title: Biotransformation and reduction of estrogenicity of bisphenol A by the biphenyl-degrading Cupriavidus basilensis.
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.
authors.affiliation: Institute of Microbiology, Ernst-Moritz-Arndt-University of Greifswald, Friedrich-Ludwig-Jahn-Str. 15, 17487, Greifswald, Germany.
authors.forename: Marie-Katherin
authors.initials: MK
authors.lastname: Zühlke
authors.affiliation: Institute of Microbiology, Ernst-Moritz-Arndt-University of Greifswald, Friedrich-Ludwig-Jahn-Str. 15, 17487, Greifswald, Germany. rabea.schlueter@uni-greifswald.de.
authors.forename: Rabea
authors.initials: R
authors.lastname: Schlüter
authors.affiliation: Institute of Microbiology, Ernst-Moritz-Arndt-University of Greifswald, Friedrich-Ludwig-Jahn-Str. 15, 17487, Greifswald, Germany.
authors.forename: Annett
authors.initials: A
authors.lastname: Mikolasch
authors.affiliation: Institute of Microbiology, Ernst-Moritz-Arndt-University of Greifswald, Friedrich-Ludwig-Jahn-Str. 15, 17487, Greifswald, Germany.
authors.forename: Daniela
authors.initials: D
authors.lastname: Zühlke
authors.affiliation: Leibniz Institute of Plant Genetics and Crop Plant Research, Corrensstr. 3, OT Gatersleben, 06466, Seeland, Germany.
authors.forename: Martin
authors.initials: M
authors.lastname: Giersberg
authors.affiliation: Institute of Microbiology, Ernst-Moritz-Arndt-University of Greifswald, Friedrich-Ludwig-Jahn-Str. 15, 17487, Greifswald, Germany.
authors.forename: Henning
authors.initials: H
authors.lastname: Schindler
authors.affiliation: Institute of Microbiology, Ernst-Moritz-Arndt-University of Greifswald, Friedrich-Ludwig-Jahn-Str. 15, 17487, Greifswald, Germany.
authors.forename: Ann-Kristin
authors.initials: AK
authors.lastname: Henning
authors.affiliation: Institute of Microbiology, Ernst-Moritz-Arndt-University of Greifswald, Friedrich-Ludwig-Jahn-Str. 15, 17487, Greifswald, Germany.
authors.forename: Heidi
authors.initials: H
authors.lastname: Frenzel
authors.affiliation: Institute of Microbiology, Ernst-Moritz-Arndt-University of Greifswald, Friedrich-Ludwig-Jahn-Str. 15, 17487, Greifswald, Germany.
authors.forename: Elke
authors.initials: E
authors.lastname: Hammer
authors.affiliation: Institute of Biochemistry, Ernst-Moritz-Arndt-University of Greifswald, Felix-Hausdorff-Str. 4, 17487, Greifswald, Germany.
authors.forename: Michael
authors.initials: M
authors.lastname: Lalk
authors.affiliation: Institute of Biochemistry, Ernst-Moritz-Arndt-University of Greifswald, Felix-Hausdorff-Str. 4, 17487, Greifswald, Germany.
authors.forename: Uwe T
authors.initials: UT
authors.lastname: Bornscheuer
authors.affiliation: Institute of Microbiology, Ernst-Moritz-Arndt-University of Greifswald, Friedrich-Ludwig-Jahn-Str. 15, 17487, Greifswald, Germany.
authors.forename: Katharina
authors.initials: K
authors.lastname: Riedel
authors.affiliation: Leibniz Institute of Plant Genetics and Crop Plant Research, Corrensstr. 3, OT Gatersleben, 06466, Seeland, Germany.
authors.forename: Gotthard
authors.initials: G
authors.lastname: Kunze
authors.affiliation: Institute of Microbiology, Ernst-Moritz-Arndt-University of Greifswald, Friedrich-Ludwig-Jahn-Str. 15, 17487, Greifswald, Germany.
authors.forename: Frieder
authors.initials: F
authors.lastname: Schauer
mesh_terms: D001559:Benzhydryl Compounds / Q000378:metabolism*; D001711:Biotransformation; D002244:Carbon / Q000378:metabolism; D049921:Cupriavidus / Q000254:growth & development / Q000378:metabolism*; D004968:Estrogens, Non-Steroidal / Q000378:metabolism*; D053858:Metabolic Networks and Pathways; D010636:Phenols / Q000378:metabolism*; D000098826:Bisphenol A Compounds
chemical_list: D001559:Benzhydryl Compounds; D002244:Carbon; D004968:Estrogens, Non-Steroidal; D010636:Phenols; C006780:bisphenol A; D000098826:Bisphenol A Compounds
keywords: Biotransformation; Bisphenol A; Cupriavidus basilensis; Estrogenicity; Proteome; Ring cleavage