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

Journal article
Authors M. Marco
Tsegaye Deyou
Amra Gruhonjic
J. Holleran
S. Duffy
M. Heydenreich
Paul A. Fitzpatrick
Göran Landberg
A. Koch
S. Derese
J. Pelletier
V. M. Avery
Mate Erdelyi
A. Yenesew
Published in Phytochemistry Letters
Volume 21
Pages 216-220
ISSN 1874-3900
Publication year 2017
Published at Swedish NMR Centre at Göteborg University
Sahlgrenska Cancer Center
Department of Chemistry and Molecular Biology
Pages 216-220
Language en
Links dx.doi.org/10.1016/j.phytol.2017.07...
Keywords Millettia micans, Millettia dura, Pterocarpan, Isoflavone, Cytotoxicity, Plasmodium falciparum, density-functional theory, circular-dichroism, seed pods, stem bark, flavonoids, Plant Sciences, Pharmacology & Pharmacy
Subject categories Medicinal Chemistry, Pharmaceutical Sciences, Bioorganic chemistry, Organic Chemistry, Pathology

Abstract

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 (38) 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 40 mu M). Maximaisoflavone B (5) and 7,2'-dimethoxy-4', 5'-methylenedioxyisoflavone (7) were weakly cytotoxic (IC50 153.5 and 174.1 mu M, respectively) against the MDA-MB-231 human breast cancer cell line. None of the tested compounds showed in-vitro translation inhibitory activity or toxicity against the HEK-293 human embryonic kidney cell line at 40 mu M.

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