Avicularin

CAS# 572-30-5

Avicularin

Catalog No. BCN5771----Order now to get a substantial discount!

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Quality Control of Avicularin

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Chemical structure

Avicularin

3D structure

Chemical Properties of Avicularin

Cas No. 572-30-5 SDF Download SDF
PubChem ID 5490064 Appearance Yellow powder
Formula C20H18O11 M.Wt 434.4
Type of Compound Flavonoids Storage Desiccate at -20°C
Synonyms Avicularoside; 3,3',4',5,7-Pentahydroxyflavone 3-O-α-L-arabinofuranoside; Quercetin 3-α-L-arabinofuranoside
Solubility Soluble in DMSO and methan
Chemical Name 3-[(2S,3R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromen-4-one
SMILES C1=CC(=C(C=C1C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)OC4C(C(C(O4)CO)O)O)O)O
Standard InChIKey BDCDNTVZSILEOY-UXYNSRGZSA-N
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 Avicularin

1 Arctium sp. 2 Chimaphila sp. 3 Dryas sp. 4 Hypericum sp. 5 Larix sp. 6 Persicaria sp. 7 Polygonum sp. 8 Rhododendron sp. 9 Rhus sp. 10 Sanguisorba sp. 11 Vaccinium sp.

Biological Activity of Avicularin

DescriptionAvicularin exhibits anti-inflammatory activity through the suppression of ERK signaling pathway in LPS-stimulated RAW 264.7 macrophage cells; it inhibits the accumulation of the intracellular lipids by decreasing C/EBPα-activated GLUT4-mediated glucose uptake in adipocytes and potently inhibiting fatty acid synthase.
TargetsGLUT | NO | PGE | NOS | COX | NF-kB | IkB | ERK | IL Receptor | IKK
In vitro

Avicularin Inhibits Lipopolysaccharide-Induced Inflammatory Response by Suppressing ERK Phosphorylation in RAW 264.7 Macrophages.[Pubmed: 24009846]

Biomol Ther (Seoul). 2012 Nov;20(6):532-7.

suppresAvicularin, quercetin-3-α-L-arabinofuranoside, has been reported to possess diverse pharmacological properties such as anti-inflammatory and anti-infectious effects. However, the underlying mechanism by which Avicularin exerts its anti-inflammatory activity has not been clearly demonstrated. This study aimed to elucidate the anti-inflammatory mechanism of Avicularin in lipopolysaccharide (LPS)-stimulated RAW 264.7 macrophage cells.
METHODS AND RESULTS:
Avicularin significantly inhibited LPS-induced excessive production of pro-inflammatory mediators such as nitric oxide (NO) and PGE2 and the protein levels of iNOS and COX-2, which are responsible for the production of NO and PGE2, respectively. Avicularin also suppressed LPS-induced overproduction of pro-inflammatory cytokine IL-1β. Furthermore, Avicularin significantly suppressed LPS-induced degradation of IκB, which retains NF-κB in the cytoplasm, consequently inhibiting the transcription of pro-inflammatory genes by NF-κB in the nucleus. To understand the underlying signaling mechanism of anti-inflammatory activity of Avicularin, involvement of multiple kinases was examined. Avicularin significantly attenuated LPS-induced activation of ERK signaling pathway in a concentration-dependent manner.
CONCLUSIONS:
Taken together, the present study clearly demonstrates that Avicularin exhibits anti-inflammatory activity through the suppression of ERK signaling pathway in LPS-stimulated RAW 264.7 macrophage cells.

In vivo

Pharmacokinetic evaluation of avicularin using a model-based development approach.[Pubmed: 25782034]

Planta Med. 2015 Mar;81(5):373-81.

The aim of this study was to use the pharmacokinetic information of Avicularin in rats to project a dose for humans using allometric scaling.
METHODS AND RESULTS:
A highly sensitive and specific bioanalytical assay to determine Avicularin concentrations in the plasma was developed and validated for UPLC-MS/MS. The plasma protein binding of Avicularin in rat plasma determined by the ultrafiltration method was 64%. The pharmacokinetics of Avicularin in nine rats was studied following an intravenous bolus administration of 1 mg/kg and was found to be best described by a two-compartment model using a nonlinear mixed effects modeling approach. The pharmacokinetic parameters were allometrically scaled by body weight and centered to the median rat weight of 0.23 kg, with the power coefficient fixed at 0.75 for clearance and 1 for volume parameters. Avicularin was rapidly eliminated from the systemic circulation within 1 h post-dose, and the Avicularin pharmacokinetic was linear up to 5 mg/kg based on exposure comparison to literature data for a 5-mg/kg single dose in rats.
CONCLUSIONS:
Using allometric scaling and Monte Carlo simulation approaches, the rat doses of 1 and 5 mg/kg correspond to the human equivalent doses of 30 and 150 mg, respectively, to achieve comparable plasma Avicularin concentrations in humans.

