Cytotoxic dihydrobenzophenanthridine alkaloids from the roots of Macleaya microcarpa

Phytochemistry. 2010 May;71(7):816-22. doi: 10.1016/j.phytochem.2010.02.007. Epub 2010 Mar 11.

Abstract

Five dihydrobenzophenanthridine alkaloids, named as maclekarpine A-E, were isolated from the roots of Macleaya microcarpa, together with 10 known benzophenanthridine/dihydrobenzophenanthridine derivatives and a known amide. Their structures were determined on the basis of spectroscopic methods. The relative configuration of maclekarpine A was solved by X-ray single-crystal diffraction, which also contributed to the establishment of the relative configuration of maclekarpine B and C, as well as the assignment of the absolute configuration of maclekarpine A-C with aid of their CD curves. Cytotoxicity of the isolated compounds against five human tumor cell-lines was evaluated, with some having activity with IC(50) values ranging from 0.1 to 3.5 microM.

MeSH terms

  • Alkaloids / isolation & purification*
  • Alkaloids / pharmacology
  • Antineoplastic Agents, Phytogenic / isolation & purification*
  • Antineoplastic Agents, Phytogenic / pharmacology
  • Cell Line, Tumor
  • Crystallography, X-Ray
  • Drug Screening Assays, Antitumor
  • Humans
  • Models, Molecular
  • Plant Roots / chemistry*
  • Spectrometry, Mass, Electrospray Ionization
  • Spectrometry, Mass, Fast Atom Bombardment

Substances

  • Alkaloids
  • Antineoplastic Agents, Phytogenic