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 Metabolism and Disposition

Volumn 36, Issue 8, 2008, Pages 1485-1495

  Hosoda, Kaori ^a   Furuta, Takashi ^b   Yokokawa, Akitomo ^b   Ogura, Kenichiro ^b   Hiratsuka, Akira ^b   Ishii, Kazuo ^a  

^a KYORIN UNIVERSITY   (Japan)

^b TOKYO UNIVERSITY OF PHARMACY AND LIFE SCIENCES   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

DAIDZEIN; DAIDZEIN 4' GLUCURONIDE; DAIDZEIN 4' SULFATE; DAIDZEIN 7 GLUCURONIDE; DAIDZEIN 7 SULFATE; DAIDZIN; GENISTEIN; GENISTEIN 4' GLUCURONIDE; GENISTEIN 4' SULFATE; GENISTEIN 7 GLUCURONIDE; GENISTEIN 7 SULFATE; GENISTIN; GLUCURONIDE; GLYCOSIDE; ISOFLAVONE DERIVATIVE; KINAKO; PLANT EXTRACT;

ARTICLE; BODY FLUID; CONTROLLED STUDY; DIODE; DIODE ARRAY DETECTOR; DRUG CONJUGATION; DRUG TISSUE LEVEL; ELECTROSPRAY MASS SPECTROMETRY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN CELL; HUMAN EXPERIMENT; HUMAN TISSUE; HYDROLYSIS; MASS SPECTROMETRY; NEOPLASM; NORMAL HUMAN; OSTEOPOROSIS; PRIORITY JOURNAL; SOLID PHASE EXTRACTION; SOYBEAN;

CHROMATOGRAPHY, HIGH PRESSURE LIQUID; GENISTEIN; HUMANS; ISOFLAVONES; MAGNETIC RESONANCE SPECTROSCOPY; REFERENCE STANDARDS; SOYBEANS; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; SPECTROPHOTOMETRY, ULTRAVIOLET;

GLYCINE MAX;

EID: 47949092138     PISSN: 00909556     EISSN: 1521009X     Source Type: Journal    
DOI: 10.1124/dmd.108.021006     Document Type: Article

References (33)

