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2'-Methoxykurarinone

CAS# 270249-38-2

2'-Methoxykurarinone

Catalog No. BCN2986----Order now to get a substantial discount!

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Quality Control of 2'-Methoxykurarinone

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Chemical structure

2'-Methoxykurarinone

3D structure

Chemical Properties of 2'-Methoxykurarinone

Cas No. 270249-38-2 SDF Download SDF
PubChem ID 11982641 Appearance Powder
Formula C27H32O6 M.Wt 452.6
Type of Compound Flavonoids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name (2S)-7-hydroxy-2-(4-hydroxy-2-methoxyphenyl)-5-methoxy-8-[(2R)-5-methyl-2-prop-1-en-2-ylhex-4-enyl]-2,3-dihydrochromen-4-one
SMILES CC(=CCC(CC1=C(C=C(C2=C1OC(CC2=O)C3=C(C=C(C=C3)O)OC)OC)O)C(=C)C)C
Standard InChIKey KTAQQSUPNZAWEY-OSPHWJPCSA-N
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 2'-Methoxykurarinone

The roots of Sophora flavescens Ait.

Biological Activity of 2'-Methoxykurarinone

Description2'-Methoxykurarinone has strong alpha-glucosidase inhibitory activities, with IC(50) values of 155 microM. 2'-Methoxykurarinone is a noncompetitive inhibitor of protein tyrosine phosphatase 1B, it exhibits cellular activity in the insulin signaling pathway by increasing the insulin-stimulated Akt phosphorylation level in human hepatocellular liver carcinoma HepG2 cells, suggesting its potential for new anti-insulin-resistant drug developments. 2′-Methoxykurarinone exhibits lethal activity against Trypanosoma cruzi.,the minimum lethal concentrations is 6.9 uM.
TargetsAntifection | Akt
In vitro

Protein tyrosine phosphatase 1B inhibitory activity of lavandulyl flavonoids from roots of Sophora flavescens.[Pubmed: 24782228]

Planta Med., 2014, 80(7):557-60.

Protein tyrosine phosphatase 1B is a non-transmembrane protein tyrosine phosphatase and major negative regulator in insulin signaling cascades, and much attention has been paid to protein tyrosine phosphatase 1B inhibitors as potential therapies for diabetes.
METHODS AND RESULTS:
The screening of a natural compound library led to the discovery of five lavandulyl flavonoids, which were isolated from the roots of Sophora flavescens, as novel PTP1B inhibitors: kuraridin (1), norkurarinone (2), kurarinone (3), 2'-Methoxykurarinone (4), and kushenol T (5). The three most potent compounds, 1, 2, and 4 (IC50 < 30 μM), were demonstrated to be noncompetitive inhibitors of protein tyrosine phosphatase 1B based on a kinetic analysis, and they exhibited different inhibitory selectivities against four homologous protein tyrosine phosphatases (T cell protein tyrosine phosphatase, vaccinia H1-related phosphatase, and Src homology domain 2-containing protein tyrosine phosphatases 1 and 2).

Trypanocidal Flavonoids from Sophora flavescens[Reference: WebLink]

Natural Medicines, 2003, 57:253-5.

The acetone extract of Sophora flavescens Aiton (Leguminosae) exhibited lethal activity against Trypanosoma cruzi.
METHODS AND RESULTS:
Column chromatographic separation of the extract guided by trypanocidal activity afforded a new prenylated flavanone (4), together with nine known flavonoids: sophoraflavanone G (1), (-) -kurarinone (2), kushenol L (3), 2'-Methoxykurarinone, (5), 7,4′-dihydroxy-5-methoxy-8-(γ,γ-dimethylallyl)-flavanone (6), leachianone A (7), 8-prenylnaringenin (8), noranhydroicaritin (9) and alopecurone G (10). The structure of the new flavanone 4 was determined on the basis of spectroscopic analyses.
CONCLUSIONS:
The minimum lethal concentrations of these compounds against epimastigotes of T. cruzi were 3.7 μM (1), 14 μM (2), 7.1 μM (3), 7.2 μM (4), 6.9 μM (5), 71 μM (6), 5.5 μM (7), 18 μM (8), 4.4 μM (9) and 3.6 μM (10).

Protocol of 2'-Methoxykurarinone

Kinase Assay

Glycosidase inhibitory flavonoids from Sophora flavescens.[Pubmed: 16462036]

Biol. Pharm. Bull., 2006, 29(2):302-5.

