Absolute bioavailability of isoflavones from soy protein isolate-containing food in female Balb/c mice

Journal of Agricultural and Food Chemistry

Volumn 58, Issue 7, 2010, Pages 4529-4536

  Andrade, Juan E ^a   Twaddle, Nathan C ^b   Helferich, William G ^a   Doerge, Daniel R ^b  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

^b NATIONAL CENTER FOR TOXICOLOGICAL RESEARCH   (United States)

Author keywords

Bioavailability; Genistein; Isoflavone; Mice; Pharmacokinetics; Soy protein isolate

Indexed keywords

ISOFLAVONE DERIVATIVE; PLANT EXTRACT; SOYBEAN PROTEIN;

ANIMAL; ANIMAL MODEL; ARTICLE; BAGG ALBINO MOUSE; BIOAVAILABILITY; BLOOD; FEMALE; HUMAN; ISOLATION AND PURIFICATION; MOUSE; SOYBEAN; TISSUE DISTRIBUTION;

ANIMALS; BIOLOGICAL AVAILABILITY; FEMALE; HUMANS; ISOFLAVONES; MICE; MICE, INBRED BALB C; MODELS, ANIMAL; PLANT EXTRACTS; SOY FOODS; SOYBEAN PROTEINS; TISSUE DISTRIBUTION;

ANIMALIA; GLYCINE MAX; MUS;

EID: 77950648248     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf9039843     Document Type: Article

References (52)

