N-Hydroxypipecolic acid
(Synonyms: 1-羟基-2-哌啶羧酸,1-Hydroxy-2-piperidinecarboxylic acid; NHP) 目录号 : GC39247
N-Hydroxypipecolic acid (1-Hydroxy-2-piperidinecarboxy acid) 是一种植物代谢物和系统获得性抗性 (SAR) 调节剂，与免疫信号水杨酸协同协调 SAR 的建立。
Cas No.:115819-92-6
Sample solution is provided at 25 µL, 10mM.
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| Cell experiment [1]: | |
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Cell lines |
Wheat (T. aestivum) cultivar |
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Preparation Method |
Wheat (T. aestivum) cultivar Zhongyuan 98-68 was planted in 24-well cell culture plates (one seed per well) in a 25°C incubator. After 3 days, three plates of seedlings were treated with 1 μl of 1 mM N-hydroxypipecolic acid per seedling. The other three were treated with water and used as the control group. The coleoptiles were collected at 1 day after treatment. |
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Reaction Conditions |
1 mM; 25°C,1 day |
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Applications |
The transcriptomes of three N-hydroxypipecolic acid-treated samples were clustered close to each other and were separate from those of the water-treated samples, indicating high reproducibility within the N-hydroxypipecolic acid-treated samples and distinctive global expression between N-hydroxypipecolic acid-treated and water-treated wheat samples. |
| Animal experiment [2]: | |
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Plants models |
leaves |
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Preparation Method |
Infiltration of lower leaves of Col-0 plants with solutions of either 1 mM D9-N-hydroxypipecolic acid or 1 mM N-hydroxypipecolic acid induced the accumulation of unconjugated SA, the SA-β-glucoside (SAG), and the SA glucose ester (SGE) in both the treated and in distant leaves at 24 h after the treatment. |
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Dosage form |
1 mM; 24h |
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Applications |
Leaf-applied N-hydroxypipecolic acid translocates from treated to distant leaves, are partially glycosylated, and induces systemic SA accumulation in an NPR1-independent manner. |
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References: [1]. Zhang ET, et al. Transcriptomic Analysis of Wheat Seedling Responses to the Systemic Acquired Resistance Inducer N-Hydroxypipecolic Acid. Front Microbiol. 2021 Feb 11;12:621336. [2]. Yildiz I, et al. The mobile SAR signal N-hydroxypipecolic acid induces NPR1-dependent transcriptional reprogramming and immune priming. Plant Physiol. 2021 Jul 6;186(3):1679-1705. |
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N-Hydroxypipecolic acid (N-hydroxypipecolic acid), a plant metabolite, also plays a key role in SAR (systemic acquired resistance) and to a lesser extent in basal resistance.[1] N-hydroxypipecolic acid requires basal salicylic acid and components of the salicylic acid signaling pathway to induce systemic acquired resistance genes.[2] N-hydroxypipecolic acid can confer immunity via the salicylic acid receptor NPR1 to reprogram plants at the level of transcription and prime plants for an enhanced defense capacity.[4]
In vitro experiment it shown that treatment of Arabidopsis Col-0 plants with a 1 mM N-hydroxypipecolic acid solution, either applied via the soil or sprayed on the leaf rosette, triggered a strong SAR response in the leaves.[3] In addition, when treatment with N-hydroxypipecolic acid in the individual leaves of Col-0 plants, acquired resistance developed not only in the treated leaves but also in distant, systemic leaves.[5] There is a strong N-hydroxypipecolic acid (1 mM)-mediated priming of the pathogen-triggered accumulation of camalexin. And exogenous N-hydroxypipecolic acid also strongly primed the N-hydroxypipecolic acid-deficient fmo1 mutant for the Psm-triggered accumulation of camalexin. Pretreatment with 1mM N-hydroxypipecolic acid also significantly primed the leaves for an enhanced accumulation of Pip and SA in response to the mock-infiltration, suggesting that N-hydroxypipecolic acid also primes responses to mechanical stress in Arabidopsis.[6]
References:
[1].Hartmann M, Zeier J. N-hydroxypipecolic acid and salicylic acid: a metabolic duo for systemic acquired resistance. Curr Opin Plant Biol. 2019 Aug;50:44-57.
[2].Nair A, et al. N-hydroxypipecolic acid-induced transcription requires the salicylic acid signaling pathway at basal SA levels. Plant Physiol. 2021 Dec 4;187(4):2803-2819.
