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PubMed1995

Metabolism of halohydroquinones in Rhodococcus chlorophenolicus PCP-1.

The actinomycete Rhodococcus chlorophenolicus PCP-1 metabolizes pentachlorophenol into ultimate inorganic end products via tetrachloro-p-hydroquinone. This intermediate was further dehalogenated in the cytoplasm requiring reductant in the cell free system. Tetrafluoro-p-hydroquinone and tetrabromo-p-hydroquinone were also dehalogenated. Chlorophenol analogs, thiol blocking agents and molecular oxygen inhibited the activity. The dehalogenating reactions led to 1,2,4-trihydroxybenzene, which was further metabolized into maleic acid.

Biodegradation, Environmental↗

PubMed1993

Catabolism of benzene compounds by ascomycetous and basidiomycetous yeasts and yeastlike fungi. A literature review and an experimental approach.

A literature review is given on growth of yeasts on benzene compounds and on the catabolic pathways involved. Additionally, a yeast collection was screened for assimilation of phenol and 3-hydroxybenzoic acid. Fifteen ascomycetous and thirteen basidiomycetous yeast species were selected and were tested for growth on 84 benzene compounds. It appeared that 63 of these compounds supported growth of one or more yeast species. The black yeast Exophiala jeanselmei assimilated 54 of these compounds. The catechol branch of the 3-oxoadipate pathway and its hydroxyhydroquinone variant were involved in phenol and resorcinol catabolism of ascomycetes as well as of basidiomycetes. However, these two groups of yeasts showed characteristic differences in hydroxybenzoate catabolism. In the yeastlike fungus E. jeanselmei and in basidiomycetes of the genera Cryptococcus, Leucosporidium and Rhodotorula, the protocatechuate branch of the 3-oxoadipate pathway was induced by growth on 3- and 4-hydroxybenzoic acids. In three Trichosporon species and in all ascomycetous yeasts tested, 4-hydroxybenzoic acid was catabolyzed via protocatechuate and hydroxyhydroquinone. These yeasts were unable to cleave protocatechuate. 3-Hydroxybenzoic and 3-hydroxycinnamic acids were catabolized in ascomycetous yeasts via the gentisate pathway, but in basidiomycetes via protocatechuate. Incomplete oxidation of phenol, some chlorophenols, cresols and xylenols was observed in cultures of Candida parapsilosis growing on hydroquinone. Most compounds transformed by the growing culture were also converted by the phenol monooxygenase present in cell-free extracts of this yeast. They did not support growth. The relationship between the ability of ascomycetous yeasts to assimilate n-alkanes, amines and benzene compounds, and the presence of Coenzyme Q9 is discussed.

Ascomycota↗

PubMed1990

Biotransformation of alkyl and aryl carbonates. Microbial degradation.

An enriched mixed culture was successfully grown on model alkyl and aryl carbonates. These compounds were degraded by microorganisms at different rates. P-Chlorophenyl-2-octyl carbonate and p-nitrobenzyl-2-octyl carbonate were metabolized through the formation of p-chlorophenol and p-nitrobenzyl alcohol respectively. A strain of Acinetobacter calcoaceticus isolated from the mixed culture utilized phenyl-2-octyl carbonate by an intracellular hydrolase to phenol and 2-octanol which were further metabolized.

Acinetobacter↗

PubMed1981

Influence of pH on the toxicity of substituted phenols to fish.

The 96-hr LC50 values of six chloro-, bromo-, and nitro- substituted phenols to the guppy (Poecilia reticulata Peters) were determined by a semistatic method in the pH range of 5 to 8. The pH did not affect appreciably the toxicity of 4-chlorophenol, which is primarily nonionized over the whole range, but the toxicity of more acidic phenols decreased as the pH increased. The changes in toxicity were substantially smaller than they would be, if only the nonionized phenol form were toxic. The results could be explained by assuming that the phenate ion also contributes to the toxicity, but its molar toxicity decreases with rising pH.

Animals↗

PubMed1980

Photodecomposition of DDA.

