Novel pathway for bacterial metabolism of bisphenol A. Rearrangements and stilbene cleavage in bisphenol A metabolism.

Spivack, James L.; Leib, Terry K.; Lobos, John H.

doi:10.1016/s0021-9258(17)37287-3

Cited by 192 publications

(50 citation statements)

References 13 publications

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“…Further investigation of BPA biodegradation was performed by preliminary detection of BPA metabolites. One of the metabolites of BPA biodegradation by bacterium [20], 4hydroxy-acetophenone (Fig. 4(b)), was detected in the sample.…”

Section: The Metabolite Of Bpa Biodegradation In Mbrmentioning

confidence: 98%

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Bisphenol A removal by a membrane bioreactor

Chen

Huang

Lee

2008

Process Biochemistry

105

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Section: The Metabolite Of Bpa Biodegradation In Mbrmentioning

confidence: 98%

“…Some enhanced removal methods for BPA have been investigated [11][12][13][14][15][16][17], and the BPA-degradable bacteria have been isolated from activated sludge [18] and river water [19]. The degradation pathway has also been studied [20].…”

Section: Introductionmentioning

confidence: 99%

Bisphenol A removal by a membrane bioreactor

Chen

Huang

Lee

2008

Process Biochemistry

105

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“…Other bacterial strains that target the carbon bridge are often able to degrade bisphenols. A rearrangement of the bridge enabled cleavage of bisphenols (BPA) into monocyclic aromatic hydrocarbons as reported for strain MV1 (Lobos et al 1992 ; Spivack et al 1994 ), Sphingomonas bisphenolicum AO1, Sphingomonas sp. TTNP3 (Kolvenbach et al 2007 ; Zhang et al 2013b ) or Shewanella haliotis MH137742 (de Santana et al 2019 ).…”

Section: Discussionmentioning

confidence: 69%

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

Zühlke

Schlüter

Mikolasch

et al. 2020

Appl Microbiol Biotechnol

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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.

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“…Oxidation of the aliphatic methyl group of BPA leads to coproduction of methyl-hydroxylated 2,2-bis(4-hydroxyphenyl)-1-propanol and a skeletally rearranged triol 1,2-bis(4-hydroxyphenyl)-2-propanol. Eventually, both 4-hydroxybenzoic acid and 4-hydroxyacetophenone are mineralized [ 71 ]. The microorganism utilizes (R)-2,3-dichloro-1-propanol, whereas the (S)-enantiomer is not degraded [ 72 ].…”

Section: Discussionmentioning

confidence: 99%

Bisphenol A—A Dangerous Pollutant Distorting the Biological Properties of Soil

Zaborowska

Wyszkowska

Borowik

et al. 2021

IJMS

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Bisphenol A (BPA), with its wide array of products and applications, is currently one of the most commonly produced chemicals in the world. A narrow pool of data on BPA–microorganism–plant interaction mechanisms has stimulated the following research, the aim of which has been to determine the response of the soil microbiome and crop plants, as well as the activity of soil enzymes exposed to BPA pressure. A range of disturbances was assessed, based on the activity of seven soil enzymes, an abundance of five groups of microorganisms, and the structural diversity of the soil microbiome. The condition of the soil was verified by determining the values of the indices: colony development (CD), ecophysiological diversity (EP), the Shannon–Weaver index, and the Simpson index, tolerance of soil enzymes, microorganisms and plants (TIBPA), biochemical soil fertility (BA21), the ratio of the mass of aerial parts to the mass of plant roots (PR), and the leaf greenness index: Soil and Plant Analysis Development (SPAD). The data brought into sharp focus the adverse effects of BPA on the abundance and ecophysiological diversity of fungi. A change in the structural composition of bacteria was noted. Bisphenol A had a more beneficial effect on the Proteobacteria than on bacteria from the phyla Actinobacteria or Bacteroidetes. The microbiome of the soil exposed to BPA was numerously represented by bacteria from the genus Sphingomonas. In this object pool, the highest fungal OTU richness was achieved by the genus Penicillium, a representative of the phylum Ascomycota. A dose of 1000 mg BPA kg−1 d.m. of soil depressed the activity of dehydrogenases, urease, acid phosphatase and β-glucosidase, while increasing that of alkaline phosphatase and arylsulfatase. Spring oilseed rape and maize responded significantly negatively to the soil contamination with BPA.

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Novel pathway for bacterial metabolism of bisphenol A. Rearrangements and stilbene cleavage in bisphenol A metabolism.

Cited by 192 publications

References 13 publications

Bisphenol A removal by a membrane bioreactor

Bisphenol A removal by a membrane bioreactor

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

Bisphenol A—A Dangerous Pollutant Distorting the Biological Properties of Soil

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