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Dimerization of Bisphenol A by Hyper Lignin-Degrading Fungus Phanerochaete sordida YK-624 Under Ligninolytic Condition

Current Microbiology volume 66, pages 544–547 (2013)Cite this article

Abstract

Bisphenol A (BPA) was treated with hyper lignin-degrading fungus Phanerochaete sordida YK-624 under ligninolytic condition. After preculturing P. sordida YK-624 for 4 days, BPA (final concentration, 1 and 0.1 mM) was added to cultures. Both 1- and 0.1-mM BPA were effectively decreased within a 24-h treatment and two metabolites were detected. Two metabolites (5,5′-bis-[1-(4-hydroxy-phenyl)1-methyl-ethyl]-biphenyl-2,2′-diol and 4-(2-(4-hydroxy-phenyl) propan-2-yl)-2-(4-(2-(4-hydroxyphenyl) propan-2-yl) phenoxy)phenol) were identified by ESI–MS and NMR analysis. These results indicated that BPA was oxidized to BPA phenoxy radicals by ligninolytic enzymes and then dimerized at extracellular region.

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References

  1. Campbell CG, Borglin SE, Green FB, Grayson A, Wozei E, Stringfellow WT (2006) Biologically directed environmental monitoring, fate, and transport of estrogenic endocrine disrupting compounds in water. Chemosphere 65:1265–1280

    PubMed  Article  CAS  Google Scholar 

  2. Matozzo V, Gagne F, Marin MG, Ricciardi F, Blaise C (2008) Vitellogenin as a biomarker of exposure to estrogenic compounds in aquatic invertebrates: a review. Environ Int 34:531–545

    PubMed  Article  CAS  Google Scholar 

  3. Brotons JA, Olea-Serrano MF, Villalobos M, Pedraza V, Olea N (1995) Xenoestrogens released from lacquer coatings in food cans. Environ Health Perspect 103:608–612

    PubMed  Article  CAS  Google Scholar 

  4. Olea N, Pulgar R, Pérez P, Olea-Serrano F, Rivas A, Novillo-Fertrell A, Pedraza V, Soto AM, Sonnenschein C (1996) Estrogenicity of resin-based composites and sealants used in dentistry. Environ Health Perspect 104:298–305

    PubMed  Article  CAS  Google Scholar 

  5. Ballesteros-Gómez A, Rubio S, Pérez-Bendito D (2009) Analytical methods for the determination of bisphenol A in food. J Chromatogr 1216:449–469

    Article  Google Scholar 

  6. Kitada Y, Kawahata H, Suzuki A, Oomori T (2008) Distribution of pesticides and bisphenol A in sediments collected from rivers adjacent to coral reefs. Chemosphere 71:2082–2090

    PubMed  Article  CAS  Google Scholar 

  7. Matsumura Y, Hosokawa C, Sasaki-Mori M, Akahira A, Fukunaga K, Ikeuchi T, Oshiman K, Tsuchido T (2009) Isolation and characterization of novel bisphenol-A—degrading bacteria from soils. Biocontrol Sci 14:161–169

    PubMed  Article  CAS  Google Scholar 

  8. Kirk TK, Farrell RL (1987) Enzymatic “combustion”: the microbial degradation of lignin. Annu Rev Microbiol 41:465–505

    PubMed  Article  CAS  Google Scholar 

  9. Wang J, Ogata M, Hirai H, Kawagishi H (2011) Detoxification of aflatoxin B1 by manganese peroxidase from the white-rot fungus Phanerochaete sordida YK-624. FEMS Microbiol Lett 314:164–169

    PubMed  Article  CAS  Google Scholar 

  10. Wang J, Hirai H, Kawagishi H (2012) Biotransformation of acetamiprid by the white-rot fungus Phanerochaete sordida YK-624. Appl Microbiol Biotechnol 59:1779–1785

    Google Scholar 

  11. Bezalel L, Hadar Y, Fu PP, Freeman JP, Cerniglia CE (1996) Initial Oxidation products in the metabolism of pyrene, anthracene, fluorene, and dibenzothiophene by the white rot fungus Pleurotus ostreatus. Appl Environ Microbiol 62:2554–2559

    PubMed  CAS  Google Scholar 

  12. Collins PJ, Kotterman M, Field JA, Dobson A (1996) Oxidation of anthracene and benzo[a]pyrene by laccases from Trametes versicolor. Appl Environ Microbiol 62:4563–4567

