Quercetol glucuronide
Quercetin-3-O-glucuronide
CAS: 22688-79-5
Molecular Formula: C21H18O13
Quercetol glucuronide - Names and Identifiers
Quercetol glucuronide - Physico-chemical Properties
| Molecular Formula | C21H18O13 |
| Molar Mass | 478.4 |
| Density | 1.96±0.1 g/cm3(Predicted) |
| Melting Point | 193～195℃ |
| Boling Point | 927.8℃ at 760 mmHg |
| Solubility | DMSO (Slightly), Methanol (Slightly) |
| Appearance | Yellow powder |
| Color | Yellow to Very Dark Yellow |
| pKa | 2.76±0.70(Predicted) |
| Storage Condition | 2-8℃ |
| Stability | Very Hygroscopic |
| Physical and Chemical Properties | Chemical properties of brown crystalline powder, soluble in methanol, ethanol, DMSO and other organic solvents, derived from the white leaf, Bar Board, spring bupleurum. |
| Use | Uses antioxidant, anti-atherosclerotic effects. For content determination/identification/pharmacological experiments |
Quercetol glucuronide - Risk and Safety
| Safety Description | 24/25 - Avoid contact with skin and eyes. |
| WGK Germany | 3 |
Quercetol glucuronide - Reference
| Reference Show more | 1. Min Li, Zhi-Ying Du, Xin Chai, et al. Effect of processing on flavonoids in fennel [J]. Tianjin traditional Chinese medicine, 2019, 036(006):612-614. 2. Yang, Jing, et al. "Determination of active compounds in raspberry leaf extracts and the effects of extract takes on mice." Food Science and Technology 40 (2019): 124-131.https:// doi.org/10.1590/fst.35518 3. Cao, Yanni, et al. "Chemical fingerprint and multicomponent quantitative analysis for the quality evaluation of Cyclocarya paliurus leaves by HPLC-Q-TOF-MS." Molecules 22.11 (2017): 1927.https://doi.org/10.3390/molecules22111927 4. Yang, Jing, et al. "Comparisons of the active components in four unripe raspberry extracts and their activites." Food Science and Technology 39 (2019): 632-639.https://doi.org/10.1590/fst.27418 5. [IF=4.411] Yanni Cao et al."Chemical Fingerprint and Multicomponent Quantitative Analysis for the Quality Evaluation of Cyclocarya paliurus Leaves by HPLC-Q-TOF-MS."Molecules. 2017 Nov;22(11):1927 6. [IF=3.205] Yuanyuan Li et al."Separation and purification of polyphenols from red wine extracts using high speed counter current chromatography."J Chromatogr B. 2017 Jun;1054:105 7. [IF=5.396] Xie Xing et al."Investigation into the mechanisms of quercetin-3-O-glucuronide inhibiting α-glucosidase activity and non-enzymatic glycation by spectroscopy and molecular docking."Food Funct. 2021 Aug;12(17):7825-7835 8. [IF=5.279] Yanan Gao et al."Galactosylation of Monosaccharide Derivatives of Glycyrrhetinic Acid by UDP-Glycosyltransferase GmSGT2 from Glycine max."J Agr Food Chem. 2020;68(32):8580-8588 9. [IF=4.952] Yuxin Hao et al."Stability and mechanism of phenolic compounds from raspberry extract under in vitro gastrointestinal digestion."Lwt Food Sci Technol. 2021 Mar;139:110552 10. [IF=4.24] Nana Li et al."Characterization of phenolic compounds and anti-acetylcholinase activity of coconut shells."Food Biosci. 2021 Aug;42:101204 11. [IF=4.162] Rong Wang et al."Total Flavone of Abelmoschus manihot Ameliorates Stress-Induced Microbial Alterations Drive Intestinal Barrier Injury in DSS Colitis."Drug Des Dev Ther. 2021; 15: 2999-3016 12. [IF=2.72] Ji-Yu Nie et al."Antioxidant activity evaluation of rosemary ethanol extract and their cellular antioxidant activity toward HeLa cells."J Food Biochem. 2019 Jul;43(7):e12851 13. [IF=2.633] Yanni Cao et al."Seasonal Variation in Phenolic Compounds and Antioxidant Activity in Leaves of Cyclocarya paliurus (Batal.) Iljinskaja."Forests. 2019 Aug;10(8):624 14. [IF=4.952] Shanshan Shen et al.Untargeted and targeted metabolomics reveals potential marker compounds of an tea during storage.Lwt Food Sci Technol. 2022 Jan;154:112791 15. [IF=7.514] YueTong Yu et al."Identification and Quantification of Oligomeric Proanthocyanidins Alkaloids, and Flavonoids in Lotus Seeds: A Potentially Rich Source of Bioactive Compounds."Food Chem. 2022 Jan;:132124 |
Quercetol glucuronide - Uses and methods of synthesis
Introduction
quercetin 3-o-glucoside is a kind of flavonoid, which exists in spring bupleurum, and spring Bupleurum is the whole grass of Bupleurum scorzonerifolium collected in spring in Jiangsu and part of Anhui.
preparation
an overnight culture of E. Coli containing a specific gene was inoculated into 50ml of fresh LB medium containing the appropriate antibiotics. Isopropyl β-D-1-thiogalactopyranoside (IPTG) was added to the mixture at a final concentration of 1mm. The transformants were further cultured at 18°C for 20 hours. Cells were harvested by centrifugation and resuspended in fresh M9 medium containing 2% glucose and antibiotics and 1mm isopropylβ-d-1-thiogalactoside. The cell density was adjusted to an OD600 value of 2. A total reaction volume of 2ml was maintained in a tube (14mm x 145mm). One hundred micromolar of luteolin was added to the reaction mixture. The mixture was incubated at 25°C for 1.5 hours. Additional 100 μm luteolin was added to the reaction mixture. The mixture was incubated for an additional 1.5 hours. 200 μm luteolin was added to the mixture to determine the optimal cell concentration. After 2 hours, 200 μm luteolin was added to the mixture. The reaction mixture was incubated for 2 hours. The cell density was adjusted to an OD600 value of 3. The reaction was carried out for 2 hours after the addition of 200 μm of quercetin. One hundred micromoles of quercetin were added to the mixture. The mixture was shaken at 30°C for 1.5 hours to obtain 2-(3,4 dihydroxyphenyl)-5, 7-dihydroxy-4-oxo-4h-1-benzopyran-3-yl-BETA-D-glucopyranosic acid
biological activity
Miquelianin (Quercetin 3-o-glucuronate) is a metabolite of Quercetin and a natural flavonoid.
Target
Human Endogenous Metabolite
in vitro studies
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. In vitro studies indicate that miquelianin is able to reach the central nervous system from the small intestine. 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. 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 [3 H]-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.
in vivo studies
Miquelianin treatment, compared to vehicle-control treatment, significantly improves AD-type deficits in hippocampal formation basal synaptic transmission and long-term potentiation. 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.
Last Update：2024-04-09 21:54:55
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