Quantitative Studies on Structure-DPPH• Scavenging Activity Relationships of Food Phenolic Acids

Molecules

Pu Jing²  Shu-Juan Zhao¹  Wen-Jie Jian³  Bing-Jun Qian²  Ying Dong¹ 

[1] Department of Food Science and Engineering, School of Food and Biological Engineering, Jiangsu University, Zhenjiang 212013, China;Research Center for Food Safety and Nutrition, Key Lab of Urban Agriculture (South), Bor S. Luh Food Safety Research Center, School of Agriculture & Biology, Shanghai Jiao Tong University, Shanghai 200240, China;College of Food Science, South China Agricultural University, Guangzhou 510642, China;

关键词: 3D-QSAR;    phenolic acids;    free radical scavenging;    structure;    CoMFA;    CoMSIA;   

DOI  :  10.3390/molecules171112910

来源: mdpi

【 摘 要 】

Phenolic acids are potent antioxidants, yet the quantitative structure-activity relationships of phenolic acids remain unclear. The purpose of this study was to establish 3D-QSAR models able to predict phenolic acids with high DPPH• scavenging activity and understand their structure-activity relationships. The model has been established by using a training set of compounds with cross-validated q² = 0.638/0.855, non-cross-validated r² = 0.984/0.986, standard error of estimate = 0.236/0.216, and F = 139.126/208.320 for the best CoMFA/CoMSIA models. The predictive ability of the models was validated with the correlation coefficient r²_pred = 0.971/0.996 (>0.6) for each model. Additionally, the contour map results suggested that structural characteristics of phenolics acids favorable for the high DPPH• scavenging activity might include: (1) bulky and/or electron-donating substituent groups on the phenol ring; (2) electron-donating groups at the meta-position and/or hydrophobic groups at the meta-/ortho-position; (3) hydrogen-bond donor/electron-donating groups at the ortho-position. The results have been confirmed based on structural analyses of phenolic acids and their DPPH• scavenging data from eight recent publications. The findings may provide deeper insight into the antioxidant mechanisms and provide useful information for selecting phenolic acids for free radical scavenging properties.

【 授权许可】

CC BY   
© 2012 by the authors; licensee MDPI, Basel, Switzerland.