17-oxo-ent-kaur-15(16)-en-19-oic acid methyl ester | 77887-57-1

• 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: 17-oxo-ent-kaur-15(16)-en-19-oic acid methyl ester
• 英文别名: methyl 17-oxo-ent-kaur-15-en-19-oate；methyl (1S,4S,5R,9S,10S,13R)-14-formyl-5,9-dimethyltetracyclo[11.2.1.01,10.04,9]hexadec-14-ene-5-carboxylate
• CAS: 77887-57-1
• 化学式: C₂₁H₃₀O₃
• 分子量: 330.467
• InChiKey: PFGTZJTYYBLGMJ-CQAWWZBVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  17-oxo-ent-kaur-15(16)-en-19-oic acid methyl ester 在 sodium tetrahydroborate 作用下， 生成 17-Hydroxy-ent-isokaur-15-en-saeuremethylester
  参考文献：
  名称：

  三种向日葵物种的 Ent-kauranes 和其他成分

  摘要：

  Helianthus debilis subsp 的抽象空中部分。cucumerifolius、H. occidentalis 和 H. simulans 提供了多种已知和一些未知的 ent-kauranoic 酸。此外，H. occidentalis 还提供了纤毛酸和一种新的生物遗传学相关的 atisane 衍生物 occidentalic acid。除了 ent-kauranes 之外，H. simulans 还提供 heliangolide leptocarpin 和黄酮 hymenoxin。来自这些物种的几种二萜类化合物抑制了向日葵蛾的幼虫生长。

  DOI：

  10.1016/0031-9422(83)80036-3
• 作为产物：
  描述：

  贝壳杉烯酸 在 叔丁基过氧化氢 、 selenium(IV) oxide 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 生成 17-oxo-ent-kaur-15(16)-en-19-oic acid methyl ester
  参考文献：
  名称：

  Fluorination of Kaurenoic Acid Derivatives by Remote Functionalization

  摘要：

  由于发现了可通过引入一个氟原子而改变生物活性的新化合物，Kauranoids 和相关的四环二萜类化合物最近越来越受到人们的关注。本文介绍了通过在 "未活化 "的 C-7 位进行远程官能化而对贝壳杉醇 6 和 7 进行立体特异性氟化的过程。

  DOI：

  10.1055/s-1999-2852

文献信息

• Synthesis and anti-inflammatory activity of ent-kaurene derivatives
  作者：Idaira Hueso-Falcón、Irene Cuadrado、Florencia Cidre、Juan M. Amaro-Luis、Ángel G. Ravelo、Ana Estevez-Braun、Beatriz de las Heras、Sonsoles Hortelano

  DOI：10.1016/j.ejmech.2011.01.052

  日期：2011.4

  inhibition of NF-κB activation might be the mechanism involved in anti-inflammatory effects of these kaurene derivatives. As expected, cytokines IL-6, IL-1α, TNF-α and IFN-γ were downregulated in the presence of compound 28, 55 and 62 after stimulation with LPS. These results indicate that kaurene derivatives might be used for the design of new anti-inflammatory agents.

  制备了一系列的贝壳杉烯衍生物（1 – 63），并评估了其抗炎活性。13种测试化合物能够抑制NO的产生，IC 50为2至10μM。化合物11，12，14和23显示细胞存活力的低百分比，而化合物9，10，17，28，37，48，55，61和62在浓度高达25μM时无细胞毒性。概述了一些结构-活动关系。化合物28，55和62，选择作为代表性的化合物，它们有效地抑制NOS-2蛋白的表达。我们还确定抑制NF-κB活化可能是这些贝壳杉烯衍生物的抗炎作用所涉及的机制。如所预期的，细胞因子IL-6，IL-1α，TNF-α和IFN-γ水平在化合物存在下调28，55和62用LPS刺激后。这些结果表明，kaurene衍生物可用于设计新的抗炎药。
• Tricyclic sesquiterpenes and further diterpenes from Espeletiopsis species
  作者：F. Bohlmann、H. Suding、J. Cuatrecasas、H. Robinson、R.M. King

  DOI：10.1016/s0031-9422(00)91035-5

  日期：1980.1

  Abstract The investigation of five Espeletiopsis and two Coespeletia species afforded, in addition to numerous known compounds, two new kaurene derivatives 19-acetoxy-ent-kaurene and 17-oxo-ent-kaur- 15-en-19-oic acid, as well as two new tricyclic sesquiterpenes, one being the previously reported oxidation product of copaborneol and the second one the 5-oxo derivative of silphiperfol-6-ene. The structures

  摘要 通过对五种 Espeletiopsis 和两种 Coespeletia 物种的研究，除了许多已知化合物外，还提供了两种新的 kaurene 衍生物 19-acetoxy-ent-kaurene 和 17-oxo-ent-kaur-15-en-19-oic acid，以及作为两种新的三环倍半萜烯，一种是之前报道的copaborneol的氧化产物，另一种是silphiperfol-6-ene的5-氧代衍生物。通过核磁共振研究和化学转化阐明了结构。简要讨论了化学分类情况。
• 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.
• Fluorination of Kaurenoic Acid Derivatives by Remote Functionalization
  作者：Josefa Anaya、M. Concepción Grande、Manuel Grande、Ana-Isabel Patino、Pascual Torres

  DOI：10.1055/s-1999-2852

  日期：1999.9

  Kauranoids and related tetracyclic diterpenoids have recently shown an increasing interest because of the discovery of new biological activities that can be modified by the introduction of a fluorine atom. In this article it is described the stereospecific fluorination of the kauranols 6 and 7 by remote functionalization at the "unactivated" C-7 position.

  由于发现了可通过引入一个氟原子而改变生物活性的新化合物，Kauranoids 和相关的四环二萜类化合物最近越来越受到人们的关注。本文介绍了通过在 "未活化 "的 C-7 位进行远程官能化而对贝壳杉醇 6 和 7 进行立体特异性氟化的过程。
• Ent-kauranes and other constituents of three Helianthus species
  作者：W HERZ、P KULANTHAIVEL、K WATANABE

  DOI：10.1016/0031-9422(83)80036-3

  日期：——

  of Helianthus debilis subsp. cucumerifolius, H. occidentalis and H. simulans afforded a variety of known and some unknown ent-kauranoic acids. H. occidentalis gave, in addition, ciliaric acid and a new biogenetically related atisane derivative occidentalic acid. H. simulans gave the heliangolide leptocarpin and the flavone hymenoxin in addition to ent-kauranes. Several of the diterpenoids from these

  Helianthus debilis subsp 的抽象空中部分。cucumerifolius、H. occidentalis 和 H. simulans 提供了多种已知和一些未知的 ent-kauranoic 酸。此外，H. occidentalis 还提供了纤毛酸和一种新的生物遗传学相关的 atisane 衍生物 occidentalic acid。除了 ent-kauranes 之外，H. simulans 还提供 heliangolide leptocarpin 和黄酮 hymenoxin。来自这些物种的几种二萜类化合物抑制了向日葵蛾的幼虫生长。