Quercetagetin

CAS# 90-18-6

Quercetagetin

Catalog No. BCN8729----Order now to get a substantial discount!

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Quality Control of Quercetagetin

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Chemical structure

Quercetagetin

3D structure

Chemical Properties of Quercetagetin

Cas No. 90-18-6 SDF Download SDF
PubChem ID 5281680 Appearance Beige-yellow powder
Formula C15H10O8 M.Wt 318.23
Type of Compound Flavonoids Storage Desiccate at -20°C
Synonyms 3,3',4',5,6,7-Hexahydroxyflavone; 6-Hydroxyquercetin
Solubility DMSO : 125 mg/mL (392.79 mM; Need ultrasonic)
Chemical Name 2-(3,4-dihydroxyphenyl)-3,5,6,7-tetrahydroxychromen-4-one
SMILES C1=CC(=C(C=C1C2=C(C(=O)C3=C(C(=C(C=C3O2)O)O)O)O)O)O
Standard InChIKey ZVOLCUVKHLEPEV-UHFFFAOYSA-N
Standard InChI InChI=1S/C15H10O8/c16-6-2-1-5(3-7(6)17)15-14(22)13(21)10-9(23-15)4-8(18)11(19)12(10)20/h1-4,16-20,22H
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 Quercetagetin

1 Citrus sp. 2 Coronilla sp. 3 Tagetes sp.

Biological Activity of Quercetagetin

DescriptionQuercetagetin may be a potent inhibitor of the STAT1 signal, which could be a new molecular target for anti-inflammatory treatment, and may thus have therapeutic applications as an immune modulator in inflammatory diseases such as AD. It has stronger inhibitory effects on the protein and mRNA expression of TARC and MDC than other flavonoids.
TargetsTARC | MDC | STAT
In vitro

Anti-Inflammatory Effect of Quercetagetin, an Active Component of Immature Citrus unshiu, in HaCaT Human Keratinocytes.[Pubmed: 24009872 ]

Biomolecules and Therapeutics, 2013, 21(2):138-145.

Citrus fruit contain various flavonoids that have multiple biological activities. However, the content of these flavonoids are changed during maturation and immature Citrus is known to contain larger amounts than mature. Chemokines are significant mediators for cell migration, while thymus and activation-regulated chemokine (TARC/CCL17) and macrophage-derived chemokine (MDC/CCL22) are well known as the typical inflammatory chemokines in atopic dermatitis (AD), a pruritic and chronic inflammatory skin disease. We reported recently that the EtOH extract of immature Citrus unshiu inhibits TARC and MDC production.
METHODS AND RESULTS:
Therefore, we investigated the activity of flavonoids contained in immature Citrus on TARC and MDC levels. As a result, among the various flavonoids, Quercetagetin has stronger inhibitory effects on the protein and mRNA expression of TARC and MDC than other flavonoids. Quercetagetin particularly has better activity on TARC and MDC level than quercetin. In HPLC analysis, the standard peak of Quercetagetin matches the peaks of extract of immature C. unshiu.
CONCLUSIONS:
This suggests that Quercetagetin is an anti-inflammatory component in immature C. unshiu.

Protocol of Quercetagetin

Kinase Assay

Quercetagetin inhibits macrophage-derived chemokine in HaCaT human keratinocytes via the regulation of signal transducer and activator of transcription 1, suppressor of cytokine signalling 1 and transforming growth factor-β1.[Pubmed: 24602010 ]

Br J Dermatol. 2014 Sep;171(3):512-23.

Inflammatory chemokines, such as macrophage-derived chemokine (MDC/CCL22), are elevated in the serum and lesioned skin of patients with atopic dermatitis (AD), and are ligands for C-C chemokine receptor 4, which is predominantly expressed on T helper 2 lymphocytes, basophils and natural killer cells. We have previously reported that Quercetagetin has an inhibitory activity on inflammatory chemokines, which is induced by interferon (IFN)-γ and tumour necrosis factor (TNF)-α, occurring via inhibition of the signal transducer and activator of transcription 1 (STAT1) signal. To investigate the specific mechanisms of Quercetagetin on the STAT1 signal.
METHODS AND RESULTS:
We confirmed the inhibitory activity of Quercetagetin on MDC and STAT1 in HaCaT keratinocytes. The interaction between STAT1 and IFN-γR1 was investigated using immunoprecipitation. The small interfering RNA approach was used to investigate the role of suppressor of cytokine signalling 1 (SOCS1) and transforming growth factor (TGF)-β1 induced by Quercetagetin. Quercetagetin inhibited the expression of MDC at both the protein and mRNA levels in IFN-γ- and TNF-α-stimulated HaCaT human keratinocytes. Moreover, Quercetagetin inhibited the phosphorylation of STAT1 through upregulation of SOCS1. Increased expression of SOCS1 disrupted the binding of STAT1 to IFN-γR1. Furthermore, Quercetagetin augmented the expression of TGF-β1, which is known to modulate the immune response and inflammation.
CONCLUSIONS:
These results suggest that Quercetagetin may be a potent inhibitor of the STAT1 signal, which could be a new molecular target for anti-inflammatory treatment, and may thus have therapeutic applications as an immune modulator in inflammatory diseases such as AD.

