Study of Coumarin-Resveratrol Hybrids as Potent Antioxidant Compounds

Abstract

Abstract:In the present work we synthesized a selected series of hydroxylated 3-phenylcoumarins 5-8, with the aim of evaluating in detail their antioxidant properties. From an in depth study of the antioxidant capacity data (ORAC-FL, ESR, CV and ROS inhibition) it was concluded that these derivatives are very good antioxidants, with very interesting profiles in all the performed assays. The study of the effect of the number and position of the hydroxyl groups on the antioxidant activity was the principal aim of this study. In particular, 7-hydroxy-3-(3'-hydroxy)phenylcoumarin (8) proved to be the most active and effective antioxidant of the selected series in four of the performed assays (ORAC-FL = 11.8, capacity of scavenging hydroxyl radicals = 54%, Trolox index = 2.33 and AI30 index = 0.18). However, the presence of two hydroxyl groups on this molecule did not increase greatly the activity profile. Theoretical evaluation of ADME properties of all the derivatives was also carried out. All the compounds can act as potential candidates for preventing or minimizing the free radical overproduction in oxidative-stress related diseases. OPEN ACCESSMolecules 2015, 20 3291These preliminary findings encourage us to perform a future structural optimization of this family of compounds.

Evaluation of Antioxidant and Antitrypanosomal Properties of a Selected Series of Synthetic 3‐Carboxamidocoumarins

“…The electrochemical behaviour of the compounds was also studied. The study of the electrochemical anodic behaviour of the compounds was based principally in previous studies that related low oxidation potential to high antioxidant capacity . ORAC‐FL, ESR reactivity and CV assays were the techniques used to achieve the main goals of this project.…”

Recent Advances in the Synthesis of Coumarin Derivatives from Different Starting Materials

“…Obtained products were hydroxylated under reflux in the presence of aqueous hydrochloric acid and MeOH (Scheme 27). Matos et al developed efficient two-step synthesis of hydroxylated 3-phenylcoumarins [50]. Initially, acetoxy-3-phenylcoumarins were synthesized in the reaction of salicylaldehydes and phenylacetic acid in the presence of anhydrous potassium acetate (CH 3 CO 2 K) and acetic anhydride.…”

“…Coumarins possess antimicrobial activity such as antibacterial [38][39][40][41][42][43][44] and antifungal [40,[45][46][47][48]. Numerous coumarin derivatives showed significant antioxidant activity [49][50][51][52][53]. Some coumarins are derived as acetylcholinesterase (AchE) inhibitors, which could be considered as a drug in Alzheimer disease treatment [54][55][56].…”

THE ANTI-OXIDANT ACTIVITIES OF ETHANOL EXTRACT OF MAHOGANY (Sweitenia mahagoni Jacq.) SEEDS IN THE LIVER TISSUES OF DIABETIC EXPERIMENTAL RATS

“…These results are suspected to be related to the compounds contained in the ethanol mahogany seed extract, namely flavonoids (Wresdiyati et al, 2015). Flavonoids are potential anti-oxidant by eliminating excess free radical compounds (Matos et al, 2015), so that MDA production as lipid peroxidation products can be suppressed. MDA levels have been widely used as an indicator of the occurrence of oxidative damage, because MDA is the final product of lipid peroxidation produced by oxidation by free radicals (Tiwari et al, 2013).…”