Acidic Glycosphingolipids in Brackish Water Annelida

The acidic glycolipid fraction from whole tissues of the lugworm, Tylorrhynchus heterochetus that inhabits brackish water was resolved into more than seven components each showing positive reaction toward molybdate (phosphate) and/or orcinol-sulfuric acid (sugar) spray reagents on thin-layer chromatography. Two major components (AGL4 and AGL5) were isolated and purified by successive column chromatography on ion exchange-Sephadex (DEAF-Sephadex) and porous silica gel (Iatrobeads). Their structures were determined by ompositional sugar analysis, hydrogen fluoride degradation, methylation analysis, periodate oxidation, gas chromatography-mass spectrometry, proton magnetic resonance spectroscopy, fast atom bombardment mass spectrometry and matrix-assisted laser desorption ionization time-of-flight mass spectrometry. The chemical structures were characterized as : Man (α1-2) Ins (1→) -P-Cer for AGL4 and Man (α1-2) [Fuc (α1-5)] Ins (1→) -P-Cer for AGL5, respectively. Aliphatic constituents of both lipids were primarily palmitic and stearic acids, and C18-sphingoids, octadecasphinganine and octadeca-4-sphingenine.