QuercetagetinCAS# 90-18-6 |
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| 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. |
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| 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. |
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| 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. | ||
| Description | 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. It has stronger inhibitory effects on the protein and mRNA expression of TARC and MDC than other flavonoids. |
| Targets | TARC | 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. |
| 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.
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Quercetagetin Dilution Calculator
Quercetagetin Molarity Calculator
| 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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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.
