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Originally published In Press as doi:10.1074/jbc.M202295200 on July 22, 2002

J. Biol. Chem., Vol. 277, Issue 40, 37260-37271, October 4, 2002
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Candida albicans Phospholipomannan, a New Member of the Fungal Mannose Inositol Phosphoceramide Family*

Pierre-André TrinelDagger , Emmanuel Maes§, Jean-Pierre Zanetta§, Florence Delplace§, Bernadette Coddeville§, Thierry JouaultDagger , Gérard Strecker§, and Daniel PoulainDagger

From the Dagger  Laboratoire de Mycologie Fondamentale et Appliquée, Inserm EPI 9915, Faculté de Médecine, Pôle Recherche, 59037, Lille Cedex, France, and § Laboratoire de Glycobiologie Structurale et Fonctionnelle, CNRS Unité Mixté de Recherche No. 8576, Laboratoire de Chimie Biologique, Université des Sciences et Technologies de Lille, 59655 Villeneuve d'Ascq, France

The pathogenic yeast Candida albicans has the ability to synthesize unique sequences of beta -1,2-oligomannosides that act as adhesins, induce cytokine production, and generate protective antibodies. Depending on the growth conditions, beta -1,2-oligomannosides are associated with different carrier molecules in the cell wall. Structural evidence has been obtained for the presence of these residues in the polysaccharide moiety of the glycolipid, phospholipomannan (PLM). In this study, the refinement of purification techniques led to large quantities of PLM being extracted from Candida albicans cells. A combination of methanolysis, gas chromatography, mass spectrometry, and nuclear magnetic resonance analyses allowed the complete structure of PLM to be deduced. The lipid moiety was shown to consist of a phytoceramide associating a C18/C20 phytosphingosine and C25, C26, or mainly C24 hydroxy fatty acids. The spacer linking the glycan part was identified as a unique structure: -Man-P-Man-Ins-P-. Therefore, in contrast to the major class of membranous glycosphingolipids represented by mannose diinositol phosphoceramide, which is derived from mannose inositol phosphoceramide by the addition of inositol phosphate, PLM seems to be derived from mannose inositol phosphoceramide by the addition of mannose phosphate. In relation to a previous study of the glycan part of the molecule, the assignment of the second phosphorus position leads to the definition of PLM beta -1,2-oligomannosides as unbranched linear structures that may reach up to 19 residues in length. Therefore, PLM appears to be a new type of glycosphingolipid, which is glycosylated extensively through a unique spacer. The conferred hydrophilic properties allow PLM to diffuse into the cell wall in which together with mannan it presents C. albicans beta -1,2-oligomannosides to host cells.

* This work was supported by the "Réseau Infection Fongique" du Ministère Français de l'Education Nationale de la Recherche et de la Technologie (MNERT).The costs of publication of this article were defrayed in part by the payment of page charges. The article must therefore be hereby marked "advertisement" in accordance with 18 U.S.C. Section 1734 solely to indicate this fact.

To whom correspondence should be addressed. Tel.: 33-3-20-62-34-20; Fax: 33-3-20-62-34-16; E-mail: dan_poulain@compuserve.com.

Copyright © 2002 by The American Society for Biochemistry and Molecular Biology, Inc.
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