Structure-activity relationship of antioxidant prenylated (iso)flavonoid-type compounds: quantum chemistry and molecular docking studies

Abstract

Prenylated (iso)flavonoid-type compounds are a subclass of natural flavonoids that have been reported to exhibit good antioxidant properties. In the present paper, the structure–activity relationship of three typical prenylated (iso)flavonoids namely 8-prenyldaidzein (Per), Licoflavone (Lic), and erysubin F (Ery) have been determined using DFT (density functional theory)-based calculations and molecular docking studies. As result, the CH bond of the prenyl substituent was found to be the most thermodynamically favorable site for trapping free radicals in the gas phase and lipid physiological environments. While the OH bond of the B-ring seems to be more reactive in water. HAT (hydrogen atom transfer) and SPLET (sequential proton loss electron transfer) play a decisive role in the antiradical activity of the studied compounds in lipid and polar physiological environments, respectively. All of the studied compounds exhibit strong binding affinity to both xanthine oxidase and inducible nitric oxide synthase enzymes by forming several hydrogen bonds and hydrophobic interactions with their respective catalytic sites. These results suggest that (iso)flavonoid-type compounds are promising radical scavengers and antioxidants.

Communicated by Ramaswamy H. Sarma.

Keywords:

• Prenylated (iso)flavonoids
• DFT calculations
• antioxidant activity
• structure–activity relationship
• thermodynamic study

Disclosure statement

No potential conflict of interest was reported by the author.

Additional information

Funding

Author thank MESRS (Ministère de l’Enseignement Supérieur et de la Recherche Scientifique, Algeria) and DGRSDT (Direction Générale de la Recherche Scientifique et du Développement Technologique, Algeria), for financial support, as well as the HPC resources of UCI-UFMC (Unité de Calcul Intesif of the university Fréres Mentouri Constantine 1) for the computational resource used.