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At least 19 recordsLinked to original sources
PubMed1993

Metabolism of chlorinated guaiacols by a guaiacol-degrading Acinetobacter junii strain.

The metabolism of chlorinated guaiacols by a pure bacterial strain identified by its ability to use guaiacol as the sole carbon and energy source was studied. This strain, identified as Acinetobacter junii 5ga, was unable to grow on several chlorinated guaiacols and catechols. However, strain 5ga grown on guaiacol degraded 4- and 5-chloroguaiacol and 4,5-dichloroguaiacol. Under the same conditions, these cells did not degrade 6-chloroguaiacol, 4,6-dichloroguaiacol, 4,5,6-trichloroguaiacol, or tetrachloroguaiacol, suggesting that the substitution at the 6 position in the ring prevents metabolism of the compound. Degradation of 4-chloroguaiacol was dependent on the initial ratio between the chlorinated compound and viable cells. Transient formation of chlorocatechols resulting from incubation of cells with 4-chloroguaiacol or 4,5-dichloroguaiacol was suggested by UV spectroscopy. Gas chromatography analyses of samples from cultures of strain 5ga grown on guaiacol and incubated with 4- and 4,5-dichloroguaiacol confirmed the presence of 4-chlorocatechol and 4,5-dichlorocatechol, respectively. The formation of the latter was corroborated by gas chromatography-mass spectrometry. Thus, this strain is able to initiate metabolism of specific chlorinated guaiacols by O-demethylation. The starting chlorinated guaiacols and their O-demethylated metabolites inhibited the growth of A. junii 5ga on guaiacol.

Acinetobacter↗
PubMed1991

[Toxicologic investigations of selected phenolic compounds. I. Acute and subacute toxicity of guaiacol, methyl-guaiacol and syringol].

The aim of the investigations were determination of acute (A-DL50) and subacute (C-DL50) toxicity of guaiacol, methyl-guaiacol and syringol. White Wistar male rats, body weight 250 g +/- 20, were used. From the data obtained it was concluded that tested compounds could be classified to the fourth toxicity class (Hodge-Sterner classification). Cumulation coefficients show that no cumulation of there compounds occurs in a rat organism.

Animals↗
PubMed1995

Oxidation of guaiacol by lignin peroxidase. Role of veratryl alcohol.

We have investigated the lignin peroxidase-catalyzed oxidation of guaiacol and the role of veratryl alcohol in this reaction by steady-state and pre-steady-state methods. Pre-steady-state kinetic analyses demonstrated that guaiacol is a good substrate for both compounds I and II, the two- and one-electron oxidized enzyme intermediates, respectively, of lignin peroxidase. The rate constant for the reaction with compound I is 1.2 x 10(6) M-1s-1. The reaction of guaiacol with compound II exhibits a Kd of 64 microM and a first-order rate constant of 17 s-1. Oxidation of guaiacol leads to tetraguaiacol formation. This reaction exhibits classical Michaelis-Menten kinetics with a Km of 160 microM and a kcat of 7.7 s-1. Veratryl alcohol, a secondary metabolite of ligninolytic fungi, is capable of mediating the oxidation of guaiacol. This was shown by steady-state inhibition studies. Guaiacol completely inhibited the oxidation of veratryl alcohol, whereas veratryl alcohol had no corresponding inhibitory effect on guaiacol oxidation. In fact, at low guaiacol concentrations, veratryl alcohol stimulated the rate of guaiacol oxidation. These results collectively demonstrate that veratryl alcohol can serve as a mediator for phenolic substrates in the lignin peroxidase reaction.

Basidiomycota↗
PubMed1992

An unexpected side reaction in the guaiacol assay for peroxidase.

