Biologically active glycosides from asteroidea, XIII. Glycosphingolipids from the starfish <i>Acanthaster planci</i>, 2. Isolation and structure of six new cerebrosides

Abstract

Abstract Six new cerebrosides (ceramide monohexosides), acanthacerebroside A ( 1 ), B ( 2 ), C ( 3 ), D ( 4 ), E ( 5 ), and F ( 6 ) were isolated from the water‐insoluble lipid fraction of the chloroform‐methanol extract of the starfish Acanthaster planci . On the basis of chemical and spectral evidences, they were characterized as 1‐ O ‐(β‐ D ‐glucopyranosyl)‐substituted (1 S ,3 S ,4 R )‐2‐[(2 R )‐2‐hydroxytetracosanoylamino]‐1,3,4‐hexadecanetriol ( 1 ), (2 S ,3 S ,4 R )‐2‐[(2 R )‐2‐hydroxyhexadecanoylamino]‐1,3,4‐docosanetriol ( 2 ), (2 S ,3 S ,4 R ,13 E )‐2‐[(2 R )‐2‐hydroxyhexadecanoylamino]‐13‐docosene‐1,3,4‐triol ( 3 ), (2 S ,3 R ,4 E ,10 E )‐2‐[(2 R )‐2‐hydroxydocosanoylamino]‐4,10‐octadecadiene‐1,3‐diol ( 4 ), (2 S ,3 R ,4 E ,10 E )‐2‐[(2 R )‐2‐hydroxydocosanoylamino]‐4,10‐octadecadiene‐1,3‐diol ( 5 ), and (2 S ,3 R ,4 E ,10 E )‐2‐[(2 R )‐2‐hydroxytetracosanoylamino]‐4,10‐octadecadiene‐1,3‐diol ( 6 ). Reversed‐phase HPLC was effective to isolate these cerebrosides revealing the very close resemblance in structure. Negative FABMS spectrometry was useful in providing information on the molecular mass of the cerebrosides.