Hydroxylation of bisphenol A by hyper lignin-degrading fungus Phanerochaete sordida YK-624 under non-ligninolytic condition

Chemosphere

Volumn 93, Issue 7, 2013, Pages 1419-1423

  Wang, Jianqiao ^a   Yamamoto, Ryoko ^a   Yamamoto, Yotaro ^a   Tokumoto, Toshinobu ^a   Dong, Jing ^b   Thomas, Peter ^b   Hirai, Hirofumi ^a   Kawagishi, Hirokazu ^a  

^a SHIZUOKA UNIVERSITY   (Japan)

^b UNIVERSITY OF TEXAS AT AUSTIN   (United States)

Author keywords

Bisphenol A; Cytochrome P450; Hydroxylation; Phanerochaete sordida YK 624

Indexed keywords

BIODEGRADATION; ELECTROSPRAY IONIZATION; ENDOCRINE DISRUPTERS; HYDROXYLATION; LIGNIN; MASS SPECTROMETRY; METABOLITES; PHENOLS;

BIS-PHENOL A; CYTOCHROME P450; CYTOCHROME P450 INHIBITORS; ELECTROSPRAY IONIZATION MASS SPECTRA; ENDOCRINE DISRUPTING COMPOUND; ESTROGENIC ACTIVITIES; PHANEROCHAETE SORDIDA YK-624; REPRESENTATIVE COMPOUND;

ENDOCRINOLOGY;

4,4' ISOPROPYLIDENEDIPHENOL; BENZENE DERIVATIVE; CYTOCHROME P450; LIGNIN; PIPERONYL BUTOXIDE;

CYTOCHROME; FUNGUS; INCUBATION; IONIZATION; LIQUID; METABOLITE; NUCLEAR MAGNETIC RESONANCE;

ARTICLE; CONTROLLED STUDY; ELECTROSPRAY MASS SPECTROMETRY; ESTROGEN ACTIVITY; FUNGAL STRAIN; FUNGUS; HYDROXYLATION; LIQUID CULTURE; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; PHANEROCHAETE SORDIDA; PROTEIN FUNCTION;

FUNGI; PHANEROCHAETE SORDIDA;

BISPHENOL A; CYTOCHROME P450; HYDROXYLATION; PHANEROCHAETE SORDIDA YK-624;

BENZHYDRYL COMPOUNDS; BIODEGRADATION, ENVIRONMENTAL; ENDOCRINE DISRUPTORS; ENVIRONMENTAL POLLUTANTS; HYDROXYLATION; PHANEROCHAETE; PHENOLS;

EID: 84885869175     PISSN: 00456535     EISSN: 18791298     Source Type: Journal    
DOI: 10.1016/j.chemosphere.2013.07.026     Document Type: Article

References (36)

