Biodegradation of endocrine-disrupting compounds by ligninolytic fungi: Mechanisms involved in the degradation

Environmental Microbiology

Volumn 17, Issue 12, 2015, Pages 4822-4834

  Cajthaml, Tomáš ^a,b  

^a INSTITUTE OF MICROBIOLOGY   (Czech Republic)

^b CHARLES UNIVERSITY   (Czech Republic)

Author keywords

[No Author keywords available]

Indexed keywords

4,4' ISOPROPYLIDENEDIPHENOL; BENZHYDRYL DERIVATIVE; ENDOCRINE DISRUPTOR; ESTROGEN; LIGNIN; NONYLPHENOL; PHENOL DERIVATIVE; POLLUTANT; POLYCHLORINATED BIPHENYL;

BIOREMEDIATION; FUNGUS; HUMAN; METABOLISM; POLLUTANT; TOXICITY;

BENZHYDRYL COMPOUNDS; BIODEGRADATION, ENVIRONMENTAL; ENDOCRINE DISRUPTORS; ENVIRONMENTAL POLLUTANTS; ESTROGENS, NON-STEROIDAL; FUNGI; HUMANS; LIGNIN; PHENOLS; POLYCHLORINATED BIPHENYLS;

EID: 84955689215     PISSN: 14622912     EISSN: 14622920     Source Type: Journal    
DOI: 10.1111/1462-2920.12460     Document Type: Short Survey

References (98)

