TY - JOUR A1 - Juma, Wanyama P. A1 - Akala, Hoseah M. A1 - Eyase, Fredrick L. A1 - Muiva, Lois M. A1 - Heydenreich, Matthias A1 - Okalebo, Faith A. A1 - Gitu, Peter M. A1 - Peter, Martin G. A1 - Walsh, Douglas S. A1 - Imbuga, Mabel A1 - Yenesew, Abiy T1 - Terpurinflavone an antiplasmodial flavone from the stem of Tephrosia Purpurea JF - Phytochemistry letters N2 - The stem extract of Tephrosia purpurea showed antiplasmodial activity against the D6 (chloroquine-sensitive) and W2 (chloroquine-resistant) strains of Plasmodium falciparum with IC(50) values of 10.47 +/- 2.22 mu g/ml and 12.06 +/- 2.54 mu g/ml, respectively. A new prenylated flavone, named terpurinflavone, along with the known compounds lanceolatin A, (-)-semiglabrin and lanceolatin B have been isolated from this extract. The new compound, terpurinflavone, showed the highest antiplasmodial activity with IC(50) values of 3.12 +/- 0.28 mu M (D6) and 6.26 +/- 2.66 mu M (W2). The structures were determined on the basis of spectroscopic evidence. KW - Tephrosia purpurea KW - Leguminosae KW - Stem KW - Flavone KW - Terpurinflavone KW - Antiplasmodial Y1 - 2011 U6 - https://doi.org/10.1016/j.phytol.2011.02.010 SN - 1874-3900 VL - 4 IS - 2 SP - 176 EP - 178 PB - Elsevier CY - Amsterdam ER - TY - GEN A1 - Peter, Martin G. A1 - Muiva, Lois M. A1 - Yenesew, Abiy A1 - Derese, Solomon A1 - Heydenreich, Matthias A1 - Akala, Hoseah M. A1 - Eyase, Fredrick A1 - Waters, Norman C. A1 - Mutai, Charles A1 - Keriko, Joseph M. A1 - Walsh, Douglas S. T1 - Antiplasmodial β-hydroxydihydrochalcone from seedpods of Tephrosia elata N2 - From the seedpods of Tephrosia elata, a new β-hydroxydihydrochalcone named (S)-elatadihydrochalcone was isolated. In addition, the known flavonoids obovatachalcone, obovatin, obovatin methyl ether and deguelin were identified. The structures were determined on the basis of spectroscopic evidence. The crude extract and the flavonoids obtained from the seedpods of this plant showed antiplasmodial activities. The literature NMR data on β-hydroxydihydrochalcones is reviewed and the identity of some of the compounds assigned β-hydroxydihydrochalcone skeleton is questioned. T3 - Zweitveröffentlichungen der Universität Potsdam : Mathematisch-Naturwissenschaftliche Reihe - paper 118 KW - Tephrosia elata KW - Leguminosae KW - Seedpods KW - (S)-Elatadihydrochalcone KW - β-Hydroxydihydrochalcone Y1 - 2009 U6 - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:kobv:517-opus-44437 ER - TY - JOUR A1 - Muiva-Mutisya, Lois M. A1 - Atilaw, Yoseph A1 - Heydenreich, Matthias A1 - Koch, Andreas A1 - Akala, Hoseah M. A1 - Cheruiyot, Agnes C. A1 - Brown, Matthew L. A1 - Irungu, Beatrice A1 - Okalebo, Faith A. A1 - Derese, Solomon A1 - Mutai, Charles A1 - Yenesew, Abiy T1 - Antiplasmodial prenylated flavanonols from Tephrosia subtriflora JF - Natural Product Research N2 - The CH2Cl2/MeOH (1:1) extract of the aerial parts of Tephrosia subtriflora afforded a new flavanonol, named subtriflavanonol (1), along with the known flavanone spinoflavanone B, and the known flavanonols MS-II (2) and mundulinol. The structures were elucidated by the use of NMR spectroscopy and mass spectrometry. The absolute configuration of the flavanonols was determined