Skip to main content
PMC home page
Applied and Environmental Microbiology logoLink to Applied and Environmental Microbiology
. 1996 May;62(5):1788–1792. doi: 10.1128/aem.62.5.1788-1792.1996

Fluorene Oxidation In Vivo by Phanerochaete chrysosporium and In Vitro during Manganese Peroxidase-Dependent Lipid Peroxidation

B W Bogan, R T Lamar, K E Hammel
PMCID: PMC1388858  PMID: 16535320

Abstract

The oxidation of fluorene, a polycyclic hydrocarbon which is not a substrate for fungal lignin peroxidase, was studied in liquid cultures of Phanerochaete chrysosporium and in vitro with P. chrysosporium extracellular enzymes. Intact fungal cultures metabolized fluorene to 9-hydroxyfluorene via 9-fluorenone. Some conversion to more-polar products was also observed. Oxidation of fluorene to 9-fluorenone was also obtained in vitro in a system that contained manganese(II), unsaturated fatty acid, and either crude P. chrysosporium peroxidases or purified recombinant manganese peroxidase. The oxidation of fluorene in vitro was inhibited by the free-radical scavenger butylated hydroxytoluene but not by the lignin peroxidase inhibitor NaVO(inf3). Manganese(III)-malonic acid complexes could not oxidize fluorene. These results indicate that fluorene oxidation in vitro was a consequence of lipid peroxidation mediated by P. chrysosporium manganese peroxidase. The rates of fluorene and diphenylmethane disappearance in vitro were significantly faster than those of true polycyclic aromatic hydrocarbons or fluoranthenes, whose rates of disappearance were ionization potential dependent. This result indicates that the initial oxidation of fluorene proceeds by mechanisms other than electron abstraction and that benzylic hydrogen abstraction is probably the route for oxidation.

Full Text

The Full Text of this article is available as a PDF (214.1 KB).

Selected References

These references are in PubMed. This may not be the complete list of references from this article.

