{(1R,2R)-3-oxo-2-[(2Z)-pent-2-en-1-yl]cyclopentyl}acetate

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: {(1R,2R)-3-oxo-2-[(2Z)-pent-2-en-1-yl]cyclopentyl}acetate
• 英文别名: 2-[(1R,2R)-3-oxo-2-[(Z)-pent-2-enyl]cyclopentyl]acetate
• 化学式: C12H17O3-
• 分子量: 209.26
• InChiKey: ZNJFBWYDHIGLCU-HWKXXFMVSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  57.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  {(1R,2R)-3-oxo-2-[(2Z)-pent-2-en-1-yl]cyclopentyl}acetate 、 S-腺苷蛋氨酸 生成 茉莉酸甲酯 、 S-(5'-腺苷)-L-高半胱氨酸
  参考文献：
  名称：

  Jasmonic acid carboxyl methyltransferase: A key enzyme for jasmonate-regulated plant responses

  摘要：

  甲基茉莉酸是一种植物挥发性物质，作为重要的细胞调节剂介导多种发育过程和防御反应。我们克隆了新的基因JMT，编码一个S-腺苷-L-甲硫氨酸：茉莉酸羧甲基转移酶（JMT），从拟南芥中。在大肠杆菌中表达的重组JMT蛋白催化茉莉酸形成甲基茉莉酸，Km值为38.5μM。JMT RNA在幼苗中未检测到，但在叶轮、茎叶和发育中的花中检测到。此外，基因的表达在受伤或甲基茉莉酸处理时在局部和系统上都被诱导。这个结果表明，JMT可以感知和响应由外部刺激产生的局部和系统信号，这些信号可能包括甲基茉莉酸本身。转基因拟南芥过表达JMT，内源性甲基茉莉酸水平增加3倍，而茉莉酸含量不变。转基因植物表现出茉莉酸响应基因的组成表达，包括VSP和PDF1.2。此外，转基因植物显示出对致病真菌灰霉菌的增强抗性水平。因此，我们的数据表明，茉莉酸羧甲基转移酶是茉莉酸调节植物反应的关键酶。激活JMT表达会产生甲基茉莉酸，它可以作为细胞内调节剂、可扩散的细胞间信号传递物和空气传递的信号介导植物内部和植物间的通信。

  DOI：

  10.1073/pnas.081557298
• 作为产物：
  描述：

  水 、 茉莉酸甲酯 生成 氢(+1)阳离子 、 {(1R,2R)-3-oxo-2-[(2Z)-pent-2-en-1-yl]cyclopentyl}acetate 、 甲醇
  参考文献：
  名称：

  无活性的甲基吲哚-3-乙酸酯可以被拟南芥 AtMES 酯酶家族的几种酯酶水解和激活。

  摘要：

  植物激素生长素（吲哚-3-乙酸 [IAA]）被发现既游离又与多种碳水化合物、氨基酸和肽结合。我们最近表明 IAA 可以通过拟南芥（拟南芥）酶 IAA 羧基甲基转移酶 1 转化为其甲酯（MeIAA）。然而，MeIAA 在体内的存在和功能仍不清楚。最近，已经表明烟草（烟草）蛋白 SABP2（水杨酸结合蛋白 2）将水杨酸甲酯水解为水杨酸。拟南芥基因组中有 20 个 SABP2 同源物，我们将其命名为 AtMES（甲基酯酶）。我们用各种底物在生化分析中测试了这些基因编码的 15 种蛋白质，并鉴定了几种可以水解 MeIAA 的候选 MeIAA 酯酶。MeIAA，就像 IAA，当外源施用时，对野生型根的生长施加抑制活性。然而，与野生型根相比，在推定的 MeIAA 酯酶基因 AtMES17 (At3g10870) 中携带 T-DNA 插入的拟南芥植物的根对 MeIAA 的敏感性显着降低，同时对游离 IAA

  DOI：

  10.1104/pp.108.118224

文献信息

• A fungal monooxygenase-derived jasmonate attenuates host innate immunity
  作者：Rajesh N Patkar、Peter I Benke、Ziwei Qu、Yuan Yi Constance Chen、Fan Yang、Sanjay Swarup、Naweed I Naqvi

  DOI：10.1038/nchembio.1885

  日期：2015.9

  prevents induction of JA signaling, plant defense or both. However, biosynthesis of 12OH-JA has remained elusive. We report here an antibiotic biosynthesis monooxygenase (Abm) that converts endogenous free JA into 12OH-JA in the model rice blast fungus Magnaporthe oryzae. Such fungal 12OH-JA is secreted during host penetration and helps evade the defense response. Loss of Abm in M. oryzae led to accumulation