Protocol of Avicularin

Kinase Assay

Potent inhibition of fatty acid synthase by parasitic loranthus [Taxillus chinensis (dc.) danser] and its constituent avicularin.[Pubmed: 16570511]

Avicularin, a plant flavonoid, suppresses lipid accumulation through repression of C/EBPα-activated GLUT4-mediated glucose uptake in 3T3-L1 cells.[Pubmed: 23647459]

J Agric Food Chem. 2013 May 29;61(21):5139-47.

Avicularin (quercetin-3-O-α-L-arabinofuranoside) is a plant flavonoid and a quercetin glycoside. In this study, we found that Avicularin suppressed the accumulation of intracellular lipids through repression of glucose transporter 4 (GLUT4)-mediated glucose uptake in mouse adipocytic 3T3-L1 cells.
METHODS AND RESULTS:
Avicularin was highly purified (purity of more than at least 99%) from Taxillus kaempferi (DC.) Danser (Loranthaceae) by high-performance liquid chromatography, and its structure was determined by nuclear magnetic resonance and mass spectrometry. Avicularin decreased the intracellular triglyceride level along with a reduction in the expression of adipogenic genes such as peroxisome proliferator-activated receptor γ, CCAAT/enhancer-binding protein (C/EBP) α, and aP2 (fatty acid-binding protein 4). In contrast, Avicularin did not affect the expression of lipogenic and lipolytic genes. Interestingly, the expression of the GLUT4 gene was significantly suppressed in an Avicularin-concentration-dependent manner. Moreover, the binding of C/EBPα to the promoter region of the GLUT4 gene was repressed by adding Avicularin to the medium in 3T3-L1 cells, as demonstrated by the results of a chromatin immunoprecipitation assay.
CONCLUSIONS:
These results indicate that Avicularin inhibited the accumulation of the intracellular lipids by decreasing C/EBPα-activated GLUT4-mediated glucose uptake in adipocytes.

J Enzyme Inhib Med Chem. 2006 Feb;21(1):87-93.

The medicinal herb parasitic loranthus in a screen was found to inhibit fatty acid synthase (EC 2.3.1.85, FAS) and reduce body weight of rats in our previous study. Now we have determined the inhibitory characteristics and kinetic parameters of extracts of parasitic loranthus [Taxillus chinensis (DC.) Danser].
METHODS AND RESULTS:
The parasitic loranthus extracts (PLE) inhibits FAS reversibly and irreversibly and with an IC50 value of 0.48 microg/ml, appears to be the most potent inhibitor reported to date. PLE contains various potent inhibitors and may react with different sites on FAS. The irreversible inhibition exhibits a time-dependent biphasic process including a speedy fast-phase during the initial several minutes. The fast-phase inhibition seems to be caused by some potent but low-concentration component(s) in the extracts. In addition, we have found that Avicularin existing in this herb can potently inhibit FAS.
CONCLUSIONS:
This glycosylated flavonoid and quercetin play an effective role in inhibiting FAS by parasitic loranthus.

Avicularin Dilution Calculator

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Preparing Stock Solutions of Avicularin

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.302 mL 11.5101 mL 23.0203 mL 46.0405 mL 57.5506 mL
5 mM 0.4604 mL 2.302 mL 4.6041 mL 9.2081 mL 11.5101 mL
10 mM 0.2302 mL 1.151 mL 2.302 mL 4.6041 mL 5.7551 mL
50 mM 0.046 mL 0.2302 mL 0.4604 mL 0.9208 mL 1.151 mL
100 mM 0.023 mL 0.1151 mL 0.2302 mL 0.4604 mL 0.5755 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 Avicularin

Pharmacokinetic evaluation of avicularin using a model-based development approach.[Pubmed:25782034]

Planta Med. 2015 Mar;81(5):373-81.

The aim of this study was to use the pharmacokinetic information of Avicularin in rats to project a dose for humans using allometric scaling. A highly sensitive and specific bioanalytical assay to determine Avicularin concentrations in the plasma was developed and validated for UPLC-MS/MS. The plasma protein binding of Avicularin in rat plasma determined by the ultrafiltration method was 64%. The pharmacokinetics of Avicularin in nine rats was studied following an intravenous bolus administration of 1 mg/kg and was found to be best described by a two-compartment model using a nonlinear mixed effects modeling approach. The pharmacokinetic parameters were allometrically scaled by body weight and centered to the median rat weight of 0.23 kg, with the power coefficient fixed at 0.75 for clearance and 1 for volume parameters. Avicularin was rapidly eliminated from the systemic circulation within 1 h post-dose, and the Avicularin pharmacokinetic was linear up to 5 mg/kg based on exposure comparison to literature data for a 5-mg/kg single dose in rats. Using allometric scaling and Monte Carlo simulation approaches, the rat doses of 1 and 5 mg/kg correspond to the human equivalent doses of 30 and 150 mg, respectively, to achieve comparable plasma Avicularin concentrations in humans.