1. Adebusoye, S.A., Picardal, F.W., Ilori, M.O., and Amund, O.O. (2008) Influence of chlorobenzoic acids on the growth and degradation potentials of PCB-degrading microorganisms. World J Microbiol Biotechnol 24: 1203-1208.
2. Alexander, M. (1994) Biodegradation and Bioremediation. San Diego, CA, USA: Academic Press.
3. Auriol, M., Filali-Meknassia, Y., Tyagi, R.D., and Adams, C.D. (2007) Laccase-catalyzed conversion of natural and synthetic hormones from a municipal wastewater. Water Res 41: 3281-3288.
4. Baldrian, P. (2006) Fungal laccases - occurrence and properties. FEMS Microbiol Rev 30: 215-242.
5. Blánquez, P., and Guieysse, B. (2008) Continuous biodegradation of 17β-estradiol and 17α-ethynylestradiol by Trametes versicolor. J Hazard Mater 50: 459-462.
6. Cabana, H., Jiwan, J.L.H., Rozenberg, R., Elisashvili, V., Penninckx, M., Agathos, S.N., and Jones, J.P. (2007a) Elimination of endocrine disrupting chemicals nonylphenol and bisphenol A and personal care product ingredient triclosan using enzyme preparation from the white rot fungus Coriolopsis polyzona. Chemosphere 67: 770-778.
7. Cabana, H., Jones, J.P., and Agathos, S.N. (2007b) Elimination of endocrine disrupting chemicals using white rot fungi and their lignin modifying enzymes: a review. Eng Life Sci 7: 429-456.
8. Cajthaml, T., and Svobodová, K. (2012) Biodegradation of aromatic pollutants by ligninolytic fungal strains. In Microbial Degradation of Xenobiotics. Singh, S.N. (ed.). Berlin, Germany: Springer-Verlag, pp. 291-316.
9. Cajthaml, T., Křesinová, Z., Svobodová, K., and Möder, M. (2009a) Biodegradation of endocrine disrupting compounds and suppression of estrogenic activity by ligninolytic fungi. Chemosphere 6: 745-750.
10. Cajthaml, T., Křesinová, Z., Svobodová, K., Sigler, K., and Řezanka, T. (2009b) Microbial transformation of synthetic estrogen 17α-ethinylestradiol. Environ Pollut 157: 3325-3335.
11. Cañas, A.I., and Camarero, S. (2010) Laccases and their natural mediators: biotechnological tools for sustainable eco-friendly processes. Biotechnol Adv 28: 694-705.
12. CEC (Commission of the European Communities) (2001). The implementation of the community strategy for endocrine disrupters: a range of substances suspected of interfering with the hormone systems of humans and wild life. Communication from the Commission to the Council and the European Parliament, Brussels, COM (2001) 262.
13. Choudhary, M.I., Musharraf, S.G., Ali, R.A., Atif, M., and Atta-ur-Rahman (2004) Microbial transformation of antifertility agents, norethisterone and 17α-ethinylestradiol. Z Naturforschung 59b: 319-323.
14. Clouzot, L., Marrot, B., Doumenq, P., and Roche, N. (2008) 17α-Ethinylestradiol: an endocrine disrupter of great concern. Analytical methods and removal processes applied to water purification. A review. Environ Prog 27: 383-396.
15. Corvini, P.F.X., Schaffer, A., and Schlosser, D. (2006) Microbial degradation of nonylphenol and other alkylphenols - our evolving view. Appl Microbiol Biotechnol 72: 223-243.
16. Čvančarová, M., Křesinová, Z., Filipová, A., Covino, S., and Cajthaml, T. (2012) Biodegradation of PCBs by ligninolytic fungi and characterization of the degradation products. Chemosphere 88: 1317-1323.
17. Dec, J., Haider, K., and Bollag, J. (2003) Release of substituents from phenolic compounds during oxidative coupling reactions. Chemosphere 52: 549-556.
18. Della Greca, M., Pinto, G., Pistillo, P., Pollio, A., Previtera, L., and Temussi, F. (2008) Biotransformation of ethinylestradiol by microalgae. Chemosphere 70: 2047-2053.
19. Demarche, P., Junghanns, C.H., Nair, R.R., and Agathos, S.N. (2012) Harnessing the power of enzymes for environmental stewardship. Biotechnol Adv 30: 933-953.
20. Dietrich, D., Hickey, W.J., and Lamar, R. (1995) Degradation of 4, 40-dichlorobiphenyl, 3, 30, 4, 40-tetrachlorobiphenyl, and 2, 20, 4, 40, 5, 50-hexachlorobiphenyl by the white-rot fungus Phanerochaete chrysosporium. Appl Environ Microbiol 61: 3904-3909.
