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Methylophiopogonone B (Methylophiopogonone B)

Cat No.:V72905 Purity: ≥98%
Methylophiopogonone B is an isoflavone extracted from Ophiopogonis Tiber that scavenges •OH and H2O2.
Methylophiopogonone B (Methylophiopogonone B)
Methylophiopogonone B (Methylophiopogonone B) Chemical Structure CAS No.: 74805-89-3
Product category: Reactive Oxygen Species
This product is for research use only, not for human use. We do not sell to patients.
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1mg
5mg
10mg
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Product Description
Methylophiopogonone B is an isoflavone extracted from Ophiopogonis Tiber that scavenges •OH and H2O2.
Methylophiopogonone B is a homoisoflavonoid compound isolated from Ophiopogon japonicus, a traditional Chinese medicinal herb known for treating cardiovascular and respiratory ailments. This compound exhibits a range of pharmacological activities, including antioxidant, anti-inflammatory, and cardioprotective effects. It has been shown to scavenge reactive oxygen species and inhibit the expression of pro-inflammatory cytokines, helping to reduce oxidative stress and inflammation. Its bioactive structure supports vascular health and cellular protection, making it a promising natural lead for developing therapies targeting heart disease and inflammatory disorders.
Biological Activity I Assay Protocols (From Reference)
Targets
Reactive Oxygen Species (ROS) signaling pathways. Methylophiopogonone B acts as a free radical scavenger, targeting hydroxyl radicals (·OH) and hydrogen peroxide (H2O2), thereby reducing oxidative stress levels in biological systems.
ln Vitro
In vitro studies have demonstrated that Methylophiopogonone B can scavenge hydroxyl radicals (·OH) and hydrogen peroxide (H2O2) to a certain extent. It exhibits antioxidant activity by neutralizing reactive oxygen species, which helps reduce oxidative damage in cellular environments. The compound shows potential in reducing the expression of pro-inflammatory cytokines and mitigating oxidative stress-mediated cellular injury.
ln Vivo
In vivo studies indicate that Methylophiopogonone B possesses cardioprotective effects, likely mediated through its antioxidant and anti-inflammatory activities. The compound helps reduce systemic oxidative stress and inflammation, which contributes to the protection of cardiovascular tissues. Its ability to scavenge reactive oxygen species and inhibit pro-inflammatory cytokine expression makes it a candidate for further investigation in animal models of heart disease and inflammatory disorders.
Enzyme Assay
A common protocol for evaluating radical scavenging activity is the DPPH (2,2-diphenyl-1-picrylhydrazyl) assay. Test compound solutions are prepared at various concentrations (0-100 mM) and mixed with an equal volume of 0.1 mM DPPH methanolic solution in a 96-well plate. Methanol serves as blank control and quercetin as positive control. After incubation at 37degC for 30 minutes in the dark, absorbance is measured at 517 nm using a microplate reader. The percentage of radical scavenging activity is calculated, and IC₅0 values are derived from concentration-response curves.
Cell Assay
To evaluate cellular ROS scavenging activity, cells are seeded in 96-well plates and treated with test compound for 24-48 hours. Oxidative stress is induced using an appropriate oxidant such as H2O2 or tert-butyl hydroperoxide. After treatment, cells are incubated with a fluorescent ROS indicator like DCFH-DA for 30 minutes at 37degC. Fluorescence intensity is measured using a microplate reader with excitation/emission wavelengths of 485/535 nm. Data are normalized to control wells and IC₅0 values calculated based on the reduction in ROS levels compared to oxidant-treated controls.
Animal Protocol
Animals are administered Methylophiopogonone B orally or intraperitoneally at doses ranging from 5-50 mg/kg daily for 2-4 weeks. Blood and tissue samples are collected for analysis of oxidative stress biomarkers (MDA, SOD, GSH), inflammatory cytokines (TNF-alpha, IL-6, IL-1beta), and histopathological examination of cardiac or vascular tissues. Pharmacodynamic endpoints include reduction in infarct size, improvement in cardiac function parameters, and attenuation of tissue oxidative damage compared to vehicle-treated disease model controls.
ADME/Pharmacokinetics
Methylophiopogonone B is soluble in DMSO (25 mg/mL) and can be formulated for in vivo administration using DMSO:PEG300:Tween 80:Saline (10:40:5:45) or similar vehicles. The compound is stable when stored as powder at -20degC for up to 3 years and in solution at -80degC for 6 months. Pharmacokinetic properties are not extensively reported, but bioavailability is expected to be moderate due to its flavonoid structure.
Toxicity/Toxicokinetics
Acute oral toxicity is considered low based on its natural product origin and traditional use. No significant adverse effects were observed at typical experimental doses in animal studies. Standard safety studies have not been extensively performed; however, the compound is derived from a traditional medicinal herb with a long history of human use, suggesting an acceptable safety profile for research purposes. Further toxicological evaluation including genotoxicity and chronic toxicity studies would be required for clinical development.
References

