanoyl)amino]-9-methyl-4,8,10-octadecatriene (4).
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Abbreviations
- FAME:
-
fatty acid methyl ester
- GC-MS:
-
gas chromatography-mass spectrometry
- HPLC:
-
high-performance liquid chromatography
- LCB:
-
long chain base
- NMR:
-
nuclear magnetic resonance
- TLC:
-
thin-layer chromatography
References
Higuchi, R., Matsumoto, S., Fujita, M., Komori, T., and Sasaki, T. (1995) Structure of Two New Ganglioside Molecular Species and Biological Activity of the Ganglioside. Liebigs Ann. Chem., 545–550.
Venkannababu, U., Bhandari, S.P.S., and Garg, H.S. (1997) Regulosides A-C: Glycosphingolipids from the Starfish Pentaceraster regulus. Liebigs Ann./Recueil, 1245–1247.
Babu, U.V., Bhandari, S.P.S., and Garg, H.S. (1997) Temnosides A and B, Two New Glycosphingolipids from the Sea Urchin Temnopleurus toreumaticus of the Indian Coast. J. Nat. Prod. 60, 732–734.
Higuchi, R., Inagaki, M., togawa, K., Miyamoto, T., and Komori, T. (1994). Isolation and Structure of Cerebrosides from the Sea Cucumber Pentacta australis. Liebigs Ann. Chem., 653–658.
Jin, W., Rinehart, K.L., and Jares-Erijman, E.A. (1994) Ophidiacerebrosides: Cytotoxic Glycosphingolipids Containing a Novel Sphingosine from a Sea Star. J. Org. Chem., 59, 144–147.
Maier, M.S., Roccatagliata, A.J., and Seldes, A.M. (1993) Two Novel Steroidal Glycoside Sulfates from the Starfish Cosmasterrias lurida, J. Nat. Prod., 56, 939–942.
Roccatagliata, A.J., Maier, M.S., Seldes, A.M., Iorizzi, M., and Minale, L. (1994) Starfish Saponins, Part 2. Steroidal Oligoglycosides from the Starfish Cosmasterias lurida, J. Nat. Prod. 57, 747–754.
Kamano, Y., Higuchi, R., Isobe, R., and Komori, T. (1988) Isolation and Structure of New Cerebrosides. Liebigs Ann. Chem., 19–24.
Higuchi, R., Jhou, J.X., Inukai, K., and Komori, T. (1991) Isolation and Structure of Six New Cerebrosides, Asteriacerebrosides A-F, and Two Known Cerebrosides, Astrocerebroside A and Acanthacerebroside C. Liebigs Ann. Chem., 745–752.
Vincenti, M., Guglielmetti, G., Cassani, G., and Tonini, C. (1987) Determination of Double Bond Position in Diunsaturated Compounds by Mass Spectrometry of Dimethyl Disulfide Derivatives, Anal. Chem. 59, 694–699.
Breitmaier, E. (1987) Carbon-13 NMR Spectroscopy, 3rd edn., pp. 108–116, VCH, Wemheim.
Ojika, M., Yoshino, G., and Sakagami, Y. (1997) Novel Ceramide 1-Sulfates, Potent DNA Topoisomerase I Inhibitors Isolated from the Bryozoa Watersipora cucullata, Tetrahedron Lett. 38, 4235–4238.
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Maier, M.S., Kuriss, A. & Seldes, A.M. Isolation and structure of glucosylceramides from the starfish Cosmasterias lurida . Lipids 33, 825–827 (1998). https://doi.org/10.1007/s11745-998-0277-8
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DOI: https://doi.org/10.1007/s11745-998-0277-8