SEARCH · Search PubMed

Results for “RESORCINOL”

Search indexed PubMed citations on genomics, clinical trials, systematic reviews and public health. Explore titles, authors and supplied subject terms, then open the PubMed record.

SourceResearch connectionFrom yearThrough year

Quote a phrase for an exact phrase match. Source license links do not imply unrestricted reuse.

At least 415 records · Page 23Linked to original sources

PubMed1992

Sequential Transhydroxylations Converting Hydroxyhydroquinone to Phloroglucinol in the Strictly Anaerobic, Fermentative Bacterium Pelobacter massiliensis.

The recently isolated fermenting bacterium Pelobacter massiliensis is the only strict anaerobe known to grow on hydroxyhydroquinone (1,2,4-trihydroxybenzene) as the sole source of carbon and energy, converting it to stoichiometric amounts of acetate. In this paper, we report on the enzymatic reactions involved in the conversion of hydroxyhydroquinone and pyrogallol (1,2,3-trihydroxybenzene) to phloroglucinol (1,3,5-trihydroxybenzene). Cell extracts of P. massiliensis transhydroxylate pyrogallol to phloroglucinol after addition of 1,2,3,5-tetrahydroxybenzene (1,2,3,5-TTHB) as cosubstrate in a reaction identical to that found earlier with Pelobacter acidigallici (A. Brune and B. Schink, J. Bacteriol. 172:1070-1076, 1990). Hydroxyhydroquinone conversion to phloroglucinol is initiated in cell extracts without an external addition of cosubstrates. It involves a minimum of three consecutive transhydroxylation reactions characterized by the transient accumulation of two different TTHB isomers. Chemical synthesis of the TTHB intermediates allowed the resolution of the distinct transhydroxylation steps in this sequence. In an initial transhydroxylation, the hydroxyl group in the 1-position of a molecule of hydroxyhydroquinone is transferred to the 5-position of another molecule of hydroxyhydroquinone to give 1,2,4,5-TTHB and resorcinol (1,3-dihydroxybenzene) as products. Following this disproportionation of hydroxyhydroquinone, the 1,2,4,5-isomer is converted to 1,2,3,5-TTHB, an enzymatic activity present only in hydroxyhydroquinone-grown cells. Finally, phloroglucinol is formed from 1,2,3,5-TTHB by transfer of the 2-hydroxyl group to either hydroxyhydroquinone or resorcinol. The resulting coproducts are again cosubstrates in earlier reactions of this sequence. From the spectrum of hydroxybenzenes transhydroxylated by the cell extracts, the minimum structural prerequisites that render a hydroxybenzene a hydroxyl donor or acceptor are deduced.

Journal Article↗

PubMed1995

Close Correlation between Heat Shock Response and Cytotoxicity in Neurospora crassa Treated with Aliphatic Alcohols and Phenols.

In Neurospora crassa the aliphatic alcohols methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 2-butanol, isobutanol, ethylene glycol, glycerol, and allyl alcohol and the phenolic compounds phenol, hydroquinone, resorcinol, pyrogallol, phloroglucinol, sodium salicylate, and acetylsalicylic acid were analyzed with respect to their capacities to induce heat shock proteins (HSP) and to inhibit protein synthesis. Both the alcohols and phenols showed the greatest levels of HSP induction at concentrations which inhibited the overall protein synthesis by about 50%. The abilities of the different alcohols to induce the heat shock response are proportional to their lipophilicities: the lipophilic alcohol isobutanol is maximally inductive at about 0.6 M, whereas the least lipophilic alcohol, methanol, causes maximal induction at 5.7 M. The phenols, in general, show a higher capability to induce the heat shock response. The concentrations for maximal induction range between 25 mM (sodium salicylate) and 100 mM (resorcinol). Glycerol (4.1 M) shifted the concentration necessary for maximal HSP induction by hydroquinone from 50 to 200 mM. The results reveal that the induction of HSP occurs under conditions which considerably constrain cell metabolism. The heat shock response, therefore, does not represent a sensitive marker for toxicity tests but provides a good estimate for the extent of cell damage.

Journal Article↗

PubMed1999

Gelatin-derived bioadhesives for closing skin wounds: an in vivo study.

