Description
Procyanidin A1 is found in cinnamon and is extracted from the herbs of Daemonorops draco. It is an epicatechin-(2β→7,4β→8)-catechin dimer and is potential precursor of 5-(3',4'-dihydroxyphenyl)-γ-valerolactone. It inhibits LDL oxidation with the IC50 value of 0.94 uM. It also inhibits degranulation downstream of protein kinase C activation or Ca2⁺ influx from an internal store in RBL-2H3 cells. It shows antiallergic effects.
Synonyms
Proanthocyanidin A1; Epicatechin-(2b->7,4b->8)-catechin; (2R,3S,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
IUPAC Name
(1R,5R,6S,13S,21R)-5,13-bis(3,4-dihydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.02,11.03,8.015,20]henicosa-2(11),3(8),9,15,17,19-hexaene-6,9,17,19,21-pentol
Molecular Formula
C30H24O12
Canonical SMILES
C1C(C(OC2=C3C4C(C(OC5=CC(=CC(=C45)O)O)(OC3=CC(=C21)O)C6=CC(=C(C=C6)O)O)O)C7=CC(=C(C=C7)O)O)O
InChI
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-/m0/s1
InChIKey
NSEWTSAADLNHNH-TXZJYACMSA-N