Antioxidant Activity of Sulfate Metabolites of Chlorogenic Acid
This study aimed to determine the antioxidant properties of the sulfate monoesters of ferulic, caffeic, dihydroferulic and dihydrocaffeic acids, the main metabolites of chlorogenic acids. These compounds are not commercially available, so they were synthesized in the laboratory. The LC-MS/MS analysi...
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MDPI AG
2023-02-01
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| Series: | Applied Sciences |
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| Online Access: | https://www.mdpi.com/2076-3417/13/4/2192 |
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| author | Malgorzata Rogozinska Kamil Lisiecki Zbigniew Czarnocki Magdalena Biesaga |
| author_facet | Malgorzata Rogozinska Kamil Lisiecki Zbigniew Czarnocki Magdalena Biesaga |
| author_sort | Malgorzata Rogozinska |
| collection | DOAJ |
| description | This study aimed to determine the antioxidant properties of the sulfate monoesters of ferulic, caffeic, dihydroferulic and dihydrocaffeic acids, the main metabolites of chlorogenic acids. These compounds are not commercially available, so they were synthesized in the laboratory. The LC-MS/MS analysis allowed for the full characterization of these derivatives, which has made them reliable standards for further research. Purified metabolites including ferulic acid-4-<i>O</i>-sulfate, caffeic acid-4-<i>O</i>-sulfate and caffeic acid-3-<i>O</i>-sulfate, dihydrocaffeic acid-4-<i>O</i>-sulfate and caffeic acid-3-<i>O</i>-sulfate were examined for their antioxidant capacities and compared to their precursor compounds using Folin–Ciocalteu, CUPRAC (cupric ion—reducing) and DPPH• (2,2-diphenyl-1-picrylhydrazyl) methods. This study shows that hydrogenation of caffeic and ferulic acids into dihydrocaffeic and dihydroferulic acids has a positive influence on their reducing properties. Moreover, all synthesized sulfate monoesters exhibited very weak antioxidant properties compared to precursor compounds. The presented results show that the transformation of phenolic acids via sulfation leads to the inhibition of antioxidant properties due to the blockage of hydroxyl groups. |
| first_indexed | 2024-03-11T09:13:32Z |
| format | Article |
| id | doaj.art-ea80462b2a294cb0bdc730d22bc41fec |
| institution | Directory Open Access Journal |
| issn | 2076-3417 |
| language | English |
| last_indexed | 2024-03-11T09:13:32Z |
| publishDate | 2023-02-01 |
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| record_format | Article |
| series | Applied Sciences |
| spelling | doaj.art-ea80462b2a294cb0bdc730d22bc41fec2023-11-16T18:52:10ZengMDPI AGApplied Sciences2076-34172023-02-01134219210.3390/app13042192Antioxidant Activity of Sulfate Metabolites of Chlorogenic AcidMalgorzata Rogozinska0Kamil Lisiecki1Zbigniew Czarnocki2Magdalena Biesaga3Faculty of Chemistry, University of Warsaw, Pasteur 1 Street, 02-093 Warsaw, PolandFaculty of Chemistry, University of Warsaw, Pasteur 1 Street, 02-093 Warsaw, PolandFaculty of Chemistry, University of Warsaw, Pasteur 1 Street, 02-093 Warsaw, PolandFaculty of Chemistry, University of Warsaw, Pasteur 1 Street, 02-093 Warsaw, PolandThis study aimed to determine the antioxidant properties of the sulfate monoesters of ferulic, caffeic, dihydroferulic and dihydrocaffeic acids, the main metabolites of chlorogenic acids. These compounds are not commercially available, so they were synthesized in the laboratory. The LC-MS/MS analysis allowed for the full characterization of these derivatives, which has made them reliable standards for further research. Purified metabolites including ferulic acid-4-<i>O</i>-sulfate, caffeic acid-4-<i>O</i>-sulfate and caffeic acid-3-<i>O</i>-sulfate, dihydrocaffeic acid-4-<i>O</i>-sulfate and caffeic acid-3-<i>O</i>-sulfate were examined for their antioxidant capacities and compared to their precursor compounds using Folin–Ciocalteu, CUPRAC (cupric ion—reducing) and DPPH• (2,2-diphenyl-1-picrylhydrazyl) methods. This study shows that hydrogenation of caffeic and ferulic acids into dihydrocaffeic and dihydroferulic acids has a positive influence on their reducing properties. Moreover, all synthesized sulfate monoesters exhibited very weak antioxidant properties compared to precursor compounds. The presented results show that the transformation of phenolic acids via sulfation leads to the inhibition of antioxidant properties due to the blockage of hydroxyl groups.https://www.mdpi.com/2076-3417/13/4/2192phenolic acidssulfate metabolitesantioxidant activityLC-MS/MS |
| spellingShingle | Malgorzata Rogozinska Kamil Lisiecki Zbigniew Czarnocki Magdalena Biesaga Antioxidant Activity of Sulfate Metabolites of Chlorogenic Acid Applied Sciences phenolic acids sulfate metabolites antioxidant activity LC-MS/MS |
| title | Antioxidant Activity of Sulfate Metabolites of Chlorogenic Acid |
| title_full | Antioxidant Activity of Sulfate Metabolites of Chlorogenic Acid |
| title_fullStr | Antioxidant Activity of Sulfate Metabolites of Chlorogenic Acid |
| title_full_unstemmed | Antioxidant Activity of Sulfate Metabolites of Chlorogenic Acid |
| title_short | Antioxidant Activity of Sulfate Metabolites of Chlorogenic Acid |
| title_sort | antioxidant activity of sulfate metabolites of chlorogenic acid |
| topic | phenolic acids sulfate metabolites antioxidant activity LC-MS/MS |
| url | https://www.mdpi.com/2076-3417/13/4/2192 |
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