Bioadhesives have been used in surgery as hemostatic and wound healing agents. GRF (gelatin + resorcinol + formaldehyde) glue, composed of a mixture of gelatin and resorcinol polymerized by the addition of formaldehyde, has been used for this purpose. Widespread acceptance of the GRF glue, however, has been limited by reports of cytotoxicity due to its release of formaldehyde upon degradation. It has been suggested by Wertzel et al. that the cytotoxicity problem of GRF glue may be overcome by changing its cross-linking method. The study was, therefore, undertaken to assess the feasibility of using a water-soluble carbodiimide or genipin to cross-link gelatin as new bioadhesives to close skin wound lesions in a rat model. Formaldehyde-cross-linked counterpart (GRF glue) and a resorbable suture were used as controls. It was noted that the tensile strength of the skin across each wound treated by either application of test glues or suture increased consistently with time during the healing process. Also, the wounds repaired by test glues or suture caused no calcification. The suture used in the study was completely resorbed at the wound area in about 6 days postoperatively. However, the durations required to completely resorb the carbodiimide- or genipin-cross-linked glues were approximately the same (9 days), while it took about 14 days to completely resorb the formaldehyde-cross-linked glue. The healing process for the suture wound repaired was more rapid than those treated by test glues. Of the test glues, the wounds treated by the carbodiimide- or genipin-cross-linked glues induced less inflammatory response and recovered sooner than that treated by the formaldehyde-cross-linked glue. This indicated that the biocompatibility of the carbodiimide- or genipin-cross-linked glues was superior to the formaldehyde-cross-linked glue. The results of this study may serve as a preliminary experimental model for the further investigation of both the carbodiimide- and genipin-cross-linked glues when applied to human skin closure.

Animals↗

PubMed1976

Effect of reductones on glyoxalase I1.

The effect of some reductones on glyoxalase I prepared from animal and microbial origins has been studied. The enzyme was extracted from ox liver or baker's yeast and partially purified by ammonium sulfate fractionation, gel filtration and ion exchange chromatography. Aliphatic reductones such as ascorbic acid, ascorbic acid 3-phosphate and triose reductone showed strong to medium inhibition, while dehydroascorbic acid showed no inhibition. Kinetic analysis indicated that the inhibition mechanism of ascorbic acid was uncompetitive. Varying extents of inhibition were observed among three kinds of diphenols belonging to aromatic reductones. They were in the order of increasing inhibitory power resorcinol, hydroquinone and catechol for the ox liver enzyme, and catechol, resorcinol and hydroquinone for the yeast enzyme. p-Benzoquinone, an oxidized reductone, exhibited marked inhibition on both enzymes. Its action seemed due to reaction with amino and/or sulfhydryl functions of enzyme protein and those of glutathione, one of the substrates.

Animals↗

PubMed1999

Peeling agents: toxicological and allergological aspects.

BACKGROUND: The use of peeling agents is very common in clinical practice. However, despite the overall good safety profile, it is not without any inherent risk; therefore, clinicians should be adequately informed about potential risk in order to avoid or prevent them. OBJECTIVE: This paper reviews toxicological and allergological aspects of peeling agents in general, also beyond their actual use in peeling procedures. Toxic and allergic reactions from peeling agents are rather uncommon and have been rarely reported in association with the medical use of peels. METHODS: Systemic toxic effects may essentially derive from phenol and potentially from two phenol derivatives, resorcinol and salicylic acid. A complete understanding of the toxicological profile of peeling agents, along with a correct execution of the technique and a carefully selection of patients, can help avoid serious side effects. RESULTS: Allergic contact reactions occur most frequently with resorcinol, while most peeling agents are only rare sensitizers or appear to be free of true sensitizing power. Other types of hypersensitivity response seem to be very rare.

Chemexfoliation↗

PubMed2001

Bioconversion of 1,3 dinitrobenzene by Micrococcus colpogenes strain MCM B410: quantitation and characterization of the intermediates.

Micrococcus colpogenes MCM B 410, indigenous to soil, collected from nitro aromatic contaminated site, could transform 1,3 dinitrobenzene (m-DNB) initially to m-nitroaniline, m-nitrophenol, m-aminophenol and resorcinol at 30 degrees C under shake culture condition. Carbon mineralization studies with unlabelled and radio labelled 1,3 (U14 C) dinitrobenzene subtrates indicated that the above metabolities appeared within 4 days. After 7 days incubation a significant traction of the source compound was degraded to C Q through aliphatic acids. Presence of nitro aryl reductase, aryl monooxygenase and resorcinol 1,3 di oxygenase was also noted in the sonicated cell mass.

Carbon↗

PubMed1976

Simultaneous quantitation of 4-hydroxy-3-methoxymandelic (vanilmandelic) and 4-hydroxy-3-methoxyphenylacetic (homovanillic) acids in human urine.