1. Day, A. J.; Canada, F. J.; Diaz, J. C.; Kroon, P. A.; McLauchlan, R.; Faulds, C. B.; Plumb, G. W.; Morgan, M. R.; Williamson, G. Dietary flavonoid and isoflavone glycosides are hydrolysed by the lactase site of lactase phlorizin hydrolase FEBS Lett. 2000, 468 (2?3) 166 - 170
2. Hosoda, K.; Furuta, T.; Yokokawa, A.; Ogura, K.; Hiratsuka, A.; Ishii, K. 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. 2008, 36 (8) 1485 - 1495
3. Hawksworth, G.; Drasar, B. S.; Hill, M. J. Intestinal bacteria and the hydrolysis of glycosidic bonds J. Med. Microbiol. 1971, 4 (4) 451 - 459
4. Chang, Y. C.; Nair, M. G. Metabolism of daidzein and genistein by intestinal bacteria J. Nat. Prod. 1995, 58 (12) 1892 - 1896
5. Sfakianos, J.; Coward, L.; Kirk, M.; Barnes, S. Intestinal uptake and biliary excretion of the isoflavone genistein in rats J. Nutr. 1997, 127 (7) 1260 - 1268
6. Allred, C. D.; Twaddle, N. C.; Allred, K. F.; Goeppinger, T. S.; Churchwell, M. I.; Ju, Y. H.; Helferich, W. G.; Doerge, D. R. Soy processing affects metabolism and disposition of dietary isoflavones in ovariectomized BALB/c mice J. Agric. Food Chem. 2005, 53 (22) 8542 - 8550
7. Steensma, A.; Faassen-Peters, M. A.; Noteborn, H. P.; Rietjens, I. M. Bioavailability of genistein and its glycoside genistin as measured in the portal vein of freely moving unanesthetized rats J. Agric. Food Chem. 2006, 54 (21) 8006 - 8012
8. Coldham, N. G.; Zhang, A. Q.; Key, P.; Sauer, M. J. Absolute bioavailability of [14C] genistein in the rat; plasma pharmacokinetics of parent compound, genistein glucuronide and total radioactivity Eur. J. Drug Metab. Pharmacokinet. 2002, 27 (4) 249 - 258
9. Moon, Y. J.; Sagawa, K.; Frederick, K.; Zhang, S.; Morris, M. E. Pharmacokinetics and bioavailability of the isoflavone biochanin A in rats AAPS J. 2006, 8 (3) E433 - E442
10. Sepehr, E.; Cooke, G. M.; Robertson, P.; Gilani, G. S. Effect of glycosidation of isoflavones on their bioavailability and pharmacokinetics in aged male rats Mol. Nutr. Food Res. 2009, 53 (Suppl. 1) S16 - S26
11. Chang, Y. C.; Nair, M. G.; Santell, R. C.; Helferich, W. G. Microwave-mediated synthesis of anticarcinogenic isoflavones from soybeans J. Agric. Food Chem. 1994, 42 (9) 1869 - 1871
12. Nurmi, T.; Mazur, W.; Heinonen, S.; Kokkonen, J.; Adlercreutz, H. Isoflavone content of the soy based supplements J. Pharm. Biomed. Anal. 2002, 28 (1) 1 - 11
13. Wu, S.; Murphy, P. A.; Johnson, L. A.; Reuber, M. A.; Fratzke, A. R. Simplified process for soybean glycinin and beta-conglycinin fractionation J. Agric. Food Chem. 2000, 48 (7) 2702 - 2708
14. Penalvo, J. L.; Nurmi, T.; Adlercreutz, H. A simplified HPLC method for total isoflavones in soy products Food Chem. 2004, 87 (2) 297 - 305
15. Reeves, P. G.; Nielsen, F. H.; Fahey, G. C., Jr. AIN-93 purified diets for laboratory rodents: final report of the American Institute of Nutrition ad hoc writing committee on the reformulation of the AIN-76A rodent diet J. Nutr. 1993, 123 (11) 1939 - 1951
16. Nutrient Requirements of Laboratory Animals, 4 th revised ed.; National Academy Press: Washington, DC, 1995; p 192.
17. U.S. Department of Agriculture, Agricultural Research Service. USDA National Nutrient Database for Standard Reference. Release 22; Nutrient Data Laboratory Home Page, 2009; http://www.ars.usda.gov/nutrientdata.
18. Twaddle, N. C.; Churchwell, M. I.; Doerge, D. R. High-throughput quantification of soy isoflavones in human and rodent blood using liquid chromatography with electrospray mass spectrometry and tandem mass spectrometry detection J. Chromatogr., B: Anal. Technol. Biomed. Life Sci. 2002, 777 (1?2) 139 - 145
19. Fukutake, M.; Takahashi, M.; Ishida, K.; Kawamura, H.; Sugimura, T.; Wakabayashi, K. Quantification of genistein and genistin in soybeans and soybean products Food Chem. Toxicol. 1996, 34 (5) 457 - 461
