2α,3β,13α,18α-tetrahydroxyl-15,20:18,20-diepoxy-13,14:14,15-disecopregna-5-eno-14-oicacid-16β-lactone-3-O-α-D-oleandropyranosyl-(1→4)-β-D-digitoxo-pyranosyl-(1→4)-β-D-oleandropyranoside

• 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: 2α,3β,13α,18α-tetrahydroxyl-15,20:18,20-diepoxy-13,14:14,15-disecopregna-5-eno-14-oicacid-16β-lactone-3-O-α-D-oleandropyranosyl-(1→4)-β-D-digitoxo-pyranosyl-(1→4)-β-D-oleandropyranoside
• 化学式: C₄₁H₆₄O₁₇
• 分子量: 828.949
• InChiKey: MDAKZIAFQKTWNO-CXCBSHNOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.17
• 重原子数：
  58.0
• 可旋转键数：
  8.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  219.75
• 氢给体数：
  5.0
• 氢受体数：
  17.0

反应信息

• 作为反应物：
  描述：

  2α,3β,13α,18α-tetrahydroxyl-15,20:18,20-diepoxy-13,14:14,15-disecopregna-5-eno-14-oicacid-16β-lactone-3-O-α-D-oleandropyranosyl-(1→4)-β-D-digitoxo-pyranosyl-(1→4)-β-D-oleandropyranoside 在 硫酸 作用下， 以 甲醇 为溶剂， 反应 15.0h， 生成 头孢噻肟 、 D-oleandrose
  参考文献：
  名称：

  Cytotoxic and apoptosis-inducing activity of C21 steroids from the roots of Cynanchum atratum

  摘要：

  Two new (1-2) and two known C-21 steroids (3-4) were isolated from the roots of Cynanchum atratum. Their structures were elucidated by detailed 1D and 2D spectroscopic. The MIT assay showed that compounds 1-4 displayed obvious cytotoxic activities against HepG2 cells with IC50 values ranging from 10.19 mu M to 76.12 mu M. Compounds 1-3 also exhibited cytotoxic effects in A549 cells with IC50 values of 30.87-95.39 mu M. Compound 3 showed the antiproliferative activity via GO/G1 cell cycle arrest and proapoptosis in HepG2 cells by Flowcytometry analysis. Western blotting analysis revealed that compound 3 could induce HepG2 cell apoptosis via the mitochondrial pathway by downregulating Bcl-2 expression, upregulating Bax protein expression, and activating caspase-9 and caspase-3. (C) 2017 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2017.03.004

文献信息

• Cytotoxic and apoptosis-inducing activity of C21 steroids from the roots of Cynanchum atratum
  作者：Jian Zhang、Lin Ma、Zheng-Feng Wu、Shu-Le Yu、Lei Wang、Wen-Cai Ye、Qing-Wen Zhang、Zhi-Qi Yin

  DOI：10.1016/j.steroids.2017.03.004

  日期：2017.6

  Two new (1-2) and two known C-21 steroids (3-4) were isolated from the roots of Cynanchum atratum. Their structures were elucidated by detailed 1D and 2D spectroscopic. The MIT assay showed that compounds 1-4 displayed obvious cytotoxic activities against HepG2 cells with IC50 values ranging from 10.19 mu M to 76.12 mu M. Compounds 1-3 also exhibited cytotoxic effects in A549 cells with IC50 values of 30.87-95.39 mu M. Compound 3 showed the antiproliferative activity via GO/G1 cell cycle arrest and proapoptosis in HepG2 cells by Flowcytometry analysis. Western blotting analysis revealed that compound 3 could induce HepG2 cell apoptosis via the mitochondrial pathway by downregulating Bcl-2 expression, upregulating Bax protein expression, and activating caspase-9 and caspase-3. (C) 2017 Elsevier Inc. All rights reserved.