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Papers In Press, published online ahead of print August 16, 2003
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Department of Chemistry, University of New Hampshire, Durham, NH 03824
Corresponding Author: slevery{at}cisunix.unh.edu
Aspergillus nidulans is a well-established non-pathogenic 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, but the structures of the GIPCs in this fungus have not been determined, nor have the possible functional significance of individual GIPC variants, and the downstream steps in their biosynthesis, been addressed. In order to further our own investigations, acidic glycosphingolipid components (designated An-2, -3, and -5) were isolated from A. nidulans and subjected to structural characterization by a combination of 1-D 1H and 2-D 1H-1H and 1H-13C NMR spectroscopy; electrospray ionization mass spectrometry (ESI-MS, -MS/CID-MS, and -pseudo-[CID-MS]2) in a hybrid quadrupole/time-of-flight (ESI-Qq/oa-TOF-MS) instrument; and gas chromatography/mass spectrometry (GC/MS). All three were determined to be GIPCs with mannose as the only monosaccharide present in the headgroup glycans; the major ceramide components were N-2'-hydroxy-tetracosanoyl-(t18:0 and t20:0)-4-hydroxysphinganines (phytosphingosines). An-2 and An-3 were identified as di- and trimannosyl IPCs with the structures Man
Revised on July 29, 2003
Accepted on August 5, 2003
Glycosphingolipids of the model fungus Aspergillus nidulans: characterization of glycosylinositol phosphorylceramides with oligo-
-mannose-type glycans
1-3Man1-2Ins1-P-1Cer and Man1-3(Man1-6)Man1-2Ins1-P-1Cer, respectively (where Ins = myo-inositol, P = phosphodiester). An-5 was partially characterized, and is proposed to be a pentamannosyl IPC based on the trimannosyl core structure of An-3. The results are discussed in relation to GIPC structures already known, to the taxonomic relationship between A. nidulans and other fungal species expressing similar structures, and to the further potential for using A. nidulans as a model for GIPC biosynthesis and function in the opportunistic mycopathogen A. fumigatus
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