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Hordenine

$43

  • Brand : BIOFRON

  • Catalogue Number : BF-H2002

  • Specification : 98%

  • CAS number : 539-15-1

  • Formula : C10H15NO

  • Molecular Weight : 165.23

  • PUBCHEM ID : 68313

  • Volume : 20mg

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Catalogue Number

BF-H2002

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

2-8°C

Molecular Weight

165.23

Appearance

White crystal

Botanical Source

Aconitum tanguticum,Senecio scandens

Structure Type

Alkaloids

Category

Standards;Natural Pytochemical;API

SMILES

CN(C)CCC1=CC=C(C=C1)O

Synonyms

4-[2-(Dimethylamino)ethyl]phenol/Cactine/Anhaline/Peyocactine/N,N-dimethyltyramine/Hordenin/Phenol, 4-[2-(dimethylamino)ethyl]-/Hordetin/Hordenine/p-[2-(Dimethylamino)ethyl]phenol/2-(4-Hydroxyphenyl)-N,N-dimethylethylamine (4-(2-Dimethylaminoethyl)phenol/p-Hydroxy-N,N-dimethylphenethylamine/4-(2-(Dimethylamino)ethyl)phenol/Ordenina/Eremursine/Anhalin/Phenol, p-[2-(dimethylamino)ethyl]-/Ordenine/4-Hydroxy-N,N-dimethylphenethylamine/N,N-Dimethyl-p-hydroxyphenethylamine/Anhalin-d6/N,N-dimethyl-2-(4-hydroxyphenyl)ethylamine

IUPAC Name

4-[2-(dimethylamino)ethyl]phenol

Density

1.0±0.1 g/cm3

Solubility

Methanol; DMSO

Flash Point

123.5±21.3 °C

Boiling Point

270.2±23.0 °C at 760 mmHg

Melting Point

InChl

InChl Key

WGK Germany

RID/ADR

HS Code Reference

2935000000

Personal Projective Equipment

Correct Usage

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

Meta Tag

provides coniferyl ferulate(CAS#:539-15-1) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

31161392

Abstract

Proton magnetic resonance-based metabolomics analysis was performed to determine the global metabolite changes in pathogenic bacterium Pseudomonas aeruginosa PAO1 following exposure to quorum sensing (QS) inhibitor hordenine. Pyocyanin inhibition assay confirmed that hordenine exhibited potent QS inhibitory activity. A total of 40 metabolites were assigned by PMR spectra. Hordenine treatment resulted in the destruction of QS system in P. aeruginosa PAO1 by downregulating the expressions of genes involved in QS. The synthesis of antioxidant enzymes was repressed and the oxidative stress was enhanced due to the dysfunctional QS system of P. aeruginosa PAO1. The enhanced oxidative stress induced by the dysfunctional QS system of P. aeruginosa PAO1 altered the membrane components, enhanced membrane permeability, and disturbed energy metabolism, amino acid metabolism, and nucleotide metabolism, and would ultimately attenuate the pathogenicity of P. aeruginosa PAO1. Hordenine may have promising potential for controlling nosocomial pathogens.

KEYWORDS

Hordenine; Metabolomics; Proton magnetic resonance; Pseudomonas aeruginosa; Quorum sensing

Title

Metabolomic analysis of quorum sensing inhibitor hordenine on Pseudomonas aeruginosa.

Author

Zhou JW1,2, Muhammad J3, Sun B2, Yang R2, Wadood A4, Wang JS5, Jia AQ6,7.

