EPIGALLOCATECHIN

Investigational

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C15H14O7
Molecular Weight	306.2675
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O[C@@H]1CC2=C(O[C@@H]1C3=CC(O)=C(O)C(O)=C3)C=C(O)C=C2O

InChI

InChIKey=XMOCLSLCDHWDHP-IUODEOHRSA-N

InChI=1S/C15H14O7/c16-7-3-9(17)8-5-12(20)15(22-13(8)4-7)6-1-10(18)14(21)11(19)2-6/h1-4,12,15-21H,5H2/t12-,15-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C15H14O7
Molecular Weight	306.2675
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/12925310

(-)-Epigallocatechin is a polyphenol, which occurs naturally in various plants, including green tea leaves. The compound was shown to have anti-cancer activity in vitro, with breast cancer, lung cancer, and colon cancer cells. The commercial preparation of Polyphenon E contains about 3% (-)-epigallocatechin as an impurity.

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cancer 592 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12925310	Primary		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Inhibitory effects of Sudanese plant extracts on HIV-1 replication and HIV-1 protease.	1999 Feb	10189947
Growth suppression of hamster flank organs by topical application of catechins, alizarin, curcumin, and myristoleic acid.	2001 Apr	11380153
Growth inhibitory effect of green tea extract and (-)-epigallocatechin in Ehrlich ascites tumor cells involves a cellular thiol-dependent activation of mitogenic-activated protein kinases.	2001 Apr 16	11311209
Analytical method of measuring tea catechins in human plasma by solid-phase extraction and HPLC with electrochemical detection.	2001 Dec	11922115
Rapid conversion of tea catechins to monomethylated products by rat liver cytosolic catechol-O-methyltransferase.	2001 Dec	11780762
The heterocyclic ring fission and dehydroxylation of catechins and related compounds by Eubacterium sp. strain SDG-2, a human intestinal bacterium.	2001 Dec	11767089
Detrimental effect of cancer preventive phytochemicals silymarin, genistein and epigallocatechin 3-gallate on epigenetic events in human prostate carcinoma DU145 cells.	2001 Feb 1	11170137
Formation and identification of 4'-O-methyl-(-)-epigallocatechin in humans.	2001 Jun	11353745
A tea catechin suppresses the expression of the high-affinity IgE receptor Fc epsilon RI in human basophilic KU812 cells.	2001 May	11368631
Inhibition of BMP-induced ectopic bone formation by an antiangiogenic agent (epigallocatechin 3-gallate).	2002	12489208
Antioxidant effects of green tea polyphenols on free radical initiated peroxidation of rat liver microsomes.	2002 Dec	12426080
Direct scavenging of nitric oxide and superoxide by green tea.	2002 Dec	12419687
Enhancement of inward Ca(2+) currents in bovine chromaffin cells by green tea polyphenol extracts.	2002 Feb	11738479
Kinetic analysis and mechanistic aspects of autoxidation of catechins.	2002 Jan 15	11853955
Green tea polyphenol (-)-epigallocatechin 3-gallate inhibits MMP-2 secretion and MT1-MMP-driven migration in glioblastoma cells.	2002 Jan 30	11853893
Effect of tea catechins on cellular lipid peroxidation and cytotoxicity in HepG2 cells.	2002 Jul	12224642
Inhibition of the PDGF beta-receptor tyrosine phosphorylation and its downstream intracellular signal transduction pathway in rat and human vascular smooth muscle cells by different catechins.	2002 Jun	12039871
Cellular thiol status-dependent inhibition of tumor cell growth via modulation of retinoblastoma protein phosphorylation by (-)-epigallocatechin.	2002 May 8	11880178
Regulation of IGFBP-5 expression during tumourigenesis and differentiation of oral keratinocytes.	2002 Nov	12375264
Opportunities for nutritional amelioration of radiation-induced cellular damage.	2002 Oct	12361786
Effects of catechins on vascular tone in rat thoracic aorta with endothelium.	2002 Oct 11	12270760
Prevention of nitric oxide-mediated 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine-induced Parkinson's disease in mice by tea phenolic epigallocatechin 3-gallate.	2002 Sep	12387363
Varietal differences among the polyphenol profiles of seven table grape cultivars studied by LC-DAD-MS-MS.	2002 Sep 25	12236700
Inhibition of proliferation of human cancer cells and cyclooxygenase enzymes by anthocyanidins and catechins.	2003	12925310
Inhibition of adenovirus infection and adenain by green tea catechins.	2003 Apr	12742577
MALDI-TOF mass spectrometry and PSD fragmentation as means for the analysis of condensed tannins in plant leaves and needles.	2003 Apr	12591272
The specificities of protein kinase inhibitors: an update.	2003 Apr 1	12534346
Green tea catechins inhibit the cultured smooth muscle cell invasion through the basement barrier.	2003 Jan	12482547
Complex effects of different green tea catechins on human platelets.	2003 Jul 10	12832052
Determination of tea components with antioxidant activity.	2003 Jul 16	12848521
Hop (Humulus lupulus L.) proanthocyanidins characterized by mass spectrometry, acid catalysis, and gel permeation chromatography.	2003 Jul 2	12822954

Patents

Sample Use Guides

In Vivo Use Guide

In a clinical trial, patients were given 1, 2, 3 or 4 capsules (1 capsule contains 37 mg (-)-epigallocatechin).

Route of Administration: Oral

In Vitro Use Guide

In a cell growth assay, human tumor cell lines MCF-7, SF-268, HCT-116 and NCI-H460 were treated with 100, 50, 25, 12.5, and 6.25 uM of (-)-epigallocatechin for 48 h. At concentration of 50 uM, the drug gave 50%, 10%, 60% and 40% inhibition of growth of breast, CNS, colon, and lung cancer cells, respectively.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:37:23 GMT 2023` Edited by `admin` on `Fri Dec 15 16:37:23 GMT 2023`
Record UNII	7Z197MG6QL
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

EPIGALLOCATECHIN

Common Name

English

EGC

Common Name

English

(-)-EPIGALLOCATECHOL

Common Name

English

EPIGALLOCATECHOL

Common Name

English

2H-1-BENZOPYRAN-3,5,7-TRIOL, 3,4-DIHYDRO-2-(3,4,5-TRIHYDROXYPHENYL)-, (2R,3R)-

Systematic Name

English

GALLOEPICATECHIN

Common Name

English

(-)-EPI-GALLOCATECHIN

Common Name

English

(-)-EPIGALLOCATECHIN

Common Name

English

NSC-674039

Code

English

SUNPHENON EGC

Brand Name

English

EPI-GALLOCATECHIN

Common Name

English

L-EPIGALLOCATECHIN

Common Name

English

ANTISCURVY FACTOR C2

Common Name

English

3,3',4',5,5',7-FLAVANHEXOL

Systematic Name

English

(-)-EPIGALLOCATECHIN(EGC) (CONSTITUENT OF POWDERED DECAFFEINATED GREEN TEA EXTRACT) [DSC]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C63651