scholarly journals Metabolism of 2-hydroxy-1-naphthoic acid and naphthalene via gentisic acid by distinctly different sets of enzymes in Burkholderia sp. strain BC1

Microbiology ◽  
2014 ◽  
Vol 160 (5) ◽  
pp. 892-902 ◽  
Author(s):  
Piyali Pal Chowdhury ◽  
Jayita Sarkar ◽  
Soumik Basu ◽  
Tapan K. Dutta
Keyword(s):  
Salicylic Acid ◽  
Sole Source ◽  
Bacterial Degradation ◽  
Disposal Site ◽  
Gentisic Acid ◽  
Metabolic Intermediates ◽  
Naphthoic Acid ◽  
Catechol 1,2 Dioxygenase ◽  
Dual Pathway ◽  
Uptake Studies

Burkholderia sp. strain BC1, a soil bacterium, isolated from a naphthalene balls manufacturing waste disposal site, is capable of utilizing 2-hydroxy-1-naphthoic acid (2H1NA) and naphthalene individually as the sole source of carbon and energy. To deduce the pathway for degradation of 2H1NA, metabolites isolated from resting cell culture were identified by a combination of chromatographic and spectrometric analyses. Characterization of metabolic intermediates, oxygen uptake studies and enzyme activities revealed that strain BC1 degrades 2H1NA via 2-naphthol, 1,2,6-trihydroxy-1,2-dihydronaphthalene and gentisic acid. In addition, naphthalene was found to be degraded via 1,2-dihydroxy-1,2-dihydronaphthalene, salicylic acid and gentisic acid, with the putative involvement of the classical nag pathway. Unlike most other Gram-negative bacteria, metabolism of salicylic acid in strain BC1 involves a dual pathway, via gentisic acid and catechol, with the latter being metabolized by catechol 1,2-dioxygenase. Involvement of a non-oxidative decarboxylase in the enzymic transformation of 2H1NA to 2-naphthol indicates an alternative catabolic pathway for the bacterial degradation of hydroxynaphthoic acid. Furthermore, the biochemical observations on the metabolism of structurally similar compounds, naphthalene and 2-naphthol, by similar but different sets of enzymes in strain BC1 were validated by real-time PCR analyses.

scholarly journals Novel Pathway for the Degradation of 2-Chloro-4-Nitrobenzoic Acid by Acinetobacter sp. Strain RKJ12

2011 ◽  
Vol 77 (18) ◽  
pp. 6606-6613 ◽  
Author(s):  
Dhan Prakash ◽  
Ravi Kumar ◽  
R. K. Jain ◽  
B. N. Tiwary
Keyword(s):  
Salicylic Acid ◽  
Tricarboxylic Acid Cycle ◽  
Sole Source ◽  
Degradation Pathway ◽  
Ring Cleavage ◽  
Muconic Acid ◽  
Content Type ◽  
Nitrobenzoic Acid ◽  
Catabolic Genes ◽  
Catechol 1,2 Dioxygenase

ABSTRACTThe organismAcinetobactersp. RKJ12 is capable of utilizing 2-chloro-4-nitrobenzoic acid (2C4NBA) as a sole source of carbon, nitrogen, and energy. In the degradation of 2C4NBA by strain RKJ12, various metabolites were isolated and identified by a combination of chromatographic, spectroscopic, and enzymatic activities, revealing a novel assimilation pathway involving both oxidative and reductive catabolic mechanisms. The metabolism of 2C4NBA was initiated by oxidativeorthodehalogenation, leading to the formation of 2-hydroxy-4-nitrobenzoic acid (2H4NBA), which subsequently was metabolized into 2,4-dihydroxybenzoic acid (2,4-DHBA) by a mono-oxygenase with the concomitant release of chloride and nitrite ions. Stoichiometric analysis indicated the consumption of 1 mol O2per conversion of 2C4NBA to 2,4-DHBA, ruling out the possibility of two oxidative reactions. Experiments with labeled H218O and18O2indicated the involvement of mono-oxygenase-catalyzed initial hydrolytic dechlorination and oxidative denitration mechanisms. The further degradation of 2,4-DHBA then proceeds via reductive dehydroxylation involving the formation of salicylic acid. In the lower pathway, the organism transformed salicylic acid into catechol, which was mineralized by theorthoring cleavage catechol-1,2-dioxygenase tocis, cis-muconic acid, ultimately forming tricarboxylic acid cycle intermediates. Furthermore, the studies carried out on a 2C4NBA−derivative and a 2C4NBA+transconjugant demonstrated that the catabolic genes for the 2C4NBA degradation pathway possibly reside on the ∼55-kb transmissible plasmid present in RKJ12.

