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Journal of Lipid Research, Vol. 43, 794-804, May 2002
Copyright © 2002 by Lipid Research, Inc.

Methods

Gas-chromatography/mass-spectrometry analysis of human skin constituents as heptafluorobutyrate derivatives with special reference to long-chain bases

Alexandre Pons, Philippe Timmerman, Yves Leroy and Jean-Pierre Zanetta¹

CNRS Unité Mixte de Recherche 8576, Glycobiologie Structurale et Fonctionnelle, Laboratoire de Chimie Biologique Université des Sciences et Technologies de Lille, 59655 Villeneuve d'Ascq cedex, France

¹ To whom correspondence should be addressed. e-mail: jean-pierre.zanetta{at}univ-lille1.fr

Manuscript received 5 June 2001, in revised form 28 September 2001, and in re-revised form 22 January 2002.

The composition of the constituents (monosaccharides, long-chain bases, and fatty acids) found in an ethanol extract of the human skin could be determined, without time-consuming steps of purification, after acid-catalyzed anhydrous methanolysis, followed by the formation of volatile derivatives with heptafluorobutyric anhydride and gas-chromatography/mass-spectrometry analysis. Despite the extreme heterogeneity of such extracts, the electron impact analysis of the constituents allowed qualitative and quantitative determinations of monosaccharides, long-chain bases, fatty acids, and alkyl-glycerols. Throughout the different long-chain bases, sphingenines (Sphes), sphinganines, phytosphingosines, and 6-hydroxy-Sphes (6oh-Sphes) can be identified and quantified. Long-chain bases with a chain-length up to 28 carbon atoms can be identified through specific fragmentation patterns in the electron impact mode. Particular attention was drawn to the behavior of compounds of the family of 6oh-Sphes upon acid-catalyzed methanolysis.—Pons, A., P. Timmerman, Y. Leroy, and J-P. Zanetta. GC/MS analysis of human skin constituents as heptafluorobutyrate derivatives with special reference to long-chain bases. J. Lipid Res. 2002. 43: 794–804.

Abbreviations: CI, chemical ionization; EI, electron impact; FAME, fatty acid methyl ester; Gal, galactose; GlcNAc, N-acetyl-glucosamine; GalNac, N-acetyl-galactosamine; GC, gas chromatography; HFB, heptafluorobutyrate; HFBAA, heptafluorobutyric anhydride; LCB, long-chain base; Man, mannose; MS, mass spectrometry; Phyt, phytosphingosine; Rt, retention time; Spha, sphinganine; Sphe, sphingenine; TIC, total ion counts

Supplementary key words amino acids • monosaccharides • fatty acid • sphingenine • sphinganine • phytosphingosine • 6-hydroxy-sphingenine

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