3β-[(O-β-D-glucopyranosyl)(1->4)-O-β-D-glucopyranosyl)(1->6)-β-D-glucopyranosyl)oxy)]-17α-hydroxy-16β-[(O-(3-O-3,4-dimethoxybenzoyl-β-D-xylopyranosyl)-(1->3)-2-O-acetyl-α-L-arabinopyranosyl)oxy]cholest-5-en-22-one

• 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: 3β-[(O-β-D-glucopyranosyl)(1->4)-O-β-D-glucopyranosyl)(1->6)-β-D-glucopyranosyl)oxy)]-17α-hydroxy-16β-[(O-(3-O-3,4-dimethoxybenzoyl-β-D-xylopyranosyl)-(1->3)-2-O-acetyl-α-L-arabinopyranosyl)oxy]cholest-5-en-22-one
• 英文别名: [(2S,3R,4S,5R)-2-[(2S,3R,4S,5S)-3-acetyloxy-2-[[(3S,8R,9S,10R,13S,14S,16S,17S)-3-[(2R,3R,4S,5S,6R)-6-[[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxy-17-hydroxy-10,13-dimethyl-17-[(2S)-6-methyl-3-oxoheptan-2-yl]-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-16-yl]oxy]-5-hydroxyoxan-4-yl]oxy-3,5-dihydroxyoxan-4-yl] 3,4-dimethoxybenzoate
• 化学式: C₆₆H₁₀₀O₃₁
• 分子量: 1389.5
• InChiKey: UJEXDLZOPXHXKV-JRZLESDCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  97
• 可旋转键数：
  25
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  464
• 氢给体数：
  14
• 氢受体数：
  31

反应信息

• 作为反应物：
  描述：

  3β-[(O-β-D-glucopyranosyl)(1->4)-O-β-D-glucopyranosyl)(1->6)-β-D-glucopyranosyl)oxy)]-17α-hydroxy-16β-[(O-(3-O-3,4-dimethoxybenzoyl-β-D-xylopyranosyl)-(1->3)-2-O-acetyl-α-L-arabinopyranosyl)oxy]cholest-5-en-22-one 在 氢氧化钾 、 sodium methylate 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 3.0h， 生成 (2S)-2-[(3S,8R,9S,10R,13S,14S,16S,17S)-3-[(2R,3R,4S,5S,6R)-6-[[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxy-16-[(2S,3R,4S,5S)-3,5-dihydroxy-4-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-17-hydroxy-10,13-dimethyl-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-yl]-6-methylheptan-3-one
  参考文献：
  名称：

  Cholestane Glycosides from the Bulbs of Ornithogalum thyrsoides and Their Cytotoxic Activity against HL-60 Leukemia Cells

  摘要：

  Twelve bisdesmosidic cholestane glycosides (1-12), including nine new ones (1-9), were isolated from the bulbs of Ornithogalum thyrsoides by monitoring the cytotoxic activity on HL-60 leukemia cells. The structural assignment of the new compounds was carried out by spectroscopic analysis and the results of hydrolytic cleavage. The 3-O-monoglucosides with an aromatic acyl group at the C-16 diglycoside moiety (1, 12) were extremely cytotoxic, with respective IC50 values of 0.00016 and 0.00013 mug/mL, and the other compounds, except for 2, 5, and 8, also showed cytotoxic activity As potent as etoposide (IC50 0.30 mug/mL); used as a positive control. These cholestanes were concluded to contribute to the potent cytotoxicity of the crude O. thyrsoides bulb extract.

  DOI：

  10.1021/np020114j