  1. Archibald F. S. Lignin Peroxidase Activity Is Not Important in Biological Bleaching and Delignification of Unbleached Kraft Pulp by Trametes versicolor. Appl Environ Microbiol. 1992 Sep;58(9):3101–3109. doi: 10.1128/aem.58.9.3101-3109.1992. [DOI] [PMC free article] [PubMed] [Google Scholar]
  2. Bogan B. W., Lamar R. T. One-electron oxidation in the degradation of creosote polycyclic aromatic hydrocarbons by Phanerochaete chrysosporium. Appl Environ Microbiol. 1995 Jul;61(7):2631–2635. doi: 10.1128/aem.61.7.2631-2635.1995. [DOI] [PMC free article] [PubMed] [Google Scholar]
  3. Bumpus J. A., Aust S. D. Biodegradation of DDT [1,1,1-trichloro-2,2-bis(4-chlorophenyl)ethane] by the white rot fungus Phanerochaete chrysosporium. Appl Environ Microbiol. 1987 Sep;53(9):2001–2008. doi: 10.1128/aem.53.9.2001-2008.1987. [DOI] [PMC free article] [PubMed] [Google Scholar]
  4. Bumpus J. A. Biodegradation of polycyclic hydrocarbons by Phanerochaete chrysosporium. Appl Environ Microbiol. 1989 Jan;55(1):154–158. doi: 10.1128/aem.55.1.154-158.1989. [DOI] [PMC free article] [PubMed] [Google Scholar]
  5. Cavalieri E. L., Rogan E. G., Roth R. W., Saugier R. K., Hakam A. The relationship between ionization potential and horseradish peroxidase/hydrogen peroxide-catalyzed binding of aromatic hydrocarbons to DNA. Chem Biol Interact. 1983 Oct 15;47(1):87–109. doi: 10.1016/0009-2797(83)90150-3. [DOI] [PubMed] [Google Scholar]
  6. Cavalieri E., Rogan E. Role of radical cations in aromatic hydrocarbon carcinogenesis. Environ Health Perspect. 1985 Dec;64:69–84. doi: 10.1289/ehp.856469. [DOI] [PMC free article] [PubMed] [Google Scholar]
  7. Glenn J. K., Akileswaran L., Gold M. H. Mn(II) oxidation is the principal function of the extracellular Mn-peroxidase from Phanerochaete chrysosporium. Arch Biochem Biophys. 1986 Dec;251(2):688–696. doi: 10.1016/0003-9861(86)90378-4. [DOI] [PubMed] [Google Scholar]
  8. Hadar Y., Cohen-Arazi E. Chemical Composition of the Edible Mushroom Pleurotus ostreatus Produced by Fermentation. Appl Environ Microbiol. 1986 Jun;51(6):1352–1354. doi: 10.1128/aem.51.6.1352-1354.1986. [DOI] [PMC free article] [PubMed] [Google Scholar]
  9. Hammel K. E., Gai W. Z., Green B., Moen M. A. Oxidative degradation of phenanthrene by the ligninolytic fungus Phanerochaete chrysosporium. Appl Environ Microbiol. 1992 Jun;58(6):1832–1838. doi: 10.1128/aem.58.6.1832-1838.1992. [DOI] [PMC free article] [PubMed] [Google Scholar]
  10. Hammel K. E., Kalyanaraman B., Kirk T. K. Oxidation of polycyclic aromatic hydrocarbons and dibenzo[p]-dioxins by Phanerochaete chrysosporium ligninase. J Biol Chem. 1986 Dec 25;261(36):16948–16952. [PubMed] [Google Scholar]
  11. Kersten P. J., Tien M., Kalyanaraman B., Kirk T. K. The ligninase of Phanerochaete chrysosporium generates cation radicals from methoxybenzenes. J Biol Chem. 1985 Mar 10;260(5):2609–2612. [PubMed] [Google Scholar]
  12. Lamar R. T., Larsen M. J., Kirk T. K. Sensitivity to and Degradation of Pentachlorophenol by Phanerochaete spp. Appl Environ Microbiol. 1990 Nov;56(11):3519–3526. doi: 10.1128/aem.56.11.3519-3526.1990. [DOI] [PMC free article] [PubMed] [Google Scholar]
  13. Moen M. A., Hammel K. E. Lipid Peroxidation by the Manganese Peroxidase of Phanerochaete chrysosporium Is the Basis for Phenanthrene Oxidation by the Intact Fungus. Appl Environ Microbiol. 1994 Jun;60(6):1956–1961. doi: 10.1128/aem.60.6.1956-1961.1994. [DOI] [PMC free article] [PubMed] [Google Scholar]
  14. Renganathan V., Miki K., Gold M. H. Multiple molecular forms of diarylpropane oxygenase, an H2O2-requiring, lignin-degrading enzyme from Phanerochaete chrysosporium. Arch Biochem Biophys. 1985 Aug 15;241(1):304–314. doi: 10.1016/0003-9861(85)90387-x. [DOI] [PubMed] [Google Scholar]
  15. Stewart P., Whitwam R. E., Kersten P. J., Cullen D., Tien M. Efficient expression of a Phanerochaete chrysosporium manganese peroxidase gene in Aspergillus oryzae. Appl Environ Microbiol. 1996 Mar;62(3):860–864. doi: 10.1128/aem.62.3.860-864.1996. [DOI] [PMC free article] [PubMed] [Google Scholar]
  16. Tien M., Kirk T. K. Lignin-degrading enzyme from Phanerochaete chrysosporium: Purification, characterization, and catalytic properties of a unique H(2)O(2)-requiring oxygenase. Proc Natl Acad Sci U S A. 1984 Apr;81(8):2280–2284. doi: 10.1073/pnas.81.8.2280. [DOI] [PMC free article] [PubMed] [Google Scholar]
  17. Valli K., Brock B. J., Joshi D. K., Gold M. H. Degradation of 2,4-dinitrotoluene by the lignin-degrading fungus Phanerochaete chrysosporium. Appl Environ Microbiol. 1992 Jan;58(1):221–228. doi: 10.1128/aem.58.1.221-228.1992. [DOI] [PMC free article] [PubMed] [Google Scholar]
  18. Valli K., Gold M. H. Degradation of 2,4-dichlorophenol by the lignin-degrading fungus Phanerochaete chrysosporium. J Bacteriol. 1991 Jan;173(1):345–352. doi: 10.1128/jb.173.1.345-352.1991. [DOI] [PMC free article] [PubMed] [Google Scholar]
  19. Valli K., Wariishi H., Gold M. H. Degradation of 2,7-dichlorodibenzo-p-dioxin by the lignin-degrading basidiomycete Phanerochaete chrysosporium. J Bacteriol. 1992 Apr;174(7):2131–2137. doi: 10.1128/jb.174.7.2131-2137.1992. [DOI] [PMC free article] [PubMed] [Google Scholar]
  20. Vazquez-Duhalt R., Westlake D. W., Fedorak P. M. Lignin peroxidase oxidation of aromatic compounds in systems containing organic solvents. Appl Environ Microbiol. 1994 Feb;60(2):459–466. doi: 10.1128/aem.60.2.459-466.1994. [DOI] [PMC free article] [PubMed] [Google Scholar]

Articles from Applied and Environmental Microbiology are provided here courtesy of American Society for Microbiology (ASM)

RESOURCES