Free radical scavenger properties of α-mangostin: thermodynamics and kinetics of HAT and RAF mechanisms.

Mangosteen is a tropical fruit that presents beneficial effects on human health since it is rich in anthocyanins and xanthones, which are considered bioactive compounds that have been described as good free radical scavengers. One of its most active compounds is α-mangostin. In this report, a theoretical study on the free radical scavenger capacity of α-mangostin and its monoanion is analyzed using the density functional theory approximation. Two well-known reaction mechanisms are investigated: the hydrogen atom transfer (HAT) and the radical adduct formation (RAF). Two other mechanisms are also considered: sequential electron proton Transfer (SEPT) and proton coupled electron transfer (PCET). According to thermodynamics and kinetics, α-mangostin and its deprotonated form are good free radical scavenger through the HAT mechanism, with the anionic (deprotonated) form being more reactive than the neutral one. Their capacity to scavenge OOH free radical is similar to that of carotenes, higher than that of allicin, much higher than that of melatonin and N-acetylcysteine amide, and about 15 times lower than that of 2-propenesulfenic acid.