Biomimetic synthesis of active isorhapontigenin dimers

J Asian Nat Prod Res. 2014;16(5):511-21. doi: 10.1080/10286020.2014.913030. Epub 2014 May 2.

Abstract

Synthetic isorhapontigenin was treated with several kinds of inorganic reagents and peroxidase so as to prepare active stilbene dimers. Among them, silver acetate in methanol gave two new isorhapontigenin dimers 4 and 5, together with four known natural stilbene dimers 2, 3, 6, and 7. Their structures and relative configurations were determined on the basis of spectral analysis, and their possible formation mechanisms were discussed, respectively. Compounds 2, 6, and 7 were artificially synthesized for the first time. All the products were evaluated for anti-inflammatory activities.

Keywords: biomimetic synthesis; isorhapontigenin; silver acetate; stilbene dimer.

MeSH terms

  • Anti-Inflammatory Agents / chemical synthesis*
  • Anti-Inflammatory Agents / chemistry*
  • Anti-Inflammatory Agents / pharmacology
  • Biomimetics
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Peroxidase / chemistry
  • Stilbenes / chemical synthesis*
  • Stilbenes / chemistry*
  • Stilbenes / pharmacology

Substances

  • Anti-Inflammatory Agents
  • Stilbenes
  • isorhapontigenin
  • Peroxidase