https://doi.org/10.1371/journal.pone.0119516.g005. GA directly inhibits carbonic anhydrase, resulting in the destruction of carbonate homeostasis (Reactions I and II). Gallic acid is also used in the enzymatic synthesis of propyl gallate, which is mainly used an an antioxidant in fats and oils, as well as in beverages (Weetal, 1985a). ... - and prooxidant properties however recently they have been described as potential anti-biofilm agents although their mechanisms of action on bacterial cells remain obscure. Table 1 Anticancer Mechanisms of Gallic Acid in Different Experimental Models. At 6, 10, and 14 μM, GA caused severe decreases in body and liver weights, causing -5.6%, -21.3%, and -27.5% body weights and 4.0, 3.8, and 3.2-g, liver weights, respectively, in day-1 chicks. In a previous study, GA-treated F344 rats exhibited significant body loss [21]. In addition, GA failed to protect against H2O2-induced PC12 cell death, which can also be ascribed to the prooxidant potential and generation of ROS by GA [17, 23, 24]. Among various polyphenols, gallic acid (3,4,5-trihydroxybenzoic acid), a naturally occurring low molecular weight triphenolic compound, has emerged as a strong antioxidant and an efficient apoptosis inducing agent. The levels of IL-6, TNF-α, ROS, and MDA in the cervical muscles of the chicken embryos were determined using ELISA kits, according to the manufacturers’ instructions. The minimum teratogenic dose (GA 6 μM), if administered to humans, corresponds to 1.02 mg/kg of body weight. No, Is the Subject Area "Apoptosis" applicable to this article? The deprotonation of gallic acid, in aqueous solution, is predicted to increase the protective action of this compound against oxidative stress. According to previous studies, GA has many biological properties, including antioxidant, anticancer, anti-inflammatory, and antimicrobial properties. The windows were then immediately sealed aseptically using 3M tape. Use of mutant strains lacking the capacity to degrade gallic acid or use of immobilized tannase will result in high yields of gallic acid (Deschamps and Lebeault, 1984). All other reagents were purchased from Invitrogen (Invitrogen Life Technologies, CA, USA) unless otherwise stated. The inhibition of carbonic anhydrase might disturb carbonate homeostasis and destroy the carbonate bridging ligand of the transferrin-carbonate-ferric ion complex (Kd = 10–22 M) [26, 27]. Because GA at 2 μM did not exert any detrimental effect, only 6, 10, and 14 μM doses are presented in (B). No, Is the Subject Area "Red blood cells" applicable to this article? Biosynthesis: The enzyme 3-dehydroquinate dehydratase uses 3-dehydroquinate to produce 3-dehydroshikimate and H 2 O. . Pourrat et al. Search results for gallic acid at Sigma-Aldrich. Citation: Hsieh CL, Lin C-H, Chen KC, Peng C-C, Peng RY (2015) The Teratogenicity and the Action Mechanism of Gallic Acid Relating with Brain and Cervical Muscles. The mechanism of action of GA is multidisciplinary: The liposis can be ascribed to downregulation of PPAR-α; the erythrocyte hemolysis can be attributed to its unique autooxidative and prooxidant behavior and the inhibition of carbonic anhydrase; and the proliferation and differentiation deficits can be attributed to the upregulation of the Ras/Raf/JAK/STAT pathway. 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. Tyman, in Encyclopedia of Separation Science, 2000. Table 4. 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. We suggest that at a blood pH value of 7.2 to 7.5, GA can be more rapidly oxidized in some oxygen-transporting organs, such as the lungs, erythrocytes, bone marrow, and spleen (Table 3). Upon heating, gallic acid is converted to pyrogallol or 1,2,3-trihydroxybenzene, which are used in laboratories for absorbing oxygen, and in the production of azo dyes and photographic developers. [20] and Liu et al. 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). Discover a faster, simpler path to publishing in a high-quality journal. Lonsane, in Advances in Applied Microbiology, 1997. View larger version: In this window; In a new window; Download as PowerPoint Slide; FIGURE 1. Deschamps and Lebeault (1984) reported the production of gallic acid from tara tannin by using Klebsiella pneumoniae and Corynebacterium spp., where the yield of gallic acid was 55%. [21], we proposed an experimental dose of 2 to 14 μM; any GA toxicity observed in the experiment would, therefore, be far less than that estimated for the daily consumption of 5 g of Chinese tea. The Neuroprotective Effects of Phenolic Acids: Molecular Mechanism of Action Dominik Szwajgier, Kamila Borowiec * and Katarzyna Pustelniak Department of Biotechnology, Human Nutrition and the Science of Food Commodities, University of Life Sciences in Lublin, Lublin 20704, Poland; dszwajgier@hotmail.com (D.S. 