Bioconversion of 2-hydroxy-6-oxo-6-(4'-chlorophenyl) hexa-2,4-dienoic acid, the meta-cleavage product of 4-chlorobiphenyl

Ahmad, Darakhshan; Sylvestre, Michel; Sondossi, M.; Massé, Robert

doi:10.1099/00221287-137-6-1375

Cited by 32 publications

(16 citation statements)

References 31 publications

(17 reference statements)

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“…Degradation of BP and CBPs by P. testosteroni B-356 has been shown to be through a common pathway, as it is in many other organisms (2,34). However, other metabolites produced from CBPs, which are not expected to be part of the pathway, have also been characterized and do not seem to affect the main pathway directly (4).…”

Section: Discussionmentioning

confidence: 94%

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Effects of chlorobenzoate transformation on the Pseudomonas testosteroni biphenyl and chlorobiphenyl degradation pathway

Sondossi

Sylvestre

Ahmad

1992

Appl Environ Microbiol

122

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Bacterial conversion of biphenyl (BP) and chlorobiphenyls (CBPs) to benzoates and chlorobenzoates (CBAs) proceeds by introduction of molecular oxygen at the 2,3 position, followed by a 1,2-meta cleavage of the molecule. Complete mineralization of CBPs requires the presence of two sets of genes, one for the transformation of CBPs into CBAs and a second for the degradation of CBAs. It has been shown previously that removal of the CBAs produced from the degradation of CBPs is essential for efficient degradation of CBPs. In this study we confirmed that CBAs inhibit BP and CBP transformation in Pseudomonas testosteroni B-356. Among the three monochlorobenzoates tested, 3-chlorobenzoate was the most effective inhibitor. Furthermore, we found that in strain B-356, CBA transformation is controlled by BP-induced oxygenases that are not present in benzoate-grown cells. We found that this BP-linked CBA transformation pathway transformed CBAs produced from CBPs into several metabolites, including chlorocatechols and corresponding muconic semialdehydes. These metabolites inhibited the 2,3-dihydroxybiphenyl 1,2-dioxygenase, while CBAs by themselves had no effect on this enzyme. Therefore, on the basis of this and other observations, it appears that when CBAs produced from CBPs accumulate in the growth medium, they are converted into unproductive metabolites that reduce the flux of the BP and CBP degradation pathway. The practical implications of these interactions on the microbial degradation of polychlorinated BPs are also discussed.

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Section: Discussionmentioning

confidence: 94%

“…The origins of * Corresponding author. t Present address: Microbiology Department, Weber State University, Ogden, UT 84408-2506. some of these metabolites and their bioconversion pathways from CBP have recently been proposed (4).…”

mentioning

confidence: 99%

Effects of chlorobenzoate transformation on the Pseudomonas testosteroni biphenyl and chlorobiphenyl degradation pathway

Sondossi

Sylvestre

Ahmad

1992

Appl Environ Microbiol

122

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“…Colonies surrounded by a diffusible yellow zone were streaked onto ONR8a+YEP plates. Previous investigators have observed the formation of a diffusible yellow color during microbial degradation of biphenyl and have shown that this color is caused by a meta-cleavage product (1). Control plates without biphenyl were also inoculated.…”

Section: Methodsmentioning

confidence: 99%

Cycloclasticus pugetii gen. nov., sp. nov., an Aromatic Hydrocarbon-Degrading Bacterium from Marine Sediments

