A comparison of biphenyl 4-hydroxylation and 4-methoxybiphenyl O-demethylation in rat liver microsomes

Fry, Jeffrey R.

doi:10.1016/0006-2952(81)90199-4

Biochemical Pharmacology

1981

DOI: 10.1016/0006-2952(81)90199-4

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A comparison of biphenyl 4-hydroxylation and 4-methoxybiphenyl O-demethylation in rat liver microsomes

Jeffrey R. Fry

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Cited by 14 publications

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“…Mineralization has been proven for the white rot fungus Phanerochaete chrysosporium producing 14 CO 2 from radioactive labeled biphenyl (34). However, the most common transformation reaction is the hydroxylation of the aromatic ring, leading to a variety of mono-, di-and trihydroxylated intermediates (1,2,4,8,13,20,26,30). Filamentous fungi and mammals favor initial hydroxylation at the 2 and 4 positions, respectively, followed by further hydroxylation on the second ring (6,12,25,31).…”

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Novel Ring Cleavage Products in the Biotransformation of Biphenyl by the Yeast Trichosporon mucoides

Sietmann

Hammer

Specht

et al. 2001

Appl Environ Microbiol

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The yeast Trichosporon mucoides, grown on either glucose or phenol, was able to transform biphenyl into a variety of mono-, di-, and trihydroxylated derivatives hydroxylated on one or both aromatic rings. While some of these products accumulated in the supernatant as dead end products, the ortho-substituted dihydroxylated biphenyls were substrates for further oxidation and ring fission. These ring fission products were identified by high-performance liquid chromatography, gas chromatography-mass spectrometry, and nuclear magnetic resonance analyses as phenyl derivatives of hydroxymuconic acids and the corresponding pyrones. Seven novel products out of eight resulted from the oxidation and ring fission of 3,4-dihydroxybiphenyl. Using this compound as a substrate, 2-hydroxy-4-phenylmuconic acid, (5-oxo-3-phenyl-2,5-dihydrofuran-2-yl)acetic acid, and 3-phenyl-2-pyrone-6-carboxylic acid were identified. Ring cleavage of 3,4,4-trihydroxybiphenyl resulted in the formation of [5-oxo-3-(4-hydroxyphenyl)-2,5-dihydrofuran-2-yl]acetic acid, 4-(4-hydroxyphenyl)-2-pyrone-6-carboxylic acid, and 3-(4-hydroxyphenyl)-2-pyrone-6-carboxylic acid. 2,3,4-Trihydroxybiphenyl was oxidized to 2-hydroxy-5-phenylmuconic acid, and 4-phenyl-2-pyrone-6-carboxylic acid was the transformation product of 3,4,5-trihydroxybiphenyl. All these ring fission products were considerably less toxic than the hydroxylated derivatives.

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confidence: 99%

Novel Ring Cleavage Products in the Biotransformation of Biphenyl by the Yeast Trichosporon mucoides

Sietmann

Hammer

Specht

et al. 2001

Appl Environ Microbiol

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Influence of the sulphation inhibitor, 2,6-dichloro-4-nitrophenol, on the production, and conjugation, of 4-hydroxybiphenyl generated from 4-methoxybiphenyl by rat isolated hepatocytes

Fry¹,

Paterson²

1987

Biochemical Pharmacology

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The in vivo induction of rat hepatic cytochrome P450-dependent enzyme activities and their maintenance in culture

Hammond¹,

Fry²

1990

Biochemical Pharmacology

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A comparison of biphenyl 4-hydroxylation and 4-methoxybiphenyl O-demethylation in rat liver microsomes

Cited by 14 publications

References 18 publications

Novel Ring Cleavage Products in the Biotransformation of Biphenyl by the Yeast Trichosporon mucoides

Novel Ring Cleavage Products in the Biotransformation of Biphenyl by the Yeast Trichosporon mucoides

Influence of the sulphation inhibitor, 2,6-dichloro-4-nitrophenol, on the production, and conjugation, of 4-hydroxybiphenyl generated from 4-methoxybiphenyl by rat isolated hepatocytes

The in vivo induction of rat hepatic cytochrome P450-dependent enzyme activities and their maintenance in culture

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