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1.
Bioorg Chem ; 81: 367-372, 2018 12.
Article in English | MEDLINE | ID: mdl-30196206

ABSTRACT

In this study, the consumption of 4-bromobenzoic acid and 4-chlorobenzoic acid by the fungus Penicillium brasilianum, an endophyte from Melia azedarach is evaluated. This fungus metabolizes these halobenzoic acids to produce three new brominated compounds, which have been isolated and characterized, and three new chlorinated derivatives identified by HRMS. Among these products, (4-bromobenzoyl)proline has been also chemically synthesized and employed in biological assays, thus providing insights for the elucidation of the defense mechanism of P. brasilianum towards these halobenzoic acids.


Subject(s)
Antifungal Agents/metabolism , Bromobenzoates/metabolism , Chlorobenzoates/metabolism , Endophytes/metabolism , Melia azedarach/microbiology , Penicillium/metabolism , Antifungal Agents/chemistry , Biotransformation , Bromobenzoates/chemistry , Chlorobenzoates/chemistry , Endophytes/chemistry , Halogenation , Melia azedarach/metabolism , Molecular Docking Simulation , Penicillium/chemistry , Penicillium/enzymology
2.
Toxicol Lett ; 295: 397-407, 2018 Oct 01.
Article in English | MEDLINE | ID: mdl-30036687

ABSTRACT

Bromo-dragonfly is a benzodifuran derivative known as one of the most potent 5-HT2A-receptor agonists within this chemical class, with long-lasting effects of up to 2-3 days. In addition to hallucinogenic effects, the drug is a potent vasoconstrictor, resulting in severe adverse effects, such as necrosis of the limbs. In some cases, intoxication has had fatal outcomes. Little is known about the metabolism of bromo-dragonfly. The aims of this study were to investigate the pharmacokinetics of bromo-dragonfly, determine the plasma protein binding, examine the human hepatic metabolism in vitro, and compare with those of its close analogue, 2C-B-fly. Additionally, we assayed the inhibition potency of both compounds on the monoamine oxidase (MAO) A- and B-mediated oxidative deamination of serotonin (5-HT) and dopamine, respectively. Liquid chromatography high-resolution mass spectrometry was used for metabolism studies in pooled human liver microsomes (HLM), pooled human liver cytosol (HLC) and recombinant enzymes. Inhibition studies of the deamination of 5-HT and dopamine were carried out using LC-MS/MS. Bromo-dragonfly was not metabolised in the tested in vitro systems. On the other hand, 2C-B-fly was metabolised in HLM by CYP2D6 and in HLC to some extent, with the main biotransformations being monohydroxylation and N-acetylation. Furthermore, MAO-A metabolised 2C-B-fly, producing the aldehyde metabolite, which was trapped in vitro with methoxyamine. Inhibition experiments revealed that bromo-dragonfly is a competitive inhibitor of MAO-A with a Ki of 0.352 µM. The IC50 value for bromo-dragonfly indicated that the inhibition of MAO-A may be clinically relevant. However, more data are needed to estimate its impact on the increase of 5-HT in vivo.


Subject(s)
Bromobenzoates/metabolism , Bromobenzoates/pharmacology , Hallucinogens/metabolism , Hallucinogens/pharmacology , Microsomes, Liver/enzymology , Monoamine Oxidase Inhibitors/metabolism , Monoamine Oxidase Inhibitors/pharmacology , Monoamine Oxidase/metabolism , Propylamines/metabolism , Propylamines/pharmacology , Acetylation , Biotransformation , Chromatography, High Pressure Liquid , Cytochrome P-450 CYP2D6/metabolism , Deamination , Dopamine/metabolism , Humans , Hydroxylation , Kinetics , Oxidation-Reduction , Protein Binding , Serotonin/metabolism , Tandem Mass Spectrometry
3.
Brain Res ; 1672: 137-147, 2017 Oct 01.
Article in English | MEDLINE | ID: mdl-28760439

