Tsaokoic Acid: A New Bicyclic Nonene from the Fruits of Amomum tsao-ko with Acetylcholinesterase Inhibitory Activity

Molecules. 2023 Mar 13;28(6):2602. doi: 10.3390/molecules28062602.

Abstract

A new bicyclic nonene, tsaokoic acid (1), was isolated from the fruits of Amomum tsao-ko, together with three known compounds (2-4). The structure of 1 was elucidated by analyzing spectroscopic data including 1D and 2D NMR spectra and compounds 2-4 were identified as tsaokoin, vanillin, and tsaokoarylone, respectively, by comparing their NMR spectra with previously reported data. Compounds 1-4 showed possible inhibitory activity against acetylcholinesterase (AChE) in silico molecular docking simulations. They were submitted to in vitro assay system and exhibited moderate inhibitory activity with IC50 values of 32.78, 41.70, 39.25, and 31.13 μM, respectively.

Keywords: Amomum tsao-ko; Zingiberaceae; acetylcholinesterase; bicyclic nonene.

MeSH terms

  • Acetylcholinesterase
  • Amomum* / chemistry
  • Cholinesterase Inhibitors / analysis
  • Cholinesterase Inhibitors / pharmacology
  • Fruit* / chemistry
  • Molecular Docking Simulation
  • Molecular Structure

Substances

  • Acetylcholinesterase
  • Cholinesterase Inhibitors

Grants and funding

This work was supported by the National Research Foundation of Korea (NRF) grant funded by the Korea government (MIST) (No. 2021R1A2C1003350). This research was supported by Korea Basic Science Institute (National research Facilities and Equipment Center) grant funded by the Ministry of Education (2021R1A6C101A442).