Comparison of the Antioxidant Effects of Quercitrin and Isoquercitrin: Understanding the Role of the 6″-OH GroupReportar como inadecuado


Comparison of the Antioxidant Effects of Quercitrin and Isoquercitrin: Understanding the Role of the 6″-OH Group


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1

School of Chinese Herbal Medicine, Guangzhou University of Chinese Medicine, Waihuan East Road No. 232, Guangzhou Higher Education Mega Center, Guangzhou 510006, China

2

School of Basic Medical Science, Guangzhou University of Chinese Medicine, Waihuan East Road No. 232, Guangzhou Higher Education Mega Center, Guangzhou 510006, China





*

Authors to whom correspondence should be addressed.



Academic Editor: Maurizio Battino

Abstract The role of the 6″-OH ω-OH group in the antioxidant activity of flavonoid glycosides has been largely overlooked. Herein, we selected quercitrin quercetin-3-O-rhamnoside and isoquercitrin quercetin-3-O-glucoside as model compounds to investigate the role of the 6″-OH group in several antioxidant pathways, including Fe2+-binding, hydrogen-donating H-donating, and electron-transfer ET. The results revealed that quercitrin and isoquercitrin both exhibited dose-dependent antioxidant activities. However, isoquercitrin showed higher levels of activity than quercitrin in the Fe2+-binding, ET-based ferric ion reducing antioxidant power, and multi-pathways-based superoxide anion-scavenging assays. In contrast, quercitrin exhibited greater activity than isoquercitrin in an H-donating-based 1,1-diphenyl-2-picrylhydrazyl radical-scavenging assay. Finally, in a 3-4,5-dimethylthiazol-2-yl-2,5-diphenyl assay based on an oxidatively damaged mesenchymal stem cell MSC model, isoquercitrin performed more effectively as a cytoprotector than quercitrin. Based on these results, we concluded that 1 quercitrin and isoquercitrin can both indirectly i.e., Fe2+-chelating or Fe2+-binding and directly participate in the scavenging of reactive oxygen species ROS to protect MSCs against ROS-induced oxidative damage; 2 the 6″-OH group in isoquercitrin enhanced its ET and Fe2+-chelating abilities and lowered its H-donating abilities via steric hindrance or H-bonding compared with quercitrin; and 3 isoquercitrin exhibited higher ROS scavenging activity than quercitrin, allowing it to improve protect MSCs against ROS-induced oxidative damage. View Full-Text

Keywords: quercitrin; isoquercitrin; Q3G; 6″-OH; ω-OH; flavonoid glycoside; antioxidant mechanisms; mesenchymal stem cells quercitrin; isoquercitrin; Q3G; 6″-OH; ω-OH; flavonoid glycoside; antioxidant mechanisms; mesenchymal stem cells





Autor: Xican Li 1,* , Qian Jiang 1, Tingting Wang 1, Jingjing Liu 1 and Dongfeng Chen 2,*

Fuente: http://mdpi.com/



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