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Chemical Compound Review:

butein (E)-1-(2,4-dihydroxyphenyl)- 3-(3,4...

Synonyms: CHEMBL128000, SureCN139243, B178_SIGMA, CHEBI:3237, CHEBI:310267, ...

Nakadate, T. et al., Selvam, C. et al., Sogawa, S. et al., Hayashi, K. et al., Rajendran, P. et al., et al.

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Disease relevance of butein

Lipoxygenase inhibitors such as 3,4,2',4'-tetrahydroxychalcone, nordihydroguaiaretic acid, quercetin and 2,3,5-trimethyl-6-(12-hydroxy-5,10-dodecadiynyl)-1,4-benzoquinone (AA861) effectively inhibited BrMBA-caused epidermal ODC induction and ear edema formation [1].
Butein (3,4,2',4'-tetrahydroxychalcone) ameliorates experimental anti-glomerular basement membrane antibody-associated glomerulonephritis (3) [2].
In particular, we found that 2',4',3,4-tetrahydroxychalcone (3) exhibited a potent inhibitory effect on H2O2-induced hemolysis due to an antioxidant effect [3].

High impact information on butein

The IC50 of AA861 and 3,4,2',4'-tetrahydroxychalcone for epidermal 12-lipoxygenase were 1.9 and 0.2 microM, respectively [4].
Evaluation of COX-1 inhibitory activity of 3,4,2',4'-tetrahydroxychalcone and 7,3',4'-trihydroxy fl avone provided the IC(50) values of 28.4 and 36.7 micro M respectively [5].
Butein (3,4,2',4'-tetrahydroxychalcone), a plant polyphenol, has been known to elucidate endothelium-dependent vasodilation [6].

Associations of butein with other chemical compounds

We found the inactivation of IKK by butein was direct and involved cysteine residue 179 [7].
Butein inhibited proliferation and significantly potentiated the apoptotic effects of paclitaxel and doxorubicin in HCC cells [8].

References

Inhibition by lipoxygenase inhibitors of 7-bromomethylbenz[a]anthracene-caused epidermal ornithine decarboxylase induction and skin tumor promotion in mice. Nakadate, T., Yamamoto, S., Aizu, E., Kato, R. Carcinogenesis (1989) [Pubmed]
Butein (3,4,2',4'-tetrahydroxychalcone) ameliorates experimental anti-glomerular basement membrane antibody-associated glomerulonephritis (3). Hayashi, K., Nagamatsu, T., Honda, S., Suzuki, Y. Eur. J. Pharmacol. (1996) [Pubmed]
Protective effects of hydroxychalcones on free radical-induced cell damage. Sogawa, S., Nihro, Y., Ueda, H., Miki, T., Matsumoto, H., Satoh, T. Biol. Pharm. Bull. (1994) [Pubmed]
Inhibition of 12-O-tetradecanoylphorbol-13-acetate-mediated epidermal ornithine decarboxylase induction and skin tumor promotion by new lipoxygenase inhibitors lacking protein kinase C inhibitory effects. Aizu, E., Nakadate, T., Yamamoto, S., Kato, R. Carcinogenesis (1986) [Pubmed]
Cyclooxygenase inhibitory flavonoids from the stem bark of Semecarpus anacardium Linn. Selvam, C., Jachak, S.M., Bhutani, K.K. Phytotherapy research : PTR. (2004) [Pubmed]
Hypotensive effect of butein via the inhibition of angiotensin converting enzyme. Kang, D.G., Kim, Y.C., Sohn, E.J., Lee, Y.M., Lee, A.S., Yin, M.H., Lee, H.S. Biol. Pharm. Bull. (2003) [Pubmed]
Butein, a tetrahydroxychalcone, inhibits nuclear factor (NF)-kappaB and NF-kappaB-regulated gene expression through direct inhibition of IkappaBalpha kinase beta on cysteine 179 residue. Pandey, M.K., Sandur, S.K., Sung, B., Sethi, G., Kunnumakkara, A.B., Aggarwal, B.B. J. Biol. Chem. (2007) [Pubmed]
Suppression of signal transducer and activator of transcription 3 activation by butein inhibits growth of human hepatocellular carcinoma in vivo. Rajendran, P., Ong, T.H., Chen, L., Li, F., Shanmugam, M.K., Vali, S., Abbasi, T., Kapoor, S., Sharma, A., Kumar, A.P., Hui, K.M., Sethi, G. Clin. Cancer Res. (2011) [Pubmed]

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