Glycosphingolipids in insects

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Abstract
A group of Calliphora vicina pupal glycolipids could be segregated from the neutral glycosphingolipids, according to their two-dimensional TLC migration properties and positive reactions toward ninhydrin and fluorescamine spray reagents. These classified zwitterionic glycolipids were isolated by silica-gel column chromatography and characterized by the presence of a N-acetyl-glucosamine-bound phosphoethanolamine residue. The structural elucidation of the oligosaccharide moieties was performed by the determination of constituent carbohydrates as alditol acetates, linkage analysis by permethylation, exoglycosidase cleavage, fast-atombombardment mass spectrometry and NMR spectroscopy. The dominant fatty acid and sphingoid base species of the ceramide moieties were C20:0 (arachidic acid) and C14:1 (tetradecasphing-4-enine), respectively. The chemical structures of the zwitterionic, biogenetic glycosphingolipid series were determined as: (PEtn-6′)GlcNAc(β1–3)Man(β1–4)GlcβCer; GalNAc(β1–4) (PEtn-6′)GlcNAc(β1–3)Man(β1–4)Glcβ Cer; GalNAc(α1–4)GalNAc(β1–4) (PEtn-6′)GlcNAc (β1–3)Man(β1–4)GlcβCer; Gal(β1–3)GalNAc(β1–4) (PEtn-6′)GlcNAc(β1–3)Man(β1–4)Glcβ Cer; Gal(β1–3)GalNAc(α1–4)GalNAc(β1–4) (PEtn-6′)GlcNAc(β1–3)Man(β1–4)Glcβ Cer; GlcNAc(β1–3)Gal(β1–3)GalNAc(α1–4)GalNAc(β1–4) (PEtn-6′)GlcNAc(β1–3)Man(β1–4)Glcβ Cer.