Chebulinic Acid

Chebulinic acid is an ellagitannin that has been found in T. chebula and has diverse biological activities. It is an inhibitor of protein tyrosine phosphatase non-receptor 9 (PTPN9) and PTPN11 (IC50s = 34 and 37 nM, respectively). Chebulinic acid (5 µM) increases glucose uptake in 3T3-L1 preadipocytes. It induces apoptosis of HL-60 and NB4 acute promyelocytic leukemia (APL), but not K562 chronic myelogenous leukemia (CML), cells (IC50s = 7.5, 5, and >60 µM, respectively). Chebulinic acid (25 µM) reduces the production of reactive oxygen species (ROS) induced by glyceraldehyde-related advanced glycation end products (glycer-AGEs) in human umbilical vein endothelial cells (HUVECs) and reduces glutamate-induced ROS production and cell death in HT22 mouse hippocampal cells. It inhibits H+/K+-ATPase activity (IC50 = 65.01 µg/ml) and reduces free and total gastric acidity, as well as increases gastric mucin secretion, in various rat models of gastric ulcer.Formal Name: 1,3,6-tris(3,4,5-trihydroxybenzoate) cyclic 2->2:4->1-ester with (2S)-[(3R,4S)-5-carboxy-3,4-dihydro-3,7,8-trihydroxy-2-oxo-2H-1-benzopyran-4-yl]butanedioic acid, beta-D-glucopyranose. CAS Number: 18942-26-2. Synonyms: Eutannin, NSC 69862. Molecular Formula: C41H32O27. Formula Weight: 956.7. Purity: >98%. Formulation: (Request formulation change), A crystalline solid. Solubility: Ethanol: soluble. lambdamax: 222, 283 nm. SMILES: O=C([C@H]([C@]1([H])[C@@H](O)C(OC2=C1C3=CC(O)=C2O)=O)CC(O)=O)O[C@@H]4[C@@H](COC(C5=CC(O)=C(O)C(O)=C5)=O)O[C@@H](OC(C6=CC(O)=C(O)C(O)=C6)=O)[C@H](OC3=O)[C@@H]4OC(C7=CC(O)=C(O)C(O)=C7)=O. InChi Code: InChI=1S/C41H32O27/c42-15-1-10(2-16(43)26(15)51)35(56)62-9-22-31-33(66-36(57)11-3-17(44)27(52)18(45)4-11)34(41(63-22)68-37(58)12-5-19(46)28(53)20(47)6-12)67-38(59)13-7-21(48)29(54)32-25(13)24(30(55)40(61)65-32)14(8-23(49)50)39(60)64-31/h1-7,14,22,24,30-31,33-34,41-48,51-55H,8-9H2,(H,49,50)/t14-,22+,24-,30+,31+,33+,34+,41-/m0/s1. InChi Key: YGVHOSGNOYKRIH-IFPULTQJSA-N. Origin: Plant/Fructus Chebulae.