Chemical Composition and Acetylcholinesterase Inhibitory Activity of Essential Oils from Piper Species

J Agric Food Chem. 2017 May 10;65(18):3702-3710. doi: 10.1021/acs.jafc.7b01350. Epub 2017 May 1.

Abstract

The essential oils (EOs) derived from aromatic plants such as Piper species are considered to play a role in alleviating neuronal ailments that are associated with inhibition of acetylcholinesterase (AChE). The chemical compositions of 23 EOs prepared from 16 Piper spp. were analyzed by both gas chromatography with a flame ionization detector (GC-FID) and gas chromatography-mass spectrometry (GC-MS). A total of 76 compounds were identified in the EOs from the leaves and stems of 19 samples, while 30 compounds were detected in the EOs from the fruits of four samples. Sesquiterpenes and phenylpropanoids were found to be rich in these EOs, of which asaricin, caryophyllene, caryophyllene oxide, isospathulenol, (+)-spathulenol, and β-bisabolene are the major constituents. The EOs from the leaves and stems of Piper austrosinense, P. puberulum, P. flaviflorum, P. betle, and P. hispidimervium showed strong AChE inhibitory activity with IC50 values in the range of 1.51 to 13.9 mg/mL. A thin-layer chromatography (TLC) bioautography assay was employed to identify active compound(s) in the most active EO from P. hispidimervium. The active compound was isolated and identified as asaricin, which gave an IC50 value of 0.44 ± 0.02 mg/mL against AChE, comparable to galantamine with an IC50 0.15 ± 0.01 mg/mL.

Keywords: P. hispidimervium; Piper; acetylcholinesterase inhibitory activity; asaricin; essential oil.

MeSH terms

  • Acetylcholinesterase / chemistry*
  • Animals
  • Cholinesterase Inhibitors / chemistry*
  • Chromatography, Thin Layer
  • Eels
  • Fish Proteins / antagonists & inhibitors*
  • Fish Proteins / chemistry
  • Gas Chromatography-Mass Spectrometry
  • Oils, Volatile / chemistry*
  • Piper / chemistry*
  • Plant Extracts / chemistry*
  • Plant Leaves / chemistry
  • Plant Oils / chemistry
  • Plant Stems / chemistry

Substances

  • Cholinesterase Inhibitors
  • Fish Proteins
  • Oils, Volatile
  • Plant Extracts
  • Plant Oils
  • Acetylcholinesterase