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PubMed1994

Kneglomeratanol, kneglomeratanones A and B, and related bioactive compounds from Knema glomerata.

One new phenylalkyl phenol, kneglomeratanol [1], and two new acetophenones, kneglomeratanones A [2] and B [3], together with ten known compounds, 3-(12'-phenyldodecyl)-phenol [4], 3-(10'-phenyldecyl)-phenol [5], 5-pentadecylresorcinol [6], 5-(10'-phenyldecyl)-resorcinol [7], 5-(12'-phenyldodecyl)-resorcinol [8], 2,4-dihydroxy-6-(10'-phenyldecyl)-acetophenone [9], 2-hydroxy-6-(12'-phenyldodecyl)-benzoic acid [10], formononetin, biochanin A, and 8-O-methylretusin, have been isolated from the stem bark of Knema glomerata. Brine shrimp lethality was used for the activity-directed chromatographic fractionations. All of these compounds showed moderate but significant toxicities to three human tumor cell lines and inhibited the growth of crown gall tumors on discs of potato tubers.

Acetophenones↗
PubMed1997

Enhancement of the biodegradability of model wastewater containing recalcitrant or inhibitory chemical compounds by photocatalytic pre-oxidation.

m-Dinitrobenzene, diphenylamine and resorcinol, three aromatic compounds found inhibitory or recalcitrant to biological treatments, were chosen as model chemicals for this study on the integration of photocatalytic-biological treatments. The degradation of each of these compounds was achieved by ultraviolet photocatalytic oxidation, leading to the formation of intermediate compounds. The photocatalytic treatment was performed in a TiO2 slurry reactor containing an aqueous solution of one of the three chemicals. The biodegradability of model wastewater treated photocatalytically was measured in terms of BOD1/TOC. Intermediate compounds that appeared at early stages of the photocatalytic degradation of m-dinitrobenzene or diphenylamine seemed to be more inhibitory than the parent compounds but this was not the case for resorcinol. A substantial improvement in BOD1/TOC could be achieved, but it required the mineralization of at least 80% of the organic carbon originally in the water. Microtox toxicity results confirmed the BOD1/TOC trends for diphenylamine.

Biodegradation, Environmental↗
PubMed2002

Comparison of the topical haemostatic agents for the prevention of suture hole bleeding. An experimental study.

OBJECTIVE: using a rabbit vascular graft model we investigated the use of fibrin glue (FG), gelatin-resorcinol-formaldehyde (GRF), and collagen (C) as a means of reducing suture hole bleeding. MATERIALS AND METHODS: twenty-eight rabbits were divided into four groups: fibrin glue, gelatin-resorcinol-formaldehyde, collagen and control. A 1 cm incision was made in the abdominal aortic wall of each animal. Incisions were covered with a polytetrafluoroethylene patch sutured with a 7-0 polypropylene. Fibrin Glue, GRF, and C were applied to cover suture holes in the groups 1, 2 and 3, respectively, but nothing in controls (group 4). The fibrin clot was allowed to achieve strength for 3 minutes before the clamps were reopened. After reopening the clamps, blood was collected from the surgical site using a syringe for a total of 2 min. RESULTS: mean blood loss was significantly lower in the FG, GRF, and C compared with control group (p=0.0022, p=0.0022, and p=0.0017, respectively). The volume of blood lost and the time of haemostasis in the group 1 (FG) was less than those in groups 2 and 3 (GRF and C, respectively) (p=0.001). The haemostasis (defined 2 min later) was achieved only in group 1 (FG) (p=0.00067). CONCLUSIONS: FG, GRF and C all reduce blood loss. Fibrin glue containing factor XIII was the most effective.

Administration, Topical↗
PubMed1990

Early proliferative responses of forestomach and glandular stomach of rats treated with five different phenolic antioxidants.

The effects of 8 weeks of oral administration of five different phenolic antioxidants, e.g. catechol (CC), resorcinol, hydroquinone (HQ), 2-tert-butyl-4-methylphenol (TBMP) and propylparabene (PP), on forestomach and glandular stomach epithelium of male F344 rats were evaluated using a combined immunohistochemical and histopathological approach. Treatment with CC and TBMP induced a significant elevation of DNA synthesis in the forestomach epithelium, associated with hyperplasia. CC administration also brought about an increase of DNA synthesis in the pyloric gland mucosa, cell proliferation in this case being reflected by an increment in the crypt height. In addition to causing an increase in the pepsinogen-isozyme-1-altered pyloric glands (PAPG), which are considered to be putative preneoplastic precursor lesions in the rat glandular stomach, CC treatment was associated with submucosal growth of pyloric mucosal cells tending to decreased pepsinogen isoenzyme 1 binding. However, DNA synthesis values in these latter areas were lower than in pyloric glands of the control group. In contrast, other phenolic compounds, resorcinol, HQ and PP, did not induce any changes in the stomach mucosa. The present results demonstrated strong proliferative responses in the stomach epithelium for CC and TBMP, indicative of promoting potential in both cases, and suggest that CC and TBMP may exert detrimental effects leading to promotion of stomach carcinogenesis or cancer development via an early proliferative response.

