Phytoestrogens

Annual Review of Plant Biology

Volumn 55, Issue , 2004, Pages 225-261

  Dixon, Richard A ^a,b  

^a PLANT BIOLOGY DIVISION   (United States)

^b UNIVERSITY OF YORK   (United Kingdom)

Author keywords

Flaxseed; Isoflavone; Lignan; Nutraceutical; Soybean

Indexed keywords

FLAVONOID; LIGNAN; PHYTOESTROGEN;

CLASSIFICATION; DIET; FOOD ANALYSIS; HUMAN; METABOLISM; PLANT; PLANT PHYSIOLOGY; REVIEW;

DIET; FLAVONOIDS; FOOD ANALYSIS; HUMANS; LIGNANS; PHYTOESTROGENS; PLANT PHYSIOLOGY; PLANTS;

GLYCINE MAX; MAMMALIA;

EID: 3242683502     PISSN: 15435008     EISSN: None     Source Type: Book Series    
DOI: 10.1146/annurev.arplant.55.031903.141729     Document Type: Review

References (205)

1. Adeoya-Osiguwa SA, Markoulaki S, Pocock V, Milligan SR, Fraser LR. 2003. 17β-Estradiol and environmental estrogens significantly affect mammalian sperm function. Hum. Reprod. 18:100-7
2. Adlercreutz H. 1998. Human Health and Phytoestrogens. In Reproductive Toxicology and Development, ed. KS Korach, pp. 299-371. Research Triangle Park: Marcel Dekker
3. Adlercreutz H. 2002. Phyto-oestrogens and cancer. Lancet Oncol, 3:364-73
4. Adlercreutz H, Mazur W. 1997. Phytoestrogens and Western diseases. Ann. Med. 29:95-120
5. Adlercreutz H, Mazur W, Stumpf K, Kilkkinen A, Pietinen P, et al. 2000. Food containing phytoestrogens, and breast cancer. BioFactors 12:89-93
6. Adlercreutz H, Yamada T, Wahala K, Watanabe S. 1999. Maternal and neonatal phytoestrogens in Japanese women during birth. Am. J. Obstet. Gynecol. 180: 737-43
7. Adlercreutz M. 1998. Epidemiology of phytoestrogens. Baillieres Clin. Endocrinol. Metab. 12:605-23
8. Akashi T, Aoki T, Ayabe S. 1999. Cloning and functional expression of a cytochrome P450 cDNA encoding 2-hydroxyisoflavanone synthase involved in biosynthesis of the isoflavonoid skeleton in licorice. Plant Physiol. 121:821-28
9. Akashi T, Sawada Y, Shimada N, Sakurai N, Aoki T, Ayabe S. 2003. cDNA cloning and biochemical characterization of S-adenosyl-L-methionine: 2,7,4′-trihydroxyisoflavanone 4′-O-methyltransferase, a critical enzyme of the legume isoflavonoid phytoalexin pathway. Plant Cell Physiol. 44:103-12
10. Albert A, Altabre C, Baro F, Buendia E, Cabero A., et al. 2002. Efficacy and safety of a phytoestrogen preparation derived from Glycine max (L.) Merr in climacteric symptomatology: A multicentric, open, prospective and non-randomized trial. Phytomedicine (Jena) 9:85-92
11. Albertazzi P, Pansini F, Bonaccorsi G, Zanotti L, Forini E, De Aloysio D. 1998. The effect of dietary soy supplementation on hot flushes. Obstet. Gynecol. 91:6-11
12. Alekel DL, Germain A St., Pererson CT, Hanson KB, Stewart JW, Toda T. 2000. Isoflavone-rich soy protein isolate attenuates bone loss in the lumbar spine of perimenopausal women. Am. J. Clin. Nutr. 72:844-52
13. An J, Tzagarakis FC, Scharschmidt TC, Lomri N, Leitman DC. 2001. Estrogen receptor β-selective transcriptional activity and recruitment of coregulators by phytoestrogens. J. Biol. Chem. 276:17808-14
14. Ashby J, Tinwell H, Pennie W, Brooks AN, Lefevre PA, et al. 1999. Partial and weak oestrogenicity of the red wine constituent resveratrol: consideration of its superagonist activity in MCF-7 cells and its suggested cardiovascular protective effects. J. Appl. Toxicol. 19:39-45
