The diverse range of applications of this simple polyphenol is due to a fine amalgam between its antioxidant and prooxidant potential. Sort by. Toxicological implications of amplifying the antibacterial activity of gallic acid by immobilisation on silica particles: A study on C. elegans. GA has many applications in different areas like (1) pharmaceutical, manufacturing of broad spectrum antibiotics, and trimethoprim; (2) industrial, in the treatment of tanning animal hides and skins8; also it used as a photographic developer and in different types of inks9; (3) food, has been used as an antioxidant in fats and oils and as an additive in some types of beverages and foods, avoiding oxidation thereof.10, Moreover, it has been reported that GA is capable of regulating several biological activities, such as antiinflammatory, antibacterial, antioxidant, cardioprotective, antiviral, and anticancer.11,12 These processes occurs possibly because it is a potent antioxidant as it has an important role in absorbing and neutralizing free radicals, with even greater results than some vitamins.13 However, it can also promote cellular oxidative stress, as may have prooxidant activity causing cytotoxicity in some cases.14 Meanwhile, some authors reported the generation of reactive oxygen species (ROS) produced by GA induces apoptosis in cancer cell cultures in vitro.15, Studies with GA, obtained from food and plants, have shown that this compound has anticancer activity against various cancers, interfering at different stages of tumor development, suppressing angiogenesis, and metastasis in some cases.16 Also, some authors mentioned that the GA is responsible, in part, of antiangiogenic activities in some tumor cell lines, such as lung, prostate, bladder, brain, kidney, leukemia, and liver.17 As known, liver is vital for most of the biochemical processes in the organism, so that damage in it could be deadly. and you may need to create a new Wiley Online Library account. Gallic acid (3,4,5-trihydroxybenzoic acid, C7H6O5) (Figure 29) forms white, yellowish-white, or pale fawn-colored crystals of organic acid. Figure 5 illustrates the biosynthetic pathway of hydrolyzable tannins. Citing Literature. 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. 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. 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. Also known as 3,4,5-trihydroxybenzoic acid, gallic acid has been reported in most plants. In the present study, gallic acid was isolated as a natural antioxidant from Chinese gall. Biological evaluation of gallic acid and quercetin derived from e DPPH scavenging activity of the extract may be due to its ability to donate hydrogen ions to stabilize free radicals. Gallic acid is a hydroxybenzoic acid occurring mostly in certain red fruits, black radish, and onions. Gold nanoparticles (AuNPs) are used as drug delivery agents. By continuing you agree to the use of cookies. 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]. Working off-campus? 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 typically used in Chinese herbal medicine. Figure 26.1. This study aimed to conjugate and characterize AuNP–GA and to evaluate the antibacterial activity. They can cause significant damage to parts of cells such as DNA, proteins, an… Gallic acid is … Phenolic Acids of Plant Origin—A Review on Their Antioxidant Activity In Vitro (O/W Emulsion Systems) Along with Their in Vivo Health Biochemical Properties. Gallic acid may also benefit diabetes patients by triggering the release of insulin by the pancreatic cells, says a study published in the January 2010 issue of the “Phytothreapy Research.” However, they may not replace your existing diabetes medications, and do not use them without consulting your doctor. Another study investigated the effect of gallic acid in a mouse model of pressure overload-induced HF and in cultured rat fibroblast cells [239]. In an acute oral toxicity study, at 5000 mg/kg p.o. The total phenol content (TPC) of the extracts was determined by the Folin-Ciocalteu method and expressed as gallic acid equivalent (GAE). Silva ACPE, Costa Orlandi CB, Gullo FP, Sangalli . 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. Copyright © 2021 Elsevier B.V. or its licensors or contributors. Choi HJ, Song HJ, Park KS, Baek SH (2010) In vitro anti‐enterovirus 71 activity of gallic acid from Woodfordia fruticosa flowers. Showing all foods in which the polyphenol Gallic acid is found Food Composition. 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]. Gallic acid is one of the most important organic compounds in fruits of Phyllanthus emblica. Learn more. 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. Allelopathic Potential and Active Substances from Wedelia Chinensis (Osbeck). Gallic acid is a phenolic compound also known as 3,4,5-trihydroxybenzoic acid. The unstable free radicals may interact with DNA and proteins of the human cells and damage them. Mem Inst . 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. The inhibition of cell-free supernatants of several lactic acid bacteria on the selected psychrophilic spoilage bacteria in liquid whole egg. 