Biodegradation of resorcinol and catechol by denitrifying enrichment cultures

Milligan, Peter W.; Häggblom, Max M.

doi:10.1002/etc.5620170804

Cited by 49 publications

(14 citation statements)

References 33 publications

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“…Catechol (1,2‐dihydroxybenzene) is used in a variety of applications. It is used as a reagent for photography, dyeing fur, rubber and plastic production and in the pharmaceutical industry (Merck, 1989; Milligan and Häggblom, 1998). Substituted catechols, especially chlorinated and methylated catechols, are by‐products in pulp and oil mills (Neilson et al ., 1991; Capasso et al ., 1995).…”

Section: Introductionmentioning

confidence: 99%

Chemical properties of catechols and their molecular modes of toxic action in cells, from microorganisms to mammals

Schweigert¹,

Zehnder

Eggen³

2001

Environmental Microbiology

517

317

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SummaryCatechols can undergo a variety of chemical reactions. In this review, we particularly focus on complex formations and the redox chemistry of catechols, which play an inportant role in the toxicity of catechols. In the presence of heavy metals, such as iron or copper, stable complexes can be formed. In the presence of oxidizing agents, catechols can be oxidized to semiquinone radicals and in a next step to o-benzoquinones. Heavy metals may catalyse redox reactions in which catechols are involved. Further chemical properties like the acidity constant and the lipophilicity of different catechols are shortly described as well. As a consequence of the chemical properties and the chemical reactions of catechols, many different reactions can occur with biomolecules such as DNA, proteins and membranes, ultimately leading to non-repairable damage. Reactions with nucleic acids such as adduct formation and strand breaks are discussed among others. Interactions with proteins causing protein and enzyme inactivation are described. The membrane±catechol interactions discussed here are lipid peroxidation and uncoupling. The deleterious effect of the interactions between catechols and the different biomolecules is discussed in the context of the observed toxicities, caused by catechols.

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Section: Introductionmentioning

confidence: 99%

Chemical properties of catechols and their molecular modes of toxic action in cells, from microorganisms to mammals

Schweigert¹,

Zehnder

Eggen³

2001

Environmental Microbiology

517

317

View full text Add to dashboard Cite

show abstract

“…They are used as industrial reagents in the production of rubber, dyes, plastics, pharmaceuticals, and cosmetics [1], and they are important pollutants in the effluents of saw and pulp mills [2]. They are used as industrial reagents in the production of rubber, dyes, plastics, pharmaceuticals, and cosmetics [1], and they are important pollutants in the effluents of saw and pulp mills [2].…”

Section: Introductionmentioning

confidence: 99%

Acute Toxicity of (Chloro-)Catechols and (Chloro-)Catechol–copper Combinations in Escherichia Coli Corresponds to Their Membrane Toxicity in Vitro

Schweigert¹,

Hunziker²,

Escher³

et al. 2001

Environ Toxicol Chem

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(Chloro-)catechols are toxic for bacteria and higher organisms, but the mode of action is not yet clearly understood. We have compared the acute toxicity of different chlorinated catechols to Escherichia coli with membrane toxic effects, namely narcosis and uncoupling that we have determined in an in vitro assay. In vitro membrane toxicity was quantified by measuring the accelerated decay of the membrane potential of chromatophores isolated from Rhodobacter sphaeroides. Both acute and membrane toxicity increased with increasing degree of chlorination. Analysis of dose-response curves, pH dependence, and estimated membrane concentrations gave a consistent picture of the mechanisms of membrane toxicity: At pH 7, the higher-chlorinated catechols acted as uncouplers of oxidative and photophosphorylation, and the lower-chlorinated catechols and catechol acted as narcotics. In the case of 3,5-dichlorocatechol and 4-monochlorocatechol at pH 8.8, both mechanisms appeared to contribute to the overall toxicity. Copper exhibited a diverging effect on the toxicity of catechols and of (chloro-)catechols to E. coli. Whereas the presence of copper increased the toxicity of catechol and 4-monochlorocatechol, the toxicity of 3,5-dichlorocatechol, 3,4,5-trichlorocatechol, and tetrachlorocatechol decreased. Again, the results obtained with in vitro assays agreed with the acute toxicity observed in E. coli: The presence of copper accelerated decay of the membrane potential of catechol and 4-monochlorocatechol; however, the effect was reversed by copper in experiments with 3,5-dichlorocatechol, 3,4,5-trichlorocatechol, and tetrachlorocatechol. We have proposed a mechanistic model to explain the diverging effects of copper on the uncoupling activities of the different catechols.

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“…In general, catechols, including chlorocatechols are chemically reactive compounds. A chemical reaction of nitrite with catechol has been described previously by Milligan and Häggblom [36]. The nitrite-catechol complex, or product, appeared as a separate peak from nitrite and catechol in their HPLC chromatograms; attempts to identify the product failed.…”

Section: Discussionmentioning

confidence: 99%

Microbial degradation of chlorobenzene under oxygen‐limited conditions leads to accumulation of 3‐chlorocatechol

Vogt¹,

Simon²,

Alfreider³

et al. 2004

Enviro Toxic and Chemistry

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Five bacterial strains (Acidovorax facilis B517, Cellulomonas turbata B529, Pseudomonas veronii B547, Pseudomonas veronii B549, and Paenibacillus polymyxa B550) isolated on chlorobenzene as the sole source of carbon and energy were screened for the accumulation of the putative metabolic intermediate 3-chlorocatechol during growth on chlorobenzene under oxygen-limited conditions in the presence and absence of nitrate (1 mM). 3-Chlorocatechol accumulated in the growth media of all five strains, but accumulation was significantly less in cultures of A. facilis B517 compared to the other four strains. The presence of nitrate did not influence the biological conversion pattern. However, biologically produced nitrite reacted with 3-chlorocatechol chemically, a reaction that masked the accumulation of 3-chlorocatechol. For P. veronii B549, a clear relationship between the presence of 3-chlorocatechol in the medium and low oxygen concentrations was demonstrated. The assumption is made that accumulation of 3-chlorocatechol is due to the low enzymatic turnover of the 3-chlorocatechol cleaving enzyme, catechol-1,2-dioxygenase, at low oxygen concentrations.

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Biodegradation of resorcinol and catechol by denitrifying enrichment cultures

Cited by 49 publications

References 33 publications

Chemical properties of catechols and their molecular modes of toxic action in cells, from microorganisms to mammals

Chemical properties of catechols and their molecular modes of toxic action in cells, from microorganisms to mammals

Acute Toxicity of (Chloro-)Catechols and (Chloro-)Catechol–copper Combinations in Escherichia Coli Corresponds to Their Membrane Toxicity in Vitro

Microbial degradation of chlorobenzene under oxygen‐limited conditions leads to accumulation of 3‐chlorocatechol

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