Chiral resolution and absolute configuration of a pair of rare racemic spirodienone sesquineolignans from Xanthium sibiricum

Org Lett. 2014 Oct 17;16(20):5406-9. doi: 10.1021/ol502649a. Epub 2014 Oct 2.

Abstract

A pair of racemic spirodienone neolignan enantiomers, (±)-sibiricumin A, were isolated from the extract of the fruits of Xanthium sibiricum. The resolution of (+)- and (-)-sibiricumin A was achieved by chiral HPLC. The absolute configurations of the racemes were assigned by X-ray and by electronic circular dichroism (ECD). This experiment is the first unambiguous determination of the absolute configuration of spirodienone neolignan.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Chromatography, High Pressure Liquid
  • Circular Dichroism
  • Crystallography, X-Ray
  • Leukocytes / drug effects
  • Lignans / chemistry
  • Lignans / isolation & purification*
  • Lipopolysaccharides / pharmacology
  • Molecular Conformation
  • Molecular Structure
  • Nitric Oxide / biosynthesis
  • Rats
  • Spiro Compounds / chemistry
  • Spiro Compounds / isolation & purification*
  • Stereoisomerism
  • Xanthium / chemistry*

Substances

  • Lignans
  • Lipopolysaccharides
  • Spiro Compounds
  • sibiricumin A
  • Nitric Oxide