scholarly journals AzeR, a transcriptional regulator that responds to azelaic acid in Pseudomonas nitroreducens

Microbiology ◽  
2020 ◽  
Vol 166 (1) ◽  
pp. 73-84 ◽  
Author(s):  
Cristina Bez ◽  
Sree Gowrinadh Javvadi ◽  
Iris Bertani ◽  
Giulia Devescovi ◽  
Corrado Guarnaccia ◽  
...  
Keyword(s):  
Azelaic Acid ◽  
Type Species ◽  
Isocitrate Lyase ◽  
Model Organism ◽  
Transcriptional Regulator ◽  
Sole Source ◽  
Bacterial Degradation ◽  
Content Type ◽  
Link Type ◽  
Pseudomonas Nitroreducens

Azelaic acid is a dicarboxylic acid that has recently been shown to play a role in plant-bacteria signalling and also occurs naturally in several cereals. Several bacteria have been reported to be able to utilize azelaic acid as a unique source of carbon and energy, including Pseudomonas nitroreducens . In this study, we utilize P. nitroreducens as a model organism to study bacterial degradation of and response to azelaic acid. We report genetic evidence of azelaic acid degradation and the identification of a transcriptional regulator that responds to azelaic acid in P. nitroreducens DSM 9128. Three mutants possessing transposons in genes of an acyl-CoA ligase, an acyl-CoA dehydrogenase and an isocitrate lyase display a deficient ability in growing in azelaic acid. Studies on transcriptional regulation of these genes resulted in the identification of an IclR family repressor that we designated as AzeR, which specifically responds to azelaic acid. A bioinformatics survey reveals that AzeR is confined to a few proteobacterial genera that are likely to be able to degrade and utilize azelaic acid as the sole source of carbon and energy.

Simultaneous liquid-chromatographic quantitation of salicylic acid, salicyluric acid, and gentisic acid in urine.

1980 ◽  
Vol 26 (1) ◽  
pp. 111-114
Author(s):  
B E Cham ◽  
F Bochner ◽  
D M Imhoff ◽  
D Johns ◽  
M Rowland
Keyword(s):  
Salicylic Acid ◽  
Internal Standard ◽  
Peak Height ◽  
Reversed Phase ◽  
Gentisic Acid ◽  
Salicyluric Acid ◽  
Analytical Recovery ◽  
Volume Response ◽  
Assay Precision ◽  
Liquid Chromatographic

Abstract We have developed a specific and sensitive method for the determination of salicylic acid, salicyluric acid, and gentisic acid in urine. Any proteins present are precipitated with methyl cyanide. After centrifugation, an aliquot of the supernate is directly injected into an octadecyl silane reversed-phase chromatographic column, then eluted with a mixture of water, butanol, acetic acid, and sodium sulfate, and quantitated at 313 nm by ultraviolet detection according to peak-height ratios (with internal standard, o-methoxybenzoic acid) or peak heights (no internal standard). The method allows estimates within 25 min. Sensitivity was 0.2 mg/L for gentisic acid, and 0.5 mg/L for both salicyluric and salicylic acid (20-micro L injection volume); response was linear with concentration to at least 2.000 g/L for salicylic acid and metabolites. Analytical recovery of salicylic acid and metabolites from urine is complete. Intra-assay precision (coefficient of variation) is 5.52% at 7.5 mg/L for salicylic acid, 5.01% at 9.33 mg/L for salicyluric acid, and 3.07% at 7.96 mg/L for gentisic acid. Interassay precision is 7.32% at 7.51 mg/L for salicylic acid, 5.52% at 8.58 mg/L for salicyluric acid, and 3.97% at 8.32 mg/L for gentisic acid. We saw no significant interference in urine from patients being treated with various drugs other than aspirin.

scholarly journals l-Glucitol Catabolism in Stenotrophomonas maltophilia Ac

2002 ◽  
Vol 68 (2) ◽  
pp. 582-587 ◽  
Author(s):  
Elke Brechtel ◽  
Alexander Huwig ◽  
Friedrich Giffhorn
Keyword(s):  
Stenotrophomonas Maltophilia ◽  
Sole Source ◽  
Intermediary Metabolism ◽  
Metabolic Intermediates ◽  
Initial Substrate ◽  
Carbohydrate Catabolism

