Computational and Theoretical Chemistry
Computational and Theoretical Chemistry
4 years ago

The effects of structural properties on the methylglyoxal scavenging mechanism of flavonoid aglycones: A quantum mechanical study

The effects of structural properties on the methylglyoxal scavenging mechanism of flavonoid aglycones: A quantum mechanical study
The trapping of methylglyoxal (MGO) by flavonoid aglycones has been studied using the quantum mechanical calculations at the M06-2X/6-31g (d,p) level of theory. The process can be initiated by MGO transfer on the top of flavonoid aglycone and is sequentially continued by proton transfer from hydronium ion to flavonoid aglycone, MGO and finally a H2O molecule. With respect to the proposed mechanism, the selected flavonoid aglycones allow us to investigate the effects of some structural properties, especially the effects of hydroxyl substituents, on the MGO trapping efficacy using the energetics and results of population analysis. The nearest carbon atoms to the hydroxyl carrier carbon of ring A (C6 and C8) are suitable positions for MGO trapping; the results show that the C8 position is more active than C6 in this process. The MGO trapping efficacy strongly depends on the number of hydroxyl groups of the ring A. The energy barrier decreases with the increase in the number of intermolecular hydrogen bonds and proton transfer between the rings A and C. Although the substituents located on various rings have role on the MGO scavenging activity of flavonoid aglycones, the effects of substituents located at the rings A and C are higher than those located at B.

Publisher URL: www.sciencedirect.com/science

DOI: S2210271X17303900

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