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Desmethoxyyangonin

$300

  • Brand : BIOFRON

  • Catalogue Number : BF-D4013

  • Specification : 98%(HPLC)

  • CAS number : 15345-89-8

  • Formula : C14H12O3

  • Molecular Weight : 228.25

  • PUBCHEM ID : 5273621

  • Volume : 25mg

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Catalogue Number

BF-D4013

Analysis Method

HPLC,NMR,MS

Specification

98%(HPLC)

Storage

-20℃

Molecular Weight

228.25

Appearance

White crystalline powder

Botanical Source

Piper methysticum

Structure Type

Phenylpropanoids

Category

Standards;Natural Pytochemical;API

SMILES

COC1=CC(=O)OC(=C1)C=CC2=CC=CC=C2

Synonyms

DIHYDROKAVAIN/2H-Pyran-2-one, 4-methoxy-6-(2-phenylethenyl)-/2H-Pyran-2-one, 4-methoxy-6-[(E)-2-phenylethenyl]-/4-Methoxy-6-[(E)-2-phenylvinyl]-2H-pyran-2-one/4-methoxy-6-[(E)-2-phenylethenyl]-2H-pyran-2-one/Desmethoxyyangonin/(E)-4-Methoxy-6-(2-phenylethenyl)-2H-pyran-2-one,5,6-Dehydrokavain,Demethoxyyangonin

IUPAC Name

4-methoxy-6-[(E)-2-phenylethenyl]pyran-2-one

Density

1.2±0.1 g/cm3

Solubility

Methanol; Chloroform

Flash Point

188.0±23.3 °C

Boiling Point

440.0±45.0 °C at 760 mmHg

Melting Point

138-140ºC

InChl

InChI=1S/C14H12O3/c1-16-13-9-12(17-14(15)10-13)8-7-11-5-3-2-4-6-11/h2-10H,1H3/b8-7+

InChl Key

DKKJNZYHGRUXBS-BQYQJAHWSA-N

WGK Germany

RID/ADR

HS Code Reference

2932200000

Personal Projective Equipment

Correct Usage

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

Meta Tag

provides coniferyl ferulate(CAS#:15345-89-8) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

29138643

Abstract

Renealmia alpinia (Zingiberaceae), a medicinal plant of tropical rainforests, is used to treat snakebites and other injuries and also as a febrifuge, analgesic, antiemetic, antiulcer, and anticonvulsant. The dichloromethane extract of R. alpinia leaves showed potent inhibition of human monoamine oxidases- (MAOs-) A and B. Phytochemical studies yielded six known compounds, including pinostrobin 1, 4′-methyl ether sakuranetin 2, sakuranetin 3, pinostrobin chalcone 4, yashabushidiol A 5, and desmethoxyyangonin 6. Compound 6 displayed about 30-fold higher affinity for MAO-B than MAO-A, with Ki values of 31 and 922 nM, respectively. Kinetic analysis of inhibition and equilibrium-dialysis dissociation assay of the enzyme-inhibitor complex showed reversible binding of desmethoxyyangonin 6 with MAO-A and MAO-B. The binding interactions of compound 6 in the active site of the MAO-A and MAO-B isoenzymes, investigated through molecular modeling algorithms, confirmed preferential binding of desmethoxyyangonin 6 with MAO-B compared to MAO-A. Selective reversible inhibitors of MAO-B, like desmethoxyyangonin 6, may have important therapeutic significance for the treatment of neurodegenerative disorders, such as Parkinson’s disease and Alzheimer’s disease.

Title

Interactions of Desmethoxyyangonin, a Secondary Metabolite From Renealmia alpinia, With Human Monoamine Oxidase-A and Oxidase-B

Author

Narayan D Chaurasiya 1 , Francisco Leon 2 , Yuanqing Ding 1 , Isabel Gomez-Betancur 3 , Dora Benjumea 3 , Larry A Walker 1 2 , Stephen J Cutler 1 4 , Babu L Tekwani 1 2

Publish date

2017

PMID

15282211

Abstract

Kava kava (Piper methysticum), an herbal remedy, is widely used for the treatment of mild to moderate cases of anxiety. The therapeutic activity is presumably achieved through multiple constituents called kavalactones. Recently, kava extracts were shown to induce CYP3A4 and activate human pregnane X receptor (PXR). This study was undertaken to test the ability of purified kavalactones to induce CYP3A23 and activate PXR. Rat hepatocytes were treated with desmethoxyyangonin, dihydrokawain, dihydromethysticin, kawain, methysticin, or yangonin, and the expression of CYP3A23 was monitored. Among the kavalactones, only desmethoxyyangonin and dihydromethysticin markedly induced the expression of CYP3A23 (approximately 7-fold). A similar magnitude of induction was detected with combined six kavalactones at a noninductive concentration when individually used. The induced expression, however, was markedly reduced or completely abolished if dihydromethysticin, desmethoxyyangonin, or both were excluded from the mixtures. Interestingly, regardless of whether dihydromethysticin or desmethoxyyangonin was used alone or together with other kavalactones, similar amounts of total kavalactones were needed to produce comparable induction, suggesting that the inductive activity of dihydromethysticin and desmethoxyyangonin is additively/synergistically enhanced by other kavalactones. In addition, treatment with dihydromethysticin, desmethoxyyangonin, or pregnenolone 16alpha-carbonitrile (PCN) markedly increased the levels of CYP3A23 mRNA, and inhibition of mRNA synthesis abolished the induction. In contrast to PCN, dihydromethysticin and desmethoxyyangonin only slightly activated rat or human PXR. These findings suggest that the induction of CYP3A23 by dihydromethysticin and desmethoxyyangonin involves transcription activation, probably through a PXR-independent or PXR-involved indirect mechanism.
Copyright 2004 The American Society for Pharmacology and Experimental Therapeutics

Title

Desmethoxyyangonin and Dihydromethysticin Are Two Major Pharmacological Kavalactones With Marked Activity on the Induction of CYP3A23

Author

Yuzhong Ma 1 , Karuna Sachdeva, Jirong Liu, Michael Ford, Dongfang Yang, Ikhlas A Khan, Clinton O Chichester, Bingfang Yan

Publish date

2004 Nov

PMID

18661482

Abstract

Three novel, simple and reproducible high-performance liquid chromatography quantitative assays with UV detection were developed and validated for three major kavalactones–desmethoxyyangonin, methysticin and kavain–in rat liver microsomes using diazepam as an internal standard; liquid-liquid extraction was used for sample preparation and analysis was performed on a Shimadzu 10A high-performance liquid chromatography system. The analysis was carried out in reversed-phase mode with a Luna C(18) column (150 x 2.00 mm, 3 microm) at 40 degrees C. The limit of quantitation was 0.1 microg/mL using 0.25 mL of microsomal solution. The assays were linear over the range 0.1-10 microg/mL for desmethoxyyangonin, methysticin and kavain. Quality control samples exhibited good accuracy and precision with relative standard deviations lower than 15% and recoveries between 85 and 105%. The assays exhibited satisfactory performance with high sensitivity for quantifying desmethoxyyangonin, methysticin and kavain in rat liver microsomes and were successfully used to determine the three kavalactones and their microsomal metabolites.

Title

High-performance Liquid Chromatography Assays for Desmethoxyyangonin, Methysticin, Kavain and Their Microsomal Metabolites

Author

Shuang Fu 1 , Bruce N Tattam, Colin C Duke, Iqbal Ramzan

Publish date

2009 Jan


Description :

Desmethoxyyangonin is one of the six major kavalactones found in the Piper methysticum (kava) plant; reversible inhibitor of MAO-B.