GLUCOSYLCERAMIDE HAVING A NOVEL TRI-UNSATURATED LONG-CHAIN BASE FROM THE SPERMATOZOA OF THE STARFISH, ASTERIAS-AMURENSIS

Glucosylceramide (Glcβ1-1Cer) 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-diol (d18: 3) and (4E, 8E, 10E)-2-amino-9-methyl-4, 8, 10-octa-decatriene-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. © 1990 COPYRIGHT, 1990 BY THE JOURNAL OF BIOCHEMISTRY.