An isoflavone with diverse biological activities
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Prunetin

Item No. 29432

Technical Information
Formal Name
5-hydroxy-3-(4-hydroxyphenyl)-7-methoxy-4H-1-benzopyran-4-one
CAS Number
552-59-0
Molecular Formula
C16H12O5
Formula Weight
Purity
≥95%
Formulation
A crystalline solid
DMF: 10 mg/mlDMSO: 10 mg/mlDMSO:PBS (pH 7.2) (1:3): 0.25 mg/ml
λmax
261 nm
SMILES
COC1=CC(O)=C2C(OC=C(C3=CC=C(O)C=C3)C2=O)=C1
InChi Code
InChI=1S/C16H12O5/c1-20-11-6-13(18)15-14(7-11)21-8-12(16(15)19)9-2-4-10(17)5-3-9/h2-8,17-18H,1H3
InChi Key
KQMVAGISDHMXJJ-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Prunetin is an isoflavone that has been found in P. yedoensis and has diverse biological activities.1,2,3,4,5 It is an allosteric inhibitor of hamster liver aldehyde dehydrogenase 2 (ALDH2; IC50 = 0.45 µM) and an antagonist of the progesterone receptor when used at concentrations of 25 and 50 µM.2,3 It has estrogenic activity in MVLN cells when used at concentrations ranging from 1 to 50 µM and inhibits proliferation of MCF-7 breast cancer cells when used at 0.01 to 50 µM.4 It decreases LPS-induced increases in nitric oxide (NO) and prostaglandin E2 (PGE2; Item No. 14010) levels, NOS2/iNOS expression, and NF-κB activation in RAW 264.7 macrophages when used at concentrations of 50 and 100 µM.1 Prunetin (10 mg/kg) prevents LPS-induced increases in serum TNF-α, IL-1β, and IL-6 levels in a mouse model of septic shock. It also inhibits the secretion of matrix metalloproteinase-3 (MMP-3) in isolated rabbit articular chondrocytes and prevents the production of MMP-3 in the knee joint of rats in a model of osteoarthritis following administration of a 50 or 100 µM dose into the knee joint.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Gabsik, Y., Ham, I., and Choi, H.-Y. Anti-inflammatory effect of prunetin via the suppression of NF-κB pathway. Food Chem. Toxicol. 58, 124-132 (2013).

    2. Lowe, E.D., Gao, G.-Y., Johnson, L.N., et alStructure of daidzin, a naturally occurring anti-alcohol-addiction agent, in complex with human mitochondrial aldehyde dehydrogenase. J. Med. Chem. 51(15), 4482-4487 (2008).

    3. Lee, J.-H., Dean, M., Austin, J.R., et alIrilone from red clover (Trifolium pratense) potentiates progesterone signaling. J. Nat. Prod. 81(9), 1962-1967 (2018).

    4. Le Bail, J.-C., Champavier, Y., Chulia, A.-J., et alEffects of phytoestrogens on aromatase, 3β and 17β-hydroxysteroid dehydrogenase activities and human breast cancer cells. Life Sci. 66(14), 1281-1291 (2000).

    5. Nam, D.C., Kim, B.K., Lee, H.J., et alEffects of prunetin on the proteolytic activity, secretion and gene expression of MMP-3 in vitro and production of MMP-3 in vivo. Korean J. Physiol. Pharmacol. 20(2), 221-228 (2016).