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) |
Biological Activity
| 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). |
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. 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 |