Antitrypanosomal isoflavan quinones from Abrus precatorius.

Hata Y; Ebrahimi SN; De Mieri M; Zimmermann S; Mokoka T; Naidoo D; Fouche G; Maharaj V; Kaiser M; Brun R; Potterat O; Hamburger M

doi:10.1016/j.fitote.2013.12.015

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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.

2014-01-03

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Fitoterapia. - 2014

Trypanosoma brucei rhodesiense

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.

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