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Prunetin

$325

  • Brand : BIOFRON

  • Catalogue Number : BF-P1015

  • Specification : 98%

  • CAS number : 552-59-0

  • Formula : C16H12O5

  • Molecular Weight : 284.26

  • PUBCHEM ID : 5281804

  • Volume : 5mg

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Catalogue Number

BF-P1015

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

2-8°C

Molecular Weight

284.26

Appearance

Powder

Botanical Source

herbs of Millettia dielsiana

Structure Type

Flavonoids

Category

Standards;Natural Pytochemical;API

SMILES

COC1=CC(=C2C(=C1)OC=C(C2=O)C3=CC=C(C=C3)O)O

Synonyms

5-Hydroxy-3-(4-hydroxyphenyl)-7-methoxy-4H-chromen-4-one/Prunusetin/5,4'-dihydroxy-7-methoxyisoflavone/Prunetin/7-methoxy-4',5-dihydroxyisoflavone/5-hydroxy-3-(4-hydroxyphenyl)-7-methoxychromen-4-one/7-O-methyl-genistein/4',5-dihydroxy-7-methoxyisoflavone/4',5-dihydroxy-7-methoxygenistein/4H-1-Benzopyran-4-one, 5-hydroxy-3-(4-hydroxyphenyl)-7-methoxy-

IUPAC Name

5-hydroxy-3-(4-hydroxyphenyl)-7-methoxychromen-4-one

Density

1.4±0.1 g/cm3

Solubility

Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.

Flash Point

209.7±23.6 °C

Boiling Point

546.5±50.0 °C at 760 mmHg

Melting Point

240-242ºC

InChl

InChI=1S/C16H12O5/c1-20-11-6-13(18)15-14(7-11)21-8-12(16(15)19)9-2-4-10(17)5-3-9/h2-8,17-18H,1H3

InChl Key

KQMVAGISDHMXJJ-UHFFFAOYSA-N

WGK Germany

RID/ADR

HS Code Reference

2914500000

Personal Projective Equipment

Correct Usage

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

Meta Tag

provides coniferyl ferulate(CAS#:552-59-0) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

31307793

Abstract

Starting with an isoflavone-rich red clover extract (RCE), this study expands on the DESIGNER approach to Deplete and Enrich Select Ingredients to Generate Normalized Extract Resources using countercurrent separation (CCS) methodology. A hydrostatic CCS (also known as centrifugal partition chromatography, CPC) technique was used to enrich and deplete selected bioactive isoflavones of RCE extracts. In order to efficiently prepare large enough DESIGNER extracts from RCE for biological testing including in vivo assays, it was necessary to choose a balance between resolution and a loading capacity of at least 1 g per separation for the selected solvent system (SS). Adding 3 mL of DMSO to the sample containing equal amounts of upper and lower phases of hexanes-ethyl acetate-methanol-water (HEMWat 5.5/4.5/5/5, v/v) allowed 1 g of RCE to be dissolved in the sample without disrupting the chromatographic resolution of the target isoflavones. CPC experiments using other solubility modifiers, acetone and acetonitrile indicated that these modifiers increase solubility significantly, even better than DMSO, but the separation of target compounds was sufficiently disturbed to be unacceptable for producing the desired DESIGNER extracts. The preparation of DESIGNER extracts was achieved with two sequential CPC separations. The first produced a biochanin A enriched fraction (93.60% w/w) with only small amounts of other isoflavones: 2.30% w/w prunetin, 1.17% w/w formononetin, and 0.12% w/w irilone. Gravimetric investigations of this step demonstrated the high efficiency of CCS technology for full and unbiased sample recovery, confirmed experimentally to be 99.80%. A formononetin enriched fraction from this first separation was re-chromatographed on a more polar HEMWat (4/6/4/6, v/v) SS to produce a formononetin enriched DESIGNER fraction of 94.70% w/w purity. The presence of the minor (iso)flavonoids: 3.16% w/w pseudobaptigenin, 0.39% w/w kaempferol, and 0.31% w/w genistein was also monitored in these fractions. Chromatographic fractions, combined fractions, and DESIGNER extracts were analyzed with quantitative 1H NMR (qHNMR) spectroscopy which provided purity information, quantitation, and structural identification of the components.

