State Key Laboratory of Chemical Biology, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China.
University of Chinese Academy of Sciences, Beijing 100049, China.
Sci Adv. 2024 Apr 12;10(15):eadn1305. doi: 10.1126/sciadv.adn1305.
The structural identification and efficient synthesis of bioactive 2,6-dideoxyglycosides are daunting challenges. Here, we report the total synthesis and structural revision of a series of 2,6-dideoxyglycosides from folk medicinal plants and , which feature pregnane steroidal aglycones bearing an 18,20-lactone and glycans consisting of 2,6-dideoxy-3--methyl-β-pyranose residues, including ecdysosides A, B, and F and ecdysantheroside A. All the eight possible 2,6-dideoxy-3--methyl-β-pyranoside stereoisomers (of the proposed ecdysantheroside A) have been synthesized that testify the effective gold(I)-catalyzed glycosylation methods for the synthesis of various 2-deoxy-β-pyranosidic linkages and lays a foundation via nuclear magnetic resonance data mapping to identify these sugar units which occur promiscuously in the present and other natural glycosides. Moreover, some synthetic natural compounds and their isomers have shown promising anticancer, immunosuppressive, anti-inflammatory, and anti-Zika virus activities.
结构鉴定和高效合成具有生物活性的 2,6-二脱氧糖苷是一项艰巨的挑战。在这里，我们报道了一系列来自民间药用植物和的 2,6-二脱氧糖苷的全合成和结构修正，这些糖苷具有孕甾烷甾体苷元，带有 18,20-内酯和由 2,6-二脱氧-3--甲基-β-吡喃糖残基组成的糖苷，包括蜕皮甾苷 A、B 和 F 以及蜕皮甾烷醇 A。所有八种可能的 2,6-二脱氧-3--甲基-β-吡喃糖立体异构体（所提出的蜕皮甾烷醇 A）都已合成，证明了金（I）催化糖苷化方法在合成各种 2-脱氧-β-吡喃糖苷键中的有效性，并通过核磁共振数据映射为鉴定这些在当前和其他天然糖苷中混杂存在的糖单位奠定了基础。此外，一些合成天然化合物及其异构体表现出有希望的抗癌、免疫抑制、抗炎和抗寨卡病毒活性。
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