Biotransformation of soy isoflavone-glycosides in laying hens: Intestinal absorption and preferential accumulation into egg yolk of equol, a more estrogenic metabolite of daidzein

Biochimica et Biophysica Acta - General Subjects

Volumn 1674, Issue 2, 2004, Pages 122-130

  Saitoh, Sanshiroh ^a   Sato, Toshiro ^a   Harada, Hiroshi ^b   Matsuda, Tsukasa ^c  

^a J Oil Mills Inc   (Japan)

^b TOKYO UNIVERSITY OF AGRICULTURE   (Japan)

^c NAGOYA UNIVERSITY   (Japan)

Author keywords

Bioconversion; Egg yolk; Equol; Phytoestrogen; Soy isoflavone

Indexed keywords

DAIDZEIN; EQUOL; ESTROGEN; GENISTEIN; GLYCITEIN; GLYCOSIDE; ISOFLAVONE; PHYTOESTROGEN; ISOFLAVONE DERIVATIVE; PLANT MEDICINAL PRODUCT;

ANIMAL EXPERIMENT; ARTICLE; BIOTRANSFORMATION; CONJUGATION; CONTROLLED STUDY; DIET SUPPLEMENTATION; EGG LAYING; EGG YOLK; FEMALE; HEN; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; INTESTINE ABSORPTION; NONHUMAN; PRIORITY JOURNAL; SOYBEAN; ANIMAL; ANIMAL FOOD; CHEMISTRY; CHICKEN; DIET; HUMAN; METABOLISM; PHYSIOLOGY;

ANIMALIA;

ANIMAL FEED; ANIMALS; CHICKENS; DIET; EGG YOLK; ESTROGENS, NON-STEROIDAL; FEMALE; HUMANS; INTESTINAL ABSORPTION; ISOFLAVONES; PHYTOESTROGENS; PLANT PREPARATIONS; SOYBEANS;

EID: 12344266606     PISSN: 03044165     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bbagen.2004.06.006     Document Type: Article

References (38)