The photodecomposition of aqueous solutions of 2,2-bis (p-chlorophenyl) acetic acid (DDA) was slow in sunlight and rapid in the laboratory, producing p,p'-dichlorobenzophenone (DCB), p-chlorobenzaldehyde, p-chlorophenol, and several unidentified polar products. p,p'-Dichlorobenzilic acid, and p,p'-dichlorobenzhydrol gave rise to the same photoproducts, while bis-(p-chlorophenyl) methane (DDM) and chlorogenzilate were converted only to DCB. DCB and p-chlorogenzaldehyde proved to be resistant to photodegradation but gradually produced p-chlorobenzoic acid which, in turn, formed p-hydroxybenzoic and benzoic acids, probably the last environmentally detectable links in the long chain of DDT degradation to CO2 and water. High pressure liquid chromatography (HPLC) proved to be ideal for separating and quantitating the parent compounds and their photoproducts directly from the aqueous photolysates or from methanol solutions of the isolates and standards.

Chromatography, Gas↗

PubMed1980

Toxicology of various pesticides and their decomposition products on mitochondrial electron transport.

The effect of various pesticides and derivatives on mitochondrial electron transport systems was assessed. DDT, DDE, TDE, Kelthane, chlorobenzilate, chloropropylate and Acarol were found to be inhibitory towards both heavy beef heart mitochondrial (HBHM) NADH-oxidase and succinoxidase enzyme systems. Dichlorobenzophenone and p-chlorophenol were less inhibitory towards the HBHM NADH-oxidase and did not inhibit the succinoxidase enzyme system. DDA did not inhibit either of the electron transport systems. Carbaryl was not inhibitory towards both HBHM oxidase systems, whereas its degradative product dihydroxynaphthalene was inhibitory at the same concentration. Furadan, Matacil, Baygon and Dimetilan were only slightly inhibitory towards themitochondrial NADH-oxidase system and did not inhibit the succinoxidase system. Zectran was inhibitory towards the NADH-oxidase system and was not inhibitory towards the succinoxidase system. DDT, DDE and TDE, dihydroxynaphthalene and 1-naphthol inhibited the NADH-oxidase enzyme system onthe substrate side of cytochrome c, whereas Kelthane inhibited on the oxygen side.

Animals↗

PubMed1981

Perturbation of lipid membranes by organic pollutants.

The ability of a range of organic pollutants--hexachlorobenzene, mirex(1,1a,2,2,3,3a,4,5,5,5a,5b,6-dodecachlorooctahydro-1,3,4-metheno-1H cyclobuta(cd) pentalene), 1,3,5-trichlorobenzene, 2,4,6-trichlorophenol, p-nitrophenol, p-chlorophenol, DDT, and pentachlorophenol--to perturb liposomes of dipalmitoyl phosphatidylcholine (DPPC) has been measured by differential scanning calorimetry. The degree of perturbation was measured by the increase in breadth of the main DPPC phase transition in both heating and cooling scans. DDT and the phenol derivatives were effective perturbers of phospholipid, broadening the transition by as much as 12-fold. Hexachlorobenzene and mirex did not perturb at all when mixed with DPPC at concentrations as high as 20 mol%, although 1,3,5-trichlorobenzene caused slight broadening of the main transition at this concentration. Perturbation is facilitated by the presence of a hydroxyl group on the benzene ring and hindered by increasing degrees of chloride substitution. An apparent correlation exists between the extent of phospholipid perturbation measured by differential scanning calorimetry and LD50 values for these compounds taken from the literature. This suggests the possibility of formulating an "index of perturbation" which could be used to screen certain classes of organic compounds for potential biological toxicity on a routine basis.

Animals↗

PubMed1979

Vapor and liquid phase photolysis of the n-butyl ester of 2,4-dichlorophenoxyacetic acid.

The n-butyl ester of 2,4-dichlorophenoxyacetic acid in the liquid and vapor phase was irradiated in a pyrex reactor for 188 hr by ultraviolet light of 300 nm using an intensity similar to that around 300 nm in the solar spectrum. In both phases, the ester was dechlorinated at the ortho position together with simultaneous reduction and Photo-Fries rearrangement to produce volatile photoproducts. Ether bond cleavage to produce chlorophenols, and a Norrish Type II photoprocess, also occurred. A 79% mass balance was accounted for by volatile chlorinated organic residues. HCL gas was also evolved. The production of Cl was also demonstrated in both vapor and liquid phases. The half time of decomposition was around 13 days. The possible effects of the volatile photoproducts on off-target plants were also noted.

