Nigracin; 4-羟基-2-(羟基甲基)苯基 6-苯甲酰 beta-D-吡喃葡萄糖苷 | 18463-25-7

• 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: Nigracin; 4-羟基-2-(羟基甲基)苯基 6-苯甲酰 beta-D-吡喃葡萄糖苷
• 中文别名: Nigracin;4-羟基-2-(羟基甲基)苯基6-苯甲酰beta-D-吡喃葡萄糖苷
• 英文名称: poliothrysoside
• 英文别名: nigracin；poliothyrsoside；[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[4-hydroxy-2-(hydroxymethyl)phenoxy]oxan-2-yl]methyl benzoate
• CAS: 18463-25-7
• 化学式: C₂₀H₂₂O₉
• 分子量: 406.389
• InChiKey: FLROYCKIIJCTDY-BFMVXSJESA-N

物化性质

• 熔点：
  205 °C (decomp)
• 沸点：
  677.6±55.0 °C(Predicted)
• 密度：
  1.485±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  146
• 氢给体数：
  5
• 氢受体数：
  9

安全信息

• WGK Germany：
  3
• 储存条件：
  存放在2-8℃环境中，应保持干燥并密封。

制备方法与用途

Nigracin（Poliothyrsoside）是一种具有伤口愈合活性的酚苷化合物。

反应信息

• 作为反应物：
  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

• Flacourtosides A–F, Phenolic Glycosides Isolated from <i>Flacourtia ramontchi</i>
  作者：Mélanie Bourjot、Pieter Leyssen、Cécilia Eydoux、Jean-Claude Guillemot、Bruno Canard、Philippe Rasoanaivo、Françoise Guéritte、Marc Litaudon

  DOI：10.1021/np300059n

  日期：2012.4.27

  In an effort to identify novel inhibitors of chikungunya (CHIKV) and dengue (DENY) virus replication, a systematic study with 820 ethyl acetate extracts of madagascan plants was performed in a virus-cell-based assay for CHIKV, and a DENY NS5 RNA-dependent RNA polymerase (RdRp) assay. The extract obtained from the stem bark of Flacourtia ramontchi was selected for its significant activity in both assays. Six new phenolic glycosides, named flacourtosides A-F (1-6), phenolic glycosides itoside H, xylosmin, scolochinenoside D, and polio-thrysoside, and betulinic acid 3 beta-caffeate were obtained using the bioassay-guided isolation process. Their structures were elucidated by comprehensive analyses of NMR spectroscopic and mass spectrometric data. Even though several extracts and fractions showed significant selective antiviral activity in the CHIKV virus-cell-based assay, none of the purified compounds did. However, in the DENY RNA polymerase assay, significant inhibition was observed with betulinic acid 3 beta-caffeate (IC50 = 0.85 +/- 0.1 mu M) and to a lesser extent for the flacourtosides A and E (1 and 5, respectively), and scolochinenoside D (IC50 values similar to 10 mu M).