Total Degradation of 4-Chlorobenzoic Acid by an Acinetobacter sp.

1992 ◽  
Vol 25 (11) ◽  
pp. 411-418 ◽  
Author(s):  
S. Tobita ◽  
S. Iyobe

An organism isolated from a soil sample with 4-chlorobenzoic acid (4-CBA) as the sole carbon and energy source was tentatively identified as an Acinetobacter sp. This organism, strain ST-1, could completely mineralize 4-CBA in pure culture. The strain hydrolytically dehalogenated 4-CBA as the first step in the degradation pathway. The product, 4-hydroxybenzoic acid, was further metabolized via protocatechuic acid (PCA) under aerobic conditions. The conversion of 4-CBA into 4-hydroxybenzoic acid occurred with a yield greater than 80% under anaerobic conditions with continuous passage of nitrogen into the culture, so molecular oxygen was not essential for dehalogenation. Spectrophotometrical studies showed that the strain oxidized PCA to form β-carboxy-cis, cis-muconic acid as the ortho-ring fission product. Cell extracts converted PCA to β-ketoadipic acid, which was evidence that PCA was cleaved by ortho fission and further degraded in the β-ketoadipate pathway.

2003 ◽  
Vol 69 (1) ◽  
pp. 186-190 ◽  
Author(s):  
René van Herwijnen ◽  
Dirk Springael ◽  
Pieter Slot ◽  
Harrie A. J. Govers ◽  
John R. Parsons

ABSTRACT Mycobacterium sp. strain LB501T utilizes anthracene as a sole carbon and energy source. We analyzed cultures of the wild-type strain and of UV-generated mutants impaired in anthracene utilization for metabolites to determine the anthracene degradation pathway. Identification of metabolites by comparison with authentic standards and transient accumulation of o-phthalic acid by the wild-type strain during growth on anthracene suggest a pathway through o-phthalic acid and protocatechuic acid. As the only productive degradation pathway known so far for anthracene proceeds through 2,3-dihydroxynaphthalene and the naphthalene degradation pathway to form salicylate, this indicates the existence of a novel anthracene catabolic pathway in Mycobacterium sp. LB501T.


1974 ◽  
Vol 20 (10) ◽  
pp. 1297-1306 ◽  
Author(s):  
E. R. Blakley

A strain of Arthrobacter catabolizes cyclohexanecarboxylic acid by a pathway involving aromatization of the ring before its cleavage. The pathway includes the following intermediates: trans-4-hydroxycyclohexanecarboxylic acid, 4-ketocyclohexanecarboxylic acid, p-hydroxybenzoic acid, protocatechuic acid, and β-ketoadipic acid. The oxidation of 4-hydroxycyclohexanecarboxylic acid by cell extracts specifically requires NAD+ and results in the production of 4-ketocyclohexanecarboxylic acid. The latter compound is oxidized in the presence of a suitable electron acceptor, such as oxygen, methylene blue, or 2,6-dichlorophenolindophenol, to p-hydroxybenzoic acid.


1968 ◽  
Vol 110 (3) ◽  
pp. 491-498 ◽  
Author(s):  
P J Chapman ◽  
D J Hopper

1. Measurements of the rates of oxidation of various compounds by a fluorescent Pseudomonas indicated that metabolism of 2,4-xylenol was initiated by oxidation of the methyl group para to the hydroxyl group. 2. 4-Hydroxy-3-methylbenzoic acid was isolated as the product of oxidation of 2,4-xylenol by cells inhibited with αα′-bipyridyl. 3. 4-Hydroxyisophthalic acid accumulated at low oxygen concentrations when either 2,4-xylenol or 4-hydroxy-3-methylbenzoic acid was oxidized by cells grown with 2,4-xylenol. 4. When supplemented with NADH, but not with NADPH, cell extracts oxidized 4-hydroxy-3-methylbenzoic acid readily. 2-Hydroxy-5-methylbenzoic acid was not oxidized. 5. Both 4-hydroxyisophthalic acid and p-hydroxybenzoic acid were oxidized to β-oxoadipic acid by cell extracts supplemented with either NADH or NADPH. 4,5-Dihydroxyisophthalic acid was not oxidized. 6. From measurements of oxygen consumed and carbon dioxide evolved it was concluded that protocatechuic acid is an intermediate in the conversion of 4-hydroxyisophthalic acid into β-oxoadipic acid.


1998 ◽  
Vol 64 (2) ◽  
pp. 446-452 ◽  
Author(s):  
Tilmann Spiess ◽  
Frank Desiere ◽  
Peter Fischer ◽  
Jim C. Spain ◽  
Hans-Joachim Knackmuss ◽  
...  

ABSTRACT Mycobacterium sp. strain HL 4-NT-1, isolated from a mixed soil sample from the Stuttgart area, utilized 4-nitrotoluene as the sole source of nitrogen, carbon, and energy. Under aerobic conditions, resting cells of the Mycobacterium strain metabolized 4-nitrotoluene with concomitant release of small amounts of ammonia; under anaerobic conditions, 4-nitrotoluene was completely converted to 6-amino-m-cresol. 4-Hydroxylaminotoluene was converted to 6-amino-m-cresol by cell extracts and thus could be confirmed as the initial metabolite in the degradative pathway. This enzymatic equivalent to the acid-catalyzed Bamberger rearrangement requires neither cofactors nor oxygen. In the same crucial enzymatic step, the homologous substrate hydroxylaminobenzene was rearranged to 2-aminophenol. Abiotic oxidative dimerization of 6-amino-m-cresol, observed during growth of theMycobacterium strain, yielded a yellow dihydrophenoxazinone. Another yellow metabolite (λmax, 385 nm) was tentatively identified as 2-amino-5-methylmuconic semialdehyde, formed from 6-amino-m-cresol bymeta ring cleavage.


