Abstract
A novel phosphonoglycosphingolipid (AJPnGL) was isolated from eggs of the sea hare Aplysia juliana. The structure was determined to be Gal α1 → 2Gal β1 → 4(2-aminoethylphosphonyl → 6)Glc β1 → 1Cer by FAB/MS, 1H-NMR, hydrogen fluor degradation, methylation analysis, partial acid hydrolysis and GC analysis of the component sugars, fatty acids and long-chain bases. The ceramide moiety of this lipid consisted of branched nonadeca-4-sphingenine and octadeca-4-sphingenine as main long-chain bases and palmitic acid and stearic acid as major fatty acids. Since the sugar chain (Gal α1 → 2Gal β1 → 4Glc β1 →) and the ceramide moiety of AJPnGL were identical with those of the main neutral glycosphingolipid of eggs of A. juliana, the biosynthesis of AJPnGL may occur by the addition of 2-aminoethylphosphonate to the main neutral glycosphingolipid, Gal α1 → 2Gal β1 → 4Glc β1 → 1Cer.
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