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Common Name

Prunetin

Systematic Name

5,4'-Dihydroxy-7-methoxyisoflavone

Synonyms

Prunusetin

LM ID

LMPK12050353

Formula

C₁₆H₁₂O₅

Exact Mass

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284.068475

Status

Curated

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Classification

Biological Context

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) 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

This information has been provided by Cayman Chemical

References

1. Nam, D.C., Kim, B.K., Lee, H.J., et al. Effects 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).

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

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

4. 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).

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