The data demonstrate that ellagic acid inhibits carcinogenesis in nitrosamine-induced lung tumors in mice and in esophageal tumors in rats.152,153 In another study, ellagic acid has been reported to induce apoptosis in pancreatic and leukemia cancer cells.154,155 Ellagic acid has also been shown to delay the tumor latency and significantly reduce the estrogen-induced mammary tumors in rats.156 Moreover, it has been found to induce apoptosis in 1,2-dimethyl hydrazine (DMH)-mediated colon carcinogenesis in rats.157 The data from another study provide evidence that ellagic acid inhibits the initiation of DMH-induced colon carcinogenesis by reducing lipid peroxidation, DNA damage through increasing cellular antioxidant status. The day-1 (HH Stage 46) chicks were collected. Gallic acid is a well known antioxidant compounds which has neuroprotective actions in different models of neurodegeneration, neurotoxicity and oxidative stress. The antitumorigenic and antiinflammatory activities of polyphenols such as ellagitannins and anthocyanins (grape seeds) in pomegranate were linked to the upregulation of miR-126, which correlated with vascular cell adhesion molecule 1 (VCAM-1) and miR-126/phosphatidylinositol-3-kinase (PI3K)/AKT/mammalian target of rapamycin (mTOR) inhibition in HT-29 colon cancer cell lines and AOM-induced rat carcinogenesis model [343]. The total yield of gallic acid was 30% at 45 h in the case of tara tannin and 9.7% in the case of sumac tannin, in terms of raw material weight (Pourrat et al., 1987). 101 2-Propenesulfenic acid is reported to be over 1000 times more reactive toward ˙OOH radicals than allicin (2.60 × 10 7 vs. 7.38 × 10 3 L mol −1 s −1, at 298 K). Both LIFR and gp130 include components of the receptors for the majority of hematopoietic cytokines [45], further implicating the alternate role of GA in inducing embryonic hemolysis (Fig 1). This is an open access article distributed under the terms of the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original author and source are credited. Severe cerebral hemolysis was observed in day-9.5 embryos (Fig 1B). Gallic acid is found in the leaves of bearberry, in pomegranate root bark, gallnuts, witch hazel, sumac, tea leaves, oak bark, and many other plants, both in its free state and as part of the tannin molecule. The potential mechanisms of action of SmEE were also observed. However, some polyphenols can simultaneously act as both scavengers and ROS forming agents [48]. Zenker’s necrosis, liposis, and severe edema with focal infiltration were frequently observed and the body weight decreased severely. Click through the PLOS taxonomy to find articles in your field. The potential mechanisms of action of SmEE were also observed. The aim of the present study was to elucidate whether gallic acid modulates the inflammatory allergic reaction and to study its possible mechanisms of action. No, Is the Subject Area "Chicken eggs" applicable to this article? Thus far, most cited GA effects have been positive regarding antiteratogenesis [12, 13]; only a few studies have implicated negative effects caused by its prooxidative activity, including damage to aorta vascular smooth muscle cells (VSMCs) [14] and cytotoxic effects on testicular cells [15]. ... - and prooxidant properties however recently they have been described as potential anti-biofilm agents although their mechanisms of action on bacterial cells remain obscure. Orthoquinones formed by the loss of 2 electrons from pyrogallol and catechol (2 adjacent phenol groups) moieties can biochemically participate in enzymatic redox cycling reactions, which can produce superoxides and other ROS [50]. AU - Hsieh, Chiu Lan. In this study, the mechanism of action of gallic (GA) and ferulic (FA) acids, a hydroxybenzoic acid and a hydroxycinnamic acid, was assessed on Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, and Listeria monocytogenes. The membranes were then washed with the TBS buffer and the signals were visualized using a Luminescent Image Analyzer LAS-4000 (Fujifilm, Tokyo, Japan). Previous studies have indicated that GA can be rapidly and