Journal of Applied Biological Chemistry

The Korean Society for Applied Biological Chemistry (한국응용생명화학회)
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Isoflavone Daidzein: Chemistry and Bacterial Metabolism

  • Kim, Mi-Hyang (Program in Applied Biological Chemistry, Department of Agricultural Biotechnology and research Institute for Agricultural Sciences, Seoul National University) ;
  • Han, Jae-Hong (Metalloenzyme Research Group and Department of Biotechnology, Chung-Ang University) ;
  • Kim, Soo-Un (Program in Applied Biological Chemistry, Department of Agricultural Biotechnology and research Institute for Agricultural Sciences, Seoul National University)
  • Published : 2008.12.31
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Abstract

Isoflavone daidzein is a phytoestrogen widely distributed in Leguminosae and is especially rich in the soybean. The C6-C3 (rings B and C) unit of isoflavones is derived from the phenylpropanoid pathway and the remaining C6 (ring A) unit is from the polyketide pathway. This unique carbon skeleton is the result of isomerization of the flavone catalyzed by the isoflavone synthase, a cytochrome P450 enzyme. The isoflavones daidzein and genistein are present in the plant mostly in the glucosylated forms. However, in the human intestine, the glycosidic linkage is broken, and the free form is uptaked into blood stream. The free form is further metabolized into various reduction products to end up at the equol, which is known to have the most potent estrogenic effect among the metabolites. Several human intestinal bacteria that can convert daidzein into equol have been described, and the study into the chemistry and biochemistry of the daizein reduction would be rewarding to the improvement of the human health.

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