15. Baker VA, Hepbum PA, Kennedy SJ, Jones PA, Lea LJ, et al. 1999. Safety evaluation of phytosterol esters. Part 1. Assessment of oestrogenicity using a combination of in vivo and in vitro assays. Food Chem. Toxicol. 37:13-22
16. Balk JL, Whiteside DA, Naus G, DeFerrari E, Roberts JM. 2002. A pilot study of the effects of phytoestrogen supplementation on postmenopausal endometrium. J. Soc. Gynecol. Invest. 9:238-42
17. Barnes S, Coward L, Kirk M, SfakianosJ. 1998. HPLC-mass spectrometry analysis of isoflavones. Proc. Soc. Exp. Biol. Med. 217:254-62
18. Benlhabib E, Baker JI, Keyler DE, Singh AK. 2002. Composition, red blood cell uptake, and serum protein binding of phytoestrogens extracted from commercial kudzu-root and soy preparations. J. Med. Food 5:109-23
19. Bennetau PC, Houerou C, Lamothe V, Menn F, Babin P, Bennetau B. 2000. Synthesis of haptens and conjugates for ELISAs of phytoestrogens. Development of the immunological tests. J. Agric. Food Chem. 48:305-11
20. Bhathena SJ, Velasquez MT. 2002. Beneficial role of dietary phytoestrogens in obesity and diabetes. Am. J. Clin. Nutr. 76:1191-201
21. Bielenberg J. 2001. Isoflavonoids from licorice root as mediators of antiinflammatory and anti-allergic effects. Z. Phytotherapie 22:289-93
22. Biendl M. 2002. The contents of xanthohumol and 8-prenylnaringenin in hop cones and hop products. Hmeljarski Bitten. 9:27-34
23. Boller B. 1996. Formica, a persistent red clover ("Mattenklee" type) with a reduced phytoestrogen content. Agrarforschung (Switzerland) 3:486-88
24. Bowers JL, Tyulmenkov W, Jernigan SC, Klinge CM. 2000. Resveratrol acts as a mixed agonist/antagonist for estrogen receptors α and β. Endocrinology 141:3657-67
25. Burke BE, Olson RD, Cusack BJ. 2002. Randomized, controlled trial of phytoestrogen in the prophylactic treatment of menstrual migraine. Biomed. Pharmacother. 56:283-88
26. Chan RYK, Chen WF, Dong A, Guo D, Wong MS. 2002. Estrogen-like activity of ginsenoside Rg1 derived from Panax notoginseng. J. Clin. Endocrinol. Metab. 87:3691-95
27. Chansakaow S, Ishikawa T, Seki H, Sekine K, Okada M, Chaichantipyuth C. 2000. Identification of deoxymiroestrol as the actual rejuvenating principle of "Kwao Keur," Pueraria mirifica. The known miroestrol may be an artifact. J. Nat. Prod. 63:173-75
28. Chen CC, Shieh B, Jin YT, Liau YE, Huang CH, et al. 2001. Microarray profiling of gene expression patterns in bladder tumor cells treated with genistein. J. Biomed. Sci. 8:214-22
29. 13C3)-isoflavone internal standards. Anal. Biochem. 309:158-72
30. Clarkson TB, Anthony MS, Morgan TM. 2001. Inhibition of postmenopausal atherosclerosis progression: A comparison of the effects of conjugated equine estrogens and soy phytoestrogens. J Clin. Endocrinol. Metab. 86:41-47
31. Coldham NG, Howells LC, Santi A, Montesissa C, Langlais C, et al. 1999. Biotransformation of genistein in the rat: elucidation of metabolite structure by product ion mass fragmentology. J. Steroid Biochem. Mol. Biol. 70:169-84