Quercetagetin Dilution Calculator

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Preparing Stock Solutions of Quercetagetin

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.1424 mL 15.7119 mL 31.4238 mL 62.8476 mL 78.5595 mL
5 mM 0.6285 mL 3.1424 mL 6.2848 mL 12.5695 mL 15.7119 mL
10 mM 0.3142 mL 1.5712 mL 3.1424 mL 6.2848 mL 7.856 mL
50 mM 0.0628 mL 0.3142 mL 0.6285 mL 1.257 mL 1.5712 mL
100 mM 0.0314 mL 0.1571 mL 0.3142 mL 0.6285 mL 0.7856 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 Quercetagetin

Quercetagetin and Patuletin: Antiproliferative, Necrotic and Apoptotic Activity in Tumor Cell Lines.[Pubmed:30304821]

Molecules. 2018 Oct 9;23(10). pii: molecules23102579.

Quercetagetin and patuletin were extracted by the same method from two different Tagetes species that have multiple uses in folk medicine in Mexico and around the globe, one of which is as an anticancer agent. Their biological activity (IC50 and necrotic, apoptotic and selective activities of these flavonols) was evaluated and compared to that of quercetin, examining specifically the effects of C6 substitution among quercetin, Quercetagetin and patuletin. We find that the presence of a methoxyl group in C6 enhances their potency.

Quercetagetin-Loaded Composite Nanoparticles Based on Zein and Hyaluronic Acid: Formation, Characterization, and Physicochemical Stability.[Pubmed:29897751]

J Agric Food Chem. 2018 Jul 18;66(28):7441-7450.

Zein and hyaluronic acid (HA) composite nanoparticles were self-assembly fabricated using antisolvent coprecipitation (ASCP) method to deliver Quercetagetin (Que). FTIR, CD, and FS results revealed that electrostatic attraction, hydrogen bonding, and hydrophobic effect were the dominant driving forces among zein, Que, and HA. With the increasing of HA level, the morphological structure of zein-Que-HA complex was changed from nanoparticle (from 100:5:5 to 100:5:20) to microgel (from 100:5:25 to 100:5:30). The encapsulation efficiency of Que has significantly increased from 55.66% (zein-Que, 100:5) to 93.22% (zein-Que-HA, 100:5:20), and Que in the zein-Que-HA composite nanoparticles exhibited obviously enhanced photochemical, thermal, and physical stability. After 8 months of storage (4 degrees C), the retention rate of Que also up to 77.93%. These findings interpreted that zein-HA composite nanoparticle would be an efficient delivery system for encapsulating and protecting bioactive compounds.

High glucose promotes vascular smooth muscle cell proliferation by upregulating proto-oncogene serine/threonine-protein kinase Pim-1 expression.[Pubmed:29179437]

Oncotarget. 2017 Jul 18;8(51):88320-88331.

Serine/threonine kinase proviral integration site for Moloney murine leukemia virus 1 (Pim-1) plays an essential role in arterial wall cell proliferation and associated vascular diseases, including pulmonary arterial hypertension and aortic wall neointima formation. Here we tested a role of Pim-1 in high-glucose (HG)-mediated vascular smooth muscle cell (VSMC) proliferation. Pim-1 and proliferating cell nuclear antigen (PCNA) expression levels in arterial samples from streptozotocin-induced hyperglycemia rats were increased, compared with their weak expression in normoglycemic groups. In cultured rat VSMCs, HG led to transient Pim-1 expression decline, followed by sustained expression increase at both transcriptional and translational levels. Immunoblot analysis demonstrated that HG increased the expression of the 33-kDa isoform of Pim-1, but at much less extent to its 44-kDa plasma membrane isoform. D-glucose at a concentration of 25 mmol/L showed highest activity in stimulating Pim-1 expression. Both Pim-1 inhibitor Quercetagetin and STAT3 inhibitor stattic significantly attenuated HG-induced VSMC proliferation and arrested cell cycle progression at the G1 phase. Quercetagetin showed no effect on Pim-1 expression but decreased the phosphorylated-Bad (T112)/Bad ratio in HG-treated VSMCs. However, stattic decreased phosphorylated-STAT3 (Y705) levels and caused transcriptional and translational down-regulation of Pim-1 in HG-treated VSMCs. Our findings suggest HG-mediated Pim-1 expression contributes to VSMC proliferation, which may be partly due to the activation of STAT3/Pim-1 signaling.

Description

Quercetagetin (6-Hydroxyquercetin) is the major flavonoid isolated from Citrus unshiu (C. unshiu) peel. Quercetagetin is a moderately potent and selective, cell-permeable pim-1 kinase inhibitor (IC50, 0.34 μM). Anti-inflammatory and anticancer properties.

Keywords:

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