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

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
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
The heterocyclic ring fission and dehydroxylation of catechins and related compounds by Eubacterium sp. strain SDG-2, a human intestinal bacterium.	2001 Dec	11767089
Degradation of green tea catechins in tea drinks.	2001 Jan	11170614
Green tea polyphenol epigallocatechin inhibits DNA replication and consequently induces leukemia cell apoptosis.	2001 Jun	11351279
Green tea polyphenols: novel irreversible inhibitors of dopa decarboxylase.	2001 Jun 1	11374875
Stereospecificity in membrane effects of catechins.	2001 Mar 14	11248221
[Study on the analytical methods of catechins in tea and green tea polyphenol samples by high performance liquid chromatography].	2001 Sep	12545432
Composition of a chemopreventive proanthocyanidin-rich fraction from cranberry fruits responsible for the inhibition of 12-O-tetradecanoyl phorbol-13-acetate (TPA)-induced ornithine decarboxylase (ODC) activity.	2002 Feb 27	11853481
Isolation and characterization of alkyl peroxy radical scavenging compound from leaves of Laurus nobilis.	2002 Jan	11824536
Green tea polyphenol (-)-epigallocatechin 3-gallate inhibits MMP-2 secretion and MT1-MMP-driven migration in glioblastoma cells.	2002 Jan 30	11853893
Inhibition of aromatase activity by green tea extract catechins and their endocrinological effects of oral administration in rats.	2002 Jul	12065214
Evaluation of the antigenotoxic potential of monomeric and dimeric flavanols, and black tea polyphenols against heterocyclic amine-induced DNA damage in human lymphocytes using the Comet assay.	2002 Mar 25	11909753
Flavonoids uptake and their effect on cell cycle of human colon adenocarcinoma cells (Caco2).	2002 May 20	12085217
Investigation of the release of iron from ferritin by naturally occurring antioxidants.	2002 May 21	12009251
Effects of catechins on vascular tone in rat thoracic aorta with endothelium.	2002 Oct 11	12270760
Suppression of fatty acid synthase in MCF-7 breast cancer cells by tea and tea polyphenols: a possible mechanism for their hypolipidemic effects.	2003	12931129
Inhibition of proliferation of human cancer cells and cyclooxygenase enzymes by anthocyanidins and catechins.	2003	12925310
Analysis of oxidized epigallocatechin gallate by liquid chromatography/mass spectrometry.	2003	12876693
Inhibition of adenovirus infection and adenain by green tea catechins.	2003 Apr	12742577
DNA degradation by water extract of green tea in the presence of copper ions: implications for anticancer properties.	2003 Apr	12722140
Glucuronides of tea catechins: enzymology of biosynthesis and biological activities.	2003 Apr	12642472
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
Antioxidative compounds from Crotalaria sessiliflora.	2003 Feb	12729010
Determination of tea polyphenols and caffeine in tea flowers (Camellia sinensis) and their hydroxyl radical scavenging and nitric oxide suppressing effects.	2003 Feb 12	12568558
Polymeric proanthocyanidins from the bark of Hamamelis virginiana.	2003 Jan	12567291
Green tea catechins inhibit the cultured smooth muscle cell invasion through the basement barrier.	2003 Jan	12482547
Epimerization of tea catechins and O-methylated derivatives of (-)-epigallocatechin-3-O-gallate: relationship between epimerization and chemical structure.	2003 Jan 15	12517118
Green tea catechins evoke a phasic contraction in rat aorta via H2O2-mediated multiple-signalling pathways.	2003 Jan-Feb	12542460
Inhibition of metalloproteinase-9 activity and gene expression by polyphenolic compounds isolated from the bark of Tristaniopsis calobuxus (Myrtaceae).	2003 Jul	12943230
Identification of potential aryl hydrocarbon receptor antagonists in green tea.	2003 Jul	12870889
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
Radical chemistry of epigallocatechin gallate and its relevance to protein damage.	2003 Jun 1	12745262
Chain-breaking antioxidant activity of natural polyphenols as determined during the chain oxidation of methyl linoleate in Triton X-100 micelles.	2003 Jun 15	12781778
Factors affecting the levels of tea polyphenols and caffeine in tea leaves.	2003 Mar 26	12643643
Microemulsion electrokinetic chromatography for the analysis of green tea catechins: effect of the cosurfactant on the separation selectivity.	2003 May	12761797
Enzymology of methylation of tea catechins and inhibition of catechol-O-methyltransferase by (-)-epigallocatechin gallate.	2003 May	12695345
Antitumor principle constituents of Myrica rubra Var. acuminata.	2003 May 7	12720379

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.

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