Journal
FOOD CHEMISTRY
Volume 152, Issue -, Pages 578-585Publisher
ELSEVIER SCI LTD
DOI: 10.1016/j.foodchem.2013.12.025
Keywords
Flavonoid; Radical scavenging; QSAR; Double PCET; BDE; ETE
Funding
- Ministry of Science, Education and Sports of the Republic of Croatia [079-0000000-3211, 098-1770495-2919, 098-0982464-2511]
- Ministry of Science of the Republic of Serbia [174028, 172015]
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The 1H(+)/1e(-) and 2H(+)/2e(-) proton-coupled electron transfer (PCET) processes of free radical scavenging by flavonoids were theoretically studied for aqueous and lipid environments using the PM6 and PM7 methods. The results reported here indicate that the significant contribution of the second PCET mechanism, resulting in the formation of a quinone/quinone methide, effectively discriminates the active from inactive flavonoids. The predictive potency of descriptors related to the energetics of second PCET mechanisms (the second O-H bond dissociation enthalpy (BDE2) related to hydrogen atom transfer (HAT) mechanism, and the second electron transfer enthalpy (ETE2) related to sequential proton loss electron transfer (SPLET) mechanism) are superior to the currently used indices, which are related to the first 1H(+)/1e(-) processes, and could serve as primary descriptors in development of the QSAR (quantitative structure-activity relationships) of flavonoids. (C) 2013 Elsevier Ltd. All rights reserved.
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