Isolation of four new monoterpenes from Ailanthus altissima (mill.) Swingle and their enzyme inhibitory effects

Fitoterapia. 2024 Jul:176:105984. doi: 10.1016/j.fitote.2024.105984. Epub 2024 May 1.

Abstract

A phytochemical study of the ethanol extract from Ailanthus altissima (Mill.) Swingle leaves resulted in the isolation of four new monoterpenoids (1-3, 5). The structures were elucidated using HRESIMS data, NMR spectroscopic data, quantum chemical calculations for NMR and ECD, and custom DP4+ probability analysis. Additionally, the absolute configuration of sugar was determined by acid hydrolysis. Compounds 1-4 are cyclogeraniane monocyclic monoterpenes, while compound 5 contains an acyclic mycrane monoterpenes skeleton. Anti-tyrosinase, anti-acetylcholinesterase, and anti-butyrylcholinesterase activities were tested. Compound 1 showed notable anti-acetylcholinesterase activity, and compound 3 exhibited significant inhibitory effects on anti-tyrosinase activity. Furthermore, the potential binding sites of compounds 1 and 3 were predicted by molecular docking.

Keywords: Ailanthus altissima (mill.) Swingle; Enzyme inhibitory effects; Monoterpene.

MeSH terms

  • Acetylcholinesterase / metabolism
  • Ailanthus* / chemistry
  • Butyrylcholinesterase / metabolism
  • Cholinesterase Inhibitors / chemistry
  • Cholinesterase Inhibitors / isolation & purification
  • Cholinesterase Inhibitors / pharmacology
  • Molecular Docking Simulation*
  • Molecular Structure
  • Monophenol Monooxygenase / antagonists & inhibitors
  • Monoterpenes* / isolation & purification
  • Monoterpenes* / pharmacology
  • Phytochemicals* / isolation & purification
  • Phytochemicals* / pharmacology
  • Plant Leaves* / chemistry

Substances

  • Monoterpenes
  • Phytochemicals
  • Cholinesterase Inhibitors
  • Monophenol Monooxygenase
  • Acetylcholinesterase
  • Butyrylcholinesterase