poliothrysoside pentaacetate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: poliothrysoside pentaacetate
• 英文别名: (4-acetoxy-2-acetoxymethyl-phenyl)-(O²,O³,O⁴-triacetyl-O⁶-benzoyl-β-D-glucopyranoside)；(4-Acetoxy-2-acetoxymethyl-phenyl)-(O²,O³,O⁴-triacetyl-O⁶-benzoyl-β-D-glucopyranosid)；Penta-O-acetyl-nigracin；[(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-[4-acetyloxy-2-(acetyloxymethyl)phenoxy]oxan-2-yl]methyl benzoate
• 化学式: C₃₀H₃₂O₁₄
• 分子量: 616.576
• InChiKey: ISXNTLRIVADOQY-OVFYEYCDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  44
• 可旋转键数：
  17
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  176
• 氢给体数：
  0
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  乙酸酐 、 Nigracin; 4-羟基-2-(羟基甲基)苯基 6-苯甲酰 beta-D-吡喃葡萄糖苷 在 吡啶 作用下， 以95%的产率得到poliothrysoside pentaacetate
  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

• Fukui, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1954, vol. 74, p. 735
  作者：Fukui

  DOI：——

  日期：——
• Poliothrysoside and its derivatives as novel insulin sensitizers potentially driving AMPK activation and inhibiting adipogenesis
  作者：Koneni V. Sashidhara、Suriya P. Singh、Salil Varshney、Muheeb Beg、Anil N. Gaikwad

  DOI：10.1016/j.ejmech.2014.09.015

  日期：2014.10

  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.