Transformation of polycyclic aromatic hydrocarbons by laccase is strongly enhanced by phenolic compounds present in soil

Environmental Science and Technology

Volumn 41, Issue 8, 2007, Pages 2964-2971

  Cañas, Ana I ^a   Alcalde, Miguel ^b   Plou, Francisco ^b   Martínez, María Jesús ^a   Martínez, Ángel T ^a   Camarero, Susana ^a  

^a CENTRO DE INVESTIGACIONES BIOLÓGICAS   (Spain)

^b UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

NATURAL MEDIATORS; OXIDATION PRODUCTS; PHENOLIC COMPOUNDS; SYNTHETIC MEDIATORS;

ENZYMES; OXIDATION; PHENOLS;

POLYCYCLIC AROMATIC HYDROCARBONS;

1 HYDROXYBENZOTRIAZOLE; 2,2' AZINOBIS(3 ETHYLBENZOTHIAZOLINE 6 SULFONATE); 2,4,6 TRIMETHYLPHENOL; ACETOSYRINGONE; ANTHRACENE; APOCYNIN; BENZO[A]PYRENE; FERULIC ACID; FUNGAL ENZYME; LACCASE; LIGNIN; PARA COUMARIC ACID; PHENOL DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON; PYRENE; SINAPIC ACID; SYRINGALDEHYDE; THIAZOLE DERIVATIVE; TRIAZOLE DERIVATIVE; UNCLASSIFIED DRUG; VANILLIN;

ENZYMES; OXIDATION; PHENOLS; POLYCYCLIC AROMATIC HYDROCARBONS;

BIODEGRADATION; BIOREMEDIATION; FUNGUS; OXIDATION; PAH; PHENOLIC COMPOUND; POLLUTANT REMOVAL; SOIL REMEDIATION; TRANSFORMATION;

ARTICLE; BIOTRANSFORMATION; DEGRADATION; HUMUS; OXIDATION; SOIL POLLUTION; WASTE COMPONENT REMOVAL;

BASIDIOMYCOTA; BENZOTHIAZOLES; COUMARIC ACIDS; LACCASE; MOLECULAR STRUCTURE; PHENOLS; POLYCYCLIC HYDROCARBONS, AROMATIC; SOIL; SULFONIC ACIDS; TIME FACTORS; TRIAZOLES;

EID: 34247242778     PISSN: 0013936X     EISSN: None     Source Type: Journal    
DOI: 10.1021/es062328j     Document Type: Article

References (44)

