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Structure Database (LMSD)

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Common Name

Butein

Systematic Name

Synonyms

LM ID

LMPK12120111

Formula

C₁₅H₁₂O₅

Exact Mass

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272.068475

Status

Curated

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Classification

Biological Context

Butein is a plant polyphenol that is classified as a chalcone, due to the propenone linkage between the phenol groups. Like other polyphenols, butein is a potent antioxidant and affects the numerous pathways modulated by oxidant tone, including inflammation, cancer, and immune response.^1,2,3 It inhibits 5-lipoxygenase, the enoyl-acyl-carrier protein reductase of P. falciparum, angiotensin-converting enzyme, and Src kinase (IC50 or Ki values of 0.01, 2.97, 0.73, and 65 μM, respectively).^4,5,6,7 Butein is also a sirtuin activator, increasing trichostatin A -insensitive deacetylase activity.^8,9

This information has been provided by Cayman Chemical

References

1. McArdle, B.M., Campitelli, M.R., and Quinn, R.J. A common protein fold topology shared by flavonoid biosynthetic enzymes and therapeutic targets. J. Nat. Prod. 69(1), 14-17 (2006).

2. Sharma, S.K., Parasuraman, P., Kumar, G., et al. Green tea catechins potentiate triclosan binding to enoyl-ACP reductase from Plasmodium falciparum (PfENR). J. Med. Chem. 50(4), 765-775 (2007).

3. Yadav, V.R., Prasad, S., Sung, B., et al. The role of chalcones in suppression of NF-κB-mediated inflammation and cancer. Int. Immunopharmacol. 11(3), 295-309 (2011).

4. Sogawa, S., Nihro, Y., Ueda, H., et al. 3,4-Dihydroxychalcones as potent 5-lipoxygenase and cyclooxygenase inhibitors. J. Med. Chem. 36(24), 3904-3909 (1993).

5. Lee, E.H., Song, D.G., Lee, J.Y., et al. Inhibitory effect of the compounds isolated from Rhus verniciflua on aldose reductase and advanced glycation endproducts. Biol. Pharm. Bull. 31(8), 1626-1630 (2008).

6. Gupta, S.C., Kim, J.H., Prasad, S., et al. Regulation of survival, proliferation, invasion, angiogenesis, and metastasis of tumor cells through modulation of inflammatory pathways by nutraceuticals. Cancer Metastasis Rev. 29(3), 405-434 (2010).

7. Bonesi, M., Loizzo, M.R., Statti, G.A., et al. The synthesis and angiotensin converting enzyme (ACE) inhibitory activity of chalcones and their pyrazole derivatives. Bioorg. Med. Chem. Lett. 20(6), 1990-1993 (2010).

8. Szczepankiewicz, B.G., and Ng, P.Y. Sirtuin modulators: Targets for metabolic diseases and beyond. Curr. Top. Med. Chem. 8(17), 1533-1544 (2008).

9. Wood, J.G., Rogina, B., Lavu, S., et al. Sirtuin activators mimic caloric restriction and delay ageing in metazoans. Nature 430, 686-689 (2004).