Synthesis and evaluation of novel hesperidin selenium-enriched derivatives as potential anti-inflammatory and antioxidant agents
Hesperidin is a widely available and important flavonoid, but its insufficient activity has limited its application in the food and medicine industry. Therefore, we combined selenium with hesperidin according to the synergistic effect, selenylation modification of hesperidin was carried out through...
| Main Authors: | , , , , , , , , |
|---|---|
| Other Authors: | |
| Format: | Journal Article |
| Language: | English |
| Published: |
2024
|
| Subjects: | |
| Online Access: | https://hdl.handle.net/10356/180257 |
| _version_ | 1826126760652046336 |
|---|---|
| author | Zhang, Peipei Zhang, Shanshan Hu, Haijuan Hu, Tan Shi, Kaixin Xu, Yang Xu, Gang Hu, Hao Pan, Siyi |
| author2 | School of Materials Science and Engineering |
| author_facet | School of Materials Science and Engineering Zhang, Peipei Zhang, Shanshan Hu, Haijuan Hu, Tan Shi, Kaixin Xu, Yang Xu, Gang Hu, Hao Pan, Siyi |
| author_sort | Zhang, Peipei |
| collection | NTU |
| description | Hesperidin is a widely available and important flavonoid, but its insufficient activity has limited its application in the food and medicine industry. Therefore, we combined selenium with hesperidin according to the synergistic effect, selenylation modification of hesperidin was carried out through a thermal-assisted one-step reaction with selenium dioxide. Two products, 2′,3′-selenium-3,5-dihydroxy-4′-methoxy-7-rhamnoglucoside, 2′,3-selenium-3′,5-dihydroxy-4′-methoxy-7-rhamnoglucoside were obtained, with selenium contents of 120.60 ± 1.12 mg/g and 123.19 ± 1.54 mg/g, respectively. Structural elucidation revealed that the hesperidin was successfully introduced into selenium moiety, and produced C2[dbnd]C3 double bond, C3–OH reactive group in C-ring. The ability of hesperidin selenium-enriched derivatives to scavenge free radicals such as DPPH•, ABTS•+, and •OH was obviously higher than that of hesperidin, and they had a significant inhibitory effect on the LPS-induced inflammatory response in RAW264.7 cells. In this effort, the novel hesperidin selenium-enriched derivatives were successfully synthesized for the first time, which provides new ideas for the expanded application of hesperidin. |
| first_indexed | 2024-10-01T06:57:38Z |
| format | Journal Article |
| id | ntu-10356/180257 |
| institution | Nanyang Technological University |
| language | English |
| last_indexed | 2024-10-01T06:57:38Z |
| publishDate | 2024 |
| record_format | dspace |
| spelling | ntu-10356/1802572024-09-25T06:16:29Z Synthesis and evaluation of novel hesperidin selenium-enriched derivatives as potential anti-inflammatory and antioxidant agents Zhang, Peipei Zhang, Shanshan Hu, Haijuan Hu, Tan Shi, Kaixin Xu, Yang Xu, Gang Hu, Hao Pan, Siyi School of Materials Science and Engineering Medicine, Health and Life Sciences Hesperidin Selenium Hesperidin is a widely available and important flavonoid, but its insufficient activity has limited its application in the food and medicine industry. Therefore, we combined selenium with hesperidin according to the synergistic effect, selenylation modification of hesperidin was carried out through a thermal-assisted one-step reaction with selenium dioxide. Two products, 2′,3′-selenium-3,5-dihydroxy-4′-methoxy-7-rhamnoglucoside, 2′,3-selenium-3′,5-dihydroxy-4′-methoxy-7-rhamnoglucoside were obtained, with selenium contents of 120.60 ± 1.12 mg/g and 123.19 ± 1.54 mg/g, respectively. Structural elucidation revealed that the hesperidin was successfully introduced into selenium moiety, and produced C2[dbnd]C3 double bond, C3–OH reactive group in C-ring. The ability of hesperidin selenium-enriched derivatives to scavenge free radicals