1. Cerniglia, C. E. Biodegradation of polycyclic aromatic hydrocarbons. Biodegradation 1992, 3, 351.
2. Juhasz, A. L.; Naidu, R. Bioremediation of high molecular weight polycyclic aromatic hydrocarbons: a review of the microbial degradation of benzo[a]pyrene. Int. Biodeterior. Biodegrad. 2000, 45, 57.
3. Hammel, K. E.; Green, B.; Gai, W. Z. Ring fission of anthracene by a eukaryote. Proc. Natl. Acad. Sci. U.S.A. 1991, 88, 10605.
4. Günther, T.; Sack, U.; Hofrichter, M.; Lätz, M. Oxidation of PAH and PAH-derivatives by fungal and plant oxidoreductases. J. Basic Microb. 1998, 38, 113.
5. Haemmerli, S. D.; Leisola, M. S. A.; 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, 261, 6900.
6. Pickard, M. A.; Roman, R.; Tinoco, R.; Vázquez-Duhalt, R. Polycyclic aromatic hydrocarbon metabolism by white rot fungi and oxidation by Coriolopsis gallica UAMH 8260 laccase. Appl. Environ. Microbiol. 1999, 65, 3805.
7. Bezalel, L.; Hadar, Y.; Fu, P. P.; Freeman, J. C.; Cerniglia, C. E. Metabolism of phenanthrene by the white rot fungus Pleurotus ostreatus. Appl. Environ. Microbiol. 1996, 62, 2547.
8. Sack, U.; Hofrichter, M.; Fritsche, W. Degradation of polycyclic aromatic hydrocarbons by manganese peroxidase of Nematoloma frowardii. FEMS Microbiol. Lett. 1997, 152, 227.
9. Torres, E.; Bustos-Jaimes, I.; Le Borgne, S. Potential use of oxidative enzymes for the detoxification of organic pollutants. Appl. Catal., B 2003, 46, 1.
10. Barry, J. P.; Norwood, C.; Vouros, P. Detection and identification of benzo[a]pyrene diol epoxide adducts to DNA utilizing capillary eleotrophoresis eleotrospray mass spectrometry. Anal. Chem. 1996, 68, 1432.
11. Thurston, C. F. Structure and function of fungal laccases. Microbiology 1994, 140, 19.
12. Kersten, P. J.; Kalyanaraman, B.; Hammel, K. E.; Reinhammar, B.; Kirk, T. K. Comparison of lignin peroxidase, horseradish peroxidase and laccase in the oxidation of methoxybenzenes. Biochem. J. 1990, 268, 475.
13. Bourbonnais, R.; Paice, M. G.; Freiermuth, B.; Bodie, E.; Borneman, S. Reactivities of various mediators and laccases with kraft pulp and lignin model compounds. Appl. Environ. Microbiol. 1997, 63, 4627.
14. Collins, P. J.; Kotterman, M. J. J.; Field, J. A.; Dobson, A. D. W. Oxidation of anthracene and benzo[a]pyrene by laccases from Trametes versicolor. Appl. Environ. Microbiol. 1996, 62, 4563.
15. Majcherczyk, A.; Johannes, C.; Hüttermann, A. Oxidation of polycyclic aromatic hydrocarbons (PAH) by laccase of Trametes versicolor. Enzyme Microb. Technol. 1998, 22, 335.
16. Kirk, T. K.; Farrell, R. L. Enzymatic "combustion": The microbial degradation of lignin. Annu. Rev. Microbiol. 1987, 41, 465.
17. Camarero, S.; Ibarra, D.; Martínez, M. J.; Martínez, A. T. Lignin-derived compounds as efficient laccase mediators for decolorization of different types of recalcitrant dyes. Appl. Environ. Microbiol. 2005, 71, 1775.
18. Lam, T. B. T.; Iiyama, K.; Stone, B. A. Determination of etherified hydroxycinnamic acids in cell walls of grasses. Phytochemistry 1994, 36, 773.
19. Herpoël, I.; Moukha, S.; Lesage-Meessen, L.; Sigoillot, J. C.; Asther, M. Selection of Pycnoporus cinnabarinus strains for laccase production. FEMS Microbiol. Lett. 2000, 183, 301.
20. Alcalde, M.; Bulter, T.; Arnold, F. H. Colorimetric assays for biodegradation of polycyclic aromatic hydrocarbons by fungal laccases. J. Biomol. Screen. 2002, 7, 547.
21. Johannes, C.; Majcherczyk, A. Natural mediators in the oxidation of polycyclic aromatic hydrocarbons by laccase mediator systems. Appl. Environ. Microbiol. 2000, 66, 524.
22. Cajthaml, T.; Moder, M.; Kacer, P.; Sasek, V.; Popp, P. Study of fungal degradation products of polycyclic aromatic hydrocarbons using gas chromatography with ion trap mass spectrometry detection. J. Chromatogr., A 2002, 974, 213.
23. Baborova, P.; Moder, M.; Baldrian, P.; Cajthamlova, K.; Cajthaml, T. Purification of a new manganese peroxidase of the white-rot fungus Irpex lacteus, and degradation of polycyclic aromatic hydrocarbons by the enzyme. Res. Microbiol. 2006, 157, 248.
