Synthesis of eugenol-derived glucosides and evaluation of their ability in inhibiting the angiotensin converting enzyme

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 o...

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Bibliographic Details
Published in:Natural product research 2022-05, Vol.36 (9), p.2246-2253
Main Authors: Alvarenga, Dalila Junqueira, Matias, Laira Maria Faria, Cordeiro, Cleydson Finotti, Souza, Thiago Belarmino de, Lavorato, Stefânia Neiva, Pereira, Marília Gabriella Alves Goulart, Dias, Danielle Ferreira, Carvalho, Diogo Teixeira
Format: Article
Language:English
Subjects:
angiotensin converting enzyme
Angiotensin-Converting Enzyme Inhibitors - chemistry
Angiotensin-Converting Enzyme Inhibitors - pharmacology
enzyme inhibitors
eugenol
Eugenol - pharmacology
Glucosides
Glucosides - chemistry
Glucosides - pharmacology
Molecular Docking Simulation
Peptidyl-Dipeptidase A - chemistry
Peptidyl-Dipeptidase A - metabolism
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Summary: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 IC 50 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.
ISSN:1478-6419
1478-6427
DOI:10.1080/14786419.2020.1827399