Abstract
Radical scavenging activity of anthocyanins is well known, but only a few studies have been conducted by quantum chemical approach. The adaptive neuro-fuzzy inference system (ANFIS) is an effective technique for solving problems with uncertainty. The purpose of this study was to construct and evaluate quantitative structure-activity relationship (QSAR) models for predicting radical scavenging activities of anthocyanins with good prediction efficiency. ANFIS-applied QSAR models were developed by using quantum chemical descriptors of anthocyanins calculated by semi-empirical PM6 and PM7 methods. Electron affinity (A) and electronegativity (χ) of flavylium cation, and ionization potential (I) of quinoidal base were significantly correlated with radical scavenging activities of anthocyanins. These descriptors were used as independent variables for QSAR models. ANFIS models with two triangular-shaped input fuzzy functions for each independent variable were constructed and optimized by 100 learning epochs. The constructed models using descriptors calculated by both PM6 and PM7 had good prediction efficiency with Q-square of 0.82 and 0.86, respectively.
Highlights
As constituents of flavonoid group, anthocyanins and their aglycones, anthocyanidins, are color pigments originated from plants
In the case of quinoidal base (QB), QB7 was suggested as a primary contributor for radical scavenging activities, because higher correlation was observed between quantum chemical descriptors of QB7 and radical scavenging activities compared with QB4'
Semi-empirical quantum chemical calculations of anthocyanins were done by PM6 and PM7 methods using MOPAC2012
Summary
As constituents of flavonoid group, anthocyanins and their aglycones, anthocyanidins, are color pigments originated from plants. Anthocyanins basically have flavylium ion skeleton attached with different side groups including hydrogen atom, hydroxyl group, and methoxy group. Radical scavenging activity is one of the characteristics of anthocyanins and other flavonoids. These compounds can reduce reactive oxygen species (ROS), resulting in relieving oxidative stress [1,2]. The radical scavenging activities can be explained by two suggested mechanisms: One is hydrogen atom transfer (HAT) and the other is single electron transfer (SET) [3]. HAT-based radical scavenging activity is explained by hydrogen donation as following equation: X· + AH → XH + A·
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