Characterization of a diphosphonopentaosylceramide containing 3-O-methylgalactose from the skin of Aplysia kurodai (sea hare)
The complete structure is proposed for a ceramide (Cer), bis(2-aminoethylphosphono)-pentaoside, isolated from the skin of Aplysia kurodai. This new phosphonoglycosphingolipid was purified using two systems of column chromatography on silicic acid. The purity of the glycolipid was confirmed by thin-layer chromatography, analysis of its composition, and proton magnetic resonance spectrometry. The component carbohydrates were glucose, galactose, N-acetylgalactosamine, and 3-O-methylgalactose. Most (90%) of the fatty acid was palmitic acid and the major sphingosine bases were octadeca-4-sphingenine (51%) and anteisononadeca-4-sphingenine (38%). 2-Aminoethylphosphonyl-6-galactose was identified after its partial hydrolysis. From studies by methanolysis, permethylation, mild acid hydrolysis, hydrogen fluoride treatment, chromium trioxide oxidation combined with thin-layer chromatography, gas liquid chromatography, gas chromatography-mass spectrometry, and proton magnetic resonance spectrometry, the structure of the glycolipid was concluded to be 3-OMeGal beta 1----3GalNAc alpha 1----3[6'-O-(2-aminoethylphosphonyl)-Gal alpha 1----2](2-aminoethylphosphonyl----6)Gal beta 1----4Glc beta 1----1Cer.
D000818:Animals; D001048:Aplysia / Q000032:analysis*; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D002241:Carbohydrates / Q000032:analysis; D002518:Ceramides / Q000032:analysis*; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D002845:Chromatography; D005227:Fatty Acids / Q000032:analysis; D008401:Gas Chromatography-Mass Spectrometry; D006017:Glycolipids / Q000032:analysis*; D006028:Glycosphingolipids; D009682:Magnetic Resonance Spectroscopy; D008756:Methylgalactosides / Q000032:analysis*; D008759:Methylglycosides / Q000032:analysis*; D010084:Oxidation-Reduction; D012867:Skin / Q000032:analysis*; D013110:Sphingosine / Q000032:analysis
D002241:Carbohydrates; D002518:Ceramides; D005227:Fatty Acids; D006017:Glycolipids; D006028:Glycosphingolipids; D008756:Methylgalactosides; D008759:Methylglycosides; C048494:diphosphonopentaosylceramide; D013110:Sphingosine