4-O-[β-D-glucopyranosyl-(1→2)-α-L-arabinopyranosyl] nervogenic acid lindelofidine ester

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-O-[β-D-glucopyranosyl-(1→2)-α-L-arabinopyranosyl] nervogenic acid lindelofidine ester
• 英文别名: nervosine IV；((1S,7aS)-Hexahydro-1H-pyrrolizin-1-yl)methyl 4-(((2S,3R,4S,5S)-4,5-dihydroxy-3-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)oxy)-3,5-bis(3-methylbut-2-en-1-yl)benzoate；[(1S,8S)-2,3,5,6,7,8-hexahydro-1H-pyrrolizin-1-yl]methyl 4-[(2S,3R,4S,5S)-4,5-dihydroxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-3,5-bis(3-methylbut-2-enyl)benzoate
• 化学式: C₃₆H₅₃NO₁₂
• 分子量: 691.816
• InChiKey: UUYBNFMMBCGDGF-PWHYGFEJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  49
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  188
• 氢给体数：
  6
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  4-O-[β-D-glucopyranosyl-(1→2)-α-L-arabinopyranosyl] nervogenic acid lindelofidine ester 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 1.0h， 生成 倒千里光裂醇
  参考文献：
  名称：

  Pyrrolizidine alkaloids from Liparis nervosa with inhibitory activities against LPS-induced NO production in RAW264.7 macrophages

  摘要：

  Six pyrrolizidine alkaloids were isolated from the whole herb of Liparis nervosa together with two previously known ones. Their structures were elucidated by extensive spectroscopic analyses and chemical reactions. The cytotoxicity of the isolates was evaluated against A549, HepG2, and MCF-7 human cancer cell lines; however, no significant growth inhibition was observed. All compounds were evaluated for the inhibition of LPS-induced nitric oxide (NO) production in RAW264.7 macrophages, and most significantly inhibited NO production with IC50 values in the range of 2.16-38.25 mu M. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2013.03.009

文献信息

• Pyrrolizidine alkaloids from Liparis nervosa with inhibitory activities against LPS-induced NO production in RAW264.7 macrophages
  作者：Shuai Huang、Xian-li Zhou、Cui-juan Wang、You-song Wang、Feng Xiao、Lian-hai Shan、Zhi-yun Guo、Jie Weng

  DOI：10.1016/j.phytochem.2013.03.009

  日期：2013.9

  Six pyrrolizidine alkaloids were isolated from the whole herb of Liparis nervosa together with two previously known ones. Their structures were elucidated by extensive spectroscopic analyses and chemical reactions. The cytotoxicity of the isolates was evaluated against A549, HepG2, and MCF-7 human cancer cell lines; however, no significant growth inhibition was observed. All compounds were evaluated for the inhibition of LPS-induced nitric oxide (NO) production in RAW264.7 macrophages, and most significantly inhibited NO production with IC50 values in the range of 2.16-38.25 mu M. (C) 2013 Elsevier Ltd. All rights reserved.