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

作者：Komlaga Gustav; Genta Jouve Gregory; Cojean Sandrine; Dickson Rita A; Mensah Merlin L K; Loiseau Philippe M; Champy Pierre^*; Beniddir Mehdi A^*

来源：Tetrahedron Letters, 2017, 58(38): 3754-3756.

DOI：10.1016/j.tetlet.2017.08.045

• Allonorsecurinine
• Ent-norsecurinine
• Phyllanthaceae
• Phyllanthus
• Antiplasmodial
• NMR shift calculation

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, entnorsecurinine (2) and (+)-allonorsecurinine (1) showed the strongest activity (IC50: 1.14 +/- 0.32 and 2.57 +/- 0.53 mu M) respectively, against W2 but one of the weakest against 3D7.

• 出版日期2017-9-20