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Methylophiopogonanone B

CAS# 74805-91-7

Methylophiopogonanone B

2D Structure

Catalog No. BCN5418----Order now to get a substantial discount!

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Methylophiopogonanone B

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Chemical Properties of Methylophiopogonanone B

Cas No. 74805-91-7 SDF Download SDF
PubChem ID 46886723 Appearance Light yellow powder
Formula C19H20O5 M.Wt 328.36
Type of Compound Flavonoids Storage Desiccate at -20°C
Solubility Soluble in acetone, chloroform and methanol; insoluble in water
Chemical Name (3R)-5,7-dihydroxy-3-[(4-methoxyphenyl)methyl]-6,8-dimethyl-2,3-dihydrochromen-4-one
SMILES CC1=C(C2=C(C(=C1O)C)OCC(C2=O)CC3=CC=C(C=C3)OC)O
Standard InChIKey UFMAZRUMVFVHLY-CYBMUJFWSA-N
Standard InChI InChI=1S/C19H20O5/c1-10-16(20)11(2)19-15(17(10)21)18(22)13(9-24-19)8-12-4-6-14(23-3)7-5-12/h4-7,13,20-21H,8-9H2,1-3H3/t13-/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 Methylophiopogonanone B

The roots of Ophiopogon japonicus

Biological Activity of Methylophiopogonanone B

DescriptionMethylophiopogonanone B has inhibition of hypoxia-inducible factor (HIF)-1 alpha activity.Methylophiopogonanone B can inhibit melanosome transfer to keratinocytes as well as melanocyte dendrite outgrowth, it also suppress pigmentation in a three-dimensional skin culture model through the inhibition of melanocyte dendrite outgrowth, it could result in the creation of very unique cosmetic products that would precisely control the darkening or lightening of skin tone.
TargetsHIF
In vitro

A novel agent, methylophiopogonanone B, promotes Rho activation and tubulin depolymerization.[Pubmed: 17029007]

Mol Cell Biochem. 2007 Mar;297(1-2):121-9.

Cytoskeletal reorganization, including reconstruction of actin fibers and microtubules, is essential for various biological processes, such as cell migration, proliferation and dendrite formation.
METHODS AND RESULTS:
We show here that Methylophiopogonanone B (MOPB) induces cell morphological change via melanocyte dendrite retraction and stress fiber formation. Since members of the Rho family of small GTP-binding proteins act as master regulators of dendrite formation and actin cytoskeletal reorganization, and activated Rho promotes dendrite retraction and stress fiber formation, we studied the effects of MOPB on the small GTPases using normal human epidermal melanocytes and HeLa cells. In in vitro binding assay, MOPB significantly increased GTP-Rho, but not GTP-Rac or GTP-CDC42. Furthermore, a Rho inhibitor, a Rho kinase inhibitor and a small GTPase inhibitor each blocked MOPB-induced stress fiber formation. The effect of MOPB on actin reorganization was blocked in a Rho dominant negative mutant. These results suggest MOPB acts via the Rho signaling pathway, and it may directly or indirectly activate Rho. Quantitative Western blot analysis indicated that MOPB also induced microtubule destabilization and tubulin depolymerization.
CONCLUSIONS:
Thus, MOPB appears to induce Rho activation, resulting in actin cytoskeletal reorganization, including dendrite retraction and stress fiber formation.

Control of melanosome transfer by promoting shrinkage or expansion of melanocyte dendrites.[Reference: WebLink]

Int.J. Cosmetic Sci., 2006, 28(2):148-148.

Melanosomes synthesized within melanocytes are transferred to keratinocytes through melanocyte dendrites, resulting in a constant supply of melanin to the epidermis which determines skin pigmentation. Theoretically, if we can find an effective way to control this supply of melanin to the epidermis, skin colour could be darkened or lightened.
METHODS AND RESULTS:
The objective of this study was to find safe and effective methods to inhibit or promote melanosome transfer by the shrinkage or expansion of melanocyte dendrites. Methylophiopogonanone B and centaureidin inhibited melanosome transfer to keratinocytes as well as melanocyte dendrite outgrowth. Methylswertianin and comfrey extract promoted not only melanosome transfer to keratinocytes but also expansion of melanocyte dendrites. Methylophiopogonanone B and centaureidin suppressed pigmentation in a three-dimensional skin culture model through the inhibition of melanocyte dendrite outgrowth. Methylswertianin and comfrey extract activated pigmentation in a three-dimensional skin culture model by expansion of melanocyte dendrites.
CONCLUSIONS:
Our experimental findings suggest the possibility of manipulating human skin colour by controlling melanosome transfer to cause shrinkage or expansion of dendrites. A combination of effective agents, in addition to the ones identified in this work, could result in the creation of very unique cosmetic products that would precisely control the darkening or lightening of skin tone.

Protocol of Methylophiopogonanone B

Kinase Assay

Dihydrochalcone Designed from Methylophiopogonanone B Strongly Inhibits Hypoxia-inducible Factor (HIF)-1α Activity.[Reference: WebLink]

Heterocycles, 2009, 78(8):2061-5.

Inhibition of hypoxia-inducible factor (HIF)-1 alpha activity of Methylophiopogonanone B (1) and its derivatives were investigated. As the modification of the structure of 1, dihydrochalcone (11) was leaded and showed one order higher activity (IC(50): 0.2 mu g/mL) than Methylophiopogonanone B (1) (IC(50): 2.2 mu g/mL).

Structure Identification
Carbohydr Res. 2011 Feb 1;346(2):253-8.

