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PubMed2004

In vitro and in vivo analysis of the thyroid disrupting activities of phenolic and phenol compounds in Xenopus laevis.

We investigated the effects of phenolic and phenol compounds on 3,3',5-L-125I-triiodothyronine (125I-T3) binding to purified Xenopus laevis transthyretin (xTTR) and to the ligand-binding domain of X. laevis thyroid hormone receptor beta (xTR LBD), on T3-induced metamorphosis in X. laevis tadpoles and on the induction of T3-dependent reporter gene in a X. laevis cell line. Of the halogenated phenolic and phenol compounds tested, 3,3',5-trichlorobisphenol A and 2,4,6-triiodophenol, respectively, were the most potent competitors of 125I-T3 binding to both xTTR and xTR LBD. Most of the halogenated compounds had stronger interactions with xTTR than with xTR LBD. Generally, chlorinated derivatives with a greater degree of chlorination were more efficient competitors of T3 binding to xTTR and xTR LBD. Structures with a halogen in either ortho position or in both ortho positions, with respect to the hydroxy group, were more efficient competitors. 3,3',5-Trichlorobisphenol A and 2,4,6-triiodophenol acted as T3 antagonists in the X. laevis tadpole metamorphosis assay. Interestingly, o-t-butylphenol and 2-isopropylphenol, for which xTTR and xTR LBD had weak or no significant affinity, showed T3 antagonist activity in the metamorphosis assay. T3 antagonist activities of all these chemicals except for o-t-butylphenol were verified by T3-dependent reporter gene assay. Our results suggest that some phenolic and phenol compounds target the process of T3 binding to xTTR and xTR and/or an unknown process, and that they interfere with the intracellular T3 signaling pathway.

Animals↗
PubMed1987

Phenol hydroxylase from yeast. A model for phenol binding and an improved purification procedure.

The binding of phenol to phenol hydroxylase was studied by equilibrium dialysis, spectrophotometric titration and by steady-state kinetics. A binding model with two identical, negatively cooperative, effector/substrate-binding sites per enzyme dimer is proposed. The spectral perturbation caused by phenol and the kinetics of the overall reaction were analysed with relation to the enzyme-phenol complexes of the binding model. The main part of the spectral perturbation as well as of the increase in NADPH oxidation rate was achieved by one molecule of phenol bound per enzyme dimer. The properties of different enzyme-phenol complexes, in terms of spectral changes, hydroxylase activity, oxidase activity and substrate inhibition are discussed. A new purification procedure is described.

Chromatography, Affinity↗
PubMed2001

Group-specific monitoring of phenol hydroxylase genes for a functional assessment of phenol-stimulated trichloroethylene bioremediation.

The sequences of the largest subunit of bacterial multicomponent phenol hydroxylases (LmPHs) were compared. It was found that LmPHs formed three phylogenetic groups, I, II, and III, corresponding to three previously reported kinetic groups, low-K(s) (the half-saturation constant in Haldane's equation for trichloroethylene [TCE]), moderate-K(s), and high-K(s) groups. Consensus sequences and specific amino acid residues for each group of LmPH were found, which facilitated the design of universal and group-specific PCR primers. PCR-mediated approaches using these primers were applied to analyze phenol/TCE-degrading populations in TCE-contaminated aquifer soil. It was found that the aquifer soil harbored diverse genotypes of LmPH, and the group-specific primers successfully amplified LmPH fragments affiliated with each of the three groups. Analyses of phenol-degrading bacteria isolated from the aquifer soil confirmed the correlation between genotype and phenotype. Competitive PCR assays were used to quantify LmPHs belonging to each group during the enrichment of phenol/TCE-degrading bacteria from the aquifer soil. We found that an enrichment culture established by batch phenol feeding expressed low TCE-degrading activity at a TCE concentration relevant to the contaminated aquifer (e.g., 0.5 mg liter(-1)); group II and III LmPHs were predominant in this batch enrichment. In contrast, group I LmPHs overgrew an enrichment culture when phenol was fed continuously. This enrichment expressed unexpectedly high TCE-degrading activity that was comparable to the activity expressed by a pure culture of Methylosinus trichosporium OB3b. These results demonstrate the utility of the group-specific monitoring of LmPH genes in phenol-stimulated TCE bioremediation. It is also suggested that phenol biostimulation could become a powerful TCE bioremediation strategy when bacteria possessing group I LmPHs are selectively stimulated.

