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A more recent version of this article appeared on August 1, 2007

Papers In Press, published online ahead of print May 8, 2007
J. Lipid Res., doi:10.1194/jlr.M700149-JLR200
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Submitted on March 28, 2007
Accepted on May 8, 2007

Sphingolipids of the mycopathogen Aspergillus fumigatus: characterization of glycosylinositol phosphorylceramide antigens with Manp(alpha 1-2)Ins and GlcpN(alpha 1-2)Ins core motifs

Marcos S. Toledo, Steven B. Levery, Beau Bennion, Luciana L. Guimaraes, Sherry A. Castle, Rebecca Lindsey, Michelle Momany, Chaeho Park, Anita H. Straus, and Helio K. Takahashi

Department of Chemistry, University of New Hampshire, Durham, NH 03824

Corresponding Author: slevery{at}cisunix.unh.edu

Acidic glycosphingolipid components were extracted from the opportunistic mycopathogen Aspergillus fumigatus and identified as inositol and glycosylinositol phosphorylceramides (IPC and GIPCs). By a combination of NMR spectroscopy, MS, and GC/MS, the structures of six major components were elucidated as Ins-P-Cer (Af-0), Manp(alpha 1-3)Manp(alpha 1-2)Ins-P-Cer (Af-2), Manp(alpha 1-2)Manp(alpha 1-3)Manp(alpha 1-2)Ins-P-Cer (Af-3a), Manp(alpha 1-3)[Galf(beta 1-6)]Manp(alpha 1-2)-Ins-P-Cer (Af-3b), Manp(alpha 1-2)-Manp(alpha 1-3)[Galf(beta 1-6)]Manp(alpha 1-2)Ins-P-Cer (Af-4), and Manp(alpha 1-3)Manp(alpha 1-6)GlcpN(alpha 1-2)Ins-P-Cer (Af-3c) (where Ins = myo-inositol, P = phosphodiester). A minor A. fumigatus GIPC was also identified as the N-acetylated version of Af-3c (Af-3c*), which suggests that formation of the GlcNalpha 1-2Ins linkage may proceed by a two step process, similar to the GlcNalpha 1-6Ins linkage in GPI anchors (transfer of GlcNAc, followed by enzymatic de-N-acetylation). Components Af-3a, Af-3c*, and Af-4 have novel structures. In an overlay immunostaining assay, a murine monoclonal antibody (MEST-1), raised by immunization with P. brasiliensis GIPCs, and previously shown to react with the Galf(beta 1-6) residue in Pb-3, reacted with Af-3b, Af-4, and additional more complex GIPCs from A. fumigatus. Sera of a patient with aspergillosis reacted with GIPCs bearing the branching Galf(beta 1-6) determinant (Af-3b and Af-4), but also reacted with Af-3a and several other more complex GIPCs from A. fumigatus. These results are discussed in relation to pathogenicity and potential approaches to immunodiagnosis of A. fumigatus.


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