EPIGALLOCATECHIN GALLATE

First approved in 2012

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C22H18O11
Molecular Weight	458.3717
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC1=CC2=C(C[C@@H](OC(=O)C3=CC(O)=C(O)C(O)=C3)[C@H](O2)C4=CC(O)=C(O)C(O)=C4)C(O)=C1

InChI

InChIKey=WMBWREPUVVBILR-WIYYLYMNSA-N

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

HIDE SMILES / InChI

Molecular Formula	C22H18O11
Molecular Weight	458.3717
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21827739 | https://clinicaltrials.gov/ct2/show/NCT00799890 | https://clinicaltrials.gov/ct2/show/NCT02008721

Epigallocatechin-3-gallate (EGCG), the major polyphenol from green tea, has the potential to impact a variety of human diseases. EGCG functions as a powerful antioxidant, preventing oxidative damage in healthy cells, but also as an antiangiogenic and antitumor agent and as a modulator of tumor cell response to chemotherapy. It was shown, that EGCG can inhibit 5-cytosine DNA methyltransferase (DNMT) activity and reactivate methylation-silenced genes in cancer cells and another of the probable mechanisms by EGCG exercise their anti-tumor property is through the suppression of the NFκB signaling pathway. EGCG has emerged as a potential neuroprotective agent for the treatment of neurological disorders associated with harmful effects of reactive oxygen species. The neuroprotective mechanism of action is probably based on several factors, including EGCG's modulation of several signal transduction pathways, its influence on the expression of genes regulating cell survival or programmed cell death, as well as its modulation of mitochondrial function. A phase II/III trial of oral Sunphenon epigallocatechin-3-gallate in patients with progressive multiple sclerosis has been completed. In addition, EGCG was in phase III clinical trials for the treatment of multiple system atrophy and for patients with Duchenne Muscular Dystrophy ((DMD). DMD is the most frequent neuromuscular condition to occur in childhood and youth.

