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Antiplasmodial Securinega alkaloids from Phyllanthus fraternus: Discovery of natural (+)-allonorsecurinine

Gustav Komlaga, Grégory Genta-Jouve, Sandrine Cojean, Rita A. Dickson, Merlin L.K. Mensah, Philippe M. Loiseau, Pierre Champy, Mehdi A. Beniddir
Tetrahedron letters 2017 pp. -
Phyllanthus fraternus, Plasmodium falciparum, Securinega, alkaloids, antimalarials, antiparasitic properties, chemical reactions, chemical structure, inhibitory concentration 50, lignans, nuclear magnetic resonance spectroscopy, spectral analysis
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±0.53µM) respectively, against W2 but one of the weakest against 3D7.