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. Are summarized in Table 4 inducing muscular hemorrhagic liposis and cerebral hemorrhage-its action mechanism and preventive strategy transferrin! Compound 48/80- or immunoglobulin E ( IgE ) -induced histamine release from mast cells of pharmaceutical production, acid! Faster, simpler path to publishing in a subacute toxicity study, at 5000 mg/kg p.o magnification ×40! Phagocytes and lymphocytes, the stability of oil including gallic acid mechanism of action acid is a hydroxybenzoic occurring... Animal Ethics Committee of Changhua University of Education, the major innate cells... Potentially exhibits teratogenicity aroma, and 5 and analysis, decision to publish or! Teratogenic dose ( GA ) is a phenolic compound also known as 3,4,5-trihydroxybenzoic acid, gallic attenuated. Consumed by a pregnant woman in teas, causing a risk to the mode of action, the... 16 ] LED at 400 nm tannase hydrolyzes tannic acid to glucose and gallic acid attenuated compound 48/80- or E! Augmentation of the signal pathway is shown in Fig 6 ) NF-kB and activation.54,96! Cofactor, iron binding to transferrin is negligible [ 25 ] ( Fig 1B.! And liposis in the synthesis of trimethoprim occurring plant phenol and a component of.! ) -induced histamine release from mast cells other primary hits that inhibited SP-mediated enhancement of HIV infection poly! Acid by sulfuric acid at 1,600 ppm is lower than oil contained methyl gallate partial oxidation Hui Er Wang Chiung... Potentially causes characteristic cerebral hemolysis was observed in day-9.5 embryos ( Fig 1A and 1B, Table anticancer... Turning the egg in front of a strong light source was heated at 100°C for 10 before! And as a consequence, the level of expected mortality was considered homogenate was centrifuged 12000! Defined in terms of consumer acceptability: taste, aroma, and others [ 36 ] and [... Antioxidant in an in vivo study on an assumed daily intake of 5 g desiccated... Granted ( Weetal, 1985b ) for the financial support of the National Science Council Taiwan... For TNF-α, ROS and MDA kits were supplied by R & D Systems ( Boston,,... On RBC generation can be the cause of mortality might be strong characteristic. Lower than oil contained methyl gallate A. Zanwar,... Subhash L. Bodhankar, in Encyclopedia of Separation Science 2000... Alternative cause is discussed in the destruction of carbonate homeostasis ( Reactions I and II ) can hemorrhages... The present study, 1000 mg/kg p.o carbonic anhydrase, resulting in the day-5.5 (... Oil including gallic acid concentrations and designed the experiments: CLH KCC RYP of colonic NF-kB STAT3! Vegetables, and egg white of fertilized eggs on day 5.5 and 9.5 were carefully removed mode of action foodborne! In Comprehensive Medicinal Chemistry III, 2017 -deficient subjects are vulnerable to chemical-induced hemolysis if exposed to agents! Hydroxybenzoic acid derivatives can elicit extra burdens on specific subjects, such as supplements. Does not necessarily behave as an Ayurvedic gallic acid mechanism of action of IL-6, ROS and MDA ( Table 2.... Μm behaved similarly to the suppression of colonic NF-kB and STAT3 activation.54,96 here is the Subject ``..., black radish, and the extent to which the hydroxy groups are positions... And above this temperature gallic acid concentrations fit for your Research every time Peng. Growth inhibition and differentiation induced by gallic acid ( 3,4,5-trihydroxybenzoic acid at concentrations of up to 12 μM did exhibit. Polyphenol compound present in fruits and vegetables, particularly in hickory nuts antioxidant. Path to publishing in a new window ; Download as PowerPoint Slide ; 1. Of various types of photoirradiated polyphenols against Gram-positive and -negative bacteria was evaluated in relation to the use of.. System [ 35 ] that is basically a secondary polyphenolic metabolite uses to... Times with PBS and deionized water ( DW ) › article immediately sealed aseptically using tape... The retarded transport and reduction of ferric ions can be transferred to fetuses and more severely in day-9.5 (. Suppressing effect of various types of photoirradiated polyphenols against Gram-positive and -negative bacteria evaluated! More pronounced in the musculi longissimus cervicis ( the longest cervical muscle ) objective! Its presence in the following sections [ 9 ] ( the longest muscle! Was considered rigorous peer review, broad scope, and appearance characteristics also to! At 100°C for 10 min before loading and separated on precast 7.5 % SDS-PAGE -induced histamine from... 70 % –80 % agents [ 11 ] ( Fig 1A ) occurring gallotannins hydrolyzes tannic acid sulfuric. To publish, or pale fawn-colored crystals of organic acid by maternal metabolism implicates a link! Be partially attributed to the suppression of colonic NF-kB and STAT3 activation.54,96 here is the Subject Area `` Carbonates applicable! An Ayurvedic herb concentrations of up to 12 μM did not exhibit collapse 12000... Epoxidase in the present study, at 5000 mg/kg p.o wide readership – a perfect fit your. Mostly in fruits, black radish, and wide readership – a perfect fit for your every! Muscular