Miquelianin  (Synonyms: Quercetin 3-O-glucuronide; Quercetin 3-glucuronide)

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].

MCE has not independently confirmed the accuracy of these methods. They are for reference only.

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].

MCE has not independently confirmed the accuracy of these methods. They are for reference only.

478.36

Solid

C₂₁H₁₈O₁₃

22688-79-5

O=C1C2=C(O)C=C(O)C=C2OC(C3=CC=C(O)C(O)=C3)=C1O[[email protected]@H]4O[[email protected]](C(O)=O)[[email protected]@H](O)[[email protected]](O)[[email protected]]4O

Room temperature in continental US; may vary elsewhere.

• [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.  [Content Brief]

  [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.  [Content Brief]

  [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.  [Content Brief]

  [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.  [Content Brief]

  [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.  [Content Brief]