PMID: 11312787Apr 21, 2001Paper

Biotransformation of vinclozolin by the fungus Cunninghamella elegans

Journal of Agricultural and Food Chemistry
J V PothuluriC E Cerniglia

Abstract

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.

References

Feb 1, 1978·Archives of Biochemistry and Biophysics·C E Cerniglia, D T Gibson
Jan 1, 1992·Journal of Industrial Microbiology·J B Sutherland
Jun 1, 1991·Journal of Environmental Science and Health. Part. B, Pesticides, Food Contaminants, and Agricultural Wastes·L A Golovleva Nefedova MYu
Oct 1, 1990·Applied and Environmental Microbiology·J V PothuluriC E Cerniglia
Oct 1, 1994·Bulletin of Environmental Contamination and Toxicology·E K FrederickR F Turco
Sep 1, 1996·Mutagenesis·P HreliaG Cantelli Forti
Feb 1, 1997·Archives of Environmental Contamination and Toxicology·J V PothuluriC E Cerniglia
Mar 1, 1997·Journal of Molecular Medicine : Official Organ of the Gesellschaft Deutscher Naturforscher Und Ärzte·W R Kelce, E M Wilson
Jan 1, 1998·Biomarkers : Biochemical Indicators of Exposure, Response, and Susceptibility to Chemicals·G Cantelli-Forti, A Camerino

❮ Previous
Next ❯

Citations

Mar 8, 2005·Archives of Environmental Contamination and Toxicology·J SeoH-G Hur
Jan 26, 2013·Chemical Reviews·Bagher Eftekhari-SisAli Akbari
Aug 16, 2008·Toxicological Sciences : an Official Journal of the Society of Toxicology·Adolfo Sierra-SantoyoMichael F Hughes
Oct 12, 2010·PloS One·Carlos Guerrero-BosagnaMichael K Skinner
Aug 28, 2014·Acta Crystallographica. Section E, Structure Reports Online·Seonghwa ChoTae Ho Kim
Jul 24, 2012·Aquatic Toxicology·Azadeh HatefOtomar Linhart
Sep 9, 2008·Biotechnology Advances·Sepuri Asha, Maravajhala Vidyavathi
Feb 10, 2006·Annals of the New York Academy of Sciences·Michael K Skinner, Matthew D Anway
Jul 30, 2004·Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences·Adolfo Sierra-SantoyoMichael F Hughes
Aug 6, 2005·Drug Metabolism and Disposition : the Biological Fate of Chemicals·Christopher L ShafferShiyin Yee
Jun 5, 2008·Journal of Agricultural and Food Chemistry·Julian BursztykaJean-Pierre Cravedi

❮ Previous
Next ❯

Related Concepts

Related Feeds

Antifungals

An antifungal, also known as an antimycotic medication, is a pharmaceutical fungicide or fungistatic used to treat and prevent mycosis such as athlete's foot, ringworm, candidiasis, cryptococcal meningitis, and others. Discover the latest research on antifungals here.