Phenolic analogs of the N,C-coupled naphthylisoquinoline alkaloid ancistrocladinium A, from Ancistrocladus cochinchinensis (Ancistrocladaceae), with improved antiprotozoal activities

Phytochemistry. 2011 Jan;72(1):89-93. doi: 10.1016/j.phytochem.2010.10.006. Epub 2010 Nov 1.

Abstract

The first N,8'-coupled naphthylisoquinoline alkaloids with free phenolic OH groups, 4'-O-demethylancistrocladinium A and 6,4'-O-didemethylancistrocladinium A, have been isolated from the leaves and bark of the Vietnamese liana Ancistrocladus cochinchinensis, along with its known, non-phenolic parent compound, ancistrocladinium A, and four C,C-coupled representatives. The structure elucidation was achieved by chemical, spectroscopic, and chiroptical methods. The mono-phenolic alkaloid showed excellent activities in particular against the pathogen causing Chagas' disease, Trypanosoma cruzi.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / chemistry
  • Antiprotozoal Agents / chemistry
  • Antiprotozoal Agents / isolation & purification*
  • Antiprotozoal Agents / pharmacology
  • Isoquinolines / chemistry
  • Isoquinolines / isolation & purification*
  • Isoquinolines / pharmacology
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Plant Bark / chemistry
  • Plant Leaves / chemistry
  • Trypanosoma cruzi / drug effects*
  • Vietnam

Substances

  • 4'-O-demethylancistrocladinium A
  • 6,4'-O-didemethylancistrocladinium A
  • Alkaloids
  • Antiprotozoal Agents
  • Isoquinolines
  • ancistrocladinium A