CHARACTERIZATION OF 2 NOVEL PYRUVYLATED GLYCOSPHINGOLIPIDS CONTAINING 2'-AMINOETHYLPHOSPHORYL(-]6)-GALACTOSE FROM THE NERVOUS-SYSTEM OF APLYSIA-KURODAI

Two novel acidic glycosphingolipids containing pyruvylated galactose were purified from the nervous tissue of Aplysia kurodai by successive Iatrobeads column chromatographies. By component analysis, sugar analysis, permethylation studies, fast atom bombardment-mass spectrometry, and proton magnetic resonance spectrometry, the structures of these acidic glycosphingolipids, named F-9 and FGL-I, were determined to be: [3,4-O-(S-1-carboxyethylidene)]Gal beta1 --> 3GalNAc alpha1 --> 3[6'-O-(2-aminoethylphosphonyl)Gal alpha1-2](2-aminoethylphosphoryl --> 6)Gal beta1 --> 4Glc beta1 --> 1ceramide and [3,4-O-(S-1-carboxyethylidene)] Gal beta1-3GalNAc alpha1 --> 3(Fuc alpha1 --> 2)(2-aminoethylphosphoryl --> 6)Gal beta1 --> 4Glc beta1 --> 1ceramide, respectively. Their major aliphatic components are palmitic acid, octadeca-4-sphingenine and anteisononadeca-4-sphingenine. Thus, pyruvylated glycosphingolipids containing phosphoethanolamine in addition to or in place of 2-aminoethylphosphonate are present in the nervous system of Aplysia.