Biotransformation of vinclozolin by the fungus Cunninghamella elegans.
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 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-dichlorophenyl-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.
Pothuluri
J V
JV
National Center for Toxicological Research, Food and Drug Administration, Jefferson, Arkansas 72079, USA. JPothuluri@nctr.fda.gov
Freeman
J P
JP
Heinze
T M
TM
Beger
R D
RD
Cerniglia
C E
CE
D001711:Biotransformation; D020093:Cunninghamella / Q000378:metabolism*; D005659:Fungicides, Industrial / Q000493:pharmacokinetics*; D007536:Isomerism; D010080:Oxazoles / Q000493:pharmacokinetics*
D005659:Fungicides, Industrial; D010080:Oxazoles; C025643:vinclozolin