Epigallocatechin-gallate

Epigallocatechin Gallate is a phenolic antioxidant found in a number of plants such as green and black tea (the Most Abundant Catechin in Green Tea). It inhibits cellular oxidation and prevents free radical damage to cells. It is under study as a potential cancer chemopreventive agent. (NCI) One Hydroxy more than Epicatechin-gallate

General

Type : Derivative of Gallate, Benzoate, Natural, Polyphenol, Chromen

Chemical_Nomenclature : [(2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromen-3-yl] 3,4,5-trihydroxybenzoate

Canonical SMILES : C1C(C(OC2=CC(=CC(=C21)O)O)C3=CC(=C(C(=C3)O)O)O)OC(=O)C4=CC(=C(C(=C4)O)O)O

InChI : InChI=1S\/C22H18O11\/c23-10-5-12(24)11-7-18(33-22(31)9-3-15(27)20(30)16(28)4-9)21(32-17(11)6-10)8-1-13(25)19(29)14(26)2-8\/h1-6,18,21,23-30H,7H2\/t18-,21-\/m1\/s1

InChIKey : WMBWREPUVVBILR-WIYYLYMNSA-N

Other name(s) : EGCG  ||  Epigallocatechin gallate  ||  Epigallocatechin 3-gallate  ||  Epigallocatechin-3-gallate  ||  epigallocatechin-3-O-gallate  ||  (-)-Epigallocatechin-3-gallate  ||  (-)-Epigallocatechin gallate  ||  CHEBI:4806  ||  CHEMBL297453  ||  Gallic acid, 3-ester with epigallocatechol, (-)-


MW : 458.4

Formula : C22H18O11

CAS_number : 989-51-5

PubChem : 65064

UniChem : WMBWREPUVVBILR-WIYYLYMNSA-N

Target

Families : Epigallocatechin-gallate ligand of proteins in family
Arylacetamide_deacetylase

Protein :
human-AADAC

References (22)

Title : Structural characterization and antioxidant property of enzymatic-transesterification derivatives of (-)-epigallocatechin-3-O-gallate and vinyl laurate - Jiang_2021_J.Food.Sci__
Author(s) : Jiang C , Wang L , Huang X , Zhu S , Ma C , Wang H
Ref : J Food Sci , : , 2021
Abstract :
PubMedSearch : Jiang_2021_J.Food.Sci__
PubMedID: 34553787

Title : Epigallocatechin-3-gallate improves chronic alcohol-induced cognitive dysfunction in rats by interfering with neuro-inflammatory, cell death and oxido-nitrosative cascade - Uniyal_2021_Metab.Brain.Dis__
Author(s) : Uniyal A , Akhilesh , Tiwari V , Gadepalli A , Ummadisetty O
Ref : Metabolic Brain Disease , : , 2021
Abstract :
PubMedSearch : Uniyal_2021_Metab.Brain.Dis__
PubMedID: 34386880

Title : Epigallocatechin-3-Gallate Provides Protection Against Alzheimer's Disease-Induced Learning and Memory Impairments in Rats - Nan_2021_Drug.Des.Devel.Ther_15_2013
Author(s) : Nan S , Wang P , Zhang Y , Fan J
Ref : Drug Des Devel Ther , 15 :2013 , 2021
Abstract :
PubMedSearch : Nan_2021_Drug.Des.Devel.Ther_15_2013
PubMedID: 34012254

Title : Role of human AADAC on hydrolysis of eslicarbazepine acetate and effects of AADAC genetic polymorphisms on hydrolase activity - Hirosawa_2021_Drug.Metab.Dispos__
Author(s) : Hirosawa K , Fukami T , Tashiro K , Sakai Y , Kisui F , Nakano M , Nakajima M
Ref : Drug Metabolism & Disposition: The Biological Fate of Chemicals , : , 2021
Abstract :
PubMedSearch : Hirosawa_2021_Drug.Metab.Dispos__
PubMedID: 33446525
Gene_locus related to this paper: human-AADAC

Title : Therapeutic effects of biochanin A, phloretin, and epigallocatechin-3-gallate in reducing oxidative stress in arsenic-intoxicated mice - Singh_2021_Environ.Sci.Pollut.Res.Int__
Author(s) : Singh G , Thaker R , Sharma A , Parmar D
Ref : Environ Sci Pollut Res Int , : , 2021
Abstract :
PubMedSearch : Singh_2021_Environ.Sci.Pollut.Res.Int__
PubMedID: 33410021

