The first limonoid peroxide in the Meliaceae family: walsuronoid A from Walsura robusta

Org Lett. 2007 Jun 7;9(12):2353-6. doi: 10.1021/ol070735+. Epub 2007 May 16.

Abstract

Walsuronoid A (1), a limonoid featuring an unprecedented 3,4-peroxide-bridged A-seco skeleton, together with walsuronoids B (2) and C (3) possessing a rare 18(13-->14)-abeo-limonoid skeleton, was isolated from Walsura robusta. The structures were elucidated by spectroscopic analysis and chemical correlation, and that of 1 was confirmed by single-crystal X-ray diffraction. Biosynthetic pathway of 2 and 3 was proposed and was chemically mimicked. Compounds 1 and 2 showed weak antimalarial activity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antimalarials / chemistry*
  • Antimalarials / isolation & purification
  • Antimalarials / pharmacology
  • Bridged-Ring Compounds / chemistry*
  • Bridged-Ring Compounds / isolation & purification
  • Bridged-Ring Compounds / pharmacology
  • Crystallography, X-Ray
  • Limonins / chemistry*
  • Limonins / isolation & purification
  • Limonins / pharmacology
  • Magnetic Resonance Spectroscopy / methods
  • Magnetic Resonance Spectroscopy / standards
  • Meliaceae / chemistry*
  • Microbial Sensitivity Tests
  • Models, Molecular
  • Molecular Conformation
  • Parasitic Sensitivity Tests
  • Peroxides / chemistry*
  • Peroxides / isolation & purification
  • Peroxides / pharmacology
  • Plasmodium falciparum / drug effects
  • Reference Standards
  • Sensitivity and Specificity
  • Stereoisomerism
  • Structure-Activity Relationship

Substances

  • Antimalarials
  • Bridged-Ring Compounds
  • Limonins
  • Peroxides
  • walsuronoid A
  • walsuronoid B
  • walsuronoid C