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Alkaloids from Hippeastrum argentinum and Their Cholinesterase-Inhibitory Activities: An in Vitro and in Silico Study

Ortiz, Javier E., Pigni, Natalia B., Andujar, Sebastián A., Roitman, German, Suvire, Fernando D., Enriz, Ricardo D., Tapia, Alejandro, Bastida, Jaume, Feresin, Gabriela E.
Journal of natural products 2016 v.79 no.5 pp. 1241-1248
Hippeastrum, alkaloids, bulbs, chemical elements, cholinesterase, gas chromatography-mass spectrometry, inhibitory concentration 50, molecular dynamics, molecular models, quantum mechanics
Two new alkaloids, 4-O-methylnangustine (1) and 7-hydroxyclivonine (2) (montanine and homolycorine types, respectively), and four known alkaloids were isolated from the bulbs of Hippeastrum argentinum, and their cholinesterase-inhibitory activities were evaluated. These compounds were identified using GC-MS, and their structures were defined by physical data analysis. Compound 2 showed weak butyrylcholinesterase (BuChE)-inhibitory activity, with a half-maximal inhibitory concentration (IC₅₀) value of 67.3 ± 0.09 μM. To better understand the experimental results, a molecular modeling study was also performed. The combination of a docking study, molecular dynamics simulations, and quantum theory of atoms in molecules calculations provides new insight into the molecular interactions of compound 2 with BuChE, which were compared to those of galantamine.