Animals↗
PubMed2006

Unconsumed precursors and couplers after formation of oxidative hair dyes.

Contact allergy to hair dye ingredients, especially precursors and couplers, is a well-known entity among consumers having hair colouring done at home or at a hairdresser. The aim of the present investigation was to estimate consumer exposure to some selected precursors (p-phenylenediamine, toluene-2,5-diamine) and couplers (3-aminophenol, 4-aminophenol, resorcinol) of oxidative hair dyes during and after hair dyeing. Concentrations of unconsumed precursors and couplers in 8 hair dye formulations for non-professional use were investigated, under the conditions reflecting hair dyeing. Oxidative hair dye formation in the absence of hair was investigated using 6 products, and 2 products were used for experimental hair dyeing. In both presence and absence of hair, significant amounts of unconsumed precursors and couplers remained in the hair dye formulations after final colour development. Thus, up to 1.1% p-phenylenediamine (PPD), 0.04% toluene-2,5-diamine, 0.02% 3-aminophenol and 0.02% resorcinol were found in the hair dye formulation after the required colour was developed. The consumers are thus exposed to precursors and couplers of oxidative hair dyes, both during and after hair dyeing, when the hair is washed. Furthermore, the consumers are also expected to be exposed to intermediates of oxidative hair dyes. The allergenic potential of oxidative hair dyes as well as the intermediates of these remains unknown.

Adult↗
PubMed1990

Structure-activity relations in promotion of rat urinary bladder carcinogenesis by phenolic antioxidants.

The urinary bladder tumor-promoting potentials of the phenolic antioxidants, 2-tert-butyl-4-methylphenol (TBMP), propylparaben, catechol, resorcinol and hydroquinone, which are structurally related to butylated hydroxyanisole (BHA), were investigated in 170 male F344 rats. The animals were initially given 0.05% N-butyl-N-(4-hydroxybutyl)nitrosamine (BBN) as an initiator in their drinking water for 4 weeks. Three days later, groups of 20 rats received diet containing 1.0% TBMP, 3% propylparaben, 0.8% catechol, 0.8% resorcinol, 0.8% hydroquinone or basal diet alone until the end of week 36. Significant increases in the incidences and average numbers of the putative preneoplastic lesions, papillary or nodular (PN) hyperplasia, and papillomas of the urinary bladder were only observed in the group given TBMP after BBN. Development of these lesions was not enhanced by diet containing the other test compounds and no induction was associated with any of the test chemicals alone. The results thus clearly showed that TBMP, which most closely resembles BHA, promoted urinary bladder carcinogenesis. The similar effects of TBMP and BHA on urinary bladder carcinogenesis suggest a direct link between chemical structure and biological potency.

Animals↗
PubMed1989

A simple spot test for the detection of fructose deficiency in semen.

The concentration of fructose in seminal plasma is an important variable that should be measured in the assessment of fertility status. The current method requires the boiling of diluted seminal plasma with resorcinol. The present study offers a new two-point spot test which uses the metol method. The results of analysis of 104 seminal plasma samples are in excellent correlation with the resorcinol method. The reported method is easy to use, inexpensive, and can be introduced into any laboratory.

Aminophenols↗
PubMed1981

Fluorescence spectroscopic analysis of the hydrogen bonding properties of catecholamines, resorcinolamines, and related compounds with phosphate and other anionic species in aqueous solution.

