Coumarin Derivatives Containing Sulfonamide and Dithioacetal Moieties: Design, Synthesis, Antiviral Activity, and Mechanism

J Agric Food Chem. 2022 May 18;70(19):5773-5783. doi: 10.1021/acs.jafc.2c00672. Epub 2022 May 9.

Abstract

Cucumber mosaic virus (CMV) is currently a known plant virus with the most hosts, broadest distribution, and economic hazard. To develop new antiviral drugs against this serious virus, a new range of coumarin derivatives containing sulfonamide and dithioacetal structures were designed and synthesized, and their anti-CMV activities were detected by the half-leaf dead spot method. The results of the biological activity assay showed that most of the compounds exhibited outstanding anti-CMV activity. Especially, compound C23 displayed the optimal in vivo anti-CMV activity, with an EC50 value of 128 μg/mL, which was remarkably better than that of COS (781 μg/mL) and ningnanmycin (436 μg/mL). Excitingly, we found that compound C23 could be a promising plant activator that significantly increased defense-related enzyme activities and the tobacco chlorophyll content. Furthermore, compound C23 enhanced defense responses against viral infection by inducing the abscisic acid (ABA) pathway in tobacco. This work established a basis for multifunction pesticide discovery involving mechanism of action study and structure optimization.

Keywords: ABA; coumarin; cucumber mosaic virus; dithioacetal; plant resistance; sulfonamide.

MeSH terms

  • Antiviral Agents / chemistry
  • Coumarins / pharmacology
  • Cucumovirus*
  • Drug Design
  • Nicotiana
  • Structure-Activity Relationship
  • Sulfonamides / pharmacology
  • Tobacco Mosaic Virus*

Substances

  • Antiviral Agents
  • Coumarins
  • Sulfonamides