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Selection of quantum chemical descriptors by chemometric methods in the study of antioxidant activity of flavonoid compounds
Author(s) -
Weber K. C.,
Honório K. M.,
Da Silva S. L.,
Mercadante R.,
da Silva A. B. F.
Publication year - 2005
Publication title -
international journal of quantum chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.484
H-Index - 105
eISSN - 1097-461X
pISSN - 0020-7608
DOI - 10.1002/qua.20527
Subject(s) - flavonoid , chemistry , substituent , polarizability , principal component analysis , antioxidant , computational chemistry , quantitative structure–activity relationship , quantum chemical , organic chemistry , stereochemistry , molecule , computer science , artificial intelligence
In the present study, the aim was to select electronic properties responsible for free radical scavenging ability of a set of 25 flavonoid compounds employing chemometric methods. Electronic parameters were calculated using the AM1 semiempirical method, and chemometric methods (principal component analysis, hierarchical cluster analysis, and k‐nearest neighbor) were used with the aim to build models able to find relationships between electronic features and the antioxidant activity presented by the compounds studied. According to these models, four electronic variables can be considered important to discriminate more and less antioxidant flavonoid compounds: polarizability (α), charge at carbon 3 (QC3), total charge at substituent 5 (QS5), and total charge at substituent 3′ (QS3′). The features found as being responsible for the antioxidant activity of the flavonoid compounds studied are consistent with previous results found in the literature. The results obtained can also bring improvements in the search for better antioxidant flavonoid compounds. © 2005 Wiley Periodicals, Inc. Int J Quantum Chem, 2005