Total Synthesis and Anti-Inflammatory Activity of Tectoridin and Related Isoflavone Glucosides.

IF 3.6 2区生物学 Q2 CHEMISTRY, MEDICINAL Journal of Natural Products Pub Date : 2025-01-24 Epub Date: 2024-12-28 DOI:10.1021/acs.jnatprod.4c01108

Hongbo Dong, Yuanwei You, Xiuli Yang, Ling Mei, Yufei Che, Na Wang, Ting Peng, Yujiao He

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Abstract

The first total syntheses of four isoflavone glucosides, tectoridin (1), tectoridin A (2), tectorigenin 7-O-β-d-glucopyranosyl-12-O-β-d-glucopyranoside (3), and isotectroigenin 7-O-β-d-glucopyranoside (4), have been accomplished. Key steps in our synthetic approach include a regioselective halogenation reaction, followed by methanolysis to introduce the -OCH₃ group into isoflavone frameworks and a PTC-promoted stereoselective glycosidation to establish glycosidic bonds. The synthesized isoflavone glucosides (1-4) and their corresponding aglycones (32 and 34) 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 32 and 34 exhibited stronger anti-inflammatory activity in vitro compared to isoflavone glucosides 1-4.

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鸢尾草苷及相关异黄酮苷的总合成及抗炎活性研究。

首次合成了鸢尾苷(1)、鸢尾苷A(2)、鸢尾苷7-O-β-d-葡萄糖苷基-12- o -β-d-葡萄糖苷(3)和鸢尾苷7-O-β-d-葡萄糖苷(4)四种异黄酮苷类化合物。我们的合成方法的关键步骤包括一个区域选择性卤化反应，然后是甲醇裂解将-OCH3基团引入异黄酮框架和ptc促进的立体选择性糖苷化以建立糖苷键。合成的异黄酮苷（1-4）及其相应的苷元（32和34）对脂多糖（LPS）诱导的RAW264.7细胞中一氧化氮（NO）、肿瘤坏死因子-α (TNF-α)、白细胞介素-6 （IL-6）和白细胞介素-1β (IL-1β)的抗炎活性进行了评价。与异黄酮糖苷1 ~ 4相比，苷元32和34具有较强的体外抗炎活性。

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来源期刊

Journal of Natural Products 生物-药学

CiteScore

9.10

自引率

5.90%

发文量

294

审稿时长

2.3 months

期刊介绍： The Journal of Natural Products invites and publishes papers that make substantial and scholarly contributions to the area of natural products research. Contributions may relate to the chemistry and/or biochemistry of naturally occurring compounds or the biology of living systems from which they are obtained. Specifically, there may be articles that describe secondary metabolites of microorganisms, including antibiotics and mycotoxins; physiologically active compounds from terrestrial and marine plants and animals; biochemical studies, including biosynthesis and microbiological transformations; fermentation and plant tissue culture; the isolation, structure elucidation, and chemical synthesis of novel compounds from nature; and the pharmacology of compounds of natural origin. When new compounds are reported, manuscripts describing their biological activity are much preferred. Specifically, there may be articles that describe secondary metabolites of microorganisms, including antibiotics and mycotoxins; physiologically active compounds from terrestrial and marine plants and animals; biochemical studies, including biosynthesis and microbiological transformations; fermentation and plant tissue culture; the isolation, structure elucidation, and chemical synthesis of novel compounds from nature; and the pharmacology of compounds of natural origin.