Sphingolipids of the mycopathogen Sporothrix schenckii: identification of a glycosylinositol phosphorylceramide with novel core GlcNH2α1→2Ins motif

FEBS Letters

Toledo, Marcos S.²  Levery, Steven B.¹  Takahashi, Helio K.²  Straus, Anita H.² 

[1] Department of Biochemistry and Molecular Biology, and The Complex Carbohydrate Research Center, University of Georgia, 220 Riverbend Road, Athens, GA 30602, USA;Department of Biochemistry, Universidade Federal de São Paulo/Escola Paulista de Medicina, Rua Botucatu 862, 04023-900 São Paulo, SP, Brazil

关键词: Sphingolipid;    Glycolipid;    Dimorphism;    Mycopathogen;    Nuclear magnetic resonance;    Mass spectrometry;    NMR;    nuclear magnetic resonance;    COSY;    correlation spectroscopy;    TOCSY;    total correlation spectroscopy;    NOESY;    nuclear Overhauser effect spectroscopy;    HPLC;    high performance liquid chromatography;    HPTLC;    high performance thin layer chromatography;    GC;    gas chromatography;    ESI;    electrospray ionization;    MS;    mass spectrometry;    CID;    collision-induced decomposition;    DMSO;    dimethyl sulfoxide;    TMS;    trimethylsilyl;    FAME;    fatty acid methyl ester;   

DOI  :  10.1016/S0014-5793(01)02275-X

学科分类：生物化学/生物物理

来源: John Wiley & Sons Ltd.

【 摘 要 】

Acidic glycosphingolipid components were extracted from the yeast form of the dimorphic mycopathogen Sporothrix schenckii. Two minor and the major fraction from the yeast form (Ss-Y1, -Y2, and -Y6, respectively) have been isolated. By a combination of 1- and 2-D ¹H-nuclear magnetic resonance (NMR) spectroscopy, electrospray ionization mass spectrometry (ESI-MS), and gas chromatography/mass spectrometry (GC/MS), Ss-Y6 was determined to be triglycosylinositol phosphorylceramide with a novel glycan structure, Manα1→3Manα1→6GlcNH₂α1→2Ins1-P-1Cer (where Ins=myo-inositol, P=phosphodiester). While the GlcNH₂α1→ 6 Ins1-P- motif is found widely distributed in eukaryotic GPI anchors, the linkage GlcNH₂α1→ 2 Ins1-P- has not been previously observed in any glycolipid. Ss-Y1 and Ss-Y2 were both found to have the known glycan structure Manα1→3Manα1→2Ins1-P-1Cer. Together with the results of a prior study [Toledo et al. (2001) Biochem. Biophys. Res. Commun. 280, 19–24] which showed that the mycelium form expresses GIPCs with the structures Manα1→6Ins1-P-1Cer and Manα1→3Manα1→6Ins1-P-1Cer, these results demonstrate that S. schenckii can synthesize glycosylinositol phosphorylceramides with at least three different core linkages.

【 授权许可】

Unknown