Biotransformation of Vinclozolin by the Fungus Cunninghamella elegans

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.

Isolation and characterization of chlorate resistant mutants from nitrate-nonutilizing fungus Phycomyces blakesleeanus

“…It is known that Cunninghamella elegans (Lendner) Lunn & Shipton, a zygomycetous fungus, has the potential to detoxify or inactivate various polycyclic aromatic hydrocarbons by forming sulfate conjugates (Pothuluri et al, 1996;1998).…”

Liquid chromatography determination of the anti-androgen vinclozolin and its metabolites in rat serum

“…V, M1 and M2 have previously been identified in the serum of rats administered repeated oral doses of V [3,11]. M3 has been detected as a V metabolite where biological systems are involved [12,19], however, there are other studies where its presence was not reported [3,13]. The presence of M3 in biological samples after exposure to V could be due to the acidic conditions used during analysis or production from V, M1 and M2 by the action of esterases.…”

“…In assays with bacteria and fungus present in soil and cultured in anaerobic and aerobic conditions, V was hydrolyzed to M1, M2 and M3 [19][20][21]. In addition, Pothuluri et al [13] characterized two other metabolites from V, N-(2-hydroxy-2-methyl-1-oxobuten-3-yl)-3,5-dichlorophenyl-1-carbamic acid and the 3R-and 3S-isomers of 3 ,5 -dichloro-2,3,4-trihydroxy-2-methylbutyranilide in C. elegans cultures. The latter metabolite was also detected in the liver of hens administered an oral dose of V [14].…”

“…V was the main chemical detected in minnow tissues and females accumulated significantly more V than males after 21 days of exposure [12]. Isomers of 3 ,5 -dichloro-2,3,4-trihydroxy-2-methylbutyranilide have been observed as metabolites of V in Cunninghamella elegans [13] and hens [14].…”

Comparative Purification and Characterization of Two Distinct Extracellular Monocrotophos Hydrolases Secreted byPenicillium aculeatumandFusarium pallidoroseumIsolated from Agricultural Fields

“…12) Fungi participate in biogeochemical cycles and the degradation of some xenobiotics in the biosphere. 13,14) To gain insight into fungus mediated degradation of OP pesticides, the present study was aimed to isolate and characterize broad-spectrum fungal OPHs capable of hydrolyzing MCP containing both the P-O-C linkage and the amide bond effectively.…”