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.

Sediments in the mangrove areas contribute to the removal of endocrine disrupting chemicals in coastal sediments of Macau SAR, China, and harbour microbial communities capable of degrading E2, EE2, BPA and BPS

“…Several bacterial strains have been isolated from different environments for its ability to degrade BPA (Zhang et al 2013). Some of these bacteria are able to grow on BPA as sole carbon source (Masuda et al 2007;Oshiman et al 2007;Zhang et al 2007;Fujiwara et al 2016;Vijayalakshmi et al 2017) while in other cases bacteria were able to transform BPA after grow on other substrates (Zühlke et al 2017) or in co-metabolism with other compounds (Heidari et al 2017). Degradation of BPA by Cupriavidus basilensis JF1, which was able to degrade BPA as sole carbon source, was significantly enhanced with the addition of phenol as co-substrate (Fischer et al 2010).…”

Biodegradation of Bisphenol A by Sphingobium sp. YC-JY1 and the Essential Role of Cytochrome P450 Monooxygenase

“…Besides, several bacteria with biodegradation ability of BPA were isolated and explored, such as Achromobacter xylosoxidans strain B-16, Cupriavidus basilensis strain JF1, C. basilensis strain SBUG 290, and Novosphingobium sp. TYA-1 [21][22][23][24]. Although BPA degradation pathways have been extensively studied, the knowledge of metabolic mechanisms, including catalysts and genes, was still limited.…”

Bacterial degradation of bisphenol analogues: an overview

“…Similarly, the strain Cupriavidus basilensis SBUG 290 obtained higher BPA degradation e ciency when previously cultivated with biphenyl, achieving 78% degradation of 0.26 mM in 48h (Zühlke et al 2017). Thus, Zühlke et al (2017) cultivated Cupriavidus basilensis strains in biphenyl to carry out degradation experiments with BPF, BPE, BPB, BPZ, BPC, BPAP, and BPPH (Zühlke et al 2020). Cupriavidus basilensis SBUG 290 showed 98% e ciency in the degradation of BPC, 62% of BPB, 31% of BPE, and 6% of BPF, in 216 hours, at a concentration of 60 mg/L (Zühlke et al 2020).…”

“…Almost 66% of BPA in the concentration of 0.21 mM was degraded in 150h when phenol was added (Fischer et al 2010). Similarly, the strain Cupriavidus basilensis SBUG 290 obtained higher BPA degradation e ciency when previously cultivated with biphenyl, achieving 78% degradation of 0.26 mM in 48h (Zühlke et al 2017). Thus, Zühlke et al (2017) cultivated Cupriavidus basilensis strains in biphenyl to carry out degradation experiments with BPF, BPE, BPB, BPZ, BPC, BPAP, and BPPH (Zühlke et al 2020).…”

“…Conversely, the low solubility of BPZ, BPAP, and BPPH made it impossible to investigate the degradation e ciency in Cupriavidus basilensis SBUG 290 (Zühlke et al 2020). Investigations regarding the metabolic pathways for BP cleavage were published previously (Zühlke et al 2020;Zühlke et al 2017;Fischer et al 2010). Due to space limitations, it will not be discussed in our review.…”