Effects of metal cations on betanin stability in aqueous-organic solutions

Wybraniec, Sławomir; Starzak, Karolina; Skopińska, A.; Szaleniec, Maciej; Słupski, Jacek; Mitka, Katarzyna; Kowalski, Piotr; Michałowski, Tadeusz

doi:10.1007/s10068-013-0088-7

Cited by 31 publications

(26 citation statements)

References 16 publications

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“…Anyway, the oxidation number, representing the degree of oxidation of an element in a compound or a species, is commonly perceived as a contractual concept. In this regard, formulation of GEB according to approach II is more useful than the approach I when applied to complex organic species in redox systems of biological origin [63][64][65][66][67]. The approach II to GEB is advantageous/desired, inter alia, for redox systems where radical and ion-radical species are formed.…”

Section: Discussionmentioning

confidence: 99%

Generalized Electron Balance (GEB) as the Law of Nature in Electrolytic Redox Systems

Michałowska-Kaczmarczyk¹,

Spórna‐Kucab²,

Michałowski³

2017

Redox - Principles and Advanced Applications

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This chapter refers to fundamental/general/obligatory regularities of electrolytic systems. The linear combination 2•f(O)-f(H) of elemental balances, f(H) for H and f(O) for O, provides a rigorous criterion distinguishing between redox and non-redox systems is presented as the general relation distinguishing between electrolytic redox and non-redox systems in aqueous media. As the linearly independent equation for a redox system, 2•f(O) À f(H) is considered as the primary form of the generalized electron balance (GEB), perceived as a law of nature, as the hidden connection of physicochemical laws and the breakthrough in thermodynamic theory of electrolytic redox systems. GEB completes the set of 2+K equations necessary for thermodynamic resolution of redox systems according to generalized approach to electrolytic systems (GATES) applying all relevant, physicochemical knowledge available. GATES/GEB, perceived as an example of excellent paradigm, provides the best thermodynamic approach to electrolytic redox systems of any degree of complexity, in aqueous, non-aqueous, and mixed-solvent media. The formulation of GEB does not need prior knowledge of oxidation numbers for all elements in components forming any electrolytic system, within GATES/GEB, the stoichiometry, oxidation number, oxidant, reductant and equivalent mass are as derivative concepts.

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Section: Discussionmentioning

confidence: 99%

Generalized Electron Balance (GEB) as the Law of Nature in Electrolytic Redox Systems

Michałowska-Kaczmarczyk¹,

Spórna‐Kucab²,

Michałowski³

2017

Redox - Principles and Advanced Applications

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“…The optimum pH for betanin ranges from 4.0 to 6.0, and, when outside this range, oxidation causes marked changes in color, such as pigment or food product darkening (Elbe, Maing, and Amundson 1974). The presence of metals like Cu (II) and Fe (III) also decreases betanin stability (Attoe and von Elbe 1984;Czapski 1990;Wybraniec et al 2013).…”

Section: Betanin Biosynthesis Plasticity and Bioaccessibilitymentioning

confidence: 99%

Betanin as a multipath oxidative stress and inflammation modulator: a beetroot pigment with protective effects on cardiovascular disease pathogenesis

Silva

Baião

Ferreira

et al. 2020

Critical Reviews in Food Science and Nutrition

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Oxidative stress is a common physiopathological condition enrolled in risk factors for cardiovascular diseases. Individuals in such a redox imbalance status present endothelial dysfunctions and inflammation, reaching the onset of heart disease. Phytochemicals are able to attenuate the main mechanisms of oxidative stress and inflammation and should be considered as supportive therapies to manage risk factors for cardiovascular diseases. Beetroot (Beta vulgaris L.) is a rich source of bioactive compounds, including betanin (betanidin-5-O-b-glucoside), a pigment displaying the potential to alleviate oxidative stress and inflammantion, as previously demonstrated in preclinical trials. Betanin resists gastrointestinal digestion, is absorbed by the epithelial cells of intestinal mucosa and reaches the plasma in its active form. Betanin displays free-radical scavenger ability through hydrogen or electron donation, preserving lipid structures and LDL particles while inducing the transcription of antioxidant genes through the nuclear factor erythroid-2-related factor 2 and, simultaneously, suppressing the pro-inflammatory nuclear factor kappa-B pathways. This review discusses the anti-radical and gene regulatory cardioprotective activities of betanin in the pathophysiology of endothelial damage and atherogenesis, the main conditions for cardiovascular disease. In addition, betanin influences on these multipath cellular signals and aiding in reducing cardiovascular disorders is proposed.

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“…16,17 This is based on previous knowledge that metal cations such as copper, iron, tin, and aluminum were reported to accelerate betanin degradation even at trace concentrations. 18 This accelerated degradation should also be considered when studying the fate of these pigments within human body tissues. Unwanted degradation of betalains may also be catalyzed by release of trace amounts of metals in materials used in food packaging and in food ingredients.…”

Section: ■ Introductionmentioning

confidence: 99%

Alternative Mechanisms of Betacyanin Oxidation by Complexation and Radical Generation

Kumorkiewicz

Szmyr

Popenda

et al. 2019

J. Agric. Food Chem.

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The use of natural pigments such as betalains in food and health-related products is often limited by said pigments’ relative oxidative stabilities in the products or physiological matrices. Determination of the mechanism of oxidation may inform future development and delivery of better stabilized molecules for improved outcomes. In order to best determine the oxidation mechanism of betanin, a natural food colorant, our efforts were directed toward structural elucidation (LCMS-IT-TOF and NMR) of previously tentatively identified key dehydrogenation products that had been generated as a result of betanin, decarboxylated betanin, and neobetanin oxidation by 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) cation radicals. The resultant oxidation products, the neo-derivatives, were the most stable and survived the preparative isolation and purification process. Structural analyses subsequently confirmed that these compounds, as well as neobetanin, were also the key products of alternative pathways of betanin and 2-decarboxy-betanin oxidation when catalyzed by Cu2+ cations in aqueous solutions at pH close to neutral. Therefore, the structures of the following five neo- or xanneo-derivatives (14,15- or 2,3,14,15-dehydrogenated derivatives, respectively) were confirmed: neobetanin, 2-decarboxy-neobetanin, 2-decarboxy-xanneobetanin, 2,17-bidecarboxy-xanneobetanin, and 2,15,17-tridecarboxy-xanneobetanin. This research confirmed that Cu2+-catalyzed oxidation of betanin and 2-decarboxy-betanin results in generation of neo-derivatives of betanin. In contrast, Cu2+-catalyzed oxidation of 17-decarboxy-betanin and 2,17-bidecarboxy-betanin resulted mostly in formation of betanin xan-derivatives. A relevant mechanism of Cu2+-catalyzed oxidation of the pigments is proposed herein that suggests that the oxidation of betanin can possibly occur in the region of the dihydropyridinic ring and can omit the stage of methide quinone formation in the dihydroindolic system.

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Effects of metal cations on betanin stability in aqueous-organic solutions

Cited by 31 publications

References 16 publications

Generalized Electron Balance (GEB) as the Law of Nature in Electrolytic Redox Systems

Generalized Electron Balance (GEB) as the Law of Nature in Electrolytic Redox Systems

Betanin as a multipath oxidative stress and inflammation modulator: a beetroot pigment with protective effects on cardiovascular disease pathogenesis

Alternative Mechanisms of Betacyanin Oxidation by Complexation and Radical Generation

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