Four Pairs of Neuroprotective Aryldihydronaphthalene-Type Lignanamide Enantiomers from the Herbs of Solanum lyratum

Chem Biodivers. 2023 Sep;20(9):e202300941. doi: 10.1002/cbdv.202300941. Epub 2023 Aug 21.

Abstract

Four pairs of aryldihydronaphthalene-type lignanamide enantiomers were isolated from Solanum lyratum (Solanaceae). The enantiomeric separation was accomplished by chiral-phase HPLC, and five undescribed compounds were elucidated. Analysis by various spectroscopy and ECD calculations, the structures of undescribed compounds were illuminated. The neuroprotective effects of all compounds were evaluated using H2 O2 -induced human neuroblastoma SH-SY5Y cells and AchE inhibition activity. Among them, compound 4 a exhibited remarkable neuroprotective effects at high concentrations of 25 and 50 μmol/L comparable to Trolox. Compound 1 a showed the highest AchE inhibition with the IC50 value of 3.06±2.40 μmol/L. Molecular docking of the three active compounds was performed and the linkage between the compounds and the active site of AchE was elucidated.

Keywords: Solanum lyratum; aryldihydronaphthalene-type lignanamides; chiral resolution; molecular docking; neuroprotective activity.

MeSH terms

  • Humans
  • Molecular Docking Simulation
  • Molecular Structure
  • Neuroblastoma*
  • Neuroprotective Agents* / chemistry
  • Solanum* / chemistry
  • Stereoisomerism

Substances

  • Neuroprotective Agents