(7S,8R)-3,5,3′-trimethoxy-4′,7-epoxy-8,5′-neolignan-4,9,9′-triol 9-O-α-L-rhamnopyranoside

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 2-芳基苯并呋喃类黄酮
• 英文名称: (7S,8R)-3,5,3′-trimethoxy-4′,7-epoxy-8,5′-neolignan-4,9,9′-triol 9-O-α-L-rhamnopyranoside
• 英文别名: chaenomiside A；(2R,3R,4R,5R,6S)-2-[[(2S,3R)-2-(4-hydroxy-3,5-dimethoxyphenyl)-5-(3-hydroxypropyl)-7-methoxy-2,3-dihydro-1-benzofuran-3-yl]methoxy]-6-methyloxane-3,4,5-triol
• 化学式: C₂₇H₃₆O₁₁
• 分子量: 536.576
• InChiKey: DAPCPLQFHONFRT-NKMYOPCVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  38
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  157
• 氢给体数：
  5
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (7S,8R)-3,5,3′-trimethoxy-4′,7-epoxy-8,5′-neolignan-4,9,9′-triol 9-O-α-L-rhamnopyranoside 在 naringinase from Penicillum 作用下， 以 水 为溶剂， 反应 24.0h， 生成 5-methoxy-trans-dihydrodehydrodiconiferyl alcohol 、 L-鼠李糖
  参考文献：
  名称：

  Lignan Glycosides from the Twigs of Chaenomeles sinensis and Their Biological Activities

  摘要：

  Phytochemical investigation of the twigs of Chaenomeles sinensis led to the isolation and identification of six new lignan glycosides, chaenomiside A-F (1-6), along with five known ones (7-11). Their chemical structures were determined by spectroscopic methods, including NMR, MS, ECD, and GC/MS analyses. All the isolated compounds (1-11) were tested for their inhibitory effects on nitric oxide (NO) production in lipopolysaccharide-activated murine microglial cells and the secretion of nerve growth factor (NGF) in a C6 rat glioma cell line. Compound 6 significantly reduced NO levels in the murine microglia BV2 cells with an IC50 value of 21.3 mu M, and compounds 1, 3, and 6 were potent stimulants of NGF release with stimulation levels of 151.74 +/- 6.77%, 144.31 +/- 7.49%, and 167.61 +/- 18.5%, respectively.

  DOI：

  10.1021/acs.jnatprod.5b00090

文献信息

• Lignan Glycosides from the Twigs of <i>Chaenomeles sinensis</i> and Their Biological Activities
  作者：Chung Sub Kim、Lalita Subedi、Sun Yeou Kim、Sang Un Choi、Ki Hyun Kim、Kang Ro Lee

  DOI：10.1021/acs.jnatprod.5b00090

  日期：2015.5.22

  Phytochemical investigation of the twigs of Chaenomeles sinensis led to the isolation and identification of six new lignan glycosides, chaenomiside A-F (1-6), along with five known ones (7-11). Their chemical structures were determined by spectroscopic methods, including NMR, MS, ECD, and GC/MS analyses. All the isolated compounds (1-11) were tested for their inhibitory effects on nitric oxide (NO) production in lipopolysaccharide-activated murine microglial cells and the secretion of nerve growth factor (NGF) in a C6 rat glioma cell line. Compound 6 significantly reduced NO levels in the murine microglia BV2 cells with an IC50 value of 21.3 mu M, and compounds 1, 3, and 6 were potent stimulants of NGF release with stimulation levels of 151.74 +/- 6.77%, 144.31 +/- 7.49%, and 167.61 +/- 18.5%, respectively.