[Gallic acid, pyrogallol and pyrocatechol in the roots of Byrsonima intermedia Ad. Jussieu, form Latifolia grisebach].
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Catechols↗
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[Protective effect of propyl gallic acid on the swelling and lipid peroxidation of rat liver mitochondria].
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Animals↗
Separation and detection of gallic acid and its alkyl esters by polyamide thin-layer chromatography.
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Amides↗
Some polyphenols inhibit the formation of pentyl radical and octanoic acid radical in the reaction mixture of linoleic acid hydroperoxide with ferrous ions.
Effects of some polyphenols and their related compounds (chlorogenic acid, caffeic acid, quinic acid, ferulic acid, gallic acid, D-(+)-catechin, D-(-)-catechin, 4-hydroxy-3-methoxybenzoic acid, salicylic acid, L-dopa, dopamine, L-adrenaline, L-noradrenaline, o-dihydroxybenzene, m-dihydroxybenzene, and p-dihydroxybenzene) on the formation of 13-hydroperoxide octadecadienoic (13-HPODE) acid-derived radicals (pentyl radical and octanoic acid radical) were examined. The ESR spin trapping showed that chlorogenic acid, caffeic acid, gallic acid, D-(+)-catechin, D-(-)-catechin, L-dopa, dopamine, L-adrenaline, L-noradrenaline, and o-dihydroxybenzene inhibited the overall formation of 13-HPODE acid-derived radicals in the reaction mixture of 13-HPODE with ferrous ions. The ESR peak heights of alpha-(4-pyridyl-1-oxide)-N-tert-butylnitrone (4-POBN)/13-HPODE-derived radical adducts decreased to 46+/-4% (chlorogenic acid), 54+/-2% (caffeic acid), 49+/-2% (gallic acid), 55+/-1% [D-(+)-catechin], 60+/-3% [D-(-)-catechin], 42+/-1% (L-dopa), 30+/-2% (dopamine), 49+/-2% (L-adrenaline), 24+/-2% (L-noradrenaline), and 54+/-5% (o-dihydroxybenzene) of the control, respectively. The high performance liquid chromatography-electron spin resonance (HPLC-ESR) and high performance liquid chromatography-electron spin resonance-mass spectrometries (HPLC-ESR-MS) showed that caffeic acid inhibited the formation of octanoic acid radical and pentyl radical to 42+/-2% and 52+/-7% of the control, respectively. On the other hand, the polyphenols and their related compounds had few inhibitory effects on the radical formation in the presence of EDTA. Visible absorbance measurement revealed that all the polyphenols exhibiting the inhibitory effect chelate ferrous ions. Above results indicated that the chelation of ferrous ion is essential to the inhibitory effects of the polyphenols.
Chromatography, High Pressure Liquid↗
[Study on gallic acid preparation by using immobilized tannase from Aspergillus niger].
Immobilized tannase which had higher ability of transforming tannin from Chinese gallotannin into GA was prepared by embedding tannase with calcium alginate carrier. The immobilization conditions and some properties of the immobilized tannase were studied. The results showed that: The optimal immobilized parametres were 90 mg sodium alginate, 546 u(182 u/mL) tannase and 1%-2% CaCl2. The optimum temperature and pH value of immobilized tannase were 45 degrees C and 6.5, respectively. It was stable in the temperature range of 10-50 degrees C and between pH5-7. Based on the optimum program, the laboratory gramme-grade preparation experiments of GA were done. The average yield of GA product in three preparations was upto 61%, and was about equivalent to the yield of acidic hydrolytic method which is used to produce GA industrially now. Thus, the research results possessed potential applied value.
Aspergillus niger↗
Aromatic inhibitors of dehydroquinate synthase: synthesis, evaluation and implications for gallic acid biosynthesis.
The role of the active site metal in determining binding to 3-dehydroquinate synthase has been examined. Protocatechuic acid, catechol, and derivatives of these aromatics were synthesized that shared the common element of an ortho dihydroxylated benzene ring. Inhibition constants were determined for each aromatic as well as the variation of this inhibition as a function of whether Co(+2) or Zn(+2) was the active site metal ion.
Anticarcinogenic Agents↗
The sensitizing capacity of the antioxidants propyl, octyl, and dodecyl gallate and some related gallic acid esters.
