Indole-3-pyruvic Acid
(Synonyms: 吲哚-3-丙酮酸) 目录号 : GC47456
An endogenous metabolite of tryptophan
Cas No.:392-12-1
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
Indole-3-pyruvic acid is an endogenous metabolite of tryptophan and intermediate in the biosynthesis of the major auxin hormone, indole-3-acetic acid , in plants.[1][2][3] Indole-3-pyruvic acid (50 and 250 µM) activates the aryl hydrocarbon receptor (AhR) in a reporter assay.[1] It reduces UVB-induced cytotoxicity and the levels of COX-2 in HaCaT keratinocytes.4 Topical administration of indole-3-pyruvic acid (100 µmol) reduces the severity of UVB-induced damage in mouse skin. Dietary administration of indole-3-pyruvic acid (0.1%) reduces diarrhea, colonic inflammation, and the colonic expression of Il1b, Ifng, Tnfa, and Il12b in a mouse model of T cell-mediated colitis.[1] It increases the time spent in the open arms of the elevated plus maze in mice when administered at a dose of 100 mg/kg.[2] It also reverses the anxiogenic effect of caffeine and 3-hydroxy kynurenine, but not pentylenetetrazole or phenylethylamine, in the elevated plus maze in mice.
Reference:
[1].Aoki, R., Aoki-Yoshida, A., Suzuki, C., et al.Indole-3-pyruvic acid, an aryl hydrocarbon receptor activator, suppresses experimental colitis in miceJ. Immunol.201(12)3683-3693(2018)
[2].Lapin, I.P., and Politi, V.Anxiolytic effect of indole-3-pyruvic acid (IPA) in micePharmacol. Res.28(2)129-134(1993)
[3].Mashiguchi, K., Tanaka, K., Sakai, T., et al.The main auxin biosynthesis pathway in ArabidopsisProc. Natl. Acad. Sci. USA108(45)18512-18517(2011)
[4].Aoki, R., Aoki-Yoshida, A., Suzuki, C., et al.Protective effect of indole-3-pyruvate against ultraviolet b-induced damage to cultured HaCaT keratinocytes and the skin of hairless micePLoS One9(5)e96804(2014)
| Cas No. | 392-12-1 | SDF | |
| 别名 | 吲哚-3-丙酮酸 | ||
| 化学名 | α-oxo-1H-indole-3-propanoic acid | ||
| Canonical SMILES | O=C(C(O)=O)CC1=CNC2=CC=CC=C21 | ||
| 分子式 | C11H9NO3 | 分子量 | 203.2 |
| 溶解度 | DMF: 30 mg/ml,DMSO: 30 mg/ml,DMSO:PBS (pH 7.2) (1:6): 0.14 mg/ml | 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 | 4.9213 mL | 24.6063 mL | 49.2126 mL |
| 5 mM | 0.9843 mL | 4.9213 mL | 9.8425 mL |
| 10 mM | 0.4921 mL | 2.4606 mL | 4.9213 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
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，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
The pathway of auxin biosynthesis in plants
J Exp Bot 2012 May;63(8):2853-72.PMID:22447967DOI:10.1093/jxb/ers091.
The plant hormone auxin, which is predominantly represented by indole-3-acetic acid (IAA), is involved in the regulation of plant growth and development. Although IAA was the first plant hormone identified, the biosynthetic pathway at the genetic level has remained unclear. Two major pathways for IAA biosynthesis have been proposed: the tryptophan (Trp)-independent and Trp-dependent pathways. In Trp-dependent IAA biosynthesis, four pathways have been postulated in plants: (i) the indole-3-acetamide (IAM) pathway; (ii) the Indole-3-pyruvic Acid (IPA) pathway; (iii) the tryptamine (TAM) pathway; and (iv) the indole-3-acetaldoxime (IAOX) pathway. Although different plant species may have unique strategies and modifications to optimize their metabolic pathways, plants would be expected to share evolutionarily conserved core mechanisms for auxin biosynthesis because IAA is a fundamental substance in the plant life cycle. In this review, the genes now known to be involved in auxin biosynthesis are summarized and the major IAA biosynthetic pathway distributed widely in the plant kingdom is discussed on the basis of biochemical and molecular biological findings and bioinformatics studies. Based on evolutionarily conserved core mechanisms, it is thought that the pathway via IAM or IPA is the major route(s) to IAA in plants.
Characterization of Indole-3-pyruvic Acid pathway-mediated biosynthesis of auxin in Neurospora crassa
PLoS One 2018 Feb 8;13(2):e0192293.PMID:29420579DOI:10.1371/journal.pone.0192293.
