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Isoliquiritin

$113

  • Brand : BIOFRON

  • Catalogue Number : BF-I1006

  • Specification : 98%

  • CAS number : 5041-81-6

  • Formula : C21H22O9

  • Molecular Weight : 418.39

  • PUBCHEM ID : 5318591

  • Volume : 20mg

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Catalogue Number

BF-I1006

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

-20℃

Molecular Weight

418.39

Appearance

White crystal

Botanical Source

root of Glycyrrhiza uralensis Fisch.

Structure Type

Flavonoids

Category

Standards;Natural Pytochemical;API

SMILES

C1=CC(=CC=C1C=CC(=O)C2=C(C=C(C=C2)O)O)OC3C(C(C(C(O3)CO)O)O)O

Synonyms

2-Propen-1-one, 1-(2,4-dihydroxyphenyl)-3-[4-(β-D-glucopyranosyloxy)phenyl]-, (2E)-/Isoliquiritin/(E)-1-(2,4-dihydroxyphenyl)-3-[4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]prop-2-en-1-one/2-Propen-1-one, 1-(2,4-dihydroxyphenyl)-3-(4-(β-D-glucopyranosyloxy)phenyl)-, (2E)-/4-[(1E)-3-(2,4-Dihydroxyphenyl)-3-oxo-1-propen-1-yl]phenyl β-D-glucopyranoside

IUPAC Name

(E)-1-(2,4-dihydroxyphenyl)-3-[4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]prop-2-en-1-one

Density

1.5±0.1 g/cm3

Solubility

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

Flash Point

263.3±26.4 °C

Boiling Point

743.5±60.0 °C at 760 mmHg

Melting Point

185-186ºC

InChl

InChI=1S/C21H22O9/c22-10-17-18(26)19(27)20(28)21(30-17)29-13-5-1-11(2-6-13)3-8-15(24)14-7-4-12(23)9-16(14)25/h1-9,17-23,25-28H,10H2/b8-3+/t17-,18-,19+,20-,21-/m1/s1

InChl Key

YNWXJFQOCHMPCK-LXGDFETPSA-N

WGK Germany

RID/ADR

HS Code Reference

2932990000

Personal Projective Equipment

Correct Usage

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

Meta Tag

provides coniferyl ferulate(CAS#:5041-81-6) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

30876941

Abstract

AIMS:
Liquorice is a widely used herbal medicine for treating various diseases native to southern Europe and parts of Asia. Isoliquiritin (ISL), a licorice root-derived flavonoid, has been reported to exhibit antioxidant, anti-inflammatory, anti-genotoxic activity and anti-depression activities. This study was aimed to explore the pro-angiogenic activity of ISL and explicate the underlying mechanism.

MAIN METHODS:
In vitro, ISL-treated human umbilical vein endothelial cells (HUVECs) were analyzed for cell viability, cell migration and tube formation. In vivo, pro-angiogenic effects were evaluated for the intersegmental vessels (ISVs) formation in transgenic zebrafish embryos [Tg(fli-1: EGFP)]. Furthermore, a blocking assay with eight pathways-specific kinase inhibitors were also used to determine the potential pro-angiogenic mechanism of ISL.

KEY FINDINGS:
ISL counteracted tyrosine kinase inhibitor II (VRI)-induced endothelial cell apoptosis and promoted cell migration and tube formation in HUVECs. ISL markedly rescued ISVs loss induced by VRI in zebrafish embryos, probably by activating vascular endothelial growth factor receptor-2 (VEGFR-2), phosphoinositide 3-kinase (PI3K), Raf and mitogen-activated protein kinase (MEK)-dependent signaling pathways.

SIGNIFICANCE:
Our study first discovered and confirmed the pro-angiogenic activity of ISL both in HUVECs and zebrafish. Thus, ISL could be developed as a potential therapeutic agent by the role of pro-angiogenic activity for the treatment of cardiovascular diseases, cerebrovascular diseases and other vascular diseases.

Copyright © 2019 Elsevier Inc. All rights reserved.

