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Liguiritigenin-7-O-D-apiosyl-4'-O-D-glucoside

CAS# 199796-12-8

Liguiritigenin-7-O-D-apiosyl-4'-O-D-glucoside

2D Structure

Catalog No. BCN2840----Order now to get a substantial discount!

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Liguiritigenin-7-O-D-apiosyl-4'-O-D-glucoside: 5mg Please Inquire In Stock
Liguiritigenin-7-O-D-apiosyl-4'-O-D-glucoside: 10mg Please Inquire In Stock
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Liguiritigenin-7-O-D-apiosyl-4'-O-D-glucoside: 50mg Please Inquire Please Inquire
Liguiritigenin-7-O-D-apiosyl-4'-O-D-glucoside: 100mg Please Inquire Please Inquire
Liguiritigenin-7-O-D-apiosyl-4'-O-D-glucoside: 200mg Please Inquire Please Inquire
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Quality Control of Liguiritigenin-7-O-D-apiosyl-4'-O-D-glucoside

3D structure

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Liguiritigenin-7-O-D-apiosyl-4'-O-D-glucoside

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Chemical Properties of Liguiritigenin-7-O-D-apiosyl-4'-O-D-glucoside

Cas No. 199796-12-8 SDF Download SDF
PubChem ID 124578359 Appearance Powder
Formula C26H30O13 M.Wt 550.5
Type of Compound Flavonoids Storage Desiccate at -20°C
Synonyms iquiritigeninyl-7-O--D-furanapiosyl-4'-O--D-glucopyranoside
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name (2S)-7-[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-2-[4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-2,3-dihydrochromen-4-one
SMILES C1C(OC2=C(C1=O)C=CC(=C2)OC3C(C(CO3)(CO)O)O)C4=CC=C(C=C4)OC5C(C(C(C(O5)CO)O)O)O
Standard InChIKey KEABDZDFSMGRQX-DWMQJYMWSA-N
Standard InChI InChI=1S/C26H30O13/c27-9-19-20(30)21(31)22(32)24(39-19)36-13-3-1-12(2-4-13)17-8-16(29)15-6-5-14(7-18(15)38-17)37-25-23(33)26(34,10-28)11-35-25/h1-7,17,19-25,27-28,30-34H,8-11H2/t17-,19+,20+,21-,22+,23-,24+,25-,26+/m0/s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of Liguiritigenin-7-O-D-apiosyl-4'-O-D-glucoside

The roots of Glycyrrhiza uralensis Fisch

Biological Activity of Liguiritigenin-7-O-D-apiosyl-4'-O-D-glucoside

DescriptionLiquiritin apioside has antioxidant property by inducing glutathione (GSH) biosynthesis via the inhibition of cytokines and protected lung epithelial cells against cigarette smoke-mediated oxidative stress, might be as protective agent against epithelial injury in COPD.
TargetsTNF-α | TGF-β/Smad
In vivo

Protective effects of liquiritin apioside on cigarette smoke-induced lung epithelial cell injury. [Pubmed: 21631586]

Fundam Clin Pharmacol. 2012 Aug;26(4):473-83.

Cigarette smoking is associated with an increased incidence of chronic obstructive pulmonary disease (COPD).
METHODS AND RESULTS:
In this study, we hypothesized that Liquiritin apioside (LA), a main flavonoid component from Glycyrrhiza uralensis, had antioxidant properties by inducing glutathione (GSH) biosynthesis via the inhibition of cytokines and protected lung epithelial cells against cigarette smoke-mediated oxidative stress. A549 cells were treated with cigarette smoke extract (CSE) and/or LA. ICR mice were exposed to cigarette smoke (CS) for four days with increasing exposure time for up to 6 h per day to elicit epithelial cells injury. One hour before smoke exposure, mice were treated with LA by gavage; 18 h after the last CS exposure all examinations were performed. Treatment with LA concentration-dependently prevented CSE-induced cytotoxicity, increase of TGF-β and TNF-α mRNA expression, depletion of GSH and apoptosis in A549 cells. LA at doses 3, 10 and 30 mg/kg dose-dependently inhibited pulmonary neutrophil and macrophage inflammation. Lung sections of the CS-exposed LA treated mice showed an apparently reduced pulmonary inflammation and a significant inhibitory effect on mucus containing goblet cells in the large airways. Furthermore, the CS-induced pulmonary release of TGF-β, TNF-α and myeloperoxidase activity was reduced, and superoxide dismutase activity was enhanced.
CONCLUSIONS:
These results indicate that protective roles of LA on CS-induced the lung epithelial cell injury are mediated by inhibiting TGF-β and TNF-α expression and increasing anti-oxidative levels of GSH, suggesting that LA might be effective as protective agent against epithelial injury in COPD.

Liguiritigenin-7-O-D-apiosyl-4'-O-D-glucoside Dilution Calculator

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Liguiritigenin-7-O-D-apiosyl-4'-O-D-glucoside Molarity Calculator

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Preparing Stock Solutions of Liguiritigenin-7-O-D-apiosyl-4'-O-D-glucoside

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 1.8165 mL 9.0827 mL 18.1653 mL 36.3306 mL 45.4133 mL
5 mM 0.3633 mL 1.8165 mL 3.6331 mL 7.2661 mL 9.0827 mL
10 mM 0.1817 mL 0.9083 mL 1.8165 mL 3.6331 mL 4.5413 mL
50 mM 0.0363 mL 0.1817 mL 0.3633 mL 0.7266 mL 0.9083 mL
100 mM 0.0182 mL 0.0908 mL 0.1817 mL 0.3633 mL 0.4541 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on Liguiritigenin-7-O-D-apiosyl-4'-O-D-glucoside

Protective effects of liquiritin apioside on cigarette smoke-induced lung epithelial cell injury.[Pubmed:21631586]

Fundam Clin Pharmacol. 2012 Aug;26(4):473-83.

Cigarette smoking is associated with an increased incidence of chronic obstructive pulmonary disease (COPD). In this study, we hypothesized that liquiritin apioside (LA), a main flavonoid component from Glycyrrhiza uralensis, had antioxidant properties by inducing glutathione (GSH) biosynthesis via the inhibition of cytokines and protected lung epithelial cells against cigarette smoke-mediated oxidative stress. A549 cells were treated with cigarette smoke extract (CSE) and/or LA. ICR mice were exposed to cigarette smoke (CS) for four days with increasing exposure time for up to 6 h per day to elicit epithelial cells injury. One hour before smoke exposure, mice were treated with LA by gavage; 18 h after the last CS exposure all examinations were performed. Treatment with LA concentration-dependently prevented CSE-induced cytotoxicity, increase of TGF-beta and TNF-alpha mRNA expression, depletion of GSH and apoptosis in A549 cells. LA at doses 3, 10 and 30 mg/kg dose-dependently inhibited pulmonary neutrophil and macrophage inflammation. Lung sections of the CS-exposed LA treated mice showed an apparently reduced pulmonary inflammation and a significant inhibitory effect on mucus containing goblet cells in the large airways. Furthermore, the CS-induced pulmonary release of TGF-beta, TNF-alpha and myeloperoxidase activity was reduced, and superoxide dismutase activity was enhanced.These results indicate that protective roles of LA on CS-induced the lung epithelial cell injury are mediated by inhibiting TGF-beta and TNF-alpha expression and increasing anti-oxidative levels of GSH, suggesting that LA might be effective as protective agent against epithelial injury in COPD.

Description

Liguiritigenin-7-O-D-apiosyl-4'-O-D-glucoside is a flavanone glycoside isolated from Glycyrrhizia inflate.

Keywords:

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