32. Coldham NG, Sauer MJ. 2001. Identification, quantitation and biological activity of phytoestrogens in a dietary supplement for breast enhancement. Food Chem. Toxicol. 39:1211-24
33. Cotroneo MS, Wang J, Fritz WA, Eltoum IE, Lamartiniere CA. 2002. Genistein action in the prepubertal mammary gland in a chemoprevention model. Carcinogenesis 23:1467-74
34. Dabrosin C, Chen J, Wang L, Thompson LU. 2002. Flaxseed inhibits metastasis and decreases extracellular vascular endothelial growth factor in human breast cancer xenografts. Cancer Lett. 185:31-37
35. Dai Q, Franke AA, Jin F, Shu XO, Hebert JR, et al. 2002. Urinary excretion of phytoestrogens and risk of breast cancer among Chinese women in Shanghai. Cancer Epidemiol. Biomarkers Prev. 11:815-21
36. Davin LB, Wang H-B, Crowell AL, Bedgar DL, Martin DM, et al. 1997. Stereoselective bimolecular coupling by an auxiliary (dirigent) protein without an active center. Science 275:362-66
37. Davis JN, Kucuk O, Sarkar FH. 2002. Expression of prostate-specific antigen is transcriptionally regulated by genistein in prostate cancer cells. Mol. Carcinogen. 34:91-101
38. Day AJ, Canada FJ, Diaz JC, Kroon PA, Mclauchlan R, et al. 2000. Dietary flavonoid and isoflavone glycosides are hydrolysed by the lactase site of lactase phlorizin hydrolase. FEBS Lett. 468:166-70
39. Day JK, Bauer AM, des Bordes C, Zhuang Y, Kim BE, Newton LG, et al. 2002. Genistein alters methylation patterns in mice. J. Nutr. 132:24198-328
40. de Lemos ML. 2001. Effects of soy phytoestrogens genistein and daidzein on breast cancer growth. Ann. Pharmacother. 35:1118-21
41. Degen GH, Janning P, Diel P, Michna H, Bolt HM. 2002. Transplacental transfer of the phytoestrogen daidzein in DA/Han rats. Arch. Toxicol. 76:23-29
42. denTonkelaar I, KeinanBoker L, VantVeer P, Arts CJM, Adlercreutz H, et al. 2001. Urinary phytoestrogens and post-menopausal breast cancer risk. Cancer Epidemiol. Biomarkers Prev. 10:223-28
43. Dewell A, Hollenbeck CB, Bruce B. 2002. The effects of soy-derived phytoestrogens on serum lipids and lipoproteins in moderately hypercholesterolemic post-menopausal women. J. Clin. Endocrinol. Metab. 87:118-21
44. Dewick PM. 1994. The isoflavonoids. In The Flavonoids. Advances in Research Since 1986, ed. JB Harborne, pp. 117-238. London: Chapman and Hall
45. Dewick PM, Martin M. 1979. Biosynthesis of pterocarpan, isoflavan and coumestan metabolites of Medicago sativa: chalcone, isoflavone and isoflavanone precursors. Phytochemistry 18:597-602
46. Diel P, Olff S, Schmidt S, Michna H. 2001. Molecular identification of potential selective estrogen receptor modulator (SERM) like properties of phytoestrogens in the human breast cancer cell line MCF-7. Planta Med. 67:510-14
47. Diel P, Schmidt S, Vollmer G. 2002. In vivo test systems for the quantitative and qualitative analysis of the biological activity of phytoestrogens. J. Chromatogr. B 777:191-202
48. Dixon RA. 1999. Isoflavonoids: biochemistry, molecular biology and biological functions. In Comprehensive Natural Products Chemistry, ed. U Sankawa, pp. 773-823. Oxford: Elsevier