2011 ◽  
Vol 77 (18) ◽  
pp. 6606-6613 ◽  
Author(s):  
Dhan Prakash ◽  
Ravi Kumar ◽  
R. K. Jain ◽  
B. N. Tiwary

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.


2008 ◽  
Vol 190 (23) ◽  
pp. 7595-7600 ◽  
Author(s):  
Yan Huang ◽  
Randy Xun ◽  
Guanjun Chen ◽  
Luying Xun

ABSTRACT Pentachlorophenol (PCP) is a toxic pollutant. Its biodegradation has been extensively studied in Sphingobium chlorophenolicum ATCC 39723. All enzymes required to convert PCP to a common metabolic intermediate before entering the tricarboxylic acid cycle have been characterized. One of the enzymes is tetrachloro-p-hydroquinone (TeCH) reductive dehalogenase (PcpC), which is a glutathione (GSH) S-transferase (GST). PcpC catalyzes the GSH-dependent conversion of TeCH to trichloro-p-hydroquinone (TriCH) and then to dichloro-p-hydroquinone (DiCH) in the PCP degradation pathway. PcpC is susceptible to oxidative damage, and the damaged PcpC produces glutathionyl (GS) conjugates, GS-TriCH and GS-DiCH, which cannot be further metabolized by PcpC. The fate and effect of GS-hydroquinone conjugates were unknown. A putative GST gene (pcpF) is located next to pcpC on the bacterial chromosome. The pcpF gene was cloned, and the recombinant PcpF was purified. The purified PcpF was able to convert GS-TriCH and GS-DiCH conjugates to TriCH and DiCH, respectively. The GS-hydroquinone lyase reactions catalyzed by PcpF are rather unusual for a GST. The disruption of pcpF in S. chlorophenolicum made the mutant lose the GS-hydroquinone lyase activities in the cell extracts. The mutant became more sensitive to PCP toxicity and had a significantly decreased PCP degradation rate, likely due to the accumulation of the GS-hydroquinone conjugates inside the cell. Thus, PcpF played a maintenance role in PCP degradation and converted the GS-hydroquinone conjugates back to the intermediates of the PCP degradation pathway.


1964 ◽  
Vol 19 (9) ◽  
pp. 781-783 ◽  
Author(s):  
Hans Grisebach ◽  
Karl-Otto Vollmer

Further investigations on the biosynthesis of benzoic acids in Gaultheria procumbens L. have shown that besides salicylic acid all the other benzoic acids (gentisinic acid, p-hydroxybenzoic acid, protocatechuic acid, o-pyrocatechuic acid(?), syringic acid and vanillinic acid) can be formed from cinnamic acid. In the case of vanillinic acid it was proved that the total activity is located in the carboxyl group when cinnamic acid-[3-14C] is the precursor.Formiat-14C is incorporated into the methylester group of methylsalicylate.


2018 ◽  
Vol 13 (12) ◽  
pp. 1934578X1801301 ◽  
Author(s):  
Nguyen Quang Hung ◽  
Nguyen Thi Luyen ◽  
Nguyen The Cuong ◽  
Tran Huy Thai ◽  
Nguyen Thanh Tung ◽  
...  

A rare noriridoid and six known phenolic compounds were isolated from the parasite plant Rhopalocnemis phalloides. Using spectroscopic methods, these compounds were identified as 10-acetoxy- cis-2-oxabicyclo[4.3.0]nonan-7-en-3-one (1), p-hydroxybenzoic acid (2), protocatechuic acid (3), gallic acid (4), coniferyl aldehyde (5), l- O-trans-cinnamoyl-β-D-glucoside (6), and coniferin (7). The noriridoid compound is the first reported from the family Balanophoraceae. Of the isolated compounds, coniferyl aldehyde had the strongest inhibitory effect on nitric oxide production (IC50 = 8.24 μM).


1973 ◽  
Vol 28 (11-12) ◽  
pp. 662-674 ◽  
Author(s):  
Günther Schulz ◽  
Erich Hecker

Abstract The preparation of substituted cis,cis-muconic acids by oxidative ring scission of simple o-di-phenols with peracetic acid is investigated. Scission of pyrocatechol (1) to cis,cis-muconic acid (2) gives optimal yields, if acetic acid or ethyl acetate is used as solvent and if the solution is 15-20% with respect to sulfuric acid free peracetic acid comprising a one molar excess of oxidant. Under similar conditions, 3-tosylamino-pyrocatechol yields with peracetic acid the hitherto unknown α-tosylamino-cis,cis-muconic caid (18). 18 may be converted to α-tosylamino-traras,trans-muconic acid (19) by means of iodine, UV light or heating. From protocatechuic acid (4) under similar conditions not β-carboxy-cis,cis-muconic acid (5) is obtained, but rather β-carboxy-mucono-lactone (6 b, γ-carboxymethyl-β-carboxy-Δα-butenolide). As yet, this lactone has been accessible only from an isomer of β-carboxy-cis,cis-muconic acid, the latter being obtainable by enzymatic scission of protocatechuic acid (4). Steric effects are responsible for both, the formation of the free cis,cis-muconic acids 2 and 18 from pyrocatechol (1) and α-tosylamino-pyrocatechol, and the formation of the γ-lactone 6 b instead of β -carboxy-cis,cis-muconic acid by scission of protocatechuic acid (4). The time course of the reactions shows that - compared to pyrocatechol (1) - a 3-tosylamino-group enhances the peracetic acid scission, whereas a 4-carboxygroup as in 4 slows it down


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