ent-16-methoxykauran-19-oic acid methyl ester | 38308-36-0

• 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: ent-16-methoxykauran-19-oic acid methyl ester
• 英文别名: 16α-Methoxy-(-)-kauran-19-saeure-methylester；methyl (1S,4S,5R,9S,10R,13R,14R)-14-methoxy-5,9,14-trimethyltetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylate
• CAS: 38308-36-0
• 化学式: C₂₂H₃₆O₃
• 分子量: 348.526
• InChiKey: QPEPJQKLVIHQQT-DMSOZLTBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ent-16-methoxykauran-19-oic acid methyl ester 在 吡啶 、 chromium(VI) oxide 、 lithium aluminium tetrahydride 、 氧气 作用下， 以 乙醚 、 苯 为溶剂， 生成 16α-methoxy-ent-kauran-19-oic acid
  参考文献：
  名称：

  二萜类的：东方植物药物-XXXIV的化学研究九眼独活：4-轴向醛一些双萜的氧化转化和音符与天然存在的4-羟基-18（或19）norditerpenes

  摘要：

  已经发现二萜（VIII，XII和XVI）的4-轴醛是不稳定的。在室温下易于自氧化的浓缩溶液。阐明了自氧化产物的结构，反应机理和溶剂作用。

  DOI：

  10.1016/0040-4020(72)80034-6
• 作为产物：
  描述：

  贝壳杉烯酸 在 硫酸 作用下， 以 乙醚 为溶剂， 生成 ent-16-methoxykauran-19-oic acid methyl ester
  参考文献：
  名称：

  二萜类的：东方植物药物-XXXIV的化学研究九眼独活：4-轴向醛一些双萜的氧化转化和音符与天然存在的4-羟基-18（或19）norditerpenes

  摘要：

  已经发现二萜（VIII，XII和XVI）的4-轴醛是不稳定的。在室温下易于自氧化的浓缩溶液。阐明了自氧化产物的结构，反应机理和溶剂作用。

  DOI：

  10.1016/0040-4020(72)80034-6

文献信息

• Synthesis and induction of apoptosis signaling pathway of ent-kaurane derivatives
  作者：Idaira Hueso-Falcón、Natalia Girón、Pilar Velasco、Juan M. Amaro-Luis、Angel G. Ravelo、Beatriz de las Heras、Sonsoles Hortelano、Ana Estevez-Braun

  DOI：10.1016/j.bmc.2009.11.064

  日期：2010.2

  Thirty one ent-kaurane derivatives were prepared from kaurenoic acid (1), grandiflorenic acid (16), 15 alpha-acetoxykaurenoic acid (26) and 16 alpha-hydroxy-kaurenoic acid (31). They were tested for their ability to inhibit cell viability in the mouse leukemic macrophagic RAW 264.7 cell line. The most effective compounds were 12, 20, 21, and 23. These were selected for further evaluation in other human cancer cell lines such as Hela, HepG2, and HT-29. Similar effects were obtained although RAW 264.7 cells were more sensitive. In addition, these compounds were significantly less cytotoxic in non-transformed cells. The apoptotic potential of the most active compounds was investigated and they were able to induce apoptosis with compound 12 being the best inducer. The caspase-3, -8 and -9 activities were measured. The results obtained showed that compounds 12, 21, and 23 induce apoptosis via the activation of caspase-8, whereas compound 20 induces apoptosis via caspase-9. Immunoblot analysis of the expression of p53, Bax, Bcl-2, Bcl-xl, and IAPs in RAW 264.7 cells was also carried out. When cells were exposed to 5 mu M of the different compounds, expression levels of p53 and Bax increased whereas levels of antiapoptotic proteins such as Bc1-2, Bc1-x1, and IAPs decreased. In conclusion, kaurane derivatives (12, 20, 21, and 23) induce apoptosis via both the mitochondrial and membrane death receptor pathways, involving the Bcl-2 family proteins. Taken together these results provide a role of kaurane derivatives as apoptotic inducers in tumor cells. (C) 2009 Elsevier Ltd. All rights reserved.
• Chemical studies of oriental plant drugs—XXXIV
  作者：O. Tanaka、S. Mihashi、I. Yanagisawa、T. Nikaido、S. Shibata

  DOI：10.1016/0040-4020(72)80034-6

  日期：1972.1

  It has been found that the 4-axial aldehyde of the diterpenes (VIII, XII and XVI) is labile; a concentrated solution being readily autoxidized at room temperature. The structures of the autoxidation products, the reaction mechanism and the solvent effect have been elucidated.

  已经发现二萜（VIII，XII和XVI）的4-轴醛是不稳定的。在室温下易于自氧化的浓缩溶液。阐明了自氧化产物的结构，反应机理和溶剂作用。