8 alkyl gallates, including the widely used antioxidants propyl, octyl, and dodecyl (= lauryl) gallate, have been subjected to experimental sensitization in guinea pigs. Using a modern sensitization procedure, the results showed that all gallates are moderate to strong contact sensitizers: dodecyl (= lauryl) gallate was found to be the strongest. A characteristic correlation between side chain length and mean response was observed, giving a maximum of sensitization at a length of 12 carbon atoms (dodecyl gallate). A literature review revealed that the frequency of reports of allergic contact dermatitis from antioxidants of the gallate type has increased in the last 4 years. In most cases, the moderate sensitizer propyl gallate was the source of sensitization.
Animals↗
Differential effects of ferritin, calcium, zinc, and gallic acid on in vitro proliferation of human glioblastoma cells and normal astrocytes.
In vitro, when using low concentrations of ferritin (ng/ml) or CaCl2 (micrograms/ml), multiplication of a human, 1,3-bis-(2-chloroethyl)-1-nitrosourea (BCNU)-resistant glioblastoma cell line (U251) is enhanced 1.5 to 2 times more actively than multiplication of a normal astrocyte line (CRL 1656). Ferritin and Ca2+ ions exhibit a marked effect on DNA isolated from these cells: glioblastoma DNA relaxation is strongly increased (as evidenced by increased 260 nm ultraviolet absorbance), being from 5 to 6 times that of astrocyte DNA, which remains only slightly affected. Under identical experimental conditions, Zn2+ and gallium ions selectively inhibit glioblastoma cell multiplication but at the same concentrations do not inhibit astrocyte multiplication. Ultraviolet absorbance measurements demonstrate that both of these agents condense relaxed glioblastoma DNA in vitro. Zn2+ or gallium ions added to culture medium containing stimulatory concentrations of ferritin or Ca2+ ions selectively and strongly inhibit enhancement of glioblastoma cell multiplication by these mitogens while not affecting normal multiplication of astrocytes.
Astrocytes↗
Detection of free radicals generated from hydrogen peroxide, gallic acid and haemoprotein chemiluminescence system by electron spin resonance spectroscopy.
Low-level chemiluminescence is produced in a hydrogen peroxide (H(2)O(2))/gallic acid/haemoprotein system with single broad peaks around 520 nm, regardless of the biological role of the haemoprotein. The free haem iron systems (haemin and haematin systems) gave a higher photon intensity (1.5 x 10(4) and 2.0 x 10(4) cps) than that of the H(2)O(2)/gallic acid/haematoporphyrin system. These results indicated that haem iron plays a significant role in the photon emission of haemoprotein systems. A free radical with a g value of 2. 0058 was detected through a direct electron spin resonance (ESR) method. The photon intensity of the H(2)O(2)/gallic acid/haemoprotein system decreased in the order: HRP > cytochrome c > myoglobin > haemoglobin, and this corresponded to the decrease in radical intensity. These results indicated that the formation of the free radical with a g value of 2.0058 may be the key step for chemiluminescence in the H(2)O(2)/gallic acid/haemoprotein system. A quartet line similar to DMPO-OH adducts and uncomplexed free radicals (g = 2.0058) was detected using the ESR spin-trapping method in the H(2)O(2)/gallic acid/cytochrome c system.
Electron Spin Resonance Spectroscopy↗
Influence of gallic acid esters on drug-metabolizing enzymes of rat liver.
The effect of three antioxidants, propyl, octyl and dodecyl gallate, on hepatic drug metabolism in male rats was studied in vivo and in vitro. When fed at a dietary concentration of 1% for 14 days, only dodecyl gallate increased relative liver weight. Cytochrome P-450 content was not influenced, but a slight increase in cytochrome b5 content was observed after the feeding of propyl gallate. Monooxygenase activity (benzo[a]pyrene-hydroxylase and ethoxycoumarin-deethylase activities) was not affected by propyl or octyl gallate, but a significant decrease in benzo[a]pyrene-hydroxylase activity was apparent in rats fed dodecyl gallate. Study of benzo[a]pyrene-metabolite formation in liver microsome preparations from control and propyl gallate-treated rats showed an overall decrease in metabolite production following gallate treatment, the decrease being statistically significant for the formation of the 9,10-dihydrodiol. Epoxide-hydratase activity was enhanced by a factor of 1.5 in rats fed propyl gallate; glutathione-transferase activity was unaffected. In vitro, the gallates proved to be potent inhibitors of ethoxycoumarin deethylation in liver microsomes from untreated and phenobarbital-treated rats; however, when cytochrome P-448 had been induced by pretreatment with 3-methylcholanthrene, ethoxycoumarin deethylase was less sensitive to the inhibitory action of the gallates.
