Synthesis, Stability, and Antidiabetic Activity Evaluation of (−)-Epigallocatechin Gallate (EGCG) Palmitate Derived from Natural Tea Polyphenols
This work describes a novel approach for the synthesis of (−)-epigallocatechin gallate (EGCG) palmitate by a chemical-synthesis method, where the elevated stability of the EGCG derivative is achieved. Various parameters affecting the acylation process, such as the base, solvent, as well as the molar...
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| Format: | Article |
| Language: | English |
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MDPI AG
2021-01-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/26/2/393 |
| _version_ | 1827601392931438592 |
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| author | Bingbing Liu Zhengzhong Kang Weidong Yan |
| author_facet | Bingbing Liu Zhengzhong Kang Weidong Yan |
| author_sort | Bingbing Liu |
| collection | DOAJ |
| description | This work describes a novel approach for the synthesis of (−)-epigallocatechin gallate (EGCG) palmitate by a chemical-synthesis method, where the elevated stability of the EGCG derivative is achieved. Various parameters affecting the acylation process, such as the base, solvent, as well as the molar ratio of palmitoyl chloride, have been studied to optimize the acylation procedure. The optimized reaction condition was set as follows: EGCG/palmitoyl chloride/sodium acetate was under a molar ratio of 1:2:2, with acetone as the solvent, and the reaction temperature was 40 °C. Under the optimized condition, the yield reached 90.6%. The EGCG palmitate (PEGCG) was isolated and identified as 4′-<i>O</i>-palmitoyl EGCG. Moreover, the stability of PEGCG under different conditions was proved significantly superior to EGCG. Finally, PEGCG showed better inhibition towards α-amylase and α-glucosidase, which was 4.5 and 52 times of EGCG, respectively. Molecular docking simulations confirmed the in vitro assay results. This study set a novel and practical synthetic approach for the derivatization of EGCG, and suggest that PEGCG may act as an antidiabetic agent. |
| first_indexed | 2024-03-09T04:54:49Z |
| format | Article |
| id | doaj.art-18e9cbf07c8340f59614f4e92485952e |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-09T04:54:49Z |
| publishDate | 2021-01-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-18e9cbf07c8340f59614f4e92485952e2023-12-03T13:06:32ZengMDPI AGMolecules1420-30492021-01-0126239310.3390/molecules26020393Synthesis, Stability, and Antidiabetic Activity Evaluation of (−)-Epigallocatechin Gallate (EGCG) Palmitate Derived from Natural Tea PolyphenolsBingbing Liu0Zhengzhong Kang1Weidong Yan2Department of Chemistry, Zhejiang University, Hangzhou 310027, ChinaDepartment of Chemistry, Zhejiang University, Hangzhou 310027, ChinaDepartment of Chemistry, Zhejiang University, Hangzhou 310027, ChinaThis work describes a novel approach for the synthesis of (−)-epigallocatechin gallate (EGCG) palmitate by a chemical-synthesis method, where the elevated stability of the EGCG derivative is achieved. Various parameters affecting the acylation process, such as the base, solvent, as well as the molar ratio of palmitoyl chloride, have been studied to optimize the acylation procedure. The optimized reaction condition was set as follows: EGCG/palmitoyl chloride/sodium acetate was under a molar ratio of 1:2:2, with acetone as the solvent, and the reaction temperature was 40 °C. Under the optimized condition, the yield reached 90.6%. The EGCG palmitate (PEGCG) was isolated and identified as 4′-<i>O</i>-palmitoyl EGCG. Moreover, the stability of PEGCG under different conditions was proved significantly superior to EGCG. Finally, PEGCG showed better inhibition towards α-amylase and α-glucosidase, which was 4.5 and 52 times of EGCG, respectively. Molecular docking simulations confirmed the in vitro assay results. This study set a novel and practical synthetic approach for the derivatization of EGCG, and suggest that PEGCG may act as an antidiabetic agent.https://www.mdpi.com/1420-3049/26/2/393EGCG palmitatemolecular modificationstabilityantidiabetic activitymolecular docking |
| spellingShingle | Bingbing Liu Zhengzhong Kang Weidong Yan Synthesis, Stability, and Antidiabetic Activity Evaluation of (−)-Epigallocatechin Gallate (EGCG) Palmitate Derived from Natural Tea Polyphenols Molecules EGCG palmitate molecular modification stability antidiabetic activity molecular docking |
| title | Synthesis, Stability, and Antidiabetic Activity Evaluation of (−)-Epigallocatechin Gallate (EGCG) Palmitate Derived from Natural Tea Polyphenols |
| title_full | Synthesis, Stability, and Antidiabetic Activity Evaluation of (−)-Epigallocatechin Gallate (EGCG) Palmitate Derived from Natural Tea Polyphenols |
| title_fullStr | Synthesis, Stability, and Antidiabetic Activity Evaluation of (−)-Epigallocatechin Gallate (EGCG) Palmitate Derived from Natural Tea Polyphenols |
| title_full_unstemmed | Synthesis, Stability, and Antidiabetic Activity Evaluation of (−)-Epigallocatechin Gallate (EGCG) Palmitate Derived from Natural Tea Polyphenols |
| title_short | Synthesis, Stability, and Antidiabetic Activity Evaluation of (−)-Epigallocatechin Gallate (EGCG) Palmitate Derived from Natural Tea Polyphenols |
| title_sort | synthesis stability and antidiabetic activity evaluation of epigallocatechin gallate egcg palmitate derived from natural tea polyphenols |
| topic | EGCG palmitate molecular modification stability antidiabetic activity molecular docking |
| url | https://www.mdpi.com/1420-3049/26/2/393 |
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