nonenzymatically oxidized in vivo in physiological solutions (37°C, pH 7.4) to produce superoxide anions, H2O2 and GA quinones [31–33]. Introduction. Yes Lower row: back view. However, gallic acid indicated no linear dependence on both [InH] −1 and [InH] −0.5, which showed that the radicals of gallic acid were included in more than one reaction of chain propagation (Figure 6b). It is known that gallic acid shows antimicrobial activity. Tannic acid, a naturally occurring plant polyphenol, is composed of a central glucose molecule derivatized at its hydroxyl groups with one or more galloyl residues, whereas gallic acid is a trihydroxybenzoic acid, also known as 3,4,5-trihydroxybenzoic acid, which is widely distributed in green tea, red wine and grapes, witch hazel, sumac, oak bark, and other plants . This is because FR diffuse and spread easily. Gallic acid is produced chemically by the hydrolysis of tannic acid by sulfuric acid at 110–120 °C. Distinct organs exhibited varying susceptibilities to GA. Because the decreases in body and organ weights occurred simultaneously in a dose-responsive manner, the organ weight related to body weight did not differ in the various treatment groups (Table 2). Impact of Gallic Acid on Gut Health: Focus on the Gut Microbiome, Immune Response, and Mechanisms of Action Front Immunol . An important source of gallic acid is also tea containing up to 4.5 g/kg fresh weight in tea leaves.144 Gallic acid has been shown to exhibit biological activity, including anticancer. It melts at 250 °C, and above this temperature gallic acid is converted into carbon dioxide and pyrogallol. Table 1: Action of Gallic acid (GA) on different cancer cell line. Gallic acid conjugated with gold nanoparticles: antibacterial activity and mechanism of action on foodborne pathogens Narintorn Rattanata , 1 Sompong Klaynongsruang , 1 Chanvit Leelayuwat , 2 Temduang Limpaiboon , 2 Aroonlug Lulitanond , 2 Patcharee Boonsiri , 3 Sirinart Chio-Srichan , 4 Siriwat Soontaranon , 4 Supagorn Rugmai , 4 and Jureerut Daduang 2 The proteins were electrotransferred onto a PVDF membrane in transfer buffer for 1 h. The nonspecific binding to the membrane was blocked for 1 h at room temperature with 5% nonfat milk in a TBS buffer. Gallic acid (3,4,5-trihydroxybenzoic acid) (GA) and other flavanoids are extensively used in nutraceuticals because of their antioxidant and antiinflammatory properties. Gallic acid (GA) is a member of the hydroxybenzoic acids found in methyl acetate fraction and hydroalcoholic extract from Schinus terebinthifolius leaves.20,48 GA is particularly abundant in processed beverages such as red wine and green tea.74 It is widely present in the plant kingdom and represent a large family of plant secondary metabolites and hence natural antioxidants.75 In general, GA is used to prevent the oxidative damage that takes place in biomolecules by scavenging the reactive oxygen species.76,77 Other biological studies show that GA has various properties, including antifungal, antimicrobial, and anticancer activities.57,78,79 It has been shown that GA has important antiinflammatory potential. Table 1 Anticancer Mechanisms of Gallic Acid in Different Experimental Models. Cerebral hemorrhage can be at least partially attributed to the strong prooxidant characteristic of GA [16, 23, 24]. Wrote the paper: CLH KCC RYP. With this proviso and by the use of the strict linearity range, the values obtained for gallic acid were 98±2.1% of those found by HPLC. AU - Peng, Chiung Chi. Graduate Institute of Clinical Medicine; Research output: Contribution to journal › Article. This effect was associated with upregulation of miR-126 and suppression of PI3K, AKT, hypoxia inducible factor-1α (HIF-1α), and VEGF mRNA levels, and pAKT, AKT, pPI3K (p85), VEGF and nuclear factor-kappa B (NF-κB) protein levels [342]. Hence, a large portion of ferric ions might remain in a free ion state, which, in turn, can accelerate the coupling of Harber-Weiss [46] and Fenton reactions and enhance the cyclic hydroxyl free radical oxidative stress on cell proliferation [17] (Fig 6; see the Supplement). GA increases