Animals↗
Effects of phenolic acids on human phenolsulfotransferases in relation to their antioxidant activity.
Sulfate conjugation by phenolsulfotransferase (PST) enzyme is an important process in the detoxification of xenobiotics and endogenous compounds. There are two forms of PST that are specific for the sulfation of small phenols (PST-P) and monoamines (PST-M). Phenoilc acids have been reported to have important biological and pharmacological properties and may have benefits to human health. In the present study, human platelets were used as a model to investigate the influence of 13 phenolic acids on human PST activity and to evaluate the relationship to their antioxidant activity. The results showed that chlorogenic acid, syringic acid, protocatechuic acid, vanillic acid, sinapic acid, and caffeic acid significantly (p < 0.05) inhibited the activities of both forms of PST by 21-30% at a concentration of 6.7 microM. The activity of PST-P was enhanced (p < 0.05) by p-hydroxybenzoic acid, gallic acid, gentisic acid, o-coumaric acid, p-coumaric acid, and m-coumaric acid at a concentration of 6.7 microM, whereas the activity of PST-M was enhanced by gentisic acid, gallic acid, p-hydroxybenzoic acid, and ferulic acid. The phenolic acids exhibited antioxidant activity as determined by the oxygen radical absorbance capacity (ORAC) assay and Trolox equivalent antioxidant capacity (TEAC) assay, especially gallic acid, p-hydroxybenzoic acid, gentisic acid, and coumaric acid, which had strong activity. The overall effect of phenolic acids tested on the activity of PST-P and PST-M was well correlated to their antioxidant activity of ORAC value (r = 0.71, p < 0.01; and r = 0.66, p < 0.01). These observations suggest that antioxidant phenolic acids might alter sulfate conjugation.
Adult↗
Is the solubilized product from the degradation of lignocellulose by actinomycetes a precursor of humic substances?
Three actinomycetes (Streptomyces sp. EC22, Streptomyces viridosporus T7A and Thermomonospora fusca BD25) were assessed for their ability to degrade ball-milled wheat straw. All gave maximum levels of solubilized lignocellulose products (APPL) at the beginning of the stationary phase of growth (72-96 h). Low-molecular-mass aromatic compounds extracted from the APPL were analysed by reverse-phase and gas chromatography. Although the number of chromatographic peaks detected made identification of the products difficult, p-coumaric acid (4-hydroxycinnamic acid), protocatechuic acid (3,4-dihydroxybenzoic acid), gallic acid (3,4,5-trihydroxybenzoic acid), gallic acid methyl ester (methyl-3,4,5-trihydroxybenzoate) and 4-methoxyphenol were recognized. The infrared spectra of the three strains were similar to the spectra of humic acids, with all APPL extracts showing carbonyl, amino, carboxyl, aliphatic and aromatic group vibrations. Also detected were peptide linkages of proteins. The results suggest a role for actinomycetes in the formation of humic substances in soils and composts.
Actinomycetales↗
A reevaluation of the peroxynitrite scavenging activity of some dietary phenolics.
Peroxynitrite is implicated in many diseases. Hence, there is considerable interest in potential therapeutic peroxynitrite scavengers. Diet-derived phenolics have been claimed to be powerful peroxynitrite scavengers. However, the reactivity of peroxynitrite can be significantly modified by bicarbonate and this has not been considered in evaluations of the scavenging activity of phenols. Bicarbonate (25 mM) significantly decreased the ability of several phenolic compounds (caffeic acid, o- and p-coumaric acid, gallic acid, ferulic acid) but not others (catechin and epicatechin) to inhibit peroxynitrite-mediated tyrosine nitration. Bicarbonate (25 mM) also decreased the ability of catechin, epicatechin, quercetin and ferulic acid but not chlorogenic acid, gallic acid, caffeic acid and o-coumaric acid to inhibit peroxynitrite-mediated alpha(1)-antiproteinase inactivation. These results show that physiological concentrations of bicarbonate substantially modify the ability of dietary phenolics to prevent peroxynitrite-mediated reactions. When assessing compounds for peroxynitrite scavenging, experiments should be conducted in the presence of bicarbonate to avoid misleading results.
Bicarbonates↗
Chorda tympani and lingual nerve responses to astringent compounds in rodents.
