(20S,22R,24S,25R)-3β-acetylthio-5α,24α-dihydroxy-6α,7α-epoxy-1-oxowithan-26,22-olide | 1312020-90-8

• 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: (20S,22R,24S,25R)-3β-acetylthio-5α,24α-dihydroxy-6α,7α-epoxy-1-oxowithan-26,22-olide
• 英文别名: dioscorolide B；S-[(1S,2S,4S,5R,7R,10R,11S,14R,15R,18S)-5-hydroxy-15-[(1S)-1-[(2R,4S,5R)-4-hydroxy-4,5-dimethyl-6-oxooxan-2-yl]ethyl]-10,14-dimethyl-9-oxo-3-oxapentacyclo[9.7.0.02,4.05,10.014,18]octadecan-7-yl] ethanethioate
• CAS: 1312020-90-8
• 化学式: C₃₀H₄₄O₇S
• 分子量: 548.741
• InChiKey: MXHNLVKWJYKLBK-TWLZKMBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  38
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  139
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  (20S,22R,24S,25R)-5α,24α-dihydroxy-6α,7α-epoxy-1-oxowitha-2-en-26,22-olide 、 硫代乙酸 以 四氢呋喃 为溶剂， 反应 1.0h， 以0.8 mg的产率得到(20S,22R,24S,25R)-3β-acetylthio-5α,24α-dihydroxy-6α,7α-epoxy-1-oxowithan-26,22-olide
  参考文献：
  名称：

  Withanolides from the Rhizomes of Dioscorea japonica and Their Cytotoxicity

  摘要：

  Edible yams are tropical crops that serve as important staple foods in many parts of the world. The rhizome of Dioscorea japonica, well-known as "Japanese yam", is a food and medicinal source known as "San Yak" in Korea. Bioassay-guided fractionation and chemical investigation of the extract of this yam resulted in the identification of two new withanolides, named dioscorolide A (1) and dioscorolide B (2). The structures of these new compounds were determined by spectroscopic methods, induding 1D and 2D nuclear magnetic resonance (NMR) techniques, high-resolution mass spectrometry (HRMS), and chemical methods. The cytotoxic activities of the isolates (1 and 2) were evaluated by determining their inhibitory effects on four human tumor cell lines (A549, SK-OV-3, SK-MEL-2, and HCT15) and a human normal cell line (HUVEC) using a sulforhodamine B (SRB) bioassay. Compounds 1 and 2 showed cytotoxicity against tumor cell lines (A549, SK-OV-3, SK-MEL-2, and HCT15) with IC(50) values ranging from 6.3 to 26.9 mu M and exhibited lower activity against the normal cell line (HUVEC) with IC(50) values ranging from 27.1 to 28.8 mu M, suggesting selective toxicity among tumor and normal cells.

  DOI：

  10.1021/jf2006535