Total Synthesis\nand Anti-Inflammatory Activity of\nTectoridin and Related Isoflavone Glucosides

The\nfirst total syntheses of four isoflavone glucosides,\ntectoridin\n(<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\n7-<i>O</i>-β-d-glucopyranoside (<b>4</b>), have been accomplished. Key steps in our synthetic approach include\na regioselective halogenation reaction, followed by methanolysis to\nintroduce the −OCH<sub>3</sub> group into isoflavone frameworks\nand a PTC-promoted stereoselective glycosidation to establish glycosidic\nbonds. 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\nnitric oxide (NO), tumor necrosis factor-α (TNF-α), interleukin-6\n(IL-6), and interleukin-1 β (IL-1β) in lipopolysaccharide\n(LPS)-induced RAW264.7 cells. Aglycones <b>32</b> and <b>34</b> exhibited stronger anti-inflammatory activity <i>in\nvitro</i> compared to isoflavone glucosides <b>1</b>–<b>4</b>.