The metabolism of chlorinated aromatic pollutants by the frog

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Abstract
The metabolism of several chlorinated aromatic pollutants has been studied using the frog species Rana pipiens as a model system. The substrates were administered by intraperitoneal injection and the metabolites were isolated and identified by chromatographic and spectroscopic methods. Chlorinated biphenyls, naphthalenes, and benzenes gave a range of hydroxylated products: 4-chlorobiphenyl was converted into 4′-chloro-4-biphenylol, 4′-chloro-3,4-bi-phenyldiol, and 4′-chloro-3-methoxy-4-biphenylol; 4,4′-dichlorobiphenyl gave 4,4′-dichloro-3-biphenylol and commercial Aroclor 1254 yielded mono-, di- and tri-chlorobiphenylols; 1-chloro- and 1,4-dichloro-naphthalene gave 4-chloro- and 2,4-dichloro-naphthol respectively; a series of lower chlorinated (monotetra) benzene isomers were also hydroxylated, whereas the pentachloro and hexachloro isomers did not yield any metabolic products. The results also suggested that biohydroxylation in the frog is similar to that of mammalian systems in which arene oxide intermediates are involved.

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