Design, synthesis, and antiviral activity of novel rutin derivatives containing 1, 4-pentadien-3-one moiety

Eur J Med Chem. 2015 Mar 6:92:732-7. doi: 10.1016/j.ejmech.2015.01.017. Epub 2015 Jan 10.

Abstract

Rutin (compound 5) and some compounds (compounds 1-4 and 6) were isolated from Artemisia princeps Pamp (A. princeps Pamp.) and a series of novel rutin derivatives containing 1,4-pentadien-3-one moiety were designed and synthesized. The target compounds were characterized by proton nuclear magnetic resonance spectroscopy ((1)H NMR), carbon nuclear magnetic resonance spectroscopy ((13)C NMR), and ESI-MS. Bioassay results indicated that some of the compounds showed good to excellent antiviral activities against tobacco mosaic virus (TMV) and cucumber mosaic virus (CMV) at 500 μg/mL in vivo. The 50% effective concentrations (EC50) of the compound 7r against CMV was 394.78 μg/mL, which was better than that of Ningnanmycin (432.22 μg/mL). These results indicated that novel rutin derivatives containing 1,4-pentadien-3-one moiety can effectively control CMV.

Keywords: 1,4-pentadien-3-one; Antiviral activity; Artemisia princeps Pamp.; Cucumber mosaic virus; Rutin; Tobacco mosaic virus.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkadienes / chemistry*
  • Antiviral Agents / chemical synthesis*
  • Antiviral Agents / chemistry
  • Antiviral Agents / pharmacology*
  • Cucumovirus / drug effects*
  • Dose-Response Relationship, Drug
  • Drug Design*
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Pentanones / chemistry*
  • Rutin / chemical synthesis*
  • Rutin / chemistry
  • Rutin / pharmacology*
  • Structure-Activity Relationship
  • Tobacco Mosaic Virus / drug effects*

Substances

  • Alkadienes
  • Antiviral Agents
  • Pentanones
  • Rutin