Fluorescence spectroscopic analysis based upon the difference in fluorescent behaviour of several phenol, catechol and resorcinol derivatives in 0.2 M phosphate and water, at different pH values ranging from 7.4 to 1.0, produced evidence for the existence of complexes between phosphate anions and these compounds. This complex formation was also found with acetate, citrate and glutamate but not with sulphate and borate. A comparison of different ligand structures revealed that the complex formation observed with unsubstituted phenol, catechol or resorcinol was not influenced by ethyl substitution; however, ethylamine or ethanolamine substitution favoured the formation of the complex. The findings indicate the formation of 1:1 intermolecular complexes between mono- and dihydroxyphenethylamines and several anionic species with participation of two hydrogen bonds. The predictions of a theoretical model describing this interaction are confirmed by the experimental data. Association constants of isoprenaline with phosphate and glutamate were found to be 5.1 and 26.6 litres mol-1 respectively; for the complexes of m-tyramine and terbutaline with phosphate, association constants of 15.3 and 6.9 litres mol-1 respectively, were obtained.

Catecholamines↗
PubMed1986

Degradation of orcinol by Aspergillus niger.

Aspergillus niger could utilize orcinol (5-methyl-resorcinol or 3,5-dihydroxytoluene) as the sole source of carbon and energy. In the first step of catabolism A. niger hydroxylates orcinol to form 2,3,5-trihydroxytoluene. Its oxidized form, 2-hydroxy-6-methyl-1,4-benzoquinone, was also formed in the culture medium during growth of this organism. Orcinol-grown cells showed a net increase in the intracellular acetate pool, compared with glucose-grown cells. Cell-free extracts of orcinol-grown cells showed higher activity of orcinol hydroxylase, catechol 1,2-oxygenase, and isocitrate lyase than that of glucose-grown cells. Both orcinol-grown and resorcinol-grown cells exhibit similar respiratory activity on all the substrates checked.

Aspergillus niger↗
PubMed1997

Visualization of root caries lesions by means of a diazonium dye.

A diazonium dye was used to visualize caries lesions in root tissue. Root caries lesions were created in vitro according to a variety of protocols based on methylcellulose gel (6% w/v) and/or lactic acid buffer (0.05 M, pH 4.5). Teeth containing lesions were soaked overnight in an alkaline solution of 2% (w/v) 2-naphthol or resorcinol, rinsed with distilled water, and immersed in a diazonium solution (prepared by titration of aniline with sodium nitrite in 1 M HCl at 5 degrees C) for up to 10 min, prior to being thoroughly rinsed with distilled water. The area of the caries lesion on the anatomical surface was clearly marked with a red/orange color following 5 minutes' incubation in the diazonium solution. The diazonium complex formed with 2-naphthol was found to be more resistant to leaching during rinsing and sectioning than that formed with resorcinol. Microscopic examination of sections taken in the apicalcoronal plane showed that the depth of area of the lesion was also marked by the red/orange coloration. Chemical changes in root mineral monitored during lesion formation showed some degree of correlation between lesion area and mineral dissolution. Visualization of coronal caries by this technique is currently under investigation. The visualization technique provides a simple means of determining the extent and severity of root caries lesions and may be a useful first step in their classification.

Calcium↗
PubMed1996

Methemoglobinemia induced by an over-the-counter medication.

OBJECTIVE: To report a case of methemoglobinemia induced by benzocaine and resorcinol (Vagisil) cream, an over-the-counter medication that was used to treat diaper rash in a neonate. CASE REPORT: A 6-day-old, 3350-g white boy was found to be cyanotic with blue mucous membranes on presentation. He had a diaper rash that was red and irritated, which his mother had treated with Vagisil cream. Methemoglobinemia secondary to absorption of benzocaine and resorcinol (1,3-benzenediol) from the Vagisil was diagnosed, with a methemoglobin level of 35% on admission (normal 0.4-1.5). Intravenous methylene blue 3 mg (1 mg/kg) was given; the neonate's skin color returned to normal 45 minutes after the dose. DISCUSSION: Methemoglobinemia is a condition in which hemoglobin is oxidized to the ferric form. Oxidized hemoglobin, methemoglobin, is incapable of reversibly binding oxygen at the physiologic partial oxygen pressure. Main causes of methemoglobin formation are exposure to certain oxidizing agents and drugs, deficiency of one of the enzymes necessary for reduction of methemoglobin to hemoglobin, or the presence of an abnormal hemoglobin resistant to reduction. Clinical manifestations of methemoglobinemia include diffuse slate-gray cyanosis with low oxygen saturation in the absence of respiratory distress. A single intravenous dose of methylene blue 1-2 mg/kg is the treatment of choice. CONCLUSIONS: Newborn infants are at increased risk for methemoglobinemia due to diminished enzyme systems required to reduce ferrihemoglobin to ferrohemoglobin, as well as because fetal hemoglobin is more easily oxidized than is adult hemoglobin. It is important to recognize possible drug reactions and educate parents on the potential risks of treatment with over-the-counter medications, especially in neonates.