ABSTRACT

Our aim was to explore the preventive and therapeutic effects of sodium (±)-5-bromo-2-(α-hydroxypentyl) benzoate (brand name: brozopine, BZP) on stroke in Dahl Salt-sensitive (Dahl-SS) hypertensive rats. Dahl-SS rats were fed a high-salt diet to observe the effect of BZP on blood pressure, and brain, heart, and kidney tissues. Additionally, the incidence of stroke was recorded according to the neurological score. The relative mechanisms investigated included anti-oxidative effects and anti-platelet aggregation. BZP reduced the incidence of stroke, neuronal necrosis in the brain, and cell swelling and inflammatory infiltration in the kidney. Its mechanisms were related to the increased activities of gluthatione peroxidase and catalase and the decreased level of plasma nitric oxide. BZP inhibited arachidonic acid (AA) - induced platelet aggregation (IC50: 12µM) rather than that of adenosine diphosphate (ADP) - and/or thrombin-induced platelet aggregation in vitro. Interestingly, BZP inhibited ADP-, thrombin-, or AA-induced platelet aggregation and elevated the level of AMP-activated protein kinase, cyclic guanosine monophosphate, and vasodilator-stimulated-phosphoprotein, and attenuated ATP contents and mitogen-activated protein kinase levels in platelet and inhibited thrombus formation in a carotid artery thrombosis model, dose-dependently, in Dahl-SS hypertensive-induced stroke rats. In conclusion, BZP can have therapeutic and preventive effects on stroke in Dahl-SS hypertensive rats, the mechanisms of which may be related to anti-oxidant, anti-platelet aggregation and anti-thrombus formation.


Subject(s)
Bromobenzoates/pharmacology , Stroke/drug therapy , Animals , Blood Pressure/drug effects , Bromobenzoates/metabolism , Bromobenzoates/therapeutic use , Cyclic GMP/metabolism , Hypertension/metabolism , Hypertension/physiopathology , Kidney/metabolism , Male , Nitric Oxide/metabolism , Rats , Rats, Inbred Dahl/physiology , Sodium/metabolism , Sodium Chloride, Dietary/metabolism , Stroke/metabolism , Stroke/prevention & control
4.
Biotechnol Lett ; 37(12): 2395-401, 2015 Dec.
Article in English | MEDLINE | ID: mdl-26264243

ABSTRACT

OBJECTIVES: To confirm the reductive dehalogenation ability of the aerobic strain of Delftia sp. EOB-17, finding more evidences to support the hypothesis that reductive dehalogenation may occur extensively in aerobic bacteria. RESULTS: Delftia sp. EOB-17, isolated from terrestrial soil contaminated with halogenated aromatic compounds, completely degraded 0.2 mM DBHB in 28 h and released two equivalents of bromides under aerobic conditions in the presence of sodium succinate. LC-MS analysis revealed that DBHB was transformed to 4-hydroxybenzoate via 3-bromo-4-hydroxybenzoate by successive reductive dehalogenation. Highly conserved DBHB-degrading genes, including reductive dehalogenase gene (bhbA3) and the extra-cytoplasmic binding receptor gene (bhbB3), were also found in strain EOB-17 by genome sequencing. The optimal temperature and pH for DBHB reductive dehalogenation activity are 30 °C and 8, respectively, and 0.1 mM Cd(2+), Cu(2+), Hg(2+) and Zn(2+) strongly inhibited dehalogenation activity. CONCLUSIONS: The aerobic strain of Delftia sp. EOB-17 was confirmed to reductively dehalogenate DBHB under aerobic conditions, providing another evidence to support the hypothesis that reductive dehalogenation occurs extensively in aerobic bacteria.


