Semiempirical molecular modeling into quercetin reactive site: structural, conformational, and electronic features.
The conformational behavior, molecular geometry and electronic structure of quercetin were investigated using the semiempirical AM1 and PM3 methods. Results reveal that quercetin has a nonplanar molecular structure, with cross-conjugation occurring at the C ring. Calculations were also performed for quercetin radical species at the OH groups, showing the presence of three radicals in a narrow range of energy. An interpretation of the antioxidative process mechanism, exerted by quercetin as a free radical scavenger, relies on two isoenergetic radicals with extended electronic delocalization between adjacent rings, also having cross-conjugated systems and being affected by the experimental environment influencing their relative order.
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CIRASAIA, Mediterranean Agrifood Research Centre, and Dipartimento di Chimica, Universita' della Calabria, Arcavacata di Rende (CS), Italy.
Toscano
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Uccella
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D004583:Electrons; D008958:Models, Molecular; D008968:Molecular Conformation; D011794:Quercetin / Q000737:chemistry*
D011794:Quercetin