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Antiprotozoal Isoflavan Quinones from Abrus precatorius ssp. africanus
JournalArticle (Originalarbeit in einer wissenschaftlichen Zeitschrift)
 
ID 1712478
Author(s) Hata, Yoshie; Raith, Melanie; Ebrahimi, Samad Nejad; Zimmermann, Stefanie; Mokoka, Tsholofelo; Naidoo, Dashnie; Fouche, Gerda; Maharaj, Vinesh; Kaiser, Marcel; Brun, Reto; Hamburger, Matthias
Author(s) at UniBasel Hamburger, Matthias
Hata Uribe, Yoshie Adriana
Raith, Melanie
Zimmermann, Stefanie
Kaiser, Marcel
Brun, Reto
Ebrahimi, Samad
Year 2013
Title Antiprotozoal Isoflavan Quinones from Abrus precatorius ssp. africanus
Journal Planta Medica
Volume 79
Number 6
Pages / Article-Number 492-8
Keywords antiprotozoal, Trypanosoma brucei rhodesiense, isoflavan quinone, Abrus precatorius, Fabaceae, electronic circular dichroism
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)
Publisher Georg Thieme Verlag
ISSN/ISBN 0032-0943 ; 1439-0221
edoc-URL http://edoc.unibas.ch/dok/A6124438
Full Text on edoc No
Digital Object Identifier DOI 10.1055/s-0032-1328298
PubMed ID http://www.ncbi.nlm.nih.gov/pubmed/23512498
ISI-Number WOS:000317814300011
Document type (ISI) Journal Article
 
   

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