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N-Hydroxypipecolic acid

カタログ番号GC39247

N-ヒドロキシピペコリン酸 (1-ヒドロキシ-2-ピペリジンカルボン酸) は、植物の代謝産物であり、全身獲得耐性 (SAR) 調節因子であり、免疫シグナルであるサリチル酸と協調して SAR の確立を調整します。

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N-Hydroxypipecolic acid 化学構造

Cas No.: 115819-92-6

サイズ 価格 在庫数 個数
5mg
$98.00
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10mg
$172.00
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50mg
$324.00
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100mg
$417.00
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250mg
$834.00
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Sample solution is provided at 25 µL, 10mM.

Product has been cited by 1 publications

Product Documents

Quality Control & SDS

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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
Canonical SMILES O=C(C1N(O)CCCC1)O
Formula C6H11NO3 M.Wt 145.16
溶解度 DMSO: 83.33 mg/mL (574.06 mM) Storage Store at -20°C
General tips Please select the appropriate solvent to prepare the stock solution according to the solubility of the product in different solvents; once the solution is prepared, please store it in separate packages to avoid product failure caused by repeated freezing and thawing.Storage method and period of the stock solution: When stored at -80°C, please use it within 6 months; when stored at -20°C, please use it within 1 month.
To increase solubility, heat the tube to 37°C and then oscillate in an ultrasonic bath for some time.
Shipping Condition Evaluation sample solution: shipped with blue ice. All other sizes available: with RT, or with Blue Ice upon request.

Complete Stock Solution Preparation Table

Prepare stock solution
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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Average Rating: 5 ★★★★★ (Based on Reviews and 37 reference(s) in Google Scholar.)

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