Miquelianin

• CAT Number: R054816
• CAS Number: 22688-79-5
• Molecular Formula: C21H18O13
• Molecular Weight: 478.36
• Purity: ≥95%
• Synonyms: (2S,3S,4S,5R,6S)-6-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid
• InChI: InChI=1S/C21H18O13/c22-7-4-10(25)12-11(5-7)32-17(6-1-2-8(23)9(24)3-6)18(13(12)26)33-21-16(29)14(27)15(28)19(34-21)20(30)31/h1-5,14-16,19,21-25,27-29H,(H,30,31)/t14-,15-,16+,19-,21+/m0/s1
• InChIKey: DUBCCGAQYVUYEU-ZUGPOPFOSA-N
• SMILES: C1=CC(=C(C=C1C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)OC4C(C(C(C(O4)C(=O)O)O)O)O)O)O

Miquelianin (Quercetin 3-O-glucuronide) is a metabolite of quercetin and a type of natural flavonoid. Miquelianin is also a CBR1 inhibitor.
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].

Reference

[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]

[6]. Iannuzzi A M, et al. Chemical profile and nutraceutical features of Salsola soda (agretti): Anti-inflammatory and antidiabetic potential of its flavonoids[J]. Food Bioscience, 2020, 37: 100713.