Epigallocatechin-gallate

General

Type : Derivative of Gallate, Benzoate, Natural, Polyphenol

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 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

Structures : No structure

Families : AlphaBeta_hydrolase, Plant_carboxylesterase

References (26)

Title : New insights into the function of plant tannase with promiscuous acyltransferase activity - Chen_2022_Plant.J__
Author(s) : Chen Y , Jiang C , Yin S , Zhuang J , Zhao Y , Zhang L , Jiang X , Liu Y , Gao L , Xia T
Ref : Plant J , : , 2022
Abstract :
PubMedSearch : Chen_2022_Plant.J__
PubMedID: 36534122
Gene_locus related to this paper: camsi-CsTA

Title : Genome-Wide Identification of Tannase Genes and Their Function of Wound Response and Astringent Substances Accumulation in Juglandaceae - Wang_2021_Front.Plant.Sci_12_664470
Author(s) : Wang J , Wang K , Lyu S , Huang J , Huang C , Xing Y , Wang Y , Xu Y , Li P , Hong J , Xi J , Si X , Ye H , Li Y
Ref : Front Plant Sci , 12 :664470 , 2021
Abstract :
PubMedSearch : Wang_2021_Front.Plant.Sci_12_664470
PubMedID: 34079571
Gene_locus related to this paper: camsi-CsTA

Title : Degradation of epigallocatechin and epicatechin gallates by a novel tannase Tan(Hcw) from Herbaspirillum camelliae - Lei_2021_Microb.Cell.Fact_20_197
Author(s) : Lei J , Zhang Y , Ni X , Yu X , Wang X
Ref : Microb Cell Fact , 20 :197 , 2021
Abstract :
PubMedSearch : Lei_2021_Microb.Cell.Fact_20_197
PubMedID: 34641872
Gene_locus related to this paper: 9burk-TanHcw

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 : Discovery and characterization of tannase genes in plants: roles in hydrolysis of tannins - Dai_2020_New.Phytol_226_1104
Author(s) : Dai X , Liu Y , Zhuang J , Yao S , Liu L , Jiang X , Zhou K , Wang Y , Xie D , Bennetzen JL , Gao L , Xia T
Ref : New Phytol , 226 :1104 , 2020
Abstract :
PubMedSearch : Dai_2020_New.Phytol_226_1104
PubMedID: 32061142
Gene_locus related to this paper: camsi-a0a5b9g8c2 , jugre-JrTA , fraan-FaTA , vitvi-VvTA , citcl-CcTA , dioka-DkTA , camsi-CsTA

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