Phenylpropanoids and a diarylpentanol from Stellera chamaejasme with acetylcholinesterase inhibitory activity

The chemical investigation on the roots of Stellera chamaejasme led to the identification of five undescribed compounds, including three lignans (1, 2, and 3b), one coumarin (4), one diarylpentanoid (5), and eight known analogues (3a, 6-10, and 11a/11b). Among them, two pairs of enantiomers were separated by chiral resolution. The structures of all compounds were elucidated by NMR spectroscopy and HRESIMS data analyses, quantum chemical calculations of NMR chemical shifts and ECD, as well as single-crystal X-ray diffraction analyses. All isolates were tested for their inhibitory activities against AChE, and compound 2 showed the most potent inhibitory activity, with an inhibition rate of 88.0% at 100 mu M. In addition, the possible interaction mechanism of 2 against AChE was predicted by molecular docking.

Automated summary

Chemical investigation of Stellera chamaejasme roots led to the discovery of five previously unidentified compounds, including three lignans (1, 2, and 3b), one coumarin (4), one diarylpentanoid (5), and eight known analogues (3a, 6-10, and 11a/11b). Chiral resolution successfully separated two pairs of enantiomers. The structures of all compounds were confirmed through NMR spectroscopy, HRESIMS data analysis, quantum chemical calculations, and single-crystal X-ray diffraction analyses. Compound 2 exhibited the strongest inhibitory activity against AChE, with an inhibition rate of 88.0% at 100 mu M. Molecular docking predicted the possible interaction mechanism of compound 2 with AChE.