spiroconazol A | 133952-03-1

• 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: spiroconazol A
• 英文别名: (25R)-17α-hydroxyspirost-5-en-3β-yl O-α-L-rhamnopyranosyl-(1→2)-O-[α-L-rhamnopyranosyl-(1→3)]-β-D-glucopyranoside；spiroconazole A；pennogenin 3-O-β-chacotrioside；pennogenin-3-O-α-L-rhamnopyranosyl-(1->3)-[α-L-rhamnopyranosyl-(1->2)]-β-D-glucopyranoside；pennogenin 3-O-α-L-rhamnopyranosyl-(1->2)-[α-L-rhamnopyranosyl-(1->3)]-β-D-glucopyranoside；(2S,3R,4R,5R,6S)-2-[(2R,3R,4S,5R,6R)-3-hydroxy-2-(hydroxymethyl)-6-[(1R,2S,4S,5'R,6R,7S,8S,9S,12S,13R,16S)-8-hydroxy-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-ene-6,2'-oxane]-16-yl]oxy-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-4-yl]oxy-6-methyloxane-3,4,5-triol
• CAS: 133952-03-1
• 化学式: C₄₅H₇₂O₁₇
• 分子量: 885.056
• InChiKey: NLMRPYJFEJTQEC-JQHDQEQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  62
• 可旋转键数：
  7
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  256
• 氢给体数：
  9
• 氢受体数：
  17

反应信息

• 作为产物：
  描述：

  (25R)-17α-hydroxyspirost-5-en-3β-yl O-α-L-rhamnopyranosyl-(1→2)-O-[α-L-rhamnopyranosyl-(1→3)]-4,6-O-diacetyl-β-D-glucopyranoside 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以9.0 mg的产率得到spiroconazol A
  参考文献：
  名称：

  Steroidal glycosides from the underground parts of Dracaena thalioides and their cytotoxic activity

  摘要：

  Six spirostanol glycosides (1-6) and 12 known compounds (7-18) were isolated from the underground parts of Dracaena thalioides (Agavaceae). Their structures were determined by spectroscopic analysis, including 2D NMR spectroscopic data, and chemical transformations. The isolated compounds were evaluated for cytotoxic activity against HL-60 human leukemia cells. Compounds 1,3-6, and 8-18 showed cytotoxicity against HL-60 cells, of which 10, a bisdesmosidic spirostanol derivative, showed potent cytotoxicity against HL-60 cells with an IC50 value of 0.38 mu M and induced apoptosis in HL-60 cells. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2014.07.021