Structurally diverse lignans from Solanum lyratum: chemical evidence for their acetylcholinease inhibitory activity

Abstract

A chemical investigation of Solanum lyratum Thumb. (Solanace) afforded two new lignans (1b and 3) and eleven known lignan analogues (1a, 2a/2b and 4–11). Compounds 1a/1b and 2a/2b were separated as two pairs of enantiomers by chiral high-performance liquid chromatography (HPLC). Their structures were elucidated by detailed spectroscopic and comparative literature data analysis. The absolute configurations of compounds 1a/1b and 2a/2b were determined by comparing the experimental ECD data with the calculated values. All compounds were evaluated for their acetylcholinesterase (AChE) inhibitory activity. Notably, compared to the positive control, compounds 4 and 9 showed obvious AChE inhibition with their IC₅₀ values of 1.30 ± 0.25 and 0.89 ± 0.04 μM, respectively. In addition, the possible interaction between acetylcholinesterase and the active compounds was also investigated by molecular docking.

Graphical Abstract

Keywords:

• Solanum lyratum
• lignans
• enantiomers
• AChE inhibition
• molecular docking

Disclosure statement

No potential conflict of interest was reported by the authors.

Additional information

Funding

This work was supported by Science and Technology Planning Project of Liaoning Province (2021JH1/10400049), Career Development Support Plan for Young and Middleaged Teachers in Shenyang Pharmaceutical University (ZQN2018006).