cleistanthoside A | 86402-39-3

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 木脂素苷
• 英文名称: cleistanthoside A
• 英文别名: 9-(1,3-benzodioxol-5-yl)-4-[(2S,3R,4S,5R)-4,5-dimethoxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-6,7-dimethoxy-3H-benzo[f][2]benzofuran-1-one
• CAS: 86402-39-3
• 化学式: C₃₄H₃₈O₁₆
• 分子量: 702.666
• InChiKey: JBVKVMLXAUHJEJ-LXOHQACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  50
• 可旋转键数：
  10
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  200
• 氢给体数：
  4
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  cleistanthoside A 、 乙酸酐 在 4-二甲氨基吡啶 作用下， 反应 14.0h， 以98%的产率得到cleistanthoside A tetraacetate
  参考文献：
  名称：

  Cytotoxic Arylnaphthalide Lignan Glycosides from the Aerial Parts ofPhyllanthus taxodiifolius

  摘要：

  从税斑叶壳斗树（Phyllanthus taxodiifolius）的地上部分中分离出了四种芳基萘酰木质素苷：税斑叶壳斗苷 (1)、清香苷 A (2)、清香素 A (3) 和清香素 A 甲基醚 (4)，以及一种三萜类化合物，奎胺 (5)。通过光谱和化学方法确定了它们的结构。化合物 3 和 4，以及衍生物 2a 和 3a 在五种培养的哺乳动物癌细胞系中表现出强效的细胞毒性活性，其 GI50 值在 10^-7 到 10^-9 M 范围内，而新化合物 1 显示出中等活性（GI50 约为 10^-6 M）。化合物 2 和 5 在所有测试的细胞系中均无活性。

  DOI：

  10.1055/s-2005-873141
• 作为产物：
  描述：

  cleistanthoside A tetraacetate 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以83%的产率得到cleistanthoside A
  参考文献：
  名称：

  Synthesis and identification of cytotoxic diphyllin glycosides as vacuolar H+-ATPase inhibitors

  摘要：

  The concise syntheses of two natural diphyllin glycosides Cleistanthin-A (CA), Cleistanthoside-A (CleA) and its derivative, Cleistanthoside-A tetraacetate (CleT), have been achieved. They were evaluated for their in vitro anti-proliferative activities against MCF-7, HeLa, HepG2, HCT-116, U251 cancer cell lines by MTT assay. Both of CA and CleT were anti-proliferative to these cancer cells at nanomolar concentrations. They have been shown to inhibit the activity of vacuolar H+-ATPase (V-ATPase) in HepG2 cells and neutralize the pH of lysosomes at nanomolar concentrations. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.06.002

文献信息

• Cytotoxic Arylnaphthalide Lignan Glycosides from the Aerial Parts of<i>Phyllanthus taxodiifolius</i>
  作者：Patoomratana Tuchinda、Anawat Kumkao、Manat Pohmakotr、Samaisukh Sophasan、Thawatchai Santisuk、Vichai Reutrakul

  DOI：10.1055/s-2005-873141

  日期：2006.11

  The arylnaphthalide lignan glycosides, taxodiifoloside (1), cleistanthoside A (2), cleistanthin A (3) and cleistanthin A methyl ether (4), together with a triterpene, glochidone (5), have been isolated from the aerial parts of Phyllanthus taxodiifolius. The structures were established using spectral and chemical methods. Compounds 3 and 4, as well as the derivatives 2a and 3a exhibited potent cytotoxic activities with GI50 values in the range of 10-7 - 10-9 M in five cultured mammalian cancer cell lines while the new compound 1 showed moderate activity (GI50 in the order of 10-6 M). Compounds 2 and 5 were inactive in all tested cell lines.

  从税斑叶壳斗树（Phyllanthus taxodiifolius）的地上部分中分离出了四种芳基萘酰木质素苷：税斑叶壳斗苷 (1)、清香苷 A (2)、清香素 A (3) 和清香素 A 甲基醚 (4)，以及一种三萜类化合物，奎胺 (5)。通过光谱和化学方法确定了它们的结构。化合物 3 和 4，以及衍生物 2a 和 3a 在五种培养的哺乳动物癌细胞系中表现出强效的细胞毒性活性，其 GI50 值在 10^-7 到 10^-9 M 范围内，而新化合物 1 显示出中等活性（GI50 约为 10^-6 M）。化合物 2 和 5 在所有测试的细胞系中均无活性。
• Synthesis and identification of cytotoxic diphyllin glycosides as vacuolar H+-ATPase inhibitors
  作者：Zhitao Zhang、Jinlong Ma、Li Zhu、Yu Zhao

  DOI：10.1016/j.ejmech.2014.06.002

  日期：2014.7

  The concise syntheses of two natural diphyllin glycosides Cleistanthin-A (CA), Cleistanthoside-A (CleA) and its derivative, Cleistanthoside-A tetraacetate (CleT), have been achieved. They were evaluated for their in vitro anti-proliferative activities against MCF-7, HeLa, HepG2, HCT-116, U251 cancer cell lines by MTT assay. Both of CA and CleT were anti-proliferative to these cancer cells at nanomolar concentrations. They have been shown to inhibit the activity of vacuolar H+-ATPase (V-ATPase) in HepG2 cells and neutralize the pH of lysosomes at nanomolar concentrations. (C) 2014 Elsevier Masson SAS. All rights reserved.