Synthesis of eugenol-derived glucosides and evaluation of their ability in inhibiting the angiotensin converting enzyme
Dalila Junqueira Alvarenga, Laira Maria Faria Matias, Cleydson Finotti Cordeiro, Thiago Belarmino de Souza, Stefânia Neiva Lavorato, Marília Gabriella Alves Goulart Pereira, Danielle Ferreira Dias, Diogo Teixeira Carvalho · Natural Product Research · 2020
We report here a series of glucosides which are active as inhibitors of the angiotensin converting enzyme (ACE). They are structurally related to the natural compound eugenol and exhibited significant inhibition values. Their syntheses were expeditious and we could obtain informative docking plots of them complexed to this enzyme. A glucoside derived from eugenol, carrying a carboxylic group in the aglycone, was the most active of them (with an IC50 of 0.4 mM) and showed good binding energies in docking studies with ACE. Moreover, computational prediction of toxicity risks, physicochemical properties and drug score show that the glucoside derivative of eugenol is a suitable compound for optimisation studies aimed at finding new drug candidates.