Characterization of two glucuronic acid-containing glycosphingolipids in larvae of the green-bottle fly, Lucilia caesar.
Two glucuronic acid-containing glycosphingolipids were purified from larvae of the green-bottle fly, Lucilia caesar by DEAE-Sephadex and Iatrobeads column chromatography. Structures of these acidic glycolipids, glycolipids X and Y, were elucidated by means of sugar analysis, permethylation, enzymatic hydrolysis, negative-ion fast atom bombardment mass spectrometry, and NMR studies. Glycolipid X was determined to have the following structure: GlcA beta 1-3Gal beta 1-3GalNAc alpha 1-4 GalNAc beta 1-4 GlcNAc beta 1-3Man beta 1-4Glc beta 1-1 ceramide. The other acidic glycolipid, glycolipid Y contains a phosphoethanolamine residue linked through the 6-hydroxy group of the N-acetyl-glucosamine unit of glycolipid X. The ceramide moieties were composed of saturated fatty acids (16:0-22:0) and tetradeca- and hexadeca-4-sphingenines. Based on the structural similarity of the ceramide moieties it appears likely that glycolipid X is an intermediate from which glycolipid Y is synthesized by addition of a phosphoethanolamine residue.
Department of Chemistry, Faculty of Liberal Arts and Education, Shiga University, Japan.
M
M
Sugita
S
S
Itonori
F
F
Inagaki
T
T
Hori
D000818:Animals; D002236:Carbohydrate Conformation; D002518:Ceramides; D055598:Chemical Phenomena; D002621:Chemistry; D002849:Chromatography, Gas; D002852:Chromatography, Ion Exchange; D004175:Diptera / Q000032:analysis*; D005965:Glucuronates; D020723:Glucuronic Acid; D006028:Glycosphingolipids; D006868:Hydrolysis; D007814:Larva / Q000032:analysis; D009682:Magnetic Resonance Spectroscopy; D013055:Spectrophotometry, Infrared
D002518:Ceramides; D005965:Glucuronates; D006028:Glycosphingolipids; D020723:Glucuronic Acid