16α-hydroxy-ent-kauranoic acid methyl ester | 22376-08-5

• 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: 16α-hydroxy-ent-kauranoic acid methyl ester
• 英文别名: methyl ent-16β-hydroxykaur-15-(16)en-19-oate；ent-16α-Hydroxykauran-19-saeuremethylester；16α-Hydroxy-kauran-19-saeure-methylester；16alpha-Hydroxy-kaurenoic acid methyl ester；methyl (1S,4S,5R,9S,10R,13R,14R)-14-hydroxy-5,9,14-trimethyltetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylate
• CAS: 22376-08-5
• 化学式: C₂₁H₃₄O₃
• 分子量: 334.499
• InChiKey: NQZVMGVMAPPTFX-IIDSPLMYSA-N

物化性质

• 沸点：
  421.7±38.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.95
• 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：

  16α-hydroxy-ent-kauranoic acid methyl ester 在 吡啶 、 对甲苯磺酰氯 作用下， 生成 kaurenoic acid methyl ester
  参考文献：
  名称：

  Biogenetic-like rearrangements of tetracyclic diterpenes

  摘要：

  DOI：

  10.1021/jo00823a013
• 作为产物：
  描述：

  ent-16α-Acetoxykauran-19-saeuremethylester 在 sodium hydroxide 作用下， 生成 16α-hydroxy-ent-kauranoic acid methyl ester
  参考文献：
  名称：

  Biogenetic-like rearrangements of tetracyclic diterpenes

  摘要：

  DOI：

  10.1021/jo00823a013

文献信息

• New metabolites of Fusarium moniliforme sheld
  作者：E.P. Sbrebryakov、A.V. Simolin、V.F. Kucherov、B.V. Rosynov

  DOI：10.1016/s0040-4020(01)98730-7

  日期：1970.1

  Culture filtrates of Fusarium monoliforme contain 16α-hydroxy-(−)-kauran-19-al (8) and 16α-hydroxy-(−)-kauran-19-oic acid (9)-two diterpenoids related to the intermediates in the biosynthesis of gibberellins. The previously described 7,13-dihydroxykanrenolide (10) is an endogenic metabolite of the fungus. From the mycelium extracts three C28-sterols were isolated including the hitherto unknown 5α-

  镰刀菌的培养滤液中含有16α-羟基-（-）-kauran-19-al（8）和16α-羟基-（-）-kauran-19-oic酸（9）-与生物合成中间体有关的两个二萜赤霉素。先前描述的7，13-二羟基甘露内酯（10）是真菌的内源性代谢产物。从菌丝体提取物中分离出三种C 28-甾醇，包括迄今未知的5α-8α-环氧双酚-6,9（11），22-trien-3β-ol-12-one（19）。菌丝体中氧化的贝壳杉烯衍生物的含量远低于培养滤液中的含量。在菌丝体的脂肪酸中，分离出一种新化合物4-氧十二烷二酸（21）。
• 15-Hydroxy-acetylerioflorin and other constituents from Viguiera linearis
  作者：Guillermo Delgado、Laura Alvarez、Alfonso Romo de Vivar

  DOI：10.1016/s0031-9422(00)80712-8

  日期：1985.10

  Abstract Aerial parts of Viguiera linearis afforded 16α-hydroxy-ent-kauranoic acid, viguiestenin, leptocarpin, acetylleptocarpin, budlein B, clovandiol and the new heliangolide 15-hydroxy-acetylerioflorin.

  摘要 Viguiera linearis 的地上部分提供了 16α-羟基-ent-kauranoic acid、viguiestenin、leptocarpin、acetylleptocarpin、budlein B、clovandiol 和新的 heliangolide 15-hydroxy-acetylerioflorin。
• 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.
• Biogenetic-like rearrangements of tetracyclic diterpenes
  作者：Robert M. Coates、Edward F. Bertram

  DOI：10.1021/jo00823a013

  日期：1971.12