(3S,5R,6R,7E,9S)-3,5,6,9-tetrahydroxymegastigman-7-ene

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (3S,5R,6R,7E,9S)-3,5,6,9-tetrahydroxymegastigman-7-ene
• 英文别名: (3S,5R,6R,7E,9S)-megastiman-7-ene-3,5,6,9-tetrolor；7-megastigmene-3,5,6,9-tetrol；aripuanin；kiwiionol；(3S,5R,6R,7E,9S)-Megastigman-7-ene-3,5,6,9-tetrol; 3S,5R,6R,9S-Tetrahydroxymegastigman-7-ene；(1R,2R,4S)-1-[(3R)-3-hydroxybut-1-enyl]-2,6,6-trimethylcyclohexane-1,2,4-triol
• 化学式: C₁₃H₂₄O₄
• 分子量: 244.331
• InChiKey: CTCKPFXFWVNGLG-LYIQGSDWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  80.9
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3S,5R,6R,7E,9S)-3,5,6,9-tetrahydroxymegastigman-7-ene 、 甲氧基-三氟甲基苯 以 氘代吡啶 为溶剂， 反应 8.0h， 生成
  参考文献：
  名称：

  Inhibitory constituents from the aerial parts of Polygala tenuifolia on LPS-induced NO production in BV2 microglia cells

  摘要：

  Five new phenolic glycosides, tenuisides A-E (1-5), and a new megastigmane glycoside, tenuiside F (6), along with seventeen known compounds (7-23) were isolated from the aerial parts of Polygala tenuifolia Willd. Their structures were established by detailed analysis of NMR and HRESIMS spectroscopic data, and the absolute configurations of compounds 5 and 6 were determined by CD spectra and in-NMR-tube Mosher's method. The inhibitory effects of these compounds were evaluated on NO production in LPS-activated BV-2 microglia cells. Compound 17 showed the strongest activity, with an IC50 value of 7.4 mu M, while compounds 1, 8, 14, and 18 showed the moderate activities, with IC50 values of 16.2-38.5 mu M. And their primary structure-activity relationships (SARs) of NO inhibitory effects were also briefly discussed. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.08.085
• 作为产物：
  描述：

  (3S,5R,6S,7E,9R)-7-megastigmene-3,6,9-triol 3-O-β-D-[2'-O-β-D-(6''-O-sinapoyl)apiofuranosyl]glucopyranoside 在 hesperidinase 、 β-glucosidase 、 potassium carbonate 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 92.0h， 生成 (3S,5R,6R,7E,9S)-3,5,6,9-tetrahydroxymegastigman-7-ene
  参考文献：
  名称：

  Inhibitory constituents from the aerial parts of Polygala tenuifolia on LPS-induced NO production in BV2 microglia cells

  摘要：

  Five new phenolic glycosides, tenuisides A-E (1-5), and a new megastigmane glycoside, tenuiside F (6), along with seventeen known compounds (7-23) were isolated from the aerial parts of Polygala tenuifolia Willd. Their structures were established by detailed analysis of NMR and HRESIMS spectroscopic data, and the absolute configurations of compounds 5 and 6 were determined by CD spectra and in-NMR-tube Mosher's method. The inhibitory effects of these compounds were evaluated on NO production in LPS-activated BV-2 microglia cells. Compound 17 showed the strongest activity, with an IC50 value of 7.4 mu M, while compounds 1, 8, 14, and 18 showed the moderate activities, with IC50 values of 16.2-38.5 mu M. And their primary structure-activity relationships (SARs) of NO inhibitory effects were also briefly discussed. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.08.085

文献信息

• Inhibitory constituents from the aerial parts of Polygala tenuifolia on LPS-induced NO production in BV2 microglia cells
  作者：Tian-Xing Shi、Shu Wang、Ke-Wu Zeng、Peng-Fei Tu、Yong Jiang

  DOI：10.1016/j.bmcl.2013.08.085

  日期：2013.11

  Five new phenolic glycosides, tenuisides A-E (1-5), and a new megastigmane glycoside, tenuiside F (6), along with seventeen known compounds (7-23) were isolated from the aerial parts of Polygala tenuifolia Willd. Their structures were established by detailed analysis of NMR and HRESIMS spectroscopic data, and the absolute configurations of compounds 5 and 6 were determined by CD spectra and in-NMR-tube Mosher's method. The inhibitory effects of these compounds were evaluated on NO production in LPS-activated BV-2 microglia cells. Compound 17 showed the strongest activity, with an IC50 value of 7.4 mu M, while compounds 1, 8, 14, and 18 showed the moderate activities, with IC50 values of 16.2-38.5 mu M. And their primary structure-activity relationships (SARs) of NO inhibitory effects were also briefly discussed. (C) 2013 Elsevier Ltd. All rights reserved.