Antiplasmodial Securinega alkaloids from Phyllanthus fraternus: Discovery of natural (+)-allonorsecurinine |
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| Authors: | Gustav Komlaga Grégory Genta-Jouve Sandrine Cojean Rita A. Dickson Merlin L.K. Mensah Philippe M. Loiseau Pierre Champy Mehdi A. Beniddir |
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| Affiliation: | 1. BioCIS, Équipe “Pharmacognosie-Chimie des Substances Naturelles” Univ. Paris-Sud, CNRS, Université Paris-Saclay, 92290 Châtenay-Malabry, France;2. Faculty of Pharmacy and Pharmaceutical Sciences, College of Health Sciences, Kwame Nkrumah Univeristy of Science and Technology, Kumasi, Ghana;3. C-TAC, UMR 8638 CNRS, Faculté de Pharmacie de Paris, Paris Descartes University, Sorbonne Paris Cité, 4, Avenue de l’Observatoire, 75006 Paris, France;4. BioCIS, Équipe “Chimiothérapie Antiparasitaire” Univ. Paris-Sud, CNRS, Université Paris-Saclay, 92290 Châtenay-Malabry, France |
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| Abstract: | The chemical investigation of the antimalarial plant Phyllanthus fraternus G. L. Webster (Phyllanthaceae) resulted in the discovery of the Securinega alkaloid (+)-allonorsecurinine (1), previously reported as a synthetic compound, together with the known ent-norsecurinine (2), nirurine (3), bubbialine (4), epibubbialine (5) and the lignan phyllanthin (6). The structure and absolute configuration of the new compound were elucidated on the basis of extensive spectroscopic analysis, optical rotation, and GIAO NMR shift calculation followed by CP3 analysis. The antiplasmodial activity of these compounds was evaluated against chloroquine-resistant (W2) and -sensitive (3D7) strains of Plasmodium falciparum. Among them, ent-norsecurinine (2) and (+)-allonorsecurinine (1) showed the strongest activity (IC50: 1.14 ± 0.32 and 2.57 ± 0.53 µM) respectively, against W2 but one of the weakest against 3D7. |
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| Keywords: | Allonorsecurinine Phyllanthaceae Antiplasmodial NMR shift calculation |
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