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Quercetin-7-O-beta-D-glucopyranoside

Alias: Quercimeritrin
Cat No.:V34294 Purity: ≥98%
Quercimeritrin is extracted from Trichosanthes aeruginosa and has significant amylase activity.
Quercetin-7-O-beta-D-glucopyranoside
Quercetin-7-O-beta-D-glucopyranoside Chemical Structure CAS No.: 491-50-9
Product category: Plants
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
Quercimeritrin is extracted from Trichosanthes aeruginosa and has significant amylase activity.
Quercetin-7-O-beta-D-glucopyranoside (quercimeritrin) is a known flavonoid compound isolated from the leaves of Ixeridium dentatum together with other sesquiterpene lactones and phenylethanoids. In this study, it was evaluated for its amylase secretion activity in human salivary gland (HSG) cells under high glucose conditions, as part of a search for potential regulators of salivary secretion to alleviate xerostomia (dry mouth). [1]
Biological Activity I Assay Protocols (From Reference)
Targets
Amylase secretion activity in human salivary gland cells. [1]
ln Vitro
Quercetin-7-O-beta-D-glucopyranoside (compound 11) was tested for its ability to modulate amylase secretion in human salivary gland (HSG) cells treated with 40 mM high glucose. All isolated compounds (1–13) increased amylase secretion activity and reversed the reduction caused by high glucose, except compound 3. Quercetin-7-O-beta-D-glucopyranoside exhibited one of the most potent amylase secretion activities, comparable to the positive control (8-epiisopildiol-3-O-β-D-glucopyranoside). No quantitative values (e.g., EC50, fold increase) were provided. [1]
Cell Assay
The amylase secretion activity of Quercetin-7-O-beta-D-glucopyranoside was evaluated in human salivary gland (HSG) cells. Cells were treated with high glucose (40 mM) to induce a reduction in amylase secretion, mimicking xerostomia-like conditions. After treatment with the test compounds, amylase activity in the culture supernatant was determined by measuring the levels of nitrophenol, a chromogenic product hydrolyzed by α-amylase. This method is described as a simple, direct kinetic assay for salivary α-amylase. Quercetin-7-O-beta-D-glucopyranoside (compound 11) significantly increased amylase secretion, reversing the inhibitory effect of high glucose, and its potency was comparable to that of the positive control 8-epiisopildiol-3-O-β-D-glucopyranoside. [1]
References

[1]. Centaurea mersinensis phytochemical composition and multi-dimensional bioactivity properties supported by molecular modeling[J]. Journal of Biomolecular Structure and Dynamics, 2024, 42(5): 2341-2357.

[2]. Inhibitory Mechanism of Quercimeritrin as a Novel α-Glucosidase Selective Inhibitor. Foods. 2023;12(18):3415. Published 2023 Sep 13.

[3]. Anti-angiogenic activity of quercetin and its derivatives[J]. Letters in Drug Design & Discovery, 2004, 1(4): 329-333.

[4]. Isolation of amylase regulators from the leaves of Ixeridium dentatum. Nat Prod Res. 2019 Apr 10:1-6.

Additional Infomation
Quercetin 7-O-β-D-glucoside is a quercetin O-glucoside in which a glucosyl residue is linked to the 7-position of quercetin via a β-glycosidic bond. It possesses antioxidant and metabolic activities. It is a β-D-glucoside, monosaccharide derivative, flavonol compound, tetrahydroxyflavone, and quercetin O-glucoside. Quercetin glycosides have been reported in camellia (Camellia sinensis), spring roll (Spiranthes vernalis), and several other organisms with relevant data. See also: Chamomile (partial).
Quercetin-7-O-beta-D-glucopyranoside (quercimeritrin) was isolated from the leaves of Ixeridium dentatum as one of eleven known compounds. The study aimed to develop I. dentatum as a supplement for dry mouth (xerostomia). Previous research from the same group showed that other sesquiterpene lactones from the roots of I. dentatum (e.g., 8-epiisolipidiol-3-O-β-D-glucopyranoside and ixerin F) were useful to prevent and treat xerostomia. The current study extends this investigation to the leaves, and Quercetin-7-O-beta-D-glucopyranoside was identified as one of the active amylase regulators. [1]
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C21H20O12
Molecular Weight
464.3763
Exact Mass
464.095
CAS #
491-50-9
PubChem CID
5282160
Appearance
White to yellow solid
Density
1.8±0.1 g/cm3
Boiling Point
859.2±65.0 °C at 760 mmHg
Flash Point
302.8±27.8 °C
Vapour Pressure
0.0±0.3 mmHg at 25°C
Index of Refraction
1.775
LogP
-0.17
Hydrogen Bond Donor Count
8
Hydrogen Bond Acceptor Count
12
Rotatable Bond Count
4
Heavy Atom Count
33
Complexity
758
Defined Atom Stereocenter Count
5
SMILES
O1[C@]([H])([C@@]([H])([C@]([H])([C@@]([H])([C@@]1([H])C([H])([H])O[H])O[H])O[H])O[H])OC1=C([H])C(=C2C(C(=C(C3C([H])=C([H])C(=C(C=3[H])O[H])O[H])OC2=C1[H])O[H])=O)O[H]
InChi Key
BBFYUPYFXSSMNV-HMGRVEAOSA-N
InChi Code
InChI=1S/C21H20O12/c22-6-13-15(26)17(28)19(30)21(33-13)31-8-4-11(25)14-12(5-8)32-20(18(29)16(14)27)7-1-2-9(23)10(24)3-7/h1-5,13,15,17,19,21-26,28-30H,6H2/t13-,15-,17+,19-,21-/m1/s1
Chemical Name
2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
Synonyms
Quercimeritrin
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: This product requires protection from light (avoid light exposure) during transportation and storage.
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 : ~33.33 mg/mL (~71.77 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (5.38 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 (5.38 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 2.1534 mL 10.7670 mL 21.5341 mL
5 mM 0.4307 mL 2.1534 mL 4.3068 mL
10 mM 0.2153 mL 1.0767 mL 2.1534 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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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.
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