柳匍匐次苷 | 26652-12-0

• 物质功能分类: 天然产物 - 酚类
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 柳匍匐次苷
• 英文名称: salirepin
• 英文别名: (2S,3R,4S,5S,6R)-2-[4-hydroxy-2-(hydroxymethyl)phenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 26652-12-0
• 化学式: C₁₃H₁₈O₈
• 分子量: 302.281
• InChiKey: NPNFZOGKIFFKGT-UJPOAAIJSA-N

物化性质

• 熔点：
  102-104 °C
• 沸点：
  633.2±55.0 °C(Predicted)
• 密度：
  1.601±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  140
• 氢给体数：
  6
• 氢受体数：
  8

制备方法与用途

生物活性方面，Salirepin 是一种从伊地萨多果（Idesia polycarpa）的果实中提取的酚苷类物质，能够有效抑制由脂多糖诱导的一氧化氮生成。

反应信息

• 作为产物：
  描述：

  Nigracin; 4-羟基-2-(羟基甲基)苯基 6-苯甲酰 beta-D-吡喃葡萄糖苷 在 barium hydroxide octahydrate 、 硫酸 作用下， 以 水 为溶剂， 反应 2.0h， 以99%的产率得到柳匍匐次苷
  参考文献：
  名称：

  Poliothrysoside and its derivatives as novel insulin sensitizers potentially driving AMPK activation and inhibiting adipogenesis

  摘要：

  In our efforts to develop safe and active chemical entities from nature, we first identified poliothrysoside (1), a phytoconstituent isolated from Flacourtia indica, possessing antidiabetic potential. Subsequently, fifteen derivatives (2-16) were synthesized to assess the activity profile of this class. All the compounds were analyzed for their glucose uptake potency in chronic insulin-induced insulin resistant 3T3-L1 adipocytes. Interestingly, compound 2 exhibited strong ability to increase the insulin sensitivity, primarily activating the AMPK signaling pathway and also inhibited the adipogenesis in 3T3-L1 adipocytes, in concentration dependent manner. Overall, these studies suggest the potential of poliothrysoside and its derivatives as promising leads for non-insulin dependent type 2 diabetes (T2D). (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.09.015

文献信息

• Phenyl glycosides from the leaves of Flacourtia indica (Burm. f.) Merr (Salicaceae)
  作者：Phuc-Dam Nguyen、Charlotte Sayagh、Georges Massiot、Catherine Lavaud

  DOI：10.1016/j.phytochem.2021.112891

  日期：2021.10

  Thirteen phenolic glycosides, together with fourteen various known compounds, were isolated from the methanolic extract of leaves of Flacourtia indica. Twelve of these were composed of gentisyl or salicyl alcohols, glycosylated on the phenol and acylated on the primary alcohol with various more or less oxidized forms of pyrocatechuic acid. A number of positions on the glucose or on the acid were further

  从Flacourtia indica叶子的甲醇提取物中分离出 13 种酚苷以及 14 种各种已知化合物. 其中十二个由龙胆醇或水杨醇组成，在苯酚上糖基化，在伯醇上用各种或多或少氧化形式的焦儿茶酸酰化。葡萄糖或酸上的许多位置被苯甲酸或肉桂酸进一步酰化。除此之外，还分离了苯基丙烷的葡糖苷。大体结构通过光谱手段阐明，包括 1D 和 2D NMR 实验和 HR-ESI-MS 分析。其中一些结构，例如木糖蛋白，之前已经描述过，但事实证明，由于文献中没有关于绝对构型的明确数据，很难确定它们的确切身份。
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