In routine guaiacol assays for thyroid peroxidase and lactoperoxidase employing a newly purchased bottle of guaiacol from Aldrich Chemical Co., we were surprised to find the formation of a blue color instead of the expected amber color classically associated with this assay. This was observed also with horseradish, myelo-, and cytochrome c peroxidase. The blue color (Amax approximately 650 nm) was not formed with guaiacol reagents obtained from two other chemical companies, nor was it seen with a bottle of old Aldrich guaiacol that had been in use in the laboratory for more than 10 years. In the present investigation we provide evidence that formation of the blue color is closely associated with the presence of a low concentration of catechol (approximately 0.5 mol%) in the new Aldrich guaiacol reagent. Catechol itself, even in much higher concentration, is a very weak donor for peroxidase, forming a light pink color. The blue color in Aldrich new guaiacol is not formed to the exclusion of 470-nm-absorbing product(s). Formation of the latter is, however, inhibited, and use of Aldrich new guaiacol for assay leads to low values for peroxidase activity. Other dihydroxyphenols (resorcinol and hydroquinone) do not mimic the action of catechol in formation of the blue color. Resorcinol is a very potent inhibitor of peroxidation of guaiacol. Possible schemes are proposed for formation of the products that may be associated with the amber and blue colors.

Aging↗
PubMed1985

The demethylation of guaiacol by a new bacterial cytochrome P-450.

Spectroscopic studies were carried with a cytochrome P-450 in Moraxella sp., strain GU2, that could grow on guaiacol or 2-ethoxyphenol as the sole source of carbon and energy. The dissociation constant of the guaiacol-cytochrome complex was estimated to 0.15 microM, as determined in vivo or using the cell soluble extract. Cytochrome P-450 could also bind 2-ethoxyphenol, 2-propoxyphenol, and 2-butoxyphenol, and the dissociation constants have been determined in each case. Metyrapone depressed the degradation of guaiacol by whole bacteria, and was bound competitively to guaiacol with a constant of about 0.8 mM. Some catechol was excreted by the bacteria when growing on either guaiacol or 2-ethoxyphenol. Catechol and the other product of guaiacol demethylation, formaldehyde, were further oxidized by the bacteria. All the data available so far are consistent with cytochrome P-450 in Moraxella GU2 as a hydroxylase for the guaiacol side chain, behaving as a nonspecific O-dealkylase with broad specificity for guaiacol and homologous compounds with a longer carbon part in the side chain.

Catechols↗
PubMed1975

Titration study of guaiacol oxidation by horseradish peroxidase.

Titration of guaiacol by hydrogen peroxide in the presence of a catalytic amount of horseradish peroxidase shows that the reduction of hydrogen peroxide proceeds by the abstraction of two electrons from a guaiacol molecule. In the same way, it can be demonstrated that 0.5 mol of guaiacol can reduce, at low temperature, 1 mol of peroxidase compound I to compound II. Moreover, the reaction between equal amounts of compound I and guaiacol at low temperature produces the native enzyme. A reaction scheme is proposed which postulates that two electrons are transferred from guaiacol to compound I giving ferriperoxidase and oxidized guaiacol with the intermediary formation of compound II. The direct two-electron transfer from guaiacol to compound I without a dismutation of product free radicals must be considered as an exception to the general mechanism involving a single-electron transfer.

Electron Transport↗
PubMed1991

Effects of metoxibutropate, ibuprofen and guaiacol on the gastrointestinal system.

In previous studies we have shown that ibuprofen, guaiacol and the guaiacol ester of ibuprofen (I.N.N. metoxibutropate) are able to inhibit in-vitro prostaglandin synthesis. In the present study we have evaluated the effect of ibuprofen, guaiacol and metoxibutropate on the gastrointestinal system. Oral treatment with equimolar increasing doses of the three drugs produced a progressive inhibition of prostaglandin biosynthesis in the intestinal tract, without any effect on the rate of intestinal propulsion. Further studies evaluated the gastric tolerance of a molar dose of ibuprofen causing ulceration in 50% of the animals. After single and repeated administration of guaiacol and of the guaiacol ester of ibuprofen, the percentage of animals with gastric damage was very low and the index of ulceration seemed rather moderate. Our results show that although guaiacol is able to inhibit prostaglandin biosynthesis like a classic NSAID, it does not induce gastric damage. For these reasons it is justified to combine guaiacol with ibuprofen in order to reduce gastric erosions induced by a classic antiinflammatory drug.

Animals↗
PubMed1982

[Secretagogue action of glyceryl guaiacolate in tracheal submucosal glands (author's transl)].

