Isolation and characterization of glucosylsphingosine from Gaucher's spleen

Abstract

Glucosylsphingosine has been isolated for the first time as a natural constituent from Gaucher's spleen. On thin-layer chromatography, it migrates with authentic glucosylsphingosine, yielding a positive color reaction with ninhydrin for the amino group and with alpha-naphthol-sulfuric acid for the carbohydrate residue. N-Acylation with palmitic acid gave rise to glucosylceramide, which was cleaved by purified glucosylceramide: beta-glucosidase to ceramide. Gas-liquid chromatography of the trimethylsilyl derivative showed a retention time similar to authentic glucosylsphingosine. Gas-liquid chromatographic analysis of the trimethylsilyl derivatives after methanolysis revealed the presence of only glucose and C(18)-sphingosine. Mass spectral data further supported the structural identity with glucosylsphingosine.