LIPID MAPS

Structure Database (LMSD)

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Common Name

Dihydrodaidzein

Systematic Name

7,4'-Dihydroxyisoflavanone

Synonyms

LM ID

LMPK12050447

Formula

C₁₅H₁₂O₄

Exact Mass

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256.07356

Status

Curated

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Classification

Biological Context

Dihydrodaidzein is an active, estrogenic metabolite of daidzein.¹ It has vasodilatory action on rat isolated aortic rings at 1 µg/ml.² It stimulates the estrogen receptor-dependent growth of breast cancer MCF-7 cells at micromolar concentrations.³ Dihydrodaidzein is produced by the metabolism of daidzein in colonic bacteria and may be further metabolized to various bioactive compounds, including equol .^4,5

This information has been provided by Cayman Chemical

References

1. Chin-Disting, J.P.F., Fisher, L.J., Lewis, T.V., et al. The vascular activity of some isoflavone metabolites: Implications for a cardioprotective role. Brit. J. Pharmacol. 133(4), 595-605 (2001).

2. Franke, A.A., Lai, J.F., and Halm, B.M. Absorption, distribution, metabolism, and excretion of isoflavonoids after soy intake. Arch. Biochem. and Biophys. 559, 24-28 (2014).

3. Kinjo, J., Tsuchihashi, R., Morita, K., et al. Interactions of phytoestrogens with estrogen receptors α and β (III). Estrogenic activities of soy isoflavone aglycones and their metabolites isolated from human urine. Biol. Pharm. Bull. 27(2), 185-188 (2004).

4. Rafii, F. The role of colonic bacteria in the metabolism of the natural isoflavone daidzin to equol. Metabolites 5(1), 56-73 (2015).

5. Schröder, D., Matthies, A., Engst, W., et al. Identification and expression of genes involved in the conversion of daidzein and genistein by the equol-forming bacterium Slackia isoflavoniconvertens. Appl. Environ. Microb. 79(11), 3494-3502 (2013).