(23R.24S)-chiogasterol A | 18089-15-1

• 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: (23R.24S)-chiogasterol A
• 英文别名: (23R,24S)-Chiograsterol A；(3S,5S,8R,9S,10R,13S,14S,16S,17R)-17-[(2R,4R,5S)-4,5-dihydroxy-6-methylheptan-2-yl]-3,16-dihydroxy-10,13-dimethyl-1,2,3,4,5,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-6-one
• CAS: 18089-15-1
• 化学式: C₂₇H₄₆O₅
• 分子量: 450.659
• InChiKey: PBANUTGLRFPOSU-GTTOANGYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  98
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (23R.24S)-chiogasterol A 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 16.0h， 生成 (23R,24S)-chiograsterol
  参考文献：
  名称：

  Structure and Bioactivity of Steroidal Saponins Isolated from the Roots of Chamaelirium luteum (False Unicorn)

  摘要：

  Phytochemical investigation of Chamaelirium luteum ("false unicorn") resulted in. the isolation. of 15 steroidal glycoside's. Twelve of these. (1, 2, 4-9, 11-13, and 15) are apparently Unique to this species, and eight of these (6-9, 11-13, and 15) are previously unreported compounds, one (15) possesses a new steroidal aglyeone. In addition, the absolute configuration of (23R,24S)-chiograsterol A (10) was defined, and its full spectroscopic characterization is reported for the first. time The structures and configurations of the saponins were determined using a combination of multistage mass spectrometry (MSn), 1D and 2D NMR experiments, and chemical degradation. The antiproliferative activity of nine compounds obtained in the present work, and eight related compounds generated in previous work, was compared in six human tumor cell lines, with aglycones 3 and 10 and related derivatives 16, 17, 19, and 20 all displaying significant antiproliferative activity.

  DOI：

  10.1021/np300393y
• 作为产物：
  描述：

  (23R,24S)-3-[(β-D-glucopyranosyl)oxy]-16β,23,24-trihydroxy-5α-cholestan-6-one 在 alpha-L-rhamnosidase 作用下， 以 aq. acetate buffer 为溶剂， 反应 24.0h， 以0.7 mg的产率得到(23R.24S)-chiogasterol A
  参考文献：
  名称：

  New cholestane glycosides and sterols from the underground parts of Chamaelirium luteum and their cytotoxic activity

  摘要：

  从 Chamaelirium luteum（百合科）的地下部分分离出了六种新的胆甾烷苷（1、5、6、10、12 和 13）和两种新的甾醇（9 和 11），以及五种已知化合物（2-4、7 和 8）。这些新化合物的结构是通过光谱分析和水解裂解结果确定的。评估了分离出的化合物和苷元对 HL-60 人类白血病细胞的细胞毒性活性。化合物 6a、10a、12a、13 和 13a 对 HL-60 细胞具有细胞毒性，IC50 值分别为 12.8、9.8、15.3、6.2 和 10.2 µM。

  DOI：

  10.1007/s11418-012-0718-z

文献信息

• Structure and Bioactivity of Steroidal Saponins Isolated from the Roots of <i>Chamaelirium luteum</i> (False Unicorn)
  作者：Victoria L. Challinor、Julia M. U. Stuthe、Peter G. Parsons、Lynette K. Lambert、Reginald P. Lehmann、William Kitching、James J. De Voss

  DOI：10.1021/np300393y

  日期：2012.8.24

  Phytochemical investigation of Chamaelirium luteum ("false unicorn") resulted in. the isolation. of 15 steroidal glycoside's. Twelve of these. (1, 2, 4-9, 11-13, and 15) are apparently Unique to this species, and eight of these (6-9, 11-13, and 15) are previously unreported compounds, one (15) possesses a new steroidal aglyeone. In addition, the absolute configuration of (23R,24S)-chiograsterol A (10) was defined, and its full spectroscopic characterization is reported for the first. time The structures and configurations of the saponins were determined using a combination of multistage mass spectrometry (MSn), 1D and 2D NMR experiments, and chemical degradation. The antiproliferative activity of nine compounds obtained in the present work, and eight related compounds generated in previous work, was compared in six human tumor cell lines, with aglycones 3 and 10 and related derivatives 16, 17, 19, and 20 all displaying significant antiproliferative activity.
• New cholestane glycosides and sterols from the underground parts of Chamaelirium luteum and their cytotoxic activity
  作者：Akihito Yokosuka、Kenichi Takagi、Yoshihiro Mimaki

  DOI：10.1007/s11418-012-0718-z

  日期：2013.7

  Six new cholestane glycosides (1, 5, 6, 10, 12, and 13) and two new sterols (9 and 11), along with five known compounds (2–4, 7, and 8), were isolated from the underground parts of Chamaelirium luteum (Liliaceae). The structures of these new compounds were determined by spectroscopic analysis and the results of hydrolytic cleavage. The isolated compounds and aglycones were evaluated for their cytotoxic activity against HL-60 human leukemia cells. Compounds 6a, 10a, 12a, 13, and 13a were cytotoxic to HL-60 cells, with IC50 values of 12.8, 9.8, 15.3, 6.2, and 10.2 µM, respectively.

  从 Chamaelirium luteum（百合科）的地下部分分离出了六种新的胆甾烷苷（1、5、6、10、12 和 13）和两种新的甾醇（9 和 11），以及五种已知化合物（2-4、7 和 8）。这些新化合物的结构是通过光谱分析和水解裂解结果确定的。评估了分离出的化合物和苷元对 HL-60 人类白血病细胞的细胞毒性活性。化合物 6a、10a、12a、13 和 13a 对 HL-60 细胞具有细胞毒性，IC50 值分别为 12.8、9.8、15.3、6.2 和 10.2 µM。