Novel Neogala Series Glycosphingolipids with Glucose at the Non-reducing Termini in the Earthworm, Pheretima sp.

Abstract

Three novel neogala series glycosphingolipids each containing one or two glucose residues were isolated and purified from the earthworm, Pheretima sp. Their chemical structures were determined to be Glc α 1-4 Gal β 1-6 Gal β 1-Cer (glucosylneogalabiaosylceramide), Glc α 1-4 Gal β 1-6 Gal β 1-6 Gal β 1-Cer (glucosylneogalatriaosylceramide) and Glc α 1-4 Gal β 1-6 (Glc α 1-4) Gal β 1-6 Gal β 1-Cer (diglucosylneogalatriaosylceramide) based on the results of compositional analysis, methylation analysis, acid hydrolysis, fast atom bombardment mass spectrometry and proton nuclear magnetic resonance analysis. The ceramide components were behenic and lignoceric acids as the major fatty acids, and octadeca-4-sphingenine and its branched homologue as the sphingoid bases.