24. Vázquez-Duhalt, R.; Westlake, D. W. S.; Fedorak, P. M. Lignin peroxidase oxidation of aromatic compounds in systems containing organic solvents. Appl. Environ. Microbiol. 1994, 60, 459.
25. Eibes, G.; Cajthaml, T.; Moreira, M. T.; Feijoo, G.; Lema, J. M. Enzymatic degradation of anthracene, dibenzothiophene and pyrene by manganese peroxidase in media containing acetone. Chemosphere 2006, 64, 408.
26. Jeftic, L.; Adams, R. N. Electrochemical Oxidation Pathways of Benzo (A) Pyrene. Abstracts Pap. Am. Chem. Soc. 1969, AN75-&.
27. Rama, R.; Mougin, C.; Boyer, F. D.; Kollmann, A.; Malosse, C.; Sigoillot, J. C. Biotransformation of benzo[a]pyrene in bench scale reactor using laccase of Pycnoporus cinnabarinus. Biotechnol. Lett. 1998, 20, 1101.
28. Steffen, K. T.; Hatakka, A.; Hofrichter, M. Degradation of benzo[a]pyrene by the litter-decomposing basidiomycete Stropharia coronilla: Role of manganese peroxidase. Appl. Environ. Microbiol. 2003, 69, 3957.
29. Chen, C. L.; Potthast, A.; Rosenau, T.; Gratzl, J. S.; Kirkman, A. G.; Nagai, D.; Miyakoshi, T. Laccase-catalyzed oxidation of 1-(3,4-dimethoxyphenyl)- 1-propene using ABTS as mediator. J. Mol. Catal. B: Enzym. 2000, 8, 213.
30. Cantarella, G.; Galli, C.; Gentili, P. Free radical versus electron-transfer routes of oxidation of hydrocarbons by laccase-mediator systems. Catalytic and stoichiometric procedures. J. Mol. Catal. B: Enzym. 2003, 22, 135.
31. Marzullo, L.; Cannio, R.; Giardina, P.; Santini, M. T.; Sannia, G. Veratryl alcohol oxidase from Pleurotus ostreatus participates in lignin biodegradation and prevents polymerization of laccase-oxidized substrates. J. Biol. Chem. 1995, 270, 3823.
32. d'Acunzo, F.; Galli, C. First evidence of catalytic mediation by phenolic compounds in the laccase-induced oxidation of lignin models. Eur. J. Biochem. 2003, 270, 3634.
33. Daquino, C.; Foti, M. C. Coupling and fast decarboxylation of aryloxyl radicals of 4-hydroxycinnamic acids with formation of stable p-quinomethanes. Tetrahedron 2006, 62, 1536.
34. Claus, H. Laccases: structure, reactions, distribution. Micron 2004, 35, 93.
35. Terrón, M. C.; González, T.; Carbajo, J. M.; Yagüe, S.; Arana-Cuenca, A.; Téllez, A.; Dobson, A. D.; González, A. E. Structural close-related aromatic compounds have different effects on laccase activity and on lcc gene expression in the ligninolytic fungus Trametes sp. I-62. Fungal Genet. Biol. 2004, 41, 954.
36. Kuiters, A. T.; Denneman, C. A. J. Water-soluble phenolic substances in soils under several coniferous and deciduous tree species. Soil Biol. Biochem. 1987, 19, 765.
37. Felbeck, G. T. Structural hypotheses of soil humic acids. Soil Sci. 1971, 111, 42-&.
38. Djurdjevic, L.; Mitrovic, M.; Pavlovic, P.; Gajic, G.; Kostic, O. Phenolic acids as bioindicators of fly ash deposit revegetation. Arch. Environ. Contam. Toxicol. 2006, 50, 488.
39. Suominen, K.; Kitunen, V.; Smolander, A. Characteristics of dissolved organic matter and phenolic compounds in forest soils under silver birch (Betula pendula), Norway spruce (Picea abies) and Scots pine (Pinus sylvestris). Eur. J. Soil Sci. 2003, 54, 287.
40. Fan, X.; Deng, Y. Separation and identification of aromatic acids in soil and the Everglades sediment samples using solid-phase microextraction followed by capillary zone electrophoresis. J. Chromatogr. 2002, 979, 417.
41. Munzenberger, B.; Heilemann, J.; Strack, D.; Kottke, I.; Oberwinkler, F. Phenolics of mycorrhizas and nonmycorrhizal roots of Norway spruce. Planta 1990, 182, 142.
42. Tatsumi, K.; Wada, S.; Ichikawa, H.; Liu, S. Y.; Bollag, J. M. Cross-Coupling of a Chloroaniline and Phenolic Acids Catalyzed by a Fungal Enzyme. Water Sci. Technol. 1992, 26, 2157.
43. Bollag, J. M. Decontaminating Soil with Enzymes. Environ. Sci. Technol. 1992, 26, 1876.
44. Gianfreda, L.; Rao, M. A. Potential of extracellular enzymes in remediation of polluted soils: a review. Enzyme Microb. Technol. 2004, 35, 339.