(3S,5S,8S,9S,10R,13S,14S,17R)-3-Hydroxy-17-((1S,5R)-6-hydroxy-1,5-dimethyl-2-oxo-hexyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-6-one | 117706-67-9

• 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: (3S,5S,8S,9S,10R,13S,14S,17R)-3-Hydroxy-17-((1S,5R)-6-hydroxy-1,5-dimethyl-2-oxo-hexyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-6-one
• 英文别名: (25R)-3β,26-dihydroxy-5α-cholesta-6,22-dione
• CAS: 117706-67-9
• 化学式: C₂₇H₄₄O₄
• 分子量: 432.644
• InChiKey: YOWISIJFACTUPN-UDTKBFGBSA-N

物化性质

• 沸点：
  586.7±30.0 °C(Predicted)
• 密度：
  1.089±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  31.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  74.6
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 (3S,5S,8S,9S,10R,13S,14S,17R)-3-Hydroxy-17-((1S,5R)-6-hydroxy-1,5-dimethyl-2-oxo-hexyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-6-one 在 吡啶 作用下， 生成 Acetic acid (3S,5S,8S,9S,10R,13S,14S,17R)-17-((1S,5R)-6-acetoxy-1,5-dimethyl-2-oxo-hexyl)-10,13-dimethyl-6-oxo-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester
  参考文献：
  名称：

  Studies on the chemical constituents of Lilium henryi BAKER.

  摘要：

  从百合科植物百合的新鲜鳞茎中分离得到了2个新的苦味酚苷和1个甾体葡萄糖苷，通过波谱数据、化学证据及X射线单晶衍射分析确定了它们的结构，分别为：(2S)-1-O-对-甲氧基肉桂酰基-3-O-β-D-吡喃葡萄糖基甘油（甲基罗果苷A）、(2S)-1-O-咖啡酰基-3-O-β-D-吡喃葡萄糖基甘油（罗果苷C）、3-O-阿魏酰基-6'-O-(4-O-β-D-吡喃葡萄糖基阿魏酰基)蔗糖和(25R)-3β，26-二羟基-5α-胆甾烷-6，22-二酮3-O-β-D-吡喃葡萄糖苷，同时还分离并鉴定了几种已知成分。

  DOI：

  10.1248/cpb.36.2430
• 作为产物：
  描述：

  (25R)-3β,26-dihydroxy-5α-cholestane-6,22-dione 3-O-β-D-glucopyranoside 在 β-glucosidese enzime 水 作用下， 反应 24.0h， 生成 (3S,5S,8S,9S,10R,13S,14S,17R)-3-Hydroxy-17-((1S,5R)-6-hydroxy-1,5-dimethyl-2-oxo-hexyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-6-one
  参考文献：
  名称：

  Studies on the chemical constituents of Lilium henryi BAKER.

  摘要：

  从百合科植物百合的新鲜鳞茎中分离得到了2个新的苦味酚苷和1个甾体葡萄糖苷，通过波谱数据、化学证据及X射线单晶衍射分析确定了它们的结构，分别为：(2S)-1-O-对-甲氧基肉桂酰基-3-O-β-D-吡喃葡萄糖基甘油（甲基罗果苷A）、(2S)-1-O-咖啡酰基-3-O-β-D-吡喃葡萄糖基甘油（罗果苷C）、3-O-阿魏酰基-6'-O-(4-O-β-D-吡喃葡萄糖基阿魏酰基)蔗糖和(25R)-3β，26-二羟基-5α-胆甾烷-6，22-二酮3-O-β-D-吡喃葡萄糖苷，同时还分离并鉴定了几种已知成分。

  DOI：

  10.1248/cpb.36.2430

文献信息

• Steroidal glycosides from the bulbs of Lilium speciosum
  作者：Tomoki Iguchi、Akihito Yokosuka、Minpei Kuroda、Mayuko Takeya、Mizuki Hagiya、Yoshihiro Mimaki

  DOI：10.1016/j.phytol.2020.01.008

  日期：2020.6

  Steroidal glycosides (1-21), including eight new spirostanol glycosides (1-8) and a new cholestane glycoside (9), were isolated from the bulbs of Lilium speciosum. The structures of the new compounds were determined based on spectroscopic data analysis and hydrolytic cleavage reactions. The isolated compounds and their aglycones (1a, 8a, and 9a) were evaluated for their cytotoxicity against HL-60 human

  甾体糖苷（1 - 21），包括八个新spirostanol甙（1 - 8）和一个新的胆甾糖苷（9），从鳞茎分离鹿子百合。基于光谱数据分析和水解裂解反应确定了新化合物的结构。评价分离的化合物及其糖苷配基（1a，8a和9a）对HL-60人急性早幼粒细胞白血病细胞和A549人肺癌细胞的细胞毒性。化合物12和21对HL-60和A549细胞具有中等的细胞毒活性，对HL-60细胞的IC 50值分别为6.9μM和5.1μM，对A549细胞的IC 50值分别为7.6μM和4.4μM。化合物20仅显示出对A549细胞的中等细胞毒性，IC 50值为6.7μM。
• 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.