[3].Schnake A, et al. Inducible biosynthesis and immune function of the systemic acquired resistance inducer N-hydroxypipecolic acid in monocotyledonous and dicotyledonous plants. J Exp Bot. 2020 Oct 22;71(20):6444-6459.
[4].Zeier J. Metabolic regulation of systemic acquired resistance. Curr Opin Plant Biol. 2021 Aug;62:102050.
[5].Chen YC, et al.?N-hydroxy-pipecolic acid is a mobile metabolite that induces systemic disease resistance in?Arabidopsis. Proc Natl Acad Sci U S A. 2018 May 22;115(21):E4920-E4929.
[6].Yildiz I, et al. The mobile SAR signal N-hydroxypipecolic acid induces NPR1-dependent transcriptional reprogramming and immune priming. Plant Physiol. 2021 Jul 6;186(3):1679-1705.
N-Hydroxypipecolic acid (N-hydroxypipecolic acid) 是一种植物代谢产物，在 SAR（系统获得性抗性）中也起着关键作用，并且在较小程度上在基础抗性中起着关键作用。[1] N -羟基哌啶酸需要基础水杨酸和水杨酸信号通路的组分来诱导系统获得性抗性基因。[2] N-羟基哌啶酸可以通过水杨酸受体 NPR1 赋予植物免疫力，从而在转录水平和启动植物以增强防御能力。[4]
体外实验表明，用 1 mM N-羟基哌啶酸溶液处理拟南芥 Col-0 植物，无论是通过土壤施用还是喷洒在叶莲座上，都会在叶子中引发强烈的 SAR 反应。 [3] 此外，当用 N-羟基哌啶酸处理 Col-0 植物的单个叶片时，获得性抗性不仅在处理过的叶片中产生，而且在远处的系统叶片中也产生。[5] 存在强 N-羟基哌啶酸 (1 mM) 介导的病原体触发的 camalexin 积累的启动。外源性 N-羟基哌啶酸也强烈引发了 N-羟基哌啶酸缺陷型 fmo1 突变体，用于 Psm 触发的 camalexin 积累。用 1mM N-羟基哌啶酸预处理也显着引发叶子以增强 Pip 和 SA 的积累以响应模拟浸润，表明 N-羟基哌啶酸也引发拟南芥对机械应力的反应。[6]< /sup>
| Cas No. | 115819-92-6 | SDF | |
| 别名 | 1-羟基-2-哌啶羧酸,1-Hydroxy-2-piperidinecarboxylic acid; NHP | ||
| Canonical SMILES | O=C(C1N(O)CCCC1)O | ||
| 分子式 | C6H11NO3 | 分子量 | 145.16 |
| 溶解度 | DMSO: 83.33 mg/mL (574.06 mM) | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 6.889 mL | 34.4448 mL | 68.8895 mL |
| 5 mM | 1.3778 mL | 6.889 mL | 13.7779 mL |
| 10 mM | 0.6889 mL | 3.4445 mL | 6.889 mL |
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动物平均体重 | g | |
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动物数量 | 只 |
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| % DMSO % % Tween 80 % saline | ||||||||||
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工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
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2.
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Salicylic Acid and N-Hydroxypipecolic acid at the Fulcrum of the Plant Immunity-Growth Equilibrium
Front Plant Sci 2022 Mar 10;13:841688.PMID:35360332DOI:10.3389/fpls.2022.841688.
Salicylic acid (SA) and N-Hydroxypipecolic acid (NHP) are two central plant immune signals involved in both resistance at local sites of pathogen infection (basal resistance) and at distal uninfected sites after primary infection (systemic acquired resistance). Major discoveries and advances have led to deeper understanding of their biosynthesis and signaling during plant defense responses. In addition to their well-defined roles in immunity, recent research is emerging on their direct mechanistic impacts on plant growth and development. In this review, we will first provide an overview of how SA and NHP regulate local and systemic immune responses in plants. We will emphasize how these two signals are mutually potentiated and are convergent on multiple aspects-from biosynthesis to homeostasis, and from signaling to gene expression and phenotypic responses. We will then highlight how SA and NHP are emerging to be crucial regulators of the growth-defense balance, showcasing recent multi-faceted studies on their metabolism, receptor signaling and direct growth/development-related host targets. Overall, this article reflects current advances and provides future outlooks on SA/NHP biology and their functional significance as central signals for plant immunity and growth. Because global climate change will increasingly influence plant health and resilience, it is paramount to fundamentally understand how these two tightly linked plant signals are at the nexus of the growth-defense balance.
