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Divisions of
*
Clinical Mass Spectrometry and
Gastroenterology and Nutrition,
**
Department of Pediatrics, Children’s Hospital Medical Center and College of Pharmacy, University of Cincinnati College of Medicine, Cincinnati, Ohio 45229 and
Department of Nutrition, University of Surrey, Guildford, U.K.
3To whom correspondence should be addressed at Clinical Mass Spectrometry, Children’s Hospital Medical Center, 3333 Burnet Avenue, Cincinnati, OH 45229. E-mail: SETCK0{at}chmcc.org
The pharmacokinetic behavior of naturally occurring isoflavones has been determined for the first time in healthy adults. We compared plasma kinetics of pure daidzein, genistein and their ß-glycosides administered as a single-bolus dose to 19 healthy women. This study demonstrates differences in the pharmacokinetics of isoflavone glycosides compared with their respective ß-glycosides. Although all isoflavones are efficiently absorbed from the intestinal tract, there are striking differences in the fate of aglycones and ß-glycosides. Mean time to attain peak plasma concentrations (tmax) for the aglycones genistein and daidzein was 5.2 and 6.6 h, respectively, whereas for the corresponding ß-glycosides, the tmax was delayed to 9.3 and 9.0 h, respectively, consistent with the residence time needed for hydrolytic cleavage of the glycoside moiety for bioavailability. The apparent volume of distribution of isoflavones confirms extensive tissue distribution after absorption. Plasma genistein concentrations are consistently higher than daidzein when equal amounts of the two isoflavones are administered, and this is accounted for by the more extensive distribution of daidzein (236 L) compared with genistein (161 L). The systemic bioavailability of genistein [mean AUC = 4.54 µg/(mL · h)] is much greater than that of daidzein [mean AUC = 2.94 µg/(mL · h)], and bioavailability of these isoflavones is greater when ingested as ß-glycosides rather than aglycones as measured from the area under the curve of the plasma appearance and disappearance concentrations. The pharmacokinetics of methoxylated isoflavones show distinct differences depending on the position of the methoxyl group in the molecule. Glycitin, found in two phytoestrogen supplements, underwent hydrolysis of the ß-glycoside moiety and little further biotransformation, leading to high plasma glycitein concentrations. Biochanin A and formononetin, two isoflavones found in one phytoestrogen supplement, were rapidly and efficiently demethylated, resulting in high plasma genistein and daidzein concentrations typically observed after the ingestion of soy-containing foods. These differences in pharmacokinetics and metabolism have implications for clinical studies because it cannot be assumed that all isoflavones are comparable in their pharmacokinetics and bioavailability. An analysis of 33 phytoestrogen supplements and extracts revealed considerable differences in the isoflavone content from that claimed by the manufacturers. Plasma concentrations of isoflavones show marked qualitative and quantitative differences depending on the type of supplement ingested. These studies indicate a need for improvement in quality assurance and standardization of such products.
KEY WORDS: • phytoestrogens • isoflavones • pharmacokinetics • soy foods • supplements • humans • blood
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Y. Liu and M. Hu Absorption and Metabolism of Flavonoids in the Caco-2 Cell Culture Model and a Perused Rat Intestinal Model Drug Metab. Dispos., April 1, 2002; 30(4): 370 - 377. [Abstract] [Full Text] [PDF]
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 C. A. Lamartiniere, J. Wang, M. Smith-Johnson, and I.-E. Eltoum Daidzein: Bioavailability, Potential for Reproductive Toxicity, and Breast Cancer Chemoprevention in Female Rats Toxicol. Sci., February 1, 2002; 65(2): 228 - 238. [Abstract] [Full Text] [PDF]
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M. R. Adams, D. L. Golden, M. S. Anthony, T. C. Register, and J. K. Williams The Inhibitory Effect of Soy Protein Isolate on Atherosclerosis in Mice Does Not Require the Presence of LDL Receptors or Alteration of Plasma Lipoproteins J. Nutr., January 1, 2002; 132(1): 43 - 49. [Abstract] [Full Text] [PDF]
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Y. H. Ju, C. D. Allred, K. F. Allred, K. L. Karko, D. R. Doerge, and W. G. Helferich Physiological Concentrations of Dietary Genistein Dose-Dependently Stimulate Growth of Estrogen-Dependent Human Breast Cancer (MCF-7) Tumors Implanted in Athymic Nude Mice J. Nutr., November 1, 2001; 131(11): 2957 - 2962. [Abstract] [Full Text] [PDF]
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M. J. Messina and C. L. Loprinzi Soy for Breast Cancer Survivors: A Critical Review of the Literature J. Nutr., November 1, 2001; 131(11): 3095S - 3108. [Abstract] [Full Text] [PDF]
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K. D. R. Setchell Soy Isoflavones--Benefits and Risks from Nature's Selective Estrogen Receptor Modulators (SERMs) J. Am. Coll. Nutr., October 1, 2001; 20(90005): 354S - 362. [Abstract] [Full Text]
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