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Volume 271, Number 44, Issue of November 1, 1996 pp. 27353-27359
©1996 by The American Society for Biochemistry and Molecular Biology, Inc.

Biosynthesis of the Trichothecene 3-Acetyldeoxynivalenol
IS ISOTRICHODERMIN A BIOSYNTHETIC PRECURSOR?

(Received for publication, June 5, 1996, and in revised form, August 8, 1996)

Lolita O. Zamir Dagger § , Anastasia Nikolakakis Dagger , Kenneth A. Devor Dagger and Françoise Sauriol §

From the Dagger  Centre de Recherche en Microbiologie Appliquée, Université du Québec, Institut Armand-Frappier, 531 Boulevard des Prairies, Laval, Québec, Canada H7V 1B7, the § Department of Chemistry, McGill University, 801 Sherbrooke Street West, Montreal, Quebec, H3Z 2K6, Canada

3-Acetyldeoxynivalenol is the major trichothecene produced by the fungus Fusarium culmorum. The first proven tricyclic intermediate in the biosynthesis of 3-acetyldeoxynivalenol has been shown by in vivo studies to be isotrichodermin, a natural metabolite of F. culmorum. Indeed, the feeding of ring-deuterated isotrichodermin resulted in ring-deuterated 3-acetyldeoxynivalenol as shown by NMR studies.

In this work, we have shown that the 3-acetyl group of isotrichodermin is mostly lost in its metabolism to 3-acetyldeoxynivalenol. We have shown by two different approaches that the deacetylation occurs at an early step after the first oxygenation step at C-15. Derivatives of isotrichodermin lacking the 3-acetyl such as 3-deacetyl isotrichodermin or 3-oxo-12,13-epoxytrichothec-9-ene are not precursors to 3-acetyldeoxynivalenol. The role of this acetyl exchange mechanism is not clear presently.


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Copyright © 1996 by the American Society for Biochemistry and Molecular Biology.