based on quantum chemical ECD calculations. In the antiplasmodial assay, compound 2 showed the highest activity against chloroquine-sensitive Plasmodiumfalciparum reference clones (D6 and 3D7), artemisinin-sensitive isolate (F32-TEM) as well as field isolate (KSM 009) with IC50 values 1.4-4.6M without significant cytotoxicity against Vero and HEp2 cell lines (IC50>100M). The new compound (1) showed weak antiplasmodial activity, IC50 12.5-24.2M, but also showed selective anticancer activity against HEp2 cell line (CC50 16.9M). [GRAPHICS] . KW - Tephrosia subtriflora KW - Leguminosae KW - prenylated flavanonol KW - subtriflavanonol KW - antiplasmodial KW - cytotoxicity Y1 - 2018 U6 - https://doi.org/10.1080/14786419.2017.1353510 SN - 1478-6419 SN - 1478-6427 VL - 32 IS - 12 SP - 1407 EP - 1414 PB - Routledge, Taylor & Francis Group CY - Abingdon ER - TY - JOUR A1 - Atilaw, Yoseph A1 - Duffy, Sandra A1 - Heydenreich, Matthias A1 - Muiva-Mutisya, Lois A1 - Avery, Vicky M. A1 - Erdelyi, Mate A1 - Yenesew, Abiy T1 - Three Chalconoids and a Pterocarpene from the Roots of Tephrosia aequilata JF - Molecules N2 - In our search for new antiplasmodial agents, the CH2Cl2/CH3OH (1:1) extract of the roots of Tephrosia aequilata was investigated, and observed to cause 100% mortality of the chloroquine-sensitive (3D7) strain of Plasmodium falciparum at a 10 mg/mL concentration. From this extract three new chalconoids, E-2,6-dimethoxy-3,4-(2,2-dimethyl)pyranoretrochalcone (1, aequichalcone A), Z-2,6-dimethoxy-3,4-(2,2-dimethyl)pyranoretrochalcone (2, aequichalcone B), 4-ethoxy-3-hydroxypraecansone B (3, aequichalcone C) and a new pterocarpene, 3,4:8,9-dimethylenedioxy-6a,11a-pterocarpene (4), along with seven known compounds were isolated. The purified compounds were characterized by NMR spectroscopic and mass spectrometric analyses. Compound 1 slowly converts into 2 in solution, and thus the latter may have been enriched, or formed, during the extraction and separation process. The isomeric compounds 1 and 2 were both observed in the crude extract. Some of the isolated constituents showed good to moderate antiplasmodial activity against the chloroquine-sensitive (3D7) strain of Plasmodium falciparum. KW - Tephrosia aequilata KW - chalcone KW - retrochalcone KW - aequichalcone A KW - aequichalcone B KW - aequichalcone C KW - pterocarpene KW - antiplasmodial Y1 - 2017 U6 - https://doi.org/10.3390/molecules22020318 SN - 1420-3049 VL - 22 IS - 2 PB - MDPI CY - Basel ER - TY - JOUR A1 - Muiva-Mutisya, Lois A1 - Macharia, Bernard A1 - Heydenreich, Matthias A1 - Koch, Andreas A1 - Akala, Hoseah M. A1 - Derese, Solomon A1 - Omosa, Leonidah K. A1 - Yusuf, Amir O. A1 - Kamau, Edwin A1 - Yenesew, Abiy T1 - 6 alpha-Hydroxy-alpha-toxicarol and (+)-tephrodin with antiplasmodial activities from Tephrosia species JF - Phytochemistry letters N2 - 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 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. KW - Tephrosia villosa KW - Tephrosia purpurea KW - 6 alpha-Hydroxy-alpha-toxicarol KW - (+)-Tephrodin KW - Plasmodium falciparum Y1 - 2014 U6 - https://doi.org/10.1016/j.phytol.2014.09.002 SN - 1874-3900 SN - 1876-7486 VL - 10 SP - 179 EP - 183 PB - Elsevier CY - Amsterdam ER -