1. Adlercreutz H (2002) Phyto-oestrogens and cancer. Lancet Oncol 3:364-373.
2. Adlercreutz H, Markkanen H, and Watanabe S (1993) Plasma concentrations of phyto-oestrogens in Japanese men. Lancet 342:1209-1210.
3. Adlercreutz H, van der Wildt J, Kinzel J, Attalla H, Wähä lä K, Makela T, Hase T, and Fotsis T (1995) Lignan and isoflavonoid conjugates in human urine. J Steroid Biochem Mol Biol 52:97-103.
4. Bektic J, Guggenberger R, Eder IE, Pelzer AE, Berger AP, Bartsch G, and Klocker H (2005) Molecular effects of the isoflavonoid genistein in prostate cancer. Clin Prostate Cancer 4:124-129.
5. 3]isoflavone internal standards. Anal Biochem 309:158-172.
6. Day AJ, Cañada FJ, Díaz JC, Kroon PA, Mclauchlan R, Faulds CB, Plumb GW, Morgan MR, and Williamson G (2000) Dietary flavonoid and isoflavone glycosides are hydrolysed by the lactase site of lactase phlorizin hydrolase. FEBS Lett 468:166-170.
7. Doerge DR, Chang HC, Churchwell MI, and Holder CL (2000) Analysis of soy isoflavone conjugation in vitro and in human blood using liquid chromatography-mass spectrometry. Drug Metab Dispos 28:298-307.
8. Fang N, Yu S, and Badger TM (2002) Characterization of isoflavones and their conjugates in female rat urine using LC/MS/MS. J Agric Food Chem 50:2700-2707.
9. Heinonen SM, Hoikkala A, Wähälä K, and Adlercreutz H (2003) Metabolism of the soy isoflavones daidzein, genistein and glycitein in human subjects: identification of new metabolites having an intact isoflavonoid skeleton. J Steroid Biochem Mol Biol 87:285-299.
10. Hirose K, Imaeda N, Tokudome Y, Goto C, Wakai K, Matsuo K, Ito H, Toyama T, Iwata H, Tokudome S, et al. (2005) Soybean products and reduction of breast cancer risk: a case-control study in Japan. Br J Cancer 93:15-22.
11. Ishii K, Furuta T, and Kasuya Y (2000) Mass spectrometric identification and high-performance liquid chromatographic determination of a flavonoid glycoside naringin in human urine. J Agric Food Chem 48:56-59.
12. Ishii K, Furuta T, and Kasuya Y (2001) Determination of rutin in human plasma by high-performance liquid chromatography utilizing solid-phase extraction and ultraviolet detection. J Chromatogr B Analyt Technol Biomed Life Sci 759:161-168.
13. Kinjo J, Tsuchihashi R, Morito K, Hirose T, Aomori T, Nagao T, Okabe H, Nohara T, and Masamune Y (2004) Interactions of phytoestrogens with estrogen receptors α and β (III): estrogenic activities of soy isoflavone aglycones and their metabolites isolated from human urine. Biol Pharm Bull 27:185-188.
14. Maskarinec G, Yamakawa R, Hebshi S, and Franke AA (2007) Urinary isoflavonoid excretion and soy consumption in three generations of Japanese women in Hawaii. Eur J Clin Nutr 61:255-261.
15. McCue P and Shetty K (2004) Health benefits of soy isoflavonoids and strategies for enhancement: a review. Crit Rev Food Sci Nutr 44:361-367.
16. Morand C, Manach C, Donovan J, and Remesy C (2001) Preparation and characterization of flavonoid metabolites present in biological samples. Methods Enzymol 335:115-121.
17. Nakano H, Ogura K, Takahashi E, Harada T, Nishiyama T, Muro K, Hiratsuka A, Kadota S, and Watabe T (2004) Regioselective monosulfation and disulfation of the phytoestrogens daidzein and genistein by human liver sulfotransferases. Drug Metab Pharmacokinet 19:216-226.
18. Needs PW and Williamson G (2001) Syntheses of daidzein-7-yl β-D-glucopyranosiduronic acid and daidzein-4′,7-yl di-β-D-glucopyranosiduronic acid. Carbohydr Res 330:511-515.
19. Németh K, Plumb GW, Berrin JG, Juge N, Jacob R, Naim HY, Williamson G, Swallow DM, and Kroon PA (2003) Deglycosylation by small intestinal epithelial cell β-glucosidases is a critical step in the absorption and metabolism of dietary flavonoid glycosides in humans. Eur J Nutr 42:29-42.
20. Nielsen ILF and Williamson G (2007) Review of the factors affecting bioavailability of soy isoflavones in humans. Nutr Cancer 57:1-10.
21. Setchell KDR and Cole SJ (2003) Variations in isoflavone levels in soy foods and soy protein isolates and issues related to isoflavone databases and food labeling. J Agric Food Chem 51:4146-4155.
22. Setchell KDR and Lydeking-Olsen E (2003) Dietary phytoestrogens and their effect on bone: evidence from in vitro and in vivo, human observational, and dietary intervention studies. Am J Clin Nutr 78:593S-609S.
23. Setchell KDR, Brown NM, Zimmer-Nechemias L, Brashear WT, Wolfe BE, Kirschner AS, and Heubi JE (2002) Evidence for lack of absorption of soy isoflavone glycosides in humans, supporting the crucial role of intestinal metabolism for bioavailability. Am J Clin Nutr 76:447-453.
24. Shelnutt SR, Cimino CO, Wiggins PA, Ronis MJ, and Badger TM (2002) Pharmacokinetics of the glucuronide and sulfate conjugates of genistein and daidzein in men and women after consumption of a soy beverage. Am J Clin Nutr 76:588-594.
25. Soidinsalo O and Wähälä K (2007) Synthesis of daidzein 7-O-β-D-glucuronide-4′-O-sulfate. Steroids 72:851-854.
26. Tsuchihashi R, Okawa M, Nohara T, Okabe H, and Kinjo J (2004) Soy isoflavone metabolites isolated from human urine. Nat Med 58:71-75.
27. Walgren RA, Lin JT, Kinne RK, and Walle T (2000) Cellular uptake of dietary flavonoid quercetin 4′-β-glucoside by sodium-dependent glucose transporter SGLT1. J Pharmacol Exp Ther 294:837-843.
28. Walz E (1931) Isoflavon- und Saponin-Glucoside in Soja hispida. Justus Liebigs Ann Chem 489:118-155.
29. Wong CK and Keung WM (1997) Daidzein sulfoconjugates are potent inhibitors of sterol sulfatase (EC 3.1.6.2). Biochem Biophys Res Commun 233:579-583.
30. Yamamoto S, Sobue T, Kobayashi M, Sasaki S, and Tsugane S (2003) Soy, isoflavones, and breast cancer risk in Japan. J Natl Cancer Inst 95:906-913.
31. Yasuda T, Mizunuma S, Kano Y, Saito K, and Ohsawa K (1996) Urinary and biliary metabolites of genistein in rats. Biol Pharm Bull 19:413-417.
32. Yuan L, Wagatsuma C, Yoshida M, Miura T, Mukoda T, Fujii H, Sun B, Kim JH, and Surh YJ (2003) Inhibition of human breast cancer growth by GCPTM (genistein combined polysaccharide) in xenogeneic athymic mice: involvement of genistein biotransformation by β-glucuronidase from tumor tissues. Mutat Res 523:55-62.
33. Zhang Y, Song TT, Cunnick JE, Murphy PA, and Hendrich S (1999) Daidzein and genistein glucuronides in vitro are weakly estrogenic and activate human natural killer cells at nutritionally relevant concentrations. J Nutr 129:399-405.