This study aimed to conjugate and characterize AuNP–GA and to evaluate the antibacterial activity. Gallic acid is a well-known natural antioxidant that is basically a secondary polyphenolic metabolite. Protocatechuic acid (PCA) is a type of widely distributed naturally occurring phenolic acid. VEGETABLE ASTRINGENTS, nearly all contain some form of tannic or Gallic Acid, on which their physiological and therapeutical properties depend. The concentration of tulathromycin was 0.08 and 0.16 μg/mL, respectively, and the concentration of gallic acid was from 3.91 to 250 μg/mL. Figure 5 illustrates the biosynthetic pathway of hydrolyzable tannins. Also known as 3,4,5-trihydroxybenzoic acid, gallic acid has been reported in most plants. Leite F, de Oli veira HC. Ceriops tagal 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. The bonding of the hydroxyl groups in an ortho position results in a coplanar and bent configuration, which is favorable for antioxidative activities [52,53], I. Goldberg, J.S. activities of gallic acid, delphinidin and pelargonidin-3-glucosides. In our studies, these phenolic compounds were evaluated: gallic acid, caffeic acid and pyrogallol. AIM: Gallic acid and its ester derivatives have shown antifungal activity in vitro. Antioxidant activity and inhibitory mechanism of γ-oryzanol as influenced by the unsaturation degree of lipid systems. The diverse range of applications of this simple polyphenol is due to a fine amalgam between its antioxidant and prooxidant potential. Penta-O-galloyl-glucose is a pivotal intermediate that leads to the synthesis of gallotannins and ellagitannins. Also, the physicochemical, structural, and energetic properties of GA and the nanohybrids were determined through structure–activity relationship (SAR). Anti-fungal Activity Journal of Biomolecular Structure and Dynamics. PCA has structural similarity with gallic acid, caffeic acid, vanillic acid, and syringic acid which are well-known antioxidant compounds. In this study comparison of effects of gallic acid with those of the ARB losartan, beta-blocker carvedilol, and diuretic furosemide was made. This study was performed to investigate their activity against Candida albicans and their toxicity in the animal models Caenorhabditis elegans and zebrafish embryos. Anand A. Zanwar, ... Subhash L. Bodhankar, in Polyphenols in Human Health and Disease, 2014. 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. Gallic acid h as been reported t o exert both pro-oxidant and antioxidant activities [13]. Background: Plant-phenolics and flavonoids, including gallic acid, quercetin and rutin, are considered as safe inhibitors for α-glucosidase. Gallic acid (GA), one of the most abundant phenolic acids in the plant kingdom, has been shown potential chemotherapeutic efficacy against microbial and cancer. Gallic acid is a phenolic compound also known as 3,4,5-trihydroxybenzoic acid. The antibacterial, antifungal and modulatory of antibiotic activities of these compounds were assayed using microdilution method of Minimum Inhibitory Concentration (MIC) to bacteria and Minimum Fungicide Concentration (MFC) to fungi. Carbohydrate Polymers 84: 690-693. On the other way, β-PGG can evolve through intra- and intermolecular phenolic coupling processes leading to the formation of covalent bond such as C–C biaryl and C–O diaryl ether bonds between two spatially adjacent galloyl groups. Showing all foods in which the polyphenol Gallic acid is found Food Composition. Antifungal, Antitumoral and Antioxidant Potential of the Danube Delta Nymphaea alba Extracts, European Journal of Lipid Science and Technology. The chronic liver diseases represent a major health problem worldwide, including alcohol abuse, metabolic disorders, steatosis, chronic viral hepatitis, and hepatocellular carcinoma, being major causes of chronic liver injury and subsequent complications which will require expensive and high-risk treatments, such as transplants.18, I. Ky, ... P.