Hirsutine

Hirsutine is an indole that has been found in U. rhynchophylla and has diverse biological activities. It selectively inhibits butyrylcholinesterase (BChE, IC50s = 1.97 and 4.97 µM for the human and horse enzymes, respectively) over eel acetylcholinesterase, for which it has no activity. Hirsutine also inhibits the homomeric serotonin (5-HT) receptor subtype 5-HT3A and heteromeric 5-HT3 receptors containing both A and B subunits (IC50s = 65.35 and 28.44 µM, respectively). It reduces glutamate-induced increases in cell death in HT22 cells when used at concentrations of 50 and 100 µM. Hirsutine (40, 60, and 80 µM) induces apoptosis in A549 and H1299 human non-small cell lung cancer (NSCLC) cells. It also reduces levels of Rho-associated kinase 1 (ROCK1) and phosphorylated glycogen synthase kinase 3beta (GSK3beta), as well as increases the level of phosphorylated phosphatase and tensin homolog (PTEN), in A549 cells. Hirsutine (10 mg/kg) reduces tumor growth and intratumoral levels of phosphorylated GSK3beta in an A549 mouse xenograft model. It also reduces infarct size and cardiac cell apoptosis and prevents cardiac dysfunction in a rat model of ischemia-reperfusion injury when administered at a dose of 20 mg/kg.Formal Name: (alphaE,2S,3R,12bR)-3-ethyl-1,2,3,4,6,7,12,12b-octahydro-alpha-(methoxymethylene)-indolo[2,3-a]quinolizine-2-acetic acid, methyl ester. CAS Number: 7729-23-9. Molecular Formula: C22H28N2O3. Formula Weight: 368.5. Purity: >98%. Formulation: (Request formulation change), A solid. Solubility: Acetone: Soluble, Chloroform: Soluble, Dichloromethane: Soluble, DMSO: Soluble, Ethyl Acetate: Soluble. lambdamax: 226, 283 nm. SMILES: COC(/C([C@H]1C[C@]2([H])C3=C(CCN2C[C@@H]1CC)C4=CC=CC=C4N3)=C/OC)=O. InChi Code: InChI=1S/C22H28N2O3/c1-4-14-12-24-10-9-16-15-7-5-6-8-19(15)23-21(16)20(24)11-17(14)18(13-26-2)22(25)27-3/h5-8,13-14,17,20,23H,4,9-12H2,1-3H3/b18-13+/t14-,17-,20+/m0/s1. InChi Key: NMLUOJBSAYAYEM-AZQGJTAVSA-N. Origin: Plant/Uncaria rhynchophylla.