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PubMed2000

Two distinct pathways for anaerobic degradation of aromatic compounds in the denitrifying bacterium Thauera aromatica strain AR-1.

Denitrifying bacteria degrade many different aromatic compounds anaerobically via the well-described benzoyl-CoA pathway. We have shown recently that the denitrifiers Azoarcus anaerobius and Thauera aromatica strain AR-1 use a different pathway for anaerobic degradation of resorcinol (1,3-dihydroxybenzene) and 3,5-dihydroxybenzoate, respectively. Both substrates are converted to hydroxyhydroquinone (1,2,4-trihydroxybenzene). In the membrane fraction of T. aromatica strain AR-1 cells grown with 3,5-dihydroxybenzoate, a hydroxyhydroquinone-dehydrogenating activity of 74 nmol min(-1)(mg protein)-1 was found. This activity was significantly lower in benzoate-grown cells. Benzoate-grown cells were not induced for degradation of 3,5-dihydroxybenzoate, and cells grown with 3,5-dihydroxybenzoate degraded benzoate only at a very low rate. With a substrate mixture of benzoate plus 3,5-dihydroxybenzoate, the cells showed diauxic growth. Benzoate was degraded first, while complete degradation of 3,5-dihydroxybenzoate occurred only after a long lag phase. The 3,5-dihydroxybenzoate-oxidizing and the hydroxyhydroquinone-dehydrogenating activities were fully induced only during 3,5-dihydroxybenzoate degradation. Synthesis of benzoyl-CoA reductase appeared to be significantly lower in 3,5-dihydroxybenzoate-grown cells as shown by immunoblotting. These results confirm that T. aromatica strain AR-1 harbors, in addition to the benzoyl-CoA pathway, a second, mechanistically distinct pathway for anaerobic degradation of aromatic compounds. This pathway is inducible and subject to catabolite repression by benzoate.

Acyl Coenzyme A↗

PubMed1990

Regulation of glutathione S-transferase Ya subunit gene expression: identification of a unique xenobiotic-responsive element controlling inducible expression by planar aromatic compounds.

We have identified a region in the 5' flanking sequence of the glutathione S-transferase (RX:glutathione R-transferase, EC 2.5.1.18) Ya subunit gene that contains a unique xenobiotic-responsive element (XRE). The regulatory region spans nucleotides -722 to -682 of the 5' flanking sequence and is responsible for part of the basal level as well as inducible expression of the Ya subunit gene by planar aromatic compounds such as beta-naphthoflavone (beta-NF) and 3-methyl-cholanthrene. The DNA sequence of this region (beta-NF-responsive element) is distinct from the DNA sequence of the XRE found in the cytochrome P-450 IA1 gene. In addition to the region containing the beta-NF-responsive element, two other regulatory regions of the Ya subunit gene have been identified. One region spans nucleotides -867 to -857 and has a DNA sequence with identity to the hepatocyte nuclear factor 1 recognition motif found in several liver-specific genes. The second region spans nucleotides -908 to -899 and contains a DNA sequence with identity to the XRE found in the cytochrome P-450 IA1 gene. The XRE sequence also contributes to part of the responsiveness of the Ya subunit gene to planar aromatic compounds. Our data suggest that regulation of gene expression by planar aromatic compounds can be mediated by a DNA sequence that is distinct from the XRE sequence.

Base Sequence↗

PubMedDate not supplied

[Bacillus gordonae sp. nov., a new species belonging to the second morphological group, degrading various aromatic compounds].

Thirty strains were isolated from pasteurized soil samples by enrichment culture in aerobiosis at 32 degrees C in a minimal medium containing one of the following compounds as sole source of carbon and energy: quinate, p-hydroxybenzoate, phthalate, isophthalate or trimellitate. These bacteria were rods (0.8 X 2-7 micron), motile by peritrichous flagella. Endospores were oval (1.4-1.8 X 2 micron) and distinctly swelled the sporangia. The Gram reaction was variable but the Gram type was positive. Colonies were smaller on peptone (0.4%) agar than on minimal salts-glucose (0.2%) agar. The following characters were always present: growth in the presence of lysozyme, cytochrome c oxidase, catalase, nitrate assimilation, urease, amylase and L-glutamate dehydrogenase. The cells contained glycogen. In anaerobiosis, glucose was not fermented and nitrate was not used as a respiratory acceptor of electrons. Of 215 substrates tested, 31 (including 9 aromatic compounds) were used as sole carbon and energy sources by all 30 strains, and 38 substrates (including 13 aromatic compounds) were used by only some of them; 146 substrates (including 49 aromatic compounds) were not used by any of the 30 strains. No amino acid could be used as sole carbon and energy source. Numerical analysis of the 30 strains showed an aggregate cluster made of 5 phena. The mean G + C content of the DNA was 55 +/- 0.6 mol %. The described bacteria are clearly different from the 2 known species of the second morphological group which cannot ferment carbohydrates: Bacillus brevis and B. azotoformans. Strain Q1 (ATCC 29948) is the holotype of Bacillus gordonae sp. nov.

