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Pterocarpans and isoflavones from the roots of Millettia micans and of Millettia dura

Journal article
Authors Marco Makungu
Tsegaye Deyou
Amra Gruhonjic
John P. Holleran
Sandra Duffy
Matthias Heydenreich
Paul A. Fitzpatrick
Göran Landberg
Andreas Koch
Solomon Derese
Jerry Pelletier
Vicky M. Avery
Mate Erdelyi
Abiy Yenesew
Published in Advances in Drug Discovery and Development
Volume 1
Issue 1
Pages 1-8
Publication year 2016
Published at Swedish NMR Centre at Göteborg University
Sahlgrenska Cancer Center
Department of Chemistry and Molecular Biology
Pages 1-8
Language en
Links halogenbond.weebly.com/uploads/6/7/...
Keywords Millettia micans, pterocarpan, malaria
Subject categories Medicinal Chemistry, Pharmacognosy, Chemistry, Chemical Sciences, Organic Chemistry

Abstract

From the CH2Cl2/CH3OH (1:1) extract of the root bark of Millettia micans, a new pterocarpan, (6aR,11aR)-7,8,9-trimethoxy-3-hydroxypterocarpan (1), named micanspterocarpan, was isolated. Similarinvestigation of the CH2Cl2/CH3OH (1:1) extract of the root bark of Millettia dura gave a further new pterocarpan,3-O-prenylmaackiain (2) along with six known isoflavones (3-8) and a chalcone (9). All purifiedcompounds were identified by NMR and MS, and the absolute configuration of 1 was established by quantumchemical CD calculation. 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 Plasmodiumfalciparum (70-90% inhibition at 40 M). Maximaisoflavone B (5) and 7,2'-dimethoxy-4',5'-methylenedioxyisoflavone (7) were weakly cytotoxic (IC50 153.5 and 174.1 uM, respectively) against theMDB-MB-231 human breast cancer cell line. None of the tested compounds showed toxicity against theHEK-293 human embryonic kidney cell line at 40 uM.

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