A novel sphingophosphonoglycolipid containing 3-O-methylgalactose isolated from the skin of the marine gastropod Aplysia kurodai.
A novel sphingophosphonolipid was isolated from the skin of a marine gastropod, Aplysia kurodai. It was composed of one mol each of sphingosine base, fatty acid, glucose, galactosamine, and an unknown sugar and two mol each of galactose and aminophosphonic acid. The unknown sugar was identified as 3-O-methylgalactose by GC-mass spectrometry of the alditol acetate derivative and by GLC of the trimethylsilyl methylglycoside derivative. The aminophosphonic acid was identified as 2-aminoethylphosphonic acid by TLC of the free acid and the dinitrophenyl (DNP-) compound and by GLC of the O-di-trimethylsilyl-N-isothiocyanate compound. Thus, a ceramide bis(2-aminoethylphosphono)-pentaoside structure having an oligosaccharide chain consisting of one mol each of glucose, 3-O-methylgalactose and galactosamine and two mol of galactose was proposed.
D000615:Aminoethylphosphonic Acid / Q000302:isolation & purification; D000818:Animals; D001048:Aplysia / Q000378:metabolism*; D002241:Carbohydrates / Q000032:analysis; D002849:Chromatography, Gas; D002855:Chromatography, Thin Layer; D005227:Fatty Acids / Q000032:analysis; D006028:Glycosphingolipids / Q000302:isolation & purification*; D008756:Methylgalactosides / Q000032:analysis*; D008759:Methylglycosides / Q000032:analysis*; D012867:Skin / Q000032:analysis
D002241:Carbohydrates; D005227:Fatty Acids; D006028:Glycosphingolipids; D008756:Methylgalactosides; D008759:Methylglycosides; D000615:Aminoethylphosphonic Acid