Structure of a novel diphosphonoglycosphingolipid isolated from the skin of Aplysia kurodai.
A new phosphonoglycosphingolipid containing two 2-aminoethylphosphonate residues was isolated from the skin of Aplysia kurodai, a marine gastropod, using two systems of silicic acid chromatography. By methanolysis, permethylation, mild acid hydrolysis and hydrogen fluoride treatment combined with thin layer chromatography and gas chromatography-mass spectrometry, the new phosphonoglycosphingolipid was shown to be 3-O-MeGal (1----3) GalNAc (1----3) [6'-O-(2-aminoethylphosphonyl) Gal (1----2)] [2-aminoethylphosphonyl (----6)] Gal (1----4) Glc (1----1) ceramide. Most of the fatty acid (90 per cent) was palmitic acid. Octadeca-4-sphingenine and anteiso-nonadeca-4-sphingenine were the major sphingosine bases of the new glycolipid.
D000615:Aminoethylphosphonic Acid / Q000032:analysis; D000818:Animals; D001048:Aplysia / Q000032:analysis*; D006017:Glycolipids / Q000032:analysis*; D006028:Glycosphingolipids / Q000032:analysis*; D013058:Mass Spectrometry; D063065:Organophosphonates / Q000032:analysis; D012867:Skin / Q000032:analysis
D006017:Glycolipids; D006028:Glycosphingolipids; D063065:Organophosphonates; C029666:ceramide bis(2-aminoethylphosphono)pentaoside; D000615:Aminoethylphosphonic Acid