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Molecules 2012, 17(11), 12910-12924; doi:10.3390/molecules171112910

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

1,†,* , 2,†
1 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 2 Department of Food Science and Engineering, School of Food and Biological Engineering, Jiangsu University, Zhenjiang 212013, China 3 College of Food Science, South China Agricultural University, Guangzhou 510642, China 4 College of Food Science, Fujian Agriculture and Forestry University, Fuzhou 350002, China These authors contributed equally to this work.
* Author to whom correspondence should be addressed.
Received: 15 October 2012 / Revised: 15 October 2012 / Accepted: 26 October 2012 / Published: 1 November 2012
(This article belongs to the Section Medicinal Chemistry)
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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 r2pred = 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.
Keywords: 3D-QSAR; phenolic acids; free radical scavenging; structure; CoMFA; CoMSIA 3D-QSAR; phenolic acids; free radical scavenging; structure; CoMFA; CoMSIA
This is an open access article distributed under the Creative Commons Attribution License (CC BY) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Jing, P.; Zhao, S.-J.; Jian, W.-J.; Qian, B.-J.; Dong, Y.; Pang, J. Quantitative Studies on Structure-DPPH• Scavenging Activity Relationships of Food Phenolic Acids. Molecules 2012, 17, 12910-12924.

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