(-)-(7R,7'R,7''R,8S,8'S,8''S)-4',4''-dihydroxy-3,3',3'',5-tetramethoxy-7,9':7',9-diepoxy-4,8''-oxy-8,8'-sesquineolignan-7'',9''-diol | 1292294-23-5

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 呋喃类木脂素
• 英文名称: (-)-(7R,7'R,7''R,8S,8'S,8''S)-4',4''-dihydroxy-3,3',3'',5-tetramethoxy-7,9':7',9-diepoxy-4,8''-oxy-8,8'-sesquineolignan-7'',9''-diol
• 英文别名: (1R,2S)-2-[4-[(3R,3aS,6R,6aS)-3-(4-hydroxy-3-methoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-6-yl]-2,6-dimethoxyphenoxy]-1-(4-hydroxy-3-methoxyphenyl)propane-1,3-diol
• CAS: 1292294-23-5
• 化学式: C₃₁H₃₆O₁₁
• 分子量: 584.62
• InChiKey: DVTIDVKFFJRCAB-JBSVPGBZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  42
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  146
• 氢给体数：
  4
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (-)-(7R,7'R,7''R,8S,8'S,8''S)-4',4''-dihydroxy-3,3',3'',5-tetramethoxy-7,9':7',9-diepoxy-4,8''-oxy-8,8'-sesquineolignan-7'',9''-diol 在 sodium hydroxide 、 盐酸 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 120.0h， 以0.9 mg的产率得到(-)-medioresinol
  参考文献：
  名称：

  Lignans and Neolignans from Sinocalamus affinis and Their Absolute Configurations

  摘要：

  Twenty-two new lignans and neolignans (1-22), together with 14 known analogues, have been isolated from an ethanolic extract of the stem (with skin removed) of Sinocalamus affinis. Their structures were elucidated by spectroscopic and chemical methods. On the basis of systematic NMR and circular dichroism (CD) data analysis, the validity of J(7,8) and Delta delta(C8-C7) values to distinguish threo and egthro aryl glycerol units in different neolignans and the CD data [particularly the Rh-2(OCOCF3)(4)-induced CD data (the E band)] to determine the absolute configurations at C-8 (C-7) of the aryl glycerol units are discussed. At a concentration of 10 mu M, compounds 20 and 22 inhibited NO production in mouse peritoneal macrophages 84.2 +/- 5.9% and 71.7 +/- 1.0%, respectively. Compounds 19, 20, and 22 showed activity against serum deprivation induced PC12 cell damage by increasing the cell viability from 80.7 +/- 2.8% to 91.6 +/- 6.4%, 107.2 +/- 8.0%, and 97.6 +/- 8.5%, respectively.

  DOI：

  10.1021/np200117y

文献信息

• Lignans and Neolignans from <i>Sinocalamus affinis</i> and Their Absolute Configurations
  作者：Liang Xiong、Chenggeng Zhu、Yanru Li、Ye Tian、Sheng Lin、Shaopeng Yuan、Jinfeng Hu、Qi Hou、Naihong Chen、Yongchun Yang、Jiangong Shi

  DOI：10.1021/np200117y

  日期：2011.5.27

  Twenty-two new lignans and neolignans (1-22), together with 14 known analogues, have been isolated from an ethanolic extract of the stem (with skin removed) of Sinocalamus affinis. Their structures were elucidated by spectroscopic and chemical methods. On the basis of systematic NMR and circular dichroism (CD) data analysis, the validity of J(7,8) and Delta delta(C8-C7) values to distinguish threo and egthro aryl glycerol units in different neolignans and the CD data [particularly the Rh-2(OCOCF3)(4)-induced CD data (the E band)] to determine the absolute configurations at C-8 (C-7) of the aryl glycerol units are discussed. At a concentration of 10 mu M, compounds 20 and 22 inhibited NO production in mouse peritoneal macrophages 84.2 +/- 5.9% and 71.7 +/- 1.0%, respectively. Compounds 19, 20, and 22 showed activity against serum deprivation induced PC12 cell damage by increasing the cell viability from 80.7 +/- 2.8% to 91.6 +/- 6.4%, 107.2 +/- 8.0%, and 97.6 +/- 8.5%, respectively.