49. Dobrydneva Y, Williams RL, Morris GZ, Blackmore PF. 2002. Dietary phytoestrogens and their synthetic structural analogue as calcium channel blockers in human platelets. J. Cardiovasc. Pharmacol. 40:399-410
50. Domon OE, McGarrity LJ, Bishop M, Yoshioka M, Chen JJ, Morris SM. 2001. Evaluation of the genotoxicity of the phytoestrogen, coumestrol, in AHH-1 TK+/- human lymphoblastoid cells. Mutat. Res. 474:129-37
51. Duke SO, Rimando AM, Pace PF, Reddy KN, Smeda RJ. 2003. Isoflavone, glyphosate, and aminomethylphosphonic acid levels in seeds of glyphosate-treated, glyphosate-resistant soybean. J. Agric. Food Chem. 51:340-44
52. Ebisawa H, Koshihara Y. 2001. Inhibitory effects of soy-isoflavones on osteoclasto-genesis in human bone marrow cell culture. Soy Protein Res. (Japan) 4:129-34
53. Edwards R, Dixon RA. 1991. Isoflavone O-methyltransferase activities in elicitor-treated cell suspension cultures of Medicago sativa. Phytochemistry 30:2597-606
54. Eldridge AC, Kwolek WF. 1983. Soybean isoflavones: effect of environment and variety on composition. J. Agric. Food Chem. 31:394-96
55. Fanti P, Monier-Faugere MC, Geng Z, Schmidt J, Morris PE, et al. 1998. The phytoestrogen genistein reduces bone loss in short-term ovariectomized rats. Osteoporos. Int. 8:274-81
56. Ferrer J-L, Jez JM, Bowman ME, Dixon RA, Noel JP. 1999. Structure of chalcone synthase and the molecular basis of plant polyketide biosynthesis. Nat. Struct. Biol. 6:775-84
57. File SE, Jarrett N, Fluck E, Duffy R, Casey K, Wiseman H. 2001. Eating soya improves human memory. Psychopharmacology 157:430-36
58. Franke AA, Hankin JH, Yu MC, Maskarinec G, Low SH, Custer LJ. 1999. Isoflavone levels in soy foods consumed by multiethnic populations in Singapore and Hawaii. J. Agric. Food Chem. 47:977-86
59. Fritz WA, Coward L, Wang J, Lamartiniere CA. 1998. Dietary genistein: perinatal mammary cancer prevention, bioavailability and toxicity testing in the rat. Carcinogenesis 19:2151-58
60. Fritz WA, Eltoum IE, Cotroneo MS, Lamartiniere CA. 2002. Genistein alters growth but is not toxic to the rat prostate. J. Nutr. 132:3007-11
61. Fugh-Berman A, Kronenberg F. 2001. Red clover (Trifolium pratense) for menopausal women: current state of knowledge. Menopause. 8:333-37
62. Gallo D, Giacomelli S, Cantelmo F, Zannoni GF, Ferrandina G, et al. 2001. Chemoprevention of DMBA-induced mammary cancer in rats by dietary soy. Breast Cancer Res. Treat. 69:153-64
63. Gang DR, Kasahara H, Xia ZQ, Mijnsbrugge KV, Bauw G, et al. 1999. Evolution of plant defense mechanisms: relationships of phenylcoumaran benzylic ether reductases to pinoresinollariciresinol and isoflavone reductases. J. Biol. Chem. 274:7516-27
64. Ganry O. 2002. Phytoestrogen and breast cancer prevention. Eur. J. Cancer Prev. 11:519-22
65. Garrett SD, Lee HA, Friar PMK, Morgan MRA. 1999. Validation of a novel estrogen receptor-based microtitration plate assay for the determination of phytoestrogens in soy-based foods. J. Agric. Food Chem. 47:4106-11
66. Gee JM, Noteborn HPJM, Policy ACJ, Johnson IT. 2000. Increased induction of aberrant crypt foci by 1,2-dimethylhydrazine in rats fed diets containing purified genistein or genistein-rich soya protein. Carcinogenesis 21:2255-59
