Polar glycosphingolipids in insect: chemical structures of glycosphingolipid series containing 2'-aminoethylphosphoryl-(----6)-N-acetylglucosamine as a polar group from larvae of the green-bottle fly, Lucilia caesar.
A series of glycosphingolipids containing 2'-aminoethylphosphoryl(----6)-N-acetylglucosamine as a polar group has been demonstrated in larvae of the green-bottle fly, Lucilia caesar. The thin-layer chromatographic pattern of the total polar glycolipid revealed the presence of more than eight components, of which five major components were purified by the use of successive column chromatography on QAE- and DEAE-Sephadex and silicic acid (Iatrobeads). From structural studies including compositional sugar analysis, hydrogen fluoride degradation, proton magnetic resonance spectroscopy, methylation analysis, and fast atom bombardment mass spectrometry, their structures were deduced to be as follows: 2'-aminoethylphosphoryl----6GlcNAc beta 1-3Man beta 1-4Glc beta 1-Cer, GalNAc beta 1-4(2'-aminoethylphosphoryl----6)GlcNAc beta 1-3Man beta 1-4Glc beta 1-Cer, GalNAc alpha 1-4GalNAc beta 1-4(2'-aminoethylphosphoryl----6)GlcNAc beta 1-3Man beta 1-4Glc beta 1-Cer, Gal beta 1-3GalNAc alpha 1-4GalNAc-beta 1-4(2'-aminoethylphosphoryl----6)GlcNAc beta 1-3Man beta 1-4Glc beta 1-Cer, and GlcNAc beta 1-3Gal-beta 1-3GalNAc alpha 1-4GalNAc beta 1-4 (2'-aminoethylphosphoryl----6)GlcNAc beta 1-3Man beta 1-4Glc-beta 1-Cer. The main molecular species of the ceramide moiety was arachidinyltetradecasphingenine in all of the major glycolipids.
Itonori
S
S
Department of Chemistry, Faculty of Liberal Arts and Education, Shiga University.
Nishizawa
M
M
Suzuki
M
M
Inagaki
F
F
Hori
T
T
Sugita
M
M
D000117:Acetylglucosamine / Q000031:analogs & derivatives* / Q000032:analysis; D000818:Animals; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D002849:Chromatography, Gas; D002855:Chromatography, Thin Layer; D004175:Diptera / Q000737:chemistry*; D006017:Glycolipids / Q000302:isolation & purification; D006028:Glycosphingolipids / Q000737:chemistry* / Q000302:isolation & purification; D007202:Indicators and Reagents; D007814:Larva; D008745:Methylation; D008969:Molecular Sequence Data; D009943:Organophosphorus Compounds / Q000032:analysis*; D016339:Spectrometry, Mass, Fast Atom Bombardment
D006017:Glycolipids; D006028:Glycosphingolipids; D007202:Indicators and Reagents; D009943:Organophosphorus Compounds; C072661:2'-aminoethylphosphoryl(-6)-N-acetylglucosamine; D000117:Acetylglucosamine