Bacillus↗

PubMed2006

Reductive dechlorination of polychlorinated biphenyls as affected by natural halogenated aromatic compounds.

We investigated the effects of halogenated aromatic compounds (HACs) including naturally occurring ones (L-thyroxine, 3-chloro-L-tyrosine, 5-chloroindole, 2-chlorophenol, 4-chlorophenol and chlorobenzene) on polychlorinated biphenyl (PCB) dechlorination in sediment cultures. A PCB-dechlorinating enrichment culture of sediment microorganisms from the St. Lawrence River was used as an initial inoculum. When the culture was inoculated into Aroclor 1248 sediments amended with each of the six HACs, the extent of dechlorination was not enhanced by amendment with HACs. The dechlorination patterns in the HAC-amended sediments were nearly identical to that of the HAC-free sediments except the 3-chloro-L-tyrosine-amended ones where no dechlorination activity was observed. When these sediment cultures were transferred into fresh sediments with the same HACs, the dechlorination specificities remained the same as those of the initial inoculations. Thus, in the present study, the substrate range of the highly selected enrichment culture could not be broadened by the HACs. It appears that HACs affect PCB dechlorination mainly through population selection rather than enzyme induction of single population.

Aroclors↗

PubMed2004

Production of laccase isoforms by Pleurotus pulmonarius in response to presence of phenolic and aromatic compounds.

The effect of several phenolic and aromatic monomers structurally-related to lignin on production of laccase by the white rot fungus P. pulmonarius (Fr.) Quélet has been studied. In the absence of an inducer, laccase was maximally produced after depletion of carbon and nitrogen sources. Among 15 phenolic and aromatic compounds tested, ferulic acid and vanillin were the most efficient inducers, increasing the production of laccase activity up to 10 times. A mixture of ferulic acid and vanillin was more efficient to induce the production of laccase than the isolated phenolics. At least three laccase isoforms designated as lcc1, lcc2 and lcc3 were identified by eletrophoretic analysis of P. pulmonarius culture filtrates. The lcc1 and lcc2 isoforms were produced by non-induced cultures, while lcc3 was found only in induced-culture filtrates.

Benzaldehydes↗

PubMed1970

Contribution of aromatic residue interactions to the stability of myoglobin. V. Enhancement by aromatic compounds of the rate of heat denaturation.

Aromatic compounds like chlorpromazine and benzoate and its homologs strongly enhance the rate of heat denaturation of myoglobin. The latter apparently exert their action by complexing with a single kind of site in the hemeprotein. Both charge-transfer and hydrophobic interactions are implicated in complex formation, most probably with the heme moiety.

Animals↗

PubMedDate not supplied

Polycyclic aromatic compounds: extraction and determination in food.

Polycyclic aromatic hydrocarbons (PAHs) and polycyclic aromatic compounds (PACs) in general, comprise the largest class of known environmental carcinogens. Reports of some studies of total diet in a number of developed countries indicate that food constitutes an important source of exposure of man to PACs, although other authors have shown the need to develop accurate data, in order that the overall public health hazard may be effectively evaluated and controlled. In this context, this review aims to give an overview of methods used to determine the PAC content of foodstuffs. At first, the nature, classification and derived compounds of PAHs are considered. Likewise, the occurrence of PAHs in processed and in non-processed foods is shown. The main causes are environmental contamination and the utilization of procedures which give rise to the presence of PACs during the processing, preservation, and packaging of foods. Octanol: water partition coefficients of PACs and their relationships with some properties, such as aqueous solubility and bioaccumulation, are considered. The solubility of complex mixtures of PACs in several organic solvents and the different methods for extraction and isolation of the PAC-fraction from foodstuffs are reviewed. The methodologies used for the separation, identification and quantitative determination also are briefly considered.