Publish date

2019 Aug

PMID

30609368

Abstract

Serratia marcescens NJ01 is a pathogenic bacterium isolated from diseased tomato leaves. Here, we report on the development of a tomato- S. marcescens host-pathogen system as a model to evaluate the effects of hordenine on quorum sensing (QS)-mediated pathogenicity under native conditions. Exposure to hordenine at 25, 50, and 100 μg/mL significantly inhibited the production of acyl-homoserine lactones and the formation of biofilms. Hordenine treatment notably enhanced the susceptibility of the preformed biofilms to ciprofloxacin by reducing the production of extracellular polysaccharides, destroying the architecture of biofilms, and changing the permeability of membranes, as evidenced by the scattered appearance and dominant red fluorescence in the combination-treated biofilms. Furthermore, the addition of hordenine affected the production of virulence factors, influenced the intracellular metabolites, and downregulated the expressions of QS- and biofilm-related genes. The plant infection model indicated that hordenine could significantly attenuate the pathogenicity of S. marcescens NJ01 in tomato plants. Thus, hordenine could act as a potential pesticide or pesticide accelerant in treating crop infections.

KEYWORDS

Serratia marcescens; biofilm; hordenine; quorum sensing; virulence

Title

Inhibition of Quorum Sensing and Virulence in Serratia marcescens by Hordenine.

Author

Zhou JW1,2, Ruan LY2, Chen HJ3, Luo HZ1,2, Jiang H1,2, Wang JS2, Jia AQ1,2.

Publish date

2019 Jan 23

PMID

30409657

Abstract

The phenethylamine alkaloid hordenine, present in germinated barley, was identified recently as a functionally selective dopamine D2 receptor agonist contributing potentially to the rewarding effects of drinking beer. Here, it was shown that the hordenine precursor N-methyltyramine binds with a similar affinity to the dopamine D2 receptor as hordenine (Ki 31.3 µM) showing also selectivity towards the G protein-mediated pathway over the β-arrestin pathway. Using a newly developed UHPLC-ESI-MS/MS method to monitor beer production, we demonstrated that hordenine and N-methyltyramine were released continuously from barley malt during mashing and were stable during fermentation and conditioning. The amounts released from different base malt types were in a similar range but tended to be higher from caramel malts. Hordenine and N-methyltyramine concentrations in 24 types of beer varied between 1.05-6.32 and 0.59-4.61 mg/L, respectively. Thus, the human uptake of the alkaloids during beer consumption is in the low milligram range.

Copyright © 2018 Elsevier Ltd. All rights reserved.

KEYWORDS

Beer; Brewing; Dopamine D2 receptor agonist; Fermentation; Hordenine; Mashing; N-Methyltyramine

Title

Monitoring of the dopamine D2 receptor agonists hordenine and N-methyltyramine during the brewing process and in commercial beer samples.

Author

Sommer T1, Dlugash G2, Hubner H3, Gmeiner P4, Pischetsrieder M5.

Publish date

2019 Mar 15


Description :

Deamination of hordenine by monoamine oxidase and its action on vasa deferentia of the rat. PUMID/DOI:2570842 J Pharm Pharmacol. 1989 Jun;41(6):421-3. The selectivity of the naturally occurring amine, N,N-dimethyltyramine (Hordenine) for monoamine oxidase (MAO) and its action upon isolated vasa deferentia of the rat was investigated. Hordenine was deaminated by rat liver MAO with a Michaelis constant of 479 microM and maximum velocity of 128 nmol (mg protein)-1 h-1 compared with 144 microM and 482 nmol (mg protein)-1 h-1 for tyramine. Studies, with selective irreversible inhibitors of MAO, showed that Hordenine was a highly selective substrate for MAO-B of liver and that it was not deaminated by the MAO-A of intestinal epithelium. In contrast to tyramine, Hordenine did not produce contractions of isolated vasa deferentia. However, 25 microM Hordenine potentiated contractile responses of vasa, from control animals, to submaximal doses of noradrenaline and inhibited responses to tyramine. It did not alter responses, to noradrenaline, of vasa denervated by chronic pretreatment of rats with guanethidine. Therefore, it appears that Hordenine acted as an inhibitor of noradrenaline uptake, in isolated vasa deferentia. These results indicate that dietary-Hordenine is unlikely to be deaminated by intestinal MAO as this is predominantly MAO-A. Consequently, it is likely to be absorbed and could affect the sympathetic nervous system, by virtue of its action as an inhibitor of noradrenaline uptake.