Fungal Metabolism of Biphenyl

Overview

Journal Biochem J

Specialty Biochemistry

Date 1979 Jan 15

PMID 435280

Citations 15

Authors

R H Dodge

C E Cerniglia

D T Gibson

Affiliations

Soon will be listed here.

Abstract

Cunninghamella elegans grown on Sabouraud dextrose broth transformed biphenyl to produce 2-, 3- and 4-hydroxybiphenyl, as well as 4,4'-dihydroxybiphenyl as free phenols. A compound tentatively identified as 2,4'-dihydroxybiphenyl was also produced. When 4-hydroxybiphenyl or 2-hydroxybiphenyl replaced biphenyl as the substrate, C. elegans produced 4,4'-dihydroxybiphenyl and 2,5-dihydroxybiphenyl respectively. The compound identified as 2,4'-dihydroxybiphenyl was produced from both substrates. A survey of 11 species of fungi known to degrade hydrocarbons revealed two species that were comparable to C. elegans in their ability to convert biphenyl into free phenols. In addition to free phenolic metabolites, deconjugation experiments indicated that 44% of the known metabolites present in the culture filtrate were present in the form of conjugates. These results suggest that the transformation of biphenyl by C. elegans is similar to that found in mammalian systems.

Citing Articles

Fungal Metabolism of n-Alkylbenzenes.

Fedorak P, Westlake D Appl Environ Microbiol. 1986; 51(2):435-7.

PMID: 16347000 PMC: 238889. DOI: 10.1128/aem.51.2.435-437.1986.

Microbial production of 4,4'-dihydroxybiphenyl: biphenyl hydroxylation by fungi.

Schwartz R, Williams A, Hutchinson D Appl Environ Microbiol. 1980; 39(4):702-8.

PMID: 16345536 PMC: 291407. DOI: 10.1128/aem.39.4.702-708.1980.

Novel ring cleavage products in the biotransformation of biphenyl by the yeast Trichosporon mucoides.

Sietmann R, Hammer E, Specht M, Cerniglia C, Schauer F Appl Environ Microbiol. 2001; 67(9):4158-65.

PMID: 11526019 PMC: 93143. DOI: 10.1128/AEM.67.9.4158-4165.2001.

Biotransformation of biphenyl by Paecilomyces lilacinus and characterization of ring cleavage products.

Gesell M, Hammer E, Specht M, Francke W, Schauer F Appl Environ Microbiol. 2001; 67(4):1551-7.

PMID: 11282604 PMC: 92768. DOI: 10.1128/AEM.67.4.1551-1557.2001.

Isolation and characterization of a dibenzofuran-degrading yeast: identification of oxidation and ring cleavage products.

Hammer E, Krowas D, Schafer A, Specht M, Francke W, Schauer F Appl Environ Microbiol. 1998; 64(6):2215-9.

PMID: 9603837 PMC: 106301. DOI: 10.1128/AEM.64.6.2215-2219.1998.

References

WEST H, Lawson J, Miller I, MATHURA G . The fate of diphenyl in the rat. Arch Biochem Biophys. 1956; 60(1):14-20. DOI: 10.1016/0003-9861(56)90390-3. View

Cerniglia C, Hebert R, Szaniszlo P, Gibson D . Fungal transformation of naphthalene. Arch Microbiol. 1978; 117(2):135-43. DOI: 10.1007/BF00402301. View

Billings R, McMahon R . Microsomal biphenyl hydroxylation: the formation of 3- hydroxybiphenyl and biphenyl catechol. Mol Pharmacol. 1978; 14(1):145-54. View

Wiebkin P, Fry J, Jones C, Lowing R, Bridges J . The metabolism of biphenyl by isolated viable rat hepatocytes. Xenobiotica. 1976; 6(12):725-43. DOI: 10.3109/00498257609151390. View

Meyer T, Larsen J, Hansen E, SCHELINE R . The metabolism of biphenyl. III. Phenolic metabolites in the pig. Acta Pharmacol Toxicol (Copenh). 1976; 39(4):433-41. DOI: 10.1111/j.1600-0773.1976.tb03194.x. View

Meyer T, SCHELINE R . The metabolism of biphenyl. II. Phenolic metabolites in the rat. Acta Pharmacol Toxicol (Copenh). 1976; 39(4):419-32. DOI: 10.1111/j.1600-0773.1976.tb03193.x. View

Raig P, AMMON R . [Gas chromatographic analysis of phenolic metabolic products of biphenyl]. Arzneimittelforschung. 1970; 20(9):1266-9. View

HAKKINEN I, SILTANEN E, HERNBERG S, Seppalainen A, Karli P, Vikkula E . Diphenyl poisoning in fruit paper production: a new health hazard. Arch Environ Health. 1973; 26(2):70-4. DOI: 10.1080/00039896.1973.10666226. View

Smith R, Rosazza J . Microbial models of mammalian metabolism. Aromatic hydroxylation. Arch Biochem Biophys. 1974; 161(2):551-8. DOI: 10.1016/0003-9861(74)90338-5. View

10.

McPHERSON F, Bridges J, Parke D . In vitro enhancement of hepatic microsomal biphenyl 2-hydroxylation by carcinogens. Nature. 1974; 252(5483):488-9. DOI: 10.1038/252488a0. View

11.

Cerniglia C, Perry J . Crude oil degradation by microorganisms isolated from the marine environment. Z Allg Mikrobiol. 1973; 13(4):299-306. DOI: 10.1002/jobm.3630130403. View

12.

Gibson D, Roberts R, Wells M, Kobal V . Oxidation of biphenyl by a Beijerinckia species. Biochem Biophys Res Commun. 1973; 50(2):211-9. DOI: 10.1016/0006-291x(73)90828-0. View

13.

Boyd D, Daly J, Jerina D . Rearrangement of (1- 2 H)- and (2- 2 H)naphthalene 1,2-oxides to 1-naphthol. Mechanism of the NIH shift. Biochemistry. 1972; 11(10):1961-6. DOI: 10.1021/bi00760a035. View

14.

Wiseman A, Gondal J, Sims P . 4'-Hydroxylation of biphenyl by yeast containing cytochrome P-450: radiation and thermal stability, comparisons with liver enzyme (oxidized and reduced forms). Biochem Soc Trans. 1975; 3(2):278-81. DOI: 10.1042/bst0030278. View

15.

Tomaszewski J, Jerina D, Daly J . Deuterium isotope effects during formation of phenols by hepatic monoxygenases. Evidence for an alternative to arene oxide pathway. Biochemistry. 1975; 14(9):2024-31. DOI: 10.1021/bi00680a033. View

16.

Catelani D, Sorlini C, Treccani V . The metabolism of biphenyl by Pseudomonas putida. Experientia. 1971; 27(10):1173-4. DOI: 10.1007/BF02286908. View

17.

Ernst W . [Conversion and elimination of 2-hydroxydiphenyl in the rat]. Arzneimittelforschung. 1965; 15(6):632-6. View