The effects of glyceryl guaiacolate on secretory activities of tracheal secretory cells and on behavior of mucus glycoprotein in these cells were investigated histologically and histochemically using isolated canine trachea. Following glyceryl guaiacolate treatment, the number of total glycoprotein-containing goblet cells (GC) did not change. The numbers of acid glycoprotein (AGP)-, neutral glycoprotein (NGP)-, and sulphated glycoprotein (SGP)-containing GC were also unaltered in a concentration range of 10(-7) to 10(-4)M. On the other hand the acinar inner diameter of the submucosal gland (SG) and the acinar inner diameter to wall ratio significantly increased, while thickness of acinus significantly decreased with 10(-6), 10(-5) and 10(-4)M glyceryl guaiacolate. AGP and SGP contents in glandular cells markedly decreased, while the ratio of the numbers of AGP- to NGP-containing glandular cell were the same, suggesting that glyceryl guaiacolate does not change the quality of mucus glycoprotein in GC and SG. Glyceryl guaiacolate produced a marked increase in total saccharide, protein, and N-acetylhexosamine concentrations in the incubation fluid. These findings suggest that glyceryl guaiacolate has no influence on the secretory activity of GC, but markedly stimulates the activity of SG. The secretagogue effect of the agent would be ascribable to stimulation of mucus discharge, but not stimulation of mucus synthesis.

Animals↗
PubMed1985

NADPH oxidation catalyzed by the peroxidase/H2O2 system. Guaiacol-mediated and scopoletin-mediated oxidation of NADPH to NADPH+.

We have examined the respective roles played by guaiacol and scopoletin in NADPH oxidation catalyzed by the peroxidase/H2O2 system. It was shown that NADPH was not oxidized by either the horseradish or lactoperoxidase/H2O2 systems alone; oxidation occurred immediately after the addition of guaiacol or scopoletin. In both cases, the oxidation product was enzymatically active NADP+. Differences were observed in the NADPH oxidation mechanism depending on whether guaiacol or scopoletin was the mediator molecule. In guaiacol-mediated NADPH oxidation, the stoichiometry between H2O2 and oxidized NADPH was about 1; superoxide dismutase did not affect the oxidation rate. In scopoletin-mediated oxidation, the stoichiometry was much higher (1:14 in the present experiments); superoxide dismutase considerably increased the oxidation rate. It is concluded that catalysis of NADPH oxidation by the horse radish peroxidase/H2O2 system requires the presence of a mediator molecule. The NADPH oxidation mechanism depends on the intermediary oxidation state of this molecule.

Catalysis↗
PubMed1978

Microbial catabolism of vanillate: decarboxylation to guaiacol.

A novel catabolic transformation of vanillic acid (4-hydroxy-3-methoxybenzoic acid) by microorganisms is reported. Several strains of Bacillus megaterium and a strain of Streptomyces are shown to convert vanillate to guaiacol (o-methoxyphenol) and CO2 by nonoxidative decarboxylation. Use of a modified most-probable-number procedure shows that numerous soils contain countable numbers (10(1) to 10(2) organisms per g of dry soil) of aerobic sporeformers able to convert vanillate to guaiacol. Conversion of vanillate to guaiacol by the microfloras of most-probable-number replicates was used as the criterion for scoring replicates positive or negative. Guaiacol was detected by thin-layer chromatography. These results indicate that the classic separations of catabolic pathways leading to specific ring-fashion substrates such as protocatechuate and catechol are often interconnectable by single enzymatic transformations, usually a decarboxylation.

Bacillus megaterium↗
PubMed1997

The selective capsaicin antagonist capsazepine abolishes the antinociceptive action of eugenol and guaiacol.

The dental phenolic medicaments, eugenol and guaiacol, are partly similar in chemical structure to capsaicin, the pungent constituent of chili peppers, which selectively activates sensory neurons via a specific receptor. We have previously demonstrated that these phenolic compounds show capsaicin-like action. In the present study, an attempt was made to investigate the possibility that these compounds interact with the same cellular site as capsaicin, by using capsazepine, a selective and competitive anta-gonist of capsaicin. Intrathecal (i.t.) treatment with eugenol (12.5 to 50 micrograms), guaiacol (25 to 150 micrograms), or capsaicin (1 to 4 micrograms) for 24 h dose-dependently inhibited the formalin-induced nociceptive response. Capsazepine (5, 10 micrograms, i.t.) shifted these dose-response curves in parallel to the right. Similarly, capsazepine abolished antinociceptive effects of eugenol (50 micrograms), guaiacol (150 micrograms), or capsaicin (2 micrograms) in the acetic acid writhing test. These results suggest that eugenol and guaiacol may exert their antinociceptive effects via the capsaicin receptor located on sensory terminals in the spinal cord.