[1]. Studies on the Constituents of Ophiopogonis Tuber. V. Isolation of a Novel Class of Homoisoflavonoids and Determination of Their Structures (1). Chemical and Pharmaceutical Bulletin. Volume 28 (1980) Issue 5.

Additional Infomation
Methylophiopogonone B is a homoflavonoid with the structure 4H-1-benzopyran-4-one, substituted with hydroxyl groups at positions 5 and 7, methyl groups at positions 6 and 8, and a (4-methoxyphenyl)methyl group at position 3. It is a plant metabolite. It belongs to the homoflavonoid, resorcinol, and monomethoxyphenyl groups. Methylophiopogonone B has been reported to exist in Ophiopogon japonicus, and relevant data are available for reference.
The compound is structurally classified as a homoisoflavonoid (C1₉H1₈O₅, MW 326.34). Beyond antioxidant and cardioprotective effects, Methylophiopogonone B may possess additional anti-inflammatory properties due to inhibition of pro-inflammatory cytokine expression. It is not a marketed drug but remains a research compound of interest for cardiovascular drug discovery. It is a controlled substance and not for sale in certain territories.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C19H18O5
Molecular Weight
326.34
Exact Mass
326.115
CAS #
74805-89-3
PubChem CID
23259413
Appearance
Off-white to light yellow solid powder
Density
1.3±0.1 g/cm3
Boiling Point
547.7±50.0 °C at 760 mmHg
Flash Point
199.7±23.6 °C
Vapour Pressure
0.0±1.5 mmHg at 25°C
Index of Refraction
1.641
LogP
4.14
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
5
Rotatable Bond Count
3
Heavy Atom Count
24
Complexity
494
Defined Atom Stereocenter Count
0
SMILES
CC1=C(C(=C2C(=C1O)C(=O)C(=CO2)CC3=CC=C(C=C3)OC)C)O
InChi Key
BUTFXZVBLOLETI-UHFFFAOYSA-N
InChi Code
InChI=1S/C19H18O5/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/h4-7,9,20-21H,8H2,1-3H3
Chemical Name
5,7-dihydroxy-3-[(4-methoxyphenyl)methyl]-6,8-dimethylchromen-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

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)
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
Solubility (In Vivo)
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.

Injection Formulations
(e.g. IP/IV/IM/SC)
Injection Formulation 1: DMSO : Tween 80: Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution 50 μL Tween 80 850 μL Saline)
*Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution.
Injection Formulation 2: DMSO : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO 400 μLPEG300 50 μL Tween 80 450 μL Saline)
Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO 900 μL Corn oil)
Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals).
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Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO 900 μL (20% SBE-β-CD in saline)]
*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.
Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin 500 μL Saline)
Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO 100 μLPEG300 200 μL castor oil 650 μL Saline)
Injection Formulation 7: Ethanol : Cremophor : Saline = 10: 10 : 80 (i.e. 100 μL Ethanol 100 μL Cremophor 800 μL Saline)
Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline
Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH 900 μL Corn oil)
Injection Formulation 10: EtOH : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH 400 μLPEG300 50 μL Tween 80 450 μL Saline)


Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium)
Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose
Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals).
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Oral Formulation 3: Dissolved in PEG400
Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose
Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose
Oral Formulation 6: Mixing with food powders


Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 3.0643 mL 15.3214 mL 30.6429 mL
5 mM 0.6129 mL 3.0643 mL 6.1286 mL
10 mM 0.3064 mL 1.5321 mL 3.0643 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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An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
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  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
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  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
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  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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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.

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