| Size | Price | Stock | Qty |
|---|---|---|---|
| 1mg |
|
||
| 5mg |
|
||
| 10mg |
|
||
| 100mg | |||
| Other Sizes |
| Targets |
Quercetin 3-gentiobioside targets aldose reductase (AR), advanced glycation end-product (AGE) formation, and aromatase. It inhibits aromatase with a Ki of 46.77 nM. The compound inhibits aldose reductase (AR) with an IC50 of 10.60 μM and inhibits the formation of advanced glycation end products (AGEs) with an IC50 of 109.46 μM. It also targets cancer cell proliferation pathways.
|
|---|---|
| ln Vitro |
In vitro, Quercetin 3-gentiobioside demonstrates potent inhibition of aldose reductase (IC50 = 10.60 μM), an enzyme involved in the polyol pathway implicated in diabetic complications. It also inhibits AGE formation (IC50 = 109.46 μM), reducing protein glycation and oxidative stress. It binds to human placental aromatase (PDB: 3EQM) with a binding affinity of -10 kcal/mol and an estimated Ki of 46.77 nM. The compound inhibits the proliferation of cancer cells and fibroblast-like synoviocytes.
|
| ln Vivo |
In vivo activity data for Quercetin 3-gentiobioside are limited. Based on its in vitro activities, the compound is expected to exhibit beneficial effects in models of diabetic complications (via AR inhibition) and cancer (via antiproliferative and aromatase inhibitory activities). Its antioxidant properties suggest potential systemic protective effects against oxidative stress. Further in vivo studies are needed to confirm these activities and establish pharmacokinetic and efficacy profiles.
|
| Enzyme Assay |
In vitro enzyme inhibition assays for Quercetin 3-gentiobioside are conducted using recombinant or purified aldose reductase enzyme. The enzyme is incubated with substrate (e.g., DL-glyceraldehyde or D-glucuronic acid) and NADPH in the presence of varying compound concentrations. Activity is measured spectrophotometrically by monitoring NADPH oxidation at 340 nm. AGE formation inhibition is assessed using a BSA-glucose glycation model, where fluorescence of AGEs is measured at excitation/emission of 370/440 nm. Aromatase inhibition is evaluated using human placental microsomes and radiolabeled androstenedione as substrate.
|
| Cell Assay |
Cellular assays for Quercetin 3-gentiobioside are performed using cancer cell lines such as A549 (lung carcinoma) and fibroblast-like synoviocytes. Cells are seeded in 96-well plates and treated with compound concentrations typically ranging from 1 to 200 μM for 24-72 hours. Cell viability is assessed using MTT or CCK-8 assays. Antiproliferative effects are quantified by measuring absorbance at 490 nm or 450 nm, and IC50 values are calculated from dose-response curves.
|
| Animal Protocol |
In vivo animal studies for Quercetin 3-gentiobioside have not been extensively reported. Based on its mechanism as an aldose reductase inhibitor, potential in vivo models include streptozotocin-induced diabetic rats to evaluate effects on polyol pathway activity and diabetic complications. For anticancer activity, xenograft mouse models bearing human lung carcinoma cells could be used. Standard protocols would involve oral or intraperitoneal administration with assessment of tumor growth, biomarkers, and organ toxicity.
|
| ADME/Pharmacokinetics |
Pharmacokinetic properties of Quercetin 3-gentiobioside are not well characterized. As a flavonoid glycoside with a molecular weight of 626.52, it is expected to have limited oral bioavailability due to poor membrane permeability and extensive first-pass metabolism. The gentiobioside moiety may be hydrolyzed by intestinal glycosidases, releasing the quercetin aglycone. Standard PK studies in rodents would be required to determine absorption, distribution, metabolism, and excretion parameters.
|
| Toxicity/Toxicokinetics |
Toxicological data for Quercetin 3-gentiobioside are limited. As a naturally occurring flavonoid glycoside, it is expected to have a favorable safety profile. No significant acute toxicity has been reported. The compound is designated for research use only. Standard toxicity screening would involve acute and sub-chronic oral toxicity studies in rodents, with histopathological evaluation of major organs and hematological analysis.
|
| References | |
| Additional Infomation |
Quercetin-3β-gentiobiose is a quercetin O-glycoside in which the hydroxyl hydrogen at the 3-position of quercetin is replaced by a gentiobiose group. It is a metabolite of Brassica napus. It is a quercetin O-glycoside, a disaccharide derivative, and a tetrahydroxyflavone. Its function is related to gentiobiose. Quercetin-3β-gentiobiose has been reported to be found in Phyllanthus virgatus, Fagonia glutinosa, and several other organisms with relevant data.
Quercetin 3-gentiobioside is a flavonoid isolated from Artemisia iwayomogi that inhibits aldose reductase (IC50 = 10.60 μM), AGE formation (IC50 = 109.46 μM), and aromatase (Ki = 46.77 nM). It exhibits antiproliferative activity against cancer cells and synoviocytes. Its unique quercetin-gentiobioside structure enhances solubility compared to the aglycone. The compound is not approved for clinical use and is utilized as a research tool for diabetes, cancer, and inflammation studies. |
| Molecular Formula |
C27H30O17
|
|---|---|
| Molecular Weight |
626.5169
|
| Exact Mass |
626.148
|
| CAS # |
7431-83-6
|
| PubChem CID |
5320834
|
| Appearance |
Light yellow to yellow solid powder
|
| Density |
1.9±0.1 g/cm3
|
| Boiling Point |
1033.2±65.0 °C at 760 mmHg
|
| Flash Point |
340.6±27.8 °C
|
| Vapour Pressure |
0.0±0.3 mmHg at 25°C
|
| Index of Refraction |
1.785
|
| LogP |
-0.73
|
| Hydrogen Bond Donor Count |
11
|
| Hydrogen Bond Acceptor Count |
17
|
| Rotatable Bond Count |
7
|
| Heavy Atom Count |
44
|
| Complexity |
1040
|
| Defined Atom Stereocenter Count |
10
|
| 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)CO[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)O)O)O)O)O
|
| InChi Key |
FDRQPMVGJOQVTL-DEFKTLOSSA-N
|
| InChi Code |
InChI=1S/C27H30O17/c28-6-14-17(33)20(36)22(38)26(42-14)40-7-15-18(34)21(37)23(39)27(43-15)44-25-19(35)16-12(32)4-9(29)5-13(16)41-24(25)8-1-2-10(30)11(31)3-8/h1-5,14-15,17-18,20-23,26-34,36-39H,6-7H2/t14-,15-,17-,18-,20+,21+,22-,23-,26-,27+/m1/s1
|
| Chemical Name |
2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one
|
| 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 Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture and light. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
|
| Solubility (In Vitro) |
DMSO : ~100 mg/mL (~159.61 mM)
|
|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (3.99 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 (3.99 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. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 1.5961 mL | 7.9806 mL | 15.9612 mL | |
| 5 mM | 0.3192 mL | 1.5961 mL | 3.1922 mL | |
| 10 mM | 0.1596 mL | 0.7981 mL | 1.5961 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.
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.
Products are for research use only; We do not sell to patients
Copyright 2020 InvivoChem LLC | All Rights Reserved
