Structural Analysis of a Novel Triphosphonoglycosphingolipid from the Egg of the Sea Hare, Aplysia kurodai

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A novel phosphonoglycosphingolipid which contains three residues of 2-aminoethylphos-phonate (2-AEP) was isolated from eggs of a sea gastropod, Aplysia kurodai, and its structure was identified as follows.
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The major aliphatic components of ceramide were palmitic acid, stearic acid, 4-sphingenine, and 16-methyl-4-sphingenine. Antibodies which recognize 3-O-methylgalactose linked β-glycosidically to phosphonoglycosphingolipids failed to react to the egg glycolipid. By comparing ¹H-NMR spectra of native and HF-treated glycolipids, steric interactions of two residues of 2-AEP with ring protons of the glucose and the internal galactose were indicated.