3-hydroxy-4,5-dimethoxyphenol-1-O-α-L-rhamnopyranosyl-(1->6)-β-D-glucopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-hydroxy-4,5-dimethoxyphenol-1-O-α-L-rhamnopyranosyl-(1->6)-β-D-glucopyranoside
• 英文别名: 1-(α-L-rhamnopyranosyl-(1->6)-β-D-glucopyranosyloxy)-3,4,5-trimethoxybenzene；1-[α-L-rhamnopyranosyl-(1->6)-β-D-glucopyranosyloxy]-3,4,5-trimethoxybenzene；12-O-(α-L-rhamnopyranosyl-(1''-6')-β-D-glucopyranosyloxy)-3,4,5-trimethoxybenzene；(1-α-L-rhamnosyl-(1→6)-O-β-D-glucopyranosyloxy)-3,4,5-trimethoxybenzene；1-(α-L-rhamnosyl-(1→6)-O-β-D-glucopyranosyloxy)-3,4,5-trimethoxybenzene；1-(α-L-rhamnosyl)-(1->6)-β-D-glucopyranosyloxy-3,4,5-trimethoxybenzene；(2S,3R,4R,5R,6R)-2-methyl-6-(((2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(3,4,5-trimethoxyphenoxy)tetrahydro-2H-pyran-2-yl)methoxy)tetrahydro-2H-pyran-3,4,5-triol；(2S,3R,4R,5R,6R)-2-methyl-6-[[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(3,4,5-trimethoxyphenoxy)oxan-2-yl]methoxy]oxane-3,4,5-triol
• 化学式: C₂₁H₃₂O₁₃
• 分子量: 492.477
• InChiKey: FNPXSSIBZAQOBP-PFQYSTRESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  186
• 氢给体数：
  6
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  3-hydroxy-4,5-dimethoxyphenol-1-O-α-L-rhamnopyranosyl-(1->6)-β-D-glucopyranoside 在 盐酸 、 水 作用下， 反应 10.0h， 生成 L-鼠李糖 、 葡萄糖
  参考文献：
  名称：

  Neolignans and Glycosides from the Stem Bark of Illicium difengpi

  摘要：

  Five new neolignans (1-4 and 9), two pairs of neolignan epimers (5-8), and two new aromatic glycosides (10 and 11) have been isolated from the stem bark of Illicium difengpi. Their structures were determined by spectroscopic methods, including 1D and 2D NMR, HRESIMS, CD experiments, and chemical methods. The absolute configurations of the 3,4-diol moiety in 1 and 1,3-diol moiety in 2 were confirmed by Snarzke's method, observing the induced circular dichroism after addition of dimolybdenum tetraacetate in DMSO. Compounds 3, 4, and 11 exhibited moderate anti-inflammatory activities with IC50 values ranging from 1.62 to 24.4 mu M, while compound 3 displayed antioxidant activity with an IC50 value of 42.3 mu M.

  DOI：

  10.1021/np900712v

文献信息

• Neolignans and Glycosides from the Stem Bark of <i>Illicium difengpi</i>
  作者：Lei Fang、Dan Du、Guang-Zhi Ding、Yi-Kang Si、Shi-Shan Yu、Yang Liu、Wen-Jie Wang、Shuang-Gang Ma、Song Xu、Jing Qu、Jia-Ming Wang、Yu-Xi Liu

  DOI：10.1021/np900712v

  日期：2010.5.28

  Five new neolignans (1-4 and 9), two pairs of neolignan epimers (5-8), and two new aromatic glycosides (10 and 11) have been isolated from the stem bark of Illicium difengpi. Their structures were determined by spectroscopic methods, including 1D and 2D NMR, HRESIMS, CD experiments, and chemical methods. The absolute configurations of the 3,4-diol moiety in 1 and 1,3-diol moiety in 2 were confirmed by Snarzke's method, observing the induced circular dichroism after addition of dimolybdenum tetraacetate in DMSO. Compounds 3, 4, and 11 exhibited moderate anti-inflammatory activities with IC50 values ranging from 1.62 to 24.4 mu M, while compound 3 displayed antioxidant activity with an IC50 value of 42.3 mu M.