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PubMedDate not supplied

Fluorescence and bioluminescence analysis of sequential UV-biological degradation of p-cresol in water.

The photolysis and Penicillium tardum H-2 degradation of p-cresol in water containing humic acids was investigated by fluorescence and bioluminescence methods. Humic acids extracted from peat (the Vasuygan bog, Tomsk region of Russia) induce the phototransformation of p-cresol. The influence of humic acids on the phototransformation of p-cresol under different irradiation conditions was investigated. Comparison of the data on the KrCl* (lambda = 222 nm) and XeCl* (lambda = 308 nm) excilamps light showed that the most effective p-cresol degradation was observed with mercury lamp irradiation in the presence of humic acids.

Biodegradation, Environmental↗
PubMedDate not supplied

Rapid determination of O- and P-cresol isomers in urine from workers exposed to toluene by high-performance liquid chromatography using a graphitized carbon column.

A simple and rapid procedure is described that permits the simultaneous determination of o- and p-cresol in urine of workers of other individuals exposed to toluene. The urine samples are enzymatically hydrolysed and analysed by high-performance liquid-chromatography with a detection limit of 0.2 mg/L, one fifth of the biological threshold limit value for o-cresol (1 mg/g), a specific marker of toluene exposure. A graphitized carbon column Hybercarb-S, that exhibits an excellent selectivity for aromatic positional isomers, was used with 1% phosphoric acid-acetonitrile (70:30, v/v) as mobile phase and a detection wavelength of 271 nm. The overall accuracy for o-cresol determination was 4.5% at 5 mg/L and 8% at 0.5 mg/L. The cresol isomers were sufficiently resolved from endogenous materials to avoid the need for any extraction step, and the method appears suitable for monitoring workers accurately under the permissible level of exposure for occupational medicine purpose.

Chromatography, High Pressure Liquid↗
PubMedDate not supplied

Separation of cresols using coelectroosmotic capillary electrophoresis.

A new method of capillary electrophoresis was established to separate the three cresol isomers. Cresols are of importance due to their use as insecticides, precursors of various dye intermediates, resins, fire-resistant fluids and other purposes. Reversion of the electroosmotic flow was carried out by a polycationic ammonium compound. The separations were carried out at high pH values (pH 12) to obtain complete dissociation of the cresols and short times of analysis (less than 5 min) through fast migration of the cresol towards the anode. Various aliphatic alcohols were added to improve peak shape and resolution.

1-Propanol↗
PubMed1995

Cometabolic degradation of o-cresol and 2,6-dimethylphenol by Penicillium frequentans Bi 7/2.

o-Cresol induced glucose-grown resting mycelia of Penicillium frequentans Bi 7/2 (ATCC-number: 96048) immediately oxidized o-cresol and other phenols. After precultivation on glucose and phenol degradation started after a lag-phase of 24 hours. Metabolites of o-cresol metabolism were methylhydroquinone, methyl-p-benzoquinone, 2-methyl-5-hydroxyhydroquinone and 2-methyl-5-hydroxy-p-benzoquinone. The initial reaction is probably catalyzed by a NADPH dependent hydroxylase which is specific for o-cresol. The metabolism of 2,6-dimethylphenol (2,6-xylenol) occurred via 2,6-dimethylhydroquinone, 2,6-dimethyl-p-benzoquinone, 2,6-dimethyl-3-hydroxyhydroquinone, 2,6-dimethyl-3-hydroxy-p-benzoquinone and 3-methyl-2-hydroxybenzoic acid.

Chromatography, High Pressure Liquid↗
PubMed2000

Catalytic oxidation of p-cresol by ascorbate peroxidase.

