TY - JOUR
T1 - Quantum chemical study on the antioxidation mechanism of piceatannol and isorhapontigenin toward hydroxyl and hydroperoxyl radicals
AU - Lu, Yang
AU - Wang, Aihua
AU - Shi, Peng
AU - Zhang, Hui
AU - Li, Zesheng
N1 - Publisher Copyright:
© 2015 Lu et al. This is an open access article distributed under the terms of the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original author and source are credited.
PY - 2015/7/15
Y1 - 2015/7/15
N2 - A systematic study of the antioxidation mechanisms behind hydroxyl (·OH) and hydroperoxyl (·OOH) radical scavenging activity of piceatannol (PIC) and isorhapontigenin (ISO) was carried out using density functional theory (DFT) method. Two reaction mechanisms, abstraction (ABS) and radical adduct formation (RAF), were discussed. A total of 24 reaction pathways of scavenging ·OH and ·OOH with PIC and ISO were investigated in the gas phase and solution. The thermodynamic and kinetic properties of all pathways were calculated. Based on these results, we evaluated the antioxidant activity of every active site of PIC and ISO and compared the abilities of PIC and ISO to scavenge radicals. According to our results, PIC and ISO may act as effective ·OH and ·OOH scavengers in organism. A4-hydroxyl group is a very important active site for PIC and ISO to scavenge radicals. The introducing of -OH or -OCH3 group to the ortho-position of A4-hydroxyl group would increase its antioxidant activity. Meanwhile, the conformational effect was researched, the results suggest that the presence and pattern of intramolecular hydrogen bond (IHB) are considerable in determining the antioxidant activity of PIC and ISO.
AB - A systematic study of the antioxidation mechanisms behind hydroxyl (·OH) and hydroperoxyl (·OOH) radical scavenging activity of piceatannol (PIC) and isorhapontigenin (ISO) was carried out using density functional theory (DFT) method. Two reaction mechanisms, abstraction (ABS) and radical adduct formation (RAF), were discussed. A total of 24 reaction pathways of scavenging ·OH and ·OOH with PIC and ISO were investigated in the gas phase and solution. The thermodynamic and kinetic properties of all pathways were calculated. Based on these results, we evaluated the antioxidant activity of every active site of PIC and ISO and compared the abilities of PIC and ISO to scavenge radicals. According to our results, PIC and ISO may act as effective ·OH and ·OOH scavengers in organism. A4-hydroxyl group is a very important active site for PIC and ISO to scavenge radicals. The introducing of -OH or -OCH3 group to the ortho-position of A4-hydroxyl group would increase its antioxidant activity. Meanwhile, the conformational effect was researched, the results suggest that the presence and pattern of intramolecular hydrogen bond (IHB) are considerable in determining the antioxidant activity of PIC and ISO.
UR - https://www.scopus.com/pages/publications/84941335392
U2 - 10.1371/journal.pone.0133259
DO - 10.1371/journal.pone.0133259
M3 - Article
C2 - 26176778
AN - SCOPUS:84941335392
SN - 1932-6203
VL - 10
JO - PLoS ONE
JF - PLoS ONE
IS - 7
M1 - e0133259
ER -