Chebulagic Acid

Chebulagic acid is a polyphenol and tannin that has been found in T. chebula and has diverse biological activities. It is an inhibitor of COX-1, COX-2, and 5-lipoxygenase (5-LO, IC50s = 15, 0.92, and 2.1 µM, respectively) as well as alpha-glucosidase and 15-LO (IC50s = 0.05 and 24.9 µM, respectively). Chebulagic acid inhibits LPS-induced increases in inducible nitric oxide synthase (iNOS), COX-1, COX-2, and 5-LO protein levels, production of NO, prostaglandin E2 (PGE2), and reactive oxygen species (ROS), and nuclear translocation of NF-kappaB in RAW 264.7 macrophages in a concentration-dependent manner. It inhibits the growth of HCT15, COLO 205, MDA-MB-231, DU145, and K562 cancer cells (GI50s = 20.3, 18, 26.2, 28.54, and 30.66 µM, respectively). Chebulagic acid increases insulin-stimulated glucose uptake in 3T3-L1 adipocytes by 10.2-, 13.8-, and 16.6-fold when used at concentrations of 10, 50, and 100 µM, respectively. It also scavenges 2,2-diphenyl-1-picrylhydrazyl (DPPH) radicals (IC50 = 1.4 µM) and exhibits antiviral activity against cytomegalovirus, hepatitis C virus, dengue virus, measles virus, and respiratory syncytial virus in vitro (EC50s = 25.5, 12.16, 13.11, 34.42, and 0.38 µM, respectively).Formal Name: beta-D-glucopyranose, cyclic 3,6-[(1R)-4,4',5,5',6,6'-hexahydroxy[1,1'-biphenyl]-2,2'-dicarboxylate] 1-(3,4,5-trihydroxybenzoate), cyclic 2->2:4->1-ester with (2S)-2-[(3S,4S)-5-carboxy-3,4-dihydro-3,7,8-trihydroxy-2-oxo-2H-1-benzopyran-4-yl]butanedioic acid. CAS Number: 23094-71-5. Molecular Formula: C41H30O27. Formula Weight: 954.7. Purity: >98%. Formulation: (Request formulation change), A crystalline solid. Solubility: DMF: 20 m/gml, DMSO: 20 m/gml, DMSO:PBS (pH 7.2) (1:3): 0.25 mg/ml, Ethanol: 5 mg/ml. lambdamax: 226, 278 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](COC5=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)=C7C8=C(O)C(O)=C(O)C=C85)=O. InChi Code: InChI=1S/C41H30O27/c42-13-1-8(2-14(43)24(13)49)35(56)68-41-34-33-31(64-39(60)12(6-19(47)48)22-23-11(38(59)67-34)5-17(46)27(52)32(23)65-40(61)30(22)55)18(63-41)7-62-36(57)9-3-15(44)25(50)28(53)20(9)21-10(37(58)66-33)4-16(45)26(51)29(21)54/h1-5,12,18,22,30-31,33-34,41-46,49-55H,6-7H2,(H,47,48)/t12-,18+,22-,30-,31+,33-,34+,41-/m0/s1. InChi Key: HGJXAVROWQLCTP-YABCKIEDSA-N. Origin: Plant/Chebulae Fructus.