title: Structure determination of glucosyl beta 1-N-(omega-O-linoleoyl)-acylsphingosines of human epidermis.
abstract: Human epidermis gave two glycolipid bands that migrated faster than glucosylceramide and two bands that migrated like glucosylceramide and galactosylceramide, respectively, on TLC. The two faster migrating glycolipids (GL-I and GL-II), which exhibited alkalilability, were purified by conventional DEAE and silica gel column chromatographies, and further by HPLC on a silica gel column. Structure determination of the two components, named GL-I3 and GL-II3, which were finally purified from GL-I and GL-II, respectively, by HPLC on a reversed phase column, was performed by means of 1H-NMR spectroscopy, fast atom bombardment mass spectrometry, and component analysis involving GLC-mass spectrometry. GL-I3 was determined to be a mixture of glucosyl beta 1-N-(omega-O-linoleoyl)-triacontanoyl- and -dotriacontamonoenoyl-eicosasphingenine, and one of the two components of GL-II3 was determined to be glucosyl beta 1-N-(omega-O-linoleoyl)triacontanoyl-trihydroxyeicosasphingenin e. GL-I3 and GL-II3 were the major components of GL-I and GL-II, respectively, and both the latter contained additional four components, which were heterogeneous as to the ceramide portion. This paper reports the structures of acylglucosylceramides isolated from human epidermis together with 1H-NMR spectra and mass spectra demonstrating their molecular weights. The structure of molecular species containing trihydroxysphingosine having a double bond is novel.
authors.affiliation: Department of Dermatology, Yamaguchi University School of Medicine.
authors.forename: S
authors.initials: S
authors.lastname: Hamanaka
authors.forename: C
authors.initials: C
authors.lastname: Asagami
authors.forename: M
authors.initials: M
authors.lastname: Suzuki
authors.forename: F
authors.initials: F
authors.lastname: Inagaki
authors.forename: A
authors.initials: A
authors.lastname: Suzuki
mesh_terms: D000293:Adolescent; D000328:Adult; D000368:Aged; D000369:Aged, 80 and over; D002241:Carbohydrates / Q000032:analysis / Q000302:isolation & purification; D002554:Cerebrosides / Q000032:analysis*; D002849:Chromatography, Gas; D002851:Chromatography, High Pressure Liquid; D002855:Chromatography, Thin Layer; D004817:Epidermis / Q000032:analysis*; D005260:Female; D006017:Glycolipids / Q000032:analysis / Q000302:isolation & purification; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D013058:Mass Spectrometry; D008875:Middle Aged; D008970:Molecular Weight; D013056:Spectrophotometry, Ultraviolet
chemical_list: D002241:Carbohydrates; D002554:Cerebrosides; D006017:Glycolipids