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

Abstract

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

Croceicoccus bisphenolivorans sp. nov., a bisphenol A-degrading bacterium isolated from seawater

“…Due to its low cost and increased environmentally friendliness when compared to physical and chemical methods, bioremediation of BPA has proved to be a promising method in recent years [3]. Several species of BPA-degrading bacteria have been reported, including Achromobacter xylosoxidans [4], Bacillus cereus and Bacillus megaterium [1, 5], Cupriavidus basilensis [6], Sphingobium bisphenolivorans [7], Sphingomonas bisphenolicum [8], Pseudomonas putida [3, 9], and so on. Here we describe the taxonomic characterization of a novel BPA-degrading species belonging to the genus Croceicoccus .…”

Bisphenol A and Its Analogues Deteriorate the Hormones Physiological Function of the Male Reproductive System: A Mini-Review

“…BPA and its analogues also exhibited endocrine-disrupting activities in the male reproductive system, shown by the disturbance in the hypothalamus-pituitary-gonad (HPG) axis and steroidogenesis [ 54 , 55 , 56 ]. BPF, BPS, and BPAF share a property with oestradiol (E2), that is, these analogues possess the ability to activate the oestrogenic pathway in the human body system [ 57 , 58 ]. Their capability to mimic oestrogen-like properties causes a deterioration in the physiological function of the male reproductive system.…”

Kinetics and biotransformation products of bisphenol F and S during aerobic degradation with activated sludge

“…Currently, only one study of biodegradation of BPF and BPS, by a microbiological community in seawater 15 , and two studies looking at the fate of BPS in soil 1 and AS 16 have been published. Also, specific biodegradation pathways have been proposed only for BPF using Sphingobium yanoikuyae strain FM-2 isolated from river water, in which degradation proceeds via a Baeyer−Villiger reac on 17,18 , and ring fission followed by ring hydroxylation in the case of Cupriavidus basilensis isolated from a composite soil 19 . Zühlke et al 20 suggest that the formation of phosphate conjugates by Bacillus amyloliquefaciens (isolated from AS) is another possible detoxification mechanism for BPF.…”