21. Dubroca, J., Brault, A., Kollmann, A., Touton, I., Jolivalt, G., Kerhoas, L., and Mougin, C. (2005) Biotransformation of nonylphenol surfactants in soils amended with contaminated sewage sludges. In Environmental Chemistry: Green Chemistry and Pollutants in Ecosystems. Lichtfouse, E., Dudd, S., and Robert, D. (eds). Berlin, Germany: Springer, pp. 305-315.
22. Eaton, D.C. (1985) Mineralization of polychlorinated biphenyls by Phanerochaete chrysosporium: a ligninolytic fungus. Enzyme Microb Technol 7: 194-196.
23. Field, J.A., and Sierra-Alvarez, R. (2008) Microbial transformation and degradation of polychlorinated biphenyls. Environ Pollut 155: 1-12.
24. Floudas, D., Binder, M., Riley, R., Barry, K., Blanchette, R.A., Henrissat, B., etal. (2012) The paleozoic origin of enzymatic lignin decomposition reconstructed from 31 fungal genomes. Science 336: 1715-1718.
25. Fukuda, T., Uchida, H., Takashima, Y., Uwajima, T., Kawabata, T., and Suzuki, M. (2001) Degradation of bisphenol A by purified laccase from Trametes villosa. Biochem Biophys Res Commun 284: 704-706.
26. Fukuda, T., Uchida, H., Suzuki, M., Miyamoto, H., Morinaga, H., Nawata, H., and Uwajima, T. (2004) Transformation products of bisphenol A by a recombinant Trametes villosa laccase and their estrogenic activity. J Chem Technol Biotechnol 79: 1212-1218.
27. Furukawa, K., and Fujihara, H. (2008) Microbial degradation of polychlorinated biphenyls. Biochemical and molecular features. J Biosci Bioeng 105: 433-449.
28. Furuno, S., Foss, S., Wild, E., Jones, K.C., Semple, K.T., Harms, H., and Wick, L.W. (2012) Mycelia promote active transport and spatial dispersion of polycyclic aromatic hydrocarbons. Environ Sci Technol 46: 5463-5470.
29. Gregoraszczuk, E.L., and Ptak, A. (2013) Endocrine-disrupting chemicals: some actions of POPs on female reproduction. Int J Endocrinol 2013: 1-9. Article ID 828532.
30. Hernandez-Ortega, A., Ferreira, P., and Martinez, A.T. (2012) Fungal aryl-alcohol oxidase: a peroxide-producing flavoenzyme involved in lignin degradation. Appl Microbiol Biotechnol 93: 1395-1410.
31. Hirano, T., Honda, Y., Watanabe, T., and Kuwahara, M. (2000) Degradation of bisphenol A by the lignin-degrading enzyme, manganese peroxidase, produced by the white-rot basidiomycete, Pleurotus ostreatus. Biosci Biotechnol Biochem 64: 1958-1962.
32. Hirosue, S., Tazaki, M., Hiratsuka, N., Yanai, S., Kabumoto, H., Shinkyo, R., etal. (2011) Insight into functional diversity of cytochrome P450 in the white-rot basidiomycete Phanerochaete chrysosporium: involvement of versatile monooxygenase. Biochem Biophys Res Commun 407: 118-123.
33. Hofrichter, M. (2002) Review: lignin conversion by manganese peroxidase (MnP). Enzyme Microb Technol 30: 454-466.
34. Hofrichter, M., Scheibner, K., Schneegar, J., and Fritsche, W. (1999) Enzymatic combustion of aromatic and aliphatic compounds by manganese peroxidase from Nematoloma frowardii. Appl Environ Microbiol 64: 399-404.
35. Hua, F., Wang, H.Q., Li, Y., and Zhao, Y.C. (2013) Trans-membrane transport of n-octadecane by Pseudomonas sp. DG17. J Microbiol 51: 791-799.
36. Huang, Q., Walter, J., and Weber, J.R. (2005) Transformation and removal of bisphenol A from aqueous phase via peroxidase-mediated oxidative coupling reactions: efficacy, products, and pathways. Environ Sci Technol 39: 6029-6036.
37. Husain, M., and Husain, Q. (2008) Applications of redox mediators in the treatment of organic pollutants by using oxidoreductive enzymes: a review. Crit Rev Biotechnol 38: 1-42.
38. Husain, Q., Husain, M., and Kulshrestha, Y. (2009) Remediation and treatment of organopollutants mediated by peroxidases: a review. Crit Rev Biotechnol 29: 94-119.
39. Junghanns, C., Moeder, M., Krauss, G., Martin, C., and Schlosser, D. (2005) Degradation of the xenoestrogen nonylphenol by aquatic fungi and their laccases. Microbiology 151: 45-57.
40. Kabiersch, G., Rajasarkka, J., Tuomela, M., Hatakka, A., Virta, M., and Steffen, K. (2013) Bioluminescent yeast assay for detection of organotin compounds. Anal Chem 85: 5740-5745.
