(25R)-17α-hydroxyspirost-5-en-3β-yl-O-β-D-glucopyranosyl-(1→4)-O-[α-L-rhamnopyranosyl-(1→2)]-β-D-glucopyranoside

• 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)-17α-hydroxyspirost-5-en-3β-yl-O-β-D-glucopyranosyl-(1→4)-O-[α-L-rhamnopyranosyl-(1→2)]-β-D-glucopyranoside
• 英文别名: (2R,3R,4R,5R,6S)-2-[(2R,3R,4S,5S,6R)-4-hydroxy-6-(hydroxymethyl)-2-[(1R,2S,4S,5'R,6R,7S,8S,9S,12S,13R,16S)-8-hydroxy-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-ene-6,2'-oxane]-16-yl]oxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-3-yl]oxy-6-methyloxane-3,4,5-triol
• 化学式: C₄₅H₇₂O₁₈
• 分子量: 901.056
• InChiKey: JLLOGAYMLWLIEX-BMAPFECUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  63
• 可旋转键数：
  8
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  276
• 氢给体数：
  10
• 氢受体数：
  18

反应信息

• 作为产物：
  描述：

  (25R)-26-[(β-D-glucopyranosyl)oxy]-22α-hydroxy-5β-furostan-3β-yl-O-β-D-glucopyranosyl-(1→4)-O-[α-L-rhamnopyranosyl-(1→2)]-β-D-glucopyranoside 在 β-D-glucosidase 作用下， 以 aq. acetate buffer 为溶剂， 反应 23.0h， 以1 mg的产率得到(25R)-17α-hydroxyspirost-5-en-3β-yl-O-β-D-glucopyranosyl-(1→4)-O-[α-L-rhamnopyranosyl-(1→2)]-β-D-glucopyranoside
  参考文献：
  名称：

  Steroidal glycosides from the bulbs of Fritillaria meleagris and their cytotoxic activities

  摘要：

  Steroidal glycosides (1-18), including 10 new compounds (1-10), were isolated from the bulbs of Fritillaria meleagris (Liliaceae). The structures of the new compounds were determined by two-dimensional (2D) NMR analysis, and by hydrolytic cleavage followed by spectroscopic and chromatographic analysis. The isolated compounds and their aglycones were evaluated for cytotoxic activity against HL-60 human promyelocytic leukemia cells and A549 human lung adenocarcinoma cells. Morphological observation and flow cytometry analysis showed that 5 beta-spirostanol glycoside (2) and a cholestane derivative (17a) induced apoptotic cell death in HL-60 cells through different mechanisms of action. Furthermore, the (22R)-spirosolanol glycoside (11) selectively induced apoptosis in A549 cells without affecting the caspase-3 activity level. (C) 2013 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2013.02.012

文献信息

• Steroidal glycosides from the bulbs of Fritillaria meleagris and their cytotoxic activities
  作者：Yukiko Matsuo、Daisuke Shinoda、Aina Nakamaru、Yoshihiro Mimaki

  DOI：10.1016/j.steroids.2013.02.012

  日期：2013.7

  Steroidal glycosides (1-18), including 10 new compounds (1-10), were isolated from the bulbs of Fritillaria meleagris (Liliaceae). The structures of the new compounds were determined by two-dimensional (2D) NMR analysis, and by hydrolytic cleavage followed by spectroscopic and chromatographic analysis. The isolated compounds and their aglycones were evaluated for cytotoxic activity against HL-60 human promyelocytic leukemia cells and A549 human lung adenocarcinoma cells. Morphological observation and flow cytometry analysis showed that 5 beta-spirostanol glycoside (2) and a cholestane derivative (17a) induced apoptotic cell death in HL-60 cells through different mechanisms of action. Furthermore, the (22R)-spirosolanol glycoside (11) selectively induced apoptosis in A549 cells without affecting the caspase-3 activity level. (C) 2013 Elsevier Inc. All rights reserved.