A novel fucosylated glycosphingolipid with a Gal beta 1-4Glc beta 1-3Gal sequence in plerocercoids of the parasite, Spirometra erinacei.

A novel glycosphingolipid (SEGLx) has been isolated from the plerocercoids of a tapeworm, Spirometra erinacei. From the results of compositional analysis, methylation analysis, exoglycosidase hydrolysis, acid hydrolysis, fast atom bombardment mass spectrometry, and proton nuclear magnetic resonance (NMR) analysis, its structure was concluded to be [formula: see text] This is the first report of a glycosphingolipid with a novel carbohydrate structure which is characterized by i) the occurrence of a penultimate glucose molecule attached to the reducing end galactose through a beta 1-3 linkage and ii) the presence of a fucose attached to a glucose through an alpha 1-3 linkage. The ceramide contained sphinganine or 4-D-hydroxy-sphinganine, and either a nonhydroxy fatty acid with 16, 18, 26, or 28 carbon atoms, or hydroxystearic acid. Proton NMR analysis revealed that the chemical species of both the long chain base and fatty acid moieties affect the chemical shifts of the anomeric proton resonances of not only the reducing terminal galactose but also the penultimate glucose.