Avicularin

Alias: Quercetin; 3-O-α-L-arabinofuranoside; Avicularin
Cat No.:V30086 Purity: ≥98%
Avicularin is a novel and potent flavonoid.
Avicularin Chemical Structure CAS No.: 572-30-5
Product category: NF-κB
This product is for research use only, not for human use. We do not sell to patients.
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Product Description

Avicularin is a naturally occurring flavonoid isolated from plants, with anti-inflammatory, anti-allergic, anti-oxidant, hepatoprotective, and anti-tumor activities. controls the activities of PPAR-γ, COX-2, and NF-κB (p65).

Biological Activity I Assay Protocols (From Reference)
Targets
GLUT4; PPARγ; COX-2
ln Vitro
In LPS-stimulated RAW 264.7 cells, avicuLarin (10-300 μM, 1 hour) suppresses the generation of NO and PGE2 [1]. In LPS-stimulated RAW 264.7 cells, AvicuLarin (10-300 μM, 1 h) suppresses ERK signaling. In Huh7 cells, AvicuLarin (25-100 μg/mL, 48 h) decreases apex, proliferation, and cell migration [2]. By reporting NF, AvicuLarin (25-100 μg/mL, 48 h) demonstrates anti-inflammatory efficacy [1]. AvicuLarin (50 μM, 6 days) decreases 3T3-L1 cells, PPARγ, and C/EBPα in addition to intracellular toxins. -κB (p65) causes an increase in PPAR-γ and COX-2 expression as well as cell disinfection [2]. 3T3-L1 cells' quantitative dose-mediated GLUT4-mediated inhibition is inhibited by avicuLarin (50 μM, 6 days) [3]. AvicuLarin (2.5-10 μM, 2 hours) increases the amounts of aP2 mRNA in both human formulations and solutions [3].
ln Vivo
AvicuLarin, an intra-articular injection administered twice weekly for four weeks at a dose of 0.5-2 mg/kg, inhibits the progression of stent OA (osteoarthritis) caused by ACLT [4]. AvicuLarin (Laterolateralis, 50 and 100 mg/kg for 21 days) impairs memory in deposits of Alzheimer's disease caused by amyloid beta [5].
Cell Assay
Cell proliferation assay [2]
Cell Types: Huh7 cells
Tested Concentrations: 25, 50, 100 μg/mL
Incubation Duration: 12, 24, 36 and 48 h
Experimental Results: Inhibition of cell proliferation was dose-dependent.

Western Blot Analysis [1]
Cell Types: RAW 264.7 Cell
Tested Concentrations: 10, 30, 100, 300 μM
Incubation Duration: 1 h
Experimental Results: Inhibited LPS-induced iNOS and COX-2 protein expression, released pro-inflammatory cytokines IL-1β, Cytoplasmic IκB degradation and ERK phosphorylation.

RT-PCR[3]
Cell Types: 3T3-L1 Cell
Tested Concentrations: 50 μM
Incubation Duration: 6 days
Experimental Results: PPARγ, C/EBPα and aP2 mRNA levels were diminished by approximately 28.7%, 69.5 and 18.3% respectively.
Animal Protocol
Animal/Disease Models: ACLT (anterior cruciate ligament transection) induced rats [4]
Doses: 0.5, 1, 2mg/kg
Route of Administration: Inject into the right knee joint cavity, twice a week for 4 weeks.
Experimental Results: Reduce tibial subchondral osteolysis, reduce bone loss, and increase tibial subchondral bone mass. Attenuated ECM degradation and loss of aggrecan and type II collagen in ACLT-induced rats. diminished MMP3 and MMP13 protein levels.