Subject(s)
Bromobenzoates/metabolism , Delftia/metabolism , Aerobiosis , Biotransformation , Chromatography, Liquid , Delftia/isolation & purification , Enzyme Inhibitors/metabolism , Hydrogen-Ion Concentration , Mass Spectrometry , Metals, Heavy/metabolism , Parabens/metabolism , Soil Microbiology , Temperature
5.
J Hazard Mater ; 287: 24-31, 2015 Apr 28.
Article in English | MEDLINE | ID: mdl-25625627

ABSTRACT

Monohalogenated benzoic acids often appear in industrial wastewaters where biodegradation can be hampered by complex mixtures of pollutants and prevailing extreme milieu conditions. In this study, the biodegradation of chlorinated and brominated benzoic acids was conducted at a pH range of 5.0-9.0, at elevated salt concentrations and with pollutant mixtures including fluorinated and iodinated compounds. In mixtures of the isomers, the degradation order was primarily 4-substituted followed by 3-substituted and then 2-substituted halogenated benzoic acids. If the pH and salt concentration were altered simultaneously, long adaptation periods were required. Community analyses were conducted in liquid batch cultures and after immobilization on sand columns. The Alphaproteobacteria represented an important fraction in all of the enrichment cultures. On the genus level, Afipia sp. was detected most frequently. In particular, Bacteroidetes were detected in high numbers with chlorinated benzoic acids.


Subject(s)
Bromobenzoates/metabolism , Chlorobenzoates/metabolism , Microbial Consortia , Sewage/microbiology , Biodegradation, Environmental , Hydrogen-Ion Concentration , Salinity
6.
Chemosphere ; 112: 362-9, 2014 Oct.
Article in English | MEDLINE | ID: mdl-25048928

ABSTRACT

The present study investigated and compared the estrogenic and androgenic activities of the three different classes of environmental pollutants and their metabolites using the XenoScreen XL YES/YAS assay, which has advantages compared with the original YES/YAS protocol. Contrary to the parent brominated flame retardants TBB and TBPH, which demonstrated no or very weak (anti)estrogenic or (anti)androgenic activities, their metabolites, TBBA and TBMEPH, exhibited anti-estrogenic (IC50 for TBBA=31.75 µM and IC50 for TBMEPH=0.265 µM) and anti-androgenic (IC50 for TBBA=73.95 µM and IC50 for TBMEPH=2.92 µM) activities. These results reveal that metabolism can enhance the anti-estrogenic and anti-androgenic effects of these two novel brominated flame retardants. Based on the activities of BPAF, BPF, BPA and MBP, we can conclude that the XenoScreen XL YES/YAS assay gives comparable results to the (anti)estrogenic or (anti)androgenic assays that are reported in the literature. For BPA, it was confirmed previously that the metabolite formed after an ipso-reaction (hydroxycumyl alcohol) exhibited higher estrogenic activity compared with the parent BPA, but this was not confirmed for BPAF and BPF ipso-metabolites, which were not active in the XenoScreen YES/YAS assay. Among the substituted BPA analogues, bis-GMA exhibited weak anti-estrogenic activity, BADGE demonstrated weak anti-estrogenic and anti-androgenic activities (IC50=13.73 µM), and the hydrolysed product BADGE·2H2O demonstrated no (anti)estrogenic or (anti)androgenic activities.


Subject(s)
Biological Assay/methods , Bromobenzoates/toxicity , Endocrine Disruptors/metabolism , Flame Retardants/metabolism , Halogenated Diphenyl Ethers/toxicity , Phenols/toxicity , Saccharomyces cerevisiae/drug effects , Androgen Antagonists/metabolism , Androgen Antagonists/toxicity , Bromobenzoates/metabolism , Carboxylic Acids/metabolism , Environmental Pollutants/metabolism , Environmental Pollutants/toxicity , Estrogen Antagonists/metabolism , Estrogen Antagonists/toxicity , Halogenated Diphenyl Ethers/metabolism
7.
Environ Health Perspect ; 120(12): 1711-9, 2012 Dec.
Article in English | MEDLINE | ID: mdl-23014847

