Ophidiacerebrosides: cytotoxic glycosphingolipids containing a novel sphingosine from a sea star

The Journal of Organic Chemistry
1994.0

Abstract

Five newly identified glycosphingolipids, ophidiacerebrosides, have been isolated from the sea star Ophidiaster ophidianus. All five compounds showed strong cytotoxicity against L1210 leukemia cells in vitro. On the basis of chemical evidence and ¹H and ¹³C NMR and mass spectra, the structure of ophidiacerebroside C, the major component, is assigned as (2S,3R,4E,8E,10E)-1-(β-d-glucopyranosyloxy)-3-hydroxy-2-[((R)-2-hydroxydocosanoyl)amino]-9-methyl-4,8,10-octadecatriene. This compound differs from previously isolated marine cerebrosides in that the sphingosine base contains a methyl branch and a conjugated diene. The other four ophidiacerebrosides, A, B, D, and E, were found from their FAB and ¹H NMR spectra and hydrolysis products to be identical to C with respect to the sphingosine and hexose units. However, the α-hydroxy fatty acids for the minor components differed in chain length.

Knowledge Graph

Similar Paper

Ophidiacerebrosides: cytotoxic glycosphingolipids containing a novel sphingosine from a sea star
The Journal of Organic Chemistry 1994.0
Oreacerebrosides: Bioactive Cerebrosides with a Triunsaturated Sphingoid Base from the Sea Star <i>Oreaster reticulatus</i>
European Journal of Organic Chemistry 2007.0
Biologically active glycosides from asteroidea, XIII. Glycosphingolipids from the starfish <i>Acanthaster planci</i>, 2. Isolation and structure of six new cerebrosides
Liebigs Annalen der Chemie 1988.0
Biologically active glycosides from asteroidea, XXII. Glycosphingolipids from the starfish <i>Astropecten latespinosus</i>, I. Structures of three new cerebrosides, astrocerebroside A, B, and C and of related nearly homogeneous cerebrosides
Liebigs Annalen der Chemie 1990.0
Biologically active glycosides from asteroidea, XXVIII. Glycosphingolipids from the starfish <i>Asterias amurensis versicolor</i> Sladen, 1. Isolation and structure of six new cerebrosides, asteriacerebrosides AF, and two known cerebrosides, astrocerebroside A and acanthacerebroside C
Liebigs Annalen der Chemie 1991.0
Isolation and Structure of Four New Ceramides from the Starfish Luidia maculata
Chemical and Pharmaceutical Bulletin 2006.0
Biologically active glycosides from asteroidea, XX. Glycosphingolipids from the starfish <i>Asterina pectinifera</i>,1. Isolation and characterization of acanthacerebroside B and structure elucidation of related, nearly homogeneous cerebrosides
Liebigs Annalen der Chemie 1990.0
Isolation and Structure of Three New Ceramides from the StarfishAcanthaster planci
European Journal of Organic Chemistry 1998.0
Isolation and Structure Determination of Six Glucocerebrosides from the Starfish Luidia maculata.
Chemical and Pharmaceutical Bulletin 2002.0
Biologically active glycosides from asteroidea, XVII. Glycosphingolipids from the starfish <i>Acanthaster planci</i>, 3. Isolation and structure of two new ceramide lactosides
Liebigs Annalen der Chemie 1988.0