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N-Hydroxypipecolic acid

Catalog No.GC39247

N-Hydroxypipecolic acid Chemical Structure

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.

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5mg
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Sample solution is provided at 25 µL, 10mM.

Quality Control

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Protocol

Cell experiment [1]:

Cell lines

Wheat (T. aestivum) cultivar

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.

Reaction Conditions

1 mM; 25°C,1 day

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]:

Plants models

leaves

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.

Dosage form

1 mM; 24h

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.

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.

Background

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.

Chemical Properties

Cas No. 115819-92-6 SDF
Synonyms N/A
Chemical Name N/A
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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Research Update

Biosynthesis and Regulation of Salicylic Acid and N-Hydroxypipecolic acidin Plant Immunity

Mol Plant2020 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 acidand salicylic acid: a metabolic duo for systemic acquired resistance

Curr Opin Plant Biol2019 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.

l-lysine metabolism to N-Hydroxypipecolic acid: an integral immune-activating pathway in plants

Plant J2018 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 acidinduces 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-induced transcription requires the salicylic acid signaling pathway at basal SA levels

Plant Physiol2021 Dec 4;187(4):2803-2819.PMID: 34890459DOI: 10.1093/plphys/kiab433

Systemic acquired resistance (SAR) is a plant immune response established in uninfected leaves after colonization of local leaves with biotrophic or hemibiotrophic pathogens. The amino acid-derived metabolite N-Hydroxypipecolic acid(NHP) travels from infected to systemic leaves, where it activates salicylic acid (SA) biosynthesis through the isochorismate pathway. The resulting increased SA levels are essential for induction of a large set of SAR marker genes and full SAR establishment. In this study, we show that pharmacological treatment of Arabidopsis thaliana with NHP induces a subset of SAR-related genes even in the SA induction-deficient2 (sid2/isochorismate synthase1) mutant, which is devoid of NHP-induced SA. NHP-mediated induction is abolished in sid2-1 NahG plants, in which basal SA levels are degraded. The SA receptor NON-EXPRESSOR OF PATHOGENESIS-RELATED GENES1 (NPR1) and its interacting TGACG SEQUENCE-SPECIFIC BINDING PROTEIN (TGA) transcription factors are required for the NHP-mediated induction of SAR genes at resting SA levels. Isothermal titration analysis determined a KD of 7.9 ± 0.5 µM for the SA/NPR1 complex, suggesting that basal levels of SA would not bind to NPR1 unless yet unknown potentially NHP-induced processes increase the affinity. Moreover, the nucleocytoplasmic protein PHYTOALEXIN DEFICIENT4 is required for a slight NHP-mediated increase in NPR1 protein levels and NHP-induced expression of SAR-related genes. Our experiments have unraveled that NHP requires basal SA and components of the SA signaling pathway to induce SAR genes. Still, the mechanism of NHP perception remains enigmatic.

N-Hydroxypipecolic acid: a general and conserved activator of systemic plant immunity

J Exp Bot2020 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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