ABSTRACT

BACKGROUND: Bis-(2-ethylhexyl) tetrabromophthalate (TBPH) is widely used as a replacement for polybrominated diphenyl ethers (PBDEs) in commercial flame retardant mixtures such as Firemaster 550. It is also used in a commercial mixture called DP 45. Mono-(2-ethyhexyl) tetrabromophthalate (TBMEHP) is a potentially toxic metabolite. OBJECTIVES: We used in vitro and rodent in vivo models to evaluate human exposure and the potential metabolism and toxicity of TBPH. METHODS: Dust collected from homes, offices, and cars was measured for TBPH by gas chromatography followed by mass spectrometry. Pregnant rats were gavaged with TBMEHP (200 or 500 mg/kg) or corn oil on gestational days 18 and 19, and dams and fetuses were evaluated histologically for toxicity. We also assessed TBMEHP for deiodinase inhibition using rat liver microsomes and for peroxisome proliferator-activated receptor (PPAR) α and γ activation using murine FAO cells and NIH 3T3 L1 cells. RESULTS: TBPH concentrations in dust from office buildings (median, 410 ng/g) were higher than in main living areas in homes (median, 150 ng/g). TBPH was metabolized by purified porcine esterases to TBMEHP. Two days of TBMEHP exposure in the rat produced maternal hypothyroidism with markedly decreased serum T3 (3,3´,5-triiodo-l-thyronine), maternal hepatotoxicity, and increased multinucleated germ cells (MNGs) in fetal testes without antiandrogenic effects. In vitro, TBMEHP inhibited deiodinase activity, induced adipocyte differentiation in NIH 3T3 L1 cells, and activated PPARα- and PPARγ-mediated gene transcription in NIH 3T3 L1 cells and FAO cells, respectively. CONCLUSIONS: TBPH a) is present in dust from indoor environments (implying human exposure) and b) can be metabolized by porcine esterases to TBMEHP, which c) elicited maternal thyrotoxic and hepatotoxic effects and d) induced MNGs in the fetal testes in a rat model. In mouse NIH 3T3 L1 preadipocyte cells, TBMEHP inhibited rat hepatic microsome deiodinase activity and was an agonist for PPARs in murine FAO and NIH 3T3 L1 cells.


Subject(s)
Air Pollutants/metabolism , Air Pollutants/toxicity , Air Pollution, Indoor/adverse effects , Bromobenzoates/metabolism , Bromobenzoates/toxicity , Environmental Exposure , Halogenated Diphenyl Ethers/metabolism , Halogenated Diphenyl Ethers/toxicity , Air Pollutants/analysis , Air Pollutants/blood , Air Pollution, Indoor/analysis , Animals , Automobiles , Boston , Bromobenzoates/analysis , Bromobenzoates/blood , Dust/analysis , Environmental Monitoring , Esterases/metabolism , Female , Fetus , Flame Retardants/analysis , Flame Retardants/metabolism , Flame Retardants/toxicity , Halogenated Diphenyl Ethers/analysis , Halogenated Diphenyl Ethers/blood , Housing , Liver/drug effects , Liver/metabolism , Male , Phthalic Acids , Pregnancy , Rats , Rats, Inbred F344 , Swine , Testis/drug effects , Testis/metabolism , Thyroid Gland/drug effects , Thyroid Gland/metabolism , Tissue Distribution , Workplace
8.
Org Biomol Chem ; 9(10): 3920-8, 2011 May 21.
Article in English | MEDLINE | ID: mdl-21472181

ABSTRACT

Metabolism of meta-bromobenzoic acid by the blocked mutant Ralstonia eutrophus B9 affords an enantiopure dearomatised halodiene-diol which we demonstrate is a versatile chiron for organic synthesis. The presence of the halogen leads to reactivity that is distinct to that observed for the non-halogenated analogue and also serves as a synthetic handle for further functionalisation.


Subject(s)
Bromobenzoates/chemistry , Bromobenzoates/metabolism , Cupriavidus necator/metabolism , Oxidation-Reduction , Stereoisomerism , Substrate Specificity
9.
FEMS Microbiol Lett ; 213(2): 183-8, 2002 Aug 06.
Article in English | MEDLINE | ID: mdl-12167535

