POLAR GLYCOSPHINGOLIPIDS IN INSECT - CHEMICAL STRUCTURES OF GLYCOSPHINGOLIPID SERIES CONTAINING 2'-AMINOETHYLPHOSPHORYL-(-]6)-N-ACETYLGLUCOSAMINE AS A POLAR GROUP FROM LARVAE OF THE GREEN-BOTTLE FLY, LUCILIA-CAESAR

A series of glycosphingolipids containing 2'-aminoethylphosphoryl(--> 6)-N-acetylglucosamine as a polar group has been demonstrated in larvae of the green-bottle fly, Lucilia caesar. The thin-layer chromatographic pattern of the total polar glycolipid revealed the presence of more than eight components, of which five major components were purified by the use of successive column chromatography on QAE- and DEAE-Sephadex and silicic acid (Iatrobeads). From structural studies including compositional sugar analysis, hydrogen fluoride degradation, proton magnetic resonance spectroscopy, methylation analysis, and fast atom bombardment mass spectrometry, their structures were deduced to be as follows: 2'-aminoethylphosphoryl --> 6GlcNAc-beta-1-3Man-beta-1-4Glc-beta-1-Cer, GalNAc-beta-1-4(2'-aminoethylphosphoryl --> 6)GlcNAc-beta-1-3Man-beta-1-4Glc-beta-1-Cer, Gal-beta-1-3GalNAc-alpha-1-4GalNAc-beta-4(2'-aminoethyylphosphoryl --> 6)GlcNAc-beta-1-3Man-beta-1-4Glc-beta-1-Cer, and GlcNAc-beta-1-3Gal-beta-1-3GalNAc-alpha-1-4GalNAc-beta-1-4(2'Gal-beta-1-3GalNAc-alpha-1-4GalNAc-beta-1-4(2'-aminoethylphosphoryl --> 6)GlcNAc-beta-1-3Man-beta-1-4Glc-beta-1-Cer. The main molecular species of the ceramide moiety was arachidinyltetradecasphingenine in all of the major glycolipids.