title: Ceramide dihexosides from the spermatozoa of the starfish, Asterias amurensis, consist of gentiobiosyl- cellobiosyl-, and lactosylceramide.
abstract: Ceramide dihexoside was obtained from the spermatozoa of the starfish, Asterias amurensis. Gas-liquid chromatography of the methanolysate to determine the sugar composition of the lipid demonstrated an unequal ratio of glucose and galactose, implying that two or more glycolipids are present. They were separated by thin-layer chromatography on a borate-impregnated plate into two bands. From the results of methylation analysis and chromic acid oxidation, one was determined to be lactosylceramide, while the other was suggested to be a mixture of two diglucosylceramides: gentiobiosylceramide (Glc beta 1-6Glc beta 1-1Cer) and cellobiosylceramide (Glc beta 1-4Glc beta 1-1Cer). The molar ratio of gentiobiosyl-, cellobiosyl-, and lactosylceramide was estimated to be 0.7 : 0.3 : 1.0. Ceramide dihexosides obtained from another batch of the spermatozoa, collected at the same place in a different year, consisted almost exclusively of gentiobiosylceramide as confirmed by proton-nuclear magnetic resonance spectroscopy and fast-atom bombardment mass-spectrometry. The fatty acid compositions of these glycolipids were similar and the main acids were 14h:0, 15h:0, 16h:0, 18h:0, and 24h:1 (constituting more than 80% of the total acids). The long-chain base compositions were qualitatively similar and the major constituents were commonly d18:2, d18:3, d19:3, d22:2, and t22:1. Lactosylceramide was rich in t22:1, while diglucosylceramides were rich in d22:2.
authors: Department of Life Science, Faculty of Science, Tokyo Institute of Technology.
authors: A
authors: A
authors: Irie
authors: H
authors: H
authors: Kubo
authors: F
authors: F
authors: Inagaki
authors: M
authors: M
authors: Hoshi
mesh_terms: D000818:Animals; D015703:Antigens, CD; D001881:Borates; D002475:Cellobiose / Q000737:chemistry; D002840:Chromates / Q000378:metabolism; D002855:Chromatography, Thin Layer; D004187:Disaccharides / Q000737:chemistry; D005690:Galactose / Q000032:analysis; D005947:Glucose / Q000032:analysis; D006028:Glycosphingolipids / Q000737:chemistry*; D006868:Hydrolysis; D007790:Lactosylceramides; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D008745:Methylation; D013094:Spermatozoa / Q000737:chemistry* / Q000187:drug effects; D013215:Starfish; D001616:beta-Galactosidase / Q000494:pharmacology
chemical_list: D015703:Antigens, CD; D001881:Borates; D002840:Chromates; D004187:Disaccharides; D006028:Glycosphingolipids; D007790:Lactosylceramides; C013869:ceramide dihexoside; D002475:Cellobiose; C009744:CDw17 antigen; D001616:beta-Galactosidase; C100052:gentiobiose; D005947:Glucose; C034944:chromic acid; D005690:Galactose