Characterization of a Novel Triphosphonooctaosylceramide from the Eggs of the Sea Hare, Aplysia kurodail

Abstract

We have reported the existence of a triphosphonoglycosphingolipid, EGL-I, in the eggs of a sea gastropod, Aplysia kurodai [Yamada, S., Araki, S., Abe, S., Kon, K., Ando, S., and Satake, M. (1995) J. Biochem. 117, 794-799]. We have now isolated a novel glycosphingolipid, named EGL-II, from the eggs of Aplysia. By component analysis, sugar analysis, permethylation studies, fast atom bombardment-mass spectrometry, secondary ion mass spectrometry, and proton magnetic resonance spectrometry, its structure was revealed to be as follows: Galα1→3 (GlcNAcα1→2) Galα1→3 (3-O-MeGalα1→2) Galα1→3[6'-O-(2-aminoethylphosphonyl) Galα1→2] (2-aminoethylphosphonyl→6) Galβ1→4 (2-aminoethylphosphony1→6) Glcβ1→1ceramide. The major aliphatic components of the ceramide are pahnitic acid, stearic acid, and anteisononadeca-4-sphingenine.