KEYWORDS

HUVECs; Inhibitors; Isoliquiritin; Pro-angiogenic activity; Zebrafish

Title

Pro-angiogenic activity of isoliquiritin on HUVECs in vitro and zebrafish in vivo through Raf/MEK signaling pathway.

Author

Zhang XH1, Li CY1, Lin QH2, He ZH3, Feng F2, He MF4.

Publish date

2019 Apr 15

PMID

30818413

Abstract

Lizhong decoction (LZD), a classic formula, has been used to treat ulcerative colitis (UC) for thousands of years in clinical practice. However, the pharmacokinetic characteristics of its major bioactive components in rats under different physiological and pathological states are not clear. Thus, in this study, a rapid and sensitive analytical method, ultra-performance liquid chromatography coupled with mass spectrometry (UPLC-MS/MS) method, was developed and applied to simultaneously determine glycyrrhizic acid, liquiritin, isoliquiritin, glycyrrhizin, isoliquiritigenin, 6-gingerol, ginsenoside Rg1, ginsenoside Rb1 and ginsenoside Re in normal and UC rats after oral administration of LZD extract. A Waters BEH C18 UPLC column was used for chromatographic separation, while acetonitrile and 0.1% formic acid were selected as mobile phase. The linearity of nine analytes was >0.9920. Inter- and intra-day accuracy was ≤ 11.4% and precision was from 1.1 to 12.7%. Additionally, stable and suitable extraction recoveries were also obtained. The established method was validated and found to be specific, accurate and precise for nine analytes. Furthermore, it was successfully applied to the pharmacokinetic investigation of nine major components after oral administration of LZD extracts to normal and model rats, respectively. The results showed that the pharmacokinetic parameters (Cmax , Tmax , AUC0-t , AUC0-∞ ) in the plasma of UC rats were significantly different from those of normal rats, which could provide a reference for the clinical application of LZD.

© 2019 John Wiley & Sons, Ltd.

KEYWORDS

LZD; UPLC-MS/MS; pharmacokinetics; ulcerative colitis

Title

Comparative pharmacokinetics of nine major bioactive components in normal and ulcerative colitis rats after oral administration of Lizhong decoction extracts by UPLC-TQ-MS/MS.

Author

Shen Y1, Cui X1, Jiang S1, Qian DW1, Duan JA1.

Publish date

2019 Jul

PMID

30209468

Abstract

Screening active constituents of traditional Chinese medicines (TCMs) is vital for lead compound discovery. Sini decoction (SND) is a well-known TCM formula for relieving myocardial ischemia (MI) in clinic. Due to complex nature, the effective compounds of SND are still unknown. In this study, a novel “system to system” strategy based on the correlation of drug-related and drug-induced ultra-high performance liquid chromatography coupled with quadrupole-time-of-flight mass spectrometry (UHPLC-Q-TOFMS) serum metabolomic profiles was developed to discover bioactive compounds of SND against isoproterenol-induced MI. Thirteen SND-induced metabolites and 19 SND-related metabolites were identified by UHPLC-Q-TOFMS coupled with S-plot and SUS-plot of orthogonal projection to latent structure-discriminant analysis (OPLS-DA) models, respectively. Canonical correlation analysis between the SND-induced and SND-related metabolites revealed that 12 compounds had strongly correlated relationship with the protective effect of SND on MI, and these compounds include isotalatizidine, songorine, fuziline, neoline, talatizamine, 14-acetyltalatizamine, liquiritigenin, benzoylmesaconitine, isoliquiritin, benzoylaconitne, benzoylhypaconitine and 6-gingerol. Combination functional enrichment analysis and network topology analysis revealed that the targeted metabolic pathways of these correlated compounds were involved in valine, leucine and isoleucine biosyntheses, tryptophan metabolism, glycerophospholipid metabolism and sphingolipid metabolism. The results demonstrated that the “system to system” strategy may be a high-throughput method to discover potentially effective compounds from TCMs.

Title

Correlation of drug-induced and drug-related ultra-high performance liquid chromatography-mass spectrometry serum metabolomic profiles yields discovery of effective constituents of Sini decoction against myocardial ischemia in rats.

Author

Tan G 1, Wang X , Liu K , Dong X , Liao W , Wu H .

Publish date

2018 Nov 14


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