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On the Novel ETE2 and BDE2 Molecular Descriptors of Flavonoid Free Radical Scavenging Potency

Thermodynamic aspects of the first 1H+/1e– (flavonoid  flavonoid phenoxyl radical) and the second 1H+/1e (flavonoid phenoxyl radical  quinone) free radical scavenging processes of flavonoids were computationally studied for aqueous and lipid media using the newly developed PM7 method. We found that the predictive potency of descriptors related to the energetics of the second 1H+/1e– free radical scavenging processes resulting in quinone formation (electron transfer enthalpy (ETE2) related to electron transfer from flavonoid phenoxide anion radical, and the O–H bond dissociation enthalpy (BDE2) related to H- atom transfer from flavonoid phenoxyl radical) are superior to the currently used indices related to the first 1H+/1e– processes. The ETE2 (in polar medium) and BDE2 (in non-polar medium) effectively discriminate the high active from low active flavonoids and could serve as primary descriptors in development of the antiradical QSAR (quantitative structure-activity relationships) of flavonoids.

Flavonoid ; Radical scavenging ; QSAR ; bond dissociation enthalpy ; electron transfer enthalpy

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