Biphenyl hydroxylation and its induction differ between montane voles and Swiss Webster mice

Makary, Moheb H.; Brindley, William A.

doi:10.1016/0048-3575(83)90037-8

Pesticide Biochemistry and Physiology

1983

DOI: 10.1016/0048-3575(83)90037-8

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Biphenyl hydroxylation and its induction differ between montane voles and Swiss Webster mice

Moheb H. Makary¹,

William A. Brindley²

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Cited by 6 publications

(2 citation statements)

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“…Their fungal and mammalian metabolism has been previously investigated thoroughly (7,11), and it was found that the most important transformation reactions proceed via hydroxylation of the aromatic ring, whereby various hydroxylated biphenyls are produced. Mono-, di-, and trihydroxylated chlorinated biphenyls may be generated by cometabolism of polychlorinated biphenyls with biphenyl-grown bacteria (6).…”

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confidence: 99%

Metabolism of 2,2'-dihydroxybiphenyl by Pseudomonas sp. strain HBP1: production and consumption of 2,2',3-trihydroxybiphenyl

1993

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Cells of Pseudomonas sp. strain HBP1 grown on 2-hydroxy-or 2,2'-dihydroxybiphenyl contain NADHdependent monooxygenase activity that hydroxylates 2,2'-dihydroxybiphenyl. The product of this reaction was identified as 2,2',3-trihydroxybiphenyl by 1H nuclear magnetic resonance and mass spectrometry. Furthermore, the monooxygenase activity also hydroxylates 2,2',3-trihydroxybiphenyl at the C-3' position, yielding 2,2',3,3'-tetrahydroxybiphenyl as a product. An extradiol ring cleavage dioxygenase activity that acts on both 2,2',3-tri-and 2,2',3,3'-tetrahydroxybiphenyl was partially purified. Both substrates yielded yellow metacleavage compounds that were identified as 2-hydroxy-6-(2-hydroxyphenyl)-6-oxo-2,4-hexadienoic acid and 2-hydroxy-6-(2,3-dihydroxyphenyl)-6-oxo-2,4-hexadienoic acid, respectively, by gas chromatography-mass spectrometry analysis of their respective trimethylsilyl derivatives. The meta-cleavage products were not stable in aqueous incubation mixtures but gave rise to their cyclization products, 3-(chroman-4-on-2-yl)pyruvate and 3-(8-hydroxychroman-4-on-2-yl)pyruvate, respectively. In contrast to the meta-cleavage compounds, which were turned over to salicylic acid and 2,3-dihydroxybenzoic acid, the cyclization products are not substrates to the meta-cleavage product hydrolase activity. NADH-dependent salicylate monooxygenase activity catalyzed the conversions of salicylic acid and 2,3-dihydroxybenzoic acid to catechol and pyrogallol, respectively. The partially purified extradiol ring cleavage dioxygenase activity that acted on the hydroxybiphenyls also produced 2-hydroxymuconic semialdehyde and 2-hydroxymuconic acid from catechol and pyrogallol, respectively.Biphenyl and 2-hydroxybiphenyl have been used extensively as volatile fungicides, especially for the control of postharvest diseases (1). Their fungal and mammalian metabolism has been previously investigated thoroughly (7, 11), and it was found that the most important transformation reactions proceed via hydroxylation of the aromatic ring, whereby various hydroxylated biphenyls are produced. Mono-, di-, and trihydroxylated chlorinated biphenyls may be generated by cometabolism of polychlorinated biphenyls with biphenyl-grown bacteria (6). In order to gain better insight into the metabolic fate of such compounds in bacteria, we have previously investigated bacterial growth on 2-hydroxy-and 2,2'-dihydroxybiphenyl (9). Subsequently, isolates that were able to grow on 3-hydroxy-, 3,3'-dihydroxy-, and 4-hydroxybiphenyl were described (8). Two major routes for the bacterial metabolism of hydroxybiphenyls were recognized. One route proceeds via hydroxylation of the already hydroxylated aromatic ring by an NADHdependent monooxygenase followed by meta cleavage of 2,3-dihydroxybiphenyl. This route seems to be employed by the strains isolated on 2-hydroxy-and 3-hydroxybiphenyl (8, 9). The other route proceeds via dioxygenation of the nonhydroxylated aromatic ring, subsequent rearomatization, and meta cleavage. This pathway is utilized by Pseudomonas sp...

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confidence: 99%

Metabolism of 2,2'-dihydroxybiphenyl by Pseudomonas sp. strain HBP1: production and consumption of 2,2',3-trihydroxybiphenyl

1993

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“…The monohydroxylation of biphenyl is a detoxification process common to hepatic microsomes (25) and a range of fungi and actinomycetes (27). The chlorinated derivatives are frequently hydroxylated as well, even though several assays, such as erythrocyte lysis (T. L. Miller, Fed.…”

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confidence: 99%

Bacterial metabolism of hydroxylated biphenyls

Higson

Focht

1989

Appl Environ Microbiol

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Isolates able to grow on 3or 4-hydroxybiphenyl (HB) as the sole carbon source were obtained by enrichment culture. The 3-HB degrader Pseudomonas sp. strain FH12 used an NADPH-dependent monooxygenase restricted to 3-and 3,3'-HBs to introduce an ortho-hydroxyl. The 4-HB degrader Pseudomonas sp. strain FH23 used either a mono-or dioxygenase to generate a 2,3-diphenolic substitution pattern which allowed meta-fission of the aromatic ring. By using 3-chlorocatechol to inhibit catechol dioxygenase activity, it was found that 2-and 3-HBs were converted by FH23 to 2,3-HB, whereas biphenyl and 4-HB were attacked by dioxygenation. 4-HB was metabolized to 2,3,4'-trihydroxybiphenyl. Neither organism attacked chlorinated HBs. The degradation of 3-and 4-HBs by these strains is therefore analogous to the metabolism of biphenyl, 2-HB, and naphthalene in the requirement for 2,3-catechol formation.

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Use of mixed‐function oxygenases to monitor contaminant exposure in wildlife

Rattner

Hoffman

Marn

1989

Enviro Toxic and Chemistry

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This overview examines the utility of mixed‐function oxygenase (MFO) enzymes as a bio‐effects monitor for wildlife (amphibians, reptiles, birds and mammals) in view of their widespread use as indicators of contaminant exposure in aquatic invertebrates and fish. Phylogenetic trends in MFO activity, toxicological implications of induction and the relationship between contaminant exposure and MFO activity are discussed. Field studies using avian embryos and hatchlings suggest that MFO induction has utility for documenting contaminant exposure; however, findings in adult birds and mammals are equivocal. Age, sex and season are sources of variation that require consideration when undertaking field trials. Further understanding of MFO inducibility among species and application of recently developed analytical techniques including quantification of specific cytochrome P‐450 isozymes are warranted.

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Biphenyl hydroxylation and its induction differ between montane voles and Swiss Webster mice

Cited by 6 publications

References 11 publications

Metabolism of 2,2'-dihydroxybiphenyl by Pseudomonas sp. strain HBP1: production and consumption of 2,2',3-trihydroxybiphenyl

Metabolism of 2,2'-dihydroxybiphenyl by Pseudomonas sp. strain HBP1: production and consumption of 2,2',3-trihydroxybiphenyl

Bacterial metabolism of hydroxylated biphenyls

Use of mixed‐function oxygenases to monitor contaminant exposure in wildlife

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