ROS levels, including •O2-, induces GSH depletion, and inhibits the growth of lung cancer and normal cells [34]. The blue arrows indicate the nuclei released after collapsed. Photos of the whole chicks and the organs were taken. Gallic acid attenuated compound 48/80- or immunoglobulin E (IgE)-induced histamine release from mast cells. A summary of the signal pathway is shown in Fig 6. Insulin resistance is often associated with increased levels of intracellular triglycerides, diacylglycerol and decreased fat β-oxidation [38]. The parallel modulation pattern of PPARα and insulin implicates a close link between these 2 parameters [39]. These cells are key participants of inflammatory signals in the inflamed rheumatoid synovium, mediating direct tissue damage and persistent cellular infiltration in the disease.80 GA treatment also suppresses the levels of proinflammatory cytokines IL-1 and IL-6, chemokines CCL-2 and CCL-7, cyclooxygenase-2 (COX-2), and matrix metalloproteinase-9 (MMP-9) on RA FLS.58 This study indicates that GA may reduce the inflammatory response by limiting the abnormal proliferation of RA FLS. Research Institute of Biotechnology, Hungkuang University, Taichung City, Taiwan. Gallic acid derivatives have also been found in a number of phytomedicines with diverse biological and pharmacological activities, including radical scavenging, interfering with the cell signaling pathways and apoptosis of cancer cells. The reaction is taking place in the way that hydrogen of hydroxy group of GA is transferred to the oxygen of each of peroxy radical. The changes in PPAR-α explained why liposis accompanied hemolysis in the musculi longissimus cervicis when the chicken embryos were treated with GA; GA downregulated the level of PPAR-α in the musculi longissimus cervicis in a dose-responsive manner. However, the proliferative marker PCNA has been suggested to be directly related with the proliferation [42], futher work will be conducted to confirm this aspect. For more information about PLOS Subject Areas, click PPARα is able to improve insulin sensitivity [37]. Anand A. Zanwar, ... Subhash L. Bodhankar, in Polyphenols in Human Health and Disease, 2014. Significance determined by p < 0.05. Gallic acid was also identified as a versatile scavenger, capable of rapidly deactivating a wide variety of reactive oxygen species (ROS) and reactive nitrogen species (RNS) via electron transfer at physiological pH. 3-Dehydroshikimate is then reduced to shikimic acid by the enzyme shikimate dehydrogenase, which … The apoptosis induced by GA is atypical [14]. Shahidul Islam, in, Polyphenols: Mechanisms of Action in Human Health and Disease (Second Edition), Natural Epigenetic-Modifying Molecules in Medical Therapy, Production and Application of Tannin Acyl Hydrolase: State of the Art, Tannase hydrolyzes tannic acid to glucose and, ACIDS | Thin-Layer (Planar) Chromatography, International Journal of Biological Macromolecules. Moreover, GA-induced cell death is not prevented by Boc-Asp-fmk (a pan-caspase inhibitor) [14], indicating that neither the intrinsic nor extrinsic mitochondrial pathways are involved in GA-induced teratogenicity and hemolysis. Gallic acid and the three other primary hits that inhibited SP-mediated enhancement of HIV infection. Fitzpatrick, T. Woldemariam, in Comprehensive Medicinal Chemistry III, 2017. The erythrocyte, hemoglobin, eosinophil, lymphocyte, and monocyte counts were severely reduced and PPAR-α was downregulated, whereas the Ras/Raf/JAK/STAT pathway was upregulated. Tannase hydrolyzes tannic acid to glucose and gallic acid (Iibuchi et al., 1972). The GA dose required to induce teratogenesis was ≥ 6 μM (1.02 mg/kg), which can be easily consumed by pregnant women in typical teas such as Chinese Pu-’Er and Chinese black teas, indicating a potential risk to human fetuses. Gallic acid is the most popular of trihydroxybenzoic acids. In summary, a dose of GA > 0.34 mg/kg potentially exhibits teratogenicity. mechanisms of primary antioxidant action of gallic acid (Scheme 1) and corresponding carboxylic anion (Scheme 2) in the gas-phase, benzene and water. The