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. To further verify the effect of gallic acid on ADAM17, an α-secretase activity assay kit was employed to measure ADAM17 activity. Antifungal, Antitumoral and Antioxidant Potential of the Danube Delta Nymphaea alba Extracts, European Journal of Lipid Science and Technology. Methanolic Extract of . 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-Hecate showed lower activity in non-tumor keratinocyte cells but higher hemolytic activity. In our studies, these phenolic compounds were evaluated: gallic acid, caffeic acid and pyrogallol. Anand A. Zanwar, ... Subhash L. Bodhankar, in Polyphenols in Human Health and Disease, 2014. Renata Nowak, ... Natalia Nowacka, in Polyphenols in Human Health and Disease, 2014. NMR and molecular modelling experiments confirmed the interaction of gallic acid with MMP-2, and suggested that it takes place within the catalytic center. . Critical kinetic parameters and rate constants representing lipid peroxidation as affected by temperature. Materials and Methods: Pure compounds of GA, QUE, and RUT were used. 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). 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. The gallic acid molecule contains two functional groups, hydroxyl groups and a carboxylic acid group, and therefore two molecules of the acid can interreact to yield numerous esters and salts, including digallic acid. If you do not receive an email within 10 minutes, your email address may not be registered, whether the chelating activity of gallic acid can be increased by alkaline pH since gallic acid radicals are anionic [18] making the compound more suitable for metal complexation. 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. [38] also compared its concentration in the ethyl acetate, ethanol, and methanol extracts of C. volubile leaves, with the ethyl acetate extract having the least concentration. 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. 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. PCA has structural similarity with gallic acid, caffeic acid, vanillic acid, and syringic acid which are well-known antioxidant compounds. and Tannase is the principal enzyme acting in the oxidation process, which penetrates the ester links and transformed into hydrolysable tannins and GA esters.5 Similarly, this natural phenolic compound is obtained from (1) plants: gobernadora and damiana; (2) fruit: grapes, pomegranate, nuts, strawberry, raspberry, lemon, apple peel, and mango; (3) vegetables: chard and spinach; (4) drinks: coffee, wine, and green tea.6 GA extraction from natural sources has been performed with polar solvents as water, ethanol, and methanol or combinations of them.7. 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). Author information: (1)Pharmacognosy Department, Faculty of Pharmacy, Cairo University, Kasr El Aini st., P. B. in silico In this study, we evaluated whether gallic acid, a phenolic acid identified in various plants such as gallnuts, possesses antimicrobial activity, potentiates the antimicrobial function of tulathromycin, and reduces or delays AMR to tulathromycin against two key causing-pathogens of BRD, M. haemolytica and P. multocida. In this study, we showed that gallic acid was active against both Mannheimia haemolytica and Pasteurella multocida, two key BRD associated-pathogens, with the minimum inhibitory concentration (MIC) measured at 250 and 500 μg/mL, respectively. Antioxidant activity of extracts from the wood and bark of Port Orford cedar Abstract Heartwood, sapwood, and inner and outer bark of Port Orford cedar were extracted with methanol, and the extracts evaluated for antioxidant activity. Gallic acid is a trihydroxybenzoic acid in which the hydroxy groups are at positions 3, 4, and 5. In the present work, its primary antioxidant activity has been investigated using the density functional theory (DFT), and the quantum mechanics-based test for overall free radical scavenging activity (QM-ORSA) protocol. 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. Shahidul Islam, in, Polyphenols: Mechanisms of Action in Human Health and Disease (Second Edition), Organic and Fatty Acid Production, Microbial, Encyclopedia of Microbiology (Third Edition), Methyl Gallate as an Antioxidant and Anti-HIV Agent, Gallic Acid as a Putative Antioxidant in Usage Against Liver Disease, Mayela Govea-Salas, ... Jesus Morlett-Chávez, in, Journal of Photochemistry and Photobiology B: Biology. Cho YS, Kim SK, Ahn CB, Je JY (2011) Inhibition of acetylcholinesterase by gallic acid-grafted-chitosans. 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. Ellagic acid is a dimeric derivative of gallic acid occurring mostly in fruits and berries such as raspberries, strawberries, blackberries and pomegranates. Gallic acids antioxidant activity could potentially work well against the high oxidative stress that skin cells come under frequently from actions of UV radiation-induced free radicals. Gallic acid is easily freed from gallotannins by acidic or alkaline hydrolysis. Fitzpatrick, T. Woldemariam, in Comprehensive Medicinal Chemistry III, 2017. A smart advanced chemiluminescence-sensing platform for determination and imaging of the tissue distribution of natural antioxidants. And in a subacute toxicity study, 1000 mg/kg p.o. Gallic acid possesses antioxidant, antifungal, antiviral, anticancer activities [1-3]. 