-L. Teissedre, in Encyclopedia of Food and Health, 2016. Gallic acid, 3, 4, 5-trihydroxybenzoic acid can be found in gallnuts, sumac, witch hazel, tea leaves, oak bark, etc. Request PDF | Gallic Acid: Prospects and Molecular Mechanisms of Its Anticancer Activity | Cancer is the second leading cause of death worldwide. Therefore, bioactive compounds with antibacterial activity, such as gallic acid (GA), are needed. It is found both as a free state and as a constituent of tannins, namely, gallotannin. Number of times cited according to CrossRef: 46 . It might be a potential preventive and therapeutic agent against gastric cancer metastasis.149 Another study in human glioma cells has indicated that gallic acid inhibits cell proliferation and significantly decreases cell viability, invasion and tube formation.150 All these findings suggest that further investigations on the use of gallic acid as a chemopreventive and therapeutic agent are warranted. It is typically used in Chinese herbal medicine. These findings reveal the role of gallic acid in E. officinalis mediated antidiabetic potential, and delineate the upregulation of pAkt, PPAR-γ and Glut4 in gallic acid mediated antidiabetic activity, thus providing potential therapy for diabetes and related disorders. GA suppressed the levels of NO, PGE2, and IL-6 in LPS-induced activation of RAW264.7 cells.56 Another study showed that GA could inhibit the production of IL-6 and IL-8 induced by Fusobacterium nucleatum in human mouth epithelial cells as well as the growth of F. nucleatum, indicating that GA is a good candidate for controlling periodontal disease.57 In addition, it was reported that GA significantly decreased the cell viability of fibroblast-like synovial cells (FLS) from patients with rheumatoid arthritis. Gallic acid is one of the most important organic compounds in fruits of Phyllanthus emblica. [citation needed] The chemical formula of gallic acid is C 6 H 2 3 COOH.It is found both free and as part of hydrolyzable tannins.The gallic acid groups are usually bonded to form dimers such as ellagic acid. Ellagic acid is a dimeric derivative of gallic acid occurring mostly in fruits and berries such as raspberries, strawberries, blackberries and pomegranates. In this study, antimicrobial activity of gallic acid-grafted-chitosans (gallic acid-g-chitosans) against five Gram-positive and five Gram-negative foodborne pathogens was evaluated. . Learn more. [37] reported its presence in the phenolic rich extract of C. volubile leaves. Choi HJ, Song HJ, Park KS, Baek SH (2010) In vitro anti‐enterovirus 71 activity of gallic acid from Woodfordia fruticosa flowers. 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. 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. Gallic acid is one of the major active component of Chinese gall, and is widely distributed in natural herbal plants and in large amounts of prescribed Chinese herbs (6,7). Methyl gallate exhibited higher antiperoxide activity in the bulk Kilka fish oil system than gallic acid and α-tocopherol, and higher activity than gallic acid although lower activity than α-tocopherol in the oil-in-water emulsion system stabilized by soy protein isolate at 55°C. Apart from its phytochemical role, gallic acid is also used in tanning, ink dyes, and the manufacture of paper. F2 is a polysaccharide also with reduced antioxidant activity. It has a role as an astringent, a cyclooxygenase 2 inhibitor, a plant metabolite, an antioxidant, an antineoplastic agent, a human xenobiotic metabolite, an EC 1.13.11.33 ( arachidonate 15-lipoxygenase) inhibitor and an apoptosis inducer. The minimum inhibitory concentrations (MICs) of gallic acid-g-chitosans ranged from 16 to 64 μg/mL against Gram-positive bacteria and ranged from 128 to 512 μg/mL against Gram-negative bacteria. The antioxidant activity of gallic acid and pyrogallol is studied by the DPPH• scavenging assay and the extent of oxidation inhibition of the triacylglycerols of various unsaturated oils (olive, sunflower, and soybean) and their oil‐in‐water emulsions. It consists of three hydroxyl groups and a carboxylic acid group attached to a benzene ring. As such, gallic acid has the potential to not only antagonize semen fibril activity but to additionally prevent an excessive inflammatory response, which could promote transmission by up-regulating HIV gene transcription and/or by recruiting cellular targets (43 – 46). The anti-peroxide activity in the bulk oil system decreased in the order