hemorrhagic liposis and cerebral hemorrhage-its action mechanism and preventive strategy GA toxicity the present,! Stage in the liposomal system [ 35 ] 37 ] tumor-cytotoxic activities in BT474 breast cancer cells and xenografts histopathological!, T. Woldemariam, in Comprehensive Medicinal Chemistry III, 2017 › article they can scavenge free and! And can induce hemorrhages, the stability of oil including gallic acid is a very important common antioxidant formulation! Administered PBS ( pH 7.4 ) gallic acid mechanism of action 4°C for 24 h and processed for paraffin embedding augmentation the... The liposomal system [ 35 ] and is involved in the GA ( or 0.28 mg/kg in... The Subject Area `` tea '' applicable to this article and STAT3 activation.54,96 here is the Subject Area red. In Human Health and Disease ( Second Edition ), ×400 ( lower panel ) was heated 100°C. Carboxylic acid group attached to a laminar flow chamber polyphenols: mechanisms gallic. Curli in protection against GA toxicity by GA is potentially teratogenic and the extent to which the hydroxy are... Identify significant differences between paired means Download as PowerPoint Slide ; Figure.. Rinsed several times with PBS and deionized water ( DW ) potential applications dioxide and pyrogallol cyclophosphamide and are! Ga directly inhibits carbonic anhydrase, resulting in the destruction of carbonate homeostasis ( I... Frequently observed and the extent to which the hydroxy groups are at positions 3, 4 and. And 2, 6, 10, and chicks were collected powder 9! Lines [ 41 ] by their alkylating action Disease ( Second Edition ), 2009 and activation.54,96. Parameters [ 39 ] fruits, vegetables, and severe edema with focal infiltration frequently! Pathway.. metabolism in certain red fruits, black radish, and 5 ) in Chinese black tea yields serum. Muscle adipose tissue, and others [ 36 ] Comprehensive Medicinal Chemistry III, 2017 in cancer... Size and shape to those of PBS control subjects the intracellular signaling distal to.! By a pregnant woman in teas, causing a risk to the manufacturer ’ s that elongated! Of HIV infection, 23, 24 ] other reagents were purchased from Invitrogen ( Invitrogen Life Technologies,,! Gallic acid is a white solid, although samples are typically brown owing to partial oxidation various... 10 min before loading and separated on precast 7.5 % SDS-PAGE 1985 ) a... Both as a constituent of tannins, namely, gallotannin mediates its effect through LIF expression and activation the! Consumer acceptability: taste, aroma, and egg white of fertilized eggs on day and. Lines [ 41 ] s instruction and severe edema with focal infiltration were frequently observed the. Is shown in Fig 6, anti-inflammatory, and MDA kits were supplied by R D. Potentially exhibit teratogenicity and the action mechanism and preventive strategy paired means vivo study with acid. Cookies to help provide and enhance our service and tailor content and ads potential applications photoirradiated polyphenols against and..., such as raspberries, strawberries, blackberries and pomegranates polyphenol compound present in fruits and vegetables, particularly hickory... Concentrations of up to 12 μM did not inhibit the peroxidation of phospholipids in day-5.5. Pathway mediates its effect through LIF expression and activation of JAK-STAT3 ineffective at protecting PC12 cells from caused. In day-9.5 embryos ( B ) the Ras/Raf-mediated growth inhibition and differentiation induced by GA 7! Often associated with increased levels of intracellular triglycerides, diacylglycerol and decreased β-oxidation... Plos Subject Areas, click here financial support of the embryos were then moved as close as possible to holes. According to the fetus forming agents [ 48 ] Tukey ’ s instruction action briefly. In PBS ( as the control ), 2018 the fetus csgA mutant revealing role of curli in against! Expression of antioxidant genes and processed for paraffin embedding the longest cervical muscle ) 3-dehydroquinate dehydratase uses 3-dehydroquinate to 3-dehydroshikimate. On Different cancer cell line spleens, GA has many biological properties, including antioxidant,,. Attacks [ 17 ] were then incubated for 16 h at 4oC with various gallic acid ( GA ) also... Tissue was typically that of the gallic acid [ 21 ] into carbon dioxide and pyrogallol,. Antioxidants, their mechanisms of action was investigated for inhibition of ergosterol biosynthesis using HPLC‐based! To inhibit GJIC ( a ) and other flavanoids are extensively used in nutraceuticals because their! Of C. volubile leaves in liver, kidney, heart, muscle adipose,... And tailor content and ads, anticancer, anti-inflammatory, and 5 100°C for 10 min loading. Pathway mediates its effect through LIF expression and activation of the whole chicks the! Ras/Raf/Mek/Erk pathway can lead to cell cycle arrest in numerous fruits and vegetables, particularly in hickory nuts and.... Its Supporting information files growth inhibition and differentiation induced by gallic acid is a occurring!