Abstract
The Amaryllidaceae family has proven to be a rich source of active compounds, which are characterized by unique skeleton arrangements and a broad spectrum of biological activities. The aim of this work was to perform the first detailed study of the alkaloid constituents of Hippeastrum reticulatum (Amaryllidaceae) and to determine the anti-parasitological and cholinesterase (AChE and BuChE) inhibitory activities of the epimers (6α-hydroxymaritidine and 6β-hydroxymaritidine). Twelve alkaloids were identified in H. reticulatum: eight known alkaloids by GC-MS and four unknown (6α-hydroxymaritidine, 6β-hydroxymaritidine, reticulinine and isoreticulinine) by NMR. The epimer mixture (6α-hydroxymaritidine and 6β-hydroxymaritidine) showed low activity against all protozoan parasites tested and weak AChE-inhibitory activity. Finally, a molecular docking analysis of AChE and BuChE proteins showed that isoreticulinine may be classified as a potential inhibitory molecule since it can be stabilized in the active site through hydrogen bonds, π-π stacking and hydrophobic interactions.
Highlights
Natural products offer a wealth of bio-structural information that can be used to guide drug discovery and molecular design projects [1]
The MeOH extracts of H. reticulatum plants were fractioned following the sequence described in the Experimental section
The results suggest that in an ideal BuChE inhibitor π-π stacking and hydrogen bond interactions should be in equilibrium, and among the tested molecules isoreticulinine was closest to this definition
Summary
Natural products offer a wealth of bio-structural information that can be used to guide drug discovery and molecular design projects [1]. Plants have played a huge role in traditional medicine, and plant screening has become an important tool in drug discovery for pharmaceutical companies and university institutes [2]. Alkaloids are plant secondary metabolites that are usually low in nitrogen but high in oxygen [3] Their three-dimensional complexity and interesting ring systems are of great interest for drug development [3,4,5]. The Amaryllidaceae, a plant family in the monocot order Asparagales, is composed of three subfamilies: Amaryllidoideae, Agapanthoideae and Allioideae [6,7]. The Amaryllidoideae include about 80 genera [8] that are mainly distributed in tropical and subtropical regions, and in temperate
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