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Glycobiology Advance Access originally published online on October 30, 2007
Glycobiology 2008 18(1):84-96; doi:10.1093/glycob/cwm122
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© 2007 The Author(s)
This is an Open Access article distributed under the terms of the Creative Commons Attribution Non-Commercial License (http://creativecommons.org/licenses/by-nc/2.0/uk/) which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited.

Glycosylinositolphosphoceramides in Aspergillus Fumigatus

Catherine Simenel2, Bernadette Coddeville3, Muriel Delepierre2, Jean-Paul Latgé4 and Thierry Fontaine1,4

2 Unité de Résonance Magnétique Nucléaire des Biomolécules, CNRS URA 2185 Institut Pasteur, 25 rue du Docteur Roux 75724 Paris cedex 15
3 Unité de Glycobiologie Structurale et Fonctionnelle, UMR 8576 CNRS, Université des Sciences et Technologies de Lille, 59655 Villeneuve d’Ascq cedex
4 Unité des Aspergillus, Institut Pasteur, 25 rue du Docteur Roux 75724 Paris cedex 15, France

1 To whom correspondence should be addressed: e-mail: tfontain{at}pasteur.fr

Received on August 1, 2007; revised on October 23, 2007; accepted on October 23, 2007

Fungal glycosylinositolphosphoceramides (GIPCs) are involved in cell growth and fungal–host interactions. In this study, six GIPCs from the mycelium of the human pathogen Aspergillus fumigatus were purified and characterized using Q-TOF mass spectrometry and 1H, 13C, and 31P NMR. All structures have the same inositolphosphoceramide moiety with the presence of a C18:0-phytosphingosine conjugated to a 2-hydroxylated saturated fatty acid (2-hydroxy-lignoceric acid). The carbohydrate moiety defines two types of GIPC. The first, a mannosylated zwitterionic glycosphingolipid contains a glucosamine residue linked in {alpha}1-2 to an inositol ring that has been described in only two other fungal pathogens. The second type of GIPC presents an {alpha}-Manp-(1->3)-{alpha}-Manp-(1->2)-IPC common core. A galactofuranose residue is found in four GIPC structures, mainly at the terminal position via a β1-2 linkage. Interestingly, this galactofuranose residue could be substituted by a choline–phosphate group, as observed only in the GIPC of Acremonium sp., a plant pathogen.

Key words: Aspergillus fumigatus / galactofuranose / glycosphingolipid / glycosylinositolphosphoceramide / NMR


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