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Glycobiology Advance Access published online on January 22, 2007
Glycobiology, doi:10.1093/glycob/cwm006
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© The Author 2007. Published by Oxford University Press. All rights reserved. For permissions, please e-mail: journals.permissions@oxfordjournals.org

Purification and structural characterization of the de-N-acetylated form of GD3 ganglioside present in human melanoma tumors

Iuliana Popa1,5, Alexandre Pons2, Christophe Mariller2, Tadashi Tai3, Jean-Pierre Zanetta2, Luc Thomas4 and Jacques Portoukalian1,*

1 Laboratory of Dermatological Research, University of Lyon-1 and Edouard Herriot Hospital, 69437 Lyon Cx 03, France
2 Laboratory of Biological Chemistry, CNRS UMR 8576, USTL, 59655 Villeneuve d'Ascq Cx, France
3 Department of Tumor Immunology, The Tokyo Metropolitan Institute of Medical Science, Honkomagome, Bunkyo-ku, Tokyo 113, Japan
4 Department of Dermatology, Hotel-Dieu Hospital, Lyon, France
5 Institute of Macromolecular Chemistry Petru Poni, Aleea Gr. Ghica Voda 41A, Iassy 6600, Romania

* Author to whom correspondence, proof and reprints should be addressed Phone +33-4 72 11 03 07, Fax +33-4 72 11 02 90; e-mail portoukalian{at}lyon.inserm.fr

Received on May 6, 2006; revised on December 22, 2006; accepted on January 11, 2007

The presence in human tissues of gangliosides containing de-N-acetylated sialic acids has been so far shown by using mouse monoclonal antibodies specific for the de-N-acetylated forms, but the isolation and chemical characterization of such compounds have not yet been performed. Since indirect evidence suggested that de-N-acetylGD3 ganglioside could be present in human melanoma tumors, we analyzed the gangliosides purified from a 500 g pool of those tumors. De-N-acetylGD3 that was found to migrate just below GD2 by thin-layer chromatography was isolated by HPLC from the disialogangliosides using the specific antibody to monitor the elution. The amount of antigen was found to be of 320 ng per gram of fresh tumor. Gas chromatography-mass spectrometry analysis of the antibody-positive ganglioside showed that the sialic acids were formed of one molecule of N-acetylneuraminic acid (Neu5Ac) and one of neuraminic acid. Radioactive re-N-acetylation of the antigen yielded a GD3-like ganglioside with the radioactive label on the external sialic acid. The constitutive fatty acids were found to differ markedly from those of GD3 and 9-O-acetylGD3 isolated from the same pool of tumors. The major fatty acids were C16:0 and C18:0 in de-N-acetylGD3 whereas GD3 and its 9-O-acetylated derivative contained a large amount of C24:1. These data show that de-N-acetylGD3 ganglioside is indeed present in human melanoma tumors and the fatty acid content suggests the existence of a de-N-acetylase mostly active on molecular species of gangliosides with short chain fatty acids.

Key words: melanoma / gangliosides / GD3 / de-N-acetylation / mass spectrometry


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