Synthesis and Characterization of New Stilbenoid Derivatives as Potential Vasodilators

  • Sock Ying Chan School of Chemical Sciences, Universiti Sains Malaysia, 11800 USM, Pulau Pinang, Malaysia
  • Chuan Wei Oo School of Chemical Sciences, Universiti Sains Malaysia, 11800 USM, Pulau Pinang, Malaysia
  • Mun Fei Yam School of Pharmaceutical Sciences, Universiti Sains Malaysia, 11800 USM, Pulau Pinang, Malaysia
  • Yean Chun Loh School of Chemical Sciences, Universiti Sains Malaysia, 11800 USM, Pulau Pinang, Malaysia
Keywords: Stilbenoids; In vitro aortic ring assays; Wittig reaction; resveratrol; vasodilator; antihypertensive

Abstract

The development of antihypertensive drug has become a major concern in pharmacological and medical fields as hypertension is always related to many chronic diseases such as stroke and other coronary diseases. Stilbenoids, such as resveratrol, have been reported for their potency as vasodilators that are able to work directly on the muscles in blood vessel walls by dilating and preventing the tightening of blood vessels. In this study, a series of new stilbenoid derivatives with different positions and numbers of the ethoxy group have been synthesized via Wittig reaction using commercially available dihydroxybenzoic acids and hydroxybenzaldehydes; the trans isomers were then isolated and purified using column chromatography technique. The chemical structures of the synthesized stilbenoid derivatives were characterized by FT-IR, 1H-NMR and 13C-NMR spectroscopy. In vitro aortic ring assays were conducted to evaluate the vasodilatory potential of the synthesized stilbenoid derivatives on endothelium-intact aortic rings isolated from male Sprague Dawley (SD) rats. It was found that all the newly synthesized stilbenoid derivatives possessed vasodilatory properties. Compound 12a with 2, 3, and 4′ ethoxy substitutions showed the highest Rmax value of  25.99 ± 4.39% compared to the other stilbenoid derivatives.

Published
2020-03-24