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Antitrypanosomal isoflavan quinones from Abrus precatorius.
Journal article

Antitrypanosomal isoflavan quinones from Abrus precatorius.

  • Hata Y Department of Pharmaceutical Sciences, University of Basel, Klingelbergstrasse 50, CH-4056 Basel, Switzerland; Department of Pharmacy, Faculty of Sciences, National University of Colombia, Carrera 30 No. 45-03, Bogota D.C. 111321, Colombia.
  • Ebrahimi SN Department of Pharmaceutical Sciences, University of Basel, Klingelbergstrasse 50, CH-4056 Basel, Switzerland; Department of Phytochemistry, Medicinal Plant and Drugs Research Institute, Shahid Beheshti University, G. C., Tehran, Iran.
  • De Mieri M Department of Pharmaceutical Sciences, University of Basel, Klingelbergstrasse 50, CH-4056 Basel, Switzerland.
  • Zimmermann S Department of Pharmaceutical Sciences, University of Basel, Klingelbergstrasse 50, CH-4056 Basel, Switzerland.
  • Mokoka T Biosciences, Council for Scientific and Industrial Research (CSIR), PO Box 395, Pretoria 0001, South Africa.
  • Naidoo D Biosciences, Council for Scientific and Industrial Research (CSIR), PO Box 395, Pretoria 0001, South Africa.
  • Fouche G Biosciences, Council for Scientific and Industrial Research (CSIR), PO Box 395, Pretoria 0001, South Africa.
  • Maharaj V Biosciences, Council for Scientific and Industrial Research (CSIR), PO Box 395, Pretoria 0001, South Africa.
  • Kaiser M Swiss Tropical and Public Health Institute and University of Basel, Socinstrasse 57, CH-4002 Basel, Switzerland.
  • Brun R Swiss Tropical and Public Health Institute and University of Basel, Socinstrasse 57, CH-4002 Basel, Switzerland.
  • Potterat O Department of Pharmaceutical Sciences, University of Basel, Klingelbergstrasse 50, CH-4056 Basel, Switzerland.
  • Hamburger M Department of Pharmaceutical Sciences, University of Basel, Klingelbergstrasse 50, CH-4056 Basel, Switzerland. Electronic address: matthias.hamburger@unibas.ch.
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  • 2014-01-03
Published in:
  • Fitoterapia. - 2014
Abrus precatorius
ECD
Fabaceae
Isoflavan quinone
Trypanosoma brucei rhodesiense
Abrus
Animals
Benzopyrans
Benzoquinones
Microbial Sensitivity Tests
Rats
Trypanocidal Agents
English Human African trypanosomiasis is a neglected tropical disease in sub Saharan Africa that is fatal if left untreated. In a search for new natural products with antitrypanosomal activity, we recently identified abruquinones B and I from Abrus precatorius as potent in vitro trypanocidal compounds with high selectivity indices. To obtain sufficient compound for in vivo efficacy tests in mice, a second batch of plant material was re-collected and extracted. However, the chemical profiles of the two batches differed, and additional abruquinones were isolated and identified by HR-ESI-MS, and 1D and 2D NMR ((1)H, (13)C, COSY, HMBC, HSQC, and NOESY) spectroscopy. Abruquinones J (1), K (2), and L (3) were new, while abruquinones A (4) and D (5) were known from the first batch of plant material. The absolute configuration of compounds 1 to 3 was determined by comparison of electronic circular dichroism (ECD) spectra with calculated ECD data. Compounds 2 to 5 showed high in vitro activity against T. b. rhodesiense (IC50 of 0.01, 0.02, 0.02 and 0.01 μM, respectively), and remarkable SIs of 508, 374, 1379, and 668, respectively.
Language
  • English
Open access status
closed
Identifiers
Persistent URL
https://sonar.ch/global/documents/8608
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