Characterization of cerebroside (monoglycosylceramide) from the sea anemone, Metridium senile. Identification of the major long-chain base as an unusual dienic base with a methyl branch at a double bond.
1. Cerebroside of the sea anemone, Metridium senile, has been isolated (0.6 mg/g dry tissue weight) and structurally characterized. 2. The structure was shown by mass spectrometry, NMR spectroscopy and degradative studies as beta-glucopyranosylceramide. The major fatty acids were 16 : 0 and 20 : 0 D-2-hydroxy fatty acids. The major base was a novel base, D-erythro-1,3-dihydroxy-2-amino-9-methyl-trans-4, trans-8-octadecadiene. 3. Some unusual fatty acids of marine origin are suggested to originate in this long-chain base by metabolic conversion. 4. The implication of the methyl branch position of the base on our current view of sphingolipid function in the plasma membrane is discussed.
D000818:Animals; D002554:Cerebrosides / Q000302:isolation & purification*; D003063:Cnidaria / Q000032:analysis*; D005227:Fatty Acids / Q000032:analysis; D005963:Glucosylceramides / Q000302:isolation & purification*; D013058:Mass Spectrometry; D008956:Models, Chemical; D012615:Sea Anemones / Q000032:analysis*
D002554:Cerebrosides; D005227:Fatty Acids; D005963:Glucosylceramides