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22688-79-5

22688-79-5 structure
22688-79-5 structure
Name miquelianin
Synonyms 4H-1-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-3-(β-D-glucopyranuronosyloxy)-5,7-dihydroxy-
Querciturone
Quercetin-3-O-glucuronide
Quercetin-3-O-β-D-glucuronopyranoside
Miquelianin
quercetin 3-O-glucuronide
Quercetin 3-O-β-D-glucuronide
Quercetin-3-Glucuronide
2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl β-D-glucopyranosiduronic acid
Quercetin 3-glucuronide
Miquelianin (Quercetin 3-O-glucuronide)
Description Miquelianin (Quercetin 3-O-glucuronide) is a metabolite of quercetin and a type of natural flavonoid.
Related Catalog
In Vitro 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].
In Vivo 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].
Animal Admin 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.

[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 β₂-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.

Density 2.0±0.1 g/cm3
Boiling Point 927.8±65.0 °C at 760 mmHg
Molecular Formula C21H18O13
Molecular Weight 478.360
Flash Point 325.8±27.8 °C
Exact Mass 478.074738
PSA 227.58000
LogP 2.10
Vapour Pressure 0.0±0.3 mmHg at 25°C
Index of Refraction 1.819
Storage condition ?20°C
Safety Phrases 24/25
RIDADR NONH for all modes of transport
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title: CAS No. 22688-79-5 | Chemsrc address: https://m.chemsrc.com/en/baike/665017.html

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