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First published on September 30, 2005; DOI: 10.1124/dmd.105.004929

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Received for publication April 5, 2005.
Revised September 28, 2005.
Accepted for publication September 28, 2005.

STRUCTURAL ELUCIDATION OF HYDROXYLATED METABOLITES OF THE ISOFLAVAN EQUOL BY GC/MS AND HPLC/MS

Corinna E Rufer 1, Hansruedi Glatt 2, Sabine E Kulling 3*

1 Federal Research Centre for Nutrition and Food 2 German Institute of Human Nutrition 3 University of Potsdam

* Address correspondence to: E-mail: skulling{at}gmx.de

Abstract

Equol has - as other isoflavonoids - recently gained considerable interest due to its possible health effects. However, detailed studies on the metabolism of equol are scarce. Therefore, we investigated the phase I metabolism of equol using liver microsomes from Aroclor-treated male Wistar rats as well as from a male human. The identification of the metabolites formed was elucidated using high performance liquid chromatography (HPLC) with diode array detection, HPLC/atmospheric pressure ionization electrospray mass spectrometry, gas chromatography-mass spectrometry as well as reference compounds. (+/-)-Equol was converted to eleven metabolites by the liver microsomes from Aroclor pretreated rats comprising three aromatic monohydroxylated and four aliphatic monohydroxylated as well as four dihydroxylated products. The main metabolite was identified as 3'-hydroxy-equol. Using human liver microsomes, equol was converted to six metabolites with 3'-hydroxy- and 6-hydroxy-equol as main products. Furthermore the aliphatic hydroxylated metabolite 4-hydroxy-equol, which was recently detected in human urine after soy consumption, was formed. On the basis of these findings it is suggested that phase I metabolism of equol is part of a complex biotransformation of the soy isoflavone daidzein in humans in vivo.


Key words: cytochrome P450 catalyzed oxidations, GC/MS, HPLC, human CYP enzymes, liver microsomes, metabolite identification


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