Isolation and structural analysis of three neutral glycosphingolipids from a mixed population of Caenorhabditis elegans (Nematoda: Rhabditida)

The free-living nematode, Caenorhabditis elegans, has been proposedand analyzed as a prototypic model for parasitic nematodes.In order to study whether there is a structural basis for theproposed analogy with respect to nematode glycoconjugates, wehave analyzed Caenorhabditis elegans glycosphingolipids. Three,simple neutral glycosphingo-lipid components of the neutralglycolipid fraction were isolated by high-performance liquidchromatography. Structural analysis was performed by methylationanalysis, exoglycosidase cleavage, matrix-assisted laser desorption/ionization time-of-flight mass spectrometry, and ceramide analysis.The chemical structures have been determined as Glcß1Cer,Manß4Glcß1Cer and GlcNAcß3Manp4Glcß1Cer;that are characterized as belonging to the arthro-series ofprotostomial glycosphingolipids. The ceramide moiety of theparent glycosphingolipid-ceramide mono-hexoside was dominatedby 2-hydroxy fatty acids, and a d17:1 sphingoid-base with aniso- or anteiso-branched chain. The chemical composition ofthe three glycosphingolipids from Caenorhabditis elegans displayedclose structural coincidence with the equivalent structuresfrom the porcine parasitic nematode, Ascaris suum (G.Lochnit,R.D. Dennis, U.Zähringer, and R.Geyer, Glycoconjugate J.,1997), in support of this organism as a prototypic glyco-sphingolipidmodel for parasitic nematodes. Arthro-series glycosphingolipids Caenorhabditis elegans d17:1 branched sphingoid-bases MALDI-TOF-MS nematode neutral glycosphingolipids