Chromatography↗

PubMed1971

Dissimilation of aromatic compounds by Alcaligenes eutrophus.

The range of aromatic compounds that support the growth of Alcaligenes eutrophus has been determined, and the pathways used for the dissimilation of these substrates have been explored, largely by enzymatic analyses. The beta-ketoadipate pathway operates in the dissimilation of benzoate and p-hydroxybenzoate; the genetisate pathway, in the dissimilation of m-hydroxybenzoate; and the meta cleavage pathway, in the dissimilation of phenol and p-cresol. l-Tryptophan is oxidized via anthranilate; but the metabolic fate of anthranilate was not established. The metabolism of the three stereoisomers of muconic acid was also examined.

Adipates↗

PubMed2005

Uptake of cycloalkanes and bicyclic aromatic compounds by ion-exchange resins from aqueous solutions.

The uptakes of cycloalkanes (C5 - C8) and bicyclic aromatic compounds (naphthalene, biphenyl, and azulene) by both strong acid cation (Dowex 50W-X4 and X8) and strong base anion (Dowex 1-X4 and X8) exchange resins have been studied in aqueous solutions at 25 degrees C; their distribution constants (K) have been determined. The relationship between the octanol-water partition coefficient and the resin affinity for solutes has been analyzed. The K values of three aromatic compounds were found to be much higher than expected from the octanol-water partition coefficients. This is probably due to the pi interaction of aromatic rings with the resin matrix. Microscopic observations revealed that azulene molecules are uniformly distributed inside a resin particle.

Journal Article↗

PubMed2004

The Pseudomonas putida Crc global regulator controls the expression of genes from several chromosomal catabolic pathways for aromatic compounds.

The Crc protein is involved in the repression of several catabolic pathways for the assimilation of some sugars, nitrogenated compounds, and hydrocarbons in Pseudomonas putida and Pseudomonas aeruginosa when other preferred carbon sources are present in the culture medium (catabolic repression). Crc appears to be a component of a signal transduction pathway modulating carbon metabolism in pseudomonads, although its mode of action is unknown. To better understand the role of Crc, the proteome profile of two otherwise isogenic P. putida strains containing either a wild-type or an inactivated crc allele was compared. The results showed that Crc is involved in the catabolic repression of the hpd and hmgA genes from the homogentisate pathway, one of the central catabolic pathways for aromatic compounds that is used to assimilate intermediates derived from the oxidation of phenylalanine, tyrosine, and several aromatic hydrocarbons. This led us to analyze whether Crc also regulates the expression of the other central catabolic pathways for aromatic compounds present in P. putida. It was found that genes required to assimilate benzoate through the catechol pathway (benA and catBCA) and 4-OH-benzoate through the protocatechuate pathway (pobA and pcaHG) are also negatively modulated by Crc. However, the pathway for phenylacetate appeared to be unaffected by Crc. These results expand the influence of Crc to pathways used to assimilate several aromatic compounds, which highlights its importance as a master regulator of carbon metabolism in P. putida.

Bacterial Proteins↗

PubMed2005

Significance of cytochrome P450 system responses and levels of bile fluorescent aromatic compounds in marine wildlife following oil spills.

The relationships among cytochrome P450 induction in marine wildlife species, levels of fluorescent aromatic compounds (FAC) in their bile, the chemical composition of the inducing compounds, the significance of the exposure pathway, and any resulting injury, as a consequence of exposure to crude oil following a spill, are reviewed. Fish collected after oil spills often show increases in cytochrome P450 system activity, cytochrome P4501A (CYP1A) and bile fluorescent aromatic compounds (FAC), that are correlated with exposure to polycyclic aromatic hydrocarbons (PAH) in the oil. There is also some evidence for increases in bile FAC and induction of cytochrome P450 in marine birds and mammals after oil spills. However, when observed, increases in these exposure indicators are transitory and generally decrease to background levels within one year after the exposure. Laboratory studies have shown induction of cytochrome P450 systems occurs after exposure of fish to crude oil in water, sediment or food. Most of the PAH found in crude oil (dominantly 2- and 3-ring PAH) are not strong inducers of cytochrome P450. Exposure to the 4-ring chrysenes or the photooxidized products of the PAH may account for the cytochrome P450 responses in fish collected from oil-spill sites. The contribution of non-spill background PAH, particularly combustion-derived (pyrogenic) PAH, to bile FAC and cytochrome P450 system responses can be confounding and needs to be considered when evaluating oil spill effects. The ubiquity of pyrogenic PAH makes it important to fully characterize all sources of PAH, including PAH from natural resources, e.g. retene, in oil spill studies. In addition, such parameters as species, sex, age, ambient temperature and season need to be taken into account. While increases in fish bile FAC and cytochrome P450 system responses, can together, be sensitive general indicators of PAH exposure after an oil spill, there is little unequivocal evidence to suggest a linkage to higher order biological effects, e.g. toxicity, lesions, reproductive failure.

