psilostachyin | 3533-47-9

• 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: psilostachyin
• 英文别名: psilostachyin A；(3aS,6S,7R,8S,8aR)-8-hydroxy-6,8-dimethyl-3-methylidenespiro[4,5,6,8a-tetrahydro-3aH-cyclohepta[b]furan-7,5'-oxolane]-2,2'-dione
• CAS: 3533-47-9
• 化学式: C₁₅H₂₀O₅
• 分子量: 280.321
• InChiKey: IRPFOXRBPHCCTG-JISBIHODSA-N

物化性质

• 熔点：
  194-195 °C
• 沸点：
  398.5±12.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 psilostachyin 以 甲醇 、 乙醚 为溶剂， 以100%的产率得到
  参考文献：
  名称：

  The stereochemistry of the 1,3-dipolar cycloadditions of diazomethane to pseudoguaianolides

  摘要：

  The 1,3-dipolar cycloaddition of diazomethane to the sesquiterpene lactones, parthenin, coronopilin, and psilostachyin, gave their respective spiropyrazolines with complete chemoselectivity, while the diastere-oselectivity in favour of the (11S)-stereoisomer was 86-98%. Similarly, mexicanin I acetate, helenalin, and helenalin acetate provided the (11R)-diastereoisomer. When helenalin and its acetate were treated with a large excess of diazomethane, they afforded their respective dipyrazolines with 98% diastere-oselectivity in favour of the (2R,3S,11R)-diastereoisomer. All compounds were characterized by their physical and spectroscopic properties and their absolute configuration was established by X-ray diffraction analysis calculating the Flack and Hooft parameters. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2017.01.009
• 作为产物：
  描述：

  冠裸穗豚草素 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 生成 psilostachyin
  参考文献：
  名称：

  Psilostachyin, acetylated pseudoguaianolides and their analogues: Preparation and evaluation of their anti-inflammatory potential

  摘要：

  Naturally occurring acetylated pseudoguaianolides and psilostachyin including their analogues were synthesized. The structure of semi-synthetic psilostachyin was also confirmed by X-ray crystallography. The anti-inflammatory potential of all the derivatives has been evaluated through in vitro expression of TNF-alpha, IL-1 beta and IL-6 in murine neutrophils. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.06.037

文献信息

• Circular dichroism and optical rotatory dispersion of sesquiterpene lactones
  作者：W. Stöcklin、T.G. Waddell、T.A. Geissman

  DOI：10.1016/s0040-4020(01)92818-2

  日期：1970.1

  The CD curves of a large number of sesquiterpene lactones together with a limited number of ORD curves have been measured. A simple correlation between the sign of the Cotton effect (CE) and the stereochemistry of the α-methylene-γ-lactone chromophore can be deduced from the resulting data. In addition the CE of several ketones (both saturated and unsaturated) and pyrazolines are reported.

  已测量了大量倍半萜烯内酯的CD曲线以及有限数量的ORD曲线。棉花效应（CE）的征兆与α-亚甲基-γ-内酯发色团的立体化学之间的简单关联可以从所得数据中推导出来。另外，据报道有几种酮（饱和和不饱和）和吡唑啉的CE。
• Modulation of the G₂Cell Cycle Checkpoint by Sesquiterpene Lactones Psilostachyins A and C Isolated from the Common Ragweed<i>Ambrosia artemisiifolia</i>
  作者：Christopher M. Sturgeon、Kyle Craig、Colleen Brown、Natalie T. Rundle、Raymond J. Andersen、Michel Roberge

  DOI：10.1055/s-2005-873109

  日期：2005.9

  microtubule spindles. However, the compounds did not interfere with microtubule polymerization in vitro. The related sesquiterpene lactones psilostachyin B, paulitin and isopaulitin were also isolated from the same extract but showed no checkpoint inhibition. The identification of the target(s) of psilostachyins A and C may provide further insight into the signalling pathways involved in cell cycle arrest and

  G（2）DNA损伤检查点抑制剂的基于表型细胞的分析用于筛选来自美国国家癌症研究所天然产物储存库的植物提取物。它显示了从豚草常见豚草的甲醇提取物中的活性。分析指导的分馏导致倍半萜内酯psilostachyinsin A和C鉴定为新型检查点抑制剂。消除它们的α，β-不饱和羰基会导致活性降低，这表明这些化合物可以通过迈克尔加成与目标蛋白共价结合。硬皮水飞蓟宾A和C也阻断有丝分裂中的细胞，并导致异常的微管纺锤体的形成。但是，该化合物在体外不干扰微管聚合。相关倍半萜内酯psilostachyin B，从相同提取物中也分离出了花椰菜素和异链脲素，但没有显示检查点抑制作用。对psilostachyinsA和C的靶标的鉴定可以提供对涉及细胞周期停滞和有丝分裂进程的信号传导途径的进一步了解。
• Psilostachyin, acetylated pseudoguaianolides and their analogues: Preparation and evaluation of their anti-inflammatory potential
  作者：Renu Chib、Bhahwal Ali Shah、Naveen Anand、Anjali Pandey、Kamini Kapoor、Sarang Bani、Vivek K. Gupta、Rajnikant、Vijay K. Sethi、Subhash Chandra Taneja

  DOI：10.1016/j.bmcl.2011.06.037

  日期：2011.8

  Naturally occurring acetylated pseudoguaianolides and psilostachyin including their analogues were synthesized. The structure of semi-synthetic psilostachyin was also confirmed by X-ray crystallography. The anti-inflammatory potential of all the derivatives has been evaluated through in vitro expression of TNF-alpha, IL-1 beta and IL-6 in murine neutrophils. (C) 2011 Elsevier Ltd. All rights reserved.
• The stereochemistry of the 1,3-dipolar cycloadditions of diazomethane to pseudoguaianolides
  作者：Adriana Ortiz-León、J. Martín Torres-Valencia、J. Jesús Manríquez-Torres、José G. Alvarado-Rodríguez、Carlos M. Cerda-García-Rojas、Pedro Joseph-Nathan

  DOI：10.1016/j.tetasy.2017.01.009

  日期：2017.2

  The 1,3-dipolar cycloaddition of diazomethane to the sesquiterpene lactones, parthenin, coronopilin, and psilostachyin, gave their respective spiropyrazolines with complete chemoselectivity, while the diastere-oselectivity in favour of the (11S)-stereoisomer was 86-98%. Similarly, mexicanin I acetate, helenalin, and helenalin acetate provided the (11R)-diastereoisomer. When helenalin and its acetate were treated with a large excess of diazomethane, they afforded their respective dipyrazolines with 98% diastere-oselectivity in favour of the (2R,3S,11R)-diastereoisomer. All compounds were characterized by their physical and spectroscopic properties and their absolute configuration was established by X-ray diffraction analysis calculating the Flack and Hooft parameters. (C) 2017 Elsevier Ltd. All rights reserved.