Microbial transformation of polychlorinated phenoxy phenols.

Valo, R.; Salkinoja‐Salonen, Mirja

doi:10.2323/jgam.32.505

Cited by 29 publications

(27 citation statements)

References 10 publications

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“…In contrast, no adverse effects have been associated with the MeO-PBDEs as such, although methylation and demethylation of several anisoles and phenolic organic compounds via enzymatic reactions have been observed in, e.g., microorganisms Axelrod and Tomchick 1958;Häggblom et al 1993;Neilson et al 1987Neilson et al , 1988Valo and Salkinoja-Salonen 1986;Wan et al 2009). Consequently, perhaps, the OH-PBDEs and MeO-PBDEs should be considered together in evaluating exposure and potential toxic effects.…”

Section: Ecological Relevancementioning

confidence: 84%

Brominated phenols, anisoles, and dioxins present in blue mussels from the Swedish coastline

Löfstrand

Malmvärn

Haglund

et al. 2010

Environ Sci Pollut Res

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Section: Ecological Relevancementioning

confidence: 84%

Brominated phenols, anisoles, and dioxins present in blue mussels from the Swedish coastline

Löfstrand

Malmvärn

Haglund

et al. 2010

Environ Sci Pollut Res

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“…4B). This is not unusual as such activity leading to biotransformation of hydroxy functions attached to aromatic nuclei into methoxy groups has been reported previously for other bacterial strains (5,17). However, this is the first report describing biotransformation of 2,7-dichloro-and 1,2,3,4-tetrachlorodibenzo-p-dioxins by a bacterial strain together with identification of the corresponding metabolites.…”

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confidence: 77%

Biotransformation of 2,7-Dichloro- and 1,2,3,4-Tetrachlorodibenzo- p -Dioxin by Sphingomonas wittichii RW1

Hong

Chang

Nam

et al. 2002

Appl Environ Microbiol

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Aerobic biotransformation of the diaryl ethers 2,7-dichlorodibenzo-p-dioxin and 1,2,3,4-tetrachlorodibenzop-dioxin by the dibenzo-p-dioxin-utilizing strain Sphingomonas wittichii RW1, producing corresponding metabolites, was demonstrated for the first time. Our strain transformed 2,7-dichlorodibenzo-p-dioxin, yielding 4-chlorocatechol, and 1,2,3,4-tetrachlorodibenzo-p-dioxin, producing 3,4,5,6-tetrachlorocatechol and 2-methoxy-3,4,5,6-tetrachlorophenol; all of these compounds were unequivocally identified by mass spectrometry both before and after N,O-bis(trimethylsilyl)-trifluoroacetamide derivatization by comparison with authentic standards. Additional experiments showed that strain RW1 formed a second metabolite, 2-methoxy-3,4,5,6-tetrachlorophenol, from the original degradation product, 3,4,5,6-tetrachlorocatechol, by methylation of one of the two hydroxy substituents.Polychlorinated dibenzo-p-dioxins and dibenzofurans are compounds of considerable environmental concern due to their persistence and toxicity (2). These halogenated compounds have become ubiquitous pollutants because they can be accidentally released (10) after they are formed as unwanted by-products during synthesis of haloaromatic compounds, such as agricultural pesticides (3), or during incineration of industrial or domestic wastes (12,16). In addition to diaryl ethertransforming isolates belonging to genera such as Terrabacter (7, 11) and Pseudomonas (7), workers have isolated and characterized several strains belonging to the genus Sphingomonas which are able to use diaryl ethers, such as dibenzofurans and dibenzo-p-dioxins, as sole sources of carbon and energy (for reviews, see references 2 and 21). Some of these isolates are known to be effective biocatalysts, even catabolizing some diand trichlorinated dibenzo-p-dioxins and dibenzofurans (7,9,19). However, aerobic catabolism of 2,7-dichloro-and 1,2,3,4-tetrachlorodibenzo-p-dioxins, yielding the corresponding metabolites, has not been demonstrated previously.Previous studies showed that in Sphingomonas wittichii RW1 the catabolism of dibenzofurans and dibenzo-p-dioxins is initiated by a ring-hydroxylating dioxygenase (1,18,20), which introduces two hydroxy functions in the angular positions of the corresponding diaryl ethers, thereby producing unstable hemiacetals. The intermediate decays in the case of dibenzop-dioxins, spontaneously yielding the corresponding 2,2Ј,3-trihydroxydiphenyl ether, which is then subjected to meta cleavage and enzymatic hydrolysis, yielding catechol and the corresponding C 6 body 2-hydroxy-cis,cis-muconic acid (for reviews, see references 2 and 21 ). However, although recently reported transformation experiments monitoring the disappearance of selected mono-to tetrachlorinated congeners of dibenzofurans and dibenzo-p-dioxins indicated that even some of the tetrachlorodibenzo-p-dioxins are depleted by the metabolic activity of the bacteria employed (15), there is still a lack of information concerning aerobic bacterial catabolism of tetrachlorinated dibenzo-p-d...

