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6 alpha-Hydroxy-alpha-toxicarol and (+)-tephrodin with antiplasmodial activities from Tephrosia species

  • The CH2Cl2/MeOH (1: 1) extract of the roots of Tephrosia villosa showed good antiplasmodial activity against the chloroquine-sensitive (D6) and chloroquine-resistant (W2) strains of Plasmodium falciparum with IC50 values of 3.1 +/- 0.4 and 1.3 +/- 0.3 mu g/mL, respectively. Chromatographic separation of the extract yielded a new rotenoid, 6 alpha-hydroxy-alpha-toxicarol, along with five known rotenoids, (rotenone, deguelin, sumatrol, 12 alpha-hydroxy-alpha-toxicarol and villosinol). Similar treatment of the extract of the stem of Tephrosia purpurea (IC50 = 4.1 +/- 0.4 and 1.9 +/- 0.2 mu g/mL against D6 and W2 strains of P. falciparum, respectively) yielded a new flavone having a unique substituent at C-7/C-8 [trivial name (+)-tephrodin], along with the known flavonoids tachrosin, obovatin methyl ether and derrone. The relative configuration and the most stable conformation in (+)-tephrodin was determined by NMR and theoretical energy calculations. The rotenoids and flavones tested showed good to moderate antiplasmodial activitiesThe CH2Cl2/MeOH (1: 1) extract of the roots of Tephrosia villosa showed good antiplasmodial activity against the chloroquine-sensitive (D6) and chloroquine-resistant (W2) strains of Plasmodium falciparum with IC50 values of 3.1 +/- 0.4 and 1.3 +/- 0.3 mu g/mL, respectively. Chromatographic separation of the extract yielded a new rotenoid, 6 alpha-hydroxy-alpha-toxicarol, along with five known rotenoids, (rotenone, deguelin, sumatrol, 12 alpha-hydroxy-alpha-toxicarol and villosinol). Similar treatment of the extract of the stem of Tephrosia purpurea (IC50 = 4.1 +/- 0.4 and 1.9 +/- 0.2 mu g/mL against D6 and W2 strains of P. falciparum, respectively) yielded a new flavone having a unique substituent at C-7/C-8 [trivial name (+)-tephrodin], along with the known flavonoids tachrosin, obovatin methyl ether and derrone. The relative configuration and the most stable conformation in (+)-tephrodin was determined by NMR and theoretical energy calculations. The rotenoids and flavones tested showed good to moderate antiplasmodial activities (IC50 = 9 +/- 23 mu M). Whereas the cytotoxicity of rotenoids is known, the flavones (+)-tephrodin and tachrosin did not show significant cytotoxicity (IC50 > 100 mu M;) against mammalian African monkey kidney (vero) and human larynx carcinoma (HEp2) cell lines. (C) 2014 Phytochemical Society of Europe. Published by Elsevier B.V. All rights reserved.show moreshow less

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Metadaten
Author:Lois Muiva-Mutisya, Bernard Macharia, Matthias Heydenreich, Andreas Koch, Hoseah M. Akala, Solomon DereseORCiD, Leonidah K. Omosa, Amir O. Yusuf, Edwin Kamau, Abiy Yenesew
DOI:https://doi.org/10.1016/j.phytol.2014.09.002
ISSN:1874-3900 (print)
ISSN:1876-7486 (online)
Parent Title (English):Phytochemistry letters
Publisher:Elsevier
Place of publication:Amsterdam
Document Type:Article
Language:English
Year of first Publication:2014
Year of Completion:2014
Release Date:2017/03/26
Tag:(+)-Tephrodin; 6 alpha-Hydroxy-alpha-toxicarol; Plasmodium falciparum; Tephrosia purpurea; Tephrosia villosa
Volume:10
Pagenumber:5
First Page:179
Last Page:183
Funder:National Commission for Science, Technology and Innovation (NACOSTI), Kenya; International Science Programme (ISP, Sweden) [KEN-02]
Organizational units:Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie
Peer Review:Referiert