Plants, bacteria and some fungi are known to produce indole-3-acetic acid (IAA) by employing various pathways. Among these pathways, the Indole-3-pyruvic Acid (IPA) pathway is the best studied in green plants and plant-associated beneficial microbes. While IAA production circuitry in plants has been studied for decades, little is known regarding the IAA biosynthesis pathway in fungal species. Here, we present the first data for IAA-producing genes and the associated biosynthesis pathway in a non-pathogenic fungus, Neurospora crassa. For this purpose, we used a computational approach to determine the genes and outlined the IAA production circuitry in N. crassa. We then validated these data with experimental evidence. Here, we describe the homologous genes that are present in the IPA pathway of IAA production in N. crassa. High-performance liquid chromatography and thin-layer chromatography unambiguously identified IAA, indole-3-lactic acid (ILA) and tryptophol (TOL) from cultures supplemented with tryptophan. Deletion of the gene (cfp) that encodes the enzyme indole-3-pyruvate decarboxylase, which converts IPA to indole-3-acetaldehyde (IAAld), results in an accumulation of higher levels of ILA in the N. crassa culture medium. A double knock-out strain (Δcbs-3;Δahd-2) for the enzyme IAAld dehydrogenase, which converts IAAld to IAA, shows a many fold decrease in IAA production compared with the wild type strain. The Δcbs-3;Δahd-2 strain also displays slower conidiation and produces many fewer conidiospores than the wild type strain.
Indole-3-pyruvic Acid regulates TAA1 activity, which plays a key role in coordinating the two steps of auxin biosynthesis
Proc Natl Acad Sci U S A 2022 Jun 21;119(25):e2203633119.PMID:35696560DOI:10.1073/pnas.2203633119.
Auxin biosynthesis involves two types of enzymes: the Trp aminotransferases (TAA/TARs) and the flavin monooxygenases (YUCCAs). This two-step pathway is highly conserved throughout the plant kingdom and is essential for almost all of the major developmental processes. Despite their importance, it is unclear how these enzymes are regulated and how their activities are coordinated. Here, we show that TAA1/TARs are regulated by their product Indole-3-pyruvic Acid (IPyA) (or its mimic KOK2099) via negative feedback regulation in Arabidopsis thaliana. This regulatory system also functions in rice and tomato. This negative feedback regulation appears to be achieved by both the reversibility of Trp aminotransferase activity and the competitive inhibition of TAA1 activity by IPyA. The Km value of IPyA is 0.7 µM, and that of Trp is 43.6 µM; this allows IPyA to be maintained at low levels and prevents unfavorable nonenzymatic indole-3-acetic acid (IAA) formation from IPyA in vivo. Thus, IPyA levels are maintained by the push (by TAA1/TARs) and pull (by YUCCAs) of the two biosynthetic enzymes, in which TAA1 plays a key role in preventing the over- or under-accumulation of IPyA. TAA1 prefer Ala among various amino acid substrates in the reverse reaction of auxin biosynthesis, allowing TAA1 to show specificity for converting Trp and pyruvate to IPyA and Ala, and the reverse reaction.
Indole-3-pyruvic Acid alleviates rheumatoid arthritis via the aryl hydrocarbon receptor pathway
Ann Transl Med 2023 Mar 15;11(5):213.PMID:37007545DOI:10.21037/atm-23-1074.
Background: In previous studies, we found that smoking may participate in the pathogenesis of rheumatoid arthritis (RA) via the aryl hydrocarbon receptor (AhR) pathway. However, when we conducted a subgroup analysis, the expression of AhR and CYP1A1 in healthy people was higher than that in RA patients. We considered that endogenous AhR ligands may exist in vivo that activate AhR to play a protective role. Indole-3-pyruvic Acid (IPA) is a tryptophan (Trp) metabolite produced by the indole pathway and serves as a ligand of AhR. This study aimed to reveal the effect and mechanism of IPA in RA. Methods: A total of 14 patients with RA and 14 healthy volunteers were enrolled. The differential metabolites were screened with liquid chromatography-mass spectrometry (LC-MS) metabolomics technology. We also treated peripheral blood mononuclear cells (PBMCs) with IPA to evaluate the effect on the differentiation of T helper 17 (Th17) cells or regulatory T (Treg) cells. To determine whether IPA can be used to alleviate RA, we administered IPA to rats with collagen-induced arthritis (CIA). Methotrexate was used as a standard drug for CIA. Results: When the dose reached 20 mg/kg/d, the severity of CIA was significantly reduced. In vitro experiments verified that IPA inhibited the differentiation of Th17 cells and promoted the differentiation of Treg cells, but this effect was weakened by CH223191. Conclusions: IPA is a protective factor for RA; it can restore the Th17/Treg cell balance through the AhR pathway, which can alleviate RA.
Indole-3-acetic acid in plant-microbe interactions
Antonie Van Leeuwenhoek 2014 Jul;106(1):85-125.PMID:24445491DOI:10.1007/s10482-013-0095-y.
Indole-3-acetic acid (IAA) is an important phytohormone with the capacity to control plant development in both beneficial and deleterious ways. The ability to synthesize IAA is an attribute that many bacteria including both plant growth-promoters and phytopathogens possess. There are three main pathways through which IAA is synthesized; the Indole-3-pyruvic Acid, indole-3-acetamide and indole-3-acetonitrile pathways. This chapter reviews the factors that effect the production of this phytohormone, the role of IAA in bacterial physiology and in plant-microbe interactions including phytostimulation and phytopathogenesis.