ABSTRACT

4-Chlorobenzoate and 4-bromobenzoate were readily degraded in denitrifying enrichment cultures established with river sediment, estuarine sediment or agricultural soil as inoculum. Stable denitrifying consortia were obtained and maintained by serial dilution and repeated feeding of substrates. Microbial community analyses were performed to characterize the 4-chlorobenzoate and 4-bromobenzoate degrading consortia with terminal restriction fragment length polymorphism (T-RFLP) and cloning of 16S rRNA genes from the cultures. Interestingly, two major terminal restriction fragments (T-RFs) in the 4-chlorobenzoate degrading consortia and one T-RF in the 4-bromobenzoate utilizing consortium were observed from T-RFLP analysis regardless of their geographical and ecological origins. The two T-RFs (clones 4CB1 and 4CB2) in 4-chlorobenzoate degrading consortia were identified as members of the beta-subunit of the Proteobacteria on the basis of 16S rRNA sequencing analysis. Phylogenetic analysis of 16S rRNA genes showed that clone 4CB1 was closely related to Thauera aromatica while clone 4CB2 was distantly related to the genera Limnobacter and Ralstonia. The 4-bromobenzoate utilizing consortium mainly consisted of one T-RF, which was identical to clone 4CB2 in spite of different enrichment substrate. This suggests that degradation of 4-chlorobenzoate and 4-bromobenzoate under denitrifying conditions was mediated by bacteria belonging to the beta-subunit of the Proteobacteria.


Subject(s)
Betaproteobacteria/isolation & purification , Betaproteobacteria/metabolism , Bromobenzoates/metabolism , Chlorobenzoates/metabolism , Nitrates/metabolism , Soil Pollutants/metabolism , Betaproteobacteria/classification , Betaproteobacteria/genetics , Biodegradation, Environmental , Nitrites/metabolism , Phylogeny , Polymorphism, Restriction Fragment Length , RNA, Ribosomal, 16S/genetics , Sequence Analysis, DNA , Soil Microbiology , Substrate Specificity
10.
Arch Microbiol ; 171(4): 230-6, 1999 Mar.
Article in English | MEDLINE | ID: mdl-10339806

ABSTRACT

A denitrifying bacterium was isolated from a river sediment after enrichment on 3-chlorobenzoate under anoxic, denitrifying conditions. The bacterium, designated strain 3CB-1, degraded 3-chlorobenzoate, 3-bromobenzoate, and 3-iodobenzoate with stoichiometric release of halide under conditions supporting anaerobic growth by denitrification. The 3-halobenzoates and 3-hydroxybenzoate were used as growth substrates with nitrate as the terminal electron acceptor. The doubling time when growing on 3-halobenzoates ranged from 18 to 25 h. On agar plates with 1 mM 3-chlorobenzoate as the sole carbon source and 30 mM nitrate as the electron acceptor, strain 3CB-1 formed small colonies (1-2 mm in diameter) in 2 to 3 weeks. Anaerobic degradation of both 3-chlorobenzoate and 3-hydroxybenzoate was dependent on nitrate as an electron acceptor and resulted in nitrate reduction corresponding to the stoichiometric values for complete oxidation of the substrate to CO2. 3-Chlorobenzoate was not degraded in the presence of oxygen. 3-Bromobenzoate and 3-iodobenzoate were also degraded under denitrifying conditions with stoichiometric release of halide, but 3-fluorobenzoate was not utilized by the bacterium. Utilization of 3-chlorobenzoate was inducible, while synthesis of enzymes for 3-hydroxybenzoate degradation was constitutively low, but inducible. Degradation was specific to the positive of the halogen substituent, and strain 3CB-1 did not utilize 2- or 4-chlorobenzoate.


Subject(s)
Benzoates/metabolism , Gram-Negative Bacteria/metabolism , Anaerobiosis , Biodegradation, Environmental , Bromobenzoates/metabolism , Chlorobenzoates/metabolism , Gram-Negative Bacteria/growth & development , Gram-Negative Bacteria/isolation & purification , Iodobenzoates/metabolism , Nitrates/metabolism , Nitrites/metabolism , Water Microbiology
11.
Appl Environ Microbiol ; 63(12): 4698-703, 1997 Dec.
Article in English | MEDLINE | ID: mdl-9471962