Animal/Disease Models: Rats with beta-amyloid-induced Alzheimer's disease [5]
Doses: 25, 50 and 100 mg/kg
Route of Administration: Orally for 21 days
Experimental Results: Enhanced cognitive activity , reverses the effects of amyloid-induced inflammatory responses and excessive oxidative stress.
References
[1]. Vo VA, et al. Avicularin Inhibits Lipopolysaccharide-Induced Inflammatory Response by Suppressing ERK Phosphorylation in RAW 264.7 Macrophages. Biomol Ther (Seoul). 2012 Nov;20(6):532-7.
[2]. Wang Z, et al. Avicularin ameliorates human hepatocellular carcinoma via the regulation of NF‑κB/COX‑2/PPAR‑γ activities. Mol Med Rep. 2019 Jun;19(6):5417-5423.
[3]. Ko Fujimori, et al. Avicularin, a plant flavonoid, suppresses lipid accumulation through repression of C/EBPα-activated GLUT4-mediated glucose uptake in 3T3-L1 cells. J Agric Food Chem. 2013 May 29;61(21):5139-47.
[4]. Zi-Ling Zou, et al. Avicularin suppresses cartilage extracellular matrix degradation and inflammation via TRAF6/MAPK activation. Phytomedicine. 2021 Oct;91:153657.
[5]. Nikita Patil Samant, et al. Avicularin Attenuates Memory Impairment in Rats with Amyloid Beta-Induced Alzheimer's Disease. Neurotox Res. 2022 Feb;40(1):140-153.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C₂₀H₁₈O₁₁
Molecular Weight
434.35
Exact Mass
434.0849
Elemental Analysis
C, 55.31; H, 4.18; O, 40.52
CAS #
572-30-5
Related CAS #
572-30-5
Appearance
Solid powder
SMILES
C1=CC(=C(C=C1C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)O[C@H]4[C@@H]([C@H]([C@@H](O4)CO)O)O)O)O
InChi Key
BDCDNTVZSILEOY-UXYNSRGZSA-N
InChi Code
InChI=1S/C20H18O11/c21-6-13-15(26)17(28)20(30-13)31-19-16(27)14-11(25)4-8(22)5-12(14)29-18(19)7-1-2-9(23)10(24)3-7/h1-5,13,15,17,20-26,28H,6H2/t13-,15-,17+,20-/m0/s1
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
Synonyms
Quercetin; 3-O-α-L-arabinofuranoside; Avicularin
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Note: This product requires protection from light (avoid light exposure) during transportation and storage.
Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO: ~100 mg/mL (~230.2 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.08 mg/mL (4.79 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.08 mg/mL (4.79 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 2.3023 mL 11.5115 mL 23.0229 mL
5 mM 0.4605 mL 2.3023 mL 4.6046 mL
10 mM 0.2302 mL 1.1511 mL 2.3023 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

Biological Data
  • Avicularin inhibits Huh7 cell proliferation in hepatocellular carcinoma. Mol Med Rep . 2019 Jun;19(6):5417-5423.
  • Avicularin repress the migration and invasion of Huh7 cells. Mol Med Rep . 2019 Jun;19(6):5417-5423.
  • Cell were stained with propidium iodide and the cell cycle distributions and cell apoptosis were measured by flow cytometry. Mol Med Rep . 2019 Jun;19(6):5417-5423.
  • Expression of NF-κB (p65), COX-2 and PPAR-γ. Mol Med Rep . 2019 Jun;19(6):5417-5423.
  • Chemical structure of avicularin. Biomol Ther (Seoul) . 2012 Nov;20(6):532-7.
  • Avicularin significantly attenuated LPS-induced overproduction of NO. Biomol Ther (Seoul) . 2012 Nov;20(6):532-7.
  • Avicularin significantly suppressed LPS-induced iNOS and COX-2 expressions in RAW 264.7 cells. Biomol Ther (Seoul) . 2012 Nov;20(6):532-7.
  • Avicularin inhibited the release IL-1β. Biomol Ther (Seoul) . 2012 Nov;20(6):532-7.
  • Avicularin suppressed LPS-induced IκB-α degration in RAW 264.7 macrophage cells. Biomol Ther (Seoul) . 2012 Nov;20(6):532-7.
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