Copyright © 2019 Elsevier B.V. All rights reserved.

KEYWORDS

Biochanin A; Centrifugal partition chromatography (CPC); Countercurrent separation (CCS); DESIGNER extracts; Formononetin; Isoflavones; Trifolium pratense L

Title

Preparation of DESIGNER extracts of red clover (Trifolium pratense L.) by centrifugal partition chromatography.

Author

Malca Garcia GR1, Friesen JB2, Liu Y1, Nikolić D3, Lankin DC3, McAlpine JB3, Chen SN3, Pauli GF4.

Publish date

2019 Nov 8

PMID

30227625

Abstract

Prunetin, a component of herbal medicines and various foods, such as pea, peach, cherry, and Prunus yedoensis, is a useful pharmacological compound. We previously reported the potent vasorelaxant effect of the bark of P. yedoensis. Therefore, we investigated the vasorelaxant activities of prunetin on isolated rat aortic rings and hypotensive activity on spontaneously hypertensive rats (SHR) in this study. In the present study, prunetin (1⁻30 μg/mL) relaxed isolated rat aortic rings pre-contracted by phenylephrine (PE) in a concentration-dependent manner. Pre-incubation with prunetin (3 and 10 μg/mL) inhibited vasoconstriction induced by the supply of Ca2+ in rat aortic rings pre-contracted with PE or KCl in a Ca2+-free Krebs⁻Henseleit (KH) buffer. Prunetin (10 μg/mL) pre-treatment also inhibited caffeine-induced contraction of aortic rings in a Ca2+-free KH buffer. To investigate the hypotensive effect of prunetin, the systolic blood pressure (SBP) of the SHR was measured by using a tail cuff assay. The SBP of SHR was significantly lower in the prunetin (25 mg/kg)-treated group. These results suggested that prunetin decreased blood pressure and relaxed blood vessels by blocking receptor-operated calcium channels, voltage-dependent calcium channels, and ryanodine receptor channels.

KEYWORDS

blood pressure; calcium channels; hypertension; prunetin; vasorelaxation

Title

Prunetin Relaxed Isolated Rat Aortic Rings by Blocking Calcium Channels.

Author

Kim B1, Jo C2, Choi HY3, Lee K4.

Publish date

2018 Sep 17;

PMID

30119221

Abstract

Allergic rhinitis (AR) is a chronic upper respiratory disorder characterized by inflammation of the nasal mucosa. Prunetin is an O-methylated isoflavone, which has been found to possess anti-inflammatory activity. The aim of the current study was to evaluate the effect of prunetin on inflammatory cytokine and mucus production and its underlying mechanism in nasal epithelial cells. Results showed that treatment with prunetin (10, 30, and 50 μM) inhibited lipopolysaccharide (LPS)-induced expression and secretion of interleukin (IL)-6, IL-8, and mucin 5 AC (MUC5 AC) in RPMI2650 cells, and attenuated the effect of LPS on toll-like receptor 4 (TLR4) and myeloid differentiation primary response 88 (MyD88) expression. TAK-242 (an inhibitor of TLR4) treatment or TLR4 knockdown attenuated LPS-induced expression and secretion of IL-6, IL-8 and MUC5 AC. In conclusion, prunetin inhibited LPS-induced inflammatory cytokine production and MUC5 AC expression and secretion by inactivating the TLR4/MyD88 pathway in human nasal epithelial cells. These results suggested that prunetin might be a useful agent in the treatment of AR.

Copyright © 2018 Elsevier Masson SAS. All rights reserved

KEYWORDS

Allergic rhinitis; Inflammatory cytokine; MUC5AC; Prunetin; TLR4/MyD88 pathway

Title

Prunetin inhibits lipopolysaccharide-induced inflammatory cytokine production and MUC5AC expression by inactivating the TLR4/MyD88 pathway in human nasal epithelial cells.

Author

Hu H1, Li H2.

Publish date

2018 Oct


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