ent-Kauran-19-oic acid-methylester | 89495-19-2

• 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: ent-Kauran-19-oic acid-methylester
• 英文别名: Methyl (-)-kauran-19-oat；dihydrokaurenoic acid methyl ester
• CAS: 89495-19-2
• 化学式: C₂₁H₃₄O₂
• 分子量: 318.5
• InChiKey: BUVSDORPNUVONA-KBWCDIBOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.21
• 重原子数：
  23.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  kaurenoic acid methyl ester 在 palladium 10% on activated carbon 、 氢气 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以37%的产率得到ent-Kauran-19-oic acid-methylester
  参考文献：
  名称：

  Synthesis and induction of apoptosis signaling pathway of ent-kaurane derivatives

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2009.11.064

文献信息

• Methyl and <i>p</i>-Bromobenzyl Esters of Hydrogenated Kaurenoic Acid for Controlling Anthracnose in Common Bean Plants
  作者：Suellen F. Mota、Denilson F. Oliveira、Vladimir C. G. Heleno、Ana Carolina F. Soares、Jacob O. Midiwo、Elaine A. Souza

  DOI：10.1021/acs.jafc.6b05159

  日期：2017.3.1

  Kaurenoic acid derivatives were prepared and submitted to in vitro assays with the fungus Colletotrichum lindemuthianum, which causes anthracnose disease in the common bean. The most active substances were found to be methyl and p-bromobenzylesters, 7 and 9, respectively, of the hydrogenated kaurenoic acid, which presented a minimum inhibitory concentration (MIC) of 0.097 and 0.131 mM, respectively

  制备了月桂酸衍生物，并用引起普通豆炭疽病的真菌Colletotrichum lindemuthianum进行了体外测定。发现活性最高的物质分别是氢化的脲醛酸的甲基和对溴苄基酯，分别为7和9，其最低抑菌浓度（MIC）分别为0.097和0.131 mM，而商用杀真菌剂甲基硫氰酸甲酯（ MT）的MIC为0.143 mM。物质7（1.401 mM）和9（1.886 mM）将普通豆中炭疽病的严重程度降低至统计学上可与MT（2.044 mM）相当的值。根据计算机研究，化合物7和9都是其他生物体产生的酮类固醇异构酶（KSI）酶的抑制剂，其氨基酸序列可在真菌基因组中检测到。这些物质似乎通过抑制其KSI对抗C. lindemuthianum。因此，物质7和9有希望开发新的杀菌剂。