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

Jianqiao Wang; Yuto Yamada; Akira Notake; Yasushi Todoroki; Toshinobu Tokumoto; Jing Dong; Peter Thomas; Hirofumi Hirai; Hirokazu Kawagishi

doi:10.1016/j.chemosphere.2014.01.029

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

Chemosphere. 2014 Aug:109:128-33. doi: 10.1016/j.chemosphere.2014.01.029. Epub 2014 Feb 26.

Authors

Jianqiao Wang¹, Yuto Yamada², Akira Notake², Yasushi Todoroki³, Toshinobu Tokumoto¹, Jing Dong⁴, Peter Thomas⁴, Hirofumi Hirai⁵, Hirokazu Kawagishi⁶

Affiliations

¹ Graduate School of Science and Technology, Shizuoka University, 836 Ohya, Suruga-ku, Shizuoka 422-8529, Japan.
² Graduate School of Agriculture, Shizuoka University, 836 Ohya, Suruga-ku, Shizuoka 422-8529, Japan.
³ Graduate School of Agriculture, Shizuoka University, 836 Ohya, Suruga-ku, Shizuoka 422-8529, Japan; Research Institute of Green Science and Technology, Shizuoka University, 836 Ohya, Suruga-ku, Shizuoka 422-8529, Japan.
⁴ Marine Science Institute, University of Texas at Austin, 750 Channel View Drive, Port Aransas, TX 78373, USA.
⁵ Graduate School of Agriculture, Shizuoka University, 836 Ohya, Suruga-ku, Shizuoka 422-8529, Japan; Research Institute of Green Science and Technology, Shizuoka University, 836 Ohya, Suruga-ku, Shizuoka 422-8529, Japan. Electronic address: ahhirai@ipc.shizuoka.ac.jp.
⁶ Graduate School of Science and Technology, Shizuoka University, 836 Ohya, Suruga-ku, Shizuoka 422-8529, Japan; Graduate School of Agriculture, Shizuoka University, 836 Ohya, Suruga-ku, Shizuoka 422-8529, Japan; Research Institute of Green Science and Technology, Shizuoka University, 836 Ohya, Suruga-ku, Shizuoka 422-8529, Japan.

PMID: 24582362
DOI: 10.1016/j.chemosphere.2014.01.029

Abstract

Recently, we reported the conversion of bisphenol A (BPA) to 4-(2-(4-hydroxyphenyl)propan-2-yl)benzene-1,2-diol (hydroxy-BPA) by hyper lignin-degrading fungus Phanerochaete sordida YK-624 under non-ligninolytic condition. In the present study, the metabolism of hydroxy-BPA by P. sordida YK-624 was demonstrated under non-ligninolytic condition. Under these conditions, approximately 66% of hydroxy-BPA was degraded after 7 d of incubation. High-resolution electrospray ionization mass spectra and nuclear magnetic resonance analyses of the metabolites isolated from the culture broth indicated that hydroxy-BPA was metabolized to 4-(2-(4-hydroxyphenyl)propan-2-yl)-2-methoxyphenol (methoxy-BPA) and to 4-(2-(3,4-dimethoxyphenyl)propan-2-yl)phenol (dimethoxy-BPA) by sequential methylation events. These metabolites showed reduced estrogenic activity compared to BPA. These results suggested that the hydroxy BPA is methylated to two low toxic-methylation metabolites.

Keywords: Bisphenol A; Estrogenic activity; Metabolic pathway; Phanerochaete sordida YK-624.

MeSH terms

Benzhydryl Compounds / analysis
Benzhydryl Compounds / chemistry
Benzhydryl Compounds / metabolism*
Cell Line
Endocrine Disruptors / analysis
Endocrine Disruptors / chemistry
Endocrine Disruptors / metabolism*
Humans
Lignin / metabolism
Magnetic Resonance Spectroscopy
Phanerochaete / metabolism*
Phenols / analysis
Phenols / chemistry
Phenols / metabolism*
Spectrometry, Mass, Electrospray Ionization

Substances

Benzhydryl Compounds
Endocrine Disruptors
Phenols
Lignin
bisphenol A