  不同的修饰可以微调茉莉酸（JA）在调节植物生长和免疫力方面的活性。羟化JA（12OH-JA）促进花和块茎发育，但阻止JA信号传导，植物防御或两者的诱导。然而，12OH-JA的生物合成仍然难以捉摸。我们在这里报告了一种抗生素生物合成单加氧酶（Abm），它将模型稻瘟病菌Magnaporthe oryzae中的内源性游离JA转化为12OH-JA 。这种真菌12OH-JA在宿主穿透期间会分泌出来，有助于逃避防御反应。米曲霉Abm的损失导致甲基JA（MeJA）的积累，这会诱导宿主防御并阻止侵袭性生长。外源添加的12OH-JA明显减弱了abmΔ诱导的水稻免疫力。值得注意的是，Abm本身是在入侵后分泌的，很可能将植物JA转化为12OH-JA以促进宿主定殖。这项研究揭示了植物与病原体相互作用期间的化学军备竞赛，揭示了Abm作为抗真菌靶标，并概述了转化通用小分子植物激素的合成策略。
• <i>Arabidopsis</i> JASMONATE-INDUCED OXYGENASES down-regulate plant immunity by hydroxylation and inactivation of the hormone jasmonic acid
  作者：Lotte Caarls、Joyce Elberse、Mo Awwanah、Nora R. Ludwig、Michel de Vries、Tieme Zeilmaker、Saskia C. M. Van Wees、Robert C. Schuurink、Guido Van den Ackerveken

  DOI：10.1073/pnas.1701101114

  日期：2017.6.13

  In plants the hormone jasmonic acid (JA) is synthesized in response to attack by pathogens and herbivores, leading to activation of defense responses. Rapidly following JA accumulation the hormone is metabolized, presumably to prevent inhibitive effects of high JA levels on growth and development. The enzymes that directly inactivate JA were so far unknown. Here, we identify four jasmonate-induced oxygenases (JOXs) in Arabidopsis that hydroxylate jasmonic acid to form inactive 12-OH-JA. A mutant that no longer produces the four enzymes hyperaccumulates JA, exhibits reduced growth, and is highly resistant to attackers that are sensitive to JA-dependent defense. The JOX enzymes thus play an important role in determining the amplitude and duration of JA responses to balance the growth–defense trade-off.

  在植物中，激素茉莉酸（JA）会在受到病原体和食草动物攻击时合成，导致防御反应的激活。在JA积累后，该激素快速代谢，可能是为了防止高JA水平对生长和发育的抑制作用。直接失活JA的酶至今尚未被发现。在这里，我们在拟南芥中鉴定了四种茉莉酸诱导的氧化酶（JOXs），它们使茉莉酸羟基化形成无活性的12-OH-JA。不再产生这四种酶的突变体，会高度积累JA，表现出生长减缓，并对对JA依赖性防御敏感的攻击者高度抵抗。因此，JOX酶在平衡生长-防御权衡中起着重要作用，决定JA反应的振幅和持续时间。

• Structure-guided analysis of Arabidopsis JASMONATE-INDUCED OXYGENASE (JOX) 2 reveals key residues for recognition of jasmonic acid substrate by plant JOXs
  作者：Xin Zhang、Dongli Wang、Joyce Elberse、Linlu Qi、Wei Shi、You-Liang Peng、Robert C. Schuurink、Guido Van den Ackerveken、Junfeng Liu

  DOI：10.1016/j.molp.2021.01.017

  日期：2021.5

  The jasmonic acid (JA) signaling pathway is used by plants to control wound responses. The persistent accumulation of JA inhibits plant growth, and the hydroxylation of JA to 12-hydroxy-JA by JASMONATE-INDUCED OXYGENASEs (JOXs, also named jasmonic acid oxidases) is therefore vital for plant growth, while structural details of JA recognition by JOXs are unknown. Here, we present the 2.65 Å resolution

