Quercetin 3-O-glucuronide (Synonyms: Miquelianin, Quercetin 3-O-β-Dglucuronide) |
| Catalog No.GC44795 |
La quercétine 3-O-glucuronide (Quercetin 3-O-glucuronide) est un métabolite de la quercétine et un type de flavonoÏde naturel.
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Cas No.: 22688-79-5
Sample solution is provided at 25 µL, 10mM.
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Miquelianin (Quercetin 3-O-glucuronide) is a metabolite of quercetin and a type of natural flavonoid.
Miquelianin shows an antioxidant effect in human plasma. At 50 μM, miquelianin suppresses the consumption of the three antioxidants lycopene, β-carotene and α-tocopherol significantly[1]. In vitro studies indicate that miquelianin is able to reach the central nervous system from the small intestine[2]. Miquelianin significantly reduces the generation of β-amyloid (Aβ) peptides by primary neuron cultures generated from the Tg2576 AD mouse model. It is also capable of interfering with the initial protein-protein interaction of Aβ1–40 and Aβ1–42 that is necessary for the formation of neurotoxic oligomeric Aβ species[3]. Treatment with 0.1 μM miquelianin suppresses ROS generation, cAMP and RAS activation, phosphorylation of ERK1/2 and the expression of HMOX1, MMP2, and MMP9 genes. Miquelianin suppresses invasion of MDA-MB-231 breast cancer cells and MMP-9 induction, and inhibits the binding of [3H]-NA to b2-AR. Miquelianin may function to suppress invasion of breast cancer cells by controlling b2-adrenergic signaling, and may be a dietary chemopreventive factor for stress-related breast cancer[4].
Miquelianin treatment, compared to vehicle-control treatment, significantly improves AD-type deficits in hippocampal formation basal synaptic transmission and long-term potentiation[3]. A flavonoid fraction obtained from a crude extract of Hypericum perforatum (St. John's wort) is remarkably active in the forced swimming test. Miquelianin is one of the compound separated from the fraction[5].
References:
[1]. Terao J, e al. Protection by quercetin and quercetin 3-O-beta-D-glucuronide of peroxynitrite-induced antioxidant consumption in human plasma low-density lipoprotein. Free Radic Res. 2001 Dec;35(6):925-31.
[2]. Juergenliemk G, et al. In vitro studies indicate that miquelianin (quercetin 3-O-beta-D-glucuronopyranoside) is able to reach the CNS from the small intestine. Planta Med. 2003 Nov;69(11):1013-7.
[3]. Butterweck V, et al. Flavonoids from Hypericum perforatum show antidepressant activity in the forced swimming test. Planta Med. 2000 Feb;66(1):3-6.
[4]. Yamazaki S, et al. Quercetin-3-O-glucuronide inhibits noradrenaline-promoted invasion of MDA-MB-231 human breast cancer cells by blocking β -adrenergic signaling. Arch Biochem Biophys. 2014 Sep 1;557:18-27.
[5]. Ho L, et al. Identification of brain-targeted bioactive dietary quercetin-3-O-glucuronide as a novel intervention for Alzheimer's disease. FASEB J. 2013 Feb;27(2):769-81.
Animal experiment: | Rats: Miquelianin is administered orally using the gavage techniques. The rats are treated with 0.6 mg/kg miquelianin for 12 days. Antidepressant activity is performed using the Forced Swimming Test[5]. |
References: [1]. Terao J, e al. Protection by quercetin and quercetin 3-O-beta-D-glucuronide of peroxynitrite-induced antioxidant consumption in human plasma low-density lipoprotein. Free Radic Res. 2001 Dec;35(6):925-31. | |
| Cas No. | 22688-79-5 | SDF | |
| Synonymes | Miquelianin, Quercetin 3-O-β-Dglucuronide | ||
| Canonical SMILES | OC1=CC(O)=C(C(C(O[C@H]2[C@H](O)[C@@H](O)[C@H](O)[C@@H](C(O)=O)O2)=C(C3=CC=C(O)C(O)=C3)O4)=O)C4=C1 | ||
| Formula | C21H18O13 | M.Wt | 478.4 |
| Solubility | DMF: 30 mg/ml,DMSO: 20 mg/ml,Ethanol: 10 mg/ml,PBS (pH 7.2): 2 mg/ml | Storage | Store at 2-8°C |
| General tips | Please select the appropriate solvent to prepare the stock solution according to the
solubility of the product in different solvents; once the solution is prepared, please store it in
separate packages to avoid product failure caused by repeated freezing and thawing.Storage method
and period of the stock solution: When stored at -80°C, please use it within 6 months; when stored
at -20°C, please use it within 1 month. To increase solubility, heat the tube to 37°C and then oscillate in an ultrasonic bath for some time. |
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| Shipping Condition | Evaluation sample solution: shipped with blue ice. All other sizes available: with RT, or with Blue Ice upon request. | ||
| Prepare stock solution | |||
|
1 mg | 5 mg | 10 mg |
| 1 mM | 2.0903 mL | 10.4515 mL | 20.903 mL |
| 5 mM | 0.4181 mL | 2.0903 mL | 4.1806 mL |
| 10 mM | 0.209 mL | 1.0452 mL | 2.0903 mL |
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Quality Control & SDS
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- Purity: >99.50%
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Average Rating: 5 (Based on Reviews and 23 reference(s) in Google Scholar.)
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