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Oxyresveratrol 2-O-beta-D-glucopyranoside

CAS# 392274-22-5

Oxyresveratrol 2-O-beta-D-glucopyranoside

Catalog No. BCN1448----Order now to get a substantial discount!

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Oxyresveratrol 2-O-beta-D-glucopyranoside: 5mg $265 In Stock
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Oxyresveratrol 2-O-beta-D-glucopyranoside: 500mg Please Inquire Please Inquire
Oxyresveratrol 2-O-beta-D-glucopyranoside: 1000mg Please Inquire Please Inquire

Quality Control of Oxyresveratrol 2-O-beta-D-glucopyranoside

Number of papers citing our products

Chemical structure

Oxyresveratrol 2-O-beta-D-glucopyranoside

3D structure

Chemical Properties of Oxyresveratrol 2-O-beta-D-glucopyranoside

Cas No. 392274-22-5 SDF Download SDF
PubChem ID 11058597 Appearance Powder
Formula C20H22O9 M.Wt 406.4
Type of Compound Phenols Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name (2S,3R,4S,5S,6R)-2-[2-[(E)-2-(3,5-dihydroxyphenyl)ethenyl]-5-hydroxyphenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
SMILES C1=CC(=C(C=C1O)OC2C(C(C(C(O2)CO)O)O)O)C=CC3=CC(=CC(=C3)O)O
Standard InChIKey UPUMEBJDZQEUFC-CUYWLFDKSA-N
Standard InChI InChI=1S/C20H22O9/c21-9-16-17(25)18(26)19(27)20(29-16)28-15-8-12(22)4-3-11(15)2-1-10-5-13(23)7-14(24)6-10/h1-8,16-27H,9H2/b2-1+/t16-,17-,18+,19-,20-/m1/s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of Oxyresveratrol 2-O-beta-D-glucopyranoside

The root barks of Morus alba L.

Biological Activity of Oxyresveratrol 2-O-beta-D-glucopyranoside

DescriptionOxyresveratrol-2-O-beta-D-glucopyranoside shows better tyrosinase inhibitory activities than kojic acid.
TargetsNO | Tyrosinase
In vitro

Inhibitory effects of constituents from Morus alba var. multicaulis on differentiation of 3T3-L1 cells and nitric oxide production in RAW264.7 cells.[Pubmed: 21772233]

Molecules. 2011 Jul 19;16(7):6010-22. doi: 10.3390/molecules16076010.


METHODS AND RESULTS:
A new arylbenzofuran, 3',5'-dihydroxy-6-methoxy-7-prenyl-2-arylbenzofuran (1), and 25 known compounds, including moracin R (2), moracin C (3), moracin O (4), moracin P (5), artoindonesianin O (6), moracin D (7), alabafuran A (8), mulberrofuran L (9), mulberrofuran Y (10), kuwanon A (11), kuwanon C (12), kuwanon T (13), morusin (14), kuwanon E (15), sanggenon F (16), betulinic acid (17), uvaol (18), ursolic acid (19), β-sitosterol (20), oxyresveratrol 2-O-β-D-glucopyranoside (21), mulberroside A (22), mulberroside B (23), 5,7-dihydroxycoumarin 7-O-β-D-glucopyranoside (24), 5,7-dihydroxycoumarin 7-O-β-D-apiofuranosyl-(1→6)-O-β-D-glucopyranoside (25) and adenosine (26), were isolated from Morus alba var. multicaulis Perro. (Moraceae). Their structures were determined by spectroscopic methods. The prenyl-flavonoids 11-14, 16, triterpenoids 17,18 and 20 showed significant inhibitory activity towards the differentiation of 3T3-L1 adipocytes.
CONCLUSIONS:
The arylbenzofurans 1-10 and prenyl-flavonoids 11-16 also showed significant nitric oxide (NO) production inhibitory effects in RAW264.7 cells.

In vivo

Three major metabolites of mulberroside A in rat intestinal contents and feces.[Pubmed: 19787570]

Three major metabolites of mulberroside A in rat intestinal contents and feces.

Mulberroside A, a major stilbene constituent of MORUS ALBA L. (Moraceae), displays significant antitussive and antiasthmatic effects in animals.
METHODS AND RESULTS:
As part of our ongoing research on its biotransformation in rats, mulberroside A was orally administered to rats, and the metabolites in the gastrointestinal contents and feces were investigated. Three major metabolites were isolated from the feces of rats and identified as oxyresveratrol-2- O- beta- D-glucopyranoside ( 1), oxyresveratrol-3'- O- beta- D-glucopyranoside ( 2), and oxyresveratrol ( 3) on the basis of chemical and spectroscopic evidence. The three metabolites were also detected in the small intestinal contents of rats following oral administration of mulberroside A.
CONCLUSIONS:
These findings suggest that mulberroside A is metabolized prior to absorption into the body.

Protocol of Oxyresveratrol 2-O-beta-D-glucopyranoside

Kinase Assay

Tyrosinase inhibitory constituents from the roots of Morus nigra: a structure-activity relationship study.[Pubmed: 20297841]

J Agric Food Chem. 2010 May 12;58(9):5368-73. doi: 10.1021/jf1003607.

