Design, Synthesis and Biological Evaluation of Nitrate Derivatives of Sauropunol A and B as Potent Vasodilatory Agents

Molecules. 2019 Feb 6;24(3):583. doi: 10.3390/molecules24030583.


A group of nitrate derivatives of naturally occurring sauropunol A and B were designed and synthesized. Nitric oxide (NO) releasing capacity and vasodilatory capacity studies were performed to explore the structure-activity relationship of resulted nitrates. Biological evaluation of these compounds revealed that most of the synthesized mononitrate derivatives demonstrated superior releasing capacity than isosorbide mononitrate (ISMN), and 2MNS-6 even demonstrated stronger NO releasing capacity than isosorbide dinitrate (ISDN). Two dinitrates, DNS-1 and DNS-2, showed higher NO releasing capacity than ISDN. Evaluation of inhibitory activities to the contractions in mesenteric artery rings revealed that 2MNS-8 and DNS-2 showed stronger vasorelaxation activities than ISDN. High level of NO and soluble guanylyl cyclase (sGC) may be essential for the potent vasodilatory effect of DNS-2. The vasodilatory effects of DNS-2 may result from cellular signal transduction of NO-sGC-cGMP. DNS-2 was found to be the most potent sauropunol-derived nitrate vasodilatory agent for further pharmaceutical investigation against cardiovascular diseases.

Keywords: NO donor; NO releasing capacity; Sauropus rostratus; sauropunol A and B; vasodilatory agents.

MeSH terms

  • Animals
  • Chemistry Techniques, Synthetic
  • Drug Design*
  • In Vitro Techniques
  • Mesenteric Arteries / drug effects
  • Molecular Structure
  • Nitrates / chemical synthesis
  • Nitrates / chemistry*
  • Nitrates / pharmacology*
  • Nitric Oxide / chemistry
  • Rats
  • Structure-Activity Relationship
  • Vasodilator Agents / chemical synthesis
  • Vasodilator Agents / chemistry*
  • Vasodilator Agents / pharmacology*


  • Nitrates
  • Vasodilator Agents
  • Nitric Oxide