released free ferric ion reacts with the superoxide anion (the Harber-Weiss reaction; Reaction XI) [14, 45], producing large amounts of ferrous ions (Fe2+), which rapidly undergo the Fenton reaction in the presence of hydrogen peroxide to yield additional hydroxyl free radicals [17] (Reaction XII). The embryos were successively rinsed several times with PBS and deionized water (DW). Embryos were observed on days 5.5 and 9.5, and chicks were observed on day 1 (HH Stage 46) [22]. . Gallic acid derivatives have also been found in a number of phytomedicines with diverse biological and pharmacological activities, including radical scavenging, interfering with the cell signaling pathways and apoptosis of cancer cells. Aβ25–35, 3-(4, 5-dimethylthiazol-2-yl)-2, 5-di-phenyl (MTT), Folin-Ciocalteau reagent (50%) was purchased from Sigma (St. Louis, MO, USA). Thus, a fetus can absorb highly concentrated GA if it is not rapidly degraded by maternal metabolism. Intriguingly, the anticolitis effect was attributed to the suppression of colonic NF-kB and STAT3 activation.54,96 Here is the structure of gallic acid. Tzi B. Ng, ... Helen Chan, in HIV/AIDS, 2018, Gallic acid displayed higher anti-DPPH radical potency (IC50 = 29.5 μM) and lower hydrophobicity (log P = −0.28) than methyl gallate (IC50 = 38.0 μM, log P = −0.23) and α-tocopherol (IC50 = 105.3 μM, log P = .70). GA is ineffective at protecting PC12 cells from death caused by H2O2 attacks [17]. By contrast, the hemoglobin level was severely suppressed only at much higher doses of GA (e.g., 14 μM) (Table 3). In the Hamilton-Hamburger (HH) stages [22], somite formation and neural folds occur early from stage 7 to stage 21, which corresponds to 23 h to 3.5 d. A blood island with 4 somites develops at Stage 8 (26–29 h). The subgroups were administered PBS (as the control), and 2, 6, 10, and 14 μM GA. Paraffin sections were dewaxed in xylene and rehydrated in a series of ethanol washes. No, Is the Subject Area "Tea" applicable to this article? GA downregulates Bcl-2 in PC12 cells through the combined effects of dietary phenolics and reactive oxygen species (ROS) on oxidative neuronal cell death [18]. Contributed reagents/materials/analysis tools: KCC CCP. No, Is the Subject Area "Embryos" applicable to this article? Compare Products: Select up to 4 products. PLOS ONE promises fair, rigorous peer review, GA was obtained from Dainippon Pharmaceutical Co., Ltd. (Osaka, Japan) as a yellowish–white crystalline powder with a purity of over 98%. At present, gallic acid is made industrially by chemical hydrolysis of naturally occurring gallotannins. Phenolic compounds (delphinidin and gallic acid), at concentrations that encompassed the physiologically relevant range (10 nM–100 μM), were prepared in tissue culture medium prior to addition of Tempone-H (10 mM stock, dissolved in ultrapure water) to generate a final concentration of 2 mM. T1 - The teratogenicity and the action mechanism of gallic acid relating with brain and cervical muscles. Blood was collected for counting. Yes Yes No, Is the Subject Area "Red blood cells" applicable to this article? Y1 - 2015/6/1. ); kasia.pustus@wp.pl (K.P.) https://doi.org/10.1371/journal.pone.0119516.s001. View larger version: In this window; In a new window; Download as PowerPoint Slide; FIGURE 1. It consists of three hydroxyl groups and a carboxylic acid group attached to a benzene ring. From day 9.5 to day 10, primitive chick morphology can be clearly observed, and, during this period, the length of the third toe from the tip to the middle of the metatarsal joint can reach 5.4 ± 0.3 mm; the length of the beak from the anterior angle of the nostril to the tip of the bill can reach 2.5 mm; and the primordium of the comb, the labial groove, and the uropygial gland are all well developed. Hence, the hemolytic effect in embryos might be partially induced by the autooxidative behavior of GA, whereby large amounts of ROS can be generated [14]. A compound that reduces in vitro radicals does not necessarily behave as an antioxidant in an in vivo system. In spleens, GA at 7 μM exhibited only an apparent