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- Title
Quantitative Studies on Structure-DPPH• Scavenging Activity Relationships of Food Phenolic Acids.
- Authors
Pu Jing; Shu-Juan Zhao; Wen-Jie Jian; Bing-Jun Qian; Ying Dong; Jie Pang
- Abstract
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.
- Subjects
PHENOLIC acids; ANTIOXIDANTS; HYDROPHOBIC compounds; ELECTRON donor-acceptor complexes; FREE radical scavengers
- Publication
Molecules, 2012, Vol 17, Issue 11, p12910
- ISSN
1420-3049
- Publication type
Article
- DOI
10.3390/molecules171112910