Betaproteobacteria↗
PubMed2004

Correspondence between community structure and function during succession in phenol- and phenol-plus-trichloroethene-fed sequencing batch reactors.

The effects of more than 2 years of trichloroethene (TCE) application on community succession and function were studied in two aerobic sequencing batch reactors. One reactor was fed phenol, and the second reactor was fed both phenol and TCE in sequence twice per day. After initiation of TCE loading in the second reactor, the TCE transformation rates initially decreased, but they stabilized with an average second-order rate coefficient of 0.044 liter mg(-1) day(-1) for 2 years. In contrast, the phenol-fed reactor showed higher and unstable TCE transformation rates, with an average rate coefficient of 0.093 liter mg(-1) day(-1). Community analysis by terminal restriction fragment length polymorphism (T-RFLP) analysis of the 16S rRNA genes showed that the phenol-plus-TCE-fed reactor had marked changes in community structure during the first 100 days and remained relatively stable afterwards, corresponding to the period of stable function. In contrast, the community structure of the phenol-fed reactor changed periodically, and the changes coincided with the periodicity observed in the TCE transformation rates. Correspondence analysis of each reactor community showed that different community structures corresponded with function (TCE degradation rate). Furthermore, the phenol hydroxylase genotypes, as determined by restriction fragment length polymorphism analysis, corresponded to community structure patterns identified by T-RFLP analysis and to periods when the TCE transformation rates were high. Long-term TCE stress appeared to select for a different and stable community structure, with lower but stable TCE degradation rates. In contrast, the community under no stress exhibited a dynamic structure and dynamic function.

Bacteria↗
PubMed1985

Biological activity of phenolic compounds. Hepatic cytochrome P-450, cytochrome b5, and NADPH cytochrome c reductase in chicks and rats fed phenolic monomers, polymers, and glycosides.

Eight experiments were conducted to determine effects of a phenolic polymer (Kraft wood lignin, Indulin), phenolic glycosides (cane molasses and wood molasses), and phenolic monomers (vanillin, vanillic acid, ferulic acid, and p-coumaric acid) on liver cytochromes P-450, cytochrome b5, and NADPH cytochrome c reductase in chicks and rats. Chicks fed 6.0% lignin had a higher (P less than 0.01) cytochromes P-450 content than did chicks fed 0% fiber, 6.0% wood cellulose (Solka Floc), or 6.0% arenaceous flour. NADPH cytochrome c reductase activity was not affected by treatment. Chicks fed 12.0% wood molasses had a higher (P less than 0.06) cytochromes P-450 level than did chicks fed 0% fiber or 6.0% wood molasses. Cane molasses incorporated at both 6.0 and 12.0% of the diet induced (P less than 0.05) cytochromes P-450 content over those of control-fed birds. Chicks fed 6.0% lignin, with or without antibiotic (bacitracin:neomycin sulfate, 2:1), had a higher (P less than 0.01) cytochromes P-450 level than did chicks fed control diets, with or without antibiotic. Additionally, chicks fed 6.0% lignin had lower (P less than 0.01) intestinal diaminopimelic acid (DAP) levels than did chicks fed 0% fiber. Rats fed 0% fiber, 6.0% wood cellulose, 6.0% arenaceous flour, or 6.0% lignin exhibited no difference in cytochrome level or activity among treatments. Chicks fed 0.5% vanillin, 0.5% vanillic acid, 0.5% ferulic acid, or 0.5% p-coumaric acid had comparable cytochromes level and activity compared with chicks fed no phenolics. Chicks fed 0.5% p-coumaric acid had lower (P less than 0.05) rates of gain than did chicks fed control or other phenolic-containing diets. Rats fed these phenolics had similar cytochromes P-450 content among treatments.

Age Factors↗
PubMed2001

[The detection of phenol degrading strain in environment with specific primer of phenol hydroxylase gene].