41. Kamei, I., Kogura, R., and Kondo, R. (2006a) Metabolism of 4, 4′-dichlorobiphenyl by white-rot fungi Phanerochaete chrysosporium and Phanerochaete sp MZ142. Appl Microbiol Biotechnol 72: 566-575.
42. Kamei, I., Sonoki, S., Haraguchi, K., and Kondo, R. (2006b) Fungal bioconversion of toxic polychlorinated biphenyls by white-rot fungus, Phlebia brevispora. Appl Microbiol Biotechnol 73: 932-940.
43. Kang, J.-H., Yoshiki, K., and Fusao, K. (2006) Biodegradation or metabolism of bisphenol A: from microorganisms to mammals. Toxicology 217: 81-90.
44. Kobayashi, K., Katayama-Hirayama, K., and Tobita, S. (1996) Isolation and characterization of microorganisms that degrade 4-chlorobiphenyl to 4-chlorobenzoic acid. J Gen Appl Microbiol 42: 401-410.
45. Kojima, H., Takeuchi, S., and Nagai, T. (2010) Endocrine-disrupting potential of pesticides via nuclear receptors and aryl hydrocarbon receptor. J Health Sci 56: 374-386.
46. Kolvenbach, B., Schlaich, N., Raoui, Z., Prell, J., Zuhlke, S., Schaffer, A., etal. (2007) Degradation pathway of bisphenol A: does ipso substitution apply to phenols containing a quaternary alpha-carbon structure in the para position? Appl Environ Microbiol 73: 4776-4784.
47. Krčmář, P., Kubátová, A., Votruba, J., Erbanová, P., Novotný, C., and Šašek, V. (1999) Degradation of polychlorinated biphenyls by extracellular enzymes of Phanerochaete chrysosporium produced in a perforated plate bioreactor. World J Microbiol Biotechnol 15: 269-276.
48. Křesinová, Z., Svobodová, K., and Cajthaml, T. (2009) Microbial degradation of endocrine disrupting compounds. Chem Listy 103: 200-207.
49. Křesinová, Z., Moeder, M., Ezechiáš, M., Svobodová, K., and Cajthaml, T. (2012) Mechanistic study of 17α-ethinylestradiol biodegradation by Pleurotus ostreatus: tracking of extracelullar and intracelullar degradation mechanisms. Environ Sci Technol 46: 13377-13385.
50. Kurniawati, S., and Nicell, J.A. (2007) Efficacy of mediators for enhancing the laccase-catalyzed oxidation of aqueous phenol. Enzyme Microb Technol 41: 353-361.
51. Leskinen, P., Michaelini, E., Pikard, D., Karp, M., and Virta, M. (2005) Bioluminescent yeast assays for detecting estrogenic and androgeni activity in different matrices. Chemosphere 61: 259-266.
52. Lloret, L., Eibes, G., Lú-Chau, T.A., Moreira, M.T., Feijoo, G., and Lema, J.M. (2010) Laccase-catalyzed degradation of anti-inflammatories and estrogens. Biochem Eng J 51: 124-131.
53. Lloret, L., Eibes, G., Moreira, M.T., Feijoo, G., and Lema, J.M. (2013) Removal of estrogenic compounds from filtered secondary wastewater effluent in a continuous enzymatic membrane reactor. Identification of biotransformation products. Environ Sci Technol 47: 4536-4543.
54. McKinlay, R., Plant, J.A., Bell, J.N.B., and Voulvoulis, N. (2008) Endocrine disrupting pesticides: implications for risk assessment. Environ Int 34: 168-183.
55. Maffini, M.V., Rubin, B.S., Sonnenschein, C., and Soto, A.M. (2006) Endocrine disruptors and reproductive health: the case of bisphenol-A. Mol Cell Endocrinol 254-255: 179-186.
56. Majeau, J.-A., Satinder, K.B., and Rajeshwar, D.T. (2010) Laccases for removal of recalcitrant and emerging pollutants. Bioresour Technol 101: 2331-2350.
57. Martínez, Á.T., Speranza, M., Ruiz-Dueñas, F.J., Ferreira, P., Camarero, S., Guillén, F., etal. (2005) Biodegradation of lignocellulosics: microbial, chemical, and enzymatic aspects of the fungal attack of lignin. Int Microbiol 8: 195-204.
58. Martinez, D., Larrondo, L.F., Putnam, N., Sollewijn Gelpke, M.D., Huang, K., Chapman, J., etal. (2004) Genome sequence of the lignocellulose degrading fungus Phanerochaete chrysosporium strain RP78. Nat Biotechnol 22: 695-700.
59. Matozzo, V., Gagné, F., Marin, M.G., Ricciardi, F., and Blaise, C. (2008) Vitellogenin as a biomarker of exposure to estrogenic compounds in aquatic invertebrates: a review. Environ Int 34: 531-545.
60. Matsuzaki, F., and Wariishi, H. (2005) Molecular characterization of cytochrome P450 catalyzing hydroxylation of benzoates from the white-rot fungus Phanerochaete chrysosporium. Biochem Biophys Res Commun 334: 1184-1190.