Se¹,

et al. 1995

International Journal of Systematic Bacteriology

404

325

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Three heterotrophic bacterial strains were isolated from different locations in Puget Sound, Washington, by using biphenyl as the principal carbon source. These strains grow by using a limited number of organic compounds, including the aromatic hydrocarbons naphthalene, phenanthrene, anthracene, and toluene, as sole carbon sources. These aerobic, gram-negative rods are motile by means of single polar flagella. Their 16s rRNA sequences indicate that they are all members of the y subdivision of the Proteobacteriu. Their closest known relatives are the genera Methylobacter and Methylomonas (genera of methane-oxidizing bacteria), uncultured sulfur-oxidizing symbionts found in marine invertebrates, and clone FL5 containing 16s ribosomal DNA amplified from an environmental source. However, the Puget Sound bacteria do not use methane or methanol as a carbon source and do not oxidize reduced sulfur compounds. Furthermore, a 16s rRNA base similarity comparison revealed that these bacteria are sufficiently different from other bacteria to justify establishment of a new genus. On the basis of the information summarized above, we describe a new genus and species, Cycloclasticus pugetii, for these bacteria; strain PS-1 is the type strain of C. pugetii.Nearshore marine environments receive a wide variety of recalcitrant organic compounds, including hydrocarbons from shipping activities, terrestrial and freshwater runoff and pollution, sewage, and accidental spillage of fuels and other petroleum products. The aliphatic fraction of petroleum hydrocarbons tends to be more easily degraded than the aromatic compounds. Polycyclic aromatic hydrocarbons (PAHs) are of particular concern because of their persistence and toxicity. Many of these compounds are known to be mutagenic and are suspected carcinogens. Because of their relatively poor solubility in water and hydrophobic nature, PAHs strongly adsorb to particulate material, settle to the seafloor, and accumulate in marine sediments. High concentrations of toxic contaminants in sediments have been correlated with a high incidence of histopathological abnormalities in bottomfish, toxicity to sediment infauna, and other adverse effects (41, 42). In Puget Sound and in many other areas of the world, another source of PAH pollution has been the wood products industry; many sites are contaminated with creosote, a wood preservative that is primarily composed of PAHs (33).Despite their refractory nature, hydrocarbons are degraded by microbial activity in marine environments. Alkane degradation has been studied most thoroughly, and degradation of PAHs has also been described (28). Although most of the research on the microbiology of PAH degradation has focused on a few Pseudomonas species, other bacterial genera whose members have been reported to degrade PAHs include the genera Aeromonas, Flavobacterium, Beijerinckia, Alcaligenes, Micrococcus, Vibrio, Flavobacterium, and Mycobacterium (13, 18, 20, 21, 24, 25, 32, 34, 43).In this paper we describe the isolation and characterization of ...

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“…Whereas this is the only characterized degradative pathway for dibenzofuran, alternative fates for (chloro)biphenyl are known, e.g. the reduction of HOPDA (Omori et al 1986b;Ahmad et al 1991;Higson 1992). …”

Section: Introductionmentioning

confidence: 99%

Purification of two isofunctional hydrolases (EC 3.7.1.8) in the degradative pathway for dibenzofuran inSphingomonas sp. strain RW1

1993

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Sphingomonas sp. strain RWl, when grown in salicylate-salts medium, synthesized the enzymes for the degradation of dibenzofuran. The reaction subsequent to rneta cleavage of the first benzene ring was found to be catalyzed by two isofunctional hydrolases, H1 and H2, which were purified by chromatography on anion exchange, hydrophobic interaction and gel filtration media. Each enzyme was able to hydrolyze 2-hydroxy-6-oxo-6-(2-hydroxyphenyl)hexa-2,4-dienoate and 2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoate to produce salicylate and benzoate, respectively. SDS/PAGE of each purified enzyme showed a single band of M r 31000 (H1) or 29 000 (H2). The N-terminal amino acid sequences of the two proteins showed 50% homology.Abbreviations: DHB -2,3-dihydroxybiphenyl, DSM -German Culture Collection (Braunschweig), FPLCprotein liquid chromatograph(y), H O H P D A -2-hydroxy-6-oxo-6-(2-hydroxyphenyl)hexa-2,4-dienoate, HOPDA -2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoate, THB -2,2',3-trihydroxybiphenyl

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Bioconversion of 2-hydroxy-6-oxo-6-(4'-chlorophenyl) hexa-2,4-dienoic acid, the meta-cleavage product of 4-chlorobiphenyl

Cited by 32 publications

References 31 publications

Effects of chlorobenzoate transformation on the Pseudomonas testosteroni biphenyl and chlorobiphenyl degradation pathway

Effects of chlorobenzoate transformation on the Pseudomonas testosteroni biphenyl and chlorobiphenyl degradation pathway

Cycloclasticus pugetii gen. nov., sp. nov., an Aromatic Hydrocarbon-Degrading Bacterium from Marine Sediments

Purification of two isofunctional hydrolases (EC 3.7.1.8) in the degradative pathway for dibenzofuran inSphingomonas sp. strain RW1

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