ABSTRACT

An anaerobic bacterial coculture which dechlorinated 3-chlorobenzoate (3CB) to benzoate was obtained by single-colony isolation from an anaerobic bacterial consortium which completely degraded 3CB in defined medium. Of 29 additional halogenated aromatic compounds tested, the coculture removed the meta halogen from 2,3- and 2,5-dichlorobenzoate, 3-bromobenzoate (3BB), 5-chlorovanillate (5CV), and 3-chloro-4-hydroxybenzoate. Dechlorinating activity in the coculture required the presence of pyruvate. 5CV was also O-demethoxylated. The coculture contained two cell types: a short, straight gram-negative rod and a long, thin, curved gram-positive rod. The short rod, Desulfomicrobium escambiense, was recently isolated and identified as a new sulfate-reducing bacterial species (B. R. Sharak Genthner, S. D. Friedman, and R. Devereux, Int. J. Syst. Bacteriol. 47:889-892, 1997; B. R. Sharak Genthner, G. Mundfrom, and R. Devereux, Arch. Microbiol. 161:215-219, 1994). D. escambiense did not dehalogenate any of the compounds dehalogenated by the coculture, nor dit it O-demethoxylate 5CV or vanillate. However, D. escambiense reduced 3CB, EBB, and benzoate to their respective benzyl alcohols. Reduction to alcohols required the presence of pyruvate, which was transformed to acetate, lactate, and succinate in the presence of absence of 3CB, 3BB, or benzoate. Alcohol formation did not occur in pyruvate-sulfate medium. Under these conditions, sulfate was preferentially reduced. Other electron donors that supported the growth of D. escambiense during sulfate reduction did not support benzoate reduction to benzyl alcohol.


Subject(s)
Benzoates/metabolism , Bromobenzoates/metabolism , Chlorobenzoates/metabolism , Sulfur-Reducing Bacteria/metabolism , Benzoic Acid , Benzyl Alcohols/metabolism , Biodegradation, Environmental , Oxidation-Reduction , Sulfur-Reducing Bacteria/growth & development , Sulfur-Reducing Bacteria/isolation & purification
12.
Appl Environ Microbiol ; 63(10): 3911-5, 1997 Oct.
Article in English | MEDLINE | ID: mdl-9480645

ABSTRACT

The anaerobic biodegradation of monobrominated phenols and benzoic acids by microorganisms enriched from marine and estuarine sediments was determined in the presence of different electron acceptors [i.e., Fe(III), SO4(2-), or HCO3-]. Under all conditions tested, the bromophenol isomers were utilized without a lengthy lag period whereas the bromobenzoate isomers were utilized only after a lag period of 23 to 64 days. 2-Bromophenol was debrominated to phenol, with the subsequent utilization of phenol under all three reducing conditions. Debromination of 3-bromophenol and 4-bromophenol was also observed under sulfidogenic and methanogenic conditions but not under iron-reducing conditions. In the bromobenzoate-degrading cultures, no intermediates were observed under any of the conditions tested. Debromination rates were higher under methanogenic conditions than under sulfate-reducing or iron-reducing conditions. The stoichiometric reduction of sulfate or Fe(III) and the utilization of bromophenols and phenol indicated that biodegradation was coupled to sulfate or iron reduction, respectively. The production of phenol as a transient intermediate demonstrates that reductive dehalogenation is the initial step in the biodegradation of bromophenols under iron- and sulfate-reducing conditions.


Subject(s)
Bromobenzoates/metabolism , Phenols/metabolism , Water Microbiology , Water Pollutants, Chemical/metabolism , Fresh Water/microbiology , Iron/metabolism , Kinetics , Methane/metabolism , Oxidation-Reduction , Seawater/microbiology , Sulfates/metabolism
13.
FEMS Microbiol Lett ; 119(1-2): 199-207, 1994 Jun 01.
Article in English | MEDLINE | ID: mdl-8039661

ABSTRACT

From light-exposed enrichment cultures containing benzoate and a mixture of chlorobenzoates, a pure culture was obtained able to grow with 3-chlorobenzoate (3-CBA) or 3-bromobenzoate (3-BrBA) as the sole growth substrate anaerobically in the light. The thus isolated organism is a photoheterotroph, designated isolate DCP3. It is preliminarily identified as a Rhodopseudomonas palustris strain. It differs from Rhodopseudomonas palustris WS17, the only other known photoheterotroph capable of using 3-CBA for growth, in its independence of benzoate for growth with 3-CBA and in its wider substrate range: if grown on 3-CBA, it can also use 2-CBA, 4-CBA or 3,5-CBA.


