叶含荚蒾宁 C | 74690-89-4

• 物质功能分类: 天然产物 - 萜类
• 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
• 中文名称: 叶含荚蒾宁 C
• 中文别名: 叶含荚宁C；叶含荚宁 C
• 英文名称: vibsanin C
• 英文别名: [(E)-2-[(1S,2S,7S)-5-(hydroxymethyl)-2-methyl-2-(4-methylpent-3-enyl)-6-oxo-7-(2-oxopropyl)cyclohept-4-en-1-yl]ethenyl] 3-methylbut-2-enoate
• CAS: 74690-89-4
• 化学式: C₂₅H₃₆O₅
• 分子量: 416.558
• InChiKey: FUJYXGPHSQJMJL-QQFOBNRMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  30
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  80.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  叶含荚蒾宁 C 在 sodium tetrahydroborate 、 三乙胺 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 异丙醇 为溶剂， 反应 30.67h， 生成
  参考文献：
  名称：

  Synthesis and neurite outgrowth promoting activity of vibsanin B derivatives

  摘要：

  Intramolecular hetero-DA reaction and unexpected retro-aldol like ring opening reaction were performed. As a result, six derivatives with different skeletons of vibsane-type diterpenoids were synthesized from vibsanin B within three steps. Moreover, compounds 2, 3, and 6 enhanced the neurite outgrowth of NGF-mediated PC12 cells. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.04.061
• 作为产物：
  描述：

  vibsanin B 以 甲苯 为溶剂， 反应 36.0h， 以88%的产率得到叶含荚蒾宁 C
  参考文献：
  名称：

  Synthesis and neurite outgrowth promoting activity of vibsanin B derivatives

  摘要：

  Intramolecular hetero-DA reaction and unexpected retro-aldol like ring opening reaction were performed. As a result, six derivatives with different skeletons of vibsane-type diterpenoids were synthesized from vibsanin B within three steps. Moreover, compounds 2, 3, and 6 enhanced the neurite outgrowth of NGF-mediated PC12 cells. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.04.061

文献信息

• Design, synthesis and biological evaluation of a new class of Hsp90 inhibitors vibsanin C derivatives
  作者：Meng Li、Xianlan She、Yufei Ou、Jiangxin Liu、Zaifeng Yuan、Qin-shi Zhao

  DOI：10.1016/j.ejmech.2022.114844

  日期：2022.12

  diseases. Here, on the basis of primary structure-activity relationships and docking analysis, a series of novel vibsanin C analogues with an emphasis on the C18 position was first designed, synthesized and biologically evaluated. The most effective Hsp90 inhibitory activity among these analogues was demonstrated by 29 and 31, with IC50 values of 0.39 and 0.27 μM respectively. Direct interaction between

  Hsp90 是一种 ATP 依赖性伴侣蛋白，对广泛的蛋白质组装和折叠过程至关重要，长期以来一直被认为是癌症的潜在靶标。Hsp90 最近被确定为在病毒感染、神经退行性疾病和炎症中具有重要的致病作用，因此，开发抑制伴侣蛋白的药物可能会治疗此类顽固性疾病。在这里，在一级构效关系和对接分析的基础上，首先设计、合成和生物学评估了一系列以 C18 位置为重点的新型 vibsanin C 类似物。29和31证明了这些类似物中最有效的 Hsp90 抑制活性，IC为 50值分别为 0.39 和 0.27 μM。进一步证实了 Hsp90 与其抑制剂之间的直接相互作用。机制研究表明，29通过线粒体介导的细胞凋亡途径促进HL-60细胞凋亡。此外，29在 H22 荷瘤小鼠模型中抑制了肿瘤生长，并在小鼠中显示出低急性毒性（LD 50  > 500 mg/kg），表明其具有进一步研究的潜力。
• Structures of New Seven-Membered Ring Vibsane-Type Diterpenes Isolated from Leaves of Viburnum awabuki.
  作者：Hiroyuki MINAMI、Sayoko ANZAKI、Miwa KUBO、Mitsuaki KODAMA、Kazuyoshi KAWAZU、Yoshiyasu FUKUYAMA