The phytochemical profiles of Morus nigra roots and twigs were compared by HPLC with those of the old and young twigs of Morus alba which are known to contain oxyresveratrol and mulberroside A as major components. It was found that M. nigra root extract contains some unknown natural products with potential tyrosinase inhibitory activity.
METHODS AND RESULTS:
The extract (95% ethanol) of the roots of M. nigra was further investigated in this study. One new compound, 5'-geranyl-5,7,2',4'-tetrahydroxyflavone, and twenty-eight known phenolic compounds were isolated. Their structures were identified by mass spectrometry and NMR spectroscopy. Nine compounds, 5'-geranyl-5,7,2',4'-tetrahydroxyflavone, steppogenin-7-O-beta-D-glucoside, 2,4,2',4'-tetrahydroxychalcone, moracin N, kuwanon H, mulberrofuran G, morachalcone A, oxyresveratrol-3'-O-beta-D-glucopyranoside and oxyresveratrol-2-O-beta-D-glucopyranoside, showed better tyrosinase inhibitory activities than kojic acid.
CONCLUSIONS:
It was noteworthy that the IC(50) values of 2,4,2',4'-tetrahydroxychalcone and morachalcone A were 757-fold and 328-fold lower than that of kojic acid, respectively, suggesting a great potential for their development as effective natural tyrosinase inhibitors.

Oxyresveratrol 2-O-beta-D-glucopyranoside Dilution Calculator

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Oxyresveratrol 2-O-beta-D-glucopyranoside Molarity Calculator

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Preparing Stock Solutions of Oxyresveratrol 2-O-beta-D-glucopyranoside

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.4606 mL 12.3031 mL 24.6063 mL 49.2126 mL 61.5157 mL
5 mM 0.4921 mL 2.4606 mL 4.9213 mL 9.8425 mL 12.3031 mL
10 mM 0.2461 mL 1.2303 mL 2.4606 mL 4.9213 mL 6.1516 mL
50 mM 0.0492 mL 0.2461 mL 0.4921 mL 0.9843 mL 1.2303 mL
100 mM 0.0246 mL 0.123 mL 0.2461 mL 0.4921 mL 0.6152 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on Oxyresveratrol 2-O-beta-D-glucopyranoside

Inhibitory effects of constituents from Morus alba var. multicaulis on differentiation of 3T3-L1 cells and nitric oxide production in RAW264.7 cells.[Pubmed:21772233]

Molecules. 2011 Jul 19;16(7):6010-22.

A new arylbenzofuran, 3',5'-dihydroxy-6-methoxy-7-prenyl-2-arylbenzofuran (1), and 25 known compounds, including moracin R (2), moracin C (3), moracin O (4), moracin P (5), artoindonesianin O (6), moracin D (7), alabafuran A (8), mulberrofuran L (9), mulberrofuran Y (10), kuwanon A (11), kuwanon C (12), kuwanon T (13), morusin (14), kuwanon E (15), sanggenon F (16), betulinic acid (17), uvaol (18), ursolic acid (19), beta-sitosterol (20), Oxyresveratrol 2-O-beta-D-glucopyranoside (21), mulberroside A (22), mulberroside B (23), 5,7-dihydroxycoumarin 7-O-beta-D-glucopyranoside (24), 5,7-dihydroxycoumarin 7-O-beta-D-apiofuranosyl-(1-->6)-O-beta-D-glucopyranoside (25) and adenosine (26), were isolated from Morus alba var. multicaulis Perro. (Moraceae). Their structures were determined by spectroscopic methods. The prenyl-flavonoids 11-14, 16, triterpenoids 17,18 and 20 showed significant inhibitory activity towards the differentiation of 3T3-L1 adipocytes. The arylbenzofurans 1-10 and prenyl-flavonoids 11-16 also showed significant nitric oxide (NO) production inhibitory effects in RAW264.7 cells.

Three major metabolites of mulberroside A in rat intestinal contents and feces.[Pubmed:19787570]

Planta Med. 2010 Mar;76(4):362-4.

Mulberroside A, a major stilbene constituent of MORUS ALBA L. (Moraceae), displays significant antitussive and antiasthmatic effects in animals. As part of our ongoing research on its biotransformation in rats, mulberroside A was orally administered to rats, and the metabolites in the gastrointestinal contents and feces were investigated. Three major metabolites were isolated from the feces of rats and identified as oxyresveratrol-2- O- beta- D-glucopyranoside ( 1), oxyresveratrol-3'- O- beta- D-glucopyranoside ( 2), and oxyresveratrol ( 3) on the basis of chemical and spectroscopic evidence. The three metabolites were also detected in the small intestinal contents of rats following oral administration of mulberroside A. These findings suggest that mulberroside A is metabolized prior to absorption into the body.

Tyrosinase inhibitory constituents from the roots of Morus nigra: a structure-activity relationship study.[Pubmed:20297841]

J Agric Food Chem. 2010 May 12;58(9):5368-73.

The phytochemical profiles of Morus nigra roots and twigs were compared by HPLC with those of the old and young twigs of Morus alba which are known to contain oxyresveratrol and mulberroside A as major components. It was found that M. nigra root extract contains some unknown natural products with potential tyrosinase inhibitory activity. The extract (95% ethanol) of the roots of M. nigra was further investigated in this study. One new compound, 5'-geranyl-5,7,2',4'-tetrahydroxyflavone, and twenty-eight known phenolic compounds were isolated. Their structures were identified by mass spectrometry and NMR spectroscopy. Nine compounds, 5'-geranyl-5,7,2',4'-tetrahydroxyflavone, steppogenin-7-O-beta-D-glucoside, 2,4,2',4'-tetrahydroxychalcone, moracin N, kuwanon H, mulberrofuran G, morachalcone A, oxyresveratrol-3'-O-beta-D-glucopyranoside and oxyresveratrol-2-O-beta-D-glucopyranoside, showed better tyrosinase inhibitory activities than kojic acid. It was noteworthy that the IC(50) values of 2,4,2',4'-tetrahydroxychalcone and morachalcone A were 757-fold and 328-fold lower than that of kojic acid, respectively, suggesting a great potential for their development as effective natural tyrosinase inhibitors.

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