Adult↗
PubMedDate not supplied

Alkylresorcinols in fruit pulp and leaves of Ginkgo biloba L.

These studies were undertaken to characterise resorcinolic lipids (5-n-alk(en)ylresorcinols) composition and to determine their seasonal fluctuations in fruit pulp and leaves of Ginkgo biloba L. Resorcinolic lipid concentrations were consistently higher in fruit pulp than in leaves. In pulp, several mono- and di-unsaturated homologs of alkylresorcinols were the predominant group of analysed lipids. Contrary to the fruit pulp, only 5-n-pentadecylresorcinol was demonstrated in leaves. Initially, the alkylresorcinol's content both in pulp and leaves increased until June-July and decreased following seeds ripening. This trend continued until senescence of leaves in late September and October.

Chromatography, Thin Layer↗
PubMedDate not supplied

Alkyl- and alkenylresorcinols of wheat grains and their chemotaxonomic significance.

Resorcinolic lipid contents and homologue compositions in extracts isolated from soft winter, soft spring and hard (durum) wheat grains were evaluated by both instrumental and chromatography means. Resorcinol concentrations determined in wheat were diverse and varied in samples harvested within two consecutive vegetative years, whereas their homologue profiles were found to be rather invariable. The predominant alkylresorcinols identified in wheat grains were saturated 1,3-dihydroxy-5-n-heneicosylbenzene and 1,3-dihydroxy-5-n-nonadecylbenzene. 1,3-Dihydroxy-5-n-heptadecylbenzene and 1,3-dihydroxy-5-n-tricosylbenzene were also determined, whereas 1,3-dihydroxy-5-n-pentadecylbenzene and 1,3-dihydroxy-5-n-pentacosylbenzene were present in these extracts only in spurious amounts. Furthermore, our results show that alk(en)ylresorcinols may be useful as chemotaxonomic markers for a distinction between soft and hard wheat plants. Cluster analysis with Ward's amalgamation algorithm and five different distance linkage types clearly discriminated particular wheats into species- and cultivar-specific clusters, whereas the use of principal component analysis allowed us to specify, which of the variables analysed were decisive. This approach may be useful for both plant breeders and taxonomists to classify wheat species/cultivars.

Phylogeny↗
PubMed2001

Exogenous ochronosis. An update on clinical features, causative agents and treatment options.

Exogenous ochronosis is clinically and histologically similar to its endogenous counterpart; however, it exhibits no systemic effects and is not an inherited disorder. It is characterized by an asymptomatic hyperpigmentation of the face, sides and back of the neck, back, and extensor surfaces of the extremities. The associated ochronotic discoloration most commonly results from use of products containing hydroquinone. It also occurs following use of antimalarials and products containing resorcinol, phenol, mercury or picric acid. The etiology of hydroquinone-induced hyperpigmentation in exogenous ochronosis remains speculative. The majority of patients with this condition are Black, but it has been reported to occur in Hispanics and Caucasians. Exogenous ochronosis is prevalent among South African Blacks, but is believed relatively uncommon within the US. The reasons for this phenomenon are not clear, but it could be a result of the use of skin care products containing resorcinol in combination with hydroquinone or the use of hydroquinone in a hydroalcoholic lotion. Treatment of this condition is difficult. The offending agent must be avoided, but improvement occurs only slowly. A number of topical agents have been studied as have dermabrasion and the use of lasers. Controlled studies in larger numbers of patients are require to determine the true efficacy of newer treatments.

Adrenal Cortex Hormones↗
PubMedDate not supplied

The effect of pH on the decomposition of hydrophenols in aqueous solutions by ultraviolet direct photolysis and the ultraviolet-hydrogen peroxide process.

The decomposition of catechol (o-hydrophenol) and resorcinol (m-hydrophenol) in aqueous solution by 254-nm UV direct photolysis and the UV-hydrogen peroxide (H2O2) process under various solution pH values was studied. The light absorbance and photolytic properties of catechol and resorcinol were found to be highly dependent on solution pH and can be adequately described with a three-species distribution model. For the UV-H2O2 process, the individual contribution to the decomposition of pollutants by direct photolysis and indirect hydroxyl radical destruction was differentiated by studying the linear addition of UV light absorbance of various reactant species. The contribution to the decomposition of the two hydrophenols by hydroxyl radical destruction was more than 95% in acidic and neural solutions for treatment with the UV-H2O2 process.