61. Michizoe, J., Ichinose, H., Kamila, N., Maruyama, T., and Goto, M. (2005) Biodegradation of phenolic environmental pollutants by a surfactant-laccase complex in organic media. J Biosci Bioeng 99: 642-647.
62. Moeder, M., Cajthaml, T., Schrader, S., and Šašek, V. (2002) Solid phase microextraction (SPME) used for direct fruit-body sampling in comparison with ASE-GC-MS to describe PAH partition in mushroom cultures. Fresenius Environ Bull 11: 1-5.
63. Moeder, M., Cajthaml, T., Keller, G., Erbanová, P., and Šašek, V. (2005) Structure selectivity in degradation and translocation of polychlorinated biphenyls (Delor 103) with a Pleurotus ostreatus culture. Chemosphere 61: 1370-1378.
64. Murugesan, K., Chang, Y.Y., Kim, Y.M., Jong-Rok, J., Kim, E.J., and Chang, Y.S. (2010) Enhanced transformation of triclosan by laccase in the presence of redox mediators. Water Res 44: 298-308.
65. Muzikář, M., Křesinová, Z., Svobodová, K., Filipová, A., Čvančarová, M., Cajthamlová, K., and Cajthaml, T. (2011) Biodegradation of chlorobenzoic acids by ligninolytic fungi. J Hazard Mater 196: 386-394.
66. Nicotra, S., Intra, A., Ottolina, G., Riva, S., and Danieli, B. (2004) Laccase-mediated oxidation of the steroid hormone 17b-estradiol in organic solvents. Tetrahedron Asymmetry 15: 2927-2931.
67. Pointing, S.B. (2001) Feasibility of bioremediation by white-rot fungi. Appl Microbiol Biotechnol 57: 20-33.
68. Routledge, E.J., and Sumpter, J.P. (1996) Estrogenic activity of surfactants and some of their degradation products assessed using a recombinant yeast screen. Environ Toxicol Chem 15: 241-248.
69. Rozalska, S., Szewczyk, R., and Dlugonski, J. (2010) Biodegradation of 4-n-nonylphenol by the non-ligninolytic filamentous fungus Gliocephalotrichum simplex: a proposal of a metabolic pathway. J Hazard Mater 180: 323-331.
70. Ruiz-Dueñas, F.J., and Martínez, Á.T. (2009) Microbial degradation of lignin: how a bulky recalcitrant polymer is efficiently recycled in nature and how we can take advantage of this. Microb Biotechnol 2: 164-177.
71. Sasaki, M., Maki, J.I., Oshiman, K.I., Matsumura, Y., and Tsuchido, T. (2005) Biodegradation of bisphenol A by cells and cell lysate from Sphingomonas sp. strain AO1. Biodegradation 16: 449-459.
72. Shary, S., Kapich, A.N., Panisko, E.A., Magnuson, J.K., Cullen, D., and Hammel, K.E. (2008) Differential expression in Phanerochaete chrysosporium of membrane-associated proteins relevant to lignin degradation. Appl Environ Microbiol 74: 7252-7257.
73. Shimizu, M., Kobayashi, Y., Tahala, H., and Wariishi, H. (2005) Transportation mechanism for vanillin uptake through fungal plasma membrane. Appl Microbiol Biotechnol 68: 673-679.
74. Shiraishi, F., Okumura, T., Nomachi, M., Serizawa, S., Nishikawa, J., Edmonds, J.S., etal. (2003) Estrogenic and thyroid hormone activity of a series of hydroxy-polychlorinated biphenyls. Chemosphere 52: 33-42.
75. Silva, C.P., Otero, M., and Esteves, V. (2012) Processes for the elimination of estrogenic steroid hormones from water: a review. Environ Pollut 165: 38-58.
76. Soto, A.M., Justicia, H., Sraz, J.W., and Sonnenschein, C. (1991) P-nonylphenol: an estrogenic xenobiotic released from modified polystyrene. Environ Health Perspect 92: 167-173.
77. Stella, T., Covino, S., Křesinová, Z., D'Annibale, A., Petruccioli, M., Čvančarová, M., and Cajthaml, T. (2013) Chlorobenzoic acid degradation by Lentinus (Panus) tigrinus: in vivo and in vitro mechanistic study-evidence for P-450 involvement in the transformation. J Hazard Mater 260: 975-983.
78. Subramanian, V., and Yadav, J.S. (2009) Role of P450 monooxygenases in the degradation of the endocrine-disrupting chemical nonylphenol by the white rot fungus Phanerochaete chrysosporium. Appl Environ Microbiol 75: 5570-5580.
79. Suzuki, K., Hirai, H., Murata, H., and Nishida, T. (2003) Removal of estrogenic activities of 17α-estradiol and ethinylestradiol by ligninolytic enzymes from white rot fungi. Water Res 37: 1972-1975.
80. Svobodová, K., and Cajthaml, T. (2010) New in vitro reporter gene bioassays for screening of hormonal active compounds in the environment. Appl Microbiol Biotechnol 88: 839-847.
