New flavonoids from the underground parts of Eriosema laurentii |
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| Affiliation: | 1. Laboratory of Animal Physiology, Department of Animal Biology and Physiology, Faculty of Science, University of Yaounde I, P.O. Box 812, Yaounde, Cameroon;2. Department of Pharmacognosy, University of Vienna, Althanstrasse 14, 1090 Vienna, Austria;3. Department of Pharmaceutical Chemistry, University of Vienna, Althanstrasse 14, 1090 Vienna, Austria;4. Institute of Organic Chemistry, University of Vienna, Währingerstraße 38, A-1090 Vienna, Austria;5. Department of Biotechnology, University of Natural Resources and Life Sciences Vienna, Muthgasse 18, A-1190 Vienna, Austria;1. Pharmacognosie et Molécules Naturelles Bioactives, Laboratoire d’Innovation Thérapeutique, UMR 7200, CNRS-Université de Strasbourg, Faculté de Pharmacie, 74 Route du Rhin, F-67401 Illkirch Cedex, France;2. Laboratoire de Pharmacochimie des Substances Naturelles, Département de Chimie Organique, Faculté de Sciences, Université de Yaoundé, BP 812, Yaoundé, Cameroon;3. Laboratoire de Chimie Thérapeutique, UMR7312, 51 Rue Cognacq-Jay, 51100 Reims, France;1. Tianjin Key Laboratory for Modern Drug Delivery and High-Efficiency, School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, PR China;2. Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin 300072, PR China;3. Pharmaceutical Engineering Department, School of Biological Science and Technology, University of Jinan, Shandong 250022, PR China;1. Center of Research and Development on Life Sciences and Environment Sciences, Harbin University of Commerce, Harbin 150076, China;2. Institute of Medicinal Plant Development, Chinese Academy of Medical Sciences & Peking Union Medical College, Beijing 100193, China;3. Institute of Medicine Plantationof Chongqing, Chongqing 408435, China;4. College of chemistry and materials science, Guangxi Teachers Education University, Manning 530001, China;1. Unidade de Biotecnologia, Universidade de Ribeirão Preto, Av. Costábile Romano, 2201, 14096-900, Brazil;2. Faculdade de Ciências Farmacêuticas de Ribeirão Preto, Universidade de São Paulo, Avenida do Café s/n, 14040-903, Brazil |
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| Abstract: | Pharmacological, toxicological and phytochemical investigations of aerial parts of Eriosema laurentii De Wild. (Leguminosae), a plant used in traditional African medicine, showed a complex pattern of very rare and several new exceptional phenolic compounds. In continuation of the phytochemical work and based on the activity of an extract from the underground parts, the presented study showed the occurrence of a new pyranoisoflavone, named methyleriosemaone D, and a new highly prenylated (2S,3S)-6,8,3′-triprenyl-3,5,7,2′,4′-pentahydroxyflavanone in these parts of E. laurentii. In addition, the very rare pyranoisoflavone eriosemaone D was proven in this plant for the first time. All structures were elucidated unambiguously by extensive MS- and one and two-dimensional NMR-experiments. Detailed NMR spectra of eriosemaone D were included to rationalize the correction of some of the previously reported carbon signals in the 13C NMR spectrum. The estrogenic activity of the extract and isolated compounds was tested in an estrogen receptor α yeast transactivation assay. |
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| Keywords: | Leguminosae Eriosemaone D Methyleriosemaone D (2S,3S)-6,8,3′-Triprenyl-3,5,7,2′,4′-pentahydroxyflavanone |
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