berkedienoic acid | 1355460-70-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: berkedienoic acid
• 英文别名: (2E,5E)-4-hydroxy-2-propylideneocta-5,7-dienoic acid
• CAS: 1355460-70-6
• 化学式: C₁₁H₁₆O₃
• 分子量: 196.246
• InChiKey: SSSYMZDZKBTBDM-PDTNFJSOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 berkedienoic acid 以 乙醚 为溶剂， 反应 0.08h， 以0.2 mg的产率得到berkedienoic acid methyl ester
  参考文献：
  名称：

  Caspase-1 Inhibitors from an Extremophilic Fungus That Target Specific Leukemia Cell Lines

  摘要：

  Berkeley Pit Lake, Butte, Montana, is a 540 m deep abandoned open-pit copper mine filled with over 140 billion liters of acidic, metal-sulfate-contaminated water. This harsh environment has yielded several microorganisms that produce interesting biologically active compounds. Several polyketide metabolites including the new berkazaphilones A (1) and B (2) and octadienoic acid derivatives berkedienoic acid (13) and berkedienolactone (15), as well as previously reported azaphilone 4, vermistatin (6), dihydrovermistatin (7), penisimplicissin (8), aldehyde 9, and methylparaconic acid (11), were isolated from a culture broth of Penicillium rubrum taken from a depth of 270 m. The structures of these compounds were deduced by interpretation of spectroscopic data. The compounds were isolated either for their inhibition of the signal transduction enzyme caspase-1 or because of their structural similarity to these inhibitors. Selected compounds were further evaluated for their ability to inhibit interleukin-1 beta production by inflammasomes in induced THP-1 cells. Berkazaphilones B (2) and C (4) and vermistatin analogue penisimplicissin (8) exhibited selective activity against leukemia cancer cell lines in tha National Cancer Institute 60 human cell line assay.

  DOI：

  10.1021/np200414c