diacetylterrein | 57800-53-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: diacetylterrein
• 英文别名: Terreindiacetat；(E)-5-oxo-3-(prop-1-enyl)cyclopent-3-ene-1,2-diyl diacetate；[(1S,5R)-5-acetyloxy-4-oxo-2-[(E)-prop-1-enyl]cyclopent-2-en-1-yl] acetate
• CAS: 57800-53-0
• 化学式: C₁₂H₁₄O₅
• 分子量: 238.24
• InChiKey: SJZZHELEKZVTPC-XMXMHJJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  土曲霉酮 、 乙酸酐 在 吡啶 作用下， 生成 diacetylterrein
  参考文献：
  名称：

  来自海洋杂色曲霉的海洋菌株的生物活性代谢物。

  摘要：

  除了已知的霉菌代谢物麦角固醇，terrein，shamixanthone和tajixanthone hydrate外，还从海洋曲霉紫花苜蓿的海洋菌株中鉴定出了曲柄三醇（1），水曲柳（2），二氢terrein（3）和varixanthone（4）。 。1-4的化学结构是通过光谱技术和一些化学转化而建立的。在NCI的60细胞小组中，varitriol（1）对选定的肾脏，CNS和乳腺癌细胞系显示出更高的效力。Varixanthone（4）具有抗菌活性。

  DOI：

  10.1021/np0103214

文献信息

• Bioactive Metabolites from a Marine-Derived Strain of the Fungus <i>Emericella variecolor</i>
  作者：Joan Malmstrøm、Carsten Christophersen、Alejandro F. Barrero、J. Enrique Oltra、José Justicia、Antonio Rosales

  DOI：10.1021/np0103214

  日期：2002.3.1

  From a marine-derived strain of the fungus Emericella variecolor, varitriol (1), varioxirane (2), dihydroterrein (3), and varixanthone (4), besides the known mold metabolites ergosterol, terrein, shamixanthone, and tajixanthone hydrate, were identified. The chemical structures of 1-4 were established by means of spectroscopic techniques and some chemical transformations. In the NCI's 60-cell panel

  除了已知的霉菌代谢物麦角固醇，terrein，shamixanthone和tajixanthone hydrate外，还从海洋曲霉紫花苜蓿的海洋菌株中鉴定出了曲柄三醇（1），水曲柳（2），二氢terrein（3）和varixanthone（4）。 。1-4的化学结构是通过光谱技术和一些化学转化而建立的。在NCI的60细胞小组中，varitriol（1）对选定的肾脏，CNS和乳腺癌细胞系显示出更高的效力。Varixanthone（4）具有抗菌活性。
• US4188329A
  申请人：——

  公开号：US4188329A

  公开（公告）日：1980-02-12
• Studies on terrein as a new class of proteasome inhibitors
  作者：M. Demasi、A. L. Felicio、A. O. Pacheco、H. G. Leite、C. Lima、L. H. Andrade

  DOI：10.1590/s0103-50532010000200015

  日期：——

  The proteasome is an intracellular multicatalytic protease involved in the cell cycle regulation, signaling response, antigen presentation and apoptosis. Since proteasome inhibitors promote cell death by apoptosis, they have been proposed as new anti-tumoral drugs. Terrein, a secondary metabolite secreted by the fungus Aspergillus terreus, was firstly described in 1935. In the present work we report that terrein isolated through the screening for inhibitors of the 20S proteasome showed inhibitory effect upon both chymotrypsin- and trypsin-like activities of the multicatalytic core particle, the 20S proteasome. Despite of the high inhibitory concentration determined in vitro, that verified by incubating cells (fibroblasts and a pulmonary tumor cell line) in the presence of terrein was 4-fold lower indicating the proteasome as a selective intracellular target. Moreover, terrein promoted apoptotic cell death on both fibroblasts and pulmonary tumor cell line tested. Although terrein concentrations (mM range) necessary to elicit apoptosis in the cellular models herein tried were high when compared to those (mu M and nM range) of other inhibitors recently described, its chemical structure is not correlated to any other inhibitor reported thus far. Therefore, the present results point out for the possibility of exploring terrein as a new molecular fragment for the development of synthetic proteasome inhibitors.