Animals↗

PubMed2002

Mineralization of aromatic compounds by brown-rot basidiomycetes - mechanisms involved in initial attack on the aromatic ring.

Benzaldehyde and its metabolic intermediates were effectively degraded by the brown-rot basidiomycetes Tyromyces palustris and Gloeophyllum trabeum. The pathway of benzaldehyde degradation was elucidated by the identification of fungal metabolites produced upon the addition of benzaldehyde and its metabolic intermediates. The oxidation and reduction occurred simultaneously, forming benzyl alcohol and benzoic acid as major products. Hydroxylation reactions, which seemed to be a key step, occurred on benzaldehyde and benzoic acid, but not on benzyl alcohol, to form corresponding 4-hydroxyl and 3,4-dihydroxyl derivatives. 1-Formyl derivatives were oxidized to 1-carboxyl derivatives at several metabolic stages. All of these reactions resulted in the formation of 3,4-dihydroxybenzoic acid. This was further metabolized via the decarboxylation reaction to yield 1,2,4-trihydroxybenzene, which may be susceptible to the ring-fission reaction. Ring-U-14C-labelled benzaldehyde and benzoic acid were effectively mineralized, clearly indicating that the brown-rot basidiomycetes are capable of metabolizing certain aromatic compounds to CO2 and H2O, despite the fact that brown-rot fungi cannot degrade polymeric lignin. Inhibitor experiments, using hydroxyl radical scavengers, catalase and cytochrome P450 inhibitors, strongly suggested that the aromatic hydroxylation reactions found in the brown-rot fungi are catalysed by intracellular enzyme(s), but not by Fenton-reaction-derived hydroxyl radicals.

Basidiomycota↗

PubMed2006

Lewis acid-catalyzed [4 + 2] benzannulation between enynal units and enols or enol ethers: novel synthetic tools for polysubstituted aromatic compounds including indole and benzofuran derivatives.

The reaction of enynals 1, including o-(alkynyl)benzaldehydes, and carbonyl compounds 2, such as aldehydes and ketones, in the presence of a catalytic amount of AuBr3 in 1,4-dioxane at 100 degrees C gave the functionalized aromatic compounds 3 in high yields. Similarly, the AuBr3-catalyzed reactions of 1 with acetal compounds 5 afforded the corresponding aromatic compounds 3 in good yields. On the other hand, when the reaction was carried out in the presence of a catalytic amount of Cu(NTf2)2 and 1 equiv of H2O in (CH2Cl)2 at 100 degrees C, the decarbonylated naphthalene products 4 were obtained selectively over 3. Benzofused heteroaromatic compounds, such as indole derivatives 13 and benzofuran derivatives 15, were also synthesized by using the present benzannulation methodology.

Aldehydes↗

PubMed2005

Anaerobic degradation of aromatic compounds by magnetospirillum strains: isolation and degradation genes.

Four Magnetospirillum strains degrading toluene, phenol, benzoate, and other aromatic compounds under anaerobic conditions were isolated from denitrifying enrichment cultures. One of the isolates, toluene-degrading strain TS-6, contained genes that are homologous to those encoding benzylsuccinate synthase (Bss) and benzoyl-CoA reductase (Bcr), two key enzymes of anaerobic toluene and benzoate degradation respectively in known denitrifying bacteria. Transcription of the genes was confirmed. It was controlled by growth substrates and oxygen conditions, but bcr genes were unexpectedly expressed in aerobic cells grown on benzoate. It was confirmed that the genus Magnetospirillum represents the third genus of denitrifying bacteria capable of degrading aromatic compounds under anaerobic conditions, besides the genera Thauera and Azoarcus.