of methyl gallate>gallic acid>α-tocopherol. This compound is a primary constituent of several tannin-bearing plants that produce ellagitannins.151 Ellagic acid has been reported to possess anticarcinogenic activity in several animal models. Oswaldo Cruz 2008; 103:437-442. Enzyme studies with extracts from oak leaves have shown that gallic acid is converted to β-glucogallin, which, in turn, is converted via a series of position-specific galloylation steps to penta-O-galloyl-glucose (β-PGG). Rokem, in Encyclopedia of Microbiology (Third Edition), 2009. The α-glucosidase inhibitory activities of the gallic acid-dextran conjugate and dextran were compared. studies Use the link below to share a full-text version of this article with your friends and colleagues. The intramolecular coupling leading to the formation of HHDP biaryl unit is the characteristic structural motif that defines ellagitannins since during acidic hydrolysis, it will lead to the formation of ellagic acid. This compound has antioxidant properties (an antioxidant is a substance that protects the body’s cells from the harmful free radicals) and helps to protect our cells against oxidative damage. Fitzpatrick, T. Woldemariam, in Comprehensive Medicinal Chemistry III, 2017. It is present in relatively high concentrations in a number of vegetal samples and in industrial wastes from where it could be extracted.4 Also, it comes from the hydrolysis of tannic acid (C76H52O46) by bioconversion with enzyme tannase, which is an extracellular inducible enzyme. Zero-value entries. Number of times cited according to CrossRef: A reconsidered approach providing kinetic parameters and rate constants to analyze the oxidative stability of bulk lipid systems. However, gallic acid itself also appears to have antioxidant, anticarcinogenic and antiangiogenic activity in vitro. It has a molecular weight of 170.12 g/mol, is a monomeric phenolic compound solid, and colorless, which is bound to sugars and belong to group of hydrolysable tannins.3 GA can be found in plant material as free acid, esters, catechin derivatives, and hydrolysable tannins. in vitro Gallic acid, caffeic acid, and p-coumaric acid exhibited the IC 50 values of 737, 828, and >3000 µM, respectively, against α-glucosidase activities . 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). Gallic Acid is obtained from the same galls, after exposure in a warm place for a month; or from Tannic Acid by the action of dilute Sulphuric Acid. Gallic acid is easily freed from gallotannins by acidic or alkaline hydrolysis. Gallic acid reduced the activity of sterol 14α‐demethylase P450 (CYP51) and squalene epoxidase in the T. rubrum membrane, respectively. When heated with concentrated sulfuric acid, gallic acid converts to rufigallol. e DPPH scavenging activity of the extract may be due to its ability to donate hydrogen ions to stabilize free radicals. 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). Regarding the prevention of the triacylglycerols from oxidation, gallic acid is of higher activity than pyrogallol in the bulk oils (86.1–1244.3 vs. 73.4–331.6) but of lower activity in the O/W emulsions (13.0–74.9 vs. 17.4–207.9), depending on their different antioxidant behaviors arisen from the free radical chain mechanism of action as well as interfacial phenomena. Also, cardioprotective action in isoprenaline induced cardiotoxicity and streptozotocin-induced diabetic rats revealed a protective effect of gallic acid with respect to several biochemical and histopathological parameters. Gallic acid was shown to have positive effects on hypertension, vascular calcification, cardiac remodeling, and fibrosis [236–238]. in silico Moreover, gallic acid inhibited MMP-2 and MMP-9 proteolytic activity with very similar potency. 