20. Doerge, D. R.; Chang, H. C.; Churchwell, M. I.; Holder, C. L. Analysis of soy isoflavone conjugation in vitro and in human blood using liquid chromatography-mass spectrometry Drug. Metab. Dispos. 2000, 28 (3) 298 - 307
21. Sepehr, E.; Cooke, G.; Robertson, P.; Gilani, G. S. Bioavailability of soy isoflavones in rats Part I: application of accurate methodology for studying the effects of gender and source of isoflavones Mol. Nutr. Food Res. 2007, 51 (7) 799 - 812
22. Setchell, K. D.; Zimmer-Nechemias, L.; Cai, J.; Heubi, J. E. Exposure of infants to phyto-oestrogens from soy-based infant formula Lancet 1997, 350 (9070) 23 - 27
23. Castellanos, V. H.; Litchford, M. D.; Campbell, W. W. Modular protein supplements and their application to long-term care Nutr. Clin. Pract. 2006, 21 (5) 485 - 504
24. Eldridge, A. C.; Kwolek, W. F. Soybean isoflavones: Effect of environment and variety on composition J. Agric. Food Chem. 1983, 31 (2) 394 - 396
25. Seguin, P.; Zheng, W.; Smith, D. L.; Deng, W. Isoflavone content of soybean cultivars grown in eastern Canada J. Sci. Food Agric. 2004, 84 (11) 1327 - 1332
26. Kim, S. H.; Jung, W. S.; Ahn, J. K.; Kim, J. A.; Chung, I. M. Quantitative analysis of the isoflavone content and biological growth of soybean (Glycine max L.) at elevated temperature, CO2 level and N application J. Sci. Food Agric. 2005, 85 (15) 2557 - 2566
27. Rasolohery, C. A.; Berger, M.; Lygin, A.; Lozovaya, V.; Nelson, R. L.; Dayde, J. Effect of temperature and water availability during late maturation of the soybean seed on germ and cotyledon isoflavone content and composition J. Sci. Food Agric. 2008, 88 (2) 218 - 228
28. Aguiar, C. L.; Baptista, A. S.; Walder, J. M.; Tsai, S. M.; Carrao-Panizzi, M. C.; Kitajima, E. W. Changes in isoflavone profiles of soybean treated with gamma irradiation Int. J. Food Sci. Nutr. 2009, 1 - 8
29. Genovese, M. I.; Barbosa, A. C.; Pinto Mda, S.; Lajolo, F. M. Commercial soy protein ingredients as isoflavone sources for functional foods Plant Foods Hum. Nutr. 2007, 62 (2) 53 - 58
30. Wang, C.; Ma, Q.; Pagadala, S.; Sherrard, M. S.; Krishman, P. G. Changes of isoflavones during processing of soy protein isolates J. Am. Oil Chem. Soc. 1998, 75 (3) 337 - 341
31. Yin, L. J.; Li, L. T.; Liu, H.; Saito, M.; Tatsumi, E. Effects of fermentation temperature on the content and composition of isoflavones and beta-glucosidase activity in sufu Biosci., Biotechnol., Biochem. 2005, 69 (2) 267 - 272
32. Huang, R. Y.; Chou, C. C. Stability of isoflavone isomers in steamed black soybeans and black soybean Koji stored under different conditions J. Agric. Food Chem. 2009, 57 (5) 1927 - 1932
33. Lee, S. J.; Ahn, J. K.; Kim, S. H.; Kim, J. T.; Han, S. J.; Jung, M. Y.; Chung, I. M. Variation in isoflavone of soybean cultivars with location and storage duration J. Agric. Food Chem. 2003, 51 (11) 3382 - 3389
34. Lin, J.; Krishnan, P. G.; Wang, C. Retention of isoflavones and saponins during the processing of soy protein isolates J. Am. Oil Chem. Soc. 2006, 83 (1) 59 - 63
35. Setchell, K. D.; Cole, S. J. Variations in isoflavone levels in soy foods and soy protein isolates and issues related to isoflavone databases and food labeling J. Agric. Food Chem. 2003, 51 (14) 4146 - 4155
36. USDA-Iowa State University, Agricultural Research Service. Database on the Isoflavone Content of Foods; Nutrient Data Laboratory Website, 2002; http://www.nal.usda.gov/fnic/foodcomp/Data/isoflav/isoflav.html.
37. Zhou, S.; Hu, Y.; Zhang, B.; Teng, Z.; Gan, H.; Yang, Z.; Wang, Q.; Huan, M.; Mei, Q. Dose-dependent absorption, metabolism, and excretion of genistein in rats J. Agric. Food Chem. 2008, 56 (18) 8354 - 8359
