Chemoinformatic modelling of the antioxidant activity of phenolic compounds.

BACKGROUND: Antioxidants are chemicals used to protect foods from deterioration by neutralizing free radicals and inhibiting the oxidative process. One approach to investigate the antioxidant activity is to develop quantitative structure-activity relationships (QSARs). RESULTS: A curated database of 165 structurally heterogeneous phenolic compounds with the Trolox equivalent antioxidant capacity (TEAC) was developed. Molecular geometries were optimized by means of the GFN2-xTB semiempirical method and diverse molecular descriptors were obtained afterwards. For model development, V-WSP unsupervised variable reduction was used before performing the genetic algorithms-variable subset selection (GAs-VSS) to construct the best five-descriptor multiple linear regression model. The coefficient of determination and the root mean square error were used to measure the performance in calibration (R2 = 0.789 and RMSEC = 0.381), and test set prediction (Q2 = 0.748 and RMSEP = 0.416), along several cross-validation criteria. To thoroughly understand the TEAC prediction, a fully explained mechanism of action of the descriptors is provided. In addition, the applicability domain of the model defined a theoretical chemical space for reliable predictions of new phenolic compounds. CONCLUSION: This in silico model conforms to the five principles stated by the Organisation for Economic Co-operation and Development. The model might be useful for virtual screening of the antioxidant chemical space and for identifying the most potent molecules related to an experimental measurement of TEAC activity. In addition, the model could assist chemists working on computer-aided drug design for the synthesis of new targets with improved activity and potential uses in food science. © 2023 Society of Chemical Industry.

Carrot fiber (CF) composite films for antioxidant preservation: Particle size effect.

The effect of particle size (53, 105 and 210 µm) of carrot fiber (CF) on their hydration properties and antioxidant capacity as well as on the performance of the CF-composite films developed with commercial low methoxyl pectin (LMP) was studied. It was determined that CF contained carotenoids and phenolics co-extracted with polysaccharides (80%), rich in pectins (15%). CF showed antioxidant activity and produced homogeneous calcium-LMP-based composites. The 53-µm-CF showed the lowest hydration capability and produced the least elastic and deformable composite film due probably to CF bridged by calcium-crosslinked LMP chains. Antioxidant activity associated to the loaded CF was found in composites. When L-(+)-ascorbic acid (AA) was also loaded, its hydrolytic stability increased with the decrease in CF-particle size, showing the lowest stability in the 0%-CF- and 210 µm-CF-LMP films. Below ≈ 250 µm, the particle size determined the hydration properties of pectin-containing CF, affecting the microstructure and water mobility in composites.