EPIGALLOCATECHIN GALLATE

Possibly Marketed Outside US

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C22H18O11
Molecular Weight	458.3726
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

c1c(cc(c(c1O)O)O)[C@]2([H])[C@@]([H])(Cc3c(cc(cc3O2)O)O)OC(=O)c4cc(c(c(c4)O)O)O

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	458.3726
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 5 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 3315		6.89 µM [Ki]
NF-kappa B signaling pathway 25 Target ID: map04064 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21827739	Inhibitor 3315

Conditions

Condition	Modality	Highest Phase	Product
Multiple sclerosis 44 Sources: https://clinicaltrials.gov/ct2/show/NCT00799890	Primary	Phase III 257	Unknown Approved Use Unknown
Multiple system atrophy 1 Sources: https://clinicaltrials.gov/ct2/show/NCT02008721	Primary	Phase III 257	Unknown Approved Use Unknown
Duchenne muscular dystrophy 8 Sources: https://clinicaltrials.gov/ct2/show/NCT01183767	Primary	Phase III 257	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Mechanisms of cancer prevention by tea polyphenols based on inhibition of TNF-alpha expression.	2000	11237202
A new concept of tumor promotion by tumor necrosis factor-alpha, and cancer preventive agents (-)-epigallocatechin gallate and green tea--a review.	2000	10757128
Correlation of chemopreventive efficacy data from the human epidermal cell assay with in vivo data.	2000 Jan-Feb	10769631
Developing a dynamic pharmacophore model for HIV-1 integrase.	2000 Jun 1	10841789
Preventive effect of antioxidant on ultraviolet-induced skin cancer in mice.	2000 Mar	10764992
Anti-herpes simplex virus type-1 flavonoids and a new flavanone from the root of Limonium sinense.	2000 May	10865449
Differential responses of skin cancer-chemopreventive agents silibinin, quercetin, and epigallocatechin 3-gallate on mitogenic signaling and cell cycle regulators in human epidermoid carcinoma A431 cells.	2001	11759294
Ester bond-containing tea polyphenols potently inhibit proteasome activity in vitro and in vivo.	2001 Apr 20	11278274
The molecular interaction of human salivary histatins with polyphenolic compounds.	2001 Aug	11502198
Tea catechin, (-)-epigallocatechin gallate, causes membrane depolarizations of myenteric neurons in the guinea-pig small intestine.	2001 Aug 24	11502353
Apoptosis induction by epigallocatechin gallate involves its binding to Fas.	2001 Aug 3	11478767
Plasma concentrations of individual tea catechins after a single oral dose in humans.	2001 Dec	11780763
Rapid conversion of tea catechins to monomethylated products by rat liver cytosolic catechol-O-methyltransferase.	2001 Dec	11780762
The medicinal action of androgens and green tea epigallocatechin gallate.	2001 Dec	11773671
Effect of polyphenols on calcium content and alkaline phosphatase activity in rat femoral tissues in vitro.	2001 Dec	11767119
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
Evaluation of antioxidant activity of epigallocatechin gallate in biphasic model systems in vitro.	2001 Feb	11330830
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
Protective effects of (-)-epigallocatechin-3-gallate on UVA- and UVB-induced skin damage.	2001 Jan-Feb	11174086
Oxygen radical absorbance capacity of the phenolic compounds in plant extracts fractionated by high-performance liquid chromatography.	2001 Jun 15	11399037
A simple isolation method for the major catechins in green tea using high-speed countercurrent chromatography.	2001 Mar	11277755
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
Enantioselective synthesis of epigallocatechin-3-gallate (EGCG), the active polyphenol component from green tea.	2001 Mar 8	11259050
Anti-interferon gamma action of epigallocatechin-3-gallate mediated by specific inhibition of STAT1 activation.	2001 May	11344123
Mechanisms of inhibition of the Ras-MAP kinase signaling pathway in 30.7b Ras 12 cells by tea polyphenols (-)-epigallocatechin-3-gallate and theaflavin-3,3'-digallate.	2001 Sep	11511526
Cancer prevention with green tea and monitoring by a new biomarker, hnRNP B1.	2001 Sep 1	11506822
Molecular mechanisms underlying chemopreventive activities of anti-inflammatory phytochemicals: down-regulation of COX-2 and iNOS through suppression of NF-kappa B activation.	2001 Sep 1	11506818
(-)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
Potentiometric and (1)H NMR studies of complexation of Al(3+) with (-)-epigallocatechin gallate, a major active constituent of green tea.	2002 Jan 1	11750019

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 Jun 25 21:27:39 UTC 2021` Edited by `admin` on `Fri Jun 25 21:27:39 UTC 2021`
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 [WHO-DD]

Common Name

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

Classification Tree Code System Code

NCI_THESAURUS

C68454