Neutral and Amphoteric Glycosphingolipids from Annelida (Lugworm, Tylorhynchus heterochaetus)

Gal β 1-Cer (CMS3) and cholinephosphoryl→6 Gal β 1-Cer (PGL) were found as the main neutral and amphoteric glycosphingolipids from the whole tissue of the lugworm, Tylorhynchus heterochaetus. These lipids were purified by successive column chromatography on DEAE- and QAE-Sephadex A-25, Florisil and silicic acid (Iatrobeads), and identified by gas-liquid chromatography, methylation analysis, enzymatic hydrolysis, chromium trioxide oxidation, hydrogen fluoride degradation and positive-ion fast atom bombardment mass spectrometry.The ceramide moieties of both glycolipids were virtually the same : fatty acids were saturated C16-, C17- and C18-acids ; sphingoids were octadeca-4-sphingenine and octadeca-4, 8-sphingadienine. The structural similarity of the ceramide moieties suggests PGL biosynthesis from CMS3.In addition, their thin-layer chromatographic behaviors and the results of sugar analysis suggest that the structures of at least three minor components of the ceramide mono-, di- and trisaccharide fractions are Glc-Cer, Man-Gal-Cer and Man-Gal-Gal-Cer, respectively.