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(-)-epicatechin

In stock
Catalog No.
B4964
inducer of pancreatic β-cell regeneration
Grouped product items
SizePriceStock Qty
10mM (in 1mL DMSO)
$80.00
In stock
5mg
$85.00
In stock
10mg
$140.00
In stock
20mg
$240.00
In stock

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Background

(-)-epicatechin is a flavonoid that increases NO levels and an inducer of pancreatic β-cell regeneration [1] [2].

β cells are a subset of cells in the pancreatic islets and play an important role in regulating glucose homeostasis through the production of insulin.

(-)-epicatechin is an inducer of pancreatic β-cell regeneration. In murine macrophages, (-)-epicatechin induced nitrite accumulation induced by interferon-γ/lipopolysaccharide with IC50 value of 0.5 mM. Also, (-)-epicatechin inhibited nitration of free tyrosine induced by 0.1 and 1 mM peroxynitrite with IC50 values of 6.6 and 28.0 µM, respectively. In HL-60 cells, (-)-epicatechin inhibited nitration of protein-bound tyrosine induced by phorbol 12-myristate 13-acetate with IC50 value of 10-100 µM [2]. In human endothelial cells (HUVEC), (-)-epicatechin (0.3-10 µM) increased NO levels, suggesting its vasodilatory properties [3].

In alloxan diabetic rats, (-)-epicatechin (30 mg/kg) lowered blood sugar and restored the amount of beta-cells against alloxan-induced necrosis of the beta-cell population in the pancreatic islets. In rats, (-)-epicatechin was non-toxic up to 1 g/kg [1]. In rats, oral administration of (-)-epicatechin metabolized to 3’-O-methyl-(-)-epicatechin and 4’-O-methyl-(-)-epicatechin [4].

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, Hundsdörfer C, Kröncke 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.

Chemical Properties

Physical AppearanceA solid
StorageStore at -20°C
M.Wt290.27
Cas No.490-46-0
FormulaC15H14O6
Solubility≥14.5mg/mL in DMSO
Chemical Name(2R,3R)-2-(3,4-dihydroxyphenyl)chroman-3,5,7-triol
SDFDownload SDF
Canonical SMILESO[[email protected]@H]1CC2=C(C=C(O)C=C2O)O[[email protected]@H]1C3=CC=C(O)C(O)=C3
Shipping ConditionEvaluation sample solution : ship with blue ice.All other available size: ship with RT , or blue ice upon request
General tipsFor obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.

Quality Control

Chemical structure

(-)-epicatechin