Isolation and Characterization of a Novel 2-Aininoethyiphosphonyl-glycosphingolipid from the Sea Hare, Aplysia kurodai1

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Abstract
A novel phosphonoglycosphingolipid named SGL-I' containing 1 mol of 2-amino-ethylphosphonate residue was isolated from the skin of Aplysia kurodai using two siicic acid chromatography systems. Data obtained on methanolysis, permethyla tion, mild acid hydrolysis, and hydrogen fluoride treatment combined with thin-layer chromatography, gas liquid chromatography, gas chromatography-mass spectrom etry, and proton magnetic resonance spectrometry showed that this glycolipid was 3-O-MeGalβ1→3GalNAcal→3[6′-O-(2-aminoethylphosphonyl)Galal → 2] Galβ1→4Glcβ1 1Ceramide. Palmitic acid, octadeca-4-sphingenine and anteiso-nonadeca 4-sphingenine are its major aliphatic components. The new glycolipid has essen tially the same structure as another major phosphonoglycosphingolipid in the skin of Aplysia, SGL-II, that contains 2 mol of 2-aminoethylphosphonate residue, suggesting a metabolic relationship between the two.