Schisandrene, a dibenzocyclooctadiene lignan from Schisandra chinensis: structure-antioxidant activity relationships of dibenzocyclooctadiene lignans

J Nat Prod. 2006 Mar;69(3):356-9. doi: 10.1021/np0503707.

Abstract

Phytochemical investigation of the fruits of Schisandra chinensis led to the isolation of 13 lignans including schisandrene (13), a new lignan based on a dibenzocyclooctadiene backbone with an exocyclic double bond. Its structure and absolute configuration were established using NMR, MS, and CD data. Antioxidant activity of the lignans was evaluated using a DCFH-DA cellular-based assay. The structure-activity relationships of the dibenzocyclooctadiene lignans showed that the exocyclic methylene functionality was essential for antioxidant activity, with the benzoyloxy group probably enhancing such effects.

Publication types

  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Antioxidants* / chemistry
  • Antioxidants* / isolation & purification
  • Antioxidants* / pharmacology
  • Cyclooctanes* / chemistry
  • Cyclooctanes* / isolation & purification
  • Cyclooctanes* / pharmacology
  • Korea
  • Lignans* / chemistry
  • Lignans* / isolation & purification
  • Lignans* / pharmacology
  • Molecular Structure
  • Plants, Medicinal / chemistry*
  • Schisandra / chemistry*
  • Structure-Activity Relationship

Substances

  • Antioxidants
  • Cyclooctanes
  • Lignans
  • schisandrene