Transient and steady state kinetics, together with a range of chromatographic and spectroscopic techniques, have been used to establish the mechanism and the products of the H(2)O(2)-dependent oxidation of p-cresol by ascorbate peroxidase (APX). HPLC, GC-MS, and NMR analyses are consistent with the formation of 2, 2'-dihydroxy-5,5'-dimethylbiphenyl (II) and 4alpha,9beta-dihydro-8, 9beta-dimethyl-3(4H)-dibenzofuranone (Pummerer's ketone, III) as the major products of the reaction. In the presence of cumene hydroperoxide, two additional products were observed which, from GC and MS analyses, were shown to be 1,1-dimethylbenzylalcohol (IV) and bis-(1-methyl-1-phenyl-ethyl)-peroxide (V). The product ratio II:III was dependent on enzyme concentration: at low concentrations Pummerer's ketone (III) predominates and at high concentrations formation of the biphenyl compound (II) is favored. Steady-state data showed a sigmoidal dependence on [p-cresol] that was consistent with the presence of 2.01 +/- 0.15 binding sites for the substrate (25.0 degrees C, sodium phosphate, pH 7.0, mu = 2.2 mM) and independent of ionic strength in the range 2.2-500 mM. Single turnover kinetic experiments (pH 7.0, 5.0 degrees C, mu = 0.10 M) yielded second-order rate constants for Compound I reduction by p-cresol, k(2), of 5.42 +/- 0.10 x 10(5) M(-1) s(-1), respectively. Rate-limiting reduction of Compound II by p-cresol, k(3), showed saturation kinetics, giving values for K(d) = 1.54 +/- 0.12 x 10(-3) M and k(3) = 18.5 +/- 0.7 s(-1). The results are discussed in the more general context of APX-catalyzed aromatic oxidations.

Ascorbate Peroxidases↗
PubMed1992

Urinary excretion of o-cresol and hippuric acid after toluene exposure in rotogravure printing.

In 62 male rotogravure printers, the time-weighted average (TWA) toluene exposure during one workweek ranged from 8 to 496 mg/m3 (median 96). Post-shift urinary excretion of hippuric acid showed a poor correlation with the air toluene concentration. Level of o-cresol excretion ranged from 0.08 to 2.37 mmol/mol creatinine and was associated with the exposure (rS = 0.57, P less than 0.0001), although the variation was considerable. However, this metabolite was significantly influenced by smoking habits, both in the workers (0.34 vs 0.10 mmol/mol creatinine after adjustment to zero exposure for the smokers and non-smokers, respectively; P = 0.03) and in 21 unexposed controls (0.18 vs 0.06 mmol/mol creatinine; P = 0.002). The excretion of these metabolites was followed during vacation, when the workers were unexposed. The shared one-compartment half-time was 44 h (+/- SE 30, 82). After 2-4 weeks of vacation, the concentration of o-cresol was significantly higher for the smokers than the non-smokers (0.14 vs 0.06 mmol/mol creatinine; P = 0.02). No smoking-associated difference was found for the urinary hippuric acid concentration. However, there was an association between alcohol consumption and hippuric acid excretion (P = 0.03); no such difference was shown for o-cresol. These results demonstrate that hippuric acid excretion is unsuitable for biological monitoring of toluene exposure when the exposure level is below 200 mg/m3. Also, in spite of the favourable excretion kinetics, the impact of smoking and the large interindividual variation warrant the same conclusion for o-cresol as a means of monitoring low level exposure in an individual worker.

Adult↗
PubMed2003

Unbiased spectrophotometric method for estimating phenol or o-cresol in unknown water samples.

The generalised H-point standard addition method (GHPSAM) was applied to quantify phenol and o-cresol in waters and compared with other analytical approaches. The method is based on spectroscopic and kinetic measurement of the formation of derivatives with p-aminophenol and KIO(4) in presence of NaOH. First, pseudo-first order kinetic behaviour of the reaction products was demonstrated. The unbiased formation rate constants of phenol and o-cresol derivatives were calculated. The analytical figures of merit were determined using the GHPSAM as calibration method. Detection limits achieved were 0.2 microg L(-1) of phenol and 0.2 microg L(-1) of o-cresol using a preconcentration factor of 10. Styrene-divinyl benzene cartridges were used in the preconcentration step. Repeatability values were 3.7% for phenol and 2.0% for o-cresol; reproducibility values were 6.9% and 3.5%, respectively. Accurate and precise results were obtained when the method was applied to real samples of natural water.

Cresols↗
PubMed2006

Human urine certified reference material CZ 6010: creatinine and toluene metabolites (hippuric acid and o-cresol) and a benzene metabolite (phenol).

