Hippeastrum reticulatum (Amaryllidaceae): Alkaloid Profiling, Biological Activities and Molecular Docking

Molecules. 2017 Dec 9;22(12):2191. doi: 10.3390/molecules22122191.

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.

Keywords: 6α-hydroxymaritidine; 6β-hydroxymaritidine; Hippeastrum reticulatum; isoreticulinine; reticulinine.

MeSH terms

  • Acetylcholinesterase / chemistry
  • Acetylcholinesterase / metabolism
  • Alkaloids / chemistry*
  • Alkaloids / pharmacology
  • Amaryllidaceae / chemistry*
  • Antiparasitic Agents / chemistry*
  • Antiparasitic Agents / pharmacology
  • Butyrylcholinesterase / chemistry
  • Butyrylcholinesterase / metabolism
  • Catalytic Domain / drug effects
  • Cholinesterase Inhibitors / chemistry*
  • Cholinesterase Inhibitors / pharmacology
  • Gas Chromatography-Mass Spectrometry
  • Hydrogen Bonding / drug effects
  • Models, Molecular
  • Molecular Docking Simulation
  • Molecular Structure
  • Plant Extracts / chemistry
  • Plant Extracts / pharmacology

Substances

  • Alkaloids
  • Antiparasitic Agents
  • Cholinesterase Inhibitors
  • Plant Extracts
  • Acetylcholinesterase
  • Butyrylcholinesterase