2,4-Dichlorophenoxyacetic Acid↗

PubMed1991

The acute and chronic toxicity of ten chlorinated organic compounds to the American flagfish (Jordanella floridae).

The acute toxicity (96-hr median lethal concentrations (LC50s) of ten chlorinated isomers of benzene, phenol, ethane, and ethylene to the American flagfish (Jordanella floridae) were determined in both static and flow-through systems. Chronic toxicity to embryo-larval fish was also estimated from hatching success and post-hatch survival as well as fry growth rates and survival. Maximum acceptable toxicant concentrations (MATC) were estimated where possible. In general, for both acute and chronic toxicity tests, the order of increasing relative toxicity based on the water-borne exposure concentrations was: chloroethanes, chloroethylenes, chlorobenzenes, and chlorophenols. Within groups, more highly chlorinated isomers were usually more toxic. The presence of suspended or colloidal 1,2,4,5-tetrachlorobenzene was observed in acute toxicity testing and affected toxicity estimates.

Animals↗

PubMed1995

Internal exposure of waste incineration workers to organic and inorganic substances.

One hundred and twenty-two persons employed in an industrial waste incineration plant were examined with respect to organic and inorganic substances which may be produced during the combustion of different waste. The employees were divided into three groups: persons with contact with the incinerator (WI workers, n = 45), periphery workers (n = 54) and management (n = 23). For the evaluation of internal exposure, the levels of lead, cadmium, mercury, benzene, toluene, ethylbenzene and m-xylene in blood, chromium in the erythrocytes, polychlorinated biphenyls, hexachlorobenzene and pentachlorophenol in plasma, and arsenic, chromium, nickel, vanadium, chlorophenols and hydroxypyrene in urine were determined. The internal exposures of the three groups were tested against each other and were compared with the reference values of the general population. Differences between the groups investigated were tested using the U test according to Wilcoxon, Mann and Whitney (P < 0.05). The biological exposure limits valid in Germany (BAT values) were not exceeded in any cases. Compared with the background levels of the German population, certain parameters were exceeded in several employees. Significantly higher levels of the WI workers in comparison to both periphery workers and management were found for toluene in blood (median: 1.1 vs 0.9 vs 0.6 microgram/l). For the lead and cadmium levels in blood and for the urinary excretion of arsenic, 2,4-dichlorophenol and tetrachlorophenols, statistical differences were found only between WI workers and one of the other groups. However, in all cases the elevations were very small and of interest more from the environmental than from the occupational point of view. It must be stressed that this waste incineration plant is very modern in terms of worker health and safety. At older plants without corresponding health and safety measures, higher internal exposure of the employees to hazardous substances may exist.

Adult↗

PubMed1991

Interactions of halogenated industrial chemicals with transthyretin and effects on thyroid hormone levels in vivo.

Previous results in experimental systems have suggested that hydroxylated PCBs may decrease thyroid hormone levels through associative interaction with transthyretin. In the present paper it was investigated whether this property was also shared by various industrial chemicals, mainly pesticides. In total, 65 compounds from 12 chemical groups were analyzed for direct interference with the T4 binding site of transthyretin using a competitive binding assay. Sixty per cent of the compounds were competitive at a concentration level of 100 microM. Relatively strong interactions were observed by several chlorophenols, chlorophenoxy acids and nitrophenols, as well as by individual compounds such as hexachlorobenzene, dicofol, bromoxynil and tetrachlorohydroquinone. Examples from these chemical groups, e.g. pentachlorophenol, 2,4-dichlorophenoxybutyric acid, dinoseb and bromoxynil, also reduced plasma TT4 levels in rats. In addition, bromoxynil decreased plasma TT3 levels. The results suggest the existence of a number of halogenated industrial chemicals with a potential for lowering plasma thyroid hormone levels through interference with hormone transport carriers.

Animals↗

PubMed1991

Identification of urinary metabolites in rats treated with p-chloronitrobenzene.

