leonuriside A | 121748-12-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: leonuriside A
• 英文别名: 4-hydroxy-2,6-dimethoxyphenol-1-O-β-D-glucopyranoside；2,6-dimethoxy-p-hydroquinone 1-O-β-D-glucopyranoside；2,6-dimethoxy-4-hydroxyphenol 1-O-β-D-glucopyranoside；leonuriside；(2S,3R,4S,5S,6R)-2-(4-hydroxy-2,6-dimethoxyphenoxy)-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 121748-12-7
• 化学式: C₁₄H₂₀O₉
• 分子量: 332.307
• InChiKey: NOQYJICHFNSIFZ-DIACKHNESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  138
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 leonuriside A 以 甲醇 为溶剂， 反应 1.0h， 生成 2,4,6-三甲氧基苯酚 1-O-beta-D-吡喃葡萄糖苷
  参考文献：
  名称：

  来自马蹄莲的酚葡萄糖苷没食子酸酯

  摘要：

  摘要 从马蹄莲中分离得到5种酚葡萄糖苷没食子酸酯，化学和光谱学表征其结构为4-羟基-2-甲氧基苯酚1-O-β-d-(6′-O-没食子酰)葡萄糖苷，4-羟基- 3-甲氧基苯酚1-O-β-d-(2',6'-二-O-没食子酰基)葡萄糖苷，4-羟基-3-甲氧基苯酚1-O-β-d-2',3',6'-三-O-没食子酰基)葡萄糖苷、3,4,5-三甲氧基苯酚1-O-β-d-(2',6'-二-O-没食子酰基)葡萄糖苷和4-羟基-2,6-二甲氧基苯酚1-O -β-d-(6'-O-没食子酰基)葡糖苷。此外，还证明了几种黄烷-3-醇和原飞燕草素的出现。

  DOI：

  10.1016/s0031-9422(00)98001-4
• 作为产物：
  描述：

  在 水 、 lithium hydroxide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 以12 mg的产率得到二氢菜豆酸
  参考文献：
  名称：

  Anti-inflammatory terpenes from Schefflera rubriflora C. J. Tseng & G. Hoo with their TNF-α and IL-6 inhibitory activities

  摘要：

  The 95% ethanol extract and its EtOAc and n-BuOH fractions obtained from the leaves and twigs of Schefflera rubriflora C. J. Tseng & G. Hoo showed significant inhibitory activities (33.6%, 35.7% and 40.6%, respectively) against croton oil-induced ear inflammation in mice. Bioactivity-guided isolation and separation gave eight previously undescribed terpenes or terpene glycosides. Structural elucidation was based on UV, IR, and NMR spectroscopy, MS, experimental and calculated ECD data, and Mosher's method. To identify anti-inflammatory components from the extract, all the compounds were evaluated for tumor necrosis factor-alpha (TNF-alpha) and interleukine-6 (IL-6) inhibitory activities. Four undescribed compounds inhibited mRNA expression of TNF-alpha and IL-6 with IC50 values of 15.3-52.4 mu M.

  DOI：

  10.1016/j.phytochem.2019.03.021

文献信息

• Phenol glucoside gallates from Mallotus japonicus
  作者：Reiko Saijo、Gen-ichiro Nonaka、Itsuo Nishioka

  DOI：10.1016/s0031-9422(00)98001-4

  日期：1989.1

  Abstract Five phenol glucoside gallates were isolated from Mallotus japonicus , and their structures characterized by chemical and spectroscopic means as 4-hydroxy-2-methoxyphenol 1- O -β- d -(6′- O -galloyl)glucoside, 4-hydroxy-3-methoxyphenol 1- O -β- d -(2′,6′-di- O -galloyl)glucoside, 4-hydroxy-3-methoxyphenol 1- O -β- d -2′,3′,6′-tri- O -galloyl)glucoside, 3,4,5-trimethoxyphenol 1- O -β- d -(2′

  摘要 从马蹄莲中分离得到5种酚葡萄糖苷没食子酸酯，化学和光谱学表征其结构为4-羟基-2-甲氧基苯酚1-O-β-d-(6′-O-没食子酰)葡萄糖苷，4-羟基- 3-甲氧基苯酚1-O-β-d-(2',6'-二-O-没食子酰基)葡萄糖苷，4-羟基-3-甲氧基苯酚1-O-β-d-2',3',6'-三-O-没食子酰基)葡萄糖苷、3,4,5-三甲氧基苯酚1-O-β-d-(2',6'-二-O-没食子酰基)葡萄糖苷和4-羟基-2,6-二甲氧基苯酚1-O -β-d-(6'-O-没食子酰基)葡糖苷。此外，还证明了几种黄烷-3-醇和原飞燕草素的出现。
• Anti-inflammatory terpenes from Schefflera rubriflora C. J. Tseng & G. Hoo with their TNF-α and IL-6 inhibitory activities
  作者：Fenghua Li、Jian Zhang、Mingbao Lin、Xianming Su、Changkang Li、Hongqing Wang、Baoming Li、Ruoyun Chen、Jie Kang

  DOI：10.1016/j.phytochem.2019.03.021

  日期：2019.7

  The 95% ethanol extract and its EtOAc and n-BuOH fractions obtained from the leaves and twigs of Schefflera rubriflora C. J. Tseng & G. Hoo showed significant inhibitory activities (33.6%, 35.7% and 40.6%, respectively) against croton oil-induced ear inflammation in mice. Bioactivity-guided isolation and separation gave eight previously undescribed terpenes or terpene glycosides. Structural elucidation was based on UV, IR, and NMR spectroscopy, MS, experimental and calculated ECD data, and Mosher's method. To identify anti-inflammatory components from the extract, all the compounds were evaluated for tumor necrosis factor-alpha (TNF-alpha) and interleukine-6 (IL-6) inhibitory activities. Four undescribed compounds inhibited mRNA expression of TNF-alpha and IL-6 with IC50 values of 15.3-52.4 mu M.