Description
(−)-Epicatechin is a polyketide synthase-derived polyphenol flavonoid that has been found in
T. cacao and has diverse biological activities.
1,2,3,4,5 It scavenges DPPH (Item No.
14805) radicals in a cell-free assay when used at a concentration of 5 μM.
2 (−)-Epicatechin inhibits COX-1 (IC
50 = 3.2 μM).
6 It acts synergistically with epigallocatechin gallate (Item No.
70935) to induce apoptosis in, and reduce the proliferation of, PC-9 lung cancer cells when used at a concentration of 200 μM.
4 (−)-Epicatechin (80 mg/kg) reduces LPS-induced increases in plasma creatinine and urea levels in a rat model of renal inflammation.
5
Chemical Properties
white to light yellow crystal powde
Uses
An antioxidant and natural product from green tea
Uses
Catechin is a polyphenolic flavonoid that has been isolated from a variety of natural sources including tea leaves, grape seeds, and the wood and bark of trees such as acacia and mahogany. Catechin is a more potent antioxidant than ascorbate or α-tocopherol in certain in vitro lipid peroxidation assays. (?)-Epicatechin is a 2R,3R stereoisomer of catechin. Like catechin, (?)-epicatechin is a powerful antioxidant. It inhibits cyclooxygenase 1 (IC50 = 3.2 μM). Also, at 100 μM, (?)-epicatechin induces apoptosis in human adenocarcinoma PC-9 cells and stimulates the inhibition of tumor necrosis factor-α release from BALB-c/3T3 cells treated with epigallocatechin gallate.
Uses
Potent antioxidant and antineoplastic agent.
Definition
ChEBI: A catechin with (2R,3R)-configuration.
General Description
(?)-Epicatechin (EC) belongs to the group of flavanols and is abundantly present in cacao and cacao products. The chemical structure of EC includes an oxygenated heterocycle with a 4-hydroxyl group linked with two aromatic rings.
Biochem/physiol Actions
This antioxidant is found in chocolate. (-)-Epicatechin is linked with cardiovascular effects. It is considered as a dependable standard due to its availability in cacao seeds and cocoa products. The halogenating activity of myeloperoxidase can be restored by (-)-epicatechin.
References
[1]. chakravarthy bk, gupta s, gambhir ss, et al. pancreatic beta-cell regeneration in rats by (-)-epicatechin. lancet, 1981, 2(8249): 759-760.
[2]. wippel r, rehn m, gorren ac, et al. interference of the polyphenol epicatechin with the biological chemistry of nitric oxide- and peroxynitrite-mediated reactions. biochem pharmacol, 2004, 67(7): 1285-1295.
[3]. brossette t, hundsd?rfer c, kr?ncke kd, et al. direct evidence that (-)-epicatechin increases nitric oxide levels in human endothelial cells. eur j nutr, 2011, 50(7): 595-599.
[4]. okushio k, suzuki m, matsumoto n, et al. identification of (-)-epicatechin metabolites and their metabolic fate in the rat. drug metab dispos, 1999, 27(2): 309-316.
