cimigenol-3-O-[4'-O-acetyl-α-L-arabinopyranoside] | 1384384-60-4

• 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: cimigenol-3-O-[4'-O-acetyl-α-L-arabinopyranoside]
• 英文别名: [(3S,4R,5R,6S)-4,5-dihydroxy-6-[[(1S,2R,3S,4R,7R,9S,12R,14S,17R,18R,19R,21R,22S)-2-hydroxy-22-(2-hydroxypropan-2-yl)-3,8,8,17,19-pentamethyl-23,24-dioxaheptacyclo[19.2.1.01,18.03,17.04,14.07,12.012,14]tetracosan-9-yl]oxy]oxan-3-yl] acetate
• CAS: 1384384-60-4
• 化学式: C₃₇H₅₈O₁₀
• 分子量: 662.862
• InChiKey: YKDUSNRQHRGRGM-ZQYCGWMCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  47
• 可旋转键数：
  5
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  144
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  cimigenol-3-O-[4'-O-acetyl-α-L-arabinopyranoside] 在 水 、 potassium carbonate 、 盐酸 作用下， 以 甲醇 为溶剂， 反应 4.0h， 生成 L-(+)-arabinose
  参考文献：
  名称：

  Cytotoxic cycloartane triterpenes from the roots of Cimicifuga heracleifolia

  摘要：

  Phytochemical investigation on the roots of Cimicifuga heracleifolia afforded nine new 9,19-cycloartane triterpenes (1-9), along with seven known constituents (10-16). The new structures were elucidated by spectroscopic and chemical methods. Biological evaluation of the compounds against human HL-60, SMMC-7721, A549, MCF-7, and SW-480 cell lines indicated that eight cimigenol-type compounds (1-3,5, 10-12,14) showed different levels of cytotoxic activities, with IC50 values ranging from 0.83 to 23.94 mu M. In addition, their structural and bioactive features enriched the structure-activity relationships we proposed before. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.05.083

文献信息

• Cytotoxic cycloartane triterpenes from the roots of Cimicifuga heracleifolia
  作者：Yin Nian、Hai-Yan Wang、Jia Su、Lin Zhou、Gang Feng、Yan Li、Ming-Hua Qiu

  DOI：10.1016/j.tet.2012.05.083

  日期：2012.8

  Phytochemical investigation on the roots of Cimicifuga heracleifolia afforded nine new 9,19-cycloartane triterpenes (1-9), along with seven known constituents (10-16). The new structures were elucidated by spectroscopic and chemical methods. Biological evaluation of the compounds against human HL-60, SMMC-7721, A549, MCF-7, and SW-480 cell lines indicated that eight cimigenol-type compounds (1-3,5, 10-12,14) showed different levels of cytotoxic activities, with IC50 values ranging from 0.83 to 23.94 mu M. In addition, their structural and bioactive features enriched the structure-activity relationships we proposed before. (C) 2012 Elsevier Ltd. All rights reserved.