ABSTRACT The carbohydrate catabolism of the bacterium Stenotrophomonas maltophilia Ac (previously named Pseudomonas sp. strain Ac), which is known to convert the unnatural polyol l-glucitol to d-sorbose during growth on the former as the sole source of carbon and energy, was studied in detail. All enzymes operating in a pathway that channels l-glucitol via d-sorbose into compounds of the intermediary metabolism were demonstrated, and for some prominent reactions the products of conversion were identified. d-Sorbose was converted by C-3 epimerization to d-tagatose, which, in turn, was isomerized to d-galactose. d-Galactose was the initial substrate of the De Ley-Doudoroff pathway, involving reactions of NAD-dependent oxidation of d-galactose to d-galactonate, its dehydration to 2-keto-3-deoxy-d-galactonate, and its phosphorylation to 2-keto-3-deoxy-d-galactonate 6-phosphate. Finally, aldol cleavage yielded pyruvate and d-glycerate 3-phosphate as the central metabolic intermediates.

scholarly journals Salicylic Acid Sans Aspirin in Animals and Man

2020 ◽  
Author(s):  
James Ronald Lawrence ◽  
Gwendoline Joan Baxter ◽  
John Robert Paterson
Keyword(s):  
Drug Delivery ◽  
Salicylic Acid ◽  
Drug Delivery Systems ◽  
Protective Action ◽  
Sole Source ◽  
Vegetarian Diet ◽  
Low Dose Aspirin ◽  
Drug Free

Analyses in non-aspirin takers finding salicylic acid (SA) and hydroxylated metabolites in serum also SA and salicyluric acid (SU) in urine led to a re-evaluation of dietary sources of salicylates. Fruit and vegetable sources explained higher levels found in drug-free vegetarians, which overlapped with those from patients on low dose aspirin. That drug’s chemo-protective action in cancer is, at least partially, attributable to its principal metabolite, SA—which we believe contributes to the benefits of a vegetarian diet. However, diet is unlikely to be the sole source of the circulating salicylate found in aspirin-free animals and man. We adduced evidence for its persistence in prolonged fasting and biosynthesis in vivo from labelled benzoic acid. We review the roles, defined and potential, of SA in the biosphere. Emphasis on the antiplatelet effect of aspirin in man has detracted from the likely pivotal role of SA in many potential areas of bioregulation—probably as important in animals as in plants. In this expanding field, some aspirin effects, mediated by apparently conserved receptors responding to SA, are discussed. The perspectives revealed may lead to re-evaluation of the place of salicylates in therapeutics and potentially improve formulations and drug delivery systems.

Simultaneous liquid-chromatographic quantitation of salicylic acid, salicyluric acid, and gentisic acid in plasma.

1979 ◽  
Vol 25 (8) ◽  
pp. 1420-1425 ◽  
Author(s):  
B E Cham ◽  
D Johns ◽  
F Bochner ◽  
D M Imhoff ◽  
M Rowland
Keyword(s):  
Salicylic Acid ◽  
Gentisic Acid ◽  
Salicyluric Acid ◽  
Liquid Chromatographic

scholarly journals The isolation and identification of 6-hydroxycyclohepta-1,4-dione as a novel intermediate in the bacterial degradation of atropine

1993 ◽  
Vol 293 (1) ◽  
pp. 115-118 ◽  
Author(s):  
B A Bartholomew ◽  
M J Smith ◽  
M T Long ◽  
P J Darcy ◽  
P W Trudgill ◽  
...  
Keyword(s):  
Growth Medium ◽  
Sole Source ◽  
Bacterial Degradation ◽  
Diauxic Growth ◽  
Growth Substrate ◽  
Isolation And Identification ◽  
Carbon And Nitrogen ◽  
Tropic Acid ◽  
Cell Extracts

Growth of Pseudomonas AT3 on the alkaloid atropine as its sole source of carbon and nitrogen is nitrogen-limited and proceeds by degradation of the tropic acid part of the molecule, with the metabolism of the tropine being limited to the point of release of its nitrogen. A nitrogen-free compound accumulated in the growth medium and was isolated and identified as 6-hydroxycyclohepta-1,4-dione. This novel compound is proposed as an intermediate in tropine metabolism. It served as a growth substrate for the organism and was also the substrate for an NAD(+)-linked dehydrogenase present in cell extracts. The enzyme was induced during the tropine phase of diauxic growth on atropine or during growth on tropine alone.

