Abstract
Structure-related biological activities of flavanones are still considered largely unexplored. Since they exhibit various medicinal activities, it is intriguing to enter deeper into their chemical structures, electronic transitions or interactions with some biomolecules in order to find properties that allow us to better understand their effects. Little information is available on biological activity of flavanone and its monohydroxy derivatives in relation to their physicochemical properties as spectral profiles, existence of protonated/deprotonated species under pH changes or interaction with Calf Thymus DNA. We devoted this work to research demonstrating differences in the physicochemical properties of the four flavanones: flavanone, 2′-hydroxyflavanone, 6-hydroxyflavanone and 7-hydroxyflavanone and linking them to their biological activity. Potentiometric titration, UV–Vis spectroscopy were used to investigate influence of pH on acid–base and spectral profiles and to propose the mode of interaction with DNA. Cyclic voltammetry was applied to evaluate antioxidant potentiality and additionally, theoretical DFT(B3LYP) method to disclose electronic structure and properties of the compounds. Molecular geometries, proton affinities and pKa values have been determined. According to computational and cyclic voltammetry results we could predict higher antioxidant activity of 6-hydroxyflavanone with respect to other compounds. The values of Kb intrinsic binding constants of the flavanones indicated weak interactions with DNA. Structure–activity relationships observed for antioxidant activity and DNA interactions suggest that 6-hydroxyflavanone can protect DNA against oxidative damage most effectively than flavanone, 2′-hydroxyflavanone or 7-hydroxyflavanone.
Highlights
Flavonoids belong to a large group of polyphenolic compounds with the structure of benzo-γ-piron and are commonly found in plants
Gibbs energies of the neutral G∗ (HF(s) and anionic G∗ A−(s) forms of the studied flavanones at standard conditions were calculated as the sum of the density functional theory (DFT)(B3LYP)/6-31+G(d,p) calculated thermal correction to free Gibbs energy and the DFT(B3LYP)/6-31+G(d,p)/PCM single point electronic energy, to the method previously proposed by Wright et al [73] and Bryantsev et al [74]
The results of our research have shed some light on clarification of different biological activity of the flavanones studied
Summary
Flavonoids belong to a large group of polyphenolic compounds with the structure of benzo-γ-piron and are commonly found in plants. Molecules 2019, 24, 3049 pointed out that the excess use of these compounds could have drastic effects, as high concentrations of flavonoids may act as mutagens, pro-oxidants and inhibitors of hormone metabolizing enzymes Their chemical nature depends on their structural class, degree of hydroxylation and polymerization or other substitutions and conjugations. Since they exhibit various medicinal activities, it is intriguing to enter deeper into their chemical structures, electronic transitions or interactions with some biomolecules in order to find properties that allow us to better understand their effects Such a knowledge will create the possibility of more conscious and purposeful use of these compounds both in medicine and in dietary supplements. To the best of our knowledge only few previously published studies have been devoted to Wróblewski [15] have applied both experimental (absorption fluorescence spectroscopy) the structureand andet.properties of the studied hydroxyflavanones andand their corresponding chalcones. Nature of the electronic transitions which contribute to the absorption spectra of F, 2 HF, 6HF and 7HF
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