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Article Abstract
The first total syntheses of four isoflavone glucosides, tectoridin (), tectoridin A (), tectorigenin 7--β-d-glucopyranosyl-12--β-d-glucopyranoside (), and isotectroigenin 7--β-d-glucopyranoside (), have been accomplished. Key steps in our synthetic approach include a regioselective halogenation reaction, followed by methanolysis to introduce the -OCH group into isoflavone frameworks and a PTC-promoted stereoselective glycosidation to establish glycosidic bonds. The synthesized isoflavone glucosides (-) and their corresponding aglycones ( and ) 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 and exhibited stronger anti-inflammatory activity compared to isoflavone glucosides -.
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| http://dx.doi.org/10.1021/acs.jnatprod.4c01108 | DOI Listing |
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