such as DPPH•, ABTS•+, and •OH was obviously higher than that of hesperidin, and they had a significant inhibitory effect on the LPS-induced inflammatory response in RAW264.7 cells. In this effort, the novel hesperidin selenium-enriched derivatives were successfully synthesized for the first time, which provides new ideas for the expanded application of hesperidin. This work was supported by China Agriculture Research System of MOF and MARA (CARS-26-07 B), Fundamental Research Funds for the Central Universities (Program No. 2662020SPPY011), Major Special Projects and Key R&D Projects in Yunnan Province (No. 202102AE090054), Major Special Projects and Key R&D Projects in Hubei Province: Research and Demonstration of Key Technologies for Processing Citrus Quick-frozen Products (NO. 2022BBA0030). 2024-09-25T06:16:29Z 2024-09-25T06:16:29Z 2024 Journal Article Zhang, P., Zhang, S., Hu, H., Hu, T., Shi, K., Xu, Y., Xu, G., Hu, H. & Pan, S. (2024). Synthesis and evaluation of novel hesperidin selenium-enriched derivatives as potential anti-inflammatory and antioxidant agents. Food Bioscience, 58, 103651-. https://dx.doi.org/10.1016/j.fbio.2024.103651 2212-4292 https://hdl.handle.net/10356/180257 10.1016/j.fbio.2024.103651 2-s2.0-85187277812 58 103651 en Food Bioscience © 2024 Elsevier Ltd. All rights reserved. |
| spellingShingle | Medicine, Health and Life Sciences Hesperidin Selenium Zhang, Peipei Zhang, Shanshan Hu, Haijuan Hu, Tan Shi, Kaixin Xu, Yang Xu, Gang Hu, Hao Pan, Siyi Synthesis and evaluation of novel hesperidin selenium-enriched derivatives as potential anti-inflammatory and antioxidant agents |
| title | Synthesis and evaluation of novel hesperidin selenium-enriched derivatives as potential anti-inflammatory and antioxidant agents |
| title_full | Synthesis and evaluation of novel hesperidin selenium-enriched derivatives as potential anti-inflammatory and antioxidant agents |
| title_fullStr | Synthesis and evaluation of novel hesperidin selenium-enriched derivatives as potential anti-inflammatory and antioxidant agents |
| title_full_unstemmed | Synthesis and evaluation of novel hesperidin selenium-enriched derivatives as potential anti-inflammatory and antioxidant agents |
| title_short | Synthesis and evaluation of novel hesperidin selenium-enriched derivatives as potential anti-inflammatory and antioxidant agents |
| title_sort | synthesis and evaluation of novel hesperidin selenium enriched derivatives as potential anti inflammatory and antioxidant agents |
| topic | Medicine, Health and Life Sciences Hesperidin Selenium |
| url | https://hdl.handle.net/10356/180257 |
| work_keys_str_mv | AT zhangpeipei synthesisandevaluationofnovelhesperidinseleniumenrichedderivativesaspotentialantiinflammatoryandantioxidantagents AT zhangshanshan synthesisandevaluationofnovelhesperidinseleniumenrichedderivativesaspotentialantiinflammatoryandantioxidantagents AT huhaijuan synthesisandevaluationofnovelhesperidinseleniumenrichedderivativesaspotentialantiinflammatoryandantioxidantagents AT hutan synthesisandevaluationofnovelhesperidinseleniumenrichedderivativesaspotentialantiinflammatoryandantioxidantagents AT shikaixin synthesisandevaluationofnovelhesperidinseleniumenrichedderivativesaspotentialantiinflammatoryandantioxidantagents AT xuyang synthesisandevaluationofnovelhesperidinseleniumenrichedderivativesaspotentialantiinflammatoryandantioxidantagents AT xugang synthesisandevaluationofnovelhesperidinseleniumenrichedderivativesaspotentialantiinflammatoryandantioxidantagents AT huhao synthesisandevaluationofnovelhesperidinseleniumenrichedderivativesaspotentialantiinflammatoryandantioxidantagents AT pansiyi synthesisandevaluationofnovelhesperidinseleniumenrichedderivativesaspotentialantiinflammatoryandantioxidantagents |