An isoflavone with diverse biological activities
Technical Support & Resources

Information provided in the product description is from published literature. Due to the nature of scientific experimentation, your results (e.g., selectivity and effective concentrations) or specific application for this product may differ. If you have questions about how this product fits your application, please contact our technical support staff.

Visit our FAQ

Contact Us

Toll Free Phone (USA and Canada Only): (888) 526-5351
Direct Phone: (734) 975-3888

Request Technical Support

Technical Support Request

To streamline the process attach the appropriate questionnaire to your inquiry.

Download IHC QuestionnaireDownload WB Questionnaire

View Our Privacy Statement for details on how we use and protect your data. In addition, this site is protected by hCaptcha and its Privacy Policy and Terms of Service apply.

Methylophiopogonanone B

Item No. 30193

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(3R)-2,3-dihydro-5,7-dihydroxy-3-[(4-methoxyphenyl)methyl]-6,8-dimethyl-4H-1-benzopyran-4-one
CAS Number
74805-91-7
Molecular Formula
C19H20O5
Formula Weight
328.4
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMSO: 10 mM
λmax
212, 298 nm
SMILES
OC1=C2C(OC[C@@H](CC3=CC=C(OC)C=C3)C2=O)=C(C)C(O)=C1C
InChi Code
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
InChi Key
UFMAZRUMVFVHLY-CYBMUJFWSA-N
Origin
Plant/Ophiopogonis radix
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Recommended Products

Certificates of Analysis & Batch Specific Data

Provide batch numbers separated by commas to download or request available product inserts, QC sheets, certificates of analysis, data packs, and GC-MS data.

Download most recent Certificate of Analysis for this product

    1 mg

    $95

    Add

    5 mg

    $302

    Add

    10 mg

    $510

    Add

    25 mg

    $1,037

    Add
    Cayman Chemical
    Visit Our Cancer Resource Center
    Find Tools & Resources to Study the Hallmarks of Cancer
    • Cancer cell signaling & regulation
    • Cancer metabolism
    • Tumor microenvironment
    EXPLORE NOW
    Product Description

    Methylophiopogonanone B is an isoflavone that has been found in O. japonicus and has diverse biological activities.1,2,3,4 It increases Rho activity in normal human epidermal melanocytes (NHEMs) when used at a concentration of 1 µM.1 Methylophiopogonanone B inhibits LPS-induced nitric oxide (NO) production in BV-2 microglia with an IC50 value of 7.8 µM.2 It reduces hydrogen peroxide-induced production of reactive oxygen species (ROS), apoptosis, and decreases in superoxide dismutase (SOD) activity in human umbilical vein endothelial cells (HUVECs) when used at concentrations of 40 and 50 µM.3 It is cytotoxic to SMMC-7721 and HeLa cancer cells (IC50s = 34.6 and 6 µg/ml, respectively).4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Ito, A., Kanamaru, A., and Tada, A. A novel agent, methylophiopogonanone B, promotes Rho activation and tubulin depolymerization. Mol. Cell. Biochem. 297(1-2), 121-129 (2007).

    2. Li, N., Zhang, J.-Y., Zeng, K.-W., et al. Anti-inflammatory homoisoflavonoids from the tuberous roots of Ophiopogon japonicus. Fitoterapia 83(6), 1042-1045 (2012).

    3. Wang, L., Zhou, Y., Qin, Y., et al. Methylophiopogonanone B of radix ophiopogonis protects cell from H2O2-induced apoptosis through the NADPH oxidase pathway in HUVECs. Mol. Med. Rep. 20(4), 3691-3700 (2019).

    4. Wang, K.-W., Zhang, H., Shen, L.-W., et al. Novel steroidal saponins from Liriope graminifolia (Linn.) baker with anti-tumor activities. Carbohydr. Res. 346(2), 253-258 (2011).