We describe a simultaneous analysis for vanilmandelic and homovanillic acids in urine. An aliquot of a final extract, containing phenylpropriopionic acid as external standard, is dried, an internal standard (resorcinol) is added, and the mixture is silylated and chromatographed. The two compounds are identified from their characteristic retention times and from their elution behhavior in relation to four different marker compounds (the external and internal standards and two other naturally occurring compounds, p-hydroxyphenylacetic and hippuric acids) and are quantitated from their relative response factors. Within-run precision (CV) varied from 2 to 14% for vanilmandelic acid and 1 to 18% for homovanillic acid. The ratio of the amount of phenylpropionic acid extracted to the amount of added resorcinol found is a useful quality-control index. Values for vanilmandelic acid obtained by this method and by the technique of Pisano et al. [Clin. Chim. Acta 7, 285 (1962)] correlated well (r = 0.844).

Chromatography, Gas↗

PubMed2002

Enzymological aspects of bioconversion of m-dinitrobenzene.

Three main enzymes, responsible for bioconversion of 1,3 dinitrobenzene (m-DNB) by Micrococcus colpogenes MCM B 410, were isolated from the sonicated cell mass, grown in presence of m-DNB in a synthetic medium, for 7 days. The soluble proteins were separated by differential precipitation and also separated by native PAGE. Each fraction obtained from both the protocols, was tested for nitro aryl reductase, aryl mono oxygenase and resorcinol 2,3 dioxygenase. The apparent molecular weight of the proteins were nitro aryl reductase (30 kDa), aryl mono oxygenase (110 kDa) and resorcinol 2,3 di oxygenase (65 kDa).

Biotransformation↗

PubMed2004

[Mannosylation of ligand binding domain 2 of HER-2/neu].

AIM: To establish a new method for protein mannosylation, which will facilitate the study of antigen presentation mediated by mannose receptor. METHODS: Recombinant HER-2/neu ligand binding domain 2 (LBD2) was purified through DEAE sepharose FF column and cobalt-based affinity resins. LBD2 protein was mannosylated in-vitro,and then analyzed by MALDI-TOF-MS and resorcinol-sulfuric acid method. RESULTS: The purity of LBD2 obtained was 90%. Analysis of MALDI-TOF-MS and resorcinol-sulfuric acid method suggested LBD2 was mannosylated. CONCLUSION: LBD2 neoglycoprotein has been obtained, which lays the foundation for the study of antigen uptake and presentation mediated by mannose receptor and the development of tumor vaccine.

Binding Sites↗

PubMed2005

Production of auxin and related compounds by the plant parasitic nematodes Heterodera schachtii and Meloidogyne incognita.

Mass spectrometric analysis revealed the presence of auxin, mainly in conjugated form, in secretions of Heterodera schachtii and Meloidogyne incognita, with or without treatment with DMT or resorcinol. M. incognita showed the highest production rates, though treatment of M. incognita with resorcinol had a negative effect on auxin production. Analysis of auxin precursor molecules in lysates of H. schachtii, M. incognita and Caenorhabditis elegans suggested that auxin is most probably a degradation product of tryptophan and that auxin may be synthesized via several intermediates, including indole-3-acetamide which is an intermediate of a pathway so far only characterized in bacteria. Furthermore, high levels of anthranilate, a degradation product of tryptophan in animals, but possibly also a precursor for auxin were detected.

Animals↗

PubMed2006

[Determination of dihydroxybenzenes using high performance liquid chromatography with acidic potassium permanganate chemiluminescence].

A sensitive, selective and simple post-column chemiluminescence (CL) detection method for simultaneously determining catechol, resorcinol, hydroquinone has been developed based on high performance liquid chromatography (HPLC) coupled with CL detection using reaction of dihydroxybenzenes with acidified potassium permanganate solution with the enhancing effect of formic acid. The optimal conditions for the CL detection and HPLC separation were achieved. Dihydroxybenzene isomers were baseline separated at column temperature of 25 degrees C using a mobile phase of methanol-0.1 mmol/L beta-cyclodextrin aqueous solution (30/70, v/v) with an isocratic elution program and the mobile phase matched well the CL detection. For all compounds, the linear ranges of the CL detection were about two orders of magnitude. The detection limits were 3.2 microg/L for hydroquinone, 4.7 microg/L for resorcinol and 5.2 microg/L for catechol. Combining with solid phase extraction, the proposed method was successfully applied to the determination of dihydroxybenzenes in river water. The recoveries for the three dihydroxybenzenes were 92.1%-95.4%.

English Abstract↗

PubMed1991

Kinetic and isotopic studies of the oxidative half-reaction of phenol hydroxylase.