Novel steroidal saponins from Liriope graminifolia (Linn.) Baker with anti-tumor activities.[Pubmed: 21163470]

Phytochemical investigation of the underground parts of Liriope graminifolia (Linn.) Baker resulted in the isolation of two new steroidal saponins lirigramosides A (1) and B (2) along with four known compounds.
METHODS AND RESULTS:
The structures were determined by extensive spectral analysis, including two-dimensional (2D) NMR spectroscopy and chemical methods, to be 3-O-[β-d-xylopyranosyl-(1→3)-α-l-arabinopyranosyl-(1→2)-[α-l-rhamnopyranosyl-(1→4)]-β-d-glucopyranosyl-(25S)-spirost-5-ene-3β,17α-diol (1), 1-O-[α-l-rhamnopyranosyl-(1→2)-β-d-xylopyranosyl]-(25R)-ruscogenin (2), 1-O-β-d-xylopyranosyl-3-O-α-l-rhamnopyranosyl-(25S)-ruscogenin (3), 3-O-α-l-rhamnopyranosyl-1-O-sulfo-(25S)-ruscogenin (4), Methylophiopogonanone B (5), and 5,7-dihydroxy-3-(4-methoxybenzyl)-6-methyl-chroman-4-one, (ophiopogonanone B, 6), respectively. Compound 1 has a new (25S)-spirost-5-ene-3β,17α-diol ((25S)-pennogenin) aglycone moiety.
CONCLUSIONS:
The isolated compounds were evaluated for their cytotoxic activities against Hela and SMMC-7721 cells.

Methylophiopogonanone B Dilution Calculator

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Preparing Stock Solutions of Methylophiopogonanone B

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.0454 mL 15.2272 mL 30.4544 mL 60.9088 mL 76.1359 mL
5 mM 0.6091 mL 3.0454 mL 6.0909 mL 12.1818 mL 15.2272 mL
10 mM 0.3045 mL 1.5227 mL 3.0454 mL 6.0909 mL 7.6136 mL
50 mM 0.0609 mL 0.3045 mL 0.6091 mL 1.2182 mL 1.5227 mL
100 mM 0.0305 mL 0.1523 mL 0.3045 mL 0.6091 mL 0.7614 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 Methylophiopogonanone B

A novel agent, methylophiopogonanone B, promotes Rho activation and tubulin depolymerization.[Pubmed:17029007]

Mol Cell Biochem. 2007 Mar;297(1-2):121-9.

Cytoskeletal reorganization, including reconstruction of actin fibers and microtubules, is essential for various biological processes, such as cell migration, proliferation and dendrite formation. We show here that Methylophiopogonanone B (MOPB) induces cell morphological change via melanocyte dendrite retraction and stress fiber formation. Since members of the Rho family of small GTP-binding proteins act as master regulators of dendrite formation and actin cytoskeletal reorganization, and activated Rho promotes dendrite retraction and stress fiber formation, we studied the effects of MOPB on the small GTPases using normal human epidermal melanocytes and HeLa cells. In in vitro binding assay, MOPB significantly increased GTP-Rho, but not GTP-Rac or GTP-CDC42. Furthermore, a Rho inhibitor, a Rho kinase inhibitor and a small GTPase inhibitor each blocked MOPB-induced stress fiber formation. The effect of MOPB on actin reorganization was blocked in a Rho dominant negative mutant. These results suggest MOPB acts via the Rho signaling pathway, and it may directly or indirectly activate Rho. Quantitative Western blot analysis indicated that MOPB also induced microtubule destabilization and tubulin depolymerization. Thus, MOPB appears to induce Rho activation, resulting in actin cytoskeletal reorganization, including dendrite retraction and stress fiber formation.

Novel steroidal saponins from Liriope graminifolia (Linn.) Baker with anti-tumor activities.[Pubmed:21163470]

Carbohydr Res. 2011 Feb 1;346(2):253-8.

Phytochemical investigation of the underground parts of Liriope graminifolia (Linn.) Baker resulted in the isolation of two new steroidal saponins lirigramosides A (1) and B (2) along with four known compounds. The structures were determined by extensive spectral analysis, including two-dimensional (2D) NMR spectroscopy and chemical methods, to be 3-O-[beta-d-xylopyranosyl-(1-->3)-alpha-l-arabinopyranosyl-(1-->2)-[alpha-l-rhamn opyranosyl-(1-->4)]-beta-d-glucopyranosyl-(25S)-spirost-5-ene-3beta,17alpha-diol (1), 1-O-[alpha-l-rhamnopyranosyl-(1-->2)-beta-d-xylopyranosyl]-(25R)-ruscogenin (2), 1-O-beta-d-xylopyranosyl-3-O-alpha-l-rhamnopyranosyl-(25S)-ruscogenin (3), 3-O-alpha-l-rhamnopyranosyl-1-O-sulfo-(25S)-ruscogenin (4), Methylophiopogonanone B (5), and 5,7-dihydroxy-3-(4-methoxybenzyl)-6-methyl-chroman-4-one, (ophiopogonanone B, 6), respectively. Compound 1 has a new (25S)-spirost-5-ene-3beta,17alpha-diol ((25S)-pennogenin) aglycone moiety. The isolated compounds were evaluated for their cytotoxic activities against Hela and SMMC-7721 cells.

Description

Methylophiopogonanone B, homoisoflavonoid, is extracted from the root of Ophiopogon japonicas, shows high antioxidant ability. Methylophiopogonanone B increases GTP-Rho and acts via the Rho signaling pathway, inducing cell morphological change via actin cytoskeletal reorganization, including dendrite retraction and stress fiber formation.

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