Quantitative structural activity relationship of flavonoids
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Flavonoids are common antioxidants and are found in many plant species. However, only a few studies are based on quantification of structural information and bioavailability. Therefore, both QSAR (quantitative structural‐activity relationship) and QSPR (quantitative structural‐permeability relationship) study on flavonoids were conducted. In the QSAR study, flavonoid structures were obtained from the Cambridge Molecular Structure Database, minimized, and studied using Grid and Volsurf. The generated data was compared to experimental TEAC (Trolox equivalent antioxidant capacity) data from a previous study. The QSAR study found that antioxidant potential of flavonoids increases with hydrophobicity, smaller molecular weight, lack of rugosity, and increasing number of hydroxy groups. The PCA (principal components analysis) 7 component model explained 88.7% and PLS 6 component model gave an R2 value of 0.8626, showing high correlation between antioxidant potential and 23 flavonoid molecules. In the next portion of the study, a QSPR study was performed using structures from the Cambridge Software Molecular Database. After energy minimization, QSPR software, known as Volsurf, was used to generate the permeability data. This data was correlated and compared to the experimental Caco‐2 data from another study. In the QSPR study, the computational study matched with 94.1% of data determining permeability of 17 structures. In addition, smaller molecular weight and hydrophobic flavonoids showed much higher permeability than larger and hydrophilic flavonoid molecules.