Procyanidin A2

Procyanidin A2 is a natural flavanol dimer of (-)-epicatechin (Cay-11807) that is found in the horse chestnut (A. hippocastanum), mountain cranberry (V. vitis-idaea), and other fruits with antioxidant, anti-inflammatory, antibacterial, antiproliferative, and antidiabetic properties. It scavenges 2,2-diphenyl-1-picrylhydrazyl (DPPH, Cay-14805) radicals (IC50 = 5.08 µM) and inhibits STAT3 activation induced by platelet derived growth factor (PDGF) in primary rat vascular smooth muscle cells (VSMCs) when used at a concentration of 30 µg/ml. Procyanidin A2 inhibits growth of S. aureus and E. coli (MICs = 62.5 and 62.5 µg/ml, respectively) and proliferation of human HepG2 liver hepatocellular carcinoma and HeLa cervical cancer cells (EC50s = 62.19 and 66.07 µg/ml, respectively). It also increases insulin secretion from primary mouse pancreatic islets when used at a concentration of 10 µM in vitro and inhibits bisphenol A-induced glucose increases in fasted mice when administered at a dose of 10 µmol/kg per day.Formal Name: (2R,3R,8S,14R,15R)-2,8-bis(3,4-dihydroxyphenyl)-3,4-dihydro-8,14-methano-2H,14H-1-benzopyrano[7,8-d][1,3]benzodioxocin-3,5,11,13,15-pentol. CAS Number: 41743-41-3. Synonyms: (+)-Epicatechin-(4beta-8,2beta-O-7)-epicatechin, Proanthocyanidin A2, Procyanidin dimer A2, Procyanidol A2. Molecular Formula: C30H24O12. Formula Weight: 576.5. Purity: >95%. Formulation: (Request formulation change), A solid. Solubility: DMSO: Soluble, Ethanol: Soluble, Methanol: Soluble. lambdamax: 282 nm. SMILES: OC1=C(C[C@@H](O)[C@@H](C2=CC(O)=C(O)C=C2)O3)C3=C([C@@]([C@@]4([H])O)([H])C(C(O)=CC(O)=C5)=C5O[C@@]4(C6=CC(O)=C(O)C=C6)O7)C7=C1. InChi Code: InChI=1S/C30H24O12/c31-13-7-20(37)24-22(8-13)41-30(12-2-4-16(33)19(36)6-12)29(39)26(24)25-23(42-30)10-17(34)14-9-21(38)27(40-28(14)25)11-1-3-15(32)18(35)5-11/h1-8,10,21,26-27,29,31-39H,9H2/t21-,26-,27-,29-,30+/m1/s1. InChi Key: NSEWTSAADLNHNH-LSBOWGMISA-N. Origin: Plant/Grape seeds.