Structure Characterization of Four New Sesquiterpene Pyridine Alkaloids from <i>Tripterygium wilfordii</i> Hook. f. and Anti-Inflammatory Activity Evaluations
Sesquiterpene pyridine alkaloids (SPAs), as a main class of components in <i>Tripterygium wilfordii</i> Hook. f., possess a variety of bioactivities, such as immunosuppressive, insecticidal, and anti-tumor activities. SPAs can be structurally classed into four subtypes: wilfordate-, evon...
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2024-11-01
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| author | Yong-Jian Wang Jian-Gong Yan Zhong-Mou Zhang Qiu-Fang Fang Ya-Dan Wang Shuang-Cheng Ma |
| author_facet | Yong-Jian Wang Jian-Gong Yan Zhong-Mou Zhang Qiu-Fang Fang Ya-Dan Wang Shuang-Cheng Ma |
| author_sort | Yong-Jian Wang |
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| description | Sesquiterpene pyridine alkaloids (SPAs), as a main class of components in <i>Tripterygium wilfordii</i> Hook. f., possess a variety of bioactivities, such as immunosuppressive, insecticidal, and anti-tumor activities. SPAs can be structurally classed into four subtypes: wilfordate-, evoninate-, iso-wilfordate-, and iso-evoninate types. Our previous study unveiled ten new wilfordate-type SPAs, named wilfordatine A–J, isolated from the roots of <i>Tripterygium wilfordii</i> Hook. f., several of which exhibited significant immunosuppressive activities. As an extension and augmentation of the previous findings, we have now isolated one new iso-wilfordate-type SPA, wilfordatine K (<b>1</b>), alongside three new iso-evoninate-type SPAs, wilfordatines L–N (<b>3</b>–<b>5</b>), and six known analogs. Their structures were characterized by the extensive use of 1D and 2D NMR spectroscopic analysis, as well as HRMS data. Interestingly, compounds <b>4</b> and <b>6</b> were found to exhibit potent inhibitory effects on the nuclear factor-kappa B (NF-κB) pathway in lipopolysaccharide (LPS)-induced HEK293/NF-κB-Luc cells, with IC<sub>50</sub> values of 1.64 μM and 9.05 μM, respectively. Notably, these two compounds had no influence on the cell viability at a concentration of 100 μM. Consequently, they hold significant promise as potential anti-inflammatory candidates for further exploration and development. |
| format | Article |
| id | doaj-art-6c1d17fab0364a1b95edd8fca35a0fc6 |
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| issn | 1420-3049 |
| language | English |
| publishDate | 2024-11-01 |
| publisher | MDPI AG |
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| series | Molecules |
| spelling | doaj-art-6c1d17fab0364a1b95edd8fca35a0fc62025-08-20T01:54:08ZengMDPI AGMolecules1420-30492024-11-012922528410.3390/molecules29225284Structure Characterization of Four New Sesquiterpene Pyridine Alkaloids from <i>Tripterygium wilfordii</i> Hook. f. and Anti-Inflammatory Activity EvaluationsYong-Jian Wang0Jian-Gong Yan1Zhong-Mou Zhang2Qiu-Fang Fang3Ya-Dan Wang4Shuang-Cheng Ma5School of Pharmaceutical, Hebei University of Chinese Medicine, Shijiazhuang 050091, ChinaNational Institutes for Food and Drug Control, Beijing 102629, ChinaSchool of Traditional Chinese Medicine, Beijing University of Chinese Medicine, Beijing 102488, ChinaFaculty of Functional Food and Wine, Shenyang Pharmaceutical University, Shenyang 110016, ChinaNational Institutes for Food and Drug Control, Beijing 102629, ChinaState Key Laboratory of Drug Regulatory Science, Beijing 100050, ChinaSesquiterpene pyridine alkaloids (SPAs), as a main class of components in <i>Tripterygium wilfordii</i> Hook. f., possess a variety of bioactivities, such as immunosuppressive, insecticidal, and anti-tumor activities. SPAs can be structurally classed into four subtypes: wilfordate-, evoninate-, iso-wilfordate-, and iso-evoninate types. Our previous study unveiled ten new wilfordate-type SPAs, named wilfordatine A–J, isolated from the roots of <i>Tripterygium wilfordii</i> Hook. f., several of which exhibited significant immunosuppressive activities. As an extension and augmentation of the previous findings, we have now isolated one new iso-wilfordate-type SPA, wilfordatine K (<b>1</b>), alongside three new iso-evoninate-type SPAs, wilfordatines L–N (<b>3</b>–<b>5</b>), and six known analogs. Their structures were characterized by the extensive use of 1D and 2D NMR spectroscopic analysis, as well as HRMS data. Interestingly, compounds <b>4</b> and <b>6</b> were found to exhibit potent inhibitory effects on the nuclear factor-kappa B (NF-κB) pathway in lipopolysaccharide (LPS)-induced HEK293/NF-κB-Luc cells, with IC<sub>50</sub> values of 1.64 μM and 9.05 μM, respectively. Notably, these two compounds had no influence on the cell viability at a concentration of 100 μM. Consequently, they hold significant promise as potential anti-inflammatory candidates for further exploration and development.https://www.mdpi.com/1420-3049/29/22/5284<i>Tripterygium wilfordii</i>sesquiterpene pyridine alkaloids (SPAs)anti-inflammatory activity |
| spellingShingle | Yong-Jian Wang Jian-Gong Yan Zhong-Mou Zhang Qiu-Fang Fang Ya-Dan Wang Shuang-Cheng Ma Structure Characterization of Four New Sesquiterpene Pyridine Alkaloids from <i>Tripterygium wilfordii</i> Hook. f. and Anti-Inflammatory Activity Evaluations Molecules <i>Tripterygium wilfordii</i> sesquiterpene pyridine alkaloids (SPAs) anti-inflammatory activity |
| title | Structure Characterization of Four New Sesquiterpene Pyridine Alkaloids from <i>Tripterygium wilfordii</i> Hook. f. and Anti-Inflammatory Activity Evaluations |
| title_full | Structure Characterization of Four New Sesquiterpene Pyridine Alkaloids from <i>Tripterygium wilfordii</i> Hook. f. and Anti-Inflammatory Activity Evaluations |
| title_fullStr | Structure Characterization of Four New Sesquiterpene Pyridine Alkaloids from <i>Tripterygium wilfordii</i> Hook. f. and Anti-Inflammatory Activity Evaluations |
| title_full_unstemmed | Structure Characterization of Four New Sesquiterpene Pyridine Alkaloids from <i>Tripterygium wilfordii</i> Hook. f. and Anti-Inflammatory Activity Evaluations |
| title_short | Structure Characterization of Four New Sesquiterpene Pyridine Alkaloids from <i>Tripterygium wilfordii</i> Hook. f. and Anti-Inflammatory Activity Evaluations |
| title_sort | structure characterization of four new sesquiterpene pyridine alkaloids from i tripterygium wilfordii i hook f and anti inflammatory activity evaluations |
| topic | <i>Tripterygium wilfordii</i> sesquiterpene pyridine alkaloids (SPAs) anti-inflammatory activity |
| url | https://www.mdpi.com/1420-3049/29/22/5284 |
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