Structural elucidation of a novel phosphonoglycosphingolipid in eggs of the sea hare Aplysia juliana.
A novel phosphonoglycosphingolipid (AJPnGL) was isolated from eggs of the sea hare Aplysia juliana. The structure was determined to be Gal alpha 1-->2Gal beta 1-->4(2-aminoethylphosphonyl-->6)Glc beta 1-->1Cer by FAB/MS, 1H-NMR, hydrogen fluoride degradation, methylation analysis, partial acid hydrolysis and GC analysis of the component sugars, fatty acids and long-chain bases. The ceramide moiety of this lipid consisted of branched nonadeca-4-sphingenine and octadeca-4-sphingenine as main long-chain bases and palmitic acid and stearic acid as major fatty acids. Since the sugar chain (Gal alpha 1-->2Gal beta 1-->4Glc beta 1-->) and the ceramide moiety of AJPnGL were identical with those of the main neutral glycosphingolipid of eggs of A. juliana, the biosynthesis of AJPnGL may occur by the addition of 2-aminoethylphosphonate to the main neutral glycosphingolipid, Gal alpha 1-->2Gal beta 1-->4Glc beta 1-->1Cer.
Yamaguchi
Y
Y
Department of Chemistry, Faculty of Science and Technology, Kinki University, Osaka, Japan.
Ohta
M
M
Hayashi
A
A
D000818:Animals; D001048:Aplysia / Q000737:chemistry*; D002240:Carbohydrate Sequence; D002241:Carbohydrates / Q000032:analysis; D002518:Ceramides / Q000032:analysis; D006028:Glycosphingolipids / Q000737:chemistry*; D006868:Hydrolysis; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D010063:Ovum; D010766:Phosphorylation; D016339:Spectrometry, Mass, Fast Atom Bombardment
D002241:Carbohydrates; D002518:Ceramides; D006028:Glycosphingolipids