Biotransformation of vinclozolin by the fungus Cunninghamella elegans

被引:33
作者
Pothuluri, JV [1 ]
Freeman, JP [1 ]
Heinze, TM [1 ]
Beger, RD [1 ]
Cerniglia, CE [1 ]
机构
[1] US FDA, Natl Ctr Toxicol Res, Div Microbiol, Jefferson, AR 72079 USA
关键词
vinclozolin; dicarboximide fungicide; fungal biotransformation; Cunninghamella elegans;
D O I
10.1021/jf0008543
中图分类号
S [农业科学];
学科分类号
09 ;
摘要
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-(14)C]vinclozolin showed that after 96 h incubation, 93% had been transformed to four major metabolites. Metabolites were separated by HPLC and characterized by mass 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-dichlo-rophenyl-1-carbamic acid, and 3',5'-dichloro-2-hydroxy-2-methylbut-3-enanilide. The enanilide compound has been reported previously as a plant and mammalian metabolite and is implicated to contain antiandrogenic activity. The 3R- and 3S- isomers of 3',5'-dichloro-2,3,4-trihydroxy-2-methylbutyranilide are novel metabolites.
引用
收藏
页码:6138 / 6148
页数:11
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