(2-hydroxy-1H-indol-3-yl)acetate

• 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: (2-hydroxy-1H-indol-3-yl)acetate
• 英文别名: 2-(2-hydroxy-1H-indol-3-yl)acetate
• 化学式: C10H8NO3-
• 分子量: 190.17
• InChiKey: CBECDMSAFNHLHY-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  76.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  indole-3-acetate 、 氢(+1)阳离子 、 NADH 、 氧气 生成 (2-hydroxy-1H-indol-3-yl)acetate 、 水 、 nicotinamide adenine dinucleotide
  参考文献：
  名称：

  Utilization of the Plant Hormone Indole-3-Acetic Acid for Growth by Pseudomonas putida Strain 1290

  摘要：

  摘要 我们从植物表面分离出了几种具有分解吲哚-3-乙酸（IAA）能力的细菌。其中一株分离菌株 1290 能够利用 IAA 作为唯一的碳、氮和能量来源。该菌株的 16S rRNA 序列被鉴定为 假单胞菌 .儿茶酚 1,2-二加氧酶的活性在 IAA 生长过程中被诱导，表明儿茶酚是 IAA 分解途径的中间产物。这与观察到的情况一致，即生长在 IAA 上的 P. P. putida 1290 细胞的摄氧量随儿茶酚的添加而增加。不能通过 catR 突变体 P. putida 1290 的 catR 突变体不能以 IAA 为代价生长，这也表明儿茶酚在 IAA 代谢中起着中间作用。除了能破坏 IAA 外，菌株 1290 还能在添加色氨酸的培养基中产生 IAA。在根的伸长试验中 P. putida 菌株 1290 完全消除了外源 IAA 对萝卜根伸长的抑制作用。事实上，将根与 P. putida 1290 和 1 mM 浓度的 IAA 对根的发育有积极影响。在萝卜根的共同接种实验中，菌株 1290 只能部分缓解培养物中过量产生 IAA 的细菌的抑制作用。我们的研究结果表明，菌株 1290 在与植物和植物相关细菌的关系中扮演着 IAA 吸收池或回收器的生物学角色。

  DOI：

  10.1128/aem.71.5.2365-2371.2005

文献信息

• Utilization of the Plant Hormone Indole-3-Acetic Acid for Growth by <i>Pseudomonas putida</i> Strain 1290
  作者：Johan H. J. Leveau、Steven E. Lindow

  DOI：10.1128/aem.71.5.2365-2371.2005

  日期：2005.5

  We have isolated from plant surfaces several bacteria with the ability to catabolize indole-3-acetic acid (IAA). One of them, isolate 1290, was able to utilize IAA as a sole source of carbon, nitrogen, and energy. The strain was identified by its 16S rRNA sequence as Pseudomonas putida . Activity of the enzyme catechol 1,2-dioxygenase was induced during growth on IAA, suggesting that catechol is an intermediate of the IAA catabolic pathway. This was in agreement with the observation that the oxygen uptake by IAA-grown P. putida 1290 cells was elevated in response to the addition of catechol. The inability of a catR mutant of P. putida 1290 to grow at the expense of IAA also suggests a central role for catechol as an intermediate in IAA metabolism. Besides being able to destroy IAA, strain 1290 was also capable of producing IAA in media supplemented with tryptophan. In root elongation assays, P. putida strain 1290 completely abolished the inhibitory effect of exogenous IAA on the elongation of radish roots. In fact, coinoculation of roots with P. putida 1290 and 1 mM concentration of IAA had a positive effect on root development. In coinoculation experiments on radish roots, strain 1290 was only partially able to alleviate the inhibitory effect of bacteria that in culture overproduce IAA. Our findings imply a biological role for strain 1290 as a sink or recycler of IAA in its association with plants and plant-associated bacteria.

  摘要 我们从植物表面分离出了几种具有分解吲哚-3-乙酸（IAA）能力的细菌。其中一株分离菌株 1290 能够利用 IAA 作为唯一的碳、氮和能量来源。该菌株的 16S rRNA 序列被鉴定为 假单胞菌 .儿茶酚 1,2-二加氧酶的活性在 IAA 生长过程中被诱导，表明儿茶酚是 IAA 分解途径的中间产物。这与观察到的情况一致，即生长在 IAA 上的 P. P. putida 1290 细胞的摄氧量随儿茶酚的添加而增加。不能通过 catR 突变体 P. putida 1290 的 catR 突变体不能以 IAA 为代价生长，这也表明儿茶酚在 IAA 代谢中起着中间作用。除了能破坏 IAA 外，菌株 1290 还能在添加色氨酸的培养基中产生 IAA。在根的伸长试验中 P. putida 菌株 1290 完全消除了外源 IAA 对萝卜根伸长的抑制作用。事实上，将根与 P. putida 1290 和 1 mM 浓度的 IAA 对根的发育有积极影响。在萝卜根的共同接种实验中，菌株 1290 只能部分缓解培养物中过量产生 IAA 的细菌的抑制作用。我们的研究结果表明，菌株 1290 在与植物和植物相关细菌的关系中扮演着 IAA 吸收池或回收器的生物学角色。
• Functional Characterization of the Bacterial iac Genes for Degradation of the Plant Hormone Indole-3-Acetic Acid
  作者：Jeness C. Scott、Isaac V. Greenhut、Johan H. J. Leveau

  DOI：10.1007/s10886-013-0324-x

  日期：2013.7

  Pseudomonas putida 1290 is a model organism for the study of bacterial degradation of the plant hormone indole-3-acetic acid (IAA). This property is encoded by the iac gene cluster. Insertional inactivation and/or deletion of individual iac genes and heterologous expression of the gene cluster in Escherichia coli were combined with mass spectrometry to demonstrate that iac-based degradation of IAA is likely to involve 2-hydroxy-IAA, 3-hydroxy-2-oxo-IAA, and catechol as intermediates. The first gene of the cluster, iacA encodes for the first step in the pathway, and also can convert indole to indoxyl to produce the blue pigment indigo. Transcriptional profiling of iac genes in P. putida 1290 revealed that they were induced in the presence of IAA. Based on results with an iacR knockout, we propose that this gene codes for a repressor of iacA expression and that exposure to IAA relieves this repression. Transformation of P. putida KT2440 (which cannot degrade IAA) with the iac gene cluster conferred the ability to grow on IAA as a sole source of carbon and energy, but not the ability to chemotaxi towards IAA. We could show such tactic response for P. putida 1290, thus representing the first demonstration of bacterial chemotaxis towards IAA. We discuss the ecological significance of our findings, and specifically the following question: under what circumstances do bacteria with the ability to degrade, recognize, and move towards IAA have a selective advantage?

  假单胞菌1290是研究植物激素吲哚-3-乙酸（IAA）细菌降解的模型生物。这种特性由iac基因簇编码。通过质谱分析，我们发现，在大肠杆菌中，单个iac基因的插入失活和/或缺失以及基因簇的异源表达表明，基于iac的IAA降解可能涉及2-羟基-IAA、3-羟基-2-氧代-IAA和儿茶酚作为中间产物。基因簇的第一个基因iacA编码该途径的第一步，并且还可以将吲