1. Ballesteros-Gómez A., Rubio S., Pérez-Bendito D. Analytical methods for the determination of bisphenol A in food. J. Chromatogr. A 2009, 1216:449-469.
2. Brotons J.A., Olea-Serrano M.F., Villalobos M., Pedraza V., Olea N. Xenoestrogens released from lacquer coatings in food cans. Environ. Health Persp. 1995, 103:608-612.
3. Bumpus J.A., Tien M., Wright D., Aust S.D. Oxidation of persistent environmental pollutants by a white rot fungus. Science 1985, 228:1434-1436.
4. Chai W., Handa Y., Suzuki M., Saito M., Kato N., Horiuchi C.A. Biodegradation of bisphenol A by fungi. Appl. Biochem. Biotechnol. 2005, 120:175-182.
5. Hamada H., Tomi R., Asada Y., Furuya T. Phytoremediation of bisphenol A by cultured suspension cells of Eucalyptus perriniana-regioselective hydroxylation and glycosylation. Tetrahedron Lett. 2002, 43:4087-4089.
6. Harries J.E., Sheahan D.A., Jobling S., Matthiessen P., Neall P., Routledge E.J., Rycroft R., Sumpter J.P., Tylor T. A survey of estrogenic activity in United Kingom inland waters. Environ. Toxicol. Chem. 1996, 15:1993-2002.
7. Hata T., Kawai S., Okamura H., Nishida T. Removal of diclofenac and mefenamic acid by the white rot fungus Phanerochaete sordida YK-624 and identification of their metabolites after fungal transformation. Biodegradation 2010, 21:681-689.
8. Hirai H., Kondo R., Sakai K. Screening of lignin-degrading fungi and their ligninolytic enzyme activities during biological bleaching of kraft pulp. Mokuzai Gakkaishi 1994, 40:980-986.
9. Hirano T., Honda Y., Watanabe T., Kuwahara M. Degradation of bisphenol A by the lignin-degrading enzyme, manganese peroxidase, produced by the white-rot basidiomycete, Pleurotus ostreatus. Biosci. Biotechnol. Biochem. 2000, 64:1958-1962.
10. Hiratsuka N., Wariishi H., Tanaka H. Degradation of diphenyl ether herbicides by the lignin-degrading basidiomycete Coriolus versicolor. Appl. Microbiol. Biotechnol. 2001, 57:563-571.
11. Joshi D.K., Gold M.H. Degradation of 2,4,5-trichlorophenol by the lignin-degrading basidiomycete Phanerochaete chrysosporium. Appl. Environ. Microbiol. 1993, 59:1779-1785.
12. Kamei I., Suhara H., Kondo R. Phylogenetical approach to isolation of white-rot fungi capable of degrading polychlorinated dibenzo-p-dioxin. Appl. Microbiol. Biotechnol. 2005, 69:358-366.
13. Kirk T.K., Farrell R.L. Enzymatic combustion: the microbial degradation of lignin. Annu. Rev. Microbiol. 1987, 41:465-505.
14. Kitada Y., Kawahata H., Suzuki A., Oomori T. Distribution of pesticides and bisphenol A in sediments collected from rivers adjacent to coral reefs. Chemosphere 2008, 71:2082-2090.
15. Krishnan A.V., Stathis P., Permuth S.F., Tokes L., Feldman D. Bisphenol-A: an estrogenic substance is released from polycarbonate flasks during autoclaving. Endocrinology 1993, 132:2279-2286.
16. Larsson D.G.J., Adolfsson-Erici M., Parkkonen J., Pettersson M., Berg A.H., Olsson P., Forlin L. Ethinyloestradiol - an undesired fish contraceptive?. Aquat. Toxicol. 1999, 45:91-97.
17. Matsumura Y., Hosokawa C., Sasaki-Mori M., Akahira A., Fukunaga K., Ikeuchi T., Oshiman K., Tsuchido T. Isolation and characterization of novel bisphenol-A-degrading bacteria from soils. Biocontrol Sci. 2009, 14:161-169.
18. Mori T., Kondo R. Oxidation of chlorinated dibenzo-p-dioxin and dibenzofuran by white-rot fungus. Phlebia lindtneri. FEMS Microbiol. Lett. 2002, 216:223-227.
19. Mori T., Kitano S., Kondo R. Biodegradation of chloronaphthalenes and polycyclic aromatic hydrocarbons by the white-rot fungus Phlebia lindtneri. Appl. Microbiol. Biotechnol. 2003, 61:380-383.
20. Nakagawa Y., Tayama S. Metabolism and cytotoxicity of bisphenol A and other bisphenols in isolated rat hepatocytes. Arch. Toxicol. 2000, 74:99-105.
21. Olea N., Pulgar R., Pérez P., Olea-Serrano F., Rivas A., Novillo-Fertrell A., Pedraza V., Soto A.M., Sonnenschein C. Estrogenicity of resin-based composites and sealants used in dentistry. Environ. Health Persp. 1996, 104:298-305.
22. Pritchett J.J., Kuester R.K., Sipes I.G. Metabolism of bisphenol a in primary cultured hepatocytes from mice, rats, and humans. Drug Metab. Dispos. 2002, 30:1180-1185.
23. Purdom C.E., Hardiman P.A., Bye V.J., Eno N.C., Tyler C.R., Sumpter J. Estrogenic effects of effluents from sewage treatment works. Chem. Ecol. 1994, 8:275-285.
24. Saito T., Kato K., Yokogawa Y., Nishida M., Yamashita N. Detoxification of bisphenol A and nonylphenol by purified extracellular laccase from a fungus isolated from soil. J. Biosci. Bioeng. 2004, 98:64-66.
25. Shin E.H., Choi H.T., Song H.G. Biodegradation of endocrine-disrupting bisphenol A by white rot fungus Irpex lacteus. J. Microbiol. Biotechnol. 2007, 17:1147-1151.
26. Suzuki K., Hirai H., Murata H., Nishida T. Removal of estrogenic activities of 17β-estradiol and ethinylestradiol by ligninolytic enzymes from white rot fungi. Water Res. 2003, 37:1972-1975.
27. Tamagawa Y., Yamaki R., Hirai H., Kawai S., Nishida T. Removal of estrogenic activity of natural steroidal hormone estrone by ligninolytic enzymes from white rot fungi. Chemosphere 2006, 65:97-101.
28. Thomas P., Dong J. Binding and activation of the seven-transmembrane estrogen receptor GPR30 by environmental estrogens: a potential novel mechanism of endocrine disruption. J. Steroid. Biochem. 2006, 102:175-179.
29. Tokumoto T., Tokumoto M., Thomas P. Interactions of diethylstilbestrol (DES) and DES analogs with membrane progestin receptor-alpha and the correlation with their nongenomic progestin activities. Endocrinology 2007, 148:3459-3467.
30. 1 by manganese peroxidase from the white-rot fungus Phanerochaete sordida YK-624. FEMS Microbiol. Lett. 2011, 314:164-169.
31. Wang J., Hirai H., Kawagishi H. Biotransformation of acetamiprid by the white-rot fungus Phanerochaete sordida YK-624. Appl. Microbiol. Biotechnol. 2012, 93:831-835.
32. Wang J., Majima N., Hirai H., Kawagishi H. Effective removal of endocrine-disrupting compounds by lignin peroxidase from the white-rot fungus Phanerochaete sordida YK-624. Curr. Microbiol. 2012, 64:300-303.
33. Wang J., Yamamoto Y., Hirai H., Kawagishi H. Dimerization of bisphenol A by hyper lignin-degrading fungus Phanerochaete sordida YK-624 under ligninolytic condition. Curr. Microbiol. 2013, 66:544-547.
34. Watanabe I., Harada K., Matsui T., Miyasaka H., Okuhata H., Tanaka S., Nakayama H., Kato K., Bamba T., Hirata K. Characterization of bisphenol A metabolites produced by Portulaca oleracea cv. by liquid chromatography coupled with tandem mass spectrometry. Biosci. Biotechnol. Biochem. 2012, 76:1015-1017.
35. Xiao P., Mori T., Kamei I., Kondo R. A novel metabolic pathway for biodegradation of DDT by the white rot fungi, Phlebia lindtneri and Phlebia brevispora. Biodegradation 2011, 22:859-867.
36. Yim S.H., Kim H.J., Lee I.S. Microbial metabolism of the environmental estrogen bisphenol A. Arch. Pharm. Res. 2003, 26:805-808.