A wide variety of compounds in foods and beverages produce astringent sensations when introduced into the oral cavity. There is controversy, however, whether "astringency," with its associated puckering and drying sensations, is a fundamental taste quality or is a tactile sensation. To address this issue, electrophysiological recordings were made from the gerbil chorda tympani nerve and the rat lingual nerve. The chorda tympani nerve transmits taste information from the anterior 2/3 of the tongue, whereas the lingual nerve transmits tactile, thermal and pain sensations from the anterior 2/3 of the tongue. The astringent compounds tested were: tannic acid, tartaric acid, gallic acid, aluminum ammonium sulfate and aluminum potassium sulfate. Tannic acid, tartaric acid, and gallic acids were tested at concentrations up to 120 mM over a pH range from approximately 2 to 6. The aluminum salts were tested at concentrations up to 160 mM only at low pH's. All compounds rapidly (and at lower concentrations, reversibly) stimulate the chorda tympani nerve in a concentration-dependent manner at all pH's tested. The rapidity and reversibility of the chorda tympani responses suggest that astringent-tasting compounds interact directly with taste cells rather than indirectly by precipitating salivary proteins. At pH 6, tannic acid, tartaric acid, and gallic acid all elicit robust chorda tympani responses, implying that the ionized forms of these compounds produce taste sensations. None of these compounds stimulate lingual nerves over the same concentration and pH ranges used in the chorda tympani experiments.(ABSTRACT TRUNCATED AT 250 WORDS)
Animals↗
Antioxidant activities of phenolic acids on ultraviolet radiation-induced erythrocyte and low density lipoprotein oxidation.
The exposure of mammalian cells to UV light induces various deleterious responses. Some of the major harmful effects are DNA damage, cell membrane peroxidation, systemic immune suppression, and aging acceleration. Reactive oxygen species and free radicals are believed to be largely responsible for some of the deleterious effects of UV upon cells. Typical administration of antioxidants has recently proved to represent a successful strategy for protecting the cells against UV-mediated oxidative damage. The objective of this study was to investigate the inhibitory effect of phenolic acids (caffeic acid, ferulic acid, gallic acid, and protocatechuic acid) on oxidative damage in human erythrocytes and low-density lipoprotein (LDL) induced by UVB radiation. The results revealed that the thiobarbituric acids reactive substances induced by UVB were decreased from 2.78 to 0.12-0.89 nmol MDA/mg protein in erythrocyte ghost and from 0.72 to 0.14-0.43 nmol MDA/mg protein in LDL by the addition of phenolic acids (100 muM). Caffeic acid, ferulic acid, and gallic acid exhibited over 85 and 60% inhibitory effect toward UVB-induced oxidation in erythrocytes and LDL, respectively. Phenolic acids, especially gallic acid, could maintain the normal glutathione levels and glutathione peroxidase activity in hemolysate from erythrocytes that were exposed to UVB radiation in comparison with untreated control. The results indicate that the antioxidant activities of caffeic acid and ferulic acid play a potential role in protection against UVB oxidative damage to human erythrocytes and LDL.
Antioxidants↗
Characterization and purification of polyphenol oxidase from artichoke (Cynara scolymus L.).
In this study, the polyphenol oxidase (PPO) of artichoke (Cynara scolymus L.) was first purified by a combination of (NH(4))(2)SO(4) precipitation, dialysis, and a Sepharose 4B-L-tyrosine-p-aminobenzoic acid affinity column. At the end of purification, 43-fold purification was achieved. The purified enzyme migrated as a single band on sodium dodecyl sulfate-polyacrylamide gel electrophoresis. Polyacrylamide gel electrophoresis indicated that PPO had a 57 kDa molecular mass. Second, the contents of total phenolic and protein of artichoke head extracts were determined. The total phenolic content of artichoke head was determined spectrophotometrically according to the Folin-Ciocalteu procedure and was found to be 425 mg 100 g(-1) on a fresh weight basis. Protein content was determined according to Bradford method. Third, the effects of substrate specificity, pH, temperature, and heat inactivation were investigated on the activity of PPO purified from artichoke. The enzyme showed activity to 4-methylcatechol, pyrogallol, catechol, and L-dopa. No activity was detected toward L-tyrosine, resorsinol, and p-cresol. According to V(max)/K(m) values, 4-methylcatechol (1393 EU min(-1) mM(-1)) was the best substrate, followed by pyrogallol (1220 EU min(-1) mM(-1)), catechol (697 EU min(-1) mM(-1)), and L-dopa (102 EU min(-1) mM(-1)). The optimum pH values for PPO were 5.0, 8.0, and 7.0 using 