weight-reducing effect (p < 0.05) (Table 2). Although VSMCs are positive for in situ nick end-labeling (TUNEL), they do not exhibit a DNA ladder pattern in gel electrophoresis and are negative for Taq polymerase-based in situ ligation, which is more specific for apoptosis than for TUNEL. β-actin was used as the reference protein. The extent of severity of edema and hemorrhage (A); and the scoring based on the degree of swelling and edema without hemorrhage (B). [9], a daily consumption of 5 g of Chinese Pu-’Er tea contains 74.5 mg of GA (or 1.24 mg/kg), corresponding to a serum level of 18.6 mg/L (109.3 μM), based on an assumed total blood volume of 4 L for a pregnant woman. The windows were then immediately sealed aseptically using 3M tape. Gallic acid is mainly used as a synthetic intermediate for the production of pyrogallol and gallic acid esters used in the food and pharmaceutical industries (Deschamps and Lebeault, 1984). Gallic acid is a very important common antioxidant tea formulation, known as an Ayurvedic herb. Recently, Ko et al. [37] reported its presence in the phenolic rich extract of C. volubile leaves. The oxidative stress can be effectively neutralized by enhancing cellular defens… According to previous studies, GA has many biological properties, including antioxidant, anticancer, anti-inflammatory, and antimicrobial properties. Gallic acid is a trihydroxybenzoic acid in which the hydroxy groups are at positions 3, 4, and 5. However, as the actual prevalence rate of hemolysis in embryos reached only 5.5–10.5% which was included in the damaging rate (as addressed in the footnote of Table 1), we established a subscoring system based on the degree of edema, liposis, and hemolysis for further clssification of the status (Fig 2B). The antihyperlipidemic action of gallic acid in high-fat diet induced mice revealed a decrease in triglyceride and low-density lipoprotein-cholesterol, and an increase in high-density lipoprotein-cholesterol. It is a white solid, although samples are typically brown owing to partial oxidation. Analyzed the data: RYP. Gallic Acid as Neuroprotective Agent. Sustained activation of the Ras/Raf/MEK/ERK pathway can lead to cell cycle arrest in numerous cell lines [41]. The mechanism of action of GA is multidisciplinary: Liposis can be ascribed to the downregulation of PPAR-α; erythrocyte hemolysis can be attributed to the unique autooxidative prooxidant behavior of GA and the inhibition of carbonic anhydrase; and proliferation and differentiation deficits can be attributed to the upregulation of the Ras/Raf/JAK/STAT pathway. The retarded transport and reduction of ferric ions can be the cause more relevantly to RBC production [25–27]. The alive day-1 chicks were euthanized under CO2-anethesia and the liver, pancreas, spleen, and necks of all chicks were excised, rinsed 3 times with PBS, dried using tissues, and weighed. The funder had no role in study design, data collection and analysis, decision to publish, or preparation of the manuscript. Normal saline was purchased fro China Pharmaceutical and Chemical Co. (Taipei, Taiwan). Normal biochemical reactions, increased exposure to the environment, and higher levels of dietary xenobiotics result in the generation of reactive oxygen species (ROS) and reactive nitrogen species (RNS).2 ROS and RNS are responsible for the oxidative stress in different pathophysiological conditions.3 Cellular constituents of our body are altered in oxidative stress conditions, resulting in various disease states. Our study reveals that GA is a potential antioxidant that directly upregulates the expression of antioxidant genes. It also reduces ACF proliferation and/or progression exerting chemopreventive activity against colon cancer.158 Ellagic acid may be considered in a promising new class of cancer chemopreventive and therapeutic agents. Gallic acid is utilized in the ink industry, dye industry, food industry (antioxidants and preservatives), and, most importantly, in the pharmaceutical industry (as a raw material for the production of the hallucinogenic alkaloid, mescaline, and trimethoprim, a broad-spectrum