The basic antioxidant structure for flavonoid derivatives

• Published in: Journal of molecular modeling 2012-09, Vol.18 (9), p.4073-4080
• Main Authors: Mendes, Anna P. S., Borges, Rosivaldo S., Neto, Antonio M. J. Chaves, de Macedo, Luiz G. M., da Silva, Albérico B. F.
• Format: Article
• Language: English
• Subjects: Antioxidants - chemistry; Cations; Characterization and Evaluation of Materials; Chemistry; Chemistry and Materials Science; Computer Appl. in Life Sciences; Computer Applications in Chemistry; Flavonoids - chemistry; Free Radicals - chemistry; Models, Molecular; Molecular Medicine; Original Paper; Structure-Activity Relationship; Theoretical and Computational Chemistry
• ISSN: 1610-2940; 0948-5023
• DOI: 10.1007/s00894-012-1397-0

An antioxidant structure–activity study is carried out in this work with ten flavonoid compounds using quantum chemistry calculations with the functional of density theory method. According to the geometry obtained by using the B3LYP/6-31G(d) method, the HOMO, ionization potential, stabilization energies, and spin density distribution showed that the flavonol is the more antioxidant nucleus. The spin density contribution is determinant for the stability of the free radical. The number of resonance structures is related to the π-type electron system. 3-hydroxyflavone is the basic antioxidant structure for the simplified flavonoids studied here. The electron abstraction is more favored in the molecules where ether group and 3-hydroxyl are present, nonetheless 2,3-double bond and carbonyl moiety are facultative. Figure The basic antioxidant structure for flavonoid derivatives