A 684 bp oligonucleotide fragment was produced by PCR amplification from phenol-degrading strain Acinetobacter calcoaceticus PHEA-2 with the specific primers of gene encoding phenol hydroxylase. The nucleotide sequence of this fragment and its deduced amino acid sequence share 84% and 98% homology with the phenol hydroxylase gene and its deduced amino acid sequences of phenol-degrading strain Acinetobacter calcoaceticus NCIB8250. Sets of different aromatic compounds degrading strains were used to test this specific prime. The 684 bp-fragments were amplified only from phenol-degrading strains by PCR. When using this pair of primers to detect the bacterial isolates from wastewater discharged from coking plant, all the tested strains, which possess 684 bp characteristic fragment, showed the ability to degrade phenol in this study.

Acinetobacter calcoaceticus↗
PubMed2005

[Culture and biodegradation performance for phenol-degrading bacterium in high phenol concentration].

The activated sludge was acclimated by the inorganic salt medium containing phenol as the sole carbon source. The phenol-degrading bacterium obtained now can degrade completely phenol at initial concentration of 1 700mg/L at 30 degrees C for 15h, and COD can be degraded by 96.9%. Some factors effecting degradation of phenol and COD were studied, which include initial phenol concentration, quantity of bacterium, temperature and pH. Four strains of bacterium were isolated from the mixed phenol-degrading bacterium. It is shown that the degradation effect of mixed bacterium is superior to that of sole strain.

Bacteria↗
PubMedDate not supplied

Rapid, dose-dependent elimination of phenol across the gills, and slow elimination of phenyl sulfate in the urine of phenol-dosed lobsters, Homarus americanus.

Although lobsters are known to metabolize lipophilic organic compounds by monooxygenation, little is known of the fate of the hydroxylated metabolites. Single doses of [14C]phenol, 0.019 to 2.8 mg/kg, were administered intrapericardially to groups of lobsters. Hemolymph was sampled serially from appendage joints and analyzed for radioactivity and chemical composition. Separate groups of lobsters were dissected at 0.5, 4, and 24 hr after the 0.1-mg/kg dose to collect urine and tissue samples. Tank water was collected at 0.5 hr and analyzed. Phenol concentrations decreased rapidly in hemolymph (alpha t1/2 = 8.7 min, beta t1/2 = 14.0 min) and part of the dose was excreted through gills into tank water as parent phenol in the first 30 min. The percentage of each dose excreted through the gills increased with increasing dose up to greater than 90% at greater than 2 mg/kg. The phenol that was not excreted through gills was rapidly conjugated with sulfate in the antennal glands and possibly other sites. In both male and female lobsters, phenyl sulfate was eliminated from hemolymph much more slowly than parent phenol. The terminal elimination half-life of phenyl sulfate was slower in females (t1/2 = 11.9 hr) than in males (t1/2 = 6.3 hr). The [14C] present in urine collected 24 hr after the dose consisted primarily of phenyl sulfate (greater than 97%) with traces of phenyl beta-D-glucoside (0.1-3%). Thus, in the lobster, metabolism of phenol to polar conjugates did not enhance elimination from the animal.

Animals↗
PubMed2005

Relationships between phenolic acid concentrations, transpiration, water utilization, leaf area expansion, and uptake of phenolic acids: nutrient culture studies.

Phenolic acid treatments of cucumber seedlings (Cucumis sativus cv "Early Green Cluster") inhibited transpiration, water utilization, leaf area, and absolute and relative rates of leaf expansion. The cinnamic acids, ferulic and p-coumaric acids, were two to five times more inhibitory than the benzoic acids, p-hydroxybenzoic acid and vanillic acid. When phenolic acid concentrations were maintained at inhibitory concentrations through multiple successive treatments, percent inhibition of water utilization remained relatively constant for a given concentration and phenolic acid, percent inhibition of leaf area initially increased and then leveled off to a constant percent, and percent inhibition of transpiration and rates of leaf area expansion declined over time. Subsequently, p-coumaric acid was chosen as the model compound for further study. When p-coumaric acid was inhibitory, percent inhibition of transpiration, water utilization, and rates of leaf area expansion of actively growing leaves rapidly declined (i.e., was lost) as p-coumaric acid concentrations surrounding roots decreased. Absolute and relative rates of leaf expansion, for example, declined approximately 12 and 14%, respectively, for every 0.1 mM decline in p-coumaric acid concentration. Uptake of p-coumaric acid by cucumber seedling roots was continuous over the 24- or 36-hr periods monitored, but was not consistently related to the initial p-coumaric acid treatment concentrations. However, declining p-coumaric acid concentrations monitored at 6- or 12-hr intervals over the 24- or 36-hr periods continued to be highly correlated to the initial p-coumaric acid treatment concentrations. A 25% depletion by 1 3-d-old cucumber seedlings took 8.5, 12, 19.5, 25, and 29.5 hr for 0.125-, 0.25-, 0.5-, 0.75-, and 1-mM treatments, respectively. Uptake during periods when phenolic acid concentrations and root uptake (depletion from solution) were related appeared to represent periods dominated by apoplastic movement into the intercellular spaces of roots. Uptake during periods without this relationship likely represented periods dominated by symplastic movement. The ability of cucumber seedlings to modify active phenolic acid concentrations surrounding their roots suggests that cucumber seedling can directly influence the magnitude of primary and secondary effects of phenolic acids through feedback regulation.

