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

ORTIZ, JAVIER E.; ROITMAN, GERMAN; TAPIA, ALEJANDRO; ORTIZ, JAVIER E.; ROITMAN, GERMAN; TAPIA, ALEJANDRO; ANDUJAR, SEBASTIÁN A.; ENRIZ, RICARDO D.; FERESIN, GABRIELA E.; ANDUJAR, SEBASTIÁN A.; ENRIZ, RICARDO D.; PIGNI, NATALIA B.; FERESIN, GABRIELA E.; SUVIRE, FERNANDO D.; BASTIDA, JAUME; PIGNI, NATALIA B.; SUVIRE, FERNANDO D.; BASTIDA, JAUME

JOURNAL OF NATURAL PRODUCTS

AMER CHEMICAL SOC

Año: 2016 vol. 79 p. 1241 - 1248

0163-3864

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.