A DFT−Based Mechanism Analysis of the Cyclodextrin Inclusion on the Radical Scavenging Activity of Apigenin
Natural flavonoids are renowned for their exceptional antioxidant properties, but their limited water solubility hampers their bioavailability. One approach to enhancing their water solubility and antioxidant activity involves the use of cyclodextrin (CD) inclusion. This study investigated the impac...
| Main Authors: | , , , |
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| Format: | Article |
| Language: | English |
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MDPI AG
2023-11-01
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| Series: | Antioxidants |
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| Online Access: | https://www.mdpi.com/2076-3921/12/11/2018 |
| _version_ | 1797460335962095616 |
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| author | Xiaoping Zheng Yapeng Du Yu Chai Yanzhen Zheng |
| author_facet | Xiaoping Zheng Yapeng Du Yu Chai Yanzhen Zheng |
| author_sort | Xiaoping Zheng |
| collection | DOAJ |
| description | Natural flavonoids are renowned for their exceptional antioxidant properties, but their limited water solubility hampers their bioavailability. One approach to enhancing their water solubility and antioxidant activity involves the use of cyclodextrin (CD) inclusion. This study investigated the impact of CD inclusion on the three primary radical scavenging mechanisms associated with flavonoid antioxidant activity, utilizing apigenin as a representative flavonoid and employing density functional theory (DFT) calculations. Initially, the optimized geometries of CD−apigenin inclusion complexes were analyzed, revealing the formation of hydrogen bonds between CD and apigenin. In less polar environments, the inclusion complex strengthened the bond dissociation enthalpies of hydroxyl groups, thereby reducing antioxidant activity. Conversely, in polar environments, the inclusion complex had the opposite effect by lowering proton affinity. These findings align with experimental results demonstrating that CD inclusion complexation enhances flavonoid antioxidant activity in aqueous ethanol solutions. |
| first_indexed | 2024-03-09T17:04:33Z |
| format | Article |
| id | doaj.art-7a21dab0374e4d07bda967f83a8943ed |
| institution | Directory Open Access Journal |
| issn | 2076-3921 |
| language | English |
| last_indexed | 2024-03-09T17:04:33Z |
| publishDate | 2023-11-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Antioxidants |
| spelling | doaj.art-7a21dab0374e4d07bda967f83a8943ed2023-11-24T14:26:07ZengMDPI AGAntioxidants2076-39212023-11-011211201810.3390/antiox12112018A DFT−Based Mechanism Analysis of the Cyclodextrin Inclusion on the Radical Scavenging Activity of ApigeninXiaoping Zheng0Yapeng Du1Yu Chai2Yanzhen Zheng3College of Ocean Food and Biological Engineering, Jimei University, Xiamen 361021, ChinaCollege of Ocean Food and Biological Engineering, Jimei University, Xiamen 361021, ChinaCollege of Ocean Food and Biological Engineering, Jimei University, Xiamen 361021, ChinaCollege of Ocean Food and Biological Engineering, Jimei University, Xiamen 361021, ChinaNatural flavonoids are renowned for their exceptional antioxidant properties, but their limited water solubility hampers their bioavailability. One approach to enhancing their water solubility and antioxidant activity involves the use of cyclodextrin (CD) inclusion. This study investigated the impact of CD inclusion on the three primary radical scavenging mechanisms associated with flavonoid antioxidant activity, utilizing apigenin as a representative flavonoid and employing density functional theory (DFT) calculations. Initially, the optimized geometries of CD−apigenin inclusion complexes were analyzed, revealing the formation of hydrogen bonds between CD and apigenin. In less polar environments, the inclusion complex strengthened the bond dissociation enthalpies of hydroxyl groups, thereby reducing antioxidant activity. Conversely, in polar environments, the inclusion complex had the opposite effect by lowering proton affinity. These findings align with experimental results demonstrating that CD inclusion complexation enhances flavonoid antioxidant activity in aqueous ethanol solutions.https://www.mdpi.com/2076-3921/12/11/2018apigeninflavonoidantioxidative activitydensity functional theorycyclodextrin inclusion |
| spellingShingle | Xiaoping Zheng Yapeng Du Yu Chai Yanzhen Zheng A DFT−Based Mechanism Analysis of the Cyclodextrin Inclusion on the Radical Scavenging Activity of Apigenin Antioxidants apigenin flavonoid antioxidative activity density functional theory cyclodextrin inclusion |
| title | A DFT−Based Mechanism Analysis of the Cyclodextrin Inclusion on the Radical Scavenging Activity of Apigenin |
| title_full | A DFT−Based Mechanism Analysis of the Cyclodextrin Inclusion on the Radical Scavenging Activity of Apigenin |
| title_fullStr | A DFT−Based Mechanism Analysis of the Cyclodextrin Inclusion on the Radical Scavenging Activity of Apigenin |
| title_full_unstemmed | A DFT−Based Mechanism Analysis of the Cyclodextrin Inclusion on the Radical Scavenging Activity of Apigenin |
| title_short | A DFT−Based Mechanism Analysis of the Cyclodextrin Inclusion on the Radical Scavenging Activity of Apigenin |
| title_sort | dft based mechanism analysis of the cyclodextrin inclusion on the radical scavenging activity of apigenin |
| topic | apigenin flavonoid antioxidative activity density functional theory cyclodextrin inclusion |
| url | https://www.mdpi.com/2076-3921/12/11/2018 |
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