Metabolism of Aspirin after Therapeutic and Toxic Doses

1990 ◽  
Vol 9 (3) ◽  
pp. 131-136 ◽  
Author(s):  
D.K. Patel ◽  
A. Hesse ◽  
A. Ogunbona ◽  
L.J. Notarianni ◽  
P.N. Bennett
Keyword(s):  
Salicylic Acid ◽  
Therapeutic Dose ◽  
Urinary Metabolites ◽  
Urinary Recovery ◽  
Main Metabolite ◽  
Gentisic Acid ◽  
Salicyluric Acid ◽  
Glycine Conjugate ◽  
Kinetics Of

1 The urinary recovery of metabolites of aspirin (ASA) was studied in 45 volunteers who took a therapeutic dose (600 mg) of ASA by mouth and in 37 patients who took ASA in overdose. 2 The main metabolite recovered from the volunteers was the glycine conjugate, salicyluric acid (SUA), which accounted for 75.01 ± 1.19% of total urinary metabolites, whereas salicylic acid (SA) accounted for 8.82 ± 0.56%. Recovery of SUA was negatively correlated with that of SA (r = -0.8625, P < 0.001). 3 In 24 patients with admission plasma salicylate concentrations of 240-360 mg 1-1, SUA accounted for 46.66 ± 3.22% and SA for 31.88 ± 4.02%. 4 In 13 patients with admission plasma salicylate concentrations of 715-870 mg 1-1, SUA accounted for 21.57 ± 3.65% and SA for 64.72 ± 4.82%. 5 Reduced excretion of salicylate as SUA was also accompanied by increased elimination as gentisic acid and salicylic acid phenolic glucuronide indicating that the unsaturated processes that lead to the formation of these metabolites contribute significantly (22-23%) to the inactivation of large doses of salicylate. 6 While the Michalis-Menten kinetics of ASA have been well demonstrated at lower doses, our findings illustrate the progressive saturation of SUA formation under conditions of increasing ASA load to toxic amounts and raise issues about the in-vivo glycine pool when ASA is taken in overdose.

scholarly journals Microbial degradation of alkylbenzenesulphonates. Metabolism of homologues of short alkyl-chain length by an Alcaligenes sp

1974 ◽  
Vol 140 (2) ◽  
pp. 121-134 ◽  
Author(s):  
J. Anthony Bird ◽  
Ronald B. Cain
Keyword(s):  
Alkyl Chain ◽  
Sole Source ◽  
Oxidation Products ◽  
Ring Cleavage ◽  
Growth Substrate ◽  
First Order ◽  
Heat Treated ◽  
Catechol 1,2 Dioxygenase ◽  
Benzene Toluene ◽  
Ortho Pathway

1. An organism isolated from sewage and identified as an Alcaligenes sp. utilized benzenesulphonate, toluene-p-sulphonate or phenylethane-p-sulphonate as sole source of carbon and energy for growth. Higher alkylbenzenesulphonate homologues and the hydrocarbons, benzene, toluene, phenylethane and 1-phenyldodecane were not utilized. 2. 2-Phenylpropanesulphonate was metabolized to 4-isopropylcatechol. 3. 1-Phenylpropanesulphonate was metabolized to an ortho-diol, which was tentatively identified, in the absence of an authentic specimen, as 4-n-propylcatechol. 4. In the presence of 4-isopropylcatechol, which inhibited catechol 2,3-dioxygenase, 4-ethylcatechol accumulated in cultures growing on phenylethane-p-sulphonate. 5. Authentic samples of catechol, 3-methylcatechol, 4-methylcatechol, 4-ethylcatechol and 3-isopropylcatechol were oxidized by heat-treated extracts to the corresponding 2-hydroxyalkylmuconic semialdehydes. Ring cleavage occurred between C-2 and C-3. 6. The catechol derived from 1-phenylpropanesulphonate was oxygenated by catechol 2,3-dioxygenase to a compound with all the properties of a 2-hydroxyalkylmuconic semialdehyde, but it was not rigorously identified. 7. The catechol 2,3-dioxygenase induced by growth on benzenesulphonate, toluene-p-sulphonate or phenylethane-p-sulphonate showed a constant ratio of specific activities with catechol, 3-methylcatechol, 4-methylcatechol and 4-ethylcatechol that was independent of the growth substrate. At 60°C, activity towards these substrates declined at an identical first-order rate. 8. Enzymes of the ‘ortho’ pathway of catechol metabolism were present in small amounts in cells grown on benzenesulphonate, toluene-p-sulphonate or phenylethane-p-sulphonate. 9. The catechol 1,2-dioxygenase oxidized the alkylcatechols, but the rates and the total extents of oxidation were less than for catechol itself. The oxidation products of these alkylcatechols were not further metabolized.

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