67. Gehm BD, McAndrews JM, Chien PY, Jameson JL. 1997. Resveratrol, a polyphenolic compound found in grapes and wine, is an agonist for the estrogen receptor. Proc. Natl. Acad. Sci. USA 94:14138-43
68. Glazier MG, Bowman MA. 2001. A review of the evidence for the use of phytoestrogens as a replacement for traditional estrogen replacement therapy. Arch. Intern. Med. 161:1161-72
69. Guo TL, McCay JA, Zhang LX, Brown RD, You L, et al. 2001. Genistein modulates immune responses and increases host resistance to B16F10 tumor in adult female B6C3F1 mice. J. Nutr. 131:3251-58
70. Guo TL, White KLJ, Brown RD, Delclos KB, Newbold RR, et al. 2002. Genistein modulates splenic natural killer cell activ-ity, antibody-forming cell response, and phenotypic marker expression in FO and Fl generations of Sprague-Dawley rats. Toxicol. Appl. Pharmacol. 181:219-27
71. Hagmann M, Grisebach H. 1984. En-zymatic rearrangement of flavanone to isoflavone. FEBS Lett. 175:199-202
72. Hedlund TE, Johannes WU, Miller GJ. 2003. Soy isoflavonoid equol modulates the growth of benign and malignant pro-static epithelial cells in vitro. Prostate 54:68-78
73. Henderson MC, Miranda CL, Stevens JF, Deinzer ML, Buhler DR. 2000. In vitro inhibition of human P450 enzymes by prenylated flavonoids from hops, Humulus lupulus. Xenobiotica. 30:235-51
74. Hertog MGL, Feskens EJM, Hollman PCH, Katan MB, Kromhout D. 1993. Dietary antioxidant flavonols and risk of coronary heart disease - the Zutphen elderly study. Lancet 342:1007-11
75. Heyerick A, de Keukeleire D, van Peteghem C, Saeger S. 2002. Modulation of the phytoestrogenicity of beer by monoterpene alcohols present in various hop oil fractions. J. Inst. Brewing 108:94-101
76. Hodgson JM, Puddey IB, Beilin LJ, Mori TA, Croft KD. 1998. Supplementation with isoflavonoid phytoestrogens does not alter serum lipid concentrations: A randomized controlled trial in humans. J. Nutr. 128:728-32
77. Hoeck JA, Fehr WR, Murphy PA, Welke GA. 2000. Influence of genotype and environment on isoflavone contents of soybean. Crop Sci. 40:48-51
78. Horn-Ross PL, Barnes S, Lee M, Coward L, Mandel JE, et al. 2000. Assessing phytoestrogen exposure in epidemiologic studies: development of a database (United States). Cancer Causes Control 11:289-98
79. Horn-Ross PL, Hogatt KJ, Lee MM. 2002. Phytoestrogens and thyroid cancer risk: The San Francisco Bay Area thyroid cancer study. Cancer Epidemiol. Biomarkers Prev. 11:43-49
80. Hsu JT, Hsu WL, Ying C. 1999. Dietary phytoestrogen regulates estrogen receptor gene expression in human mammary carcinoma cells. Nutr. Res. 19:1447-57
81. Hsu JT, Hung HC, Chen CJ, Hsu WL, Ying CW. 1999. Effects of the dietary phytoestrogen biochanin A on cell growth in the mammary carcinoma cell line MCF-7. J. Nutr. Biochem. 10:510-17
82. Hwang JL, Hodis HN, Sevanian A. 2001. Soy and alfalfa phytoestrogen extracts become potent low-density lipoprotein antioxidants in the presence of acerola cherry extract. J. Agric. Food Chem. 49:308-14
83. ILDIS 1994. Phytochemical Dictionary of the Leguminosae. Vol. 1, Plants and their Constituents eds. FA Bisby, J Buckingham, JB Harborne. London: Chapman and Hall