81. Svobodová, K., Plačková, M., Novotná, V., and Cajthaml, T. (2009) Estrogenic and androgenic activity of PCBs, their chlorinated metabolites and other endocrine disruptors estimated with two in vitro yeast assays. Sci Total Environ 407: 5921-5925.
82. Syed, K., Porollo, A., Ying, W.L., and Yadav, J.S. (2011) A fungal P450 (CYP5136A3) capable of oxidizing polycyclic aromatic hydrocarbons and endocrine disrupting alkylphenols: role of Trp129 and Leu324. PLoS ONE 6: 1-14.
83. Syed, K., Porollo, A., Lam, Y.W., Grimmett, P.E., Yadav, J.S., and Jagjit, S. (2013) CYP63A2, a catalytically versatile fungal P450 monooxygenase capable of oxidizing higher-molecular-weight polycyclic aromatic hydrocarbons, alkylphenols, and alkanes. Appl Environ Microbiol 79: 2692-2702.
84. Takagi, S., Shirota, C., Sakaguchi, K., Suzuki, J., Sue, T., Nagasaka, H., etal. (2007) Exoenzymes of Trametes versicolor can metabolize coplanar PCB congeners and hydroxy PCB. Chemosphere 67: S54-S57.
85. Tanaka, T., Tonosaki, T., Nose, M., Tomidokoro, N., Kadomura, N., Fujii, T., and Taniguchi, M. (2001) Treatment of model soils contaminated with phenolic endocrine-disrupting chemicals with laccase from Trametes sp. in a rotating reactor. J Biosci Bioeng 92: 312-316.
86. Tanaka, T., Tamura, T., Ishizaki, Y., Kawasaki, A., Kawase, T., Teraguchi, M., and Taniguchi, M. (2009) Enzymatic treatment of estrogens and estrogen glucuronide. J Environ Sci (China) 21: 731-735.
87. Torres-Duarte, C., Teresa, V.M., and Vazquez-Duhalt, R. (2012) Laccase-mediated transformations of endocrine disrupting chemicals abolish binding affinities to estrogen receptors and their estrogenic activity in zebrafish. Appl Biochem Biotechnol 168: 864-876.
88. Tran, N.H., Urase, T., Ngo, H.H., Hu, J.Y., and Ong, S.L. (2013) Insight into metabolic and cometabolic activities of autotrophic and heterotrophic microorganisms in the biodegradation of emerging trace organic contaminants. Bioresour Technol 146: 721-731.
89. Tsutsumi, Y., Haneda, T., and Nishida, T. (2001) Removal of estrogenic activities of bisphenol A and nonylphenol by oxidative enzymes from lignin-degrading Basidiomycetes. Chemosphere 42: 271-276.
90. Tyler, C.R., and Routledge, E.J. (1998) Oestrogenic effects in fish in English rivers with evidence of their causation. Pure Appl Chem 70: 1795-1804.
91. Vallini, G., Frassinetti, S., D'Andrea, F., Catelani, G., and Agnolucci, M. (2001) Biodegradation of 4-(1-nonyl)phenol by axenic cultures of the yeast Candida aquaetextoris: identification of microbial breakdown products and proposal of a possible metabolic pathway. Int Biodeterior Biodegradation 47: 133-140.
92. Verdin, A., Lounès-Hadj Sahraoui, A., Laruelle, F., Grandmougin-Ferjani, A., and Furane, R. (2006) Effect of the high polycyclic aromatic hydrocarbon, benzo[a]pyrene, on the lipid content of Fusarium solani. Mycol Res 110: 479-484.
93. Wang, J., Majima, N., Hirai, H., and Kawagishi, H. (2012) Effective removal of endocrine-disrupting compounds by lignin peroxidase from the white-rot fungus Phanerochaete sordida YK-624. Curr Microbiol 64: 300-303.
94. Wang, J., Yamamoto, Y., Hirai, H., and Kawagishi, H. (2013a) Dimerization of bisphenol by hyper lignin-degrading fungus Phanerochaete sordida YK-624 under ligninolytic condition. Curr Microbiol 66: 544-547.
95. Wang, J., Yamamoto, R., Yamamoto, Y., Tokumoto, T., Dong, J., Thomas, P., etal. (2013b) Hydroxylation of bisphenol A by hyper lignin-degrading fungus Phanerochaete sordida YK-624 under non-ligninolytic condition. Chemosphere 93: 1419-1423.
96. Wong, D.W.S. (2009) Structure and action mechanism of ligninolytic enzymes. Appl Biochem Biotechnol 157: 174-209.
97. Yamamoto, T., Yasuhara, A., Shiraishi, H., and Nakasugi, O. (2001) Bisphenol A in hazardous waste landfill leachates. Chemosphere 42: 415-418.
98. Ying, G.G., Williams, B., and Kookana, R. (2002) Environmental fate of alkylphenols and alkylphenol ethoxylates - a review. Environ Int 28: 215-226.