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(-)-epicatechin gallatemajor catechin in green tea

(-)-epicatechin gallate

Catalog No. B4965
Size Price Stock Qty
5mg $85.00 In stock
10mg $140.00 In stock
20mg $240.00 In stock

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Sample solution is provided at 25 µL, 10mM.

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Chemical structure

(-)-epicatechin gallate

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Chemical Properties

Cas No. 1257-08-5 SDF Download SDF
Chemical Name (2R,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxychroman-3-yl 3,4,5-trihydroxybenzoate
Canonical SMILES OC1=CC(C(O[C@@H]2CC3=C(C=C(O)C=C3O)O[C@@H]2C4=CC=C(O)C(O)=C4)=O)=CC(O)=C1O
Formula C22H18O10 M.Wt 442.37
Solubility Soluble in DMSO Storage Store at -20°C
General tips N/A
Shipping Condition N/A

Background

(-)-epicatechin gallate is a major catechin component in green tea [1].

(-)-epicatechin gallate (ECG) plays an important role in cell growth inhibition, apoptosis and membrane transport system [1].

(-)-epicatechin gallate is a kind of catechin. In HCT-116 cells, ECG activated transcription factor 3 (ATF3), which played a critical role in pro-apoptosis. EGR-1 was involved in ECG-induced ATF3 expression. In HCT-116 cells, ECG (50 µM) increased NAG-1 and ATF3 expression in time- and dose-dependent way [1]. In carcinoma HSC-2 cells, ECG (50 µM) exhibited cytotoxicity with midpoint cytotoxicity (NR50) value of 67 µM. However, in normal HGF-2 fibroblasts, ECG exhibited cytotoxicity at concentrations up to 25 µM with NR50 value of 100 µM. In carcinoma HSC-2 cells, ECG (250 µM) induced nucleosomal DNA fragmentation and apoptosis. ECG (150 µM) significantly increased caspase-3 activity [2].

In rats, there were five metabolites of ECG: (-)-epicatechin gallate, 3’,4’’-di-O-methyl-(-)-epicatechin gallate, 4’’-O-methyl-(-)-epicatechin gallate, 4’-O-methyl-(-)-epicatechin gallate and 3’-O-methyl-(-)-epicatechin gallate, which were excreted in rat urine [3].

References:
[1].  Cho KN, Sukhthankar M, Lee SH, et al. Green tea catechin (-)-epicatechin gallate induces tumour suppressor protein ATF3 via EGR-1 activation. Eur J Cancer, 2007, 43(16): 2404-2412.
[2].  Babich H, Krupka ME, Nissim HA, et al. Differential in vitro cytotoxicity of (-)-epicatechin gallate (ECG) to cancer and normal cells from the human oral cavity. Toxicol In Vitro, 2005, 19(2): 231-242.
[3].  Kohri T, Suzuki M, Nanjo F. Identification of metabolites of (-)-epicatechin gallate and their metabolic fate in the rat. J Agric Food Chem, 2003, 51(18): 5561-5566.