Title : Protective Role of Epigallocatechin Gallate in a Rat Model of Cisplatin-Induced Cerebral Inflammation and Oxidative Damage: Impact of Modulating NF-kappaB and Nrf2 - Arafa_2020_Neurotox.Res_37_380
Author(s) : Arafa MH , Atteia HH
Ref : Neurotox Res , 37 :380 , 2020
Abstract :
PubMedSearch : Arafa_2020_Neurotox.Res_37_380
PubMedID: 31410684

Title : Dipeptidyl Peptidase-4 Is a Target Protein of Epigallocatechin-3-Gallate - Hou_2020_Biomed.Res.Int_2020_5370759
Author(s) : Hou H , Wang Y , Li C , Wang J , Cao Y
Ref : Biomed Res Int , 2020 :5370759 , 2020
Abstract :
PubMedSearch : Hou_2020_Biomed.Res.Int_2020_5370759
PubMedID: 32104696

Title : Novel Hybrid Molecules Based on (-)-Epigallocatechin Gallate as Potent Anti-adipogenic Agents - Jeong_2020_Chem.Pharm.Bull.(Tokyo)_68_1155
Author(s) : Jeong GH , Cho JH , Jo C , Park S , Kim SB , Kim TH
Ref : Chem Pharm Bull (Tokyo) , 68 :1155 , 2020
Abstract :
PubMedSearch : Jeong_2020_Chem.Pharm.Bull.(Tokyo)_68_1155
PubMedID: 33268647

Title : Membrane order and ionic strength modulation of the inhibition of the membrane-bound acetylcholinesterase by epigallocatechin3gallate - Salazar_2019_Biochim.Biophys.Acta.Biomembr_1861_170
Author(s) : Salazar PB , Dupuy FG , de Athayde Moncorvo Collado A , Minahk CJ
Ref : Biochimica & Biophysica Acta Biomembr , 1861 :170 , 2019
Abstract :
PubMedSearch : Salazar_2019_Biochim.Biophys.Acta.Biomembr_1861_170
PubMedID: 30463700

Title : (-)Epigallocatechin-3-gallate attenuates anesthesiainduced memory deficit in young mice via modulation of nitric oxide expression - Ding_2018_Mol.Med.Rep_18_4813
Author(s) : Ding L , Gao X , Hu J , Yu S
Ref : Mol Med Rep , 18 :4813 , 2018
Abstract :
PubMedSearch : Ding_2018_Mol.Med.Rep_18_4813
PubMedID: 30320383

Title : Differential inhibition of human erythrocyte acetylcholinesterase by polyphenols epigallocatechin-3-gallate and resveratrol. Relevance of the membrane-bound form - Salazar_2017_Biofactors_43_73
Author(s) : Salazar PB , de Athayde Moncorvo Collado A , Canal-Martinez V , Minahk CJ
Ref : Biofactors , 43 :73 , 2017
Abstract :
PubMedSearch : Salazar_2017_Biofactors_43_73
PubMedID: 27591048

Title : Epigallocatechin-3-gallate attenuates cerebral cortex damage and promotes brain regeneration in acrylamide-treated rats - He_2017_Food.Funct_8_2275
Author(s) : He Y , Tan D , Mi Y , Zhou Q , Ji S
Ref : Food Funct , 8 :2275 , 2017
Abstract :
PubMedSearch : He_2017_Food.Funct_8_2275
PubMedID: 28561817

Title : Effect of epigallocatechin-3-gallate on acrylamide-induced oxidative stress and apoptosis in PC12 cells - He_2017_Hum.Exp.Toxicol_36_1087
Author(s) : He Y , Tan D , Mi Y , Bai B , Jiang D , Zhou X , Ji S
Ref : Hum Exp Toxicol , 36 :1087 , 2017
Abstract :
PubMedSearch : He_2017_Hum.Exp.Toxicol_36_1087
PubMedID: 27920337

Title : A green tea polyphenol epigallocatechin-3-gallate enhances neuroregeneration after spinal cord injury by altering levels of inflammatory cytokines - Machova_2017_Neuropharmacol_126_213
Author(s) : Machova Urdzikova L , Ruzicka J , Karova K , Kloudova A , Svobodova B , Amin A , Dubisova J , Schmidt M , Kubinova S , Jhanwar-Uniyal M , Jendelova P
Ref : Neuropharmacology , 126 :213 , 2017
Abstract :
PubMedSearch : Machova_2017_Neuropharmacol_126_213
PubMedID: 28899730

