4-hydroxy-indole-3-carbonylnitrile

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 4-hydroxy-indole-3-carbonylnitrile
• 英文别名: 4-Hydroxy-alpha-oxo-1H-indole-3-acetonitrile；4-hydroxy-1H-indole-3-carbonyl cyanide
• 化学式: C₁₀H₆N₂O₂
• 分子量: 186.17
• InChiKey: KVUDODPZCDAFRS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  76.9
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  L-半胱氨酸 、 4-hydroxy-indole-3-carbonylnitrile 以 aq. phosphate buffer 、 水 、 乙腈 为溶剂， 生成 indolokine B4
  参考文献：
  名称：

  Cellular Stress Upregulates Indole Signaling Metabolites in Escherichia coli

  摘要：

  Escherichia coli broadly colonize the intestinal tract of humans and produce a variety of small molecule signals. However, many of these small molecules remain unknown. Here, we describe a family of widely distributed bacterial metabolites termed the "indolokines." In E. coli, the indolokines are upregulated in response to a redox stressor via aspC and tyrB transaminases. Although indolokine 1 represents a previously unreported metabolite, four of the indolokines (2-5) were previously shown to be derived from indole-3-carbonyl nitrile (ICN) in the plant pathogen defense response. We show that the indolokines are produced in a convergent evolutionary manner relative to plants, enhance E coli persister cell formation, outperform ICN protection in an Arabidopsis thaliana-Pseudomonas syringae infection model, trigger a hallmark plant innate immune response, and activate distinct immunological responses in primary human tissues. Our molecular studies link a family of cellular stress-induced metabolites to defensive responses across bacteria, plants, and humans.

  DOI：

  10.1016/j.chembiol.2020.03.003
• 作为产物：
  描述：

  在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 1,4-二氧六环 为溶剂， 以110 mg的产率得到4-hydroxy-indole-3-carbonylnitrile
  参考文献：
  名称：

  Cellular Stress Upregulates Indole Signaling Metabolites in Escherichia coli

  摘要：

  Escherichia coli broadly colonize the intestinal tract of humans and produce a variety of small molecule signals. However, many of these small molecules remain unknown. Here, we describe a family of widely distributed bacterial metabolites termed the "indolokines." In E. coli, the indolokines are upregulated in response to a redox stressor via aspC and tyrB transaminases. Although indolokine 1 represents a previously unreported metabolite, four of the indolokines (2-5) were previously shown to be derived from indole-3-carbonyl nitrile (ICN) in the plant pathogen defense response. We show that the indolokines are produced in a convergent evolutionary manner relative to plants, enhance E coli persister cell formation, outperform ICN protection in an Arabidopsis thaliana-Pseudomonas syringae infection model, trigger a hallmark plant innate immune response, and activate distinct immunological responses in primary human tissues. Our molecular studies link a family of cellular stress-induced metabolites to defensive responses across bacteria, plants, and humans.

  DOI：

  10.1016/j.chembiol.2020.03.003

文献信息

• A new cyanogenic metabolite in Arabidopsis required for inducible pathogen defence
  作者：Jakub Rajniak、Brenden Barco、Nicole K. Clay、Elizabeth S. Sattely

  DOI：10.1038/nature14907

  日期：2015.9

  biosynthetic pathway to 4-hydroxyindole-3-carbonyl nitrile (4-OH-ICN), a previously unknown Arabidopsis metabolite. This metabolite harbours cyanogenic functionality that is unprecedented in plants and exceedingly rare in nature; furthermore, the aryl cyanohydrin intermediate in the 4-OH-ICN pathway reveals a latent capacity for cyanogenic glucoside biosynthesis in Arabidopsis. By expressing 4-OH-ICN

  拟南芥中数以千计的假定生物合成基因没有已知的功能，这表明有许多有助于植物健康的分子尚未被发现。在这些未表征的基因中，最主要的是响应病原体而上调的细胞色素 P450。在这里，我们从单一病原体诱导的 P450（参考文献 5）CYP82C2 开始，并使用非靶向代谢组学和共表达分析的组合来揭示 4-羟基吲哚-3-羰基腈（4-OH-ICN）的完整生物合成途径，一种以前未知的拟南芥代谢物。这种代谢物具有在植物中前所未有且在自然界中极为罕见的生氰功能；此外，4-OH-ICN 途径中的芳基氰醇中间体揭示了拟南芥中生氰糖苷生物合成的潜在能力。通过在酿酒酵母和本氏烟草中表达 4-OH-ICN 生物合成酶，我们在体外和体内重建了完整的途径，并验证了其酶的功能。拟南芥 4-OH-ICN 通路突变体对细菌病原体丁香假单胞菌的易感性增加，与诱导病原体防御中的作用一致。拟南芥一直是研究小分子在植物先天免疫中作用的卓越模型系统。我们的结果揭示了一个不同于经典