Search PubMed⌕ Search

SEARCH · Search PubMed

Results for “GALLIC ACID”

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.

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
PubMed2004

Characterization of phenolic compounds in some Indian mango cultivars.

Mangoes (Mangifera indica) are rich in phenolic acids as detected by high-performance liquid chromatography. The phenolics have prominent medicinal properties. Among six important commercial mango cultivars (Deshi, Langra, Chausa, Mallika, Dashahari and Amrapali) tannic acid was maximal in Mallika, while gallic acid was maximal in Chausa and all other varieties. Caffeic acid was maximal in Langra followed by Chausa and Amrapali. Many of the pharmacological properties attributed to mango might be due to the presence of phenolic acids in fairly significant amounts.

Caffeic Acids↗
PubMed1999

[Studies on chemical constituents in the fruit of Canarium album Raeusch].

OBJECTIVE: To study the chemical constituents in the fruit of Canarium album. METHOD: Compounds were isolated by chromatography and elucidated on the basis of spectroscopic analysis. RESULT: The compounds obtained were determined as scoparone, scopoletin, (E)-3,3'-dihydroxy-4,4'-dimethoxystilbene and gallic acid. CONCLUSION: All the compounds, except gallic acid, were obtained from this plant for the first time.

Burseraceae↗
PubMed2001

Analysis of phenolic constituents of biological interest in red wines by high-performance liquid chromatography.

We describe a reversed-phase HPLC method that uses gradient elution and diode array detection to determine four biologically active phenolic constituents of red wines: gallic acid, trans-resveratrol, quercetin and rutin. The method permits direct injection without sample pre-treatment. ODS Hypersil served as the stationary phase; the gradient was formed by acetic acid, methanol, and water. Each analysis required an equilibration period of 10 min and a run time of 50 min for completion. Previously, total phenols were analysed according to the Folin-Ciocalteu method, using gallic acid as the standard, and the results are given as gallic acid equivalent.

Calibration↗
PubMed2002

Investigation of the release of iron from ferritin by naturally occurring antioxidants.

Ferritin is the main intracellular iron storage protein. The release of iron from ferritin in the presence of a number of phenolic based compounds of nutritional significance was studied at physiological pH. The release of iron was measured by monitoring the formation of the iron(II)-ferrozine complex. The kinetics of this process were studied in Hepes buffer (pH 7.00), at 37 degrees C. The order of ability to remove iron from ferritin is epigallocatechin>gallic acid methyl ester approximately equal to sinapic acid>ferulic acid. The presence of the oxyradical scavenger urea resulted in a slight inhibition in the release of iron from ferritin by both gallic acid methyl ester and epigallocatechin. The ability of each reagent to release iron is interpreted on the basis of their ability to (a) reduce the bound iron and (b) complex the iron with the oxidised form of the phenol, thus mobilising it from the protein. These studies indicate that some phenolic based compounds that have been epidemiologically associated with a negative effect on iron absorption in man, can individually mobilise and release iron from ferritin under suitable conditions.

Animals↗
PubMed1998

Tannin-tolerant ruminal bacteria from East African ruminants.

Three strains of tannin-tolerant rumen bacteria were isolated from enrichment cultures of rumen microflora of sheep, goat, and antelope and established in medium containing high concentrations of crude tannin extract or tannic acid. These three strains (EAT2, ES3, and EG19), characterized as Selenomonas species, were curved rods, obligately anaerobic, Gram negative, highly motile, and grew in media containing 50 g of tannin extract/L and 50-70 g of tannic acid/L. Strain EAT2 was able to hydrolyze gallic acid, while strains ES3 and EG19 hydrolyzed tannic acid but not gallic acid. All isolates were able to grow in media containing up to 8 g of condensed tannins/L. Growth was very slow when soluble carbohydrate was not added to the medium.

Anaerobiosis↗
PubMed1976

Galloylglucoses of low molecular weight as mordant in electron microscopy. II. The moiety and functional groups possibly involved in the mordanting effect.

