CATECHIN GALLATE, (-)-

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C22H18O10
Molecular Weight	442.3723
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=C4)C(O)=C1

InChI

InChIKey=LSHVYAFMTMFKBA-CTNGQTDRSA-N

InChI=1S/C22H18O10/c23-11-6-14(25)12-8-19(32-22(30)10-4-16(27)20(29)17(28)5-10)21(31-18(12)7-11)9-1-2-13(24)15(26)3-9/h1-7,19,21,23-29H,8H2/t19-,21+/m1/s1

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Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12925310 | https://www.ncbi.nlm.nih.gov/pubmed/14640575

(-)-Catechin gallate 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. It is supposed that the drug may act by inhibiting Bcl family of proteins. It has been reported to inhibit HIV-1 replication by targeting several steps in HIV-1 life cycle. (-)-Catechin gallate (in combination with other catechins) caused the hypocholesterolemic effect in rats.

Approval Year

Targets

Primary Target	Pharmacology	Potency
Bcl-2-like protein 1 3 Target ID: Q07817 Gene ID: 598.0 Gene Symbol: BCL2L1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/14678963	Inhibitor 8297	143.0 nM [Ki]
Apoptosis regulator Bcl-2 19 Target ID: P10415 Gene ID: 596.0 Gene Symbol: BCL2 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/14678963	Inhibitor 8297	230.0 nM [Ki]
Human immunodeficiency virus type 1 integrase 19 Target ID: CHEMBL3471 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20832370	Inhibitor 8297	0.56 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Cancer 592 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12925310	Primary	Basic research	Unknown Approved Use Unknown
Atherosclerosis 74 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14640575	Preventing	Preclinical	Unknown Approved Use Unknown
HIV-1 infection 151 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20832370	Primary	Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Cancer prevention by tea polyphenols is linked to their direct inhibition of antiapoptotic Bcl-2-family proteins.	2003 Dec 1	14678963
Heat-epimerized tea catechins rich in gallocatechin gallate and catechin gallate are more effective to inhibit cholesterol absorption than tea catechins rich in epigallocatechin gallate and epicatechin gallate.	2003 Dec 3	14640575
Theaflavin derivatives in black tea and catechin derivatives in green tea inhibit HIV-1 entry by targeting gp41.	2005 May 25	15823507
The evaluation of catechins that contain a galloyl moiety as potential HIV-1 integrase inhibitors.	2010 Dec	20832370
Novel type II fatty acid biosynthesis (FAS II) inhibitors as multistage antimalarial agents.	2013 Mar	23341167

Sample Use Guides

In Vivo Use Guide

Rats were administered the emulsion of heat-epimerized catechins at the concentration of 120 mg in 3 ml (the mixture contains 7.7% (-)-catechin gallate, 7.29% (-)-epicatechin gallate, 24.1% (-)-gallocatechin gallate and 20.9% (-)-epigallocatechin gallate).

Route of Administration: Other

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 (-)-catechin gallate for 48 h. The drug gave about 40% inhibition of growth of breast, colon, and lung cancer cells, at 50-uM concentration.

Name

Type

Language

CATECHIN GALLATE, (-)-

Common Name

English

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

Systematic Name

English

(2S,3R)-2-(3,4-DIHYDROXYPHENYL)-3,4-DIHYDRO-1(2H)-BENZOPYRAN-3,5,7-TRIOL 3-(3,4,5-TRIHYDROXYBENZOATE)

Systematic Name

English

(-)-CATECHIN 3-O-GALLATE

Common Name

English

(-)-CATECHIN 3-GALLATE

Common Name

English

(-)-CATECHIN GALLATE

Common Name

English

Code System Code Type Description

CAS

130405-40-2