Biotransformation of Vinclozolin by the Fungus Cunninghamella elegans

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• 作者：Jairaj V. Pothuluri ; James P. Freeman ; Thomas M. Heinze ; Richard D. Beger ; and Carl E. Cerniglia
• 刊名：Journal of Agricultural and Food Chemistry
• 出版年：2000
• 出版时间：December 2000
• 年：2000
• 卷：48
• 期：12
• 页码：6138 - 6148
• 全文大小：132K
• 年卷期：v.48,no.12(December 2000)
• ISSN：1520-5118

文摘

This study investigated the biotransformation of the dicarboximide fungicide vinclozolin [3-(3,5-dichlorophenyl)-5-methyl-5-vinyl-1,3-oxazolidine-2,4-dione] by the fungus Cunninghamella elegans.Experiments with phenyl-[U-ring-¹⁴C]vinclozolin showed that after 96 h incubation, 93% had beentransformed to four major metabolites. Metabolites were separated by HPLC and characterized bymass and NMR spectroscopy. Biotransformation occurred predominantly on the oxazolidine-2,4-dione portion of vinclozolin. The metabolites were identified as the 3R- and 3S- isomers of 3',5'-dichloro-2,3,4-trihydroxy-2-methylbutyranilide, N-(2-hydroxy-2-methyl-1-oxobuten-3-yl)-3,5-dichlorophenyl-1-carbamic acid, and 3',5'-dichloro-2-hydroxy-2-methylbut-3-enanilide. The enanilidecompound has been reported previously as a plant and mammalian metabolite and is implicated tocontain antiandrogenic activity. The 3R- and 3S- isomers of 3',5'-dichloro-2,3,4-trihydroxy-2-methylbutyranilide are novel metabolites.Keywords: Vinclozolin; dicarboximide fungicide; fungal biotransformation; Cunninghamellaelegans