l-lysine metabolism to N-Hydroxypipecolic acid: an integral immune-activating pathway in plants
Plant J 2018 Oct;96(1):5-21.PMID:30035374DOI:10.1111/tpj.14037.
l-lysine catabolic routes in plants include the saccharopine pathway to α-aminoadipate and decarboxylation of lysine to cadaverine. The current review will cover a third l-lysine metabolic pathway having a major role in plant systemic acquired resistance (SAR) to pathogen infection that was recently discovered in Arabidopsis thaliana. In this pathway, the aminotransferase AGD2-like defense response protein (ALD1) α-transaminates l-lysine and generates cyclic dehydropipecolic (DP) intermediates that are subsequently reduced to pipecolic acid (Pip) by the reductase SAR-deficient 4 (SARD4). l-pipecolic acid, which occurs ubiquitously in the plant kingdom, is further N-hydroxylated to the systemic acquired resistance (SAR)-activating metabolite N-Hydroxypipecolic acid (NHP) by flavin-dependent monooxygenase1 (FMO1). N-Hydroxypipecolic acid induces the expression of a set of major plant immune genes to enhance defense readiness, amplifies resistance responses, acts synergistically with the defense hormone salicylic acid, promotes the hypersensitive cell death response and primes plants for effective immune mobilization in cases of future pathogen challenge. This pathogen-inducible NHP biosynthetic pathway is activated at the transcriptional level and involves feedback amplification. Apart from FMO1, some cytochrome P450 monooxygenases involved in secondary metabolism catalyze N-hydroxylation reactions in plants. In specific taxa, pipecolic acid might also serve as a precursor in the biosynthesis of specialized natural products, leading to C-hydroxylated and otherwise modified piperidine derivatives, including indolizidine alkaloids. Finally, we show that NHP is glycosylated in Arabidopsis to form a hexose-conjugate, and then discuss open questions in Pip/NHP-related research.
N-Hydroxypipecolic acid and salicylic acid: a metabolic duo for systemic acquired resistance
Curr Opin Plant Biol 2019 Aug;50:44-57.PMID:30927665DOI:10.1016/j.pbi.2019.02.006.
Recent research has established that the pipecolate pathway, a three-step biochemical sequence from l-lysine to N-Hydroxypipecolic acid (NHP), is central for plant systemic acquired resistance (SAR). NHP orchestrates SAR establishment in concert with the immune signal salicylic acid (SA). Here, we outline the biochemistry of NHP formation from l-Lys and address novel progress on SA biosynthesis in Arabidopsis and other plant species. In Arabidopsis, the pathogen-inducible pipecolate and salicylate pathways are activated by common and distinct regulatory elements and mutual interactions between both metabolic branches exist. The mode of action of NHP in SAR involves direct induction of SAR gene expression, signal amplification, priming for enhanced defense activation and positive interplay with SA signaling to ensure elevated plant immunity.
Biosynthesis and Regulation of Salicylic Acid and N-Hydroxypipecolic acid in Plant Immunity
Mol Plant 2020 Jan 6;13(1):31-41.PMID:31863850DOI:10.1016/j.molp.2019.12.008.
Salicylic acid (SA) has long been known to be essential for basal defense and systemic acquired resistance (SAR). N-Hydroxypipecolic acid (NHP), a recently discovered plant metabolite, also plays a key role in SAR and to a lesser extent in basal resistance. Following pathogen infection, levels of both compounds are dramatically increased. Analysis of SA- or SAR-deficient mutants has uncovered how SA and NHP are biosynthesized. The completion of the SA and NHP biosynthetic pathways in Arabidopsis allowed better understanding of how they are regulated. In this review, we discuss recent progress on SA and NHP biosynthesis and their regulation in plant immunity.
N-Hydroxypipecolic acid: a general and conserved activator of systemic plant immunity
J Exp Bot 2020 Oct 22;71(20):6193-6196.PMID:33104213DOI:10.1093/jxb/eraa345.
This article comments on: Schnake A, Hartmann M, Schreiber S, Malik J, Brahmann L, Yildiz I, von Dahlen J, Rose LE, Schaffrath U, Zeier J. 2020. Inducible biosynthesis and immune function of the systemic acquired resistance inducer N-Hydroxypipecolic acid in monocotyledonous and dicotyledonous plants. Journal of Experimental Botany 71, 6444–6459.