Curcumin analogues with improved antioxidant properties: A theoretical exploration

Curcumin, a ubiquitous dietary molecule, is a versatile antioxidant that fights against free radicals. The antioxidant activity of curcumin and its structural analogues such as hispolon, halfcurcumin and polyhydroxycurcumin is analyzed using density functional theory (DFT). The thermochemical parameter, bond dissociation enthalpy (BDE) is used to analyse the propensity of radical attack. The hydrogen atom transfer (HAT) energetics for the hydroxyl groups of the antioxidant molecules with •OH and •OOH in both gas and solvent media are explored. Based on ourresults, hispolon and polyhydroxycurcumin characterized by multiple hydroxyl groups arranged in ortho dihydroxy fashion are good radical scavengers. Halfcurcumin exhibited comparatively similar activity as that of curcumin. The absorption properties of these molecules are in good agreement with the reported experimental findings. The molecular docking studies revealed that these antioxidants can indirectly control the oxidative stress by favourably interacting with the pro-oxidant enzyme like xanthine oxidase.