Cucumis sativus↗
PubMed2006

Characteristics of phenol and chlorinated phenols sorption onto surfactant-modified bentonite.

Surfactant-modified bentonite was synthesized by replacing adsorbed Na+ with long-chain alkyl quaternary ammonium cation, hexadecyltrimethylammonium bromide (HDTMAB). The sorption isotherms of phenol, p-chlorophenol, and 2,4-dichlorophenol were modeled according to the Langmuir and Freundlich equations. The Langmuir isotherm was found to describe the equilibrium adsorption data well. The mechanisms and characteristics of sorption of these ionizable organic contaminants onto surfactant-modified bentonite from water were investigated systematically and described quantitatively. The sorption properties are affected by the treatment conditions, such as amount of organobentonite, and the properties of organic compounds. Results indicated that adsorption of phenols from water was in proportion to their hydrophobicities, which increased with chlorine addition (phenol<p-chlorophenol<2,4-dichlorophenol). Sorption isotherms of these phenols were typically nonlinear. Both adsorption and partition contribute to the sorption of investigated phenols to organobentonite. The separate contributions of adsorption and partition to the total sorption of these compounds to organobentonite is analyzed mathematically. Results indicate that the partition effect is weak and linear with contaminant concentration, whereas the adsorption effect is more powerful and nonlinear with contaminant concentration. The sorption of phenols onto organobentonite was dominated by adsorption at low concentrations and partition started to dominate at high concentrations, making the organobentonites powerful sorbents for organic contaminants over a wide range of concentrations.

Journal Article↗
PubMed2004

Picosecond IR-UV pump-probe spectroscopic study of the dynamics of the vibrational relaxation of jet-cooled phenol. I. Intramolecular vibrational energy redistribution of the OH and CH stretching vibrations of bare phenol.

The intramolecular vibrational energy redistribution (IVR) of the OH stretching vibration of jet-cooled phenol-h6 (C6H8OH) and phenol-d8 (C6D8OH) in the electronic ground state has been investigated by picosecond time-resolved IR-UV pump-probe spectroscopy. The OH stretching vibration of phenol was excited with a picosecond IR laser pulse, and the subsequent temporal evolutions of the initially excited level and the redistributed ones due to the IVR were observed by multiphoton ionization detection with a picosecond UV pulse. The IVR lifetime for the OH stretch vibration of phenol-h6 was determined to be 14 ps, while that of the OH stretch for phenol-d8 was found to be 80 ps. This remarkable change of the IVR rate constant upon the dueteration of the CH groups strongly suggests that the "doorway states" for the IVR from the OH level would be the vibrational states involving the CH stretching modes. We also investigated the IVR rate of the CH stretching vibration for phenol-h6. It was found that the IVR lifetime of the CH stretch is less than 5 ps. The fast IVR is described by the strong anharmonic resonance of the CH stretch with many other combinations or overtone bands.

Journal Article↗
PubMed1987

Effect of adaptation to phenol on biodegradation of monosubstituted phenols by aquatic microbial communities.

The adaptation of a mixed aquatic microbial community to phenol was examined in microcosms receiving phenol as a sole carbon source. Extended exposure (adaptation) to phenol resulted in adaptation of the microbial community to the structurally related aromatic compounds m-cresol, m-aminophenol, and p-chlorophenol. The increased biodegradation potential of the phenol-adapted microbial community was accompanied by a concurrent increase in the number of microorganisms able to degrade the three test compounds. Thus, adaptation to the three test chemicals was likely a growth-related result of extended exposure to phenol. The results indicate that adaptation to a single chemical may increase the assimilative capacity of an aquatic environment for other related chemicals even in the absence of adaptation-inducing levels of those materials.

