![[Feedback]](/icons/banner/feedbackACT.gif){kind=icon}
![[For Subscribers]](/icons/banner/subscriberACT.gif){kind=icon}
![[Archive]](/icons/banner/archiveACT.gif){kind=icon}
![[Search]](/icons/banner/searchACT.gif){kind=icon}
![[Contents]](/icons/banner/tocACT.gif){kind=icon}
|
|
|
|
|
||
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.
This article has been cited by other articles:
|
|
 |
|
  K. D. R. Setchell, X. Zhao, S. E. Shoaf, and K. Ragland The Pharmacokinetics of S-(-)Equol Administered as SE5-OH Tablets to Healthy Postmenopausal Women J. Nutr., November 1, 2009; 139(11): 2037 - 2043. [Abstract] [Full Text] [PDF]
|
|
|
|
 |
|
 K. D. Setchell, X. Zhao, P. Jha, J. E Heubi, and N. M Brown The pharmacokinetic behavior of the soy isoflavone metabolite S-(-)equol and its diastereoisomer R-(+)equol in healthy adults determined by using stable-isotope-labeled tracers Am. J. Clinical Nutrition, October 1, 2009; 90(4): 1029 - 1037. [Abstract] [Full Text] [PDF]
|
|
|
|
 |
|
 S. W. J. Wang, K. H. Kulkarni, L. Tang, J. R. Wang, T. Yin, T. Daidoji, H. Yokota, and M. Hu Disposition of Flavonoids via Enteric Recycling: UDP-Glucuronosyltransferase (UGT) 1As Deficiency in Gunn Rats Is Compensated by Increases in UGT2Bs Activities J. Pharmacol. Exp. Ther., June 1, 2009; 329(3): 1023 - 1031. [Abstract] [Full Text] [PDF]
|
|
|
|
|
|
J. W Lampe Interindividual differences in response to plant-based diets: implications for cancer risk Am. J. Clinical Nutrition, May 1, 2009; 89(5): 1553S - 1557S. [Abstract] [Full Text] [PDF]
|
|
|
|
 |
|
 G. P. Miller, C. F. Lichti, A. K. Zielinska, A. Mazur, S. M. Bratton, A. Gallus-Zawada, M. Finel, J. H. Moran, and A. Radominska-Pandya Identification of Hydroxywarfarin Binding Site in Human UDP Glucuronosyltransferase 1A10: Phenylalanine90 Is Crucial for the Glucuronidation of 6- and 7-Hydroxywarfarin but Not 8-Hydroxywarfarin Drug Metab. Dispos., November 1, 2008; 36(11): 2211 - 2218. [Abstract] [Full Text] [PDF]
|
|
|
|
|
|
K. Hosoda, T. Furuta, A. Yokokawa, K. Ogura, A. Hiratsuka, and K. Ishii Plasma Profiling of Intact Isoflavone Metabolites by High-Performance Liquid Chromatography and Mass Spectrometric Identification of Flavone Glycosides Daidzin and Genistin in Human Plasma after Administration of Kinako Drug Metab. Dispos., August 1, 2008; 36(8): 1485 - 1495. [Abstract] [Full Text] [PDF]
|
|
|
|
|
|
A. Zielinska, C. F. Lichti, S. Bratton, N. C. Mitchell, A. Gallus-Zawada, V.-H. Le, M. Finel, G. P. Miller, A. Radominska-Pandya, and J. H. Moran Glucuronidation of Monohydroxylated Warfarin Metabolites by Human Liver Microsomes and Human Recombinant UDP-Glucuronosyltransferases J. Pharmacol. Exp. Ther., January 1, 2008; 324(1): 139 - 148. [Abstract] [Full Text] [PDF]
|
|
|
|
|
|
S. W. J. Wang, J. Chen, X. Jia, V. H. Tam, and M. Hu Disposition of Flavonoids via Enteric Recycling: Structural Effects and Lack of Correlations between in Vitro and in Situ Metabolic Properties Drug Metab. Dispos., November 1, 2006; 34(11): 1837 - 1848. [Abstract] [Full Text] [PDF]
|
|
|
|
 |
|
 Y. H. Ju, K. F. Allred, C. D. Allred, and W. G. Helferich Genistein stimulates growth of human breast cancer cells in a novel, postmenopausal animal model, with low plasma estradiol concentrations Carcinogenesis, June 1, 2006; 27(6): 1292 - 1299. [Abstract] [Full Text] [PDF]
|
|
|
|
|
|
L. Gu, S. E. House, R. L. Prior, N. Fang, M. J. J. Ronis, T. B. Clarkson, M. E. Wilson, and T. M. Badger Metabolic Phenotype of Isoflavones Differ among Female Rats, Pigs, Monkeys, and Women J. Nutr., May 1, 2006; 136(5): 1215 - 1221. [Abstract] [Full Text] [PDF]