The methanol extract of Sophora flavescens showed a potent glycosidase inhibitory activity.
METHODS AND RESULTS:
Active components were identified as well-known flavonoid antioxidants: kushenol A (1), (-)-kurarinone (2), sophoraflavanone G (3), 2'-Methoxykurarinone (4), kurarinol (5), 8-prenylkaempferol (6), isoxanthohumol (7), kuraridin (8) and maackian (9). All flavonoids were effective inhibitors of alpha-glucosidase and beta-amylase. Interestingly, lavandulylated flavanones 1-5 had strong alpha-glucosidase inhibitory activities, with IC(50) values of 45 microM, 68 microM, 37 microM, 155 microM and 179 microM, respectively. Kushenol A (1) which does not bear a 4'-hydroxy group showed selective alpha-glucosidase inhibitory activity. Lavandulylated chalcone, kuraridine (8), exhibited IC(50) value of 57 microM against beta-glucosidase, which is the first report of a chalcone displaying glycosidase inhibition.
CONCLUSIONS:
Results showed that 8-lavandulyl group in B-ring was a key factor of the glycosidase inhibitory activities. The inhibition pattern was noncompetitive for alpha-glucosidase, whereas mixed inhibition was observed for beta-amylase.

2'-Methoxykurarinone Dilution Calculator

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2'-Methoxykurarinone Molarity Calculator

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Preparing Stock Solutions of 2'-Methoxykurarinone

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.2095 mL 11.0473 mL 22.0946 mL 44.1891 mL 55.2364 mL
5 mM 0.4419 mL 2.2095 mL 4.4189 mL 8.8378 mL 11.0473 mL
10 mM 0.2209 mL 1.1047 mL 2.2095 mL 4.4189 mL 5.5236 mL
50 mM 0.0442 mL 0.2209 mL 0.4419 mL 0.8838 mL 1.1047 mL
100 mM 0.0221 mL 0.1105 mL 0.2209 mL 0.4419 mL 0.5524 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 2'-Methoxykurarinone

Protein tyrosine phosphatase 1B inhibitory activity of lavandulyl flavonoids from roots of Sophora flavescens.[Pubmed:24782228]

Planta Med. 2014 May;80(7):557-60.

Protein tyrosine phosphatase 1B is a non-transmembrane protein tyrosine phosphatase and major negative regulator in insulin signaling cascades, and much attention has been paid to protein tyrosine phosphatase 1B inhibitors as potential therapies for diabetes. The screening of a natural compound library led to the discovery of five lavandulyl flavonoids, which were isolated from the roots of Sophora flavescens, as novel PTP1B inhibitors: kuraridin (1), norkurarinone (2), kurarinone (3), 2'-methoxykurarinone (4), and kushenol T (5). The three most potent compounds, 1, 2, and 4 (IC50 < 30 microM), were demonstrated to be noncompetitive inhibitors of protein tyrosine phosphatase 1B based on a kinetic analysis, and they exhibited different inhibitory selectivities against four homologous protein tyrosine phosphatases (T cell protein tyrosine phosphatase, vaccinia H1-related phosphatase, and Src homology domain 2-containing protein tyrosine phosphatases 1 and 2). Compounds 1, 2, and 4 also exhibited cellular activity in the insulin signaling pathway by increasing the insulin-stimulated Akt phosphorylation level in human hepatocellular liver carcinoma HepG2 cells, suggesting their potential for new anti-insulin-resistant drug developments.

Glycosidase inhibitory flavonoids from Sophora flavescens.[Pubmed:16462036]

Biol Pharm Bull. 2006 Feb;29(2):302-5.

The methanol extract of Sophora flavescens showed a potent glycosidase inhibitory activity. Active components were identified as well-known flavonoid antioxidants: kushenol A (1), (-)-kurarinone (2), sophoraflavanone G (3), 2'-methoxykurarinone (4), kurarinol (5), 8-prenylkaempferol (6), isoxanthohumol (7), kuraridin (8) and maackian (9). All flavonoids were effective inhibitors of alpha-glucosidase and beta-amylase. Interestingly, lavandulylated flavanones 1-5 had strong alpha-glucosidase inhibitory activities, with IC(50) values of 45 microM, 68 microM, 37 microM, 155 microM and 179 microM, respectively. Kushenol A (1) which does not bear a 4'-hydroxy group showed selective alpha-glucosidase inhibitory activity. Lavandulylated chalcone, kuraridine (8), exhibited IC(50) value of 57 microM against beta-glucosidase, which is the first report of a chalcone displaying glycosidase inhibition. Results showed that 8-lavandulyl group in B-ring was a key factor of the glycosidase inhibitory activities. The inhibition pattern was noncompetitive for alpha-glucosidase, whereas mixed inhibition was observed for beta-amylase.

Description

(2S)-2'-Methoxykurarinone, a compound isolated from the roots of Sophora flavescens, has anti-inflammatory, antipyretic, antidiabetic, and antineoplastic effects. (2S)-2'-Methoxykurarinone (MK) inhibits osteoclastogenesis and bone resorption through down-regulation of RANKL signaling. (2S)-2'-Methoxykurarinone (MK) displays cytotoxic activity against human myeloid leukemia HL-60 cells.

Keywords:

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