Miquelianin (Quercetin 3-O-glucuronide) chemical structure
Chemical structureResearch use only
CAT. NO. DC10152Featured

Miquelianin (Quercetin 3-O-glucuronide)

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Product overview

Description & Application

Miquelianin (Quercetin 3-O-glucuronide) is a metabolite of quercetin and a type of natural flavonoid.

ParameterValue
Chemical NameMiquelianin
CAS No.22688-79-5
Synonymsb-D-Glucopyranosiduronic acid,2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-1-benzopyran-3-yl;Quercetin 3-glucuronide;Quercetin 3-O-β-D-Glucuronide;Quercetin 7-O-β-D-Gl;QUERCETIN-3-O-GLUCURONIDE;QUERCETIN-3-O-GLUCURONIDE(RG);Quercituron;Quercetin 3-O-glucuronide;3,3′,4′,5,7-Pentahydroxyflavone 3-glucuronide;Mikwelianin;Miquelianin;Querciturone;Quercetol 3-O-glucuronide;Quercetol glucuronide;quercetin 3-O-;A-D-glucuronopyranoside;MLS000563480;Quercetin 3-O-b-D-glucuronide;HMS2223E09;SMR000232284;Quercetin-3-glucuronideQUERCETIN GLUCURONIDE
FormulaC21H18O13
M.Wt478.3598
SMILESO1C([H])(C(=O)O[H])C([H])(C([H])(C([H])(C1([H])OC1C(C2=C(C([H])=C(C([H])=C2OC=1C1C([H])=C([H])C(=C(C=1[H])O[H])O[H])O[H])O[H])=O)O[H])O[H])O[H]
Purity>98%
Storage2 years -20°C Powder, 2 weeks 4°C in DMSO, 6 months -80°C in DMSO

Biological Activity

Miquelianin (Quercetin 3-O-glucuronide) is a metabolite of quercetin and a type of natural flavonoid.

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].

References & source

DC Chemicals original product information

Published experimental findings depend on the model and assay conditions. They do not guarantee equivalent performance in every application. For laboratory research use only.

Product documentation

Refer to the certificate supplied with your lot for batch-specific release results.

Handling guide

2 years -20°C Powder, 2 weeks 4°C in DMSO, 6 months -80°C in DMSO

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