Adaptation, Physiological↗
PubMed1987

Serum and urine levels of phenol following phenol blocks.

In 20 patients with chronic peripheral vascular disease measurement was made of serum and urine phenol concentrations after lumbar or thoracic sympathetic block with 4-10 ml of seven per cent aqueous phenol. Peak concentration times (tmax), peak concentrations (Cmax), lag times (Tlag), apparent elimination half-lives (t1/2el), and areas under the serum concentration curves (AUC) were determined. The values of tmax, Cmax, Tlag, t1/2el, and AUC were 18.8 +/- 2.5 min, 3.01 +/- 0.28 microgram X ml-1, 5.3 +/- 1.6 min, 30.3 +/- 2.8 min, and 365 +/- 41 micrograms X ml-1 X min-1, respectively, for unconjugated phenol. Values for conjugated phenol were 54.9 +/- 4.5 min, 4.15 +/- 0.25 microgram X ml-1, 9.9 +/- 5.9 min, 64.0 +/- 7.3 min, and 838 +/- 95 micrograms X ml-1 X min-1, respectively. The cumulative urinary excretion in the conjugated form within 8 h ranged from 31 to 63 per cent of the dose administered. The results indicate that phenol has a very short half-life and is excreted quickly into the urine, conjugated with sulfate.

Adult↗
PubMed2006

Genotype and environmental variation in phenolic content, phenolic acid composition, and antioxidant activity of hard spring wheat.

The health-promoting effects of whole-grain wheat likely derive from phenolic compounds and other antioxidants that also make wheat a potential source of functional food ingredients. The objective of this study was to determine the effects of genotype and growing environment on the phenolic contents and antioxidant activities of alcohol-soluble extracts from commercial wheat cultivars. Total phenolic contents (TPCs), antioxidant activities (AOAs), and concentrations of six phenolic acids were measured in six red- and white-grained hard spring wheat genotypes grown at four diverse locations in Western Canada during the 2003 crop year. There were significant differences among genotypes and environments for TPC, AOA, and concentrations of all the phenolic acids measured. The predominant indicators of antioxidant potential, i.e., TPC, AOA, and ferulic acid (FA) concentration were highly intercorrelated (r > 0.72). For these indices, the Canada Western (CW) Red Spring wheat cultivars Neepawa and AC Elsa had the highest levels, whereas an analogous CW hard white spring wheat cultivar, AC Snowbird, had the lowest levels. Grain color did not appear to be a factor in the expression of antioxidant-related parameters. For both TPC and AOA, as well as for vanillic acid, syringic acid, and ferulic acid, environmental effects were considerably larger than genotype effects. Neither growing temperature nor rainfall from anthesis to maturity appeared to be related to the environmental variation that was observed. Genotype x environment interaction was small for all parameters compared with genotype and location effects and was significant only for TPC. Genotype variation for antioxidant properties indicates that it would be possible to select for these quantitative traits in a breeding program. However, the significant environmental variation observed would delay and/or complicate this process.

Antioxidants↗
PubMed1998

Solubility enhancement of phenol and phenol derivatives in perfluorooctyl bromide.

Perfluorinated solvents are gaining popularity as pulmonary ventilation fluids, but they suffer from poor solvent quality in concurrent drug delivery applications. The present study examines the use of a hydrophobic solubilizing agent capable of interacting with model drug solutes by hydrogen bonding with the purpose of enhancing solubility in perfluorooctyl bromide (PFOB). A series of solubilizing agents containing a ketone carbonyl to act as a hydrogen bond acceptor and a perfluoroalkyl chain to maintain the solubility of the putative complex in PFOB are investigated. The solubility of phenol in PFOB is enhanced to the greatest extent by 1-(4-perfluorobutyl phenyl)-1-hexanone (III) where the ketone carbonyl is protected from the electron withdrawing effects of the perfluorobutyl chain by a phenyl ring. Experiments with solubilizers lacking the ketone group suggest that pi-pi bond interactions of III with phenol do not significantly enhance solubility. For a series of phenol derivatives, a rank-order correlation exists between the magnitude of solubility enhancement by III, as reflected by the calculated association constants, and the Hammett sigma parameter of the phenols. Because the O-methyl-substituted phenols do not have the ability to hydrogen bond, their solubility is not enhanced by the presence of III. The results of the present study indicate that solubility of model drug hydrogen bond donating compounds can be enhanced in PFOB by the presence of fluorocarbon-soluble hydrogen bond acceptors.

