Mitraphylline

Mitraphylline is the major pentacyclic oxindolic alkaloid found in U. tomentosa and has anti-inflammatory and antiproliferative properties. It reduces production of nitric oxide (NO), IL-8, IL-6, and TNF-alpha as well as expression of inducible nitric oxide synthase (iNOS) in LPS-activated human neutrophils. Mitraphylline inhibits the growth of SKN-BE(2) neuroblastoma, GAMG glioblastoma, MHH-ES-1 Ewing's sarcoma, and MT-3 breast cancer cells (IC50s = 12.3, 20, 17.15, and 11.18 µM, respectively). In vivo, mitraphylline (30 mg/kg per day) inhibits LPS-induced release of IL-1alpha, IL-1beta, IL-17, and TNF-alpha in mouse serum.Formal Name: (1'S,3R,4'aS,5'aS,10'aR)-1,2,5',5'a,7',8',10',10'a-octahydro-1'-methyl-2-oxo-spiro[3H-indole-3,6'(4'aH)-[1H]pyrano[3,4-f]indolizine]-4'-carboxylic acid, methyl ester. CAS Number: 509-80-8. Molecular Formula: C21H24N2O4. Formula Weight: 368.4. Purity: >98%. Formulation: (Request formulation change), A crystalline solid. Solubility: DMF: 5 mg/ml, DMSO: 5 mg/ml, DMSO:PBS (pH 7.2) (1:2): 0.33 mg/ml, Ethanol: slightly soluble. lambdamax: 243 nm. SMILES: O=C1NC2=C(C=CC=C2)[C@]31CCN4C[C@]5([H])[C@H](C)OC=C(C(OC)=O)[C@@]5([H])C[C@]43[H]. InChi Code: InChI=1S/C21H24N2O4/c1-12-14-10-23-8-7-21(16-5-3-4-6-17(16)22-20(21)25)18(23)9-13(14)15(11-27-12)19(24)26-2/h3-6,11-14,18H,7-10H2,1-2H3,(H,22,25)/t12-,13-,14+,18-,21+/m0/s1. InChi Key: JMIAZDVHNCCPDM-DAFCLMLCSA-N. Origin: Plant/Uncaria tomentosa.