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Antiprotozoal Isoflavan Quinones from Abrus precatorius ssp. africanus

Hata, Yoshie and Raith, Melanie and Ebrahimi, Samad Nejad and Zimmermann, Stefanie and Mokoka, Tsholofelo and Naidoo, Dashnie and Fouche, Gerda and Maharaj, Vinesh and Kaiser, Marcel and Brun, Reto and Hamburger, Matthias. (2013) Antiprotozoal Isoflavan Quinones from Abrus precatorius ssp. africanus. Planta Medica, 79 (6). pp. 492-498.

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Official URL: http://edoc.unibas.ch/dok/A6124438

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Abstract

A library of 206 extracts from selected South African plants was screened in vitro against a panel of protozoan p arasites, 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 m icrog/mL. The active constituents were tracked by HPLC-based activity profiling and isolated by preparative and semi preparative 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 isofla van 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 microM, respectively) and good selectivity (selectivity indices of 73.7 and 50.5, 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:Hamburger, Matthias and Hata Uribe, Yoshie and Raith, Melanie and Zimmermann, Stefanie and Kaiser, Marcel and Brun, Reto and Ebrahimi, Samad Nejad
Item Type:Article, refereed
Article Subtype:Research Article
Bibsysno:Link to catalogue
Publisher:Georg Thieme Verlag
ISSN:0032-0943
e-ISSN:1439-0221
Note:Publication type according to Uni Basel Research Database: Journal article
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Last Modified:28 Nov 2017 08:40
Deposited On:24 May 2013 09:18

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