Phenol hydroxylase, an FAD-containing monooxygenase, catalyzes the conversion of substituted phenols to the corresponding catechol. Use of metapyrocatechase, capable of dioxygenation of several catechols to give highly absorbing products, permitted determination of the time course of product release from phenol hydroxylase. Product dissociated prior to complete reoxidation of the enzyme, most likely concomitant with formation of the 4a-hydroxyflavin species (intermediate III). Deuterated phenol and thiophenol exhibited no kinetic isotope effect during the oxidative half-reaction. Isotope effects of 1.7 to 3.7 were found with resorcinol for the conversion of the second intermediate to intermediate III. These effects limited the possible models for phenol hydroxylation. An attempt was made to distinguish whether the spectrum of intermediate II is due entirely to that of the flavin moiety of phenol hydroxylase or whether some radical intermediate form involved in the formation of catechol makes a significant visible contribution. Reduced native and 6-hydroxy-FAD phenol hydroxylase were reacted with oxygen and resorcinol in order to provide evidence for the identity of intermediate II.

Isotopes↗

PubMed1989

Interaction of thiocyanate with horseradish peroxidase. 1H and 15N nuclear magnetic resonance studies.

Interaction of thiocyanate with horseradish peroxidase (HRP) was investigated by relaxation rate measurements (at 50.68 MHz) of the 15N resonance of thiocyanate nitrogen and by following the hyperfine shifted ring methyl proton resonances (at 500 MHz) of the heme group of SCN-.HRP solutions. At pH 4.0, the apparent dissociation constant (KD) for thiocyanate binding to HRP was deduced to be 158 mM from the relaxation rate measurements. Chemical shift changes of 1- and 8-ring methyl proton resonances in the presence of various amounts of thiocyanate at pH 4.0 yielded KD values of 166 and 136 mM, respectively. From the pH dependence of KD and the 15N resonance line width, it was observed that thiocyanate binds to HRP only under acidic conditions (pH less than 6). The binding was found to be facilitated by protonation of an acid group on the enzyme with pKa 4.0. The pH dependence of the 15N line width as well as the apparent dissociation constant were quantitatively analyzed on the basis of a reaction scheme in which thiocyanate in deprotonated ionic form binds to the enzyme in protonated acidic form. The KD for thiocyanate binding to HRP was also evaluated in the presence of an excess of exogenous substrates such as resorcinol, cyanide, and iodide ions. It was found that the presence of cyanide (which binds to heme iron at the sixth coordination position) and resorcinol did not have any effect on the binding of thiocyanate, indicating that the binding site of the thiocyanate ion is located away from the ferric center as well as from the aromatic donor binding site. The KD in the presence of iodide, however, showed that iodide competes with thiocyanate for binding at the same site. The distance of the bound thiocyanate ion from the ferric center was deduced from the 15N relaxation time measurements and was found to be a 6.8 A. From the distance as well as the change in the chemical shifts and line width of 1- and 8-methyl proton resonances, it is suggested that the binding site of thiocyanate may be located near heme, placed symmetrically with respect to 1- and 8-methyl groups of the heme of HRP. Similarity in the modes of binding of iodide and thiocyanate suggests that the oxidation of thiocyanate ion by H2O2 may also proceed via the two-electron transfer pathway under acidic conditions, as is the case for iodide.

Horseradish Peroxidase↗

PubMed1989

Promotion by dihydroxybenzene derivatives of N-methyl-N'-nitro-N-nitrosoguanidine-induced F344 rat forestomach and glandular stomach carcinogenesis.

Modifying effects of resorcinol, hydroquinone, p-tert-butylcatechol (PTBC), p-methylcatechol (PMC), and o-methylcatechol on N-methyl-N'-nitro-N-nitrosoguanidine (MNNG)-induced forestomach and glandular stomach carcinogenesis were investigated in F344 rats. Groups of 15 to 16 male 6-wk-old animals were given a single intragastric administration of 150 mg/kg of body weight of MNNG and starting 1 wk later were administered powdered diet containing 0.8% resorcinol, 0.8% hydroquinone, 1.5% PTBC, 1.5% o-methylcatechol, 1.5% PMC, or basal diet alone for 51 wk. Additional groups of 10 to 15 rats each were treated with the phenolic compounds or received basal diet without prior carcinogen exposure. Histological examination after sacrifice at Wk 52 revealed that squamous cell carcinoma development in the forestomachs of rats treated with MNNG followed by PTBC (75%, P less than 0.001) or MNNG followed by PMC (100%, P less than 0.001) was significantly greater than in animals receiving MNNG alone (20%). Treatment with PMC alone also resulted in a 40% yield of papilloma. In the glandular stomach, incidences of adenomatous hyperplasias in rats treated with MNNG followed by PTBC (31.3%, P less than 0.05) or PMC (100%, P less than 0.001) and the incidence of adenocarcinomas in rats treated with MNNG followed by PMC (100%, P less than 0.001) were significantly higher than in controls. In addition, PMC alone induced a 100% yield of adenomatous hyperplasias and 6.7% of adenocarcinomas. Thus, the results demonstrated that PTBC and PMC treatment significantly enhances forestomach and glandular stomach carcinogenesis and that PMC itself may possess weak carcinogenic potential in these organs. The ortho-position appears to be important for this dihydroxybenzene activity.