Title : Fast identification of lipase inhibitors in oolong tea by using lipase functionalised Fe3O4 magnetic nanoparticles coupled with UPLC-MS\/MS - Zhu_2015_Food.Chem_173_521
Author(s) : Zhu YT , Ren XY , Yuan L , Liu YM , Liang J , Liao X
Ref : Food Chem , 173 :521 , 2015
Abstract :
PubMedSearch : Zhu_2015_Food.Chem_173_521
PubMedID: 25466054

Title : Molecular Interactions between (-)-Epigallocatechin Gallate Analogs and Pancreatic Lipase - Wang_2014_PLoS.One_9_e111143
Author(s) : Wang S , Sun Z , Dong S , Liu Y
Ref : PLoS ONE , 9 :e111143 , 2014
Abstract :
PubMedSearch : Wang_2014_PLoS.One_9_e111143
PubMedID: 25365042

Title : Green tea (-)epigallocatechin-3-gallate reverses oxidative stress and reduces acetylcholinesterase activity in a streptozotocin-induced model of dementia - Biasibetti_2013_Behav.Brain.Res_236_186
Author(s) : Biasibetti R , Tramontina AC , Costa AP , Dutra MF , Quincozes-Santos A , Nardin P , Bernardi CL , Wartchow KM , Lunardi PS , Goncalves CA
Ref : Behavioural Brain Research , 236 :186 , 2013
Abstract :
PubMedSearch : Biasibetti_2013_Behav.Brain.Res_236_186
PubMedID: 22964138

Title : Impact of epigallo catechin-3-gallate on acetylcholine-acetylcholine esterase cycle in aged rat brain - Srividhya_2012_Neurochem.Int_60_517
Author(s) : Srividhya R , Gayathri R , Kalaiselvi P
Ref : Neurochem Int , 60 :517 , 2012
Abstract :
PubMedSearch : Srividhya_2012_Neurochem.Int_60_517
PubMedID: 22366543

Title : (-)-Epigallocatechin-3-gallate inhibits pancreatic lipase and reduces body weight gain in high fat-fed obese mice - Grove_2012_Obesity.(Silver.Spring)_20_2311
Author(s) : Grove KA , Sae-tan S , Kennett MJ , Lambert JD
Ref : Obesity (Silver Spring) , 20 :2311 , 2012
Abstract :
PubMedSearch : Grove_2012_Obesity.(Silver.Spring)_20_2311
PubMedID: 21633405
Gene_locus related to this paper: human-PNLIP

Title : Tea polyphenol (-)-epigallocatechin-3-gallate inhibits nicotine- and estrogen-induced alpha9-nicotinic acetylcholine receptor upregulation in human breast cancer cells - Tu_2011_Mol.Nutr.Food.Res_55_455
Author(s) : Tu SH , Ku CY , Ho CT , Chen CS , Huang CS , Lee CH , Chen LC , Pan MH , Chang HW , Chang CH , Chang YJ , Wei PL , Wu CH , Ho YS
Ref : Mol Nutr Food Res , 55 :455 , 2011
Abstract :
PubMedSearch : Tu_2011_Mol.Nutr.Food.Res_55_455
PubMedID: 21370452

Title : Epigallocatechin-3-gallate ameliorates alcohol-induced cognitive dysfunctions and apoptotic neurodegeneration in the developing rat brain - Tiwari_2010_Int.J.Neuropsychopharmacol_13_1053
Author(s) : Tiwari V , Kuhad A , Chopra K
Ref : Int J Neuropsychopharmacol , 13 :1053 , 2010
Abstract :
PubMedSearch : Tiwari_2010_Int.J.Neuropsychopharmacol_13_1053
PubMedID: 20529413

Title : Enhanced anti-influenza A virus activity of (-)-epigallocatechin-3-O-gallate fatty acid monoester derivatives: effect of alkyl chain length - Mori_2008_Bioorg.Med.Chem.Lett_18_4249
Author(s) : Mori S , Miyake S , Kobe T , Nakaya T , Fuller SD , Kato N , Kaihatsu K
Ref : Bioorganic & Medicinal Chemistry Lett , 18 :4249 , 2008
Abstract :
PubMedSearch : Mori_2008_Bioorg.Med.Chem.Lett_18_4249
PubMedID: 18547804