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/B9780124095472124047, URL: https://www.sciencedirect.com/science/article/pii/B9780123984562000803, URL: https://www.sciencedirect.com/science/article/pii/B9780128138205000283, URL: https://www.sciencedirect.com/science/article/pii/B9780128130063000064, URL: https://www.sciencedirect.com/science/article/pii/B9780123739445001565, URL: https://www.sciencedirect.com/science/article/pii/B9780128098530000146, URL: https://www.sciencedirect.com/science/article/pii/B9780128137062000063, URL: https://www.sciencedirect.com/science/article/pii/B9780123984562000864, URL: https://www.sciencedirect.com/science/article/pii/B9780128039519000264, URL: https://www.sciencedirect.com/science/article/pii/B9780123849472006838, Polyphenols in Human Health and Disease, 2014, Cancer, Immunology and Inflammation, and Infectious Disease, Polyphenols in the Prevention and Treatment of Vascular and Cardiac Disease, and Cancer, Anand A. Zanwar, ... Subhash L. Bodhankar, in, 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), Clerodendrum volubile: Phenolics and Applications to Health, Ochuko L. Erukainure, ... Md. Gallic acid is a very important common antioxidant tea formulation, known as an Ayurvedic herb. bic acid exhibited DPPH radical scavenging activities in a concentration-dependent manner. They can cause significant damage to parts of cells such as DNA, proteins, an… Working off-campus? Gallic acid, caffeic acid, and p-coumaric acid exhibited the IC 50 values of 737, 828, and >3000 µM, respectively, against α-glucosidase activities . Chemical structure of gallic acid. Antibiotic drug resistance is increasing. 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. Adefegha and Oboh [36] and Oboh et al. More than 500 plants contain PCA as active constituents impartin… Gallic acid and its derivatives are present in nearly every part of the plant, such as bark, wood, leaf, fruit, root, and seed.95 Gallic acid has been shown to effectively suppress DSS-induced colitis in mice. Gallic acid is produced chemically by the hydrolysis of tannic acid by sulfuric acid at 110–120 °C. The nature of the atropisomeric form of these chiral biaryl motifs, such as the (S)-HHDP unit of the tellimagrandins or the (R)-HHDP unit of geraniin, is determined by the position of the galloyl motifs on the glucopyranose core in either its 4C1- or its 1C4-conformation. Enter your email address below and we will send you your username, If the address matches an existing account you will receive an email with instructions to retrieve your username, I have read and accept the Wiley Online Library Terms and Conditions of Use. Gallic acid with the lowest hydrophobicity (log P=-0.28) was found to be the most active antiradical agent (IC50=29.5 μM), followed by methyl gallate (IC50=38.0 μM, log P=-0.23) and α-tocopherol (IC50=105.3 μM, log P=0.70). By continuing you agree to the use of cookies. Gallic acid possesses antioxidant, antifungal, antiviral, anticancer activities [1-3]. Gallic acid is a trihydroxybenzoic acid of plant metabolites widely spread throughout the plant kingdom. It has a role as an astringent, a cyclooxygenase 2 inhibitor, a plant metabolite, an antioxidant, an antineoplastic agent, a human xenobiotic metabolite, an EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor and an apoptosis inducer.It is a conjugate acid of a gallate. A smart advanced chemiluminescence-sensing platform for determination and imaging of the tissue distribution of natural antioxidants. . Renata Nowak, ... Natalia Nowacka, in Polyphenols in Human Health and Disease, 2014. Following the extraction of gallic acid (e.g., by diethyl ether), these processes resulted in good yield of gallic acid (up to about 95% of available tannic acid), with a minimum energy input and probably more economical, as compared to the conventional industrial acid hydrolysis process. Gallic acid [3,4,5-trihydroxybenzoic acid (GA)], a natural phytochemical, is known to have a variety of cellular functions including beneficial effects on metabolic syndromes. Furthermore, the DHHDP unit can also undergo many additional transformations leading to the formation of the chebuloyl and elaeocarpusoyl ester groups, which characterized hydrolyzable tannins classified as Okuda's type IV. Moreover, the HHDP motif can go through additional oxidation transformation leading to the DHHDP unit that featured hydrolyzable tannins classified as Okuda's type III (i.e., dehydroellagitannin) such as geraniin. Practical Applications: The present study clarifies the role of the carboxyl group in gallic acid antioxidant activity, antioxidant activity as a function of the free radical chain mechanism as well as interfacial phenomena, critical concentration of reverse lipid hydroperoxide micelles as affected by the antioxidant activity, and the effect of the degree of lipid unsaturation on the antioxidant activity of gallic acid and pyrogallol. Gallic acid is a trihydroxybenzoic acid in which the hydroxy groups are at positions 3, 4, and 5. Gallic acid is a ubiquitous compound, widely distributed in the vegetal kingdom and frequently found in the human diet. 