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Miquelianin

Alias: Quercituron Mikwelianin Miquelianin
Cat No.:V21760 Purity: ≥98%
Miquelianin (Quercetin 3-O-glucuronide) is a metabolite of quercetin and a naturally occurring flavonoid.
Miquelianin
Miquelianin Chemical Structure CAS No.: 22688-79-5
Product category: Endogenous Metabolite
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
Miquelianin (Quercetin 3-O-glucuronide) is a metabolite of quercetin and a naturally occurring flavonoid.
Biological Activity I Assay Protocols (From Reference)
ln Vitro
In human plasma, mequelianin demonstrates antioxidant properties. The consumption of three antioxidants, lycopene, β-carotene, and α-tocopherol, is considerably inhibited by miquelianin at 50 μM [1]. Miquelianin can go from the small intestine to the central nervous system, according to in vitro research [2]. Miquelianin dramatically lowers the synthesis of beta-amyloid (Aβ) peptides in primary neuronal cells derived from the AD animal model Tg2576. Additionally, it possesses the ability to disrupt the preliminary protein-protein interaction between Aβ1-40 and Aβ1-42, which is necessary for the development of neurotoxic oligomeric Aβ species [3]. ROS production, cAMP and RAS activation, ERK1/2 phosphorylation, and the expression of the HMOX1, MMP2, and MMP9 genes were all reduced by treatment with 0.1 μM miquelianin. Miquelianin prevents [3H]-NA from binding to b2-AR and prevents MDA-MB-231 breast cancer cells from invading and inducing MMP-9. Miquelianin may be a dietary chemopreventive factor in stress-related breast cancer and may decrease breast cancer cell invasion by regulating b2-adrenergic signaling [4].
ln Vivo
When compared to vehicle control treatment, meiquelianin administration dramatically repaired AD-type impairments in basal synaptic transmission and long-term potentiation in the hippocampus formation [3].
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]. 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]. Flavonoids from Hypericum perforatum show antidepressant activity in the forced swimming test. Planta Med. 2000 Feb;66(1):3-6.

[4]. 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]. 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.

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

Additional Infomation
Miquelianin is a quercetin O-glycoside that consists of quercetin attached to a beta-D-glucuronopyranosyl moiety at position 3 via a glycosidic linkage. Isolated from Salvia and Phaseolus vulgaris, it exhibits antioxidant and antidepressant activities. It has a role as a metabolite, an antioxidant and an antidepressant. It is a beta-D-glucosiduronic acid and a quercetin O-glycoside.
quercetin 3-O-glucuronide has been reported in Callistemon citrinus, Myrothamnus flabellifolia, and other organisms with data available.
See also: Bilberry (part of); Theobroma grandiflorum seed (part of).
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C21H18O13
Molecular Weight
478.362
Exact Mass
478.074
CAS #
22688-79-5
PubChem CID
5274585
Appearance
Light yellow to yellow solid powder
Density
2.0±0.1 g/cm3
Boiling Point
927.8±65.0 °C at 760 mmHg
Flash Point
325.8±27.8 °C
Vapour Pressure
0.0±0.3 mmHg at 25°C
Index of Refraction
1.819
LogP
2.1
Hydrogen Bond Donor Count
8
Hydrogen Bond Acceptor Count
13
Rotatable Bond Count
4
Heavy Atom Count
34
Complexity
830
Defined Atom Stereocenter Count
5
SMILES
C1=CC(=C(C=C1C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)C(=O)O)O)O)O)O)O
InChi Key
DUBCCGAQYVUYEU-ZUGPOPFOSA-N
InChi Code
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
Chemical Name
(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
Synonyms
Quercituron Mikwelianin Miquelianin
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO : ≥ 30 mg/mL (~62.71 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (5.23 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.5 mg/mL (5.23 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 2.5 mg/mL (5.23 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 2.0905 mL 10.4524 mL 20.9048 mL
5 mM 0.4181 mL 2.0905 mL 4.1810 mL
10 mM 0.2090 mL 1.0452 mL 2.0905 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

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