Antiprotozoal isoflavan quinones from Abrus precatorius ssp. africanus

Planta Med. 2013 Apr;79(6):492-8. doi: 10.1055/s-0032-1328298. Epub 2013 Mar 19.

Abstract

A library of 206 extracts from selected South African plants was screened in vitro against a panel of protozoan parasites, Plasmodium falciparum, Trypanosoma brucei rhodesiense, and Leishmania donovani. A CH2Cl2/MeOH (1 : 1) extract of Abrus precatorius L. ssp. africanus strongly inhibited P. falciparum (98 %), T. b. rhodesiense (100 %), and L. donovani (76 %) when tested at a concentration of 10.0 µg/mL. The active constituents were tracked by HPLC-based activity profiling and isolated by preparative and semipreparative RP-HPLC chromatography. Structures were established by HR-ESIMS, and 1D and 2D NMR (1H, 13C, COSY, HMBC, HSQC, and NOE difference spectroscopy). Five compounds were obtained and identified as two isoflavan hydroquinones, abruquinone H (1) and abruquinone G (2), and three isoflavan quinones, abruquinone I (3), abruquinone B (4), and 7,8,3''5'-tetramethoxyisoflavan-1',4'-quinone (5). Compounds 1 and 3 were new natural products. The absolute configuration of compounds was determined by comparison of electronic circular dichroism spectra with calculated ECD data. Compounds 3 and 4 showed strong activity against T. b. rhodesiense (IC50 values of 0.30 and 0.16 µM, respectively) and good selectivity (selectivity indices of 73.7 and 50.5, respectively).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Abrus / chemistry*
  • Antiprotozoal Agents / chemistry
  • Antiprotozoal Agents / isolation & purification
  • Antiprotozoal Agents / pharmacology*
  • Chromatography, High Pressure Liquid
  • Nuclear Magnetic Resonance, Biomolecular
  • Plasmodium falciparum / drug effects*
  • Quinones / chemistry
  • Quinones / isolation & purification
  • Quinones / pharmacology*

Substances

  • Antiprotozoal Agents
  • Quinones