Urinary metabolites in rats treated with p-chloronitrobenzene were identified by gas chromatography-mass spectrometry. A single dose of 100 mg/kg body wt p-chloronitrobenzene was administered intraperitoneally to male Sprague-Dawley rats and urine samples were collected from the 8th to 24th hour after the administration. Urinary metabolites were extracted with diethylether at pH 1.0 and pH 10.0 from urine samples hydrolyzed with acid and base and from intact urine samples. Aliquots of the ethereal extracts were injected into a gas chromatograph-mass spectrometer. Nine substances were identified: p-chloroaniline, 2,4-dichloroaniline, p-nitrothiophenol, 2-chloro-5-nitrophenol, 2-amino-5-chlorophenol, p-chloroformanilide, 4-chloro-2-hydroxyacetanilide, a small amount of p-chloroacetanilide and traces of unchanged p-chloronitrobenzene.

Animals↗

PubMed1984

Hydrocarbon transport in chylomicrons and high-density lipoproteins in rat.

A lipoprotein system is described that transports gut hydrocarbons of low polarity in chylomicrons of intestinal lymph and plasma to plasma high density lipoproteins (HDL) in rat. Four highly lipophilic aryl and alkyl hydrocarbons [benzo(alpha)pyrene; 1,1,1-trichloro-2,2-bis(p-chlorophenol)ethane (DDT), hexadecane and octadecane] were selected to give a graded range of polarity. Chylomicrons were labeled doubly with radioisotopes in triacylglycerol and a single hydrocarbon by feeding [3H]-glycerol and [14C]hydrocarbon. All hydrocarbons were transported in the triacylglycerol oil phase of chylomicrons. Injected chylomicron triacylglycerol and 3 of 4 hydrocarbons were cleared simultaneously from plasma consistent with lipoprotein-lipase dependent hydrocarbon clearance but DDT was cleared more rapidly. HDL was the major plasma acceptor of all labelled hydrocarbons. Plasma chemical fluxes were measured for octadecane and DDT and both showed net fluxes from chylomicrons to HDL. HDL selectively concentrated chylomicron hydrocarbons from chylomicron triacylglycerol. Lipoprotein lipase stimulation by intravenous heparin significantly increased transfer of alkanes from chylomicrons to HDL. These results indicate that (a) chylomicrons transport gut-derived hydrocarbons with a wide range of structure and polarity as triacylglycerol solutes; (b) HDL are a major plasma acceptor of all these hydrocarbons, demonstrating both selective solute uptake from triacylglycerol and net chemical uptake for the 2 hydrocarbons studied and (c) efflux of these chylomicron hydrocarbons from plasma and into HDL is regulated partly by hydrolysis of chylomicron triacylglycerol.

Alkanes↗

PubMed1999

Influence of He-Ne laser irradiation of soybean seeds on seed mycoflora, growth, nodulation, and resistance to Fusarium solani.

Laser irradiation of soybean seeds for 3 min caused a clear reduction in the number of seed-borne fungi which became more pronounced as the irradiation time was extended. Pretreatment of the seeds with methylene blue, methyl red and carmine enhanced the effect of laser. Rhizoctonia solani, Alternaria tenuissima, Cercospora kikuchii and Colletotrichum truncatum were completely eliminated when the seeds were pretreated with a dye and irradiated for 10 min. Seed germination was stimulated on exposure of the seed to 1-min irradiation. At such dose, most of the dyes were accelerators while the higher doses were inhibitory to seed germination. Chlorophyll a, chlorophyll b and carotenoid content of developed plants differed, depending on the irradiation dose and dye treatment of the seeds. In seeds irradiated for 1 or 3 min, chlorophyll a formation was less affected than chlorophyll b formation. In seeds irradiated for 10 min, both the chlorophyll contents were decreased especially in the presence of some applied dyes. On the other hand, there was an increase in carotenoid content of soybean leaves when the laser dose increased. The number and dry mass of nodules were mostly greater (as compared to the corresponding control), when the seeds irradiated for 1 or 3 min were pretreated with methyl red, chlorophenol red, crystal violet and methylene blue. Irradiation of pre-sowing seeds greatly protected soybean stands against F. solani. The disease incidence differed somewhat when the irradiated seeds were pretreated with dyes. The reduction in disease incidence was accompanied by accumulation of high proline and phenol levels in the infected root tissues of soybean, suggesting that these compounds have a certain role in the prevention of disease development.