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
DNA (cytosine-5)-methyltransferase 1 10 Target ID: P26358 Gene ID: 1786.0 Gene Symbol: DNMT1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/14633667	Inhibitor 8297		6.89 µM [Ki]
NF-kappa B signaling pathway 84 Target ID: map04064 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21827739	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Multiple sclerosis 104 Sources: https://clinicaltrials.gov/ct2/show/NCT00799890	Primary	Phase III 656	Unknown Approved Use Unknown
Multiple system atrophy 1 Sources: https://clinicaltrials.gov/ct2/show/NCT02008721	Primary	Phase III 656	Unknown Approved Use Unknown
Duchenne muscular dystrophy 19 Sources: https://clinicaltrials.gov/ct2/show/NCT01183767	Primary	Phase III 656	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Green tea and cancer chemoprevention.	1999 Jul 16	10518005
A new concept of tumor promotion by tumor necrosis factor-alpha, and cancer preventive agents (-)-epigallocatechin gallate and green tea--a review.	2000	10757128
Developing a dynamic pharmacophore model for HIV-1 integrase.	2000 Jun 1	10841789
Anti-herpes simplex virus type-1 flavonoids and a new flavanone from the root of Limonium sinense.	2000 May	10865449
Specific induction of glutathione S-transferase GSTM2 subunit expression by epigallocatechin gallate in rat liver.	2000 Sep 1	10927022
Inhibition of melanoma growth and metastasis by combination with (-)-epigallocatechin-3-gallate and dacarbazine in mice.	2001	11746506
The 'pivotal antioxidant' hypothesis for the role of flavonoids in their reduction of HO* radical-induced damage on DNA.	2001	11523599
A new function of green tea: prevention of lifestyle-related diseases.	2001 Apr	11795518
Inactivation of parvovirus B19 in coagulation factor concentrates by UVC radiation: assessment by an in vitro infectivity assay using CFU-E derived from peripheral blood CD34+ cells.	2001 Apr	11316894
Prolyl endopeptidase inhibitors from green tea.	2001 Aug	11534759
Metabolic fate of (-)-[4-(3)H]epigallocatechin gallate in rats after oral administration.	2001 Aug	11513717
The molecular interaction of human salivary histatins with polyphenolic compounds.	2001 Aug	11502198
Potent antimutagenic activity of white tea in comparison with green tea in the Salmonella assay.	2001 Aug 22	11448643
Tea catechin, (-)-epigallocatechin gallate, causes membrane depolarizations of myenteric neurons in the guinea-pig small intestine.	2001 Aug 24	11502353
Anticarcinogenic antioxidants as inhibitors against intracellular oxidative stress.	2001 Dec	11811529
Plasma concentrations of individual tea catechins after a single oral dose in humans.	2001 Dec	11780763
Effects of epigallocatechin-3-gallate on growth, epidermal growth factor receptor signaling pathways, gene expression, and chemosensitivity in human head and neck squamous cell carcinoma cell lines.	2001 Dec	11751523
The green tea polyphenol (-)-epigallocatechin gallate attenuates beta-amyloid-induced neurotoxicity in cultured hippocampal neurons.	2001 Dec 21	11811904
Apoptosis-inducing activity of high molecular weight fractions of tea extracts.	2001 Feb	11302190
Green tea polyphenol (-)-epigallocatechin-3-gallate treatment of human skin inhibits ultraviolet radiation-induced oxidative stress.	2001 Feb	11181450
Tumor gelatinases and invasion inhibited by the green tea flavanol epigallocatechin-3-gallate.	2001 Feb 15	11241252
Phase I pharmacokinetic study of tea polyphenols following single-dose administration of epigallocatechin gallate and polyphenon E.	2001 Jan	11205489
Comparative efficacy as antioxidants between ascorbic acid and epigallocatechin gallate on cells of two human lymphoblastoid lines.	2001 Jan 15	11172912
Production of hydrogen peroxide and methionine sulfoxide by epigallocatechin gallate and antioxidants.	2001 Jul-Aug	11724332
Changes in amino acid pool and utilization during apoptosis in HL-60 cells induced by epigallocatechin gallate or gallic acid.	2001 Jul-Aug	11724305
Oxygen radical absorbance capacity of the phenolic compounds in plant extracts fractionated by high-performance liquid chromatography.	2001 Jun 15	11399037
Antimutagenic activity of green tea and black tea extracts studied in a dynamic in vitro gastrointestinal model.	2001 Mar 1	11239964
Stereospecificity in membrane effects of catechins.	2001 Mar 14	11248221
Phase I trial of oral green tea extract in adult patients with solid tumors.	2001 Mar 15	11251015
Synthesis of a 3,4,5-trimethoxybenzoyl ester analogue of epigallocatechin-3-gallate (EGCG): a potential route to the natural product green tea catechin, EGCG.	2001 Mar 22	11263896
EGCG, a major component of green tea, inhibits tumour growth by inhibiting VEGF induction in human colon carcinoma cells.	2001 Mar 23	11259102
Enantioselective synthesis of epigallocatechin-3-gallate (EGCG), the active polyphenol component from green tea.	2001 Mar 8	11259050
Water-soluble antioxidants inhibit macrophage recognition of oxidized erythrocytes.	2001 May	11379784
Green tea polyphenol (-)-epigallocatechin-3-gallate treatment to mouse skin prevents UVB-induced infiltration of leukocytes, depletion of antigen-presenting cells, and oxidative stress.	2001 May	11358979
Anti-interferon gamma action of epigallocatechin-3-gallate mediated by specific inhibition of STAT1 activation.	2001 May	11344123
Liquid chromatography with multi-channel electrochemical detection for the determination of epigallocatechin gallate in rat plasma utilizing an automated blood sampling device.	2001 Nov 5	11710582
The role of inducible nitric oxide synthase in cocaine-induced locomotor sensitization.	2001 Nov-Dec	11790403
Inhibition of UVB-induced oxidative stress-mediated phosphorylation of mitogen-activated protein kinase signaling pathways in cultured human epidermal keratinocytes by green tea polyphenol (-)-epigallocatechin-3-gallate.	2001 Oct 15	11601887
Inhibition by epigallocatechin gallate (EGCg) of conjugative R plasmid transfer in Escherichia coli.	2001 Sep	11810584
Green tea polyphenol (-)-epigallocatechin-3-gallate prevents N-methyl-4-phenyl-1,2,3,6-tetrahydropyridine-induced dopaminergic neurodegeneration.	2001 Sep	11553681
Epigallocatechin gallate synergy with ampicillin/sulbactam against 28 clinical isolates of methicillin-resistant Staphylococcus aureus.	2001 Sep	11533000
The green tea polyphenol (-)-epigallocatechin-3-gallate blocks nuclear factor-kappa B activation by inhibiting I kappa B kinase activity in the intestinal epithelial cell line IEC-6.	2001 Sep	11502884
Reduction of spontaneous mutagenesis in mismatch repair-deficient and proficient cells by dietary antioxidants.	2001 Sep 1	11506802
Epigallocatechin-3-gallate inhibits basic fibroblast growth factor-induced intracellular signaling transduction pathway in rat aortic smooth muscle cells.	2002 Feb	11791013
Preformulation study of epigallocatechin gallate, a promising antioxidant for topical skin cancer prevention.	2002 Jan	11782902
(-)Epigallocatechin-3-gallate inhibits leukocyte elastase: potential of the phyto-factor in hindering inflammation, emphysema, and invasion.	2002 Jan	11781382
Angioprevention': angiogenesis is a common and key target for cancer chemopreventive agents.	2002 Jan	11772931
Green tea catechins inhibit vascular endothelial growth factor receptor phosphorylation.	2002 Jan 15	11809684
In vitro therapeutic effect of epigallocatechin gallate on nicotine-induced impairment of resistance to Legionella pneumophila infection of established MH-S alveolar macrophages.	2002 Jan 15	11807697
Synergistic effects of (-)-epigallocatechin gallate with sulindac against colon carcinogenesis of rats treated with azoxymethane.	2002 Mar 8	11809530