Synthetic pentamonogalloylglucose applied to fixed tissues acts as a mordant, inducing high and diversified contrast similar to that obtained with natural gallotannins of low molecular weight (LMGG). By the separate use of each of the two moieties of the galloylglucose molecule, it was found that gallic acid is the mordanting agent. Glucose may contribute, however, to the effect by increasing the solubility and cross-linking potential of the compound, since the mordanting induced by gallic acid alone is weaker than that produced by its hexose esters. As suggested by results obtained with various phenolics and benzoic acid derivatives, the functional groups required for the mordanting effect of such agents are the carboxyl group, and at least one hydroxyl group concomitantly present on the benzene ring. In the case of galloylglucoses, it is assumed that the effect is due to hydrolysis products (gallic, digallic, or trigallic acids) or to the multiple hydroxyl groups of the intact molecule. Esters of gallic acid (propyl- and methylgallate), as well as pyrogallol, produce a "reversed staining" of all membranes, except for those of communicating (gap) junctions.

Cytological Techniques↗
PubMed2005

Effects of non-ionic surfactants on isotachophoretic separations of 2-arylpropionic acids.

Non-ionic surfactant (Brij 35, Tween 20, Tween 80 and Tergitol NPX) modified capillary isotachophoresis was investigated for the separation of 2-arylpropionic acids (fenoprofen, flurbiprofen, ibuprofen, ketoprofen and naproxen) and benzoic acid and its derivatives (salicylic, acetylsalicylic and gallic acids). The relative step height (RSH) values of analytes were found to be dependent on the type and concentration of the surfactant. The strength of the affinity of the 2-arylpropionic acids to the non-ionic micelles was found to be as follows: flurbiprofen > fenoprofen > ibuprofen > naproxen > ketoprofen. In general, the RSH values of 2-arylpropionic acids increase with an increase in the concentration of surfactants. However, the RSHs of benzoic, salicylic and gallic acids are not considerably affected. Separation of all acids was obtained with the Tween 20 (1.5%, w/v) in the leading electrolyte 10 mmol L(-1) hydrochloric acid/L-histidine (pH 6.0). Changes in the fluorescence intensity of fenoprofen, flurbiprofen and naproxen were also investigated in micellar media (Tween 20, Tween 80 and Brij 35). The strength of the affinity of the 2-arylpropionic acids to the Tweens micelles was found to be as follows: flurbiprofen > fenoprofen > naproxen, which is consistent with the isotachophoretic results. On the contrary, the strength of the affinity to the Brij micelles was found to be as follows: fenoprofen > naproxen > flurbiprofen.

Electrophoresis, Capillary↗
PubMed2006

Neuroprotective effects of green and black teas and their catechin gallate esters against beta-amyloid-induced toxicity.

Teas represent a large family of plants containing high amounts of polyphenols that may confer health benefits in various diseases. Recently, it has been hypothesized that tea consumption may also reduce the risk of age-related neurodegenerative pathologies. Considering the deleterious role of beta-amyloid (Abeta) in the aetiology of Alzheimer's disease (AD), we investigated green and black tea extracts and flavan-3-ols (present as monomers and dimers in green and black forms, respectively) against toxicity induced by Abeta-derived peptides using primary cultures of rat hippocampal cells as model. Both green and black tea extracts (5-25 microg/mL) displayed neuroprotective action against Abeta toxicity. These effects were shared by gallic acid (1-20 microm), epicatechin gallate (ECG; 1-20 microM) and epigallocatechin gallate (EGCG; 1-10 microM), the former being the most potent flavan-3-ol. In contrast, epicatechin and epigallocatechin were ineffective in the same range of concentrations. Moreover, only tea flavan-3-ol gallate esters (i.e. ECG, EGCG) and gallic acid inhibited apoptotic events induced by Abeta(25-35). Interestingly, EGCG and gallic acid inhibited Abeta aggregation and/or the formation of Abeta-derived diffusible neurotoxin ligands. Taken together, these results indicate that the catechin gallates (through the galloyl moiety) contribute to the neuroprotective effects of both green and black teas. Moreover, the protective effect of EGCG is likely to be associated, at least in part, with its inhibitory action on Abeta fibrils/oligomers formation. These data also support the hypothesis that not only green but also black teas may reduce age-related neurodegenerative diseases, such as AD.

Amyloid beta-Peptides↗
PubMed2002

Validation of a LC method for the analysis of phenolic compounds from aqueous extract of Phyllanthus niruri aerial parts.