Analgesics, Non-Narcotic↗
PubMed1997

Identification of the colored guaiacol oxidation product produced by peroxidases.

Oxidation of guaiacol by peroxidases in the presence of H2O2 is the basis for a widely used colorimetric assay. However, the nature of the assay product, which has an absorption maximum around 470 nm, had not been determined. In the present study, we combined HPLC with a rapid scanning uv-visible detector and observed a single product with a spectrum identical to the assay product from the reaction catalyzed by lactoperoxidase. Analysis of the reaction product using on-line HPLC with atmospheric pressure chemical ionization detection (LC-APCI/MS) yielded a mass spectrum consistent with 3,3 '-dimethoxy-4,4'-biphenylquinone. A minor reaction product was observed with mass spectrum consistent with 3,3'-dimethoxy-4,4'-dihydroxybiphenyl. The presence of a catechol impurity in guaiacol was previously shown to yield an additional product from peroxidase-mediated oxidation based on its visible absorption (Taurog et al., 1992 Anal. Biochem. 205, 271-277). When such an incubation mixture was analyzed using LC-APCI/MS, a product with mass spectrum consistent with 3-methoxy-2',3',4-trihydroxybiphenyl was observed. Identification of such a heterodimeric product supports the previously proposed mechanism for catechol interference in the guaiacol assay as well as the radical nature of peroxidase-catalyzed oxidation of phenols.

Biphenyl Compounds↗
PubMed1992

Solid-phase extraction and HPLC determination of 4-vinyl guaiacol and its precursor, ferulic acid, in orange juice.

This study is undertaken to develop a simplified, rapid method to determine both immediate and potential off odors due to 4-vinyl guaiacol and its odorless precursor, ferulic acid, from a single sample preparation and chromatographic analysis. Orange juice sample preparation consists of a simple, C18 solid phase extraction. Utilizing a 5-microns, 25-cm, C18 column, both compounds can be separated within 40 min using a one-step, linear gradient beginning with an aqueous 12% tetrahydrofuran (THF)-5% acetonitrile mixture and ending with 35% aqueous THF. Hesperidin and nariutin have been identified as the compounds that interfered with the ultraviolet (UV) determination of sinapic and caffeic acids. Fluorescence detection with wavelength programming offers optimal sensitivity and selectivity. Recoveries of 4-vinyl guaiacol and ferulic acid range from 90 to 103%. Detection limits are 1 ppm and 5 ppm for ferulic acid and 4-vinyl guaiacol, respectively. Other hydroxycinnamic acids such as coumaric, sinapic, and caffeic acids may also be determined from the same chromatogram.

Beverages↗
PubMed1988

Hydroxylation and dechlorination of chlorinated guaiacols and syringols by Rhodococcus chlorophenolicus.

We show that Rhodococcus chlorophenolicus PCP-I, a polychlorophenol degrader, also degrades various chlorine-substituted guaiacols (2-methoxyphenols) and syringols (2,6-dimethoxyphenols). The substrates investigated were tetrachloroguaiacol, 3,4,6- and 3,5,6-trichloroguaiacol, 3,5- and 3,6-dichloroguaiacol, trichlorosyringol, and 3,5-dichlorosyringol. The first step was a hydroxylation, probably in a position para to the preexisting hydroxyl. Tetrachloroguaiacol and trichlorosyringol, with a chlorine substituent in the para position, were both hydroxylated and dechlorinated. The optimum temperature for degradation of polychlorinated guaiacols and syringols was 37 to 41 degrees C. Degradation of polychlorinated phenols, guaiacols, and syringols by R. chlorophenolicus was inducible, and induction was controlled coordinately.

Biodegradation, Environmental↗