Glucosylceramide having a novel tri-unsaturated long-chain base from the spermatozoa of the starfish, Asterias amurensis.
Glucosylceramide (Glc beta 1-1Cer) was isolated from the spermatozoa of the starfish, Asterias amurensis. The long-chain bases of the glycolipid consisted of dihydroxy (d18:2, d18:3, d19:3, and d22:2), and trihydroxy (t22:1) types. Long-chain aldehydes derived from them were analyzed mainly by proton nuclear-magnetic resonance to determine the detailed structures. Two of the tri-unsaturated bases were identified as (4E,8E,10E)-2-amino-4,8,10-octadecatriene-1,3-di ol (d18:3) and (4E,8E,10E)-2-amino-9-methyl-4,8,10-octadecatriene+ ++-1,3-diol (d19:3), which is a novel base. Both d22:2 and t22:1 had a cis double bond at the C9 or C13 position. All fatty acids were 2-hydroxylated (C14-C25): Most of them were saturated and unbranched. About 10% was mono-unsaturated and unbranched (C22-C25), while saturated but branched (iso- and anteiso-types) C15-C18 acids were found as minor components. The main fatty acids, which summed up to more than 93% of the fatty acids in the glucosylceramide, were n-14h:0, n-15h:0, n-16h:0, n-17h:0, n-18h:0, and n-24h:1.
Irie
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A
Department of Life Science, Faculty of Science, Tokyo Institute of Technology.
Kubo
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Hoshi
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D000447:Aldehydes / Q000032:analysis; D000818:Animals; D002240:Carbohydrate Sequence; D002554:Cerebrosides / Q000032:analysis*; D002851:Chromatography, High Pressure Liquid; D005231:Fatty Acids, Unsaturated / Q000032:analysis*; D005963:Glucosylceramides / Q000032:analysis*; D007536:Isomerism; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D013058:Mass Spectrometry; D008969:Molecular Sequence Data; D009993:Osmium Tetroxide / Q000494:pharmacology; D013094:Spermatozoa / Q000032:analysis*; D013215:Starfish / Q000032:analysis*
D000447:Aldehydes; D002554:Cerebrosides; D005231:Fatty Acids, Unsaturated; D005963:Glucosylceramides; D009993:Osmium Tetroxide