Total Synthesis and Anti-Inflammatory Activity of Tectoridin and Related Isoflavone Glucosides
The first total syntheses of four isoflavone glucosides, tectoridin (<b>1</b>), tectoridin A (<b>2</b>), tectorigenin 7-<i>O</i>-β-d-glucopyranosyl-12-<i>O</i>-β-d-glucopyranoside (<b>3</b>), and isotectroigenin 7-<i>O</i>-β-d-glucopyranoside (<b>4</b>), have been accomplished. Key steps in our synthetic approach include a regioselective halogenation reaction, followed by methanolysis to introduce the -OCH<sub>3</sub> group into isoflavone frameworks and a PTC-promoted stereoselective glycosidation to establish glycosidic bonds. The synthesized isoflavone glucosides (<b>1</b>-<b>4</b>) and their corresponding aglycones (<b>32</b> and <b>34</b>) were evaluated for anti-inflammatory activity against nitric oxide (NO), tumor necrosis factor-α (TNF-α), interleukin-6 (IL-6), and interleukin-1 β (IL-1β) in lipopolysaccharide (LPS)-induced RAW264.7 cells. Aglycones <b>32</b> and <b>34</b> exhibited stronger anti-inflammatory activity <i>in vitro</i> compared to isoflavone glucosides <b>1</b>-<b>4</b>.
Authors
- Hongbo Dong (ORCID: https://orcid.org/0000-0001-7024-5343)
- Yujiao He
- Ling Mei (ORCID: https://orcid.org/0000-0002-2762-2235)
- Ting Peng (ORCID: https://orcid.org/0000-0003-1458-1603)
- Yufei Che
- Wang Na (ORCID: https://orcid.org/0000-0002-5940-2499)
- Xiuli Yang
- Yuanwei You
Institutions
- Chengdu University (CN)
- Antibiotic (Bulgaria) (BG)
- Chengdu University of Traditional Chinese Medicine (CN)
Publication Details
- Journal
- Journal of Natural Products
- Published
- 2024-12-28
- DOI
- https://doi.org/10.1021/acs.jnatprod.4c01108
- Citations
- 3
- Primary Topic
- Natural product bioactivities and synthesis
- Type
- article
- Field-Weighted Citation Impact
- 0.70
Funders
- National Natural Science Foundation of China
- Department of Science and Technology of Sichuan Province