Metabolites of daidzein and genistein and their biological activities.
A number of metabolites of daidzein and genestein have been synthesized and their biological activities determined. Equol [3], 5,7,4'-trihydroxyisoflavan [5], 4,7,4'-trihydroxyisoflavan [6], dihydrodaidzein [8], and dihydrogenistein [9] were synthesized either from daidzein [1] or genistein [2] by hydrogenation. Similarly, the derivatives 4, 7, and 11 were synthesized from 3, 6, and 10, respectively. During acetylation and nmr experiments, 9 was converted to a novel enol intermediate [10]. Antifungal, antibacterial, mosquitocidal, nematocidal, and topoisomerase inhibition activities of these compounds were evaluated, with equol [3] being the most active of the compounds tested against topoisomerase I.
Chang
Y C
YC
Department of Horticulture and Pesticide Research Center, Michigan State University, East Lansing 48824, USA.
Nair
M G
MG
Nitiss
J L
JL
D000107:Acetylation; D000330:Aedes; D000818:Animals; D000935:Antifungal Agents / Q000494:pharmacology; D000969:Antinematodal Agents / Q000633:toxicity; D002478:Cells, Cultured; D004968:Estrogens, Non-Steroidal / Q000378:metabolism* / Q000494:pharmacology* / Q000633:toxicity; D005658:Fungi / Q000187:drug effects; D019833:Genistein; D006865:Hydrogenation; D007306:Insecticides / Q000633:toxicity; D007529:Isoflavones / Q000378:metabolism* / Q000494:pharmacology* / Q000633:toxicity; D009682:Magnetic Resonance Spectroscopy; D059004:Topoisomerase I Inhibitors
D000935:Antifungal Agents; D000969:Antinematodal Agents; D004968:Estrogens, Non-Steroidal; D007306:Insecticides; D007529:Isoflavones; D059004:Topoisomerase I Inhibitors; C004742:daidzein; D019833:Genistein