Isolation and characterization of glucosylsphingosine from Gaucher's spleen.
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.
D000215:Acylation; D000328:Adult; D001344:Autopsy; D002518:Ceramides; D002554:Cerebrosides; D055598:Chemical Phenomena; D002621:Chemistry; D002849:Chromatography, Gas; D002852:Chromatography, Ion Exchange; D002855:Chromatography, Thin Layer; D005776:Gaucher Disease / Q000378:metabolism*; D005947:Glucose; D006026:Glycoside Hydrolases; D006027:Glycosides / Q000032:analysis / Q000302:isolation & purification*; D006801:Humans; D006868:Hydrolysis; D013058:Mass Spectrometry; D010169:Palmitic Acids; D011609:Psychosine / Q000031:analogs & derivatives; D013110:Sphingosine / Q000031:analogs & derivatives* / Q000302:isolation & purification; D013154:Spleen / Q000032:analysis*
D002518:Ceramides; D002554:Cerebrosides; D006027:Glycosides; D010169:Palmitic Acids; D011609:Psychosine; C035742:sphingosyl beta-glucoside; D006026:Glycoside Hydrolases; D005947:Glucose; D013110:Sphingosine