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Journal of Lipid Research, Vol. 44, 2073-2088, November 2003
Copyright © 2003 by American Society for Biochemistry and Molecular Biology

Glycosphingolipids of the model fungus Aspergillus nidulans

: characterization of GIPCs with oligo--mannose-type glycans

Beau Bennion^*, Chaeho Park, Matthew Fuller^1,, Rebecca Lindsey, Michelle Momany, Richard Jennemann^** and Steven B. Levery^2,*

^* Department of Chemistry, University of New Hampshire, Durham, NH 03824-3598
The Complex Carbohydrate Research Center and Department of Biochemistry and Molecular Biology, University of Georgia, Athens, GA 30602-7229
Department of Plant Biology, University of Georgia, Athens, GA 30602-7229
^** Abteilung für Zelluläre und Molekuläre Pathologie, Deutsches Krebsforschungszentrum-Heidelberg, Im Neuenheimer Feld 280, D69120, Heidelberg, Germany

² To whom correspondence should be addressed. e-mail: slevery{at}cisunix.unh.edu

Aspergillus nidulans is a well-established nonpathogenic laboratory model for the opportunistic mycopathogen, A. fumigatus. Some recent studies have focused on possible functional roles of glycosphingolipids (GSLs) in these fungi. It has been demonstrated that biosynthesis of glycosylinositol phosphorylceramides (GIPCs) is required for normal cell cycle progression and polarized growth in A. nidulans (Cheng, J., T.-S. Park, A. S. Fischl, and X. S. Ye. 2001. Mol. Cell Biol. 21: 6198–6209); however, the structures of A. nidulans GIPCs were not addressed in that study, nor were the functional significance of individual structural variants and the downstream steps in their biosynthesis. To initiate such studies, acidic GSL components (designated An-2, -3, and -5) were isolated from A. nidulans and subjected to structural characterization by a combination of one-dimensional (1-D) and 2-D NMR spectroscopy, electrospray ionization-mass spectrometry (ESI-MS), ESI-MS/collision-induced decomposition-MS (MS/CID-MS), ESI-pseudo-[CID-MS]², and gas chromatography-MS methods.

All three were determined to be GIPCs, with mannose as the only monosaccharide present in the headgroup glycans; An-2 and An-3 were identified as di- and trimannosyl inositol phosphorylceramides (IPCs) with the structures Man13Man12Ins1-P-1Cer and Man13(Man16)Man12Ins1-P-1Cer, respectively (where Ins = myo-inositol, P = phosphodiester, and Cer = ceramide). An-5 was partially characterized, and is proposed to be a pentamannosyl IPC, based on the trimannosyl core structure of An-3.

Abbreviations: Cat, cation; CID, collision-induced dissociation; COSY, correlation spectroscopy; ESI, electrospray ionization; GC, gas chromatography; GIPC, glycosylinositol phosphorylceramide; GSL, glycosphingolipid; HPTLC, high-performance thin-layer chromatography; MS, mass spectrometry; TOCSY, total correlation spectroscopy; TOF, time-of-flight

Supplementary key words glycolipid • mass spectrometry • tandem mass spectrometry • collision-induced dissociation • electrospray ionization • NMR spectroscopy • Aspergillus fumigatus

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