4-methylcatechol, pyrogallol, and catechol as substrate, respectively. It was found that optimum temperatures were dependent on the substrates studied. The enzyme activity decreased due to heat denaturation of the enzyme with increasing temperature and inactivation time for 4-methylcatechol and pyrogallol substrates. However, all inactivation experiments for catechol showed that the activity of artichoke PPO increased with mild heating, reached a maximum, and then decreased with time. Finally, inhibition of artichoke PPO was investigated with inhibitors such as L-cysteine, EDTA, ascorbic acid, gallic acid, d,L-dithiothreitol, tropolone, glutathione, sodium azide, benzoic acid, salicylic acid, and 4-aminobenzoic acid using 4-methylcatechol, pyrogallol, and catechol as substrate. The presence of EDTA, 4-aminobenzoic acid, salicylic acid, gallic acid, and benzoic acid did not cause the inhibition of artichoke PPO. A competitive-type inhibition was obtained with sodium azide, L-cysteine, and d,L-dithiothreitol inhibitors using 4-methylcatechol as substrate; with L-cysteine, tropolone, d,L-dithiothreitol, ascorbic acid, and sodium azide inhibitors using pyrogallol as substrate; and with L-cysteine, tropolone, d,L-dithiotreitol, and ascorbic acid inhibitors using catechol as a substrate. A mixed-type inhibition was obtained with glutathione inhibitor using 4-methylcatechol as a substrate. A noncompetitive inhibition was obtained with tropolone and ascorbic acid inhibitors using 4-methylcatechol as substrate, with glutathione inhibitor using pyrogallol as substrate, and with glutathione and sodium azide inhibitors using catechol as substrate. From these results, it can be said that the most effective inhibitor for artichoke PPO is tropolone. Furthermore, it was found that the type of inhibition depended on the origin of the PPO studied and also on the substrate used.
Catechol Oxidase↗
Inhibition of protease activities of periodontopathic bacteria by extracts of plants used in Kenya as chewing sticks (mswaki).
Extracts from five plants used as chewing sticks, and tannic acid, gallic acid and methyl ester of gallic acid, were tested for their ability to inhibit proteolytic activities of three strains of Bacteroides gingivalis, three strains of Bacteroides intermedius and two strains of Treponema denticola. Aqueous extract from the plants Rhus natalensis and Euclea divinorum were the most inhibitory of those tested, inhibiting by 50% the proteolytic activity of the test organisms, at concentrations of up to 200 micrograms/ml. Tannic and gallic acids had similar effects at concentrations of less than 10 micrograms/ml, while the methyl ester of gallic acid was less inhibitory. These findings suggest that extracts from plants used as chewing sticks may possess enough inhibitory components to interfere with the virulence and growth of periodontopathic bacteria in vivo, provided they are able to gain access to the subgingival sites such bacteria preferentially inhabit.
Bacteroides↗
Inhibitory effect of phenolic acids on the proliferation of 3T3-L1 preadipocytes in relation to their antioxidant activity.
Obesity is an important topic in the world of public health and preventive medicine. Inhibition of preadipocyte proliferation plays an important role in the mechanisms of proposed antiobesity. In this in vitro study, the inhibitory effect of phenolic acids on 3T3-L1 preadipocytes was evaluated, and a relationship analysis was then conducted. The results showed that the addition of phenolic acids to the growth medium decreased the cell population growth of 3T3-L1 preadipocytes. The IC50 values of chlorogenic acid, gallic acid, o-coumaric acid and m-coumaric acid on 3T3-L1 preadipocytes were 72.3, 43.3, 48.2, and 49.2 microM, respectively. A relationship analysis indicated that there is a significant linear correlation between the influence of phenolic acids on cell population growth and their antioxidant activity (r = 0.77, p < 0.01). The cell cycle assay indicated that the treatment of 3T3-L1 preadipocytes with chlorogenic acid, o-coumaric acid, and m-coumaric acid caused cell cycle arrest in the G1 phase. Gallic acid did not affect the cell cycle profile; however, it increased the number of apoptotic cells (sub-G1 phase) in a time- and dose-dependent manner. Annexin V-fluorescein isothiocyanate (FITC)-propidium iodide (PI) apoptosis flow cytometric assay showed that gallic acid increased the number of early apoptotic (annexin V-FITC+/PI-) and late apoptotic cells (annexin V-FITC+/PI+) but not necrotic cells (annexin V-FITC-/PI+). The treatment of cells with gallic acid caused the loss of mitochondrial membrane potential (delta psi(m)). These results indicate that the inhibition of preadipocyte population growth by some phenolic acids might have further implication in in vivo antiobesity effects.
3T3-L1 Cells↗