LIPID MAPS

Structure Database (LMSD)

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Common Name

3'-Hydroxydaidzein

Systematic Name

Synonyms

LM ID

LMPK12050055

Formula

C₁₅H₁₀O₅

Exact Mass

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270.052825

Status

Curated

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Classification

Biological Context

3',4',7-Trihydroxyisoflavone is a natural isoflavonoid that has antioxidant activity.¹ It can be produced by the metabolism of daidzein or daidzin .^2,3 3',4',7-Trihydroxyisoflavone inhibits several signaling pathways in cells, including tyrosinase-mediated melanin formation (IC50 = 5.2 µM), casein kinase II-mediated phosphorylation of 60S acidic ribosomal P proteins, and cyclin-dependent, kinase-regulated cell proliferation.^4,5,6

This information has been provided by Cayman Chemical

References

1. Choi, K.-Y., Kim, T.-j., Koh, S.-K., et al. A-ring ortho-specific monohydroxylation of daidzein by cytochrome P450s of Nocardia farcinica IFM10152. Biotechnol. J. 4(11), 1586-1595 (2009).

2. Komiyama, K., Funayama, S., Anraku, Y., et al. Isolation of isoflavonoids possessing antioxidant activity from the fermentation broth of Streptomyces sp. J. Antibiot. (Tokyo) 42(9), 1344-1349 (1989).

3. Lee, D.E., Lee, K.Q., Song, N.R., et al. 7,3',4'-Trihydroxyisoflavone inhibits epidermal growth factor-induced proliferation and transformation of JB6 P+ mouse epidermal cells by suppressing cyclin-dependent kinases and phosphatidylinositol 3-kinase. The Journal of Biological Chemisty 285(28), 21458-21466 (2010).

4. Maekawa, T., Kosuge, S., Sakamoto, S., et al. Biochemical characterization of 60S acidic ribosomal P proteins associated with CK-II from bamboo shoots and potent inhibitors of their phosphorylation in vitro. Biol. Pharm. Bull. 22(7), 667-673 (1999).

5. Park, J.-S., Kim, D.H., Lee, J.K., et al. Natural ortho-dihydroxyisoflavone derivatives from aged Korean fermented soybean paste as potent tyrosinase and melanin formation inhibitors. Bioorg. Med. Chem. Lett. 20(3), 1162-1164 (2010).

6. Yasuda, T., and Ohsawa, K. Urinary metabolites of daidzin orally administered in rats. Biol. Pharm. Bull. 21(9), 953-957 (1998).