Biotransformation of bisphenol A analogues by the biphenyl-degrading bacterium Cupriavidus basilensis - a structure-biotransformation relationship

• DOI: 10.1007/s00253-020-10406-4
• Publication Date: 2020-03-03T09:03:58Z
• Authors: Marie-Katherin Zü...; Rabea Schlüter; Annett Mikolasch; Ann-Kristin Henning; Martin Giersberg; Michael Lalk; Gotthard Kunze; Thomas Schweder; Tim Urich; Frieder Schauer
• Keywords: Biotransformation; Biphenyl; Bisphenol S; Alicyclic compound

Abstract Comparative analyses determined the relationship between structure of bisphenol A (BPA) as well seven analogues (bisphenol B (BPB), C (BPC), E (BPE), F (BPF), Z (BPZ), AP (BPAP), PH (BPPH)) and their biotransformability by biphenyl-degrading bacterium Cupriavidus basilensis SBUG 290 . All bisphenols were substrates for bacterial transformation with conversion rates ranging from 6 to 98% within 216 h 36 different metabolites characterized. Transformation biphenyl-grown cells comprised four pathways: (a) formation ortho- hydroxylated bisphenols, hydroxylating either one or both phenols compounds; (b) ring fission; (c) transamination followed acetylation dimerization; (d) oxidation substituents, such methyl groups aromatic systems, present on 3-position. However, microbial attack C. was limited phenol rings its while substituents carbon bridge connecting not oxidized. modifications at could be oxidized up cleavage, 3-position other than hydroxyl did allow this reaction. Replacing group BPA a hydrophobic alicyclic system inhibited dimerization acetylation. While most exhibited estrogenic activity, biotransformation products tested estrogenically active.