In Vitro Evaluation of Pro- and Antioxidant Effects of Flavonoid Tricetin in Comparison to Myricetin

Flavonoids are rather common plant phenolic constituents that are known for potent antioxidant effects and can be beneficial for human health. Flavonoids with a pyrogallol moiety are highly efficient reducing agents with possible pro- and antioxidant effects, depending on the reaction milieu. Theref...

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Main Authors: Vladimir Chobot, Franz Hadacek, Gert Bachmann, Wolfram Weckwerth, Lenka Kubicova
Format: Article
Language:English
Published: MDPI AG 2020-12-01
Series:Molecules
Subjects:
Online Access:https://www.mdpi.com/1420-3049/25/24/5850
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spelling doaj-af18d7a887b14074840ed7be4303bba22020-12-12T00:01:19ZengMDPI AGMolecules1420-30492020-12-01255850585010.3390/molecules25245850In Vitro Evaluation of Pro- and Antioxidant Effects of Flavonoid Tricetin in Comparison to MyricetinVladimir Chobot0Franz Hadacek1Gert Bachmann2Wolfram Weckwerth3Lenka Kubicova4Division of Molecular Systems Biology, Department of Functional and Evolutionary Ecology, Faculty of Life Sciences, University of Vienna, Althanstrasse 14, A-1090 Vienna, AustriaDepartment of Plant Biochemistry, Albrecht-von-Haller Institut, Georg-August-Universität Göttingen, Justus-von-Liebig-Weg 11, D-37077 Göttingen, GermanyDivision of Molecular Systems Biology, Department of Functional and Evolutionary Ecology, Faculty of Life Sciences, University of Vienna, Althanstrasse 14, A-1090 Vienna, AustriaDivision of Molecular Systems Biology, Department of Functional and Evolutionary Ecology, Faculty of Life Sciences, University of Vienna, Althanstrasse 14, A-1090 Vienna, AustriaDivision of Molecular Systems Biology, Department of Functional and Evolutionary Ecology, Faculty of Life Sciences, University of Vienna, Althanstrasse 14, A-1090 Vienna, AustriaFlavonoids are rather common plant phenolic constituents that are known for potent antioxidant effects and can be beneficial for human health. Flavonoids with a pyrogallol moiety are highly efficient reducing agents with possible pro- and antioxidant effects, depending on the reaction milieu. Therefore, the redox properties of myricetin and tricetin were investigated by differential pulse voltammetry and deoxyribose degradation assay. Tricetin proved to be a good antioxidant but only showed negligible pro-oxidant activity in one of the deoxyribose degradation assay variants. Compared to tricetin, myricetin showed pro- and antioxidant effects. The more efficient reducing properties of myricetin are probably caused by the positive mesomeric effect of the enolic 3-hydroxy group on ring C. It is evident that the antioxidant properties of structurally similar flavonoids can be converted to apparent pro-oxidant effects by relatively small structural changes, such as hydroxylation. Since reactive oxygen species (ROS) often serve as secondary messengers in pathological and physiological processes in animal and plant cells, the pro- and antioxidant properties of flavonoids are an important part of controlling mechanisms of tissue signal cascades.https://www.mdpi.com/1420-3049/25/24/5850agingelectroanalytical methodsFenton reactionfree radicalshomeostasisiron
collection DOAJ
language English
format Article
sources DOAJ
author Vladimir Chobot
Franz Hadacek
Gert Bachmann
Wolfram Weckwerth
Lenka Kubicova
spellingShingle Vladimir Chobot
Franz Hadacek
Gert Bachmann
Wolfram Weckwerth
Lenka Kubicova
In Vitro Evaluation of Pro- and Antioxidant Effects of Flavonoid Tricetin in Comparison to Myricetin
Molecules
aging
electroanalytical methods
Fenton reaction
free radicals
homeostasis
iron
author_facet Vladimir Chobot
Franz Hadacek
Gert Bachmann
Wolfram Weckwerth
Lenka Kubicova
author_sort Vladimir Chobot
title In Vitro Evaluation of Pro- and Antioxidant Effects of Flavonoid Tricetin in Comparison to Myricetin
title_short In Vitro Evaluation of Pro- and Antioxidant Effects of Flavonoid Tricetin in Comparison to Myricetin
title_full In Vitro Evaluation of Pro- and Antioxidant Effects of Flavonoid Tricetin in Comparison to Myricetin
title_fullStr In Vitro Evaluation of Pro- and Antioxidant Effects of Flavonoid Tricetin in Comparison to Myricetin
title_full_unstemmed In Vitro Evaluation of Pro- and Antioxidant Effects of Flavonoid Tricetin in Comparison to Myricetin
title_sort in vitro evaluation of pro- and antioxidant effects of flavonoid tricetin in comparison to myricetin
publisher MDPI AG
series Molecules
issn 1420-3049
publishDate 2020-12-01
description Flavonoids are rather common plant phenolic constituents that are known for potent antioxidant effects and can be beneficial for human health. Flavonoids with a pyrogallol moiety are highly efficient reducing agents with possible pro- and antioxidant effects, depending on the reaction milieu. Therefore, the redox properties of myricetin and tricetin were investigated by differential pulse voltammetry and deoxyribose degradation assay. Tricetin proved to be a good antioxidant but only showed negligible pro-oxidant activity in one of the deoxyribose degradation assay variants. Compared to tricetin, myricetin showed pro- and antioxidant effects. The more efficient reducing properties of myricetin are probably caused by the positive mesomeric effect of the enolic 3-hydroxy group on ring C. It is evident that the antioxidant properties of structurally similar flavonoids can be converted to apparent pro-oxidant effects by relatively small structural changes, such as hydroxylation. Since reactive oxygen species (ROS) often serve as secondary messengers in pathological and physiological processes in animal and plant cells, the pro- and antioxidant properties of flavonoids are an important part of controlling mechanisms of tissue signal cascades.
topic aging
electroanalytical methods
Fenton reaction
free radicals
homeostasis
iron
url https://www.mdpi.com/1420-3049/25/24/5850
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