medigenin | 11052-63-4

• 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: medigenin
• 英文别名: 3-[2-[(1S,4aR,5S,8aR)-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethyl]-2H-furan-5-one
• CAS: 11052-63-4
• 化学式: C₂₀H₃₀O₃
• 分子量: 318.456
• InChiKey: GWLQAIIVWXSSCM-RAUXBKROSA-N

物化性质

• 熔点：
  162-164 °C
• 沸点：
  468.7±18.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  medigenin 在 jones reagent 作用下， 以 乙醚 、 丙酮 为溶剂， 反应 7.0h， 生成 ent-labda-8(17),13-dien-15,16-olid-19-oic acid methyl ester
  参考文献：
  名称：

  In Vitro Platelet-Activating Factor Receptor Binding Inhibitory Activity of Pinusolide Derivatives: A Structure−Activity Study

  摘要：

  Pinusolide, a labdane-type diterpene lactone isolated from Biota orientalis, was found to be a potent platelet-activating factor (PAF) receptor binding antagonist. To investigate the structure-activity relationship and find derivatives with improved pharmacological profiles, 17 pinusolide derivatives were prepared and tested for their ability to inhibit the PAF receptor binding. The results demonstrated that the carboxymethyl ester group at C-19, the integrity of the alpha,beta-unsaturated butenolide ring, and the exocyclic olefinic function of pinusolide are all necessary for its maximum PAF receptor binding inhibitory activity. Among the derivatives, the 17-nor-8-oxo derivative 8 was found to be as potent as pinusolide. The results also suggested that several derivatives warrant further pharmaceutical and pharmacological studies due to their improved water solubility (8 and 11) and apparent lack of susceptibility to Michael-type nucleophilic addition (13 and 18).

  DOI：

  10.1021/jm970569j
• 作为产物：
  描述：

  红松内酯 在 Celite 、 sodium aluminum diethyl dihydride 、 silver carbonate 作用下， 以 乙醚 、 苯 为溶剂， 反应 3.0h， 生成 medigenin
  参考文献：
  名称：

  In Vitro Platelet-Activating Factor Receptor Binding Inhibitory Activity of Pinusolide Derivatives: A Structure−Activity Study

  摘要：

  Pinusolide, a labdane-type diterpene lactone isolated from Biota orientalis, was found to be a potent platelet-activating factor (PAF) receptor binding antagonist. To investigate the structure-activity relationship and find derivatives with improved pharmacological profiles, 17 pinusolide derivatives were prepared and tested for their ability to inhibit the PAF receptor binding. The results demonstrated that the carboxymethyl ester group at C-19, the integrity of the alpha,beta-unsaturated butenolide ring, and the exocyclic olefinic function of pinusolide are all necessary for its maximum PAF receptor binding inhibitory activity. Among the derivatives, the 17-nor-8-oxo derivative 8 was found to be as potent as pinusolide. The results also suggested that several derivatives warrant further pharmaceutical and pharmacological studies due to their improved water solubility (8 and 11) and apparent lack of susceptibility to Michael-type nucleophilic addition (13 and 18).

  DOI：

  10.1021/jm970569j

文献信息

• A labdane diterpene and its glycoside from melodinus monogynus
  作者：Arun Sethi、Anakshi Khare、Maheshwari P. Khare

  DOI：10.1016/0031-9422(88)80137-7

  日期：1988.1

  Abstract A novel labdane diterpene, medigenin, and its glycoside, medinin, have been isolated from the dried root bark of Melodinus monogynus . On the basis of chemical and spectroscopic data the structures have been established as 16,19-dihydroxy-entlabda-8(17)13-diene-15-oic lactone and its 19- O -β-cellobioside, respectively.

  摘要 从Melodinus monogynus 的干燥根皮中分离出一种新型的劳丹烷二萜medigenin 及其苷类medinin。根据化学和光谱数据，这些结构分别被确定为 16,19-dihydroxy-entlabda-8(17)13-diene-15-oic 内酯及其 19-O-β-纤维二糖苷。
• SETHI, ARUN;KHARE, ANAKSHI;KHARE, MAHESHWARI P., PHYTOCHEMISTRY, 27,(1988) N 7, C. 2255-2259
  作者：SETHI, ARUN、KHARE, ANAKSHI、KHARE, MAHESHWARI P.

  DOI：——

  日期：——
• In Vitro Platelet-Activating Factor Receptor Binding Inhibitory Activity of Pinusolide Derivatives: A Structure−Activity Study
  作者：Byung Hoon Han、Hyun Ok Yang、Young-Hwa Kang、Dae-Yeon Suh、Hyun Jung Go、Wan-Jin Song、Yong Chul Kim、Man Ki Park

  DOI：10.1021/jm970569j

  日期：1998.7.1

  Pinusolide, a labdane-type diterpene lactone isolated from Biota orientalis, was found to be a potent platelet-activating factor (PAF) receptor binding antagonist. To investigate the structure-activity relationship and find derivatives with improved pharmacological profiles, 17 pinusolide derivatives were prepared and tested for their ability to inhibit the PAF receptor binding. The results demonstrated that the carboxymethyl ester group at C-19, the integrity of the alpha,beta-unsaturated butenolide ring, and the exocyclic olefinic function of pinusolide are all necessary for its maximum PAF receptor binding inhibitory activity. Among the derivatives, the 17-nor-8-oxo derivative 8 was found to be as potent as pinusolide. The results also suggested that several derivatives warrant further pharmaceutical and pharmacological studies due to their improved water solubility (8 and 11) and apparent lack of susceptibility to Michael-type nucleophilic addition (13 and 18).