The radical scavenging activity of moracins: theoretical insights

© The Royal Society of Chemistry. Moracins are natural products that have been isolated from different plants such as Artocarpus heterophyllus, Cassia fistula, Morus alba, and Morus mesozygia. Studies showed that moracins may have various advantageous physiological effects such as anticancer, anti-inflammatory, anticholinesterase and particularly antioxidant activities. Most of these bioactivities have not been studied systematically. In this study, the radical scavenging of a typical moracin (moracin M, MM) against HO and HOO radicals was evaluated by thermodynamic and kinetic calculations in the gas phase as well as in water and pentyl ethanoate solvents. It was found that the overall rate constants for the HO radical scavenging in the gas phase and the physiological environments are in the range of 1011 to 1010 M-1 s-1, respectively. For the HOO + MM reaction the rate constants are 4.10 × 107 and 3.80 × 104 M-1 s-1 in the polar and lipid media, respectively. It is important to notice that the single electron transfer pathway of the anion state (MM-O6′-) dominated the HOO radical scavenging in the aqueous solution, whereas in lipid medium the neutral MM exerted its activity by the formal hydrogen transfer mechanism. The HOO radical scavenging of MM is comparable to that of Trolox in lipid medium, whereas it is 315.4 times more active in the polar environment.