Adenocarcinoma↗

PubMedDate not supplied

[Inhibition by diphenols of the induction of micronuclei by gamma-radiation].

A study was made of the influence of diphenols (for instance, resorcinol, hydroquinone, and pyrocatechin) on gamma-radiation induction of micronuclei (1.5 Gy). The position of the diphenol molecule hydroxyl group (the isomeric effect) was shown to influence their antimutagenic activity. This antimutagenic effect of the diphenols is associated with their ability to produce semiquinone and quinone forms which are peculiar for the process of oxidation of pyrocatechin (ortho-) and hydroquinone (para-) as opposed to resorcinol (meta-position of the hydroxyl group).

Animals↗

PubMed1985

[Distribution of elastic bodies (elastic globes) in healthy human skin. Studies with a dense grid].

Since the turn of the century, there have been descriptions of corpuscular structures in the human skin. These are situated at the epidermal-corial junction zone. They can be visualized well with resorcinol-fuchsin staining according to Weigert. They may attain forensic significance in the topographic assignment of isolated skin fragments to certain body regions. The research results available so far, which are in some cases contradictory, were checked and the investigations were continued. A total of 584 skin punch samples were taken from the trunk and limbs of a 39-year-old male corpse. Of these, a total of 1752 paraffin serial sections (resorcinol-fuchsin staining) were prepared and investigated for the occurrence of elastic bodies. The investigation essentially showed that in almost all serial sections, elastic bodies were found to have a frequency concentration at points on the limbs. It could not be established that there was a sharp separation of skin areas containing elastic globes and skin areas free of elastic globes. The distribution of elastic bodies is evidently subject to a pattern of its own, which does not display any interrelationships with that of the skin appendages (apocrine and eccrine sweat glands, sebaceous glands, and male body hair). Because the skin of the trunk and the limbs is relatively regularly interspersed with elastic globes, there can only be used in connection with other features (e.g. thickness of the epidermis, skin appendages) to assign isolated skin fragments to certain regions of the body.

Adult↗

PubMedDate not supplied

Liquid chromatographic determination of intermediates in D&C Yellow No. 7 and D&C Yellow No. 8.

A sensitive, reproducible method that uses liquid chromatography in the reverse phase mode has been developed for the determination of phthalic acid, resorcinol, and 2-(2',4'-dihydroxybenzoyl)benzoic acid in D&C Yellow No. 7 and D&C Yellow No. 8. The method uses a 10 micron, C-8 column, a 1% acetic acid-methanol gradient, and UV absorption detection at 280 nm. Average recoveries of phthalic acid, resorcinol, and 2-(2',4'-dihydroxybenzoyl)benzoic acid were 100, 98, and 102%, respectively, from fluorescein standard (certifiable as D&C Yellow No. 7) spike with each compound at levels ranging from 0.13 to 1.3%.

Chromatography, Liquid↗

PubMed1965

THE FLUORIMETRIC MICRODETERMINATION OF GLYOXYLIC ACID IN BLOOD, URINE AND BACTERIAL EXTRACTS.

1. A spectrophotofluorimetric method for the determination of glyoxylic acid in biological materials is described. 2. The method is based on the reaction between glyoxylic acid and resorcinol in acid solution, a fluorescent complex being obtained on the subsequent addition of alkali. 3. The reaction was found to be sensitive and highly specific, the minimum detectable amount of glyoxylic acid being 1.35x10(-8) mole. 4. The urinary excretion of glyoxylic acid by ten normal adults ranged from 1.4 to 4.7mg./24hr. Small but measurable amounts of glyoxylic acid were found in cell-free extracts of Pseudomonas oxalaticus OX1 grown on oxalic acid as a source of carbon. No glyoxylic acid was detected in human serum.

Acetates↗