Azaphenanthrene alkaloids with antitumoral activity from Anaxagorea dolichocarpa Sprague & Sandwith (Annonaceae)

Molecules. 2011 Aug 22;16(8):7125-31. doi: 10.3390/molecules16087125.

Abstract

Phytochemical investigation of Anaxagorea dolichocarpa Sprague & Sandwith led to isolation of three azaphenanthrene alkaloids: eupolauramine, sampangine and imbiline 1. Their chemical structures were established on the basis of spectroscopic data from IR, HR-ESI-MS, NMR (including 2D experiments) and comparison with the literature. Sampangine and imbiline 1 are being described in the Anaxagorea genus for the first time. Eupolauramine and sampangine show concentration-dependent antitumoral activity in leukemic cells K562 with IC(50) of 18.97 and 10.95 µg/mL, respectively.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / chemistry
  • Alkaloids / isolation & purification*
  • Alkaloids / pharmacology
  • Annonaceae / chemistry*
  • Antineoplastic Agents, Phytogenic / chemistry
  • Antineoplastic Agents, Phytogenic / isolation & purification
  • Antineoplastic Agents, Phytogenic / pharmacology*
  • Aza Compounds / chemistry
  • Aza Compounds / isolation & purification
  • Aza Compounds / pharmacology*
  • Cell Line, Tumor
  • Cell Survival / drug effects
  • Drug Screening Assays, Antitumor
  • Heterocyclic Compounds, 4 or More Rings / chemistry
  • Heterocyclic Compounds, 4 or More Rings / isolation & purification*
  • Heterocyclic Compounds, 4 or More Rings / pharmacology
  • Humans
  • Molecular Structure
  • Naphthyridines
  • Phenanthrenes / chemistry
  • Phenanthrenes / isolation & purification
  • Phenanthrenes / pharmacology*
  • Plant Bark / chemistry*
  • Plant Extracts / chemistry
  • Plant Extracts / isolation & purification
  • Plant Extracts / pharmacology*

Substances

  • Alkaloids
  • Antineoplastic Agents, Phytogenic
  • Aza Compounds
  • Heterocyclic Compounds, 4 or More Rings
  • Naphthyridines
  • Phenanthrenes
  • Plant Extracts
  • eupolauramine
  • sampangine