Peganumine A, a β-carboline dimer with a new octacyclic scaffold from Peganum harmala

Org Lett. 2014 Aug 1;16(15):4028-31. doi: 10.1021/ol501856v. Epub 2014 Jul 23.

Abstract

Peganumine A (1), a new dimeric β-carboline alkaloid characterized by a unique 3,9-diazatetracyclo[6.5.2.0(1,9).0(3,8)]pentadec-2-one scaffold, was isolated from the seeds of Peganum harmala. The structure including the absolute configuration was determined by spectroscopic data, X-ray crystallography, ECD calculation, and CD exciton chirality approaches. Compound 1 showed moderate cytotoxic activity against MCF-7, PC-3, and HepG2 cells and selective effects on HL-60 cells with an IC50 value of 5.8 μM.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / chemistry
  • Alkaloids / isolation & purification*
  • Alkaloids / pharmacology
  • Antineoplastic Agents, Phytogenic / chemistry
  • Antineoplastic Agents, Phytogenic / isolation & purification*
  • Antineoplastic Agents, Phytogenic / pharmacology
  • Carbolines / chemistry
  • Carbolines / isolation & purification*
  • Carbolines / pharmacology
  • Crystallography, X-Ray
  • Drug Screening Assays, Antitumor
  • HL-60 Cells
  • Hep G2 Cells
  • Humans
  • Inhibitory Concentration 50
  • Molecular Conformation
  • Molecular Structure
  • Peganum / chemistry*
  • Seeds / chemistry

Substances

  • Alkaloids
  • Antineoplastic Agents, Phytogenic
  • Carbolines
  • peganumine A