Chemical Hemisynthesis of Sulfated Cyanidin-3-<i>O</i>-Glucoside and Cyanidin Metabolites
The metabolism of anthocyanins in humans is still not fully understood, which is partly due to the lack of reference compounds. It is known that sulfation is one way of the complex phase II biotransformation mechanism. Therefore, cyanidin-3-<i>O</i>-glucoside and the cyanidin aglycone we...
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| Format: | Article |
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MDPI AG
2021-04-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/26/8/2146 |
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| author | Sarah Straßmann Maike Passon Andreas Schieber |
| author_facet | Sarah Straßmann Maike Passon Andreas Schieber |
| author_sort | Sarah Straßmann |
| collection | DOAJ |
| description | The metabolism of anthocyanins in humans is still not fully understood, which is partly due to the lack of reference compounds. It is known that sulfation is one way of the complex phase II biotransformation mechanism. Therefore, cyanidin-3-<i>O</i>-glucoside and the cyanidin aglycone were chemically converted to their sulfates by reaction with sulfur trioxide-N-triethylamine complex in dimethylformamide. The reaction products were characterized by UHPLC coupled to linear ion trap and IMS-QTOF mass spectrometry. Based on MS data, retention times, and UV-Vis spectra, the compounds could tentatively be assigned to A-, C-, or B-ring sulfates. Analysis of urine samples from two volunteers after ingestion of commercial blackberry nectar demonstrated the presence of two sulfated derivatives of the cyanidin aglycone and one sulfated derivative of the cyanidin-3-<i>O</i>-glucoside. It was found that both the A ring and the B ring are sulfated by human enzymes. This study marks an important step toward a better understanding of anthocyanin metabolism. |
| first_indexed | 2024-03-10T12:29:42Z |
| format | Article |
| id | doaj.art-2eb79185284c449e8669b6b517e26fda |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T12:29:42Z |
| publishDate | 2021-04-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-2eb79185284c449e8669b6b517e26fda2023-11-21T14:42:33ZengMDPI AGMolecules1420-30492021-04-01268214610.3390/molecules26082146Chemical Hemisynthesis of Sulfated Cyanidin-3-<i>O</i>-Glucoside and Cyanidin MetabolitesSarah Straßmann0Maike Passon1Andreas Schieber2Department of Nutritional and Food Sciences, Molecular Food Technology, University of Bonn, Friedrich-Hirzebruch-Allee 7, D-53115 Bonn, GermanyDepartment of Nutritional and Food Sciences, Molecular Food Technology, University of Bonn, Friedrich-Hirzebruch-Allee 7, D-53115 Bonn, GermanyDepartment of Nutritional and Food Sciences, Molecular Food Technology, University of Bonn, Friedrich-Hirzebruch-Allee 7, D-53115 Bonn, GermanyThe metabolism of anthocyanins in humans is still not fully understood, which is partly due to the lack of reference compounds. It is known that sulfation is one way of the complex phase II biotransformation mechanism. Therefore, cyanidin-3-<i>O</i>-glucoside and the cyanidin aglycone were chemically converted to their sulfates by reaction with sulfur trioxide-N-triethylamine complex in dimethylformamide. The reaction products were characterized by UHPLC coupled to linear ion trap and IMS-QTOF mass spectrometry. Based on MS data, retention times, and UV-Vis spectra, the compounds could tentatively be assigned to A-, C-, or B-ring sulfates. Analysis of urine samples from two volunteers after ingestion of commercial blackberry nectar demonstrated the presence of two sulfated derivatives of the cyanidin aglycone and one sulfated derivative of the cyanidin-3-<i>O</i>-glucoside. It was found that both the A ring and the B ring are sulfated by human enzymes. This study marks an important step toward a better understanding of anthocyanin metabolism.https://www.mdpi.com/1420-3049/26/8/2146anthocyaninscyanidin-3-<i>O</i>-glucosidecyanidinLC-IMSHRMSsulfation |
| spellingShingle | Sarah Straßmann Maike Passon Andreas Schieber Chemical Hemisynthesis of Sulfated Cyanidin-3-<i>O</i>-Glucoside and Cyanidin Metabolites Molecules anthocyanins cyanidin-3-<i>O</i>-glucoside cyanidin LC-IMS HRMS sulfation |
| title | Chemical Hemisynthesis of Sulfated Cyanidin-3-<i>O</i>-Glucoside and Cyanidin Metabolites |
| title_full | Chemical Hemisynthesis of Sulfated Cyanidin-3-<i>O</i>-Glucoside and Cyanidin Metabolites |
| title_fullStr | Chemical Hemisynthesis of Sulfated Cyanidin-3-<i>O</i>-Glucoside and Cyanidin Metabolites |
| title_full_unstemmed | Chemical Hemisynthesis of Sulfated Cyanidin-3-<i>O</i>-Glucoside and Cyanidin Metabolites |
| title_short | Chemical Hemisynthesis of Sulfated Cyanidin-3-<i>O</i>-Glucoside and Cyanidin Metabolites |
| title_sort | chemical hemisynthesis of sulfated cyanidin 3 i o i glucoside and cyanidin metabolites |
| topic | anthocyanins cyanidin-3-<i>O</i>-glucoside cyanidin LC-IMS HRMS sulfation |
| url | https://www.mdpi.com/1420-3049/26/8/2146 |
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