Cynaropicrin

Cynaropicrin is a sesquiterpene lactone originally isolated from artichoke (C. scolymus) that has diverse biological activities. It inhibits the growth of SKOV3, LOX-IMVI, A549, MCF-7, HCT15, and PC-3 cancer cells (IC50s = 1.1-8.7 µg/ml). Cynaropicrin inhibits hepatitis C virus (HCV) replication in Huh7.5 cells with EC50 values ranging from 0.4 to 1.4 µM for genotypes 1a, 1b, 2b, 3a, 4a, 5a, 6a, and 7a. It inhibits release of TNF-alpha and nitric oxide (NO) from LPS-stimulated RAW264.7 cells (IC50s = 8.24 and 1.1 µM, respectively) as well as LPS-induced lymphocyte proliferation (IC50 = 0.9 µM). Cynaropicrin inhibits the growth of T. cruzi bloodstream trypomastigotes isolated from infected mice (EC50 = 1 µg/ml). It also exhibits antifeedant activity against S. granarius beetles, T. confusum larvae, and T. granarium larvae.Formal Name: 2-(hydroxymethyl)-2-propenoic acid, (3aR,4S,6aR,8S,9aR,9bR)-dodecahydro-8-hydroxy-3,6,9-tris(methylene)-2-oxoazuleno[4,5-b]furan-4-yl ester. CAS Number: 35730-78-0. Molecular Formula: C19H22O6. Formula Weight: 346.4. Purity: >98%. Formulation: (Request formulation change), A solution in ethanol. Solubility: DMF: miscible, DMSO: miscible, Ethanol: miscible, Ethanol:PBS(pH 7.2) (1:1): 0.5 mg/ml. SMILES: C=C([C@@H](O)C1)[C@@]2([H])[C@]1([H])C(C[C@H](OC(C(CO)=C)=O)[C@](C3=C)([H])[C@]2([H])OC3=O)=C. InChi Code: InChI=1S/C19H22O6/c1-8-5-14(24-18(22)9(2)7-20)16-11(4)19(23)25-17(16)15-10(3)13(21)6-12(8)15/h12-17,20-21H,1-7H2/t12-,13-,14-,15-,16+,17+/m0/s1. InChi Key: KHSCYOFDKADJDJ-NQLMQOPMSA-N. Origin: Plant/Cynara scolymus leaf.