antibiotic). An inherent difficulty was found to be slight inhomogeneity in the coating of the fluorescent indicator: to improve on this, the plate was scanned before an assay to determine any background fluorescence, which was then subtracted to ‘zero’ the plate. To better understand the mechanism by which gallic acid inhibits SP-mediated enhancement of HIV infection, we set out to characterize its molecular interactions with SEVI and SEM1 fibrils. ScienceDirect ® is a registered trademark of Elsevier B.V. ScienceDirect ® is a registered trademark of Elsevier B.V. URL: https://www.sciencedirect.com/science/article/pii/B9780123984562000803, URL: https://www.sciencedirect.com/science/article/pii/B9780124095472124047, URL: https://www.sciencedirect.com/science/article/pii/B9780128138205000283, URL: https://www.sciencedirect.com/science/article/pii/B9780128098530000146, URL: https://www.sciencedirect.com/science/article/pii/B9780123984562000864, URL: https://www.sciencedirect.com/science/article/pii/B9780123739445001565, URL: https://www.sciencedirect.com/science/article/pii/B9780128130063000064, URL: https://www.sciencedirect.com/science/article/pii/B9780128032398000399, URL: https://www.sciencedirect.com/science/article/pii/S0065216408704635, URL: https://www.sciencedirect.com/science/article/pii/B0122267702025710, Polyphenols in the Prevention and Treatment of Vascular and Cardiac Disease, and Cancer, Anand A. Zanwar, ... Subhash L. Bodhankar, in, Cancer, Immunology and Inflammation, and Infectious Disease, Antiinflammatory Properties of Schinus terebinthifolius and Its Use in Arthritic Conditions, Elaine Cruz Rosas, ... Maria das Graças Henriques, in, Bioactive Food as Dietary Interventions for Arthritis and Related Inflammatory Diseases (Second Edition), Methyl Gallate as an Antioxidant and Anti-HIV Agent, Organic and Fatty Acid Production, Microbial, Encyclopedia of Microbiology (Third Edition), Clerodendrum volubile: Phenolics and Applications to Health, Ochuko L. Erukainure, ... Md. Previous studies have indicated that the biological actions of IL-6, leukemia inhibitory factor (LIF), and ciliary neurotrophic factor (CNTF) are mediated by respective functional receptor complexes (FRCs) consisting of a common signal-transducing component, gp130. The extracellular pathway mediates its effect through LIF expression and activation of JAK-STAT3. Considering the use of this species in ethnomedicine, its anti-inflammatory and antioxidant activities, our study investigated the antiulcerogenic activity of the Spondias mombin ethanolic extract (SmEE), isolated gallic acid (GA), and ellagic acid (EA) and in association between gallic acid and ellagic acid. https://doi.org/10.1371/journal.pone.0119516.t004. 133 - N° C - Article : 110985 - Gallic acid: Pharmacological activities and molecular mechanisms involved in inflammation-related diseases - EM consulte An alternative cause is discussed in the following sections. Conversely, quercetin retains full strength PPARα and is effective in acting as an antihypercholesterolemic, indicating that the complex hypercholesterolemia of CKD is controlled not only by mitochondrial fat oxidation [39]. Gallic acid has been detected in trace amounts in brains (mouse model of Alzheimer’s disease) after repeated administration of grape seed polyphenolic extract for 10 days (intragastric gavage of 50, 100 and 150 mg/kg b.w.) Gallic acid (3,4,5-trihydroxybenzoic acid) (GA) and other flavanoids are extensively used in nutraceuticals because of their antioxidant and antiinflammatory properties. After extensive washing in the TBS buffer, the membranes were = incubated with secondary antibodies in blocking buffer containing 5% nonfat milk for 1 h at room temperature. While examining whether GA is effective in alleviating valproic-acid-induced teratogenesis in a chicken embryo model (CEM), we observed embryo hemorrhage and liposis in the musculi longissimus cervicis. Affiliation The optimal alive birth rate (or damaging rate) reached 33.3%, 39.4%, and 29.2% at 6, 10, and 14 μM GA, respectively.

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