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. 2008 Jan;74(2):352-8.
doi: 10.1128/AEM.01708-07. Epub 2007 Nov 16.

Degradation of Bis(4-Hydroxyphenyl)methane (bisphenol F) by Sphingobium yanoikuyae strain FM-2 isolated from river water

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Degradation of Bis(4-Hydroxyphenyl)methane (bisphenol F) by Sphingobium yanoikuyae strain FM-2 isolated from river water

Daisuke Inoue et al. Appl Environ Microbiol. 2008 Jan.

Abstract

Three bacteria capable of utilizing bis(4-hydroxyphenyl)methane (bisphenol F [BPF]) as the sole carbon source were isolated from river water, and they all belonged to the family Sphingomonadaceae. One of the isolates, designated Sphingobium yanoikuyae strain FM-2, at an initial cell density of 0.01 (optical density at 600 nm) completely degraded 0.5 mM BPF within 9 h without any lag period under inductive conditions. Degradation assays of various bisphenols revealed that the BPF-metabolizing system of strain FM-2 was effective only on the limited range of bisphenols consisting of two phenolic rings joined together through a bridging carbon without any methyl substitution on the rings or on the bridging structure. A BPF biodegradation pathway was proposed on the basis of metabolite production patterns and identification of the metabolites. The initial step of BPF biodegradation involves hydroxylation of the bridging carbon to form bis(4-hydroxyphenyl)methanol, followed by oxidation to 4,4'-dihydroxybenzophenone. The 4,4'-dihydroxybenzophenone appears to be further oxidized by the Baeyer-Villiger reaction to 4-hydroxyphenyl 4-hydroxybenzoate, which is then cleaved by oxidation to form 4-hydroxybenzoate and 1,4-hydroquinone. Both of the resultant simple aromatic compounds are mineralized.

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Figures

FIG. 1.
FIG. 1.
Time course of BPF degradation by strain FM-2 after preincubation on BPF (closed symbols) or glucose (open symbols). The BPF concentration (circles) and OD600 (triangles) were monitored. Error bars indicate the standard deviation obtained from three independent experiments.
FIG. 2.
FIG. 2.
HPLC chromatograms showing the generation of metabolite peaks along with BPF degradation by strain FM-2 at 40°C (A) and 45°C (B). Numbers in the chromatograms represent the metabolite numbers defined in the text.
FIG. 3.
FIG. 3.
Mass spectra of metabolites formed during degradation of BPF by strain FM-2. (A) Metabolite I identified as bis(4-hydroxyphenyl)-methanol with trimethylsilylation. (B) Metabolite II identified as DHBP with trimethylsilylation. (C) Metabolite III identified as 1,4-hydroquinone with trimethylsilylation. (D) Metabolite IV identified as 1,4-benzoquinone. (E) Metabolite V identified as 4HB with trimethylsilylation. (F) Metabolite VI tentatively identified as 4-hydroxyphenyl 4-hydroxybenzoate with trimethylsilylation.
FIG. 4.
FIG. 4.
Proposed pathway of BPF metabolism by strain FM-2.

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