Patents

Sample Use Guides

In Vivo Use Guide

Sunphenon EGCG (Epigallo Catechin Gallate) 200-800mg (1-4 capsules)

Route of Administration: Oral

In Vitro Use Guide

Epigallocatechin gallate (EGCG) could inhibit the viability and invasion, and induce the apoptosis, of bladder cancer T24 cells. The apoptosis of bladder cancer cells was notably increased by 20 µm EGCG. In addition, 20 µm EGCG inhibited bladder cancer cell viability. However, 10 µm EGCG did not exhibit any significant inhibitory effect on T24 cell viability. The effect of EGCG on the invasive ability of the bladder cancer cells was then investigated, which demonstrated that 10 µm and 20 µm of EGCG significantly inhibited invasion compared with the control group.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:37:53 GMT 2023` Edited by `admin` on `Fri Dec 15 15:37:53 GMT 2023`
Record UNII	BQM438CTEL
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

EPIGALLOCATECHIN GALLATE

Official Name

English

(-)-EPIGALLOCATECHIN-3-O-GALLATE (EGCG) (CONSTITUENT OF POWDERED DECAFFEINATED GREEN TEA EXTRACT) [DSC]

Common Name

English

(-)-EPIGALLOCATECHIN-3-O-GALLATE [USP-RS]

Common Name

English

PF-EGCG 90

Code

English

EGCG [MI]

Common Name

English

TEAVIGO

Brand Name

English

(-)-EPIGALLOCATECHIN-3-O-GALLATE

Common Name

English

EPIGALLOCATECHIN-GALLATE

Common Name

English

EGCG	Locators: MI WHO-DD Sources:

Common Name

English

EPIGALLOCATECHIN GALLATE [INCI]

Common Name

English

NVP-XAA 723

Code

English

3-O-GALLOYL-(-)-EPIGALLOCATECHIN

Common Name

English

(-)-EPIGALLOCATECHIN GALLATE

Common Name

English

BENZOIC ACID, 3,4,5-TRIHYDROXY-, (2R,3R)-3,4-DIHYDRO-5,7-DIHYDROXY-2-(3,4,5-TRIHYDROXYPHENYL)-2H-1-BENZOPYRAN-3-YL ESTER

Common Name

English

EPIGALLOCATECHIN 3-O-GALLATE

Common Name

English

EGCG [WHO-DD]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C68454