A reference material for the biological monitoring of occupational exposure to toluene, benzene and phenol was prepared. O-cresol and hippuric acid (metabolites of toluene) are used for the biological monitoring of occupational exposure to toluene. Phenol, a metabolite of benzene, is used for the biological monitoring of exposure to benzene, but phenol can of course also be used as an indicator of exposure to phenol as well. The reference material (RM) used for the determination of these metabolites was prepared by freeze-drying pooled urine samples obtained from healthy persons occupationally exposed to toluene and those taking part in an inhalation experiment. Tests for homogeneity and stability were performed by determining urine concentrations of o-cresol, hippuric acid, creatinine and phenol. To investigate the stability of the RM, the urinary concentrations of o-cresol and phenol were monitored for eighteen months using GC and HPLC, while those of hippuric acid and creatinine were followed for five and six years, respectively, using HPLC. Analysis of variance showed that the concentrations did not change. The certified concentration values (and their uncertainties) of the substances in this reference material (phenol concentration c=6.46+/-0.58 mg l(-1); o-cresol concentration c=1.17+/-0.15 mg l(-1); hippuric acid concentration c=1328+/-30 mg l(-1); creatinine concentration c=0.82+/-0.10 g l(-1)) were evaluated via the interactive statistical programme IPECA.

Benzene↗
PubMed2006

Biodegradation of p-cresol by Bacillus sp. strain PHN 1.

A bacterium capable of utilizing p-cresol as sole source of carbon and energy was isolated from soil and identified as a Bacillus species. The organism also utilized phenol, o-cresol, m-cresol, 4-hydroxybenzoic acid, and gentisic acid as growth substrates. The organism degraded p-cresol to 4-hydroxybenzoic acid, which was further metabolized by a gentisate pathway, as evidenced by isolation and identification of metabolites and enzyme activities in the cell-free extract. Such a bacterial strain can be used for bioremediation of environments contaminated with phenolic compounds.

Bacillus↗
PubMed1992

Potentiation by m-cresol on transepithelial sodium transport across frog skin induced by insulin.

1. In this study we found that insulin mixed with m-cresol, normally used as pharmaceutical preparation, shows an earlier and larger stimulating effect on transepithelial sodium transport than insulin alone. 2. The action displayed by the m-cresol seems to be specific for insulin because m-cresol mixed with ADH, a hormone known to stimulate sodium transport, failed to show the potentiation seen for insulin. 3. It is proposed that m-cresol could facilitate the interaction with its receptor by modifying the insulin molecule. 4. This finding could be of biological and pharmacological importance.

Animals↗
PubMed2002

Interactive effects of the electron acceptor sulphate and o-cresol on the methanogenic degradation of hexanoate.

A three-stage continuous culture system was used to segregate the component microbial groups of a methanogenic hexanoate-degrading association enriched from anaerobic refuse. The inhibitory effects of o-cresol concentrations (2-20 mM) on the fermentative, acetogenic, sulphate-reducing and methanogenic bacteria were then assessed in the presence of either 1.4 or 3.5 mM sulphate in the influent medium. The sulphate-reducing bacteria (SRB) in the 1.4 mM sulphate-supplemented systems were the most sensitive to o-cresol, with 29.3 and 56.6% inhibition on supplementation with 4 and 6 mM o-cresol, respectively. With 3.5mM supplementation, inhibition was 4.5 and 19.4%, respectively. Methanogenesis was not inhibited by concentrations < 10 mM o-cresol, and complete inhibition was recorded only at concentrations > or = 10 mM. Both fermentation and acetogenesis were affected by inhibition of the electron sinks. The increase in influent sulphate concentration promoted electron flow to sulphidogenesis, as predicted on thermodynamic criteria, but did not affect the relative sensitivity of the different physiological groups.

Bacteria, Anaerobic↗
PubMed1998

Interactions of phenol and m-cresol in the insulin hexamer, and their effect on the association properties of B28 pro --> Asp insulin analogues.

Insulin's natural tendency to form dimers and hexamers is significantly reduced in a mutant insulin B28 Pro --> Asp, which has been designed as a monomeric, rapid-acting hormone for therapeutic purposes. This molecule can be induced to form zinc hexamers in the presence of small phenolic derivatives which are routinely used as antimicrobial agents in insulin preparations. Two structures of B28 Asp insulin have been determined from crystals grown in the presence of phenol and m-cresol. In these crystals, insulin exists as R6 zinc hexamers containing a number of phenol or m-cresol molecules associated with aromatic side chains at the dimer-dimer interfaces. At the monomer-monomer interfaces, the B28 Pro --> Asp mutation leads to increased conformational flexibility in the B chain C termini, resulting in the loss of important intermolecular van der Waals contacts, thus explaining the monomeric character of B28 Asp insulin. The structure of a cross-linked derivative of B28 Asp insulin, containing an Ala-Lys dipeptide linker between residues B30 Ala and A1 Gly, has also determined. This forms an R6 zinc hexamer containing several m-cresol molecules. Of particular interest in this structure are two m-cresol molecules whose binding disrupted the beta-strand in one of the dimers. This observation suggests that the cross-link introduces mechanical strain on the B chain C terminus, thereby weakening the monomer-monomer interactions.