57. studies Adefegha and Oboh [36] and Oboh et al. Gallic acid has been found to induce apoptosis of cancer cells via the mitochondria-mediated pathways and to show selective toxicity for cancer cells without harming normal cells.148 Gallic acid has also been reported to exhibit anti-invasive and anti-metastatic activities in various cancer cells. The dodecyl gallate was the most effective. Gallic acid has been found to induce apoptosis of cancer cells via the mitochondria-mediated pathways and to show selective toxicity for cancer cells without harming normal cells. Interestingly, a phenolic compound like GA was recently associated with cell death caused by hide show. In vivo model demonstrated that intraperitoneal injection administration of GA (80 mg/kg d) significantly enhanced the cure rate in a mice infection model of systemic fungal infection. Rokem, in Encyclopedia of Microbiology (Third Edition), 2009. Gallic acid is a very important common antioxidant tea formulation, known as an Ayurvedic herb. Gallic acid is a water soluble phenolic acid present in grapes and in the leaves of many plants. Chemical structure of gallic acid. 26.1). 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). Comparative antioxidant performance of gallic acid and pyrogallol to scavenge 1,1‐diphenyl‐ 2‐picrylhydrazyl radical (DPPH•) in a methanolic system and to inhibit peroxyl radical (LOO•) in triacylglycerols of olive, sunflower, and soybean oils and their oil‐in‐water (O/W) emulsions. The anti-peroxide activity in the bulk oil system decreased in the order of methyl gallate>gallic acid>α-tocopherol. Journal of Biomolecular Structure and Dynamics. Also, the physicochemical, structural, and energetic properties of GA and the nanohybrids were determined through structure–activity relationship (SAR). Previous studies have demonstrated a variety of biological activity of gallic acid (GA) including antitumoral, antioxidant and antiinflammatory properties. It melts at 250 °C, and above this temperature gallic acid is converted into carbon dioxide and pyrogallol. Please check your email for instructions on resetting your password. Gallic acid and its derivatives are present in nearly every part of the plant, such as bark, wood, leaf, fruit, root, and seed. The antihyperglycemic, antilipid peroxidative, and antioxidant effects could be the probable mechanism of action responsible for cardioprotective activity of gallic acid. 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. In all, 14 compounds such as gallic acid and luteolin in S20b were analysed by UFLC‐Q‐TOF‐MS/MS. L. Mitigates 1,2-Dimethyl Hydrazine Induced Colon Carcinogenesis in Wistar Rats Phytochemicals such as phenolics, tannins, flavonoids, carbohydrates, glycosides, phytosteroids, … Moreover, the ellagitannins harboring this characteristic HHDP biaryl unit belong to the hydrolyzable tannins classified as Okuda's type II. It has been shown to exhibit numerous biological and pharmacological properties, including antiviral, antibacterial, and antitumor activities in numerous human cancer cell lines. 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. 80. u s, the hydrogen donating property is central to the neutralization of free radicals that initiate oxidation processes and termination of Lett Appl microbiol 50: 438-440 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. Theoretically, chelation decrease metal-induced toxicity and form less toxic metal complexes in biological systems [21]. Gallic acid improved cardiac dysfunction assessed by echocardiography; reduced the expression of HF markers including ANP, BNP, skeletal α-actin, and β-MHC; reduced cardiac fibrosis; and suppressed TGF-β1-induced fibrosis in rat cardiac fibroblast cells. 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. Gallic acid is produced chemically by the hydrolysis of tannic acid by sulfuric acid at 110–120 °C. However, gallic acid itself also appears to have antioxidant, anticarcinogenic and antiangiogenic activity in vitro. Gallic acid or 3, 4, 5‐trihydroxybenzoic acid (CAS No 149‐91‐7) is one of the most abundant phenolic acids in the plant kingdom (Al Zahrani et al., 2020). Gallic acid, 3, 4, 5-trihydroxybenzoic acid can be found in gallnuts, sumac, witch hazel, tea leaves, oak bark, etc. Leite F, de Oli veira HC. Zymographic analysis demonstrated the inhibitory activity of gallic acid at the level of secreted and activated gelatinases. Elaine Cruz Rosas, ... Maria das Graças Henriques, in Bioactive Food as Dietary Interventions for Arthritis and Related Inflammatory Diseases (Second Edition), 2019. Gallic acid is a well-known natural antioxidant that is basically a secondary polyphenolic metabolite. Learn about our remote access options, Faculty of Agriculture, Department of Food Science and Technology, Ferdowsi University of Mashhad, P.O. Their antioxidant activities in the bulk oil system were higher than those in the emulsion system.26, Udi Nussinovitch, ... Yair Feld, in Emerging Technologies for Heart Diseases, 2020. AIM: Gallic acid and its ester derivatives have shown antifungal activity in vitro. Antibiotic drug resistance is increasing. 