1. Setchell K.D.R., 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. 131:2001;1362S-1375S
2. Coward L., Barnes N.C., Setchell K.D.R., Barnes S. Genistein, daidzein, and their β-glycoside conjugates: antitumor isoflavones in soybean foods from American and Asian diets. J. Agric. Food Chem. 41:1993;1961-1967
3. Nagata C., Takatsuka N., Kawakami N., Shimizu H. Soy product intake and hot flashes in Japanese women: results from a community-based prospective study. Am. J. Epidemiol. 153:2001;790-793
4. Elizabeth A., Phuong S., Shari A., Alan C., Renee C. Dietary isoflavones reduce plasma cholesterol and atherosclerosis in C57BL/6 mice but not LDL receptor-deficient mice. J. Nutr. 128:1998;954-959
5. Alekel D.L., Germain A.S., Peterson C.T., Hanson K.B., Stewart J.W., Toda T. Isoflavone-rich soy protein isolate attenuates bone loss in the lumbar spine of perimenopausal women. Am. J. Clin. Nutr. 72:2000;844-852
6. Yellayi S., Naaz A., Szewczykowski M.A., Sato T., Woods J.A., Chang J., Segre M., Allred C.D., Helferich W.G., Cooke P.S. The phytoestrogen genistein induces thymic and immune changes: a human health concern? Proc. Natl. Acad. Sci. 99:2002;7616-7621
7. Shutt D.A., Weston R.H., Hogan J.P. Quantitative aspects of phytoestrogen metabolism in sheep fed on subterranean clover (Trifolium subterraneum cultivar clare) or red clover (Trifolium pratense). Aust. J. Agric. Resour. 21:1970;713-722
8. Eldridge A.C., Kwolek W.F. Soybean isoflavones: effect of environment and variety on composition. J. Agric. Food Chem. 31:1983;394-396
9. Murota K., Shimizu S., Miyamoto S., Izumi T., Obata A., Kikuchi M., Terao J. Unique uptake and transport of isoflavone aglycones by human intestinal caco-2 cells: comparison of isoflavonoids and flavonoids. J. Nutr. 132:2002;1956-1961
10. 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. 130:2000;1695-1699
11. Watanabe S., Yamaguchi M., Sobue T., Takahashi T., Miura T., Arai Y., Mazur W., Wahala K., Adlercreutz H. Pharmacokinetics of soybean isoflavones in plasma, urine and feces of men after ingestion of 60 g baked soybean powder (kinako). J. Nutr. 128:1998;1710-1715
12. King R.A., Bursill D.B. Plasma and urinary kinetics of the isoflavones daidzein and genistein after a single soy meal in humans. Am. J. Clin. Nutr. 67:1998;867-872
13. Rowland I.R., Wiseman H., Sanders T.A., Adlercreutz H., Bowey E.A. Interindividual variation in metabolism of soy isoflavones and lignans: influence of habitual diet on equol production by the gut flora. Nutr. Cancer. 36:2000;27-32
14. Lampe J.W., Karr S.C., Hutchins A.M., Slavin J.L. Urinary equol excretion with a soy challenge: influence of habitual diet. Proc. Soc. Exp. Biol. Med. 217:1998;335-339
15. Shutt D.A. The effects of plant oestrogens on animal reproduction. Endeavour. 35:1976;110-113
16. Shutt D.A., Cox R.I. Steroid and phyto-oestrogen binding to sheep uterine receptors in vitro. J. Endocrinol. 52:1972;299-310
17. Morito K., Hirose T., Kinjo J., Hirakawa T., Okawa M., Nohara T., Ogawa S., Inoue S., Muramatsu M., Masamune Y. Interaction of phytoestrogens with estrogen receptors α and β Biol. Pharm. Bull. 24:2001;351-356
18. Setchell K.D.R., Brown N.M., Lydeking-Olsen E. The clinical importance of the metabolite equol - a clue to the effectiveness of soy and its isoflavones. J. Nutr. 2002;3577-3584
19. Setchell K.D.R., Borriello S.P., Hulme P., Kirk D.N., Axelson M. Nonsteroidal estrogens of dietary origin: possible roles in hormone dependent disease. Am. J. Clin. Nutr. 40:1984;569-578
20. Kelly G.E., Joannou G.E., Reeder A.Y., Nelson C., Waring M.A. The variable metabolic response to dietary isoflavones in humans. Proc. Soc. Exp. Biol. Med. 208:1995;40-43
21. Monfort S.L., Thompson M.A., Czekala N.M., Kasman L.H., Shackleton C.H., Lasley B.L. Identification of a non-steroidal estrogen, equol, in the urine of pregnant macaques: correlation with steroidal estrogen excretion. J. Steroid Biochem. 20:1984;869
22. Adlercreutz H., Musey P.I., Fotsis T., Bannwart C., Wahala K., Makela T., Brunow G., Hase T. Identification of lignans and phytoestrogens in urine of chimpanzees. Clin. Chim. Acta. 158:1986;147-154
23. Uehara A., Ohta K., Sakai K., Suzuki K., Watanabe S., Adlercreutz H. Dietary fructopolysaccharides modify intestinal bioavailability of a single dose of genistein and daidzein and affect their urinary excretion and kinetics in blood of rats. J. Nutr. 131:2001;787-795
24. Tang G., Common R.H. Urinary conversion products of certain orally administered isoflavones in the fowl. Biochim. Biophys. Acta. 158:1968;402-413
25. Saitoh S., Sato T., Harada H., Takita T. Transfer of soy isoflavone into the egg yolk of chickens. Biosci. Biotechnol. Biochem. 65:2001;2220-2225
26. Hatch F., Lees R.S. Advances in Lipid Research. 6:1968;1 Academic Press, New Yolk
27. Laemmli U.K. Cleavage of structural proteins during assembly of the head of bacteriophage T4. Nature. 227:1970;680-685
28. Kelly G.E., Nelson C., Waring M.A., Joannou G.E., Reeder A.Y. Metabolites of dietary (soya) isoflavones in human urine. Clin. Chim. Acta. 223:1993;9-22
29. Sfakianos J., Coward L., Kirk M., Barnes S. Intestinal uptake and biliary excretion of the isoflavone genistein in rats. J. Nutr. 127:1997;1260-1268
30. Fang N., Yu S., Badger T.M. Characterization of isoflavones and their conjugates in female rat urine using LC/MS/MS. J. Agric. Food Chem. 24:2002;2700-2707
31. Nimpf J., Schneider W.J. Receptor-mediated lipoprotein transport in laying hens. J. Nutr. 121:1991;1471-1474
32. 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. 47:1999;3764-3770
33. Munro S.S., Kosin I.L. The relative potency of several estrogenic compounds tested on baby chicks of both sexes. Endocrinology. 27:1940;687-692
34. Raymoure W.J., McNaught R.W., Smith R.G. Reversible activation of non-steroid binding oestrogen receptor. Nature. 314:1985;745-747
35. Wakai K., Egami I., Kato K., Kawamura T., Tamakoshi A., Lin Y., Nakayama T., Wada M., Ohno Y. Dietary intake and sources of isoflavones among Japanese. Nutr. Cancer. 33:1999;139-145
36. Pratt D.E., Birac P.M. Source of antioxidant activity of soybeans and soy products. J. Food Sci. 44:1979;1720-1722
37. Eldridge A.C., Kwolek W.F. Soybean isoflavones: effect of environment and variety on composition. J. Agric. Food Chem. 31:1983;394-396
38. Antignac J.P., Cariou R., Bizec B.L., Cravedi J.P., Andre F. Identification of phytoestrogens in bovine milk using liquid chromatography/electrospray tandem mass spectrometry. Rapid Commun. Mass. Spectrom. 17:2003;1256-1264