Novel fucosyltetrahexosylceramide in plerocercoids of the parasite Spirometra erinacei

A novel glycosphingolipid, fucosyltetrahexosylceramide, has been isolated from the plerocercoids of a tapeworm, Spirometra erinacei, and characterized by permethylation analysis, sequential degradation with exoglycosidases, fast atom bombardment MS and H-1-NMR. The chemical structure was determined to be as follows. [GRAPHICS] This glycosphingolipid was tentatively designated as GalSEGLx, in which the carbohydrate structure is characterized by an additional galactose molecule attached to the reducing-end galactose of SEGLx [Gal beta-4(Fuc alpha-3)Glc beta-3Gal beta Cer], which was previously determined by us [Kawakami, Y., Nakamura, K., Kojima, H., Suzuki, M., Inagaki, F., Suzuki, A., Sonoki, S., Uchida, A., Murata, Y. & Tamai, Y. (1993) J. Biochem. 114, 677-683], through a beta 1-6 linkage. The ceramide contained sphinganine and 4D-hydroxysphinganine in an about equimolar ratio, and a non-hydroxy fatty acid with carbon atoms ranging from 16 to 28, 26:0, 28:0 and 28:1 being major components. Based on the finding that a novel carbohydrate structure, Gal beta-4Glc beta-3Gal, was commonly found in glycosphingolipids from the parasite, S. erinacei, we here propose the terms, spirometo series, for this core structure series, and spirometosides, for glycosphingolipids having this carbohydrate structure.