3β,17β-dihydroxy-28-norolean-12-ene-16-one 3-O-β-d-glucopyranoside

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 3β,17β-dihydroxy-28-norolean-12-ene-16-one 3-O-β-d-glucopyranoside
• 化学式: C₃₅H₅₆O₈
• 分子量: 604.825
• InChiKey: NCQQNUPAMHANOX-APTWFSMOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  43.0
• 可旋转键数：
  3.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  136.68
• 氢给体数：
  5.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  3β,17β-dihydroxy-28-norolean-12-ene-16-one 3-O-β-d-glucopyranoside 在 盐酸 、 水 作用下， 以 甲醇 为溶剂， 反应 4.0h， 生成 D-葡萄糖
  参考文献：
  名称：

  NF-κB inhibitory activities of triterpenoid glycosides from the stems of Acanthopanax senticosus (Rupr. & Maxim.) Harms

  摘要：

  Three new triterpenoid glycosides, 3 beta-hydroxy-28-norolean-12-ene-16-one 3-O-beta-D-glucopyranoside (1), 3 beta,17 beta-dihydroxy-28-norolean-12-ene-16-one 3-O-beta-D-glucopyranoside (2) and 3 beta-hydroxy-olean-12-ene-16,28-lactone 3-O-beta-D-glucopyranoside (3) together with eclalbasaponin II (4) were isolated from Acanthopanax senticosus (Rupr. & Maxim.) Harms. Their structures were elucidated on the basis of spectroscopic and physico-chemical analyses. Inhibition of NF-kappa B of these isolates was measured in HepG2 cells using a luciferase reporter system. Among the isolates, compounds 1,2 and 4 inhibited NF-kappa B activation stimulated by TNF-alpha in a dose-dependent manner, with IC50 values ranging from 8.3 +/- 0.7 to 13.5 +/- 1.0 mu M. (C) 2016 Phytochemical Society of Europe. Published by Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.phytol.2016.01.008

文献信息

• NF-κB inhibitory activities of triterpenoid glycosides from the stems of Acanthopanax senticosus (Rupr. & Maxim.) Harms
  作者：Na Li、Ya-Nan Sun、Le Zhang、Zhen-Dong Tuo、Jia-Lin Li、Pei-Ge Du、Long Cui

  DOI：10.1016/j.phytol.2016.01.008

  日期：2016.3

  Three new triterpenoid glycosides, 3 beta-hydroxy-28-norolean-12-ene-16-one 3-O-beta-D-glucopyranoside (1), 3 beta,17 beta-dihydroxy-28-norolean-12-ene-16-one 3-O-beta-D-glucopyranoside (2) and 3 beta-hydroxy-olean-12-ene-16,28-lactone 3-O-beta-D-glucopyranoside (3) together with eclalbasaponin II (4) were isolated from Acanthopanax senticosus (Rupr. & Maxim.) Harms. Their structures were elucidated on the basis of spectroscopic and physico-chemical analyses. Inhibition of NF-kappa B of these isolates was measured in HepG2 cells using a luciferase reporter system. Among the isolates, compounds 1,2 and 4 inhibited NF-kappa B activation stimulated by TNF-alpha in a dose-dependent manner, with IC50 values ranging from 8.3 +/- 0.7 to 13.5 +/- 1.0 mu M. (C) 2016 Phytochemical Society of Europe. Published by Elsevier B.V. All rights reserved.