methyl ent-15-oxokaur-16-en-19-oate | 22376-47-2

• 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: methyl ent-15-oxokaur-16-en-19-oate
• 英文别名: 15-Oxo-(-)-Δ¹⁶-kauren-19-saeure-methylester；ent-15-Oxo-kaur-16-en-19-oic acid methyl ester；methyl (1R,4S,5R,9S,10S,13R)-5,9-dimethyl-14-methylidene-15-oxotetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylate
• CAS: 22376-47-2
• 化学式: C₂₁H₃₀O₃
• 分子量: 330.467
• InChiKey: VGIYQTCUAQAPCL-KLSAVCNVSA-N

物化性质

• 熔点：
  138 °C
• 沸点：
  433.0±34.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.81
• 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：

  methyl ent-15-oxokaur-16-en-19-oate 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 生成 Methyl 15β-hydroxy-ent-kaur-16-en-19-oate
  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
• 作为产物：
  描述：

  Methyl 15β-hydroxy-ent-kaur-16-en-19-oate 在 manganese(IV) oxide 作用下， 以 乙醚 为溶剂， 反应 12.0h， 以15 mg的产率得到methyl ent-15-oxokaur-16-en-19-oate
  参考文献：
  名称：

  来自一枝黄花属的倍半萜烯和二萜衍生物

  摘要：

  摘要 除了已知化合物外，对四种一枝黄花的研究还提供了四种新的石竹烯衍生物、两种桉树油、两种松香烷、一种克罗丹、两种拉丹烷、三种贝壳杉烷和一种当归醇。这些结构是通过光谱方法和一些化学转化来阐明的。虽然分离的二萜广泛存在于一枝黄花属中，但以前从未从任何物种中获得倍半萜。然而，大属的整体情况相对统一。

  DOI：

  10.1016/s0031-9422(00)83939-4

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。
• The biotransformation of ent-15-oxokaur-16-en-19-oic acid and its methyl ester by Cephalosporium aphidicola
  作者：Alaide B. de Oliveira、James R. Hanson、Jacqueline A. Takahashi

  DOI：10.1016/0031-9422(95)00289-j

  日期：1995.9

  ent-15-Oxokaur-16-en-19-oic acid and its methyl ester are transformed to ent-11α,16β-dihydroxy-15-oxokauran-19-oic acid and its methyl ester, respectively, by Cephalosporium aphidicola.

  Cephalosporium aphidicola 将 ent-15-Oxokaur-16-en-19-oic 酸及其甲酯分别转化为 ent-11α,16β-dihydroxy-15-oxokauran-19-oic 酸及其甲酯。
• Selective Oxidations in the Synthesis of Complex Natural <i>ent</i>-Kauranes and <i>ent</i>-Beyeranes
  作者：Victor C. S. Santana、Eduardo C. S. Rocha、Julian C. S. Pavan、Vladimir C. G. Heleno、Emilio C. de Lucca

  DOI：10.1021/acs.joc.2c01051

  日期：2022.8.5

  Syntheses of two natural products derived from the ent-kaurene kaurenoic acid are described for the first time using regio- and diastereoselective oxidations. Palladium- and manganese-mediated oxidations were used to accomplish the syntheses of two ent-beyerane metabolites. The use of the White–Gormisky–Zhao catalyst Mn(CF3-PDP) enabled the first application of a nondirected metal-catalyzed oxidation

  首次使用区域和非对映选择性氧化描述了从对映-贝壳杉烯贝壳酸衍生的两种天然产物的合成。钯和锰介导的氧化用于完成两种 ent-拜亚烷代谢物的合成。White-Gormisky-Zhao 催化剂 Mn(CF 3 -PDP) 的使用使非定向金属催化氧化首次应用于全合成中未活化的 C-H 键。
• The biotransformation of methyl ent-15-oxokaur-16-en-19-oate by Rhizopus stolonifer and Mucor plumbeus
  作者：M Boaventura

  DOI：10.1016/0031-9422(95)00495-s

  日期：1995.12

  Incubation of methyl ent-15-oxokaur-16-en-19-oate with Rhizopus stolonifer and Mucor plumbeus gave methyl ent-7β,11α-dihydroxy-15-oxokauran-19-oate and methyl ent-7β,16β-dihydroxy-15-oxokauran-19-oate, respectively.

  ent-15-oxokaur-16-en-19-oate 与根霉和毛霉菌一起孵育得到 ent-7β,11α-dihydroxy-15-oxokauran-19-oate 和 ent-7β,16β-dihydroxy-15 甲酯-oxokauran-19-oate，分别。
• 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.