A reversed-phase high-performance liquid chromatographic separation and quantitative method using a phosphoric acid-acetonitrile gradient was developed to analyze phenolic compounds present in aqueous extract from the aerial parts of Phyllanthus niruri. The chromatographic method was validated for linearity, precision and accuracy for both reference substance (gallic acid) and for three well resolved peaks from P. niruri aqueous extract. Both calibration curves were linear with correlation coefficients higher than 0.999. The reproducibility for the three peaks ranged from 2.3% to 4.6% and the accuracy for gallic acid in the aqueous extract was 103%. The method allowed the complete resolution of three peaks, one of them was identified by diode array detection as gallic acid. The analysis of the botanic morphological elements of the aerial parts from P. niruri showed that the leaves have a higher amount of phenolic compounds than the branches.

Chromatography, High Pressure Liquid↗
PubMed1997

Phenolic and antibacterial constituents of Vahlia capensis.

The n-butanol fraction of Vahlia capensis yielded kaempferol, quercetin, afzelin, astragalin, quercitrin, isoquercitrin, rutin, gallic acid, chiro-inositol, dulcitol, and a novel biflavonoid, VC-15B (vahlia biflavone). The compounds were identified using 1D and 2D NMR techniques and FABMS. Vahlia biflavone and gallic acid were isolated, using bioassay-guided procedure and identified as the antibacterial components. Both compounds showed activity against Gram positive Staphylococcus aureus and Bacillus subtilis. Vahlia biflavone gave MIC values of 15.3 micrograms/ml and 30.6 micrograms/ml against S. aureus and B. subtilis, respectively while gallic acid gave a value of 71.3 micrograms/ml for both organisms.

Anti-Bacterial Agents↗
PubMedDate not supplied

Effect of polyphenolic compounds on the proteolytic activities of constitutive and immuno-proteasomes.

The effect of several polyphenols on the 20S proteasomes, both the constitutive and the LMP proteasomes, isolated from bovine tissues, has been investigated. Polyphenolic compounds show many biological activities such as antiviral, antibacterial, antifungal, anti-inflammatory, antimutagenic, and antiallergic activities. However, the molecular mechanism underlying these effects has not been identified. It is well established that polyphenols possess inhibitory activities on several enzymes and among them the 20S proteasome. In the present work, the ChT-L, BrAAP, PGPH, and T-L activities of the isolated constitutive and immuno-proteasomes were assayed in order to get an overall information on the polyphenols binding to the complexes. The effects of the polyphenols on the proteasomal activities were analyzed, taking into account the different subunits composition of the two complexes. Furthermore the same activities were measured on whole extracts from cancer cells exposed to EGCG and gallic acid, evaluating, also, their antioxidant action under oxidative stress. EGCG and gallic acid are able to affect the 20S proteasomes functionality, depending on the complex subunit composition and, in cell extracts, they behave both as antioxidants and proteasome effectors.

Adenocarcinoma↗
PubMed2003

Rational optimization of a short human P-selectin-binding peptide leads to nanomolar affinity antagonists.

P-selectin plays an important role in the development of various diseases, including atherosclerosis and thrombosis. In our laboratory we recently identified a number of specific human P-selectin-binding peptides containing a Glu-Trp-Val-Asp-Val consensus motif, displaying a low micromolar affinity for P-selectin (IC(50) = 2 microm). In search of more potent antagonists for P-selectin, we have optimized the EWVDV pentapeptide core motif via a two-step combinatorial chemistry approach. A dedicated library of peptide derivatives was generated by introducing seven substituents at the N and C termini of the motif. In particular, pentapeptides with gallic acid or 1,3,5-benzenetricarboxylic acid substituents at the N terminus proved to be considerably more potent inhibitors of P-selectin binding than the parental peptide. After removal of the N-terminal glutamic acid from the core sequence, which appeared to be replaceable by a carboxamide function without loss of affinity, a second library was synthesized to map the chemical moieties within the gallic acid or 1,3,5-benzenetricarboxyl acid groups responsible for the enhanced P-selectin binding. Moreover, by varying the length and rigidity of the connective spacer, we have further optimized the spatial orientation of the N-terminal substituent. The combined use of phage display and subsequent combinatorial chemistry led to the design of a number of gallic acid- containing peptides with low nanomolar affinity for P-selectin both under static and dynamic conditions (IC(50) = 15.4 nm). These small synthetic antagonists, which are equally as potent as the natural ligand P-selectin glycoprotein ligand-1, are promising leads in anti-atherothrombotic therapy.

Amino Acid Sequence↗
PubMedDate not supplied

Chemiluminescence properties of soybean protein fraction in the hydroperoxide and hydrogen donor system.