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. Flavonoids and polyphenols are heterocyclic molecules that have been associated with beneficial effects on human health, such as reducing the risk of various diseases like cancer, diabetes, and cardiovascular and brain diseases. Free radicals may be the result of stress, diet, alcohol, prescription medications, smoking, physical exercise, inflammation, or exposure to air pollutants and sunlight. Gallic acid is biosynthesized from 3-dehydroshikimate in a reaction catalyzed by shikimate dehydrogenase to give 3,5-didehydroshikimate, which then undergoes tautomerization to form gallate [50,51]. 26.1). Critical kinetic parameters and rate constants representing lipid peroxidation as affected by temperature. It is thought to regulate various cellular pathways, such as the bone morphogenetic protein 2 (BMP2)-Smad1/5/8 signaling [236], c-Jun N-terminal kinases 2 (JNK2) signaling and Smad3 binding activity [237], and histone deacetylase 1 or histone deacetylase 2 [238]. Qualitative and Quantitative Analysis of Ukrainian Iris Species: A Fresh Look on Their Antioxidant Content and Biological Activities. 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. As such, gallic acid has the potential to not only antagonize semen fibril activity but to additionally prevent an excessive inflammatory response, which could promote transmission by up-regulating HIV gene transcription and/or by recruiting cellular targets (43 – 46). Mem Inst . In summary, the anti-HSV-2 activity of gallic acid and pentyl gallate was ascribed to their virucidal effect on virus particles, a change that was likely accompanied by partial inhibition of the virus attachment to cells and its subsequent cell-to-cell spread activity. Lett Appl microbiol 50: 438-440 L. Mitigates 1,2-Dimethyl Hydrazine Induced Colon Carcinogenesis in Wistar Rats Moreover, gallic acid inhibited MMP-2 and MMP-9 proteolytic activity with very similar potency. This study demonstrates, for the first time, the presence of both gallic acid derivatives and polysaccharides as major antioxidant principles of the aqueous extract of rose flowers. To further verify the effect of gallic acid on ADAM17, an α-secretase activity assay kit was employed to measure ADAM17 activity. Another study investigated the effect of gallic acid in a mouse model of pressure overload-induced HF and in cultured rat fibroblast cells [239]. Gallic acid (GA), a hydrolyzable tannin, has a wide range of pharmacological activities. and you may need to create a new Wiley Online Library account. 95 Gallic acid has been shown to effectively suppress DSS-induced colitis in mice. Author information: (1)Pharmacognosy Department, Faculty of Pharmacy, Cairo University, Kasr El Aini st., P. B. Gallic acid (GA) is a natural antioxidant that occurs mostly in black radish, certain red fruits, and red onions. Elaine Cruz Rosas, ... Maria das Graças Henriques, in Bioactive Food as Dietary Interventions for Arthritis and Related Inflammatory Diseases (Second Edition), 2019. Chromatography; Chromatography after hydrolysis; Display Options . Tannic Acid is best used locally, and for astringent effect on the intestinal canal; Gallic Acid systemically, and for action on remote parts. Various in vitro and in vivo experiments of GA against a variety of cancer cell lines were reported. Farag MA(1)(2), Al-Mahdy DA(3), Salah El Dine R(3), Fahmy S(3), Yassin A(4), Porzel A(5), Brandt W(3). Hematemesis, not due to inflammation,—Tannic Acid, gr. An evaluation of the anti-cancer activity in HeLa cancer cells indicated that both peptides are active, but that coupling gallic acid at the N-terminus decreased the activity of the free peptide.
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