(-)-Isoreserpine

• CAS: 482-85-9
• Catalog Number: ACM482859
• Category: Main Products
• Molecular Weight: 608.68
• Molecular Formula: C₃₃H₄₀N₂O₉
• Synonyms: (-)-ISORESERPINE;(20α)-18β-(3,4,5-Trimethoxybenzoyloxy)-11,17α-dimethoxyyohimban-16β-carboxylic acid methyl ester;20alpha-Yohimban-16beta-carboxylic acid, 18beta-hydroxy-11,17alpha-dimethoxy-, methyl ester, 3,4,5-trimethoxybenzoate (ester) (8ci);3-Epireserpine;Isoreserpin;Nsc 80138;Yohimban-16-carboxylic acid, 11,17-dimethoxy-18-((3,4,5-trimethoxybenzoyl)oxy)-, methyl ester, (16beta,17alpha,18beta,20alpha)- (9ci)
• IUPAC Name: methyl(1S,15S,17R,18R,19S,20S)-6,18-dimethoxy-17-(3,4,5-trimethoxybenzoyl)oxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate
• Canonical SMILES: COC1C(CC2CN3CCC4=C(C3CC2C1C(=O)OC)NC5=C4C=CC(=C5)OC)OC(=O)C6=CC(=C(C(=C6)OC)OC)OC
• InChI Key: QEVHRUUCFGRFIF-VPHNHGCZSA-N
• Boiling Point: 700.1ºC at 760mmHg
• Melting Point: 148-155°C(lit.)
• Flash Point: 377.2ºC
• Density: 1.32g/cm³
• Exact Mass: 608.27300
• Packing Group: III

Case Study

Isoreserpine for the Suppression of Colon Cancer via β-Catenin Degradation Mechanism

Gwak J, et al. Biochemical and Biophysical Research Communications, 2009, 387(3), 444-449.

Isoreserpine has been experimentally validated as a promising small-molecule modulator targeting the Wnt/β-catenin signaling pathway in colon cancer cells. In a high-throughput chemical screen using HEK293 cells transfected with a β-catenin/TCF-responsive TOPFlash luciferase reporter system and stimulated with Wnt3a-conditioned medium, isoreserpine was identified for its potent inhibitory effect on β-catenin activity. The compound significantly reduced reporter activity, indicating repression of the Wnt signaling cascade.
Further mechanistic studies revealed that isoreserpine enhances β-catenin degradation through the upregulation of Siah-1, an E3 ubiquitin ligase involved in β-catenin proteasomal degradation. This effect was confirmed in both HEK293 and HCT116 human colon cancer cells via Western blot analysis. Isoreserpine treatment led to marked decreases in β-catenin protein levels and downregulation of its downstream oncogenic targets, cyclin D1 and c-myc, as evidenced by RT-PCR and protein expression assays. Functionally, isoreserpine suppressed HCT116 cell proliferation in a dose-dependent manner, highlighting its antiproliferative efficacy.