Chromatography, High Pressure Liquid↗
PubMed1997

Supplementation with wine phenolic compounds increases the antioxidant capacity of plasma and vitamin E of low-density lipoprotein without changing the lipoprotein Cu(2+)-oxidizability: possible explanation by phenolic location.

OBJECTIVES: To evaluate the effect of the red wine phenolic compound (RWPC) dietary supplementation without alcohol interference on: (1) some of the biochemical characteristics of LDL, (2) the oxidative susceptibility of LDL and (3) the antioxidant capacity of total plasma (Pl-AOC). In order to account for discrepancies between the three series of data, the in vitro stability of the association of phenolic compounds and LDL was tested. DESIGN: An intervention study with 20 volunteers. Each served as his own control. Cu(2+)-oxidizability of LDL and Pl-AOC were tested on blood samples before and after dietary supplementation. Cu(2+)-oxidizability of LDL was also tested by co-incubation in the presence of RWPC or phenolic acids with or without extensive dialysis. SETTING: The Laboratory of Lipid Biochemistry and Biology, School of Medicine, and the Laboratory of Metabolic Diseases, Lapeyronie Hospital, University of Montpellier, France. SUBJECTS: Healthy males, nonsmokers and moderate drinkers, submitted to a dietary regimen deprived of vitamin E and C for a period of 10 d before supplementation. They also abstained from alcohol, wine, fruit juices, coffee, tea and cola beverages during this period. INTERVENTION: Six 0.33 g capsules/d (namely two capsules at each meal) of a preparation of red wine phenolic compounds in a dry powder form were given to the volunteers over a period of two weeks. Blood samples were drawn in fasting conditions at day 0 and day 14 of the supplementation period. RESULTS: Supplementation led to: (1) in LDL, a significant increase in vitamin E content (n = 20, P = 0.01) or vitamin E/total fatty acid bis-allylic carbon number ratio (n = 20, P = 0.006) without modification in the other biochemical characteristics or Cu(2+)-oxidizability; (2) in plasma, a significant increase in the antioxidant capacity (n = 11, P = 0.01). In vitro studies showed that RWPC or sinapic, caffeic or ferulic acids incubated in the presence of LDL increased the protection of the lipoparticle against oxidation (caffeic > sinapic > ferulic). This effect, however, was totally lost after extensive dialysis. CONCLUSIONS: The enhancing effect of the RWPC supplementation on Pl-AOC may be due to a phenolic-compound action both in the aqueous phase of plasma and at the surface of lipoprotein particles. Surface location possibly explains the enhancing-sparing effect of supplementation on LDL vitamin E and the absence of effect on dialysed-LDL oxidizability.

Adult↗
PubMed2006

Competition between cation-pi interactions and intermolecular hydrogen bonds in alkali metal ion-phenol clusters. II. Phenol trimer.

The competition between ion-molecule and molecule-molecule interactions was investigated in M+(phenol)3 cluster ions for M=Li, Na, K, and Cs. Infrared predissociation spectroscopy in the O-H stretch region was used to characterize the structure of the cluster ions. By adjusting the experimental conditions, it was possible to generate species where argon was additionally bound in order to investigate cold cluster ions. From a comparison of the M+(phenol)3 spectra with the M+(phenol)3Ar spectra, it is clear that the relative populations of hydrogen-bonded configurations are significantly higher in the colder (argon-bearing) species. For the cold species, the IR spectra were compared with minimum energy ab initio calculations to elucidate the hydrogen-bonded structures. The experimental spectra are most consistent with a cyclic hydrogen-bonded configuration for Cs+(phenol)3 in which the ion binds to the phenol molecules via cation-pi interactions, and noncyclic configurations for Li+, Na+, and K+.

Argon↗