Alkylated Sesamol Derivatives as Potent Antioxidants

Abstract

Sesamol is a phenolic derivative. Its antioxidant activity is low than that of Trolox and depends on benzodioxole moiety. Thus, a molecular modification strategy through alkylation, inspired by natural and synthetic antioxidants, was studied by molecular modeling at the DFT/B3LYP level of theory by comparing the 6-31+G(d,p) and 6-311++G(2d,2p) basis sets. All proposed derivatives were compared to classical related antioxidants such as Trolox, t-butylated hydroxytoluene (BHT) and t-butylated hydroxyanisole (BHA). According to our results, molecular orbitals, single electron or hydrogen-atom transfers, spin density distributions, and alkyl substitutions at the ortho positions related to phenol moiety were found to be more effective than any other positions. The trimethylated derivative was more potent than Trolox. t-Butylated derivatives were stronger than all other alkylated derivatives and may be new alternative forms of modified antioxidants from natural products with applications in the chemical, pharmaceutical, and food industries.

Increasing Reduction Potentials of Type 1 Copper Center and Catalytic Efficiency of Small Laccase from Streptomyces coelicolor through Secondary Coordination Sphere Mutations

“…Laccases from white‐rot fungi are a group of high reduction potential laccases (HRPLs) which exhibit E °′ T1Cu between 730–790 mV vs. SHE (all potentials described in this work are vs. SHE) [25] . Previous studies have attributed the high activity and low ORR overpotentials in HRPLs to a high E °′ T1Cu [23,26–30] . However, HRPLs are heavily glycosylated and their activity has been shown to be affected by the level of glycosylation [31–33] .…”

Ir(iii)/Ag(i)-catalyzed directly C–H amidation of arenes with OH-free hydroxyamides as amidating agents

“…Pyrazole and its derivatives play crucial roles in organic and pharmaceutical fields, because of their unique five-membered nitrogen-containing heterocyclic structures. 1 In synthetic chemistry, pyrazole and its derivatives are not only efficiently and conveniently synthesized, but also further transformed into more complex artificial molecules. 2 In the continuous development of coordination chemistry, various complexes containing pyrazole ligands have also been synthesized, characterized, and further applied.…”

Palladium‐catalyzed synthesis of Benzoannulated spiroketal lactones derived from cholesterol: NMR characterization and crystal structures

“…Provided that the cell membranes consist of a lipid bilayer formed by an arrangement of cholesterol molecules positioned between the phospholipids [7], the presence of lipophilic cholestane skeleton of compounds 1a , b may facilitate the permeability through the membrane allowing a more efficient intracellular release of the compounds, in such a way that they can exert their effects on cells [7].…”