    PubMed  CAS  Google Scholar 

  13. Ollikka P, Alhonmäki K, Leppänen VM, Glumoff T, Raijola T, Suominen I (1993) Decolorization of azo, triphenyl methane, heterocyclic, and polymeric dyes by lignin peroxidase isoenzymes from Phanerochaete chrysosporium. Appl Environ Microbiol 59:4010–4016

    PubMed  CAS  Google Scholar 

  14. Hirano T, Honda Y, Watanabe T, 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

    PubMed  Article  CAS  Google Scholar 

  15. Saito T, Kato K, Yokogawa Y, Nishida M, Yamashita N (2004) Detoxification of bisphenol A and nonylphenol by purified extracellular laccase from a fungus isolated from soil. J Biosci Bioeng 98:64–66

    PubMed  CAS  Google Scholar 

  16. Suzuki K, Hirai H, Murata H, Nishida T (2003) Removal of estrogenic activities of 17β-estradiol and ethinylestradiol by ligninolytic enzymes from white rot fungi. Water Res 37:1972–1975

    PubMed  Article  CAS  Google Scholar 

  17. Tamagawa Y, Yamaki R, Hirai H, Kawai S, Nishida T (2006) Removal of estrogenic activity of natural steroidal hormone estrone by ligninolytic enzymes from white rot fungi. Chemosphere 65:97–101

    PubMed  Article  CAS  Google Scholar 

  18. Wang J, Majima N, Hirai H, 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

    PubMed  Article  CAS  Google Scholar 

  19. Chai W, Handa Y, Suzuki M, Saito M, Kato N, Horiuchi CA (2005) Biodegradation of bisphenol A by fungi. Appl Biochem Biotechnol 120:175–182

    PubMed  Article  CAS  Google Scholar 

  20. Shin EH, Choi HT, Song HG (2007) Biodegradation of endocrine-disrupting bisphenol A by white rot fungus Irpex lacteus. J Microbiol Biotechnol 17:1147–1151

    PubMed  CAS  Google Scholar 

  21. Hirai H, Kondo R, Sakai K (1994) Screening of lignin-degrading fungi and their ligninolytic enzyme activities during biological bleaching of kraft pulp. Mokuzai Gakkaishi 40:980–986

    CAS  Google Scholar 

  22. Tien M, Kirk TK (1988) Lignin peroxidase of Phanerochaete chrysosporium. Methods Enzymol 161B:238–249

    Article  Google Scholar 

  23. Tsutsumi Y, Haneda T, Nishida T (2001) Removal of estrogenic activities of bisphenol A and nonylphenol by oxidative enzymes from lignin-degrading basidiomycetes. Chemosphere 42:271–276

    PubMed  Article  CAS  Google Scholar 

  24. Nishihara T, Nishikawa J, Kanayama T, Dakeyama F, Saito K, Imagawa M, Takatori S, Kitagawa Y, Hori S, Utsumi H (2000) Estrogenic activities of 517 chemicals by yeast two-hybrid assay. J Health Sci 46:282–298

    Article  CAS  Google Scholar 

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Affiliations

  1. Graduate School of Science and Technology, Shizuoka University, 836 Ohya, Suruga-ku, Shizuoka, 422-8529, Japan

    Jianqiao Wang & Hirokazu Kawagishi

  2. Department of Applied Biological Chemistry, Faculty of Agriculture, Shizuoka University, 836 Ohya, Suruga-ku, Shizuoka, 422-8529, Japan

    Yotaro Yamamoto, Hirofumi Hirai & Hirokazu Kawagishi

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  1. Jianqiao Wang
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  2. Yotaro Yamamoto
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  3. Hirofumi Hirai
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  4. Hirokazu Kawagishi
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Correspondence to Hirofumi Hirai.

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Wang, J., Yamamoto, Y., Hirai, H. et al. Dimerization of Bisphenol A by Hyper Lignin-Degrading Fungus Phanerochaete sordida YK-624 Under Ligninolytic Condition. Curr Microbiol 66, 544–547 (2013). https://doi.org/10.1007/s00284-013-0310-0

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  • DOI: https://doi.org/10.1007/s00284-013-0310-0

Keywords

  • Aflatoxin
  • Estrogenic Activity
  • Lignin Peroxidase
  • Ligninolytic Enzyme
  • Phenoxy Radical