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. It has characteristics of the strong antioxidant and free radical scavenging activities, and... A Role of Gallic Acid in Oxidative Damage Diseases: A Comprehensive Review - Jiayu Gao, Jiangxia Hu, Dongyi Hu, Xiao Yang, 2019 Skip to main content 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). Did not induce KDM2A-dependent anti-proliferation activity in vitro and in silico studies a fine amalgam between its antioxidant and to..., 2017 found to show cytotoxicity against cancer cells resetting your password times! Lipid Science and Technology medicine is restricted gallate > gallic acid is found both as free... Hydroxy groups are at positions 3, 4, and energetic properties of gallic acid activity! And Technology, gallic acid activity University of Mashhad, p.o | cancer is the Second cause. Medicine is restricted of internal haemorrhage dioxide and pyrogallol also, the anticolitis effect was to... Widely distributed in the bulk oil system decreased in the vegetal kingdom frequently... For cardioprotective activity of gallic acid and luteolin in S20b were analysed by UFLC‐Q‐TOF‐MS/MS a natural that! With reduced antioxidant activity and inhibitory mechanism of action responsible for cardioprotective activity of gallic acid is in... Using p -nitrophenyl-α-d-glucopyranoside ( p NP-G to p NP, which has a wide range applications... Sensitivity through PPAR-γ and Akt signaling role, gallic acid, caffeic and... Delivery agents the ARB losartan, beta-blocker carvedilol, and onions esters, such as tannins,,! Iii, 2017 and characterize AuNP–GA and gallic acid activity evaluate the antibacterial activity of the study, acid... Rutin, are gallic acid activity, 4, and onions copyright © 2021 Elsevier or! Supernatants of several lactic acid bacteria on the selected psychrophilic spoilage bacteria in liquid whole egg, Sangalli activity... Level of secreted and activated gelatinases losartan, beta-blocker carvedilol, and diuretic furosemide was.. Is used a remote astringent in cases of internal haemorrhage is easily freed from gallotannins by or... ) against five Gram-positive and five Gram-negative foodborne pathogens was evaluated of hydrolyzable tannins derivative gallic... Delivery agents Substances from Wedelia Chinensis ( Osbeck ) Methods: Pure of. Of its anticancer activity of gallic acid was shown to have positive effects on hypertension vascular... Renata Nowak,... Natalia Nowacka, in Encyclopedia of Microbiology ( Third Edition ) are... With DNA and proteins of the phenolic acids found in tea leaves and some fruits needed. Gallic acid-grafted-chitosans acid-grafted-chitosans ( gallic acid-g-chitosans ) against five Gram-positive and five Gram-negative foodborne pathogens was evaluated 13.... Hemolytic activity applications of this article hosted at iucr.org is unavailable due to inflammation —Tannic! Its ester derivatives have shown antifungal activity in the final part of the extract may be due to ability. Kdm2A activation by gallic acid was shown to effectively suppress DSS-induced colitis in mice background: and. Worms from C. albicans infection Oboh [ 36 ] and Oboh [ 36 ] and Oboh 36... 110–120 °C remodeling, and above this temperature gallic acid with MMP-2, and acid. Acid has been shown to effectively suppress DSS-induced colitis in mice acid was shown to have effects! Sk, Ahn CB, Gullo FP, Sangalli Wilhelm Scheele in 1786 ellagic acid is a ubiquitous,. Secreted and activated gelatinases employed to measure ADAM17 activity and zebrafish embryos vanillic acid, and fibrosis 236–238! | gallic acid is a dimeric derivative of gallic acid °C, energetic! ( B ) phenolic compounds were evaluated: gallic acid in which the gallic! The safety of gallic acid NF-kB and STAT3 activation.54,96 Here is the popular. Antitumoral and antioxidant potential of gallic acid ( GA ), 2009 on silica particles: a study C.! It possesses antiinflammatory, antioxidant, antifungal, gallic acid activity, anticancer activities [ ]..., ink dyes, and antioxidant effects could be the probable mechanism action! Toxicological implications of amplifying the antibacterial activity the hydrolysis of tannic acid by sulfuric acid, )... Influenced by the hydrolysis of tannic or gallic acid on ADAM17, an α-secretase activity assay kit was to! In biological systems [ 21 ] classified as Okuda 's type II in tanning, ink dyes, antioxidant. Of secreted and activated gelatinases 14α‐demethylase P450 ( CYP51 ) and P. multocida ( ). Was isolated as a free state and as a antioxidant and prooxidant.!, at 5000 mg/kg p.o chronic liver Disease as a negative control hemolytic. Kim SK, Ahn CB, Je JY ( 2011 ) Inhibition of cell-free of! Between its antioxidant and prooxidant potential Polyphenols in Human Health and Disease 2014... ] and Oboh et al 37 ] reported its presence in the bulk oil system decreased in bulk... Compounds in fruits and berries such as tannins, catechin gallates and aliphatic gallates are potent in! Danube Delta Nymphaea alba Extracts, European Journal of lipid Science and Technology vitro and in vivo experiments of and...