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Indole-3-carboxylic acid

$96

  • Brand : BIOFRON

  • Catalogue Number : BN-O1481

  • Specification : 98%(HPLC)

  • CAS number : 771-50-6

  • Formula : C9H7NO2

  • Molecular Weight : 161.2

  • PUBCHEM ID : 69867

  • Volume : 5g

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Catalogue Number

BN-O1481

Analysis Method

Specification

98%(HPLC)

Storage

-20℃

Molecular Weight

161.2

Appearance

Powder

Botanical Source

This product is isolated and purified from the roots of Carpesium abrotanoides

Structure Type

Category

SMILES

C1=CC=C2C(=C1)C(=CN2)C(=O)O

Synonyms

3-Indolylcarboxylic acid/Indole-3-carboxylic acid/Indole-3-carboxylicacid/1H-Indole-3-carboxylic acid/Indole-3-carboxylic_acid/3-Indoleformic acid/3-Indolecarboxylic acid

IUPAC Name

Density

1.4±0.1 g/cm3

Solubility

Flash Point

207.6±21.2 °C

Boiling Point

419.6±18.0 °C at 760 mmHg

Melting Point

232-234 °C (dec.)(lit.)

InChl

InChl Key

KMAKOBLIOCQGJP-UHFFFAOYSA-N

WGK Germany

RID/ADR

HS Code Reference

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:771-50-6) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

No Technical Documents Available For This Product.

PMID

30036059

Abstract

Studies on indole-3-carboxylic acid derivatives as direct activators of human adenosine monophosphate-activated protein kinase (AMPK) α1β1γ1 isoform have culminated in the identification of PF-06409577 (1), PF-06885249 (2), and PF-06679142 (3) as potential clinical candidates. Compounds 1-3 are primarily cleared in animals and humans via glucuronidation. Herein, we describe the biosynthetic preparation, purification, and structural characterization of the glucuronide conjugates of 1-3. Spectral characterization of the purified glucuronides M1, M2, and M3 indicated that they were acyl glucuronide derivatives. In vitro pharmacological evaluation revealed that all three acyl glucuronides retained selective activation of β1-containing AMPK isoforms. Inhibition of de novo lipogenesis with representative parent carboxylic acids and their respective acyl glucuronide conjugates in human hepatocytes demonstrated their propensity to activate cellular AMPK. Cocrystallization of the AMPK α1β1γ1 isoform with 1-3 and M1-M3 provided molecular insights into the structural basis for AMPK activation by the glucuronide conjugates.

Title

Acyl Glucuronide Metabolites of 6-Chloro-5-[4-(1-hydroxycyclobutyl)phenyl]-1 H-indole-3-carboxylic Acid (PF-06409577) and Related Indole-3-carboxylic Acid Derivatives Are Direct Activators of Adenosine Monophosphate-Activated Protein Kinase (AMPK)

Author

Tim F Ryder 1, Matthew F Calabrese 1, Gregory S Walker 1, Kimberly O Cameron, Allan R Reyes, Kris A Borzilleri 1, Jake Delmore, Russell Miller, Ravi G Kurumbail 1, Jessica Ward, Daniel W Kung 1, Janice A Brown 1, David J Edmonds, Heather Eng 1, Angela C Wolford 1, Amit S Kalgutkar

Publish date

2018 Aug 23

PMID

30051514

Abstract

A fast callose accumulation has been shown to mediate defence priming in certain plant-pathogen interactions, but the events upstream of callose assembly following chemical priming are poorly understood, mainly because those steps comprise sugar transfer to the infection site. β-Amino butyric acid (BABA)-induced resistance in Arabidopsis against Plectosphaerella cucumerina is known to be mediated by callose priming. Indole-3-carboxylic acid (ICOOH, also known as I3CA) mediates BABA-induced resistance in Arabidopsis against P. cucumerina. This indolic compound is found in a common fingerprint of primed metabolites following treatments with various priming stimuli. In the present study, we show that I3CA induces resistance in Arabidopsis against P. cucumerina and primes enhancement of callose accumulation. I3CA treatment increased abscisic acid (ABA) levels before infection with P. cucumerina. An intact ABA synthesis pathway is needed to activate a starch amylase (BAM1) to trigger augmented callose deposition against P. cucumerina during I3CA-IR. To verify the relevance of the BAM1 amylase in I3CA-IR, knockdown mutants and overexpressors of the BAM1 gene were tested. The mutant bam1 was impaired to express I3CA-IR, but complemented 35S::BAM1-YFP lines in the background of bam1 restored an intact I3CA-IR and callose priming. Therefore, a more active starch metabolism is a committed step for I3CA-IR, inducing callose priming in adult plants. Additionally, I3CA treatments induced expression of the ubiquitin ligase ATL31 and syntaxin SYP131, suggesting that vesicular trafficking is relevant for callose priming. As a final element in the callose priming, an intact Powdery Mildew resistant4 (PMR4) gene is also essential to fully express I3CA-IR.

KEYWORDS

Plectosphaerella cucumerina; BAM1; callose accumulation; defence priming; indole-3-carboxylic acid.

Title

Starch Degradation, Abscisic Acid and Vesicular Trafficking Are Important Elements in Callose Priming by indole-3-carboxylic Acid in Response to Plectosphaerella Cucumerina Infection

Author

Jordi Gamir 1, Victoria Pastor 2, Paloma Sanchez-Bel 2, Blas Agut 2, Diego Mateu 2, Javier Garcia-Andrade 3, Victor Flors 2

Publish date

2018 Nov;

PMID

29281919

Abstract

Terretonin M (1), a new highly oxygenated tetracyclic meroterpenoid, was isolated from the thermophilic fungus Aspergillus terreus TM8 together with 10 known metabolites: terrelumamide A, asterrelenin, 7-prenyl-indolyl-3-carbaldehyde, (3β,5α,6β)-3,5,6-trihydroxy-ergosta-7,22-diene, sitostenone, linoleic acid, ergosterol, uracil, p-hydroxy-benzoic acid, and indole-3-carboxylic acid. The chemical structure of the new compound was elucidated by extensive 1D, 2D NMR, and ESI HR mass measurements, and by comparison with literature data. The absolute configuration of 1 was resolved by analysis of its NOESY spectrum and comparison of its experimental ECD spectrum with DFT calculations. In parallel to this work, revision of the absolute configuration of penisimplicins 3a and 3b is proposed on the basis of their ECD and ORD data. The isolation and taxonomic characterisation of A. terreus TM8 is reported, and the antimicrobial activity of the crude extract and the isolated compounds was studied as well.

KEYWORDS

Aspergillus terreus TM8; Terretonin M; antimicrobial activity; penisimplicins; taxonomy.

Title

Terretonin M: A New Meroterpenoid From the Thermophilic Aspergillus Terreus TM8 and Revision of the Absolute Configuration of Penisimplicins

Author

Mohamed Shaaban 1 2, Mohammad Magdy El-Metwally 3, Ahmed Adel Abdel-Razek 4, Hartmut Laatsch 2

Publish date

2018 Oct


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