Catechols↗
PubMed2001

Contact allergy to balsam of Peru. II. Patch test results in 102 patients with selected balsam of Peru constituents.

BACKGROUND: In Switzerland, Germany, and Austria, allergic reactions to balsam of Peru (BP) have now made it the third most common contact allergen. OBJECTIVE: A series of 20 single BP constituents (including resorcinol monobenzoate), established in 1995, was used for patch tests in patients with a positive reaction to BP in the standard series. MATERIALS AND METHODS: Between 1995 and 1998, 2,273 patients were tested with the standard series, including BP, fragrance mix (FM), and propolis. Patients positive for BP were requested to participate in a further test using the 19 compounds of the BP constituents and resorcin monobenzoate (BP series); 102 patients agreed and were patch tested. The results of the 72-hour reading were used for the evaluation. RESULTS: A total of 93 patients reacted to 1 or more of the BP series compounds. Positive reactions were seen, in decreasing order, to cinnamic alcohol, cinnamic acid, coniferyl benzoate, benzoic acid, cinnamyl cinnamate, eugenol, resorcinol monobenzoate, coniferyl alcohol, and benzyl alcohol. There were no positive reactions to vanillin or ferulic acid. A correlation between skin lesions and frequent consumption of sweets was found in 7 patients with major positive test reactions to coniferyl benzoate and benzyl alcohol. Most of the reactions to eugenol and isoeugenol had less to do with BP itself than with a primary sensitization to fragrances. Although resorcin monobenzoate (RMB) has up to now not been detected in BP, 16 patients reacted distinctly to this compound. Eleven were strong smokers; the remaining ones had contact with plastic materials that have been reported to contain RMB. RMB is used frequently as an antioxidant in synthetic material. When these patients stopped smoking, the skin lesions cleared. However, consumption of sweets caused recurrences. CONCLUSION: The evaluation of reactions to single constituents of BP by testing with the special BP series facilitates understanding how sensitization may be acquired. The allergen may prove to be BP itself or 1 or more of its constituents. Testing for the constituents of this series may provide patients with a more specific allergen diagnosis and may facilitate improved therapy. BP may function as an important indicator for contact allergy to RMB.

Adolescent↗
PubMedDate not supplied

[The effect of anabiosis autoinducers on the bacterial genome].

The mutagenic activity of chemical analogues of microbial anabiosis autoinducers (the autoregulatory d1 factors of cell differentiation), which act to inhibit cell proliferation, to enhance cell tolerance, and to induce the transition of cells to anabiotic state, was studied using the Ames test. In the range of concentrations studied (0.1 to 100 micrograms/ml), alkyl-substituted hydroxybenzenes (AHBs) differing in hydrophobicity, i.e., methylresorcinol (C1-AHB) and hexylresorcinol (C6-AHB), as well as unsubstituted resorcinol, showed different growth-inhibiting and mutagenic effects. C6-AHB was found to inhibit the growth of Salmonella typhimurium TA100 and to induce its mutagenesis at a rate of 1.8 revertants/nmol. C1-AHB taken at low concentrations not only failed to inhibit bacterial growth but even stimulated it and exerted an antimutagenic effect. Unsubstituted resorcinol virtually did not influence bacterial growth and showed weak mutagenic activity. The growth-inhibiting effect of elevated C6-AHB concentrations correlated with the degree of the transition of the original phenotype producing S-type colonies to a phenotype producing R-type colonies. The role of AHB homologues, as microbial autoregulators with mutagenic activity, in the regulation and correlation of two processes (the phenotypic dissociation of microbial populations and the formation of resting microbial forms) is discussed. The accumulation of AHBs in senescent microbial cultures may induce adaptive mutations, change the expression of genes, and promote the development of minor cell subpopulations (phenotypes), thus providing for the adaptation of these cultures to varying environmental conditions.

Dose-Response Relationship, Drug↗
PubMed2000

[Study on biodegradation of phenols in river water].

This study on the biodegradation of phenols (phenol, o-methylphenol, o-chlorophenol and resorcinol) in river water was conducted by changing the main influential factors respectively. The results of experiment showed the phenols were greatly degradated in mild temperature, neutral pH and plenty of oxygen and the rank of the phenols biodegradation from great to small was resorcinol, phenol, o-methylphenol and o-chlorophenol. Presented in this paper is also a discussion on the biodegradation mechanism of phenols.

Biodegradation, Environmental↗