Pterocarpans and isoflavones from the root bark of Millettia micans and of Millettia dura

Publication date: September 2017 Source:Phytochemistry Letters, Volume 21 Author(s): Makungu Marco, Tsegaye Deyou, Amra Gruhonjic, John Holleran, Sandra Duffy, Matthias Heydenreich, Paul A. Firtzpatrick, Göran Landberg, Andreas Koch, Solomon Derese, Jerry Pelletier, Vicky M. Avery, Máté Erdélyi, Abiy Yenesew From the CH2Cl2/CH3OH (1:1) extract of the root bark of Millettia micans, a new pterocarpan, (6aR,11aR)-3-hydroxy-7,8,9-trimethoxypterocarpan (1), named micanspterocarpan, was isolated. Similar investigation of the CH2Cl2/CH3OH (1:1) extract of the root bark of Millettia dura gave a further new pterocarpan, (6aR,11aR)-8,9-methylenedioxy-3-prenyloxypterocarpan (2), named 3-O-prenylmaackiain, along with six known isoflavones (3-8) and a chalcone (9). All purified compounds were identified by NMR and MS, whereas the absolute configurations of the new pterocarpans were established by chriptical data analyses including quantum chemical ECD calculation. Among the isolated constituents, calopogonium isoflavone B (3) and isoerythrin A-4′-(3-methylbut-2-enyl) ether (4) showed marginal activities against the 3D7 and the Dd2 strains of Plasmodium falciparum (70–90% inhibition at 40μM). Maximaisoflavone B (5) and 7,2′-dimethoxy-4′,5′-methylenedioxyisoflavone (7) were weakly cytotoxic (IC50 153.5 and 174.1μM, respectively) against the MDA-MB-231 human breast cancer cell line. None of the tested compounds showed in-vitro translation inhibitory activity o...
Source: Phytochemistry Letters - Category: Chemistry Source Type: research