Aspartic Acid↗
PubMed2001

Mutations to Gly2370, Gly2373 or Gly2375 in malignant hyperthermia domain 2 decrease caffeine and cresol sensitivity of the rabbit skeletal-muscle Ca2+-release channel (ryanodine receptor isoform 1).

Mutations G2370A, G2372A, G2373A, G2375A, Y3937A, S3938A, G3939A and K3940A were made in two potential ATP-binding motifs (amino acids 2370-2375 and 3937-3940) in the Ca(2+)-release channel of skeletal-muscle sarcoplasmic reticulum (ryanodine receptor or RyR1). Activation of [(3)H]ryanodine binding by Ca(2+), caffeine and ATP (adenosine 5'-[beta,gamma-methylene]triphosphate, AMP-PCP) was used as an assay for channel opening, since ryanodine binds only to open channels. Caffeine-sensitivity of channel opening was also assayed by caffeine-induced Ca(2+) release in HEK-293 cells expressing wild-type and mutant channels. Equilibrium [(3)H]ryanodine-binding properties and EC(50) values for Ca(2+) activation of high-affinity [(3)H]ryanodine binding were similar between wild-type RyR1 and mutants. In the presence of 1 mM AMP-PCP, Ca(2+)-activation curves were shifted to higher affinity and maximal binding was increased to a similar extent for wild-type RyR1 and mutants. ATP sensitivity of channel opening was also similar for wild-type and mutants. These observations apparently rule out sequences 2370-2375 and 3937-3940 as ATP-binding motifs. Caffeine or 4-chloro-m-cresol sensitivity, however, was decreased in mutants G2370A, G2373A and G2375A, whereas the other mutants retained normal sensitivity. Amino acids 2370-2375 lie within a sequence (amino acids 2163-2458) in which some eight RyR1 mutations have been associated with malignant hyperthermia and shown to be hypersensitive to caffeine and 4-chloro-m-cresol activation. By contrast, mutants G2370A, G2373A and G2375A are hyposensitive to caffeine and 4-chloro-m-cresol. Thus amino acids 2163-2458 form a regulatory domain (malignant hyperthermia regulatory domain 2) that regulates caffeine and 4-chloro-m-cresol sensitivity of RyR1.

Adenosine Triphosphate↗
PubMed1971

Gentisic acid and its 3- and 4-methyl-substituted homologoues as intermediates in the bacterial degradation of m-cresol, 3,5-xylenol and 2,5-xylenol.

1. Intact cells of a non-fluorescent Pseudomonas grown with m-cresol, 2,5-xylenol, 3,5-xylenol, 3-ethyl-5-methylphenol or 2,3,5-trimethylphenol rapidly oxidized all these phenols to completion. 3-Hydroxybenzoate and 2,5-dihydroxybenzoate (gentisate) were also readily oxidized. 2. 3-Hydroxybenzoic acid and 2,5-dihydroxybenzoic acid were isolated as products of m-cresol oxidation by cells inhibited by alphaalpha'-bipyridyl. Alkyl-substituted 3-hydroxybenzoic acids and alkyl-substituted gentisic acids were formed similarly from 2,5-xylenol, 3,5-xylenol, 3-ethyl-5-methylphenol and 2,3,5-trimethylphenol. 3. When supplemented with NADH, not NADPH, extracts of cells grown with 2,5-xylenol catalysed the oxidation of all five phenols and accumulated the corresponding gentisic acids in the presence of alphaalpha'-bipyridyl. 4. Cells of a fluorescent Pseudomonas grown with m-cresol oxidized m-cresol, 3,5-xylenol and 3-ethyl-5-methylphenol to completion and oxidized 2,5-xylenol and 2,3,5-trimethylphenol partially. The oxidation product of 2,5-xylenol was identified as 3-hydroxy-4-methylbenzoic acid. In the presence of alphaalpha'-bipyridyl, 3-hydroxy-5-methylbenzoic acid and 3-methylgentisic acid were formed from 3,5-xylenol.

