Interference of malvidin and its mono- and di-glucosides on the membrane — Combined in vitro and computational chemistry study
The antioxidative and antiradical properties of malvidin (Mv), malvidin 3-O-glucoside (Mv 3-glc) and malvidin 3,5-O-diglucoside (Mv 3,5-diglc) were evaluated by AAPH● and DPPH● assays, respectively. In both cases, a decrease in activity was observed in the following order Mv > Mv 3-glc > Mv 3,...
| Main Authors: | , , , |
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| Format: | Article |
| Language: | English |
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Elsevier
2022-12-01
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| Series: | Journal of Functional Foods |
| Subjects: | |
| Online Access: | http://www.sciencedirect.com/science/article/pii/S1756464622004108 |
| _version_ | 1811187615812026368 |
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| author | Paulina Strugała-Danak Maciej Spiegel Kacper Hurynowicz Janina Gabrielska |
| author_facet | Paulina Strugała-Danak Maciej Spiegel Kacper Hurynowicz Janina Gabrielska |
| author_sort | Paulina Strugała-Danak |
| collection | DOAJ |
| description | The antioxidative and antiradical properties of malvidin (Mv), malvidin 3-O-glucoside (Mv 3-glc) and malvidin 3,5-O-diglucoside (Mv 3,5-diglc) were evaluated by AAPH● and DPPH● assays, respectively. In both cases, a decrease in activity was observed in the following order Mv > Mv 3-glc > Mv 3,5-diglc. Quantum mechanics studies have confirmed this pattern, which can be explained by an underlying activity based on hydrogen atom transfer from C3-hydroxyl. Further measurements of the ability of malvidins to interact with membrane-mimicking liposomes revealed that malvidins, depending on their structure, increase packing order mainly in the hydrophilic region of the membrane bilayer. A mixed molecular dynamics and quantum mechanics protocol explained this in terms of fluctuating charge distribution among the species investigated. These findings are key in explaining elucidating the antioxidant activity of malvidins against membranes as a result of surface rearrangement and may have important implications for future pharmacological applications. |
| first_indexed | 2024-04-11T14:06:25Z |
| format | Article |
| id | doaj.art-e644f0848f094ba6a9751cc619acc7ea |
| institution | Directory Open Access Journal |
| issn | 1756-4646 |
| language | English |
| last_indexed | 2024-04-11T14:06:25Z |
| publishDate | 2022-12-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Journal of Functional Foods |
| spelling | doaj.art-e644f0848f094ba6a9751cc619acc7ea2022-12-22T04:19:53ZengElsevierJournal of Functional Foods1756-46462022-12-0199105340Interference of malvidin and its mono- and di-glucosides on the membrane — Combined in vitro and computational chemistry studyPaulina Strugała-Danak0Maciej Spiegel1Kacper Hurynowicz2Janina Gabrielska3Department of Physics and Biophysics, Wrocław University of Environmental and Life Sciences, C. K. Norwida 25, 50-375 Wrocław, Poland; Corresponding author at: Department of Physics and Biophysics, Wrocław University of Environmental and Life Sciences, C. K. Norwida 25, 50-375 Wrocław, Poland.Department of Pharmacognosy and Herbal Medicines, Wrocław Medical University, Borowska 211A, 50-556 Wrocław, PolandDepartment of Physics and Biophysics, Wrocław University of Environmental and Life Sciences, C. K. Norwida 25, 50-375 Wrocław, PolandDepartment of Physics and Biophysics, Wrocław University of Environmental and Life Sciences, C. K. Norwida 25, 50-375 Wrocław, PolandThe antioxidative and antiradical properties of malvidin (Mv), malvidin 3-O-glucoside (Mv 3-glc) and malvidin 3,5-O-diglucoside (Mv 3,5-diglc) were evaluated by AAPH● and DPPH● assays, respectively. In both cases, a decrease in activity was observed in the following order Mv > Mv 3-glc > Mv 3,5-diglc. Quantum mechanics studies have confirmed this pattern, which can be explained by an underlying activity based on hydrogen atom transfer from C3-hydroxyl. Further measurements of the ability of malvidins to interact with membrane-mimicking liposomes revealed that malvidins, depending on their structure, increase packing order mainly in the hydrophilic region of the membrane bilayer. A mixed molecular dynamics and quantum mechanics protocol explained this in terms of fluctuating charge distribution among the species investigated. These findings are key in explaining elucidating the antioxidant activity of malvidins against membranes as a result of surface rearrangement and may have important implications for future pharmacological applications.http://www.sciencedirect.com/science/article/pii/S1756464622004108AnthocyaninsMalvidinsLipid membraneTheoretical studiesStructure-dependent relationships |
| spellingShingle | Paulina Strugała-Danak Maciej Spiegel Kacper Hurynowicz Janina Gabrielska Interference of malvidin and its mono- and di-glucosides on the membrane — Combined in vitro and computational chemistry study Journal of Functional Foods Anthocyanins Malvidins Lipid membrane Theoretical studies Structure-dependent relationships |
| title | Interference of malvidin and its mono- and di-glucosides on the membrane — Combined in vitro and computational chemistry study |
| title_full | Interference of malvidin and its mono- and di-glucosides on the membrane — Combined in vitro and computational chemistry study |
| title_fullStr | Interference of malvidin and its mono- and di-glucosides on the membrane — Combined in vitro and computational chemistry study |
| title_full_unstemmed | Interference of malvidin and its mono- and di-glucosides on the membrane — Combined in vitro and computational chemistry study |
| title_short | Interference of malvidin and its mono- and di-glucosides on the membrane — Combined in vitro and computational chemistry study |
| title_sort | interference of malvidin and its mono and di glucosides on the membrane combined in vitro and computational chemistry study |
| topic | Anthocyanins Malvidins Lipid membrane Theoretical studies Structure-dependent relationships |
| url | http://www.sciencedirect.com/science/article/pii/S1756464622004108 |
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