  DOI：10.1248/cpb.46.1194

  日期：——

  Five new vibsane-type diterpenes, vibsanin G, vibsanin H, vibsanin K, 18-O-methylvibsanin K and 15, 18-di-O-methylvibsanin H were isoalted from the leaves of Viburnum awabuki (Caplifoliaceae). Their structures were elucidated by analyses of spectroscopic data involving comparison of their 13C-NMR data with those of the previously known vibsanin C, and the structure of vibsanins H and K were confirmed by X-ray crystallographic analysis and chemcial transformation, respectively. All five new compounds differ from the seven-membered ring vibsane-type diterpene, vibsanin C, only in the C-12-C-17 side chain.

  从荚蒾（荚蒾科）的叶中分离出五种新的荚蒾烷型二萜类化合物，分别是荚蒾素 G、荚蒾素 H、荚蒾素 K、18-O-甲基荚蒾素 K 和 15, 18-二-O-甲基荚蒾素 H。通过光谱数据分析阐明了它们的结构，包括将它们的 13C-NMR 数据与先前已知的荚蒾素 C 进行比较，并通过 X 射线晶体学分析和化学转化分别证实了荚蒾素 H 和 K 的结构。这五种新化合物与七元环荚蒾烷型二萜类化合物荚蒾素 C 仅在 C-12-C-17 侧链上有所不同。
• Absolute structure of vibsanins B and C, and their chemical correlation
  作者：Yoshiyasu Fukuyama、Hiroyuki Minami、Shigeru Takaoka、Mitsuaki Kodama、Kazuyoshi Kawazu、Hisao Nemoto

  DOI：10.1016/s0040-4039(97)00041-5

  日期：1997.2

  The absolute structure of vibsanin C, a novel 7-membered vibsane-type diterpene isolated from the leaves of Viburnum awabuki, has been established by X-ray crystallographic analysis of its derivative. Vibsanin C has been proved to be one of Cope rearranged products from vibsanin B, a 11-membered vibsane-type diterpene. (C) 1997 Elsevier Science Ltd.
• Chemical Conversion of Vibsanin C to Vibsanin E and Structure of 3-Hydroxyvibsanin E from <i>Viburnum awabuki</i>
  作者：Yoshiyasu Fukuyama、Hiroyuki Minami、Masami Kagawa、Mitsuaki Kodama、Kazuyoshi Kawazu

  DOI：10.1021/np980338v

  日期：1999.2.1

  Vibsanin E (4), a tricyclic vibsane-type diterpene, has been prepared in 50% yield from vibsanin C (2), a seven-membered ring vibsane-type diterpene by reaction with BF3. OEt2 at -78 degrees C. This chemical correlation not only established structure, including absolute configurations, but also has demonstrated a possible biosynthetic route to 4 via 2 derived from vibsanin B (1). The structure of 3-hydroxyvibsanin E (5), another example of a tricyclic seven-membered ring vibsane, isolated from the leaves of Viburnum awabuki, has been established by extensive analyses of 2D NMR data and comparison of its spectral data with those of 4.
• Synthesis and neurite outgrowth promoting activity of vibsanin B derivatives
  作者：Li-Dong Shao、Jun Xu、Xiu Gao、Juan He、Yu Zhao、Li-Yan Peng、Huai-Rong Luo、Chengfeng Xia、Qin-Shi Zhao

  DOI：10.1016/j.tetlet.2014.04.061

  日期：2014.6

  Intramolecular hetero-DA reaction and unexpected retro-aldol like ring opening reaction were performed. As a result, six derivatives with different skeletons of vibsane-type diterpenoids were synthesized from vibsanin B within three steps. Moreover, compounds 2, 3, and 6 enhanced the neurite outgrowth of NGF-mediated PC12 cells. (C) 2014 Elsevier Ltd. All rights reserved.