Avicularin Inhibits Lipopolysaccharide-Induced Inflammatory Response by Suppressing ERK Phosphorylation in RAW 264.7 Macrophages.[Pubmed:24009846]

Biomol Ther (Seoul). 2012 Nov;20(6):532-7.

suppresAvicularin, quercetin-3-alpha-L-arabinofuranoside, has been reported to possess diverse pharmacological properties such as anti-inflammatory and anti-infectious effects. However, the underlying mechanism by which Avicularin exerts its anti-inflammatory activity has not been clearly demonstrated. This study aimed to elucidate the anti-inflammatory mechanism of Avicularin in lipopolysaccharide (LPS)-stimulated RAW 264.7 macrophage cells. Avicularin significantly inhibited LPS-induced excessive production of pro-inflammatory mediators such as nitric oxide (NO) and PGE2 and the protein levels of iNOS and COX-2, which are responsible for the production of NO and PGE2, respectively. Avicularin also suppressed LPS-induced overproduction of pro-inflammatory cytokine IL-1beta. Furthermore, Avicularin significantly suppressed LPS-induced degradation of IkappaB, which retains NF-kappaB in the cytoplasm, consequently inhibiting the transcription of pro-inflammatory genes by NF-kappaB in the nucleus. To understand the underlying signaling mechanism of anti-inflammatory activity of Avicularin, involvement of multiple kinases was examined. Avicularin significantly attenuated LPS-induced activation of ERK signaling pathway in a concentration-dependent manner. Taken together, the present study clearly demonstrates that Avicularin exhibits anti-inflammatory activity through the suppression of ERK signaling pathway in LPS-stimulated RAW 264.7 macrophage cells.

Potent inhibition of fatty acid synthase by parasitic loranthus [Taxillus chinensis (dc.) danser] and its constituent avicularin.[Pubmed:16570511]

J Enzyme Inhib Med Chem. 2006 Feb;21(1):87-93.

The medicinal herb parasitic loranthus in a screen was found to inhibit fatty acid synthase (EC 2.3.1.85, FAS) and reduce body weight of rats in our previous study. Now we have determined the inhibitory characteristics and kinetic parameters of extracts of parasitic loranthus [Taxillus chinensis (DC.) Danser]. The parasitic loranthus extracts (PLE) inhibits FAS reversibly and irreversibly and with an IC50 value of 0.48 microg/ml, appears to be the most potent inhibitor reported to date. PLE contains various potent inhibitors and may react with different sites on FAS. The irreversible inhibition exhibits a time-dependent biphasic process including a speedy fast-phase during the initial several minutes. The fast-phase inhibition seems to be caused by some potent but low-concentration component(s) in the extracts. In addition, we have found that Avicularin existing in this herb can potently inhibit FAS. This glycosylated flavonoid and quercetin play an effective role in inhibiting FAS by parasitic loranthus.

Avicularin, a plant flavonoid, suppresses lipid accumulation through repression of C/EBPalpha-activated GLUT4-mediated glucose uptake in 3T3-L1 cells.[Pubmed:23647459]

J Agric Food Chem. 2013 May 29;61(21):5139-47.

Avicularin (quercetin-3-O-alpha-L-arabinofuranoside) is a plant flavonoid and a quercetin glycoside. In this study, we found that Avicularin suppressed the accumulation of intracellular lipids through repression of glucose transporter 4 (GLUT4)-mediated glucose uptake in mouse adipocytic 3T3-L1 cells. Avicularin was highly purified (purity of more than at least 99%) from Taxillus kaempferi (DC.) Danser (Loranthaceae) by high-performance liquid chromatography, and its structure was determined by nuclear magnetic resonance and mass spectrometry. Avicularin decreased the intracellular triglyceride level along with a reduction in the expression of adipogenic genes such as peroxisome proliferator-activated receptor gamma, CCAAT/enhancer-binding protein (C/EBP) alpha, and aP2 (fatty acid-binding protein 4). In contrast, Avicularin did not affect the expression of lipogenic and lipolytic genes. Interestingly, the expression of the GLUT4 gene was significantly suppressed in an Avicularin-concentration-dependent manner. Moreover, the binding of C/EBPalpha to the promoter region of the GLUT4 gene was repressed by adding Avicularin to the medium in 3T3-L1 cells, as demonstrated by the results of a chromatin immunoprecipitation assay. These results indicate that Avicularin inhibited the accumulation of the intracellular lipids by decreasing C/EBPalpha-activated GLUT4-mediated glucose uptake in adipocytes.

Description

Avicularin is a bio-active flavonoid from plants, anti-inflammatory, anti-allergic, anti-oxidant, hepatoprotective, and anti-tumor activities. Avicularin exhibits anti-inflammatory activity through the suppression of ERK signaling pathway in LPS-stimulated RAW 264.7 macrophage cells. Avicularin ameliorates human hepatocellular carcinoma via the regulation of NF κB (p65), COX 2 and PPAR γ activities.

Keywords:

Avicularin,572-30-5,Avicularoside; 3,3',4',5,7-Pentahydroxyflavone 3-O-α-L-arabinofuranoside; Quercetin 3-α-L-arabinofuranoside,Natural Products, buy Avicularin , Avicularin supplier , purchase Avicularin , Avicularin cost , Avicularin manufacturer , order Avicularin , high purity Avicularin

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