Structure elucidation of sphingolipids from the mycopathogen Sporothrix schenckii: Identification of novel glycosylinositol phosphorylceramides with core Man alpha 1 -> 6Ins linkage

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2001-01-12
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Toledo, M. S.
Levery, S. B.
Glushka, J.
Straus, A. H.
Takahashi, H. K.
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Acidic glycosphingolipid components were extracted from the mycelium form of the thermally dimorphic mycopathogen Sporothrix schenckii. Two fractions from the mycelium form (Ss-M1 and Ss-M2), having the highest Rf values on HPTLC analysis, were isolated and their structures elucidated by 1- and 2-D C-13- and H-1-nuclear magnetic resonance spectroscopy, and electrospray ionization mass spectrometry with lithium adduction of molecular ions, the structures of Ss-M1 and Ss-M2 were determined to be Man alpha1-->Ins1-P-1Cer and Man alpha1-->3Man alpha1-->Ins1-P-1Cer, respectively (where Ins = myoinositol, P = phosphodiester). the Man alpha1-->6Ins motif is found normally in diacylglycerol-based glycophosphatidylinositols of Mycobacteria, but this is the first unambiguous identification of the same Linkage making up the core structure of fungal glycosylinositol phosphoryl-ceramides (GIPCs). These results are discussed in relation to the structures of GIPCs of other mycopathogens, including Histoplasma capsulatum and Paracoccidioides brasiliensis. (C) 2001 Academic Press.
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Biochemical and Biophysical Research Communications. San Diego: Academic Press Inc, v. 280, n. 1, p. 19-24, 2001.