Chemical constituents isolated from stems of Schisandra chinensis and their antifeedant activity against Tribolium castaneum

Nat Prod Res. 2020 Sep;34(18):2595-2601. doi: 10.1080/14786419.2018.1547291. Epub 2019 Jan 9.

Abstract

One new sesquiterpene (α-iso-cubebenol acetate, 8), together with 9 known compounds (1-7, 9, 10) were isolated from the stems of Schisandra chinensis (Turcz.) Baill. by repeated silica gel column chromatography. Based on the results of MS, NMR spectra and comparing with literature data, the six dibenzocyclooctadiene lignans were identified as schizandrin A to C (1-3), schizandrin (4), schisantherin A (5) and gomisin J (6), the two sesquiterpenes were identified as α-iso-cubebenol (7) and α-iso-cubebenol acetate (8), while the two triterpenic acids were identified as ganwuweizic acid (9) and kadsuric acid (10). The antifeedant activity of the 10 compounds against Tribolium castaneum adults was tested. Gomisin J (6) exhibited activity at 1500 ppm concentration with 40.3% antifeeding index percentages. As for the dibenzocyclooctene lignans (compounds 1-3, 6), the number of methylenedioxies and the position of hydroxyl groups were the main factors to affect their antifeedant activities.

Keywords: Schisandra chinensis (Turcz.) Baill; Tribolium castaneum; antifeedant activity; dibenzocyclooctadiene lignans; α-iso-cubebenol acetate.

MeSH terms

  • Animals
  • Cyclooctanes / analysis
  • Cyclooctanes / chemistry*
  • Cyclooctanes / isolation & purification
  • Dioxoles / isolation & purification
  • Feeding Behavior / drug effects*
  • Lignans / analysis
  • Lignans / chemistry*
  • Lignans / isolation & purification
  • Plant Stems / chemistry*
  • Polycyclic Compounds / isolation & purification
  • Schisandra / chemistry*
  • Sesquiterpenes / analysis
  • Sesquiterpenes / isolation & purification
  • Structure-Activity Relationship
  • Tribolium* / drug effects
  • Triterpenes / analysis
  • Triterpenes / isolation & purification

Substances

  • Cyclooctanes
  • Dioxoles
  • Lignans
  • Polycyclic Compounds
  • Sesquiterpenes
  • Triterpenes
  • alpha-iso-cubebenol
  • dibenzocyclooctadiene lignan
  • schizandrin A
  • schizandrer A
  • schizandrin
  • gomisin J