N-Hydroxypipecolic acid |
| Catalog No.: GC39247 |
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.
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
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Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
| 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.
| Cas No. | 115819-92-6 | SDF | |
| Canonical SMILES | O=C(C1N(O)CCCC1)O | ||
| Formula | C6H11NO3 | M.Wt | 145.16 |
| Solubility | DMSO: 83.33 mg/mL (574.06 mM) | Storage | Store at -20°C |
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. | ||
| Shipping Condition | Evaluation sample solution : ship with blue ice All other available size: ship with RT , or blue ice upon request |
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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.
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