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

JAVIER E. ORTIZ; NATALIA B. PIGNI; SEBASTIAN A. ANDUJAR; GERMAN G. ROITMAN; FERNANDO SUVIRE; DANIEL ENRIZ; ALEJANDRO A. TAPIA; JAUME BASTIDA; GABRIELA E. FERESIN

JOURNAL OF NATURAL PRODUCTS

AMER CHEMICAL SOC

Lugar: Washington; 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 (MDS), and Quantum Theory of Atoms in Molecules (QTAIM) calculations provides new insight into the molecular interactions of compound 2 with BuChE, which were compared to those of galantamine (Gal).