syphonoside

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯类和类似物
• 英文名称: syphonoside
• 英文别名: (1S,8S,9R,12R,13S,14R,16E,22R,27R,28S,29S,30R)-22,28,29,30-tetrahydroxy-9,12,13,16,22-pentamethyl-14-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,19,25,31-tetraoxatetracyclo[25.3.1.04,9.08,13]hentriaconta-4,16-diene-3,20,24-trione
• 化学式: C₃₈H₅₈O₁₇
• 分子量: 786.868
• InChiKey: DLRURNQZBNWYKL-RLPJHZHCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  55
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  268
• 氢给体数：
  8
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  syphonoside 、 sodium methylate 以 甲醇 为溶剂， 反应 1.5h， 以12 mg的产率得到methyl (4aS,5S,6R,8aR)-5-((R,E)-5-hydroxy-3-methyl-1-(((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)pent-3-en-1-yl)-5,6,8a-trimethyl-3,4,4a,5,6,7,8,8a-octahydronaphthalene-1-carboxylate
  参考文献：
  名称：

  Structure and Absolute Stereochemistry of Syphonoside, a Unique Macrocyclic Glycoterpenoid from Marine Organisms

  摘要：

  The glycoterpenoid syphonoside (1) is the main secondary metabolite of both the marine mollusk Syphonota geographica and the sea-grass Halophila stipulacea, two Indo-Pacific species migrated to the Mediterranean Sea through the Suez Canal. The structure and the absolute stereochemistry of 1, which displays unique structural features, has been accomplished by using a combination of spectroscopic techniques, degradation reactions, and conformational analysis methods. Compound 1 was able to inhibit high density induced apoptosis in a number of human and murine carcinoma cell lines.

  DOI：

  10.1021/jo0704917

文献信息

• Structure and Absolute Stereochemistry of Syphonoside, a Unique Macrocyclic Glycoterpenoid from Marine Organisms
  作者：Margherita Gavagnin、Marianna Carbone、Pietro Amodeo、Ernesto Mollo、Rosa Maria Vitale、Vassilios Roussis、Guido Cimino

  DOI：10.1021/jo0704917

  日期：2007.7.1

  The glycoterpenoid syphonoside (1) is the main secondary metabolite of both the marine mollusk Syphonota geographica and the sea-grass Halophila stipulacea, two Indo-Pacific species migrated to the Mediterranean Sea through the Suez Canal. The structure and the absolute stereochemistry of 1, which displays unique structural features, has been accomplished by using a combination of spectroscopic techniques, degradation reactions, and conformational analysis methods. Compound 1 was able to inhibit high density induced apoptosis in a number of human and murine carcinoma cell lines.