Dehydrogenation of Betacyanins in Heated Betalain-Rich Extracts of Red Beet (<i>Beta vulgaris</i> L.)
Betacyanins are a group of water-soluble red-violet compounds containing nitrogen in their structure. These are biosynthesized in red beetroot (<i>Beta vulgaris</i> L.), a widely consumed vegetable that contains significant amounts of nutritious and bioactive compounds which are also fou...
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| Format: | Article |
| Language: | English |
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MDPI AG
2022-01-01
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| Series: | International Journal of Molecular Sciences |
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| Online Access: | https://www.mdpi.com/1422-0067/23/3/1245 |
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| author | Katarzyna Sutor-Świeży Michał Antonik Justyna Proszek Boris Nemzer Zbigniew Pietrzkowski Łukasz Popenda Tomasz Świergosz Sławomir Wybraniec |
| author_facet | Katarzyna Sutor-Świeży Michał Antonik Justyna Proszek Boris Nemzer Zbigniew Pietrzkowski Łukasz Popenda Tomasz Świergosz Sławomir Wybraniec |
| author_sort | Katarzyna Sutor-Świeży |
| collection | DOAJ |
| description | Betacyanins are a group of water-soluble red-violet compounds containing nitrogen in their structure. These are biosynthesized in red beetroot (<i>Beta vulgaris</i> L.), a widely consumed vegetable that contains significant amounts of nutritious and bioactive compounds which are also found in dietary supplements. This contribution presents results of betacyanin thermal oxidation (resulting in dehydrogenation) interrelated with decarboxylation in selected acetate/phosphate buffers at pH 3–8 and at 85 °C, which may be of particular significance for formulation and performance of foods. Most of the reaction products were detected at the highest concentrations in the acidic solutions (pH 3–4). The main dehydrogenation reaction pathways were monitored by LC-DAD-MS/MS and were associated with decarboxylation of the principal extract pigments, betanin/isobetanin and neobetanin, at carbon positions C-2 and C-17. Additional reactions are accompanied by the 2,15-decarboxylation processes at different dehydrogenation levels with 15-decarboxy-betanin and 2,15-bidecarboxy-betanin, structurally elucidated by NMR analysis, as the distinct indicators of this route type. For other novel pigments detected, 2,15-bidecarboxy-xanbetanin, 2,15-bidecarboxy-xanneobetanin and 2,15,17-tridecarboxy-neobetanin, additional high resolution mass spectrometric analyses were performed and confirmed their molecular formulas. |
| first_indexed | 2024-03-09T23:49:37Z |
| format | Article |
| id | doaj.art-4b975bd6eab04957bde881d047f21580 |
| institution | Directory Open Access Journal |
| issn | 1661-6596 1422-0067 |
| language | English |
| last_indexed | 2024-03-09T23:49:37Z |
| publishDate | 2022-01-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | International Journal of Molecular Sciences |
| spelling | doaj.art-4b975bd6eab04957bde881d047f215802023-11-23T16:37:19ZengMDPI AGInternational Journal of Molecular Sciences1661-65961422-00672022-01-01233124510.3390/ijms23031245Dehydrogenation of Betacyanins in Heated Betalain-Rich Extracts of Red Beet (<i>Beta vulgaris</i> L.)Katarzyna Sutor-Świeży0Michał Antonik1Justyna Proszek2Boris Nemzer3Zbigniew Pietrzkowski4Łukasz Popenda5Tomasz Świergosz6Sławomir Wybraniec7Department C-1, Faculty of Chemical Engineering and Technology, Cracow University of Technology, ul. Warszawska 24, 31-155 Cracow, PolandDepartment C-1, Faculty of Chemical Engineering and Technology, Cracow University of Technology, ul. Warszawska 24, 31-155 Cracow, PolandDepartment C-1, Faculty of Chemical Engineering and Technology, Cracow University of Technology, ul. Warszawska 24, 31-155 Cracow, PolandResearch and Analytical Center, VDF FutureCeuticals, Inc., 2692 N. State Rt. 1-17, Momence, IL 60954, USADiscovery Research Lab, VDF FutureCeuticals, Inc., 23 Peters Canyon Rd., Irvine, CA 92606, USANanoBioMedical Centre, Adam Mickiewicz University Poznan, ul. Wszechnicy Piastowskiej 3, 61-614 Poznan, PolandDepartment C-1, Faculty of Chemical Engineering and Technology, Cracow University of Technology, ul. Warszawska 24, 31-155 Cracow, PolandDepartment C-1, Faculty of Chemical Engineering and Technology, Cracow University of Technology, ul. Warszawska 24, 31-155 Cracow, PolandBetacyanins are a group of water-soluble red-violet compounds containing nitrogen in their structure. These are biosynthesized in red beetroot (<i>Beta vulgaris</i> L.), a widely consumed vegetable that contains significant amounts of nutritious and bioactive compounds which are also found in dietary supplements. This contribution presents results of betacyanin thermal oxidation (resulting in dehydrogenation) interrelated with decarboxylation in selected acetate/phosphate buffers at pH 3–8 and at 85 °C, which may be of particular significance for formulation and performance of foods. Most of the reaction products were detected at the highest concentrations in the acidic solutions (pH 3–4). The main dehydrogenation reaction pathways were monitored by LC-DAD-MS/MS and were associated with decarboxylation of the principal extract pigments, betanin/isobetanin and neobetanin, at carbon positions C-2 and C-17. Additional reactions are accompanied by the 2,15-decarboxylation processes at different dehydrogenation levels with 15-decarboxy-betanin and 2,15-bidecarboxy-betanin, structurally elucidated by NMR analysis, as the distinct indicators of this route type. For other novel pigments detected, 2,15-bidecarboxy-xanbetanin, 2,15-bidecarboxy-xanneobetanin and 2,15,17-tridecarboxy-neobetanin, additional high resolution mass spectrometric analyses were performed and confirmed their molecular formulas.https://www.mdpi.com/1422-0067/23/3/1245dehydrogenationdecarboxylationxanbetaninneobetaninred beet rootcolorants |
| spellingShingle | Katarzyna Sutor-Świeży Michał Antonik Justyna Proszek Boris Nemzer Zbigniew Pietrzkowski Łukasz Popenda Tomasz Świergosz Sławomir Wybraniec Dehydrogenation of Betacyanins in Heated Betalain-Rich Extracts of Red Beet (<i>Beta vulgaris</i> L.) International Journal of Molecular Sciences dehydrogenation decarboxylation xanbetanin neobetanin red beet root colorants |
| title | Dehydrogenation of Betacyanins in Heated Betalain-Rich Extracts of Red Beet (<i>Beta vulgaris</i> L.) |
| title_full | Dehydrogenation of Betacyanins in Heated Betalain-Rich Extracts of Red Beet (<i>Beta vulgaris</i> L.) |
| title_fullStr | Dehydrogenation of Betacyanins in Heated Betalain-Rich Extracts of Red Beet (<i>Beta vulgaris</i> L.) |
| title_full_unstemmed | Dehydrogenation of Betacyanins in Heated Betalain-Rich Extracts of Red Beet (<i>Beta vulgaris</i> L.) |
| title_short | Dehydrogenation of Betacyanins in Heated Betalain-Rich Extracts of Red Beet (<i>Beta vulgaris</i> L.) |
| title_sort | dehydrogenation of betacyanins in heated betalain rich extracts of red beet i beta vulgaris i l |
| topic | dehydrogenation decarboxylation xanbetanin neobetanin red beet root colorants |
| url | https://www.mdpi.com/1422-0067/23/3/1245 |
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