A Glutathione Conjugate of 2,4-Dichloro-1-nitrobenzene: Its Detection as a Metabolic Intermediate and Further Metabolism in Mucor javanicus

Abstract

Formation of a 2,4-Dichloro-1-nitrobenzene glutathione conjugate [S-(5-chloro-2-nitro-phenyl) glutathione, 2] was confirmed in the cell-free system of Mucor javanicus which metabolizes 2,3- and 2,4-dichloro-1-nitrobenzenes into the corresponding chloro-methylthio-nitro-benzsnse or chloro-methylthiobenzenamines. Further metabolisms of 2, the corresponding cysteine conjugate (3) and 5-chloro-2-nitrobenzenethiol (4) were investigated. Oxidation products (S-oxides and S-dioxides) of the formerly identified methylthio-containing metabolites were isolated from the growing cultures of the fungus administered 2. S-(5-Chloro-2-nitrophenyl)cysteine (3) and N-acetyl-S-(5-chloro-2-nitrophenyl)cysteine (7) were newly identified as metabolites of 2 in the resting cell system of the fungus. © 1987, Pesticide Science Society of Japan. All rights reserved.