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J Biol Chem, Vol. 274, Issue 18, 12269-12277, April 30, 1999

Biosynthesis of 3-Acetyldeoxynivalenol and Sambucinol
IDENTIFICATION OF THE TWO OXYGENATION STEPS AFTER TRICHODIENE

Lolita O. Zamir^§, Anastasia Nikolakakis^§, Liren Huang^§, Patrick St-Pierre^§, Françoise Sauriol, Salvatore Sparace, and Orval Mamer^**

From the ^§ Centre de Recherche en Microbiologie Appliquée, Université du Québec, Institut Armand-Frappier, Laval, Québec H7N 4Z3, Canada, the  Department of Chemistry, McGill University, Montreal, Québec H3Z 2K6, Canada, the  Plant Science Department, McGill University, McDonald Campus, Ste-Anne de Bellevue, Québec H9X 3V9, Canada, and the ^** Biomedical Mass Spectrometry Unit, McGill University, Montreal, Québec H3A 1A3, Canada

The first two oxygenation steps post-trichodiene in the biosyntheses of the trichothecenes 3-acetyldeoxynivalenol and sambucinol were investigated. The plausible intermediates 2-hydroxytrichodiene (2- and 2-) and 12,13-epoxytrichodiene and the dioxygenated compounds 12,13-epoxy-9,10-trichoene-2-ol (2- and 2-) were prepared specifically labeled with stable isotopes. They were then fed separately and/or together to Fusarium culmorum cultures, and the derived trichothecenes were isolated, purified, and analyzed. The stable isotopes enable easy localization of the labels in the products by ²H NMR, ¹³C NMR, and mass spectrometry. We found that 2-hydroxytrichodiene is the first oxygenated step in the biosynthesis of both 3-acetyldeoxynivalenol and sambucinol. The stereoisomer 2-hydroxytrichodiene and 12,13-epoxytrichodiene are not biosynthetic intermediates and have not been isolated as metabolites. We also demonstrated that the dioxygenated 12,13-epoxy-9,10-trichoene-2-ol is a biosynthetic precursor to trichothecenes as had been suggested in a preliminary work. Its stereoisomer was not found in the pathway. A further confirmation of our results was the isolation of both oxygenated trichodiene derivatives 2-hydroxytrichodiene and 12,13-epoxy-9,10-trichoene-2-ol as natural metabolites in F. culmorum cultures.

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