(25R)-26-O-β-D-glucopyranosyl-5α-furostan-2α,3β,22α,26-tetraol 3-O-[β-D-glucopyranosyl-(1->4)-O-β-D-galactopyranoside]

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: (25R)-26-O-β-D-glucopyranosyl-5α-furostan-2α,3β,22α,26-tetraol 3-O-[β-D-glucopyranosyl-(1->4)-O-β-D-galactopyranoside]
• 英文别名: (2R,3R,4S,5S,6R)-2-[(2R)-4-[(1R,2S,4S,6R,7S,8R,9S,12S,13S,15R,16R,18S)-16-[(2R,3R,4R,5R,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-15-hydroxy-6-methoxy-7,9,13-trimethyl-5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosan-6-yl]-2-methylbutoxy]-6-ethyloxane-3,4,5-triol
• 化学式: C₄₇H₈₀O₁₉
• 分子量: 949.141
• InChiKey: YFVRZAGSWNPJDH-GNNAVRGYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  66
• 可旋转键数：
  14
• 环数：
  8.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  296
• 氢给体数：
  11
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  (25R)-26-O-β-D-glucopyranosyl-5α-furostan-2α,3β,22α,26-tetraol 3-O-[β-D-glucopyranosyl-(1->4)-O-β-D-galactopyranoside] 在 盐酸 作用下， 以 水 为溶剂， 反应 4.0h， 生成 D-葡萄糖 、 D-吡喃葡萄糖
  参考文献：
  名称：

  Antiproliferative steroidal glycosides from Digitalis ciliata

  摘要：

  Two new compounds, a furostanol glycoside (1) and a pregnane glycoside (4), along with eight known compounds, belonging to the classes of spirostane (2,3), pregnane (5-7) and cardenolide (8-10) glycosides, were isolated from the seeds of Digitalis ciliata. Their structures were elucidated by 1D and 2D-NMR experiments as well as ESI-MS analysis. For the first time pregnane glycosides of the diginigenin series have been isolated from D. ciliata. The cytotoxic effects of compounds 1-10 on cell viability of several cancer cell lines, namely human breast cancer (MCF-7), human glioblastoma (T98G), human lung adenocarcinoma (A549), human colon carcinoma (HT-29), and human prostate cancer (PC-3) cell lines were evaluated. Compounds 1, 4, 7 and 8 showed antiproliferative effects against MCF-7, HT-29 and A549 cancer cells with IC50 values ranging from 8.3 to 20 mu M. The effects of compounds 1-10 on cell proliferation were evaluated on these three cancer cell lines by cell cycle analysis of DNA content using flow cytometry. Compounds 7, 8 and 10 induced significant changes in G(2)/M cell cycle phase of all analyzed cells. The obtained results indicate that compounds 7, 8 and 10 are cytostatic compounds effective in reducing cell proliferation by inducing accumulation of the cells in the G(2)/M phase of the cell cycle. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.fitote.2011.12.020

文献信息

• Antiproliferative steroidal glycosides from Digitalis ciliata
  作者：Angela Perrone、Anna Capasso、Michela Festa、Ether Kemertelidze、Cosimo Pizza、Alexandre Skhirtladze、Sonia Piacente

  DOI：10.1016/j.fitote.2011.12.020

  日期：2012.4

  Two new compounds, a furostanol glycoside (1) and a pregnane glycoside (4), along with eight known compounds, belonging to the classes of spirostane (2,3), pregnane (5-7) and cardenolide (8-10) glycosides, were isolated from the seeds of Digitalis ciliata. Their structures were elucidated by 1D and 2D-NMR experiments as well as ESI-MS analysis. For the first time pregnane glycosides of the diginigenin series have been isolated from D. ciliata. The cytotoxic effects of compounds 1-10 on cell viability of several cancer cell lines, namely human breast cancer (MCF-7), human glioblastoma (T98G), human lung adenocarcinoma (A549), human colon carcinoma (HT-29), and human prostate cancer (PC-3) cell lines were evaluated. Compounds 1, 4, 7 and 8 showed antiproliferative effects against MCF-7, HT-29 and A549 cancer cells with IC50 values ranging from 8.3 to 20 mu M. The effects of compounds 1-10 on cell proliferation were evaluated on these three cancer cell lines by cell cycle analysis of DNA content using flow cytometry. Compounds 7, 8 and 10 induced significant changes in G(2)/M cell cycle phase of all analyzed cells. The obtained results indicate that compounds 7, 8 and 10 are cytostatic compounds effective in reducing cell proliferation by inducing accumulation of the cells in the G(2)/M phase of the cell cycle. (C) 2012 Elsevier B.V. All rights reserved.