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Antitrypanosomal isoflavan quinones from Abrus precatorius

Hata, Yoshie and Ebrahimi, Samad Nejad and De Mieri, Maria and Zimmermann, Stefanie and Mokoka, Tsholofelo and Naidoo, Dashnie and Fouche, Gerda and Maharaj, Vinesh and Kaiser, Marcel and Brun, Reto and Potterat, Olivier and Hamburger, Matthias. (2014) Antitrypanosomal isoflavan quinones from Abrus precatorius. Fitoterapia, Vol. 93. S. 81-87.

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Official URL: http://edoc.unibas.ch/dok/A6243437

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Abstract

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 0.01μM, respectively), and remarkable SIs of 508, 374, 1379, and 668, respectively.
Faculties and Departments:05 Faculty of Science > Departement Pharmazeutische Wissenschaften > Pharmazie > Pharmazeutische Biologie (Hamburger)
09 Associated Institutions > Swiss Tropical and Public Health Institute (Swiss TPH)
09 Associated Institutions > Swiss Tropical and Public Health Institute (Swiss TPH) > Department of Medical Parasitology and Infection Biology > Parasite Chemotherapy (Mäser)
UniBasel Contributors:Brun, Reto and Hamburger, Matthias and Potterat, Olivier and Ebrahimi, Samad Nejad and Kaiser, Marcel and de Mieri, Maria and Hata Uribe, Yoshie Adriana
Item Type:Article, refereed
Bibsysno:Link to catalogue
Publisher:Elsevier Science
ISSN:0367-326X
Note:Publication type according to Uni Basel Research Database: Journal article
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Last Modified:23 May 2014 08:33
Deposited On:23 May 2014 08:33

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