Whey fraction, a constituent of soybean protein, produced a photon emission in the presence of gallic acid and hydrogen peroxide. Identification of the chemiluminescence agent from the whey fraction indicated the participation of lipoxygenase in the emission. The reactivity of lipoxygenase with peroxides in the gallic acid solidus hydroperoxide system was in the order of methylethyl hydroperoxide (MEK-OOH, 4800 cps) > tert-butyl hydroperoxide (tert-BuOOH, 607 cps) > hydrogen peroxide (H(2)O(2), 455 cps) > cumene hydroperoxide (cumene-OOH, 261 cps). Emission maxima for H(2)O(2) and cumene-OOH were 670 nm, and emission maxima for MEK-OOH and tert-BuOOH were at 510 nm. The photon intensity from the gallic acid lipoxygenase system corresponded to the linoleic acid hydroperoxide value. A high correlation of photon intensity with hydroperoxide, including linoleic hydroperoxide was useful as a simple and sensitive method for the direct detection of hydroperoxides in biomaterials.

Hydrogen Peroxide↗
PubMed1995

Rumen involvement in sheep tannic acid metabolism.

Tannic acid (TA) metabolism was studied in sheep after p.o., intra-abomasal and i.p. administration. TA and its phenolic metabolites in ruminal fluid, abomasal fluid, plasma and urine were determined using high-performance liquid chromatography at various intervals post-dosing. After po administration, gallic acid (GA) and pyrogallol (PYR) were present in ruminal fluid and plasma, and GA, PYR and 4-O-methyl gallic acid (40MGA) were found in urine. The concentration of GA in ruminal fluid and urine gradually decreased after dosing, while PYR concentration continued to rise. By contrast, after intra-abomasal dosing, GA and ellagic acid (EA) as well as TA were found in abomasal fluid, GA, 40MGA, EA and TA were present in plasma, and GA, 40MGA and PYR were in urine. The latter 3 metabolites were also detected in the urine after ip administration of TA. The plasma concentration of TA after intra-abomasal administration was significantly correlated with liver necrosis, and PYR concentration in ruminal fluid following po administration was significantly correlated to blood methemoglobin level. It was concluded that the methemoglobinemia seen in sheep given TA po is caused by high levels of the phenolic metabolite PYR, which is produced in the rumen. Liver and kidney necrosis, seen in sheep given TA directly into the abomasum, appears caused by unmetabolized TA rather than by metabolites.

Abomasum↗
PubMed2002

Polyphenols in red wine inhibit the proliferation and induce apoptosis of LNCaP cells.

OBJECTIVE: To assess the effect of five polyphenol constituents of red wine (quercetin, morin, rutin, gallic acid and tannic acid) on the proliferation of LNCaP cells, and to quantify the extent of apoptosis with each polyphenol. MATERIALS AND METHODS: LNCaP cells (500) were cultured in microtitre plates and treated with gallic acid, tannic acid, quercetin (1, 5 and 10 micromol/L), rutin and morin (25, 50 and 75 micromol/L). A colorimetric immunoassay was then used to determine the extent of proliferation at 24, 48, 72 and 96 h, and a cell-death detection assay to assess apoptosis at 24, 48 and 72 h. RESULTS: Gallic and tannic acid (5 and 10 micromol/L), morin (50 and 75 micromol/L), quercetin (5 and 10 micromol/L) and rutin (50 and 75 micromol/L) all significantly inhibited (P<0.05) cell proliferation compared with the control. Apoptotic indexes were significantly greater (P<0.01) in the presence of gallic (5 and 10 micromol/L) and tannic acid (5 and 10 micromol/L), and rutin (75 micromol/L, P<0.05) than in the control. The apoptotic effect of morin (75 micromol/L), although significant (P<0.01), only appeared at 72 h. Conversely, while significant (P<0.05) quercetin (5 and 10 micromol/L) had a transient (first 48 h) apoptotic effect compared with the control. CONCLUSION: Quercetin, rutin, morin, gallic acid and tannic acid inhibited the growth of LNCaP cells at different concentrations, and induced apoptosis. The results provide a strong rationale for studying the in vivo effects of these compounds.

Apoptosis↗
PubMed1985

Effect of phenolic compounds, ethyl alcohol, and sodium metabisulphite on the lytic activity of phage PL-1 on a Lactobacillus casei S strain.