84. Irvine CHG, Fitzpatrick MG, Alexander SL. 1998. Phytoestrogens in soy-based infant foods: Concentrations, daily intake, and possible biological effects. Proc. Soc. Exp. Biol. Med. 3:247-53
85. Ishimi Y, Miyaura C, Ohmura M, Onoe Y, Sato T, et al. 1999. Selective effects of genistein, a soybean isoflavone, on B-lymphopoiesis and bone loss caused by estrogen deficiency. Endocrinology 140:1893-900
86. Jacobs DRJ, Pereira MA, Stumpf K, Pins JJ, Adlercreutz H. 2002. Whole grain food intake elevates serum enterolactone. Br. J. Nutr. 88:111-16
87. Jang M, Cai L, Udeani GO, Slowing KV, Thomas CF, et al. 1997. Cancer chemopreventive activity of resveratrol, a natural product derived from grapes. Science 275:218-20
88. Jefferson A. 2003. Dietary phytoestrogens - a role in women's health. Nutr. Food Sci. 33:16-22
89. Jefferson WN, Couse JF, Padilla BE, Korach KS, Newbold RR. 2002. Neonatal exposure to genistein induces estrogen receptor (ER) α expression and multioocyte follicles in the maturing mouse ovary: Evidence for ERβ-mediated and none-strogenic actions. Biol. Reprod. 67:1285-96
90. Jenkins DJA, Kendall CWC, Connelly PW, Jackson CJC, Parker T, et al. 2002. Effects of high- and low-isoflavone (phytoestrogen) soy foods on inflammatory biomarkers and proinflammatory cytokines in middle-aged men and women. Metab. Clin. Exp. 51:919-24
91. Jez JM, Austin MB, Ferrer J-L, Bowman ME, Schröder J, Noel JP. 2000. Structural control of polyketide formation in plant-specific polyketide synthesis. Chem. Biol. 7:919-30
92. Jung W, Yu O, Lau S-MC, O'Keefe DP, Odell J, et al. 2000. Identification and expression of isoflavone synthase, the key enzyme for biosynthesis of isoflavones in legumes. Nat. Biotechnol. 18:208-12
93. Kao YC, Zhou C, Sherman M, Laughton CA, Chen S. 1998. Molecular basis of the inhibition of human aromatase (estrogen synthetase) by flavone and isoflavone phytoestrogens: a site-directed mutagenesis study. Environ. Health Perspect. 106:85-92
94. Kennelly EJ, Baggert S, Nuntanakorn P, Ososki AL, Mod SA, et al. 2002. Analysis of thirteen populations of black cohosh for formononetin. Phytomedicine 9:461-67
95. Kilkkinen A, Pietinen P, Klaukka T, Virtamo J, Korhonen P, Adlercreutz H. 2002. Use of oral antimicrobials decreases serum enterolactone concentration. Am. J. Epidemiol. 155:472-77
96. Kim CS, Lee YS. 2000. High performance liquid chromatographic analysis of isoflavones in soybean foods. Kor. J. Food Sci. Technol. 32:25-30
97. Kim HJ, Bae YC, Park RW, Choi SW, Cho SH, et al. 2002. Bone-protecting effect of safflower seeds in ovariectomized rats. Calcif. Tissue Int. 71:88-94
98. Kim MK, Jeon J-H, Davin LB, Lewis NG. 2002. Monolignol radical-radical coupling networks in western red cedar and Arabidopsis and then- evolutionary implications. Phytochemistry 61:311-22
99. de Kleijn MJJ, van der Schouw YT, Wilson PWF, Grobbee DE, Jacques PF. 2002. Dietary intake of phytoestrogens is associated with a favorable metabolic cardiovascular risk profile in postmenopausal U.S. women: The Framingham Study. J. Nutr. 132:276-82
100. Kochs G, Grisebach H. 1986. Enzymic synthesis of isoflavones. Eur. J. Biochem. 155:311-18
101. Koester J, