3-hydroxy-4-methoxypropiophenone 3-O-β-D-apiofuranosyl-(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-methoxypropiophenone 3-O-β-D-apiofuranosyl-(1→6)-β-D-glucopyranoside
• 英文别名: Anti-inflammatory agent 29；1-[3-[(2S,3R,4S,5S,6R)-6-[[(2R,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxy-4-methoxyphenyl]propan-1-one
• 化学式: C₂₁H₃₀O₁₂
• 分子量: 474.462
• InChiKey: IYQBBHREUBVRNA-RHAOSNMYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.07
• 重原子数：
  33.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  184.6
• 氢给体数：
  6.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  3-hydroxy-4-methoxypropiophenone 3-O-β-D-apiofuranosyl-(1→6)-β-D-glucopyranoside 在 三氟乙酸 作用下， 反应 10.0h， 生成 D-apiose 、 葡萄糖
  参考文献：
  名称：

  Chemical constituents of Ligusticum chuanxiong and their anti-inflammation and hepatoprotective activities

  摘要：

  Ligusticum chuanxiong Hort is a famous health promoting plant cultivated in China, and widely consumed due to its various curative effects. To study the potential bioactive constituents from the rhizome of L. chuanxiong, a chemical investigation was thus performed. In present study, we report the isolation and identification of ten new compounds, including two coumarins (1-2), four lignans (3-6), and four phenols (7-10), along with five known compounds (11-15) from the rhizome of L. chuanxiong. The structures of these compounds were un-ambiguously established by HR-ESI-MS, UV, IR, CD, NMR spectral data and comparison to reported data. Meanwhile, the anti-inflammation and hepatoprotective activities of all these compounds were evaluated. The results show that compounds 5, 6 and 7 showed excellent inhibition of NO production in LPS-induced RAW 264.7 cells stronger than curcumin, and compounds 5, 7 and 9 exhibited greater hepatoprotective effect than that of bicyclol.

  DOI：

  10.1016/j.bioorg.2020.104016

文献信息

• Chemical constituents of Ligusticum chuanxiong and their anti-inflammation and hepatoprotective activities
  作者：Xiang Yuan、Bing Han、Zi-Ming Feng、Jian-Shuang Jiang、Ya-Nan Yang、Pei-Cheng Zhang

  DOI：10.1016/j.bioorg.2020.104016

  日期：2020.8

  Ligusticum chuanxiong Hort is a famous health promoting plant cultivated in China, and widely consumed due to its various curative effects. To study the potential bioactive constituents from the rhizome of L. chuanxiong, a chemical investigation was thus performed. In present study, we report the isolation and identification of ten new compounds, including two coumarins (1-2), four lignans (3-6), and four phenols (7-10), along with five known compounds (11-15) from the rhizome of L. chuanxiong. The structures of these compounds were un-ambiguously established by HR-ESI-MS, UV, IR, CD, NMR spectral data and comparison to reported data. Meanwhile, the anti-inflammation and hepatoprotective activities of all these compounds were evaluated. The results show that compounds 5, 6 and 7 showed excellent inhibition of NO production in LPS-induced RAW 264.7 cells stronger than curcumin, and compounds 5, 7 and 9 exhibited greater hepatoprotective effect than that of bicyclol.