Amaryllidaceae alkaloids from the bulbs of Crinum latifolium L. and their cholinesterase inhibitory activities

Phytochemistry. 2024 Jan:217:113929. doi: 10.1016/j.phytochem.2023.113929. Epub 2023 Nov 19.

Abstract

Eleven previously undescribed Amaryllidaceae alkaloids, crinalatifolines A-K (1-11), and two first naturally occurring alkaloids, dihydroambelline (12) and N-demethyldihydrogalanthamine (13), were isolated from the bulbs of Crinum latifolium L. Additionally, thirty-seven known alkaloids and one alkaloid artifact were also isolated from this plant species. Their structures and absolute configurations were elucidated using extensive spectroscopic techniques, including IR, NMR, MS, and ECD. Evaluations of the cholinesterase inhibitory activities of most of these compounds were conducted. Among the tested compounds, ungeremine exhibited the highest potency against acetylcholinesterase and butyrylcholinesterase, with the IC50 values of 0.10 and 1.21 μM, respectively. These values were 9.4- and 2.4-fold more potent than the reference drug galanthamine.

Keywords: Acetylcholinesterase; Alkaloids; Amaryllidaceae; Butyrylcholinesterase; Crinum latifolium L..

MeSH terms

  • Acetylcholinesterase
  • Alkaloids* / chemistry
  • Alkaloids* / pharmacology
  • Amaryllidaceae Alkaloids* / chemistry
  • Amaryllidaceae Alkaloids* / pharmacology
  • Butyrylcholinesterase
  • Cholinesterase Inhibitors / chemistry
  • Cholinesterase Inhibitors / pharmacology
  • Crinum* / chemistry
  • Plant Extracts / chemistry
  • Plant Extracts / pharmacology

Substances

  • Amaryllidaceae Alkaloids
  • Butyrylcholinesterase
  • Acetylcholinesterase
  • Cholinesterase Inhibitors
  • Alkaloids
  • Plant Extracts