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|Title: ||Antiplasmodial Securinega Alkaloids from Phyllanthus fraternus: Discovery of Natural (+)-Allonorsecurinine|
|Authors: ||Dickson, Rita A.|
Mensah, Merlin L. K.
Loiseau, Philippe M.
Beniddir, Mehdi A.
NMR shift calculation
|Issue Date: ||Aug-2017|
|Publisher: ||Tetrahedron Letters|
|Citation: ||Tetrahedron Letters, Volume 58, Issue 38|
|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 chloroquineresistant (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 µM) respectively, against W2 but one of the weakest against 3D7.|
|Description: ||This article is published in Tetrahedron Letters and also available at https://doi.org/10.1016/j.tetlet.2017.08.045|
|Appears in Collections:||College of Health Sciences|
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