Characterization of a novel triphosphonooctaosylceramide from the eggs of the sea hare, Aplysia kurodai

We have reported the existence of a triphosphonoglycosphingolipid, EG;L-I, in the eggs of a sea gastropod, Aplysia kurodai [ Yamada, S,, Araki, S,, Ab e, S,, Ken, K, Ando, S,, and Satake, M. (1995) J, Biochem, 117, 794-799], W e 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, a nd proton magnetic resonance spectrometry, its structure was revealed to be as follows: Gal alpha1-->3(GlcNAc alpha1-->2)Gal alpha1-->3(3-O-MeGa alpha 1-->2)Gal alpha1-->3[6'-O-(2-aminoethylphosphonyl)Gal alpha1-->2] (2-aminoe thylphosphonyl-->6)Gal beta1-->4(2-aminoethylphosphonyl-->6)Glc beta1-->1ce ramide. The major aliphatic components of the ceramide are palmitic acid, s tearic acid, and anteisononadeca-4-sphingenine.