Pterocarpans and isoflavones from the root bark of Millettia micans and of Millettia dura |
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| Institution: | 1. Department of Chemistry, University of Nairobi, P. O. Box 30197-00100, Nairobi, Kenya;2. Department of Chemistry and Molecular Biology, University of Gothenburg, SE-40530, Gothenburg, Sweden;3. Sahlgrenska Cancer Centre, University of Gothenburg, SE-405 30 Gothenburg, Sweden;4. Discovery Biology, Griffith Institute for Drug Discovery, Griffith University, Nathan, QLD 4111, Australia;5. Institut für Chemie, Universität Potsdam, Karl-Liebknecht-Str. 24-25, D-14476 Potsdam, Germany;6. Department of Biochemistry, McGill University, Montreal, QC, H3G 1Y6, Canada;7. Swedish NMR Center, University of Gothenburg, P.O. Box 465, SE-40530, Gothenburg, Sweden;1. Key Laboratory of Chemistry in Ethnic Medicinal Resources, State Ethnic Affairs Commission & Ministry of Education, Yunnan Minzu University, Kunming 650031, PR China;2. Research and Development Center, China Tobacco Yunnan Industrial Co., Ltd., Kunming 650231, PR China;3. Clinical Laboratory, First People’s Hospital of Yunnan Province, Kunming 650032, PR China;1. Chulabhorn Research Institute, Kamphaeng Phet 6, Talat Bang Khen, Lak Si, Bangkok 10210, Thailand;2. Faculty of Pharmaceutical Sciences, Khon Kaen University, Khon Kaen 40002, Thailand;1. School of Medicine and Life Sciences, University of Jinan-Shandong Academy of Medical Sciences, Jinan 250200, Shandong, China;2. Institute of Materia Medica, Shandong Academy of Medical Sciences, Key Laboratory for Biotech-Drugs Ministry of Health, Key Laboratory for Rare & Uncommon Diseases of Shandong Province, Jinan 250062, Shandong, China;3. State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences & Peking Union Medical College, Beijing 100050, China;1. State Key Laboratory of Natural Medicines, Department of Natural Medicinal Chemistry, China Pharmaceutical University, Nanjing 210009, PR China;2. Jiangsu Key Laboratory of Drug Screening, China Pharmaceutical University, Nanjing 210009, PR China;3. Guangdong Province Key Laboratory of Pharmacodynamic Constituents of TCM and New Drug Research, Jinan University, Guangzhou 510632, PR China;1. Department of Chemistry, Faculty of Science, Ege University, 35100 Bornova, Izmir, Turkey;2. Department of Chemistry, Faculty of Science, Çank?r? Karatekin University, Çank?r?, Turkey;1. State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, Yunnan, People’s Republic of China;2. Yunnan University of TCM, Kunming, 650500, Yunnan, People’s Republic of China |
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| 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 (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 40 μM). Maximaisoflavone B (5) and 7,2′-dimethoxy-4′,5′-methylenedioxyisoflavone (7) were weakly cytotoxic (IC50 153.5 and 174.1 μM, 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 μM. |
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| Keywords: | Pterocarpan Isoflavone Cytotoxicity |
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