16-(α-D-mannopyranosyloxy)isopimar-7-en-19-oic acid | 1337958-77-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 16-(α-D-mannopyranosyloxy)isopimar-7-en-19-oic acid
• 英文别名: 16-α-D-mannopyranosyloxyisopimar-7-en-19-oic acid；16-alpha-D-mannopyranosyloxyisopimar-7-en-19-oic acid；(1S,4aR,4bS,7S,10aR)-1,4a,7-trimethyl-7-[2-[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyethyl]-3,4,4b,5,6,8,10,10a-octahydro-2H-phenanthrene-1-carboxylic acid
• CAS: 1337958-77-6
• 化学式: C₂₆H₄₂O₈
• 分子量: 482.615
• InChiKey: MHRXJYCBHPYIQC-XDCNHFSSSA-N

物化性质

• 沸点：
  659.8±55.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  34
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  137
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  16-(α-D-mannopyranosyloxy)isopimar-7-en-19-oic acid 在 Jack bean α-mannosidase 、 水 作用下， 反应 24.0h， 以6.1 mg的产率得到16-Hydroxyisopimar-7-en-19-oic acid
  参考文献：
  名称：

  Isopimarane diterpene glycosides, apoptosis inducers, obtained from fruiting bodies of the ascomycete Xylaria polymorpha

  摘要：

  The methanol extract of fruiting bodies of the ascomycete Xylaria polymorpha afforded three isopimarane diterpene glycosides, namely, 16-alpha-D-mannopyranosyloxyisopimar-7-en-19-oic acid (1), 15-hydroxy-16-alpha-D-mannopyranosyloxyisopimar-7-en-19-oic acid (2), and 16-alpha-D-glucopyranosyloxyisopimar-7-en-19-oic acid (3). Their structures were determined by spectroscopic methods and by single-crystal X-ray analysis. They showed cytotoxicity against human cancer cell lines and exhibited IC(50) values ranging from 71 to 607 mu M. Further studies on the cytotoxicity of these compounds against HL60 cells demonstrated that they induced apoptosis along with typical DNA fragmentation. It was observed that 2 was less active than 1 and 3. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2009.03.023

文献信息

• Isopimarane diterpene glycosides, apoptosis inducers, obtained from fruiting bodies of the ascomycete Xylaria polymorpha
  作者：Yoshihito Shiono、Sadayoshi Motoki、Takuya Koseki、Tetsuya Murayama、Masato Tojima、Ken-ichi Kimura

  DOI：10.1016/j.phytochem.2009.03.023

  日期：2009.5

  The methanol extract of fruiting bodies of the ascomycete Xylaria polymorpha afforded three isopimarane diterpene glycosides, namely, 16-alpha-D-mannopyranosyloxyisopimar-7-en-19-oic acid (1), 15-hydroxy-16-alpha-D-mannopyranosyloxyisopimar-7-en-19-oic acid (2), and 16-alpha-D-glucopyranosyloxyisopimar-7-en-19-oic acid (3). Their structures were determined by spectroscopic methods and by single-crystal X-ray analysis. They showed cytotoxicity against human cancer cell lines and exhibited IC(50) values ranging from 71 to 607 mu M. Further studies on the cytotoxicity of these compounds against HL60 cells demonstrated that they induced apoptosis along with typical DNA fragmentation. It was observed that 2 was less active than 1 and 3. (C) 2009 Elsevier Ltd. All rights reserved.