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Vol. 28, Issue 3, 298-307, March 2000
National Center for Toxicological Research, Jefferson, Arkansas
Soybean products containing isoflavones are widely consumed
in Western and Asian diets for putative health benefits, but adverse effects are also possible. The conjugated forms of isoflavones present
in a soy nutritional supplement (predominately acetyl glucosides) and
in blood from two human volunteers after consuming the supplement (7- and 4'-glucuronides and sulfates) were identified using liquid
chromatography coupled with electrospray/tandem mass spectrometry.
Circulating conjugates of genistein and daidzein were quantified using
selective enzymatic hydrolysis and deuterated internal standards for
liquid chromatography-electrospray/mass spectrometry. The levels
of isoflavone glucuronides were much greater than the corresponding
sulfates or aglycones. The substrate activities of genistein and
daidzein were evaluated with recombinant human UDP glucuronosyl
transferase (UGT) and sulfotransferase (SULT) by using enzyme kinetics.
The SULTs 1A1*2, 1E, and 2A1 catalyzed formation of a single
genistein sulfate; however, SULTs 1A2*1 and 1A3 had no observed
activity. None of the SULTs showed activity with daidzein. Although
several UGTs (1A1, 1A4, 1A6, 1A7, 1A9, and 1A10) catalyzed 7- and
4'-glucuronidation of genistein or daidzein, the UGT 1A10 isoform,
which is found in human colon but not liver, was found to be specific
for genistein. Glucuronidation of only genistein was observed in human
colon microsomes, although nearly equal activity was observed for
daidzein in human liver and kidney microsomes. These findings suggest a
prominent role for glucuronidation of genistein in the intestine
concomitant with absorption, although hepatic glucuronidation of
absorbed genistein and daidzein aglycones is also likely.
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