Micheliolide

Micheliolide is a sesquiterpene lactone and derivative of parthenolide (Cay-70080) that has been found in M. champaca and has diverse biological activities. It is an irreversible activator of the pyruvate kinase M2 isoform (PKM2, EC50 = 6 nM) that decreases viability of HL-60 cells when used at concentrations ranging from 5 to 20 µM. Micheliolide (5-10 µM) reduces M. tuberculosis-induced secretion of IL-1beta and TNF-alpha, expression of Cox2, and production of nitric oxide (NO) in RAW 264.7 cells. It also inhibits M. tuberculosis-induced NOD-, LRR-, and pyrin domain-containing protein 3 (NLRP3) inflammasome activation in RAW 264.7 cells. Micheliolide (30 mg/kg) decreases the severity of collagen-induced arthritis (CIA) in a mouse model of rheumatoid arthritis. It also increases hepatic protein levels of PPARgamma and reduces hepatic inflammation and steatosis in db/db mice.Formal Name: 3aS,4,5,7,8,9R,9aS,9bS-octahydro-9-hydroxy-6,9-dimethyl-3-methylene-azuleno[4,5-b]furan-2(3H)-one. CAS Number: 68370-47-8. Molecular Formula: C15H20O3. Formula Weight: 248.3. Purity: >98%. Formulation: (Request formulation change), A crystalline solid. Solubility: DMF: 5 mg/ml, DMSO: 5 mg/ml, DMSO:PBS (pH 7.2) (1:4): 0.20 mg/ml, Ethanol: 1 mg/ml. SMILES: CC1=C2[C@@]([C@@](O)(C)CC2)([H])[C@]3([H])[C@@](C(C(O3)=O)=C)([H])CC1. InChi Code: InChI=1S/C15H20O3/c1-8-4-5-11-9(2)14(16)18-13(11)12-10(8)6-7-15(12,3)17/h11-13,17H,2,4-7H2,1,3H3/t11-,12-,13-,15+/m0/s1. InChi Key: RDJAFOWISVMOJY-PWNZVWSESA-N. Origin: Plant/Costustoot.