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“…The chemical structure of triclosan is related to many compounds which are wellknown as xenobiotics, such as halogenated diphenyl ethers. Though some reports on the transformation of halogenated diphenyl ether compounds by bacteria are available (21,30), triclosan itself was not metabolized by the strains tested (31) or by Rhodococcus chlorophenolicus, which can methylate several other chlorinated hydroxydiphenyl ethers (34). Several hydroxylated metabolites, as well as 2,4-dichlorophenol and 4-chlorocatechol, are formed from triclosan by rats (33), while guinea pigs mostly form glucuronide conjugates (3).…”

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confidence: 99%

“…Interestingly, methylated triclosan was reported to be present in environmental samples (26), although the origin remained unclear. In any case, several bacterial strains which were able to transform other chlorodiphenyl ether derivatives did not metabolize this substance (31,34,35).…”

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confidence: 99%

Transformation of Triclosan by Trametes versicolor and Pycnoporus cinnabarinus

Hundt

Martin

Hammer

et al. 2000

Appl Environ Microbiol

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We investigated the ability of Trametes versicolor and Pycnoporous cinnabarinus to metabolize triclosan. T. versicolor produced three metabolites, 2-O-(2,4,4-trichlorodiphenyl ether)-␤-D-xylopyranoside, 2-O-(2,4,4-trichlorodiphenyl ether)-␤-D-glucopyranoside, and 2,4-dichlorophenol. P. cinnabarinus converted triclosan to 2,4,4-trichloro-2-methoxydiphenyl ether and the glucoside conjugate known from T. versicolor. The conjugates showed a distinctly lower cytotoxic and microbicidal activity than triclosan did.Triclosan (2,4,4Ј-trichloro-2Ј-hydroxydiphenyl ether; synonym, Irgasan DP 300) has been used as an antimicrobial compound in deodorants (6), soaps, and dentifrices (2, 8, 36) for many years. The mode of action of triclosan has, however, remained unclear. Recently, it was shown that triclosan blocks one step in bacterial fatty acid synthesis (20,24,25). Due to its widespread use, triclosan and some of its derivatives can be detected in the environment (22,26,27). The chemical structure of triclosan is related to many compounds which are wellknown as xenobiotics, such as halogenated diphenyl ethers. Though some reports on the transformation of halogenated diphenyl ether compounds by bacteria are available (21, 30), triclosan itself was not metabolized by the strains tested (31) or by Rhodococcus chlorophenolicus, which can methylate several other chlorinated hydroxydiphenyl ethers (34). Several hydroxylated metabolites, as well as 2,4-dichlorophenol and 4-chlorocatechol, are formed from triclosan by rats (33), while guinea pigs mostly form glucuronide conjugates (3). No reports exist concerning the degradation of triclosan by fungi. The white rot fungi Trametes versicolor and Pycnoporus cinnabarinus are capable of transforming diphenyl ethers, like 4-chlorodiphenyl ether, up to ring cleavage (10, 11). Hydroxylated biarylic ethers are transformed to oligomerization products by laccases secreted by these strains (13). In this paper we describe some biotransformation reactions of triclosan by the white rot fungi T. versicolor and P. cinnabarinus.The strains T. versicolor SBUG-M 1050, T. versicolor DSM 11269, T. versicolor DSM 11309, and P. cinnabarinus SBUG-M 1044 were cultivated in a nitrogen-rich (8 mM) medium. The cultures for transformation were prepared with 0.25 mM (wt/ vol) triclosan (Mallinckrodt-Baker, Griesheim, Germany) and inoculated and incubated as described previously (10, 11).Cell extracts were prepared from a 3-day culture of T. versicolor, harvested by centrifugation, and washed twice with 50 mM ice-cold Tris-HCl buffer (pH 7.5). Cells were broken at 1,000 lb/in 2 using a French press (SLM Amnico, Rochester, N.Y.) and were immediately resuspended in Tris-HCl buffer. The cell extracts (4 ml, approximately 5 mg of protein ml Ϫ1 ) were incubated at 30°C for 24 h with 2.88 mg of triclosan and 1 mg each of UDP-xylose, UDP-glucose, and UDP-glucuronic acid (Sigma, Deisenhofen, Germany).Analysis of metabolites in culture supernatants and purification of intermediates were done by high-performance liquid ...

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Microbial transformation of polychlorinated phenoxy phenols.

Cited by 29 publications

References 10 publications

Brominated phenols, anisoles, and dioxins present in blue mussels from the Swedish coastline

Brominated phenols, anisoles, and dioxins present in blue mussels from the Swedish coastline

Biotransformation of 2,7-Dichloro- and 1,2,3,4-Tetrachlorodibenzo- p -Dioxin by Sphingomonas wittichii RW1

Transformation of Triclosan by Trametes versicolor and Pycnoporus cinnabarinus

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