(25S)-spirost-5-ene-3β,17α,27-triol | 144425-23-0

• 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: (25S)-spirost-5-ene-3β,17α,27-triol
• 英文别名: 25(S)-spirost-5-en-3β,7α,27-triol；(1R,2S,4S,5'S,6R,7S,8S,9S,12S,13R,16S)-5'-(hydroxymethyl)-7,9,13-trimethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-ene-6,2'-oxane]-8,16-diol
• CAS: 144425-23-0
• 化学式: C₂₇H₄₂O₅
• 分子量: 446.627
• InChiKey: FIMRNQIXFDPESW-GPXMTLFMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  32
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  79.2
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (25S)-17α,27-dihydroxyspirost-5-en-3β-yl β-D-glucopyranoside 在 β-D-glucosidase 、 水 作用下， 反应 37.0h， 以1.3 mg的产率得到(25S)-spirost-5-ene-3β,17α,27-triol
  参考文献：
  名称：

  Steroidal glycosides from the underground parts of Trillium erectum and their cytotoxic activity

  摘要：

  Six steroidal glycosides, along with 14 known compounds, were isolated from the underground parts of Trillium erectum L. (Liliaceae). The structures of 1-6 were determined on the basis of extensive spectroscopic analysis, including two-dimensional (2D) NMR data, and a few chemical transformations. The isolated compounds were evaluated for their cytotoxic activity against HL-60 human promyelocytic leukemia cells. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2008.08.004

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。