The effect of phenolic compounds, ethyl alcohol, and sodium metabisulphite on the lytic activity of virulent bacteriophage PL-1 on a Lactobacillus casei S strain isolated from a lactic acid beverage fermentation was investigated. Catechin, caffeic, and gallic acids, commercially produced red, white, and champagne tannins, ethyl alcohol, and sodium metabisulphite inhibited plaque formation. Catechin, caffeic, and gallic acids were the most effective inhibitors of plaque formation. Commercially supplied oenocyanin was not effective.

Bacteriophages↗
PubMed2004

Effects of polyphenols from grape seeds on oxidative damage to cellular DNA.

Grape seed polyphenols have been reported to exhibit a broad spectrum of biological properties. In this study, eleven phenolic phytochemicals from grape seeds were purified by gel chromatography and high performance liquid chromatography (HPLC). The antioxidant activities of five representative compounds with different structure type were assessed by the free radical-scavenging tests and the effects of the more potent phytochemicals on oxidative damage to DNA in mice spleen cells were investigated. Procyanidin B4, catechin, epicatechin and gallic acid reduced ferricyanide ion and scavenged the stable free radical, alpha, alpha-diphenyl-beta-picrylhydrazyl (DPPH) much more effectively than the known antioxidant vitamin ascorbic acid, while epicatechin lactone A, an oxidative derivative of epicatechin, did not reduce ferricyanide ion appreciably at concentrations used and was only about half as effective on free radical-scavenging as epicatechin. Mice spleen cells, when pre-incubated with relatively low concentration of procyanidin B4, catechin or gallic acid, were less susceptible to DNA damage induced by hydrogen peroxide (H2O2), as evaluated by the comet assay. In contrast, noticeable DNA damage was induced in mice spleen cells by incubating with higher concentration (150 microM) of catechin. Collectively, these data suggest that procyanidin B4, catechin, gallic acid were good antioxidants, at low concentration they could prevent oxidative damage to cellular DNA. But at higher concentration, these compounds may induce cellular DNA damage, taking catechin for example, which explained the irregularity of dose-effect relationship.

Animals↗
PubMed1996

The interaction of polyphenols with bilayers: conditions for increasing bilayer adhesion.

Because proteins and other molecules with a high polyphenol content are commonly involved in adhesion processes, we are investigating the interactions between polyphenols and biological materials. A naturally occurring polyphenol that binds a variety of proteins and lipids is tannic acid (TA), which contains five digallic acid residues covalently linked to a central D-glucose. A previous study has shown that TA increases the adhesion between apposing phosphatidylcholine (PC) bilayers and over a very narrow concentration range collapses the interbilayer fluid space from about 15 A to 5 A. To determine the chemical requirements a polyphenolic molecule must possess to increase bilayer adhesion, we have synthesized several simpler TA analogs that vary in their size, shape, and number of gallic acid and hydroxyl groups. X-ray diffraction, absorbance, binding, and differential scanning calorimetry measurements were used to investigate the interaction of these polyphenolic molecules with egg PC (EPC) and dipalmitoyl PC (DPPC) bilayers. Of these synthetic polyphenols, only penta-O-galloyl-alpha-D-glucose (PGG) was able to completely mimic the effects of TA by collapsing the interbilayer fluid space from 15 A to 5 A, decreasing the dipole potential by about 300 mV, increasing the transition enthalpy of DPPC liposomes, and inducing an interdigitated phase in DPPC. Binding studies indicated that the fluid space was reduced to 5 A at an EPC:PGG mole ratio of 5:1. We conclude that these polyphenols collapse the fluid space of PC bilayers because they 1) are amphipathic and partition into the bilayers interfacial region, 2) are long enough to span the interbilayer space, 3) contain several gallic acids distributed so that they can partition simultaneously into apposing bilayers, and 4) have sufficient gallic acid residues to interact with all lipid headgroups and cover the bilayer surface. Under these conditions we conclude that the polyphenols from interbilayer bridges. We argue that these bridges are stabilized by increased adhesion arising from an increased van der Waals interaction between apposing bilayers, electrostatic interactions between the pi electrons in the phenol ring and the -(N+CH3)3 groups on the PC headgroups, decreased hydration repulsion between bilayers, and hydrogen bonds between the H-bond-donating moieties on the polyphenols and H-bond-accepting groups in the bilayer.

1,2-Dipalmitoylphosphatidylcholine↗