Benzoates↗
PubMed2006

P-cresylsulphate, the main in vivo metabolite of p-cresol, activates leucocyte free radical production.

BACKGROUND: Chronic renal insufficiency is associated with the retention of solutes normally excreted by healthy kidneys. P-cresol, a prototype protein-bound uraemic retention solute, has been shown to exert toxic effects in vitro. Recently, however, it has been demonstrated that p-cresol in the human body is conjugated, with p-cresylsulphate as the main metabolite. METHODS: The present study evaluates the effect of p-cresylsulphate on the respiratory burst activity of leucocytes. RESULTS: P-cresylsulphate significantly increased the percentage of leucocytes displaying oxidative burst activity at baseline. Oxidative burst activity of stimulated leucocytes was however not affected. In contrast, p-cresol had no effect on the leucocytes at baseline, but inhibited leucocytes burst activity after stimulation. CONCLUSION: The present study demonstrates, for the first time, that p-cresylsulphate, the main in vivo metabolite of p-cresol, has a pro-inflammatory effect on unstimulated leucocytes. This effect could contribute to the propensity to vascular disease in the uraemic population.

Biomarkers↗
PubMed1984

Evidence for isofunctional enzymes in the degradation of phenol, m- and p-toluate, and p-cresol via catechol meta-cleavage pathways in Alcaligenes eutrophus.

A study of the degradation of phenol, p-cresol, and m- and p-toluate by Alcaligenes eutrophus 345 has provided evidence that these compounds are metabolized via separate catechol meta-cleavage pathways. Analysis of the enzymes synthesized by wild-type and mutant strains and by strains cured of the plasmid pRA1000, which encodes m- and p-toluate degradation, indicated that two or more isofunctional enzymes mediated several steps in the pathway. The formation of three catechol 2,3-oxygenases and two 2-hydroxymuconic semialdehyde hydrolases was indicated from an examination of the ratio of the specific activities of these enzymes against various substrates. Evidence for two 2-hydroxymuconic semialdehyde dehydrogenases, two 4-oxalocrotonate isomerases and decarboxylases, and three 2-ketopent-4-enoate hydratases was derived from the induction of these enzymes under different growth conditions. Each activity was detected when the wild type was grown in the presence of m-toluate, but not when grown with phenol (except for a hydratase) or p-cresol, whereas in strains cured of pRA1000, growth with phenol or p-cresol, but not with m-toluate, induced these enzymes. Hydroxylation of phenol and p-cresol appears to be mediated by the same enzyme.

Alcaligenes↗
PubMed1994

Concentrations of phenol, o-cresol, and 2,5-xylenol in the urine of workers employed in the distillation of the phenolic fraction of tar.

Phenol (87.3 mg/l), p-cresol (58.6 mg/l), o-cresol (76.9 mg/l), and 2,5-xylenol (36.7 mg/l) were detected in the urine of workers employed in the distillation of the high temperature phenolic fraction of tar (carbolic oil). The concentrations of these compounds in the urine of non-exposed male workers was 11.7 mg/l, 25.7 mg/l, 68.1 micrograms/l, and 69 micrograms/l respectively. The excretion rates were 4.20 mg/h for phenol, 2.4 mg/h for p-cresol, 3.3 mg/h for o-cresol; and 1.5 mg/h for 2,5-xylenol. The highest concentrations of the mentioned compounds were detected in urine collected between eight and 10 hours from the beginning of exposure. The kinetics of excretion are considered.

Chemical Industry↗
PubMed1993

Suppressive effect of an oral sorbent on the accumulation of p-cresol in the serum of experimental uremic rats.

Serum p-cresol and phenol are markedly accumulated in uremic patients. To determine if an oral sorbent (AST-120) can decrease their serum concentrations in the uremic state, an oral sorbent was administered to experimental nephrectomized uremic rats. In uremic rats fed with oral sorbent, the serum concentration and the urinary excretion of p-cresol were markedly and significantly lower than those in control uremic rats, while those of phenol tended to be low in the uremic rats with oral sorbent as compared with control uremic rats. The concentrations of serum creatinine and blood urea nitrogen were significantly decreased in the uremic rats with oral sorbent. These findings demonstrate that oral sorbent adsorbs especially p-cresol in the intestine and prevents the accumulation of p-cresol in the serum of uremic rats.

Administration, Oral↗