(+)- and (-)-Cajanusine, a pair of new enantiomeric stilbene dimers with a new skeleton from the leaves of Cajanus cajan

Org Lett. 2014 Jan 3;16(1):224-7. doi: 10.1021/ol403211a. Epub 2013 Dec 2.

Abstract

A pair of new enantiomeric stilbene dimers, (+)- and (-)-cajanusine [(+)-1 and (-)-1], with a unique coupling pattern were isolated from the leaves of Cajanus cajan . Their structures including absolute configurations were elucidated on the basis of comprehensive spectroscopic and single-crystal X-ray diffraction analyses, as well as CD calculations. The plausible biogenetic pathway of 1 was also proposed. Additionally, (±)-1, (+)-1, and (-)-1 exhibited inhibitory activities on the growth of human hepatocellular carcinoma cells.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents, Phytogenic / chemistry
  • Antineoplastic Agents, Phytogenic / isolation & purification
  • Antineoplastic Agents, Phytogenic / pharmacology*
  • Bridged Bicyclo Compounds
  • Cajanus / chemistry*
  • Cell Proliferation / drug effects
  • Crystallography, X-Ray
  • Dimerization
  • Dose-Response Relationship, Drug
  • Drug Screening Assays, Antitumor
  • Hep G2 Cells
  • Humans
  • Models, Molecular
  • Molecular Conformation
  • Plant Leaves / chemistry*
  • Stereoisomerism
  • Stilbenes / chemistry*
  • Stilbenes / isolation & purification
  • Stilbenes / pharmacology
  • Structure-Activity Relationship

Substances

  • Antineoplastic Agents, Phytogenic
  • Bridged Bicyclo Compounds
  • Stilbenes
  • cajanusine