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Volume 17, Issue 4, Pages 725-734

New chaetoglobosins from maize infested by Phomopsis leptostromiformis fungi. Production, identification, and semi‒synthesis

Ludovic Burlot,1 Jean-Claude Cherton,1 Odile Convert,2 Isabelle Correia,2 and Bruno Dennetiere3

1Laboratoire SIRCOB, Département de Chimie, Université de Versailles Saint-Quentin en Yvelines, 45 avenue des Etats-Unis, 78035 Versailles, France
2Université Pierre et Marie Curie, 4 place Jussieu, boite 45, 75252 Paris, Cedex 05, France
3Laboratoire de Cryptogamie, Muséum National d’Histoire Naturelle, 12 rue Buffon, 75005, Paris, France

Copyright © 2003 Hindawi Publishing Corporation. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.


This paper deals with the cytotoxic chaetoglobosins obtained from culture on maize of the strains ATCC 26115 and MRC 2654 of the fungus Phomopsis leptostromiformis Both strains produced, in more or less important amounts, the known chaetoglobosins M (1) and N (2). In addition, the new chaetoglobosin O (3), was isolated from the ATCC 26115 strain and characterized by HRMS and 2D NMR experiments. With the MRC 2654 strain, a fungal metabolite 4, more polar than the chaetoglobosins M and N, was extracted and purified. Spectroscopic and chromatographic data of metabolite 4 led to its identification to the bridged chaetoglobosin named compound S, which previously has been obtained by intramolecular Michael reaction on the chaetoglobosin M. Moreover, a methylation under Williamson conditions of the chaetoglobosin 4 resulted in the formation of the trimethylated chaetoglobosin 5.