(20R,22R,24R)-12α,21,27-trihydroxy-1-oxowitha-2,5,24-trienolide | 1340601-49-1

• 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: (20R,22R,24R)-12α,21,27-trihydroxy-1-oxowitha-2,5,24-trienolide
• 英文别名: daturamalakin B；(2R)-2-[(1R)-2-hydroxy-1-[(8S,9S,10R,12S,13S,14S,17R)-12-hydroxy-10,13-dimethyl-1-oxo-4,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]ethyl]-5-(hydroxymethyl)-4-methyl-2,3-dihydropyran-6-one
• CAS: 1340601-49-1
• 化学式: C₂₈H₃₈O₆
• 分子量: 470.606
• InChiKey: KSVNZTZNIXLLPU-JUUSFCBFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  34
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  104
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (20R,22R,24R)-12α,21,27-trihydroxy-1-oxowitha-2,5,24-trienolide-27-O-β-D-glucopyranoside 在 盐酸 、 水 作用下， 反应 4.0h， 生成 可得然胶 、 (20R,22R,24R)-12α,21,27-trihydroxy-1-oxowitha-2,5,24-trienolide
  参考文献：
  名称：

  Cytotoxic activity of withanolides isolated from Tunisian Datura metel L.

  摘要：

  Withanolide-type steroids, withametelin Q (1) and 12 alpha-hydroxydaturametelin B (2) along with three known withanolides, were isolated from leaves of Datura metel L. (Solanaceae). The respective structures, characterized mainly by NMR spectroscopy, were identified as (20R,22R,24R)-21,24-epoxy-1 alpha,3 beta-dihydroxywitha-5,25(27)-dienolide-3-O-beta-D-glucopyranoside (1) and (20R,22R,24R)-12 alpha,21,27-trihydroxy-1-oxowitha-2,5,24-trienolide-27-O-beta-D-glucopyranoside (2). The cytotoxicity of isolated compounds was evaluated against human lung carcinoma cells (A549) and human colorectal adenocarcinoma cells (DLD-1), respectively. Compound 2 exhibited cytotoxicity against A549 and DLD-1 cell lines, with IC50 values of 7 and 2.0 mu M, respectively. However, for compounds 6 and 7, cytotoxicities were higher against DLD-1 cells with IC50 values of 0.6 and 0.7 mu M. Both compounds blocked the cell cycle in the S-phase and induced apoptosis. Crown Copyright (C) 2011 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2011.07.009