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Biotransformation and reduction of estrogenicity of bisphenol A by the biphenyl-degrading Cupriavidus basilensis

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Abstract

The biphenyl-degrading Gram-negative bacterium Cupriavidus basilensis (formerly Ralstonia sp.) SBUG 290 uses various aromatic compounds as carbon and energy sources and has a high capacity to transform bisphenol A (BPA), which is a hormonally active substance structurally related to biphenyl. Biphenyl-grown cells initially hydroxylated BPA and converted it to four additional products by using three different transformation pathways: (a) formation of multiple hydroxylated BPA, (b) ring fission, and (c) transamination followed by acetylation or dimerization. Products of the ring fission pathway were non-toxic and all five products exhibited a significantly reduced estrogenic activity compared to BPA. Cell cultivation with phenol and especially in nutrient broth (NB) resulted in a reduced biotransformation rate and lower product quantities, and NB-grown cells did not produce all five products in detectable amounts. Thus, the question arose whether enzymes of the biphenyl degradation pathway are involved in the transformation of BPA and was addressed by proteomic analyses.

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Acknowledgements

We thank Dr. Ute Lechner from the Martin-Luther-University of Halle-Wittenberg and the German Collection of Microorganisms and Cell Cultures Braunschweig (Leibniz Institute DSMZ) for the identification of the bacterial strain. We also thank Dirk Albrecht for supporting the mass spectrometry analysis of cytosolic proteins of C. basilensis. Furthermore, we are grateful to Gerhard Burchhardt for evaluation of sequence data of the bacterial strain. Furthermore, we would like to thank Jan Wesche for determination of DNA sequences coding the biphenyl degrading enzymes of the bacterial strain and Robert Jack for reviewing the manuscript. MKZ thanks the European Social Fund for financial support (Landesgraduiertenstipendium; Mecklenburg-Vorpommern, Germany).

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  1. Institute of Microbiology, Ernst-Moritz-Arndt-University of Greifswald, Friedrich-Ludwig-Jahn-Str. 15, 17487, Greifswald, Germany

    Marie-Katherin Zühlke, Rabea Schlüter, Annett Mikolasch, Daniela Zühlke, Henning Schindler, Ann-Kristin Henning, Heidi Frenzel, Elke Hammer, Katharina Riedel & Frieder Schauer

  2. Leibniz Institute of Plant Genetics and Crop Plant Research, Corrensstr. 3, OT Gatersleben, 06466, Seeland, Germany

    Martin Giersberg & Gotthard Kunze

  3. Institute of Biochemistry, Ernst-Moritz-Arndt-University of Greifswald, Felix-Hausdorff-Str. 4, 17487, Greifswald, Germany

    Michael Lalk & Uwe T. Bornscheuer

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  1. Marie-Katherin Zühlke
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Zühlke, MK., Schlüter, R., Mikolasch, A. et al. Biotransformation and reduction of estrogenicity of bisphenol A by the biphenyl-degrading Cupriavidus basilensis . Appl Microbiol Biotechnol 101, 3743–3758 (2017). https://doi.org/10.1007/s00253-016-8061-z

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