Antioxidant properties of ferrous flavanol mixtures

Grzesik, Michalina; Bartosz, Grzegorz; Dziedzic, Andrzej; Naróg, Dorota; Namieśnik, Jacek; Sadowska-Bartosz, Izabela

doi:10.1016/j.foodchem.2018.06.076

Cited by 19 publications

(10 citation statements)

References 42 publications

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“…These characteristics confer to the rutin molecule a high ability to act as a ligand in coordination compounds, with two chelating sites, named site I (C4O and C5O) and site II (C4′O and C5′O or catechol moiety). It can be found in the literature, synthesis and characterization of rutin complexes with Zn II , Cu II , Fe II , Sn II , Al III[17] and other metal ions, revealing coordination compounds with various ligand–metal stoichiometries (1:1, 1:2, 2:1) and spatial conformations. According to Ikeda et al., the formation of coordination compounds with rutin greatly increases the antioxidant power and consequently other properties (especially antitumor activity), with the rutin‐zinc(II) complexes showing significant higher antioxidant activity, and no toxicity against normal cells of rat organ and potential cytotoxicity against the cancer cells.…”

Section: Introductionmentioning

confidence: 99%

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Structural Determination of Antioxidant and Anticancer Flavonoid Rutin in Solution through DFT Calculations of ¹H NMR Chemical Shifts

Souza

Silva

2018

ChemistryOpen

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As the knowledge of the predominant molecular structure of antioxidant and anticancer flavonoid rutin in solution is very important for understanding the mechanism of action, a quantum chemical investigation of plausible rutin structures including solvent effects is of relevance. In this work, DFT calculations were performed to find possible minimum energy structures for the rutin molecule. 1H NMR chemical shift DFT calculations were carried out in DMSO solution using the polarizable continuum model (PCM) to simulate the solvent effect. Analysis of the experimental and theoretical 1H NMR chemical shift profiles offers a powerful fingerprint criterion to determine the predominant molecular structure in solution. Therefore, our aim is to find the best match between experimental (in DMSO‐d) and theoretical (PCM–DMSO) 1H NMR spectrum profiles. Among 34 optimized structures located on the potential energy surface, we found that structure 32, with a B‐ring deviated 30° from a planar configuration (geometry usually assumed for polyphenols), showed an almost perfect agreement with experimental the 1H NMR pattern when compared to the corresponding fully optimized planar geometry. This structure is also predicted as the global minimum based on room‐temperature Gibbs free energy calculations in solution and, therefore, should be experimentally observed. This is new and valuable structural information regarding structure–activity relationship studies, and such information is hard to obtain by experimentalists without the aid of the X‐ray diffraction technique.

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Section: Introductionmentioning

confidence: 99%

“…Crystallographic analysis by X‐ray diffraction is an important tool for obtaining structural data of solid phase flavonoids . Another useful technique in the structural description of organic molecules is nuclear magnetic resonance spectroscopy (NMR).…”

Section: Introductionmentioning

confidence: 99%

Structural Determination of Antioxidant and Anticancer Flavonoid Rutin in Solution through DFT Calculations of ¹H NMR Chemical Shifts

Souza

Silva

2018

ChemistryOpen

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“…The simplest explanation is that the protection is due to the direct antioxidant action of the flavanols which are excellent antioxidants (Grzesik et al . ,). However, it has been also reported that EGC‐G and other tea polyphenols activate the Yap1 transcription factor mounting elevated expression of endogenous antioxidant proteins (Maeta et al .…”

Section: Discussionmentioning

confidence: 99%

“…They have strong antioxidant properties, mainly due to reactions with reactive oxygen, nitrogen and halogen species and to binding transition metal ions (Rice‐Evans ; Grzesik et al . ,). However, in the body they exert a plethora of other effects which can be only partly or not at all related to their antioxidant action.…”

Section: Introductionmentioning

confidence: 99%

Flavanols protect the yeastSaccharomyces cerevisiaeagainst heating and freezing/thawing injury

Naparło

Żyracka

Bartosz

et al. 2019

Journal of Applied Microbiology

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Aims The aim of the study was to check whether two flavanols ((−)‐epigallocatechin gallate and (+)‐catechin) can ameliorate oxidative stress (OS) accompanying and contributing to the lethal effects of heating (50°C) and freezing‐thawing on the yeast Saccharomyces cerevisiae. Methods and Results The flavanols studied increased yeast survival during heating and freezing‐thawing, estimated by the colony forming assay. They improved also such indices of OS as increased production of reactive oxygen species, decrease of total antioxidant activity of yeast cell extracts and increase in the level of protein carbonyls. Conclusions Amelioration of OS by flavanols increases the survival of the yeast subjected to high temperature and freezing‐thawing. Significance and Impact of the Study Flavanols may be considered as means of enhancing yeast survival under extreme temperature conditions and probably in other conditions involving OS.

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“…Flavanols also possess antioxidant effects, antidepressant properties, and an impact on body weight loss, thereby reducing the effect on obesity [35][36][37]. Flavanols rich food intake can reverse vascular dysfunction in diabetics.…”

Section: Flavan-3-ols (Flavanols)mentioning

confidence: 99%

Flavonoids as Antidiabetic Agents

Cahyana

Adiyanti

2021

Indones. J. Chem.

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Flavonoids are polyphenol compounds that exert many potential health benefits, including diabetes type-II, which is the third most common disease that causes death, right after cancer and cardiovascular diseases. The excessively high level of blood glucose has been believed to trigger type II diabetes. The aim of this review is to describe the flavonoid's ability as an alternative treatment for diabetes type-II patients. This paper addresses several aspects in which flavonoids may impart a pivotal role in starch digestion, such as the interaction of flavonoids with enzymes involved in starch hydrolysis, the role of flavonoids in inhibiting glucose absorption, as well as the interaction of flavonoids with starch to form a complex resistant to hydrolysis. Further studies, however, are suggested to extensively carry out, particularly the ones dealing with the intervention study using human volunteers to reveal the role of flavonoids in the real applications. The data on human intervention studies are still rare and can further be exploited using meta-analysis to have firmer results. Flavonoids in the food matrix are more realistic to perform to reveal the effect of interaction with other compounds, which may affect the mechanism of flavonoids interaction or their bioavailability.

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Antioxidant properties of ferrous flavanol mixtures

Cited by 19 publications

References 42 publications

Structural Determination of Antioxidant and Anticancer Flavonoid Rutin in Solution through DFT Calculations of ¹H NMR Chemical Shifts

Structural Determination of Antioxidant and Anticancer Flavonoid Rutin in Solution through DFT Calculations of ¹H NMR Chemical Shifts

Flavanols protect the yeastSaccharomyces cerevisiaeagainst heating and freezing/thawing injury

Flavonoids as Antidiabetic Agents

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Antioxidant properties of ferrous flavanol mixtures

Cited by 19 publications

References 42 publications

Structural Determination of Antioxidant and Anticancer Flavonoid Rutin in Solution through DFT Calculations of 1H NMR Chemical Shifts

Structural Determination of Antioxidant and Anticancer Flavonoid Rutin in Solution through DFT Calculations of 1H NMR Chemical Shifts

Flavanols protect the yeastSaccharomyces cerevisiaeagainst heating and freezing/thawing injury

Flavonoids as Antidiabetic Agents

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About

Structural Determination of Antioxidant and Anticancer Flavonoid Rutin in Solution through DFT Calculations of ¹H NMR Chemical Shifts

Structural Determination of Antioxidant and Anticancer Flavonoid Rutin in Solution through DFT Calculations of ¹H NMR Chemical Shifts