Food Microbiology↗

PubMed2003

Synthesis of 5-chloro-3-[4-(3-diethylaminopropoxy)benzoyl]-2-(4-methoxyphenyl)benzofuran as a beta-amyloid aggregation inhibitor.

An efficient synthesis of 5-chloro-3-[4-(3-diethylaminopropoxy)benzoyl]-2-(4-methoxyphenyl)benzofuran (8), a potent beta-amyloid aggregation inhibitor, is described. 5-Chloro-2-(4-methoxyphenyl)benzofuran (3) was obtained by the one-pot synthesis of 4-chlorophenol with omega-(methylsulfinyl)-p-methoxyacetophenone (1) under Pummerer reaction conditions, and it was followed by the desulfurization of the resultant 5-chloro-3-methylthio-2-(4-methoxyphenyl)benzofuran (2e). Acylation of benzofuran 3 with 4-(3-bromopropoxy)benzoyl chloride (6) gave the ketone 7, which was converted into compound 8 by the treatment of diethylamine.

Amyloid beta-Peptides↗

PubMed1994

Synthesis of trans unsaturated fatty acids in Pseudomonas putida P8 by direct isomerization of the double bond of lipids.

The phospholipids of Pseudomonas putida P8 contain monounsaturated fatty acids in the cis and trans configuration. Cells of this phenol-degrading bacterium change the proportions of these isomers in response to the addition or elimination of a membrane active compound such as 4-chlorophenol. This study undoubtedly reveals that the cis unsaturated fatty acids are directly converted into trans isomers without involvement of de novo synthesis of fatty acids. Oleic acid, which cannot be synthesized by this bacterium, was incorporated as a cis unsaturated fatty acid marker in the membrane lipids of growing cells. The conversion of this fatty acid into the corresponding trans isomer was demonstrated by gas chromatographic-mass spectrometric analysis and use of 14C-labeled oleic acid. Separation and isolation of the cellular membranes showed that the fatty acid isomerase is located in the cytoplasmic membrane of P. putida P8.

Carbohydrate Sequence↗

PubMed2004

Solvent extraction and extraction-voltammetric determination of phenols using room temperature ionic liquid.

The phenolic compounds phenol, 4-nitrophenol, 2,4-dinitrophenol, 2,6-dinitrophenol, 1-naphthol, 2-naphthol, and 4-chlorophenol are extracted nearly quantitatively from aqueous solution into the room temperature ionic liquid 1-butyl-3-methylimidazolium hexafluorophosphate (BMImPF6) in molecular form at pH < p Ka. Picric acid is extracted efficiently in anionic form. Recovery of pyrocatechol and resorcinol is much lower. The effect of pH, phenol concentration, and volume ratio of aqueous and organic phases were studied. Ionic liquid BMImPF6 is shown to be suitable for extraction-voltammetric determination of phenols without back-extraction or addition of support electrolyte. The electrochemical window of BMImPF6 at various electrodes was determined, and voltammetric oxidation of phenols and reduction of nitrophenols in BMImPF6 was studied.

Journal Article↗

PubMed2005

Improving the accuracy of carbon-to-hydrogen ratio determination for P, N, S, O, Cl, and Br-containing organic compounds using atomic emission detection.

The objective of this work was to investigate the dependence of atomic emission detector C and H response on microwave-induced plasma conditions and to improve the accuracy of carbon-to-hydrogen ratio determination for trialkylphosphates, herbicides, chlorophenols, and sulfur-containing organic compounds. Compounds which differed structurally from the analytes were used as reference compounds. It was found that when the oxygen concentration in the helium was the maximum for the instrument (9%) relative errors in carbon-to-hydrogen ratio determination were 3-8%, irrespective of analyte and reference compound structure, whereas when working in the mode of operation recommended by the manufacturer of the instrument (1.5% oxygen in helium) the respective errors were 10-20% or higher. This improvement in the accuracy of carbon-to-hydrogen ratio determination was accompanied by a factor of ten decrease in sensitivity.

Journal Article↗