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 thinlayer chromatography, it migrates with authentic glucosylsphingosine, yielding a positive color reaction with ninhydrin for the amino group and with α-naphthol–sulfuric acid for the carbohydrate residue. N-Acylation with palmitic acid gave rise to glucosylceramide, which was cleaved by purified glucosylceramide: β-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 C18-sphingosine. Mass spectral data further supported the structural identity with glucosylsphingosine.

Keywords

• Gaucher's disease
• thin-layer chromatography
• gas–liquid chromatography
• β-glucosidic linkage