38. Qiu, F.; Chen, X. Y.; Song, B.; Zhong, D. F.; Liu, C. X. Influence of dosage forms on pharmacokinetics of daidzein and its main metabolite daidzein-7-O-glucuronide in rats Acta Pharmacol. Sin. 2005, 26 (9) 1145 - 1152
39. Kwon, S. H.; Kang, M. J.; Huh, J. S.; Ha, K. W.; Lee, J. R.; Lee, S. K.; Lee, B. S.; Han, I. H.; Lee, M. S.; Lee, M. W.; Lee, J.; Choi, Y. W. Comparison of oral bioavailability of genistein and genistin in rats Int. J. Pharm. 2007, 337 (1?2) 148 - 154
40. Jefferson, W. N.; Doerge, D. R.; Padilla-Banks, E.; Woodling, K. A.; Kissling, G. E.; Newbold, R. R. Oral exposure to genistin, the glycosylated form of genistein, during neonatal life adversely affects the female reproductive system Environ. Health Perspect. 2009, 117, 1883 - 1889
41. Holder, C. L.; Churchwell, M. I.; Doerge, D. R. Quantification of soy isoflavones, genistein and daidzein, and conjugates in rat blood using LC/ES-MS J. Agric. Food Chem. 1999, 47 (9) 3764 - 3770
42. McClain, R. M.; Wolz, E.; Davidovich, A.; Pfannkuch, F.; Edwards, J. A.; Bausch, J. Acute, subchronic and chronic safety studies with genistein in rats Food Chem. Toxicol. 2006, 44 (1) 56 - 80
43. Izumi, T.; Piskula, M. K.; Osawa, S.; Obata, A.; Tobe, K.; Saito, M.; Kataoka, S.; Kubota, Y.; Kikuchi, M. Soy isoflavone aglycones are absorbed faster and in higher amounts than their glucosides in humans J. Nutr. 2000, 130 (7) 1695 - 1699
44. Setchell, K. D.; Brown, N. M.; Desai, P.; Zimmer-Nechemias, L.; Wolfe, B. E.; Brashear, W. T.; Kirschner, A. S.; Cassidy, A.; Heubi, J. E. Bioavailability of pure isoflavones in healthy humans and analysis of commercial soy isoflavone supplements J. Nutr. 2001, 131 (4 Suppl.) 1362S - 1375S
45. Richelle, M.; Pridmore-Merten, S.; Bodenstab, S.; Enslen, M.; Offord, E. A. Hydrolysis of isoflavone glycosides to aglycones by beta-glycosidase does not alter plasma and urine isoflavone pharmacokinetics in postmenopausal women J. Nutr. 2002, 132 (9) 2587 - 2592
46. Rufer, C. E.; Bub, A.; Moseneder, J.; Winterhalter, P.; Sturtz, M.; Kulling, S. E. Pharmacokinetics of the soybean isoflavone daidzein in its aglycone and glucoside form: a randomized, double-blind, crossover study Am. J. Clin. Nutr. 2008, 87 (5) 1314 - 1323
47. Nielsen, I. L.; Williamson, G. Review of the factors affecting bioavailability of soy isoflavones in humans Nutr. Cancer 2007, 57 (1) 1 - 10
48. Busby, M. G.; Jeffcoat, A. R.; Bloedon, L. T.; Koch, M. A.; Black, T.; Dix, K. J.; Heizer, W. D.; Thomas, B. F.; Hill, J. M.; Crowell, J. A.; Zeisel, S. H. Clinical characteristics and pharmacokinetics of purified soy isoflavones: Single-dose administration to healthy men Am. J. Clin. Nutr. 2002, 75 (1) 126 - 136
49. King, R. A.; Broadbent, J. L.; Head, R. J. Absorption and excretion of the soy isoflavone genistein in rats J. Nutr. 1996, 126 (1) 176 - 182
50. Zubik, L.; Meydani, M. Bioavailability of soybean isoflavones from aglycone and glucoside forms in American women Am. J. Clin. Nutr. 2003, 77 (6) 1459 - 1465
51. Cassidy, A.; Brown, J. E.; Hawdon, A.; Faughnan, M. S.; King, L. J.; Millward, J.; Zimmer-Nechemias, L.; Wolfe, B.; Setchell, K. D. Factors affecting the bioavailability of soy isoflavones in humans after ingestion of physiologically relevant levels from different soy foods J. Nutr. 2006, 136 (1) 45 - 51
52. Muthyala, R. S.; Ju, Y. H.; Sheng, S.; Williams, L. D.; Doerge, D. R.; Katzenellenbogen, B. S.; Helferich, W. G.; Katzenellenbogen, J. A. Equol, a natural estrogenic metabolite from soy isoflavones: convenient preparation and resolution of R- and S-equols and their differing binding and biological activity through estrogen receptors alpha and beta Bioorg. Med. Chem. 2004, 12 (6) 1559 - 1567