Anaerobiosis↗

PubMed2000

Development of a hollow waveguide sampler for detection of chlorinated aromatic compounds in soils.

In this paper, a Fourier transform infrared (FT-IR) spectroscopic method for detection of chlorinated aromatic compounds in soils was developed. The sensing device of this method was based on an infrared hollow waveguide, the inner surface of which was coated with a hydrophobic film. Vaporized chlorinated aromatic compounds from soils were trapped onto the hydrophobic film of the hollow waveguide sampler following detection by FT-IR spectrometry. The extraction process in this method was similar to the headspace solid-phase microextraction (HSSPME) in principle. Means of increasing the speed of transfer of the vaporized organic species to the sampler were also studied. Results indicated that, with a negative pressure on the end of the sampler, the speed of transfer increased significantly. Vapor pressures of the analytes were used as an indication to test the limitation of this method in the analysis of organic compounds in soils. Results showed that analytes with vapor pressures lower than 12 Torr could be detected quantitatively. The typical R-square of the regression on the concentration and IR signals was around 0.99 and the typical detection limits were in the range of hundreds of parts per billion.

Hydrocarbons, Aromatic↗

PubMedDate not supplied

Liquid chromatographic determination of vanillin and related aromatic compounds.

This paper describes a reversed-phase liquid chromatographic method for the determination of vanillin, associated natural aromatic compounds and/or synthetic precursors, ethyl vanillin, and coumarin, a commonly encountered adulterant in nonbeverage and beverage alcohol products using a ternary gradient mobile phase. The compounds were separated on a Nova-Pak C18 column by using water, methanol, and tetrahydrofuran as the mobile phase. Measurements were made by using a photodiode array detector at 275 nm. The choice of the mobile phase and the column provides baseline resolution of vanillin and the associated aromatic compounds commonly found in vanilla-flavoring material. Because this method provides low-level detection/quantitation, it is suitable for the characterization of vanilla flavoring materials that are currently added to vanilla flavored beverage alcohol products.

Alcoholic Beverages↗

PubMed1972

Use of aromatic compounds for growth and isolation of Zoogloea.

Nine Zoogloea strains, were examined for their ability to utilize 35 aromatic compounds. Benzoate, m-toluate, and p-toluate, as well as phenol, o-cresol, m-cresol, and p-cresol, were utilized by eight strains. These strains exhibited meta cleavage of catechol and of methyl-substituted catechols. With the exception of L-tyrosine, none of the aromatic compounds tested supported growth of Z. ramigera ATCC 19623. A medium containing sodium m-toluate was used to isolate 37 zoogloea-forming bacteria from various polluted environments. The isolates were identified as strains of Zoogloea.

Bacteriological Techniques↗

PubMed2006

Resonance-enhanced multiphoton ionization time-of-flight mass spectrometry for detection of nitrogen containing aliphatic and aromatic compounds: resonance-enhanced multiphoton ionization spectroscopic investigation and on-line analytical application.

Resonance-enhanced multiphoton ionization (REMPI) combined with time-of-flight mass spectrometry (TOFMS) is an analytical method capable of on-line monitoring of trace compounds in complex matrices. A necessary prerequisite for substance selective detection is spectroscopic investigation of the target molecules. Several organic nitrogen compounds comprising aliphatic and aromatic amines, nitrogen heterocyclic compounds, and aromatic nitriles are spectroscopically investigated with a tunable narrow bandwidth optical parametric oscillator (OPO) laser system providing a scannable wavelength range between 220 and 340 nm. These species are known as possible precursors in fuel-NO formation from combustion of solid fuels such as biomass and waste. A newly conceived double inlet system was used in this study, which allows rapid change between effusive and supersonic molecular beams. The resulting REMPI spectra of the compounds are discussed with respect to electronic transitions that could be utilized for a selective ionization of these compounds in complex mixtures such as combustion and process gases. The practicability of this approach is demonstrated by wavelength selected on-line REMPI-TOFMS detection of aniline and cyanonaphthalene in the burning chamber of a waste incineration plant. REMPI mass spectra recorded at different excitation wavelengths as well as variations in time show the utilization of species-selective REMPI-TOFMS detection for on-line monitoring of crucial substances in pollutant formation.

Air Pollutants↗