|
|
|
|
|
|
Y. H. Ju, J. Fultz, K. F. Allred, D. R. Doerge, and W. G. Helferich Effects of dietary daidzein and its metabolite, equol, at physiological concentrations on the growth of estrogen-dependent human breast cancer (MCF-7) tumors implanted in ovariectomized athymic mice Carcinogenesis, April 1, 2006; 27(4): 856 - 863. [Abstract] [Full Text] [PDF]
|
|
|
|
|
|
C. Manach, G. Williamson, C. Morand, A. Scalbert, and C. Remesy Bioavailability and bioefficacy of polyphenols in humans. I. Review of 97 bioavailability studies Am. J. Clinical Nutrition, January 1, 2005; 81(1): 230S - 242S. [Abstract] [Full Text] [PDF]
|
|
|
|
 |
|
 A. C. Scallet, R. L. Divine, R. R. Newbold, and K. B. Delclos Increased Volume of the Calbindin D28k-Labeled Sexually Dimorphic Hypothalamus in Genistein and Nonylphenol-Treated Male Rats Toxicol. Sci., December 1, 2004; 82(2): 570 - 576. [Abstract] [Full Text] [PDF]
|
|
|
|
|
|
C. D. Allred, K. F. Allred, Y. H. Ju, T. S. Goeppinger, D. R. Doerge, and W. G. Helferich Soy processing influences growth of estrogen-dependent breast cancer tumors Carcinogenesis, September 1, 2004; 25(9): 1649 - 1657. [Abstract] [Full Text] [PDF]
|
|
|
|
|
|
C. Manach, A. Scalbert, C. Morand, C. Remesy, and L. Jimenez Polyphenols: food sources and bioavailability Am. J. Clinical Nutrition, May 1, 2004; 79(5): 727 - 747. [Abstract] [Full Text] [PDF]
|
|
|
|
 |
|
 P. Fanti, T. J. Stephenson, I. M. Kaariainen, B. Rezkalla, Y. Tsukamoto, T. Morishita, M. Nomura, C. Kitiyakara, L. J. Custer, and A. A. Franke Serum isoflavones and soya food intake in Japanese, Thai and American end-stage renal disease patients on chronic haemodialysis Nephrol. Dial. Transplant., September 1, 2003; 18(9): 1862 - 1868. [Abstract] [Full Text] [PDF]
|
|
|
|
|
|
J. Chen, H. Lin, and M. Hu Metabolism of Flavonoids via Enteric Recycling: Role of Intestinal Disposition J. Pharmacol. Exp. Ther., March 1, 2003; 304(3): 1228 - 1235. [Abstract] [Full Text] [PDF]
|
|
|
|
|
|
Y. Zhang, S. Hendrich, and P. A. Murphy Glucuronides Are the Main Isoflavone Metabolites in Women J. Nutr., February 1, 2003; 133(2): 399 - 404. [Abstract] [Full Text] [PDF]
|
|
|
|
|
|
K. D. R. Setchell, N. M. Brown, and E. Lydeking-Olsen The Clinical Importance of the Metabolite Equol--A Clue to the Effectiveness of Soy and Its Isoflavones J. Nutr., December 1, 2002; 132(12): 3577 - 3584. [Abstract] [Full Text] [PDF]
|
|
|
|
|
|
K. D. Setchell, N. M Brown, L. Zimmer-Nechemias, W. T Brashear, B. E Wolfe, A. S Kirschner, and J. E Heubi Evidence for lack of absorption of soy isoflavone glycosides in humans, supporting the crucial role of intestinal metabolism for bioavailability Am. J. Clinical Nutrition, August 1, 2002; 76(2): 447 - 453. [Abstract] [Full Text] [PDF]
|
|
|
|
 |
|
 H. B. Patisaul, M. Melby, P. L. Whitten, and L. J. Young Genistein Affects ER{beta}- But Not ER{alpha}-Dependent Gene Expression in the Hypothalamus Endocrinology, June 1, 2002; 143(6): 2189 - 2197. [Abstract] [Full Text] [PDF]
|
|
|
|
|
|
H. B. Patisaul, M. Dindo, P. L. Whitten, and L. J. Young Soy Isoflavone Supplements Antagonize Reproductive Behavior and Estrogen Receptor {{alpha}}- and {beta}-Dependent Gene Expression in the Brain Endocrinology, July 1, 2001; 142(7): 2946 - 2952. [Abstract] [Full Text] [PDF]
|
|
|
|
|
|
H. C. Chang, M. I. Churchwell, K. B. Delclos, R. R. Newbold, and D. R. Doerge Mass Spectrometric Determination of Genistein Tissue Distribution in Diet-Exposed Sprague-Dawley Rats J. Nutr., August 1, 2000; 130(8): 1963 - 1970. [Abstract] [Full Text]
|
|
 |
 |
 |
|
 |
 |
 |