  茉莉酸 (JA) 信号通路被植物用来控制伤口反应。JA 的持续积累抑制植物生长，因此由 JASMONATE-INDUCED OXYGENASEs（JOXs，也称为茉莉酸氧化酶）将 JA 羟基化为 12-羟基-JA 对植物生长至关重要，而 JOXs 识别 JA 的结构细节是未知。在这里，我们展示了拟南芥的 2.65 Å 分辨率 X 射线晶体结构JOX2 与其底物 JA 及其共底物 2-酮戊二酸和 Fe(II) 形成复合物。JOX2 包含一个扭曲的双链 β 螺旋 (DSBH) 核心，两侧是 α 螺旋和环。JA 通过与精氨酸三联体 R225、R350 和 R354 的氢键以及主要与苯丙氨酸三联体 F157、F317 和 F346 的疏水相互作用结合在狭窄的底物袋中。JA 结合最关键的残基是 F157 和 R225，它们都来自 DSBH 核心，它们与 JA 的环戊烷环相互作用。JA 结合的关键残基的空间分布和底物结合袋的形状共同定义了
• VvMJE1 of the grapevine (Vitis vinifera) VvMES methylesterase family encodes for methyl jasmonate esterase and has a role in stress response
  作者：Nan Zhao、Hong Lin、Suque Lan、Qidong Jia、Xinlu Chen、Hong Guo、Feng Chen

  DOI：10.1016/j.plaphy.2016.02.027

  日期：2016.5

  The known members of plant methyl esterase (MES) family catalyze the hydrolysis of a C-O ester linkage of methyl esters of several phytohormones including indole-3-acetic acid, salicylic acid and jasmonic acid. The genome of grapevine (Vitis vinifera) was found to contain 15 MES genes, designated VvMES1-15. In this report, VvMES5 was selected for molecular, biochemical and structural studies. VvMES5 is most similar to tomato methyl jasmonate esterase. E. coli-expressed recombinant VvMES5 displayed methyl jasmonate (MeJA) esterase activity, it was renamed VvMJE1. Under steady-state conditions, VvMJE1 exhibited an apparent Km value of 92.9 mu M with MeJA. VvMJE1 was also shown to have lower activity with methyl salicylate (MeSA), another known substrate of the MES family, and only at high concentrations of the substrate. To understand the structural basis of VvMJE1 in discriminating MeJA and MeSA, a homolog model of VvMJE1 was made using the X-ray structure of tobacco SABP2, which encodes for methyl salicylate esterase, as a template. Interestingly, two bulky residues at the binding site and near the surface of tobacco SABP2 are replaced by relatively small residues in VvMJE1. Such a change enables the accommodation of a larger substrate MeJA in VvMJE1. The expression of VvMJE1 was compared in control grape plants and grape plants treated with one of the three stresses: heat, cold and UV-B. While the expression of VvMJE1 was not affected by heat treatment, its expression was significantly up regulated by cold treatment and UV-B treatment. This result suggests that VvMJE1 has a role in response of grape plants to these two abiotic stresses. (C) 2016 Elsevier Masson SAS. All rights reserved.
• Jasmonic Acid Oxidase 2 Hydroxylates Jasmonic Acid and Represses Basal Defense and Resistance Responses against Botrytis cinerea Infection
  作者：Ekaterina Smirnova、Valentin Marquis、Laure Poirier、Yann Aubert、Julie Zumsteg、Rozenn Ménard、Laurence Miesch、Thierry Heitz

  DOI：10.1016/j.molp.2017.07.010

  日期：2017.9

  Jasmonates (JAs) orchestrate immune responses upon wound/herbivore injury or infection by necrotrophic pathogens. Elucidation of catabolic routes has revealed new complexity in jasmonate metabolism. Two integrated pathways attenuate signaling by turning over the active hormone jasmonoyl-isoleucine (JA-Ile) through omega-oxidation or deconjugation, and define an indirect route forming the derivative 12OH-JA. Here, we provide evidence for a second 12OH-JA formation pathway by direct jasmonic acid (JA) oxidation. Three jasmonic acid oxidases (JAOs) of the 2-oxoglutarate dioxygenase family catalyze specific oxidation of JA to 12OH-JA, and their genes are induced by wounding or infection by the fungus Botrytis cinerea. JAO2 exhibits the highest basal expression, and its deficiency in jao2 mutants strongly enhanced antifungal resistance. The resistance phenotype resulted from constitutive expression of antimicrobial markers rather than from their higher induction in infected jao2 plants and could be reversed by ectopic expression of any of the three JAOs in jao2. Elevated defense in jao2 was dependent on the activity of JASMONATE RESPONSE 1 (JAR1) and CORONATINE-INSENSITIVE 1 (COI1) but was not correlated with enhanced JA-Ile accumulation. Instead, jao2 mutant lines displayed altered accumulation of several JA species in healthy and challenged plants, suggesting elevated metabolic flux through JA-Ile. Collectively, these data identify the missing enzymes hydroxylating JA and uncover an important metabolic diversion mechanism for repressing basal JA defense responses.