Subject(s)
Bromobenzoates/metabolism , Chlorobenzoates/metabolism , Rhodopseudomonas/metabolism , Anaerobiosis , Rhodopseudomonas/growth & development
14.
Appl Environ Microbiol ; 56(6): 1615-9, 1990 Jun.
Article in English | MEDLINE | ID: mdl-2116758

ABSTRACT

A strain of Pseudomonas aeruginosa producing 2-bromobenzoic acid, designated 2-BBZA, was isolated by enrichment culture from municipal sewage. It degraded all four 2-halobenzoates as well as certain 3-halo- and dihalobenzoates, though none of the 4-halobenzoates supported growth of this organism. 3-Hydroxybenzoate and 3-chlorocatechol were respective inhibitors of salicylate and catechol oxidation: when each was added separately to resting cells incubated with 2-bromobenzoate, salicylate and catechol were found. Oxygen uptake data suggest that the same dehalogenase may be involved in the oxidation of 2-bromo-, 2-chloro-, and 2-iodobenzoates.


Subject(s)
Bromobenzoates/metabolism , Pseudomonas aeruginosa/metabolism , Water Microbiology , Culture Media , Hydrolysis , Oxygen/metabolism , Pseudomonas aeruginosa/growth & development , Sewage
15.
FEMS Microbiol Lett ; 51(1): 143-7, 1989 Jul 15.
Article in English | MEDLINE | ID: mdl-2777062

ABSTRACT

Pseudomonas putida strain CLB 250 (DSM 5232) utilized 2-bromo-, 2-chloro- and 2-fluorobenzoate as sole source of carbon and energy. Degradation is suggested to be initiated by a dioxygenase liberating halide in the first catabolic step. After decarboxylation and rearomatization catechol is produced as a central metabolite which is degraded via the ortho-pathway. After inhibition of ring cleavage activities with 3-chlorocatechol, 2-chlorobenzoate was transformed to catechol in nearly stoichiometric amounts. Other ortho-substituted benzoates like anthranilate and 2-methoxybenzoate seem to be metabolized via the same route.


Subject(s)
Benzoates/metabolism , Bromobenzoates/metabolism , Chlorobenzoates/metabolism , Pseudomonas/metabolism , Biodegradation, Environmental , Catechols/biosynthesis , Pseudomonas/enzymology
16.
Appl Environ Microbiol ; 53(4): 810-5, 1987 Apr.
Article in English | MEDLINE | ID: mdl-3579283

ABSTRACT

Alcaligenes denitrificans NTB-1, previously isolated on 4-chlorobenzoate, also utilized 4-bromo-, 4-iodo-, and 2,4-dichlorobenzoate but not 4-fluorobenzoate as a sole carbon and energy source. During growth, stoichiometric amounts of halide were released. Experiments with whole cells and cell extracts revealed that 4-bromo- and 4-iodobenzoate were metabolized like 4-chlorobenzoate, involving an initial hydrolytic dehalogenation yielding 4-hydroxybenzoate, which in turn was hydroxylated to 3,4-dihydroxybenzoate. The initial step in the metabolism of 2,4-dichlorobenzoate was catalyzed by a novel type of reaction for aerobic organisms, involving inducible reductive dechlorination to 4-chlorobenzoate. Under conditions of low and controlled oxygen concentrations, A. denitrificans NTB-1 converted all 4-halobenzoates and 2,4-dichlorobenzoate almost quantitatively to 4-hydroxybenzoate.


Subject(s)
Alcaligenes/metabolism , Bromobenzoates/metabolism , Chlorobenzoates/metabolism , Iodobenzoates/metabolism , Alcaligenes/growth & development , Hydrolysis , Oxygen/pharmacology
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