Schilancitrilactones A-C: three unique nortriterpenoids from Schisandra lancifolia

Org Lett. 2012 Mar 2;14(5):1286-9. doi: 10.1021/ol300099e. Epub 2012 Feb 16.

Abstract

Three unique nortriterpenoids, schilancitrilactones A-C (1-3), were isolated from the stems of Schisandra lancifolia . Compound 1 possesses a 5/5/7/5/5/5-fused hexacyclic ring system with a C(29) backbone, while 2 and 3 feature a C(27) skeleton with a 5/7/5/5/5-fused pentacyclic ring system. Their absolute stereochemistries were established by CD and single-crystal X-ray diffraction experiments. Compound 3 showed anti-HIV-1 activity with an EC(50) value of 27.54 μg/mL, and 1 exhibited antifeedant activity at 15.73 μg/cm(2).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-HIV Agents / chemistry*
  • Anti-HIV Agents / isolation & purification
  • Anti-HIV Agents / pharmacology
  • HIV-1 / drug effects
  • Models, Molecular
  • Schisandra / chemistry*
  • Triterpenes / chemistry*
  • Triterpenes / isolation & purification
  • Triterpenes / pharmacology

Substances

  • Anti-HIV Agents
  • Triterpenes
  • schilancitrilactone A
  • schilancitrilactone B
  • schilancitrilactone C