Rutin (quercetin-3-O-rutinoside) is one of the most abundant bioflavonoids with various biological and pharmacological activities. Considering the ubiquitous presence of Mg(II) and Ca(II) ions in biological systems we decided to investigate their influence on the autoxidation of rutin in weakly alkaline aqueous solutions. Changes in UV-Vis spectra recorded during the rutin autoxidation in aqueous solution at pH 8.4 revealed that this process was very slow in the absence of metal ions. The presence of Mg(II) and, especially Ca(II) ion, increased the transformation rate of rutin. UV-Vis spectra recorded after prolonged autoxidation indicated the formation of humic acidlike products in the presence of Mg(II) and Ca(II) ions. Four new compounds formed during the initial stage of rutin autoxidation in the presence of Mg(II) and Ca(II) ions were detected by HPLCDAD. Based on the analysis of their DAD UV-Vis spectra and comparison of their retention times with the retention time value for rutin, we concluded that the initial rutin transformation products were formed by the water addition on double bond in ring C and hydroxylation of ring B. A very small decrease of the initial rutin concentration (4%) was observed by HPLC-DAD in the absence of metal ions for the period of 90 minutes. However, rutin concentration decrease was much larger in the presence of Mg(II) and Ca(II) ions (14% and 24%, respectively). The more pronounced effect of Ca(II) ion on the rutin autoxidation may be explained by the stronger binding of Mg(II) ion to rutin and thus greater stabilizing effect on reaction intermediates caused by its higher ionic potential (charge/ionic radius ratio) in comparison to Ca(II) ion. The results of this study may contribute to the better understanding of interactions of Mg(II) and Ca(II) ions with natural phenolic antioxidants which are important for their various biological activities.
This work is licensed under a Creative Commons Attribution 4.0 International License (CC BY 4.0).
11
Xue Du, Angela D. Myracle
(2018)
Fermentation alters the bioaccessible phenolic compounds and increases the alpha-glucosidase inhibitory effects of aronia juice in a dairy matrix followingin vitrodigestion
Food & Function, 9(5)
10.1039/C8FO00250A
Goran M. Nikolić, Slavoljub C. Živanović, Milica G. Nikolić, Aleksandar M. Veselinović
(2023)
Kinetics and mechanism of caffeic acid autoxidation in weakly alkaline aqueous solutions in the presence of Mg(II) ions
Reaction Kinetics, Mechanisms and Catalysis, 136(3)
10.1007/s11144-023-02358-3
Slavoljub C. Živanović, Aleksandar M. Veselinović, Žarko J. Mitić, Goran M. Nikolić
(2018)
The study of the influence of Mg(ii) and Ca(ii) ions on caffeic acid autoxidation in weakly alkaline aqueous solution using MCR-ALS analysis of spectrophotometric data
New Journal of Chemistry, 42(8)
10.1039/C8NJ00871J
Milica G. Nikolić, Nenad S. Krstić, Slavoljub C. Živanović, Goran M. Nikolić
(2022)
The influence of Mg(II) and Ca(II) ions on the autoxidation of 4-methylcatechol in weakly alkaline aqueous solutions
Reaction Kinetics, Mechanisms and Catalysis, 135(3)
10.1007/s11144-022-02180-3
Marcin Masłowski, Justyna Miedzianowska, Agnieszka Czylkowska, Magdalena Efenberger-Szmechtyk, Agnieszka Nowak, Krzysztof Strzelec
(2020)
Anti-Oxidative Activity of Alcohol-Water Extracts from Field Horsetail (Equisteum arvense) in Elastomer Vulcanizates Subjected to Accelerated Aging Processes
Materials, 13(21)
10.3390/ma13214903
Efrat Hochma, Paul Ben Ishai, Michael A. Firer, Refael Minnes
(2024)
Phyto-Photodynamic Therapy of Prostate Cancer Cells Mediated by Yemenite ‘Etrog’ Leave Extracts
Nutrients, 16(12)
10.3390/nu16121820
Efrat Hochma, Michael A. Firer, Refael Minnes
(2025)
Near-Infrared and Sono-Enhanced Photodynamic Therapy of Prostate Cancer Cells Using Phyto-Second Harmonic Generation Nanoconjugates
Polymers, 17(13)
10.3390/polym17131831
Milica G. Nikolić, Nataša V. Radosavljević-Stevanović, Žarko J. Mitić, Slavoljub C. Živanović, Goran M. Nikolić
(2025)
Autoxidation of gallic acid as a viable alternative to enzymatic polymerization: spectroscopic characterization of autoxidation products
New Journal of Chemistry, 49(41)
10.1039/D5NJ02152A
Maribel Valenzuela-González, José Luis Cárdenas-López, Armando Burgos-Hernández, Manuel Viuda-Martos, Norma Julieta Salazar-López, Alan Ruiz-Hernández, J. Abraham Domínguez-Avila, Maribel Robles-Sánchez, Poulami Jha
(2025)
Biological, Quality, and Sensory Evaluation of Raw and Microwaved Quinoa Baked Tortilla Chips
Journal of Food Processing and Preservation, 2025(1)
10.1155/jfpp/2054874
María José Frutos, Laura Rincón-Frutos, Estefanía Valero-Cases
(2019)
Nonvitamin and Nonmineral Nutritional Supplements
, ()
10.1016/B978-0-12-812491-8.00015-1The statements, opinions and data contained in the journal are solely those of the individual authors and contributors and not of the publisher and the editor(s). We stay neutral with regard to jurisdictional claims in published maps and institutional affiliations.