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Biologically active glycosides from asteroidea, XVII. Glycosphingolipids from the starfish Acanthaster planci , 3. Isolation and structure of two new ceramide lactosides
Author(s) -
Kawano Yasuhiro,
Higuchi Ryuichi,
Isobe Ryuichi,
Komori Tetsuya
Publication year - 1988
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.198819881213
Subject(s) - starfish , chemistry , ceramide , glycoside , acanthaster , glycosphingolipid , chloroform , chromatography , ganglioside , fraction (chemistry) , stereochemistry , biochemistry , ecology , apoptosis , biology , oceanography , great barrier reef , coral reef , geology
Two new ceramide lactosides, acanthalactoside A ( 1 ) and B ( 2 ) were isolated from the water‐soluble lipid fraction of the chloroform/methanol extract of the starfish Acanthaster planci. On the basis of chemical and spectral evidence, the structures of 1 and 2 were characterized as 1‐ O ‐[β‐ D ‐galactopyranosyl‐(1→4)‐β‐ D ‐glucopyranosyl]‐substituted (2 S ,3 S ,4 R )‐2‐[(2 R )‐2‐hydroxytetracosanoylamino]‐1,3,4‐hexadecanetriol ( 1 ) and (2 S ,3 S ,4 R ,13 E )‐2‐[(2 R )‐2‐ hydroxyhexadecanoylamino]‐13‐docosene‐1,3,4‐triol ( 2 ), respectively. Reversed‐phase column chromatography was useful to obtain the glycosphingolipid mixture from the watersoluble lipid fraction containing also other material such as steroid saponins. Reversed‐phase HPLC was also effectual to isolate these ceramide dihexosides reveling very close resemblance in structure. Negative FAB mass spectrometry was successfully used for the determination and confirmation of the ceramide dihexosides.