Skip to main content
NCBI home page
Applied and Environmental Microbiology logoLink to Applied and Environmental Microbiology
. 1996 Dec;62(12):4563–4567. doi: 10.1128/aem.62.12.4563-4567.1996

Oxidation of Anthracene and Benzo[a]pyrene by Laccases from Trametes versicolor

P J Collins, M Kotterman, J A Field, A Dobson
PMCID: PMC1389006  PMID: 16535468

Abstract

The in vitro oxidation of the two polycyclic aromatic hydrocarbons anthracene and benzo[a]pyrene, which have ionization potentials of <=7.45 eV, is catalyzed by laccases from Trametes versicolor. Crude laccase preparations were able to oxidize both anthracene and the potent carcinogen benzo[a]pyrene. Oxidation of benzo[a]pyrene was enhanced by the addition of the cooxidant 2,2(prm1)-azinobis(3-ethylbenzthiazoline-6-sulfonate) (ABTS), while an increased anthracene oxidizing ability was observed in the presence of the low-molecular-weight culture fluid ultrafiltrate. Two purified laccase isozymes from T. versicolor were found to have similar oxidative activities towards anthracene and benzo[a]pyrene. Oxidation of anthracene by the purified isozymes was enhanced in the presence of ABTS, while ABTS was essential for the oxidation of benzo[a]pyrene. In all cases anthraquinone was identified as the major end product of anthracene oxidation. These findings indicate that laccases may have a role in the oxidation of polycyclic aromatic hydrocarbons by white rot fungi.

Full Text

The Full Text of this article is available as a PDF (253.2 KB).

Selected References

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

  1. Bezalel L., Hadar Y., Cerniglia C. E. Mineralization of Polycyclic Aromatic Hydrocarbons by the White Rot Fungus Pleurotus ostreatus. Appl Environ Microbiol. 1996 Jan;62(1):292–295. doi: 10.1128/aem.62.1.292-295.1996. [DOI] [PMC free article] [PubMed] [Google Scholar]
  2. Bourbonnais R., Paice M. G. Oxidation of non-phenolic substrates. An expanded role for laccase in lignin biodegradation. FEBS Lett. 1990 Jul 2;267(1):99–102. doi: 10.1016/0014-5793(90)80298-w. [DOI] [PubMed] [Google Scholar]
  3. Bourbonnais R., Paice M. G., Reid I. D., Lanthier P., Yaguchi M. Lignin oxidation by laccase isozymes from Trametes versicolor and role of the mediator 2,2'-azinobis(3-ethylbenzthiazoline-6-sulfonate) in kraft lignin depolymerization. Appl Environ Microbiol. 1995 May;61(5):1876–1880. doi: 10.1128/aem.61.5.1876-1880.1995. [DOI] [PMC free article] [PubMed] [Google Scholar]
  4. Bradford M. M. A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal Biochem. 1976 May 7;72:248–254. doi: 10.1016/0003-2697(76)90527-3. [DOI] [PubMed] [Google Scholar]
  5. 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]
  6. Dipple A., Cheng S. C., Bigger C. A. Polycyclic aromatic hydrocarbon carcinogens. Prog Clin Biol Res. 1990;347:109–127. [PubMed] [Google Scholar]
  7. Field J. A., de Jong E., Feijoo Costa G., de Bont J. A. Biodegradation of polycyclic aromatic hydrocarbons by new isolates of white rot fungi. Appl Environ Microbiol. 1992 Jul;58(7):2219–2226. doi: 10.1128/aem.58.7.2219-2226.1992. [DOI] [PMC free article] [PubMed] [Google Scholar]
  8. Fåhraeus G., Reinhammar B. Large scale production and purification of laccase from cultures of the fungus Polyporus versicolor and some properties of laccase A. Acta Chem Scand. 1967;21(9):2367–2378. doi: 10.3891/acta.chem.scand.21-2367. [DOI] [PubMed] [Google Scholar]
  9. Haemmerli S. D., Leisola M. S., Sanglard D., Fiechter A. Oxidation of benzo(a)pyrene by extracellular ligninases of Phanerochaete chrysosporium. Veratryl alcohol and stability of ligninase. J Biol Chem. 1986 May 25;261(15):6900–6903. [PubMed] [Google Scholar]
  10. Hammel K. E., Green B., Gai W. Z. Ring fission of anthracene by a eukaryote. Proc Natl Acad Sci U S A. 1991 Dec 1;88(23):10605–10608. doi: 10.1073/pnas.88.23.10605. [DOI] [PMC free article] [PubMed] [Google Scholar]
  11. 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]
  12. Kotterman M., Wasseveld R. A., Field J. A. Hydrogen Peroxide Production as a Limiting Factor in Xenobiotic Compound Oxidation by Nitrogen-Sufficient Cultures of Bjerkandera sp. Strain BOS55 Overproducing Peroxidases. Appl Environ Microbiol. 1996 Mar;62(3):880–885. doi: 10.1128/aem.62.3.880-885.1996. [DOI] [PMC free article] [PubMed] [Google Scholar]
  13. Miller E. C., Miller J. A. Searches for ultimate chemical carcinogens and their reactions with cellular macromolecules. Cancer. 1981 May 15;47(10):2327–2345. doi: 10.1002/1097-0142(19810515)47:10<2327::aid-cncr2820471003>3.0.co;2-z. [DOI] [PubMed] [Google Scholar]
  14. 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]
  15. 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]
  16. Wariishi H., Valli K., Gold M. H. Manganese(II) oxidation by manganese peroxidase from the basidiomycete Phanerochaete chrysosporium. Kinetic mechanism and role of chelators. J Biol Chem. 1992 Nov 25;267(33):23688–23695. [PubMed] [Google Scholar]
  17. Youn H. D., Kim K. J., Maeng J. S., Han Y. H., Jeong I. B., Jeong G., Kang S. O., Hah Y. C. Single electron transfer by an extracellular laccase from the white-rot fungus Pleurotus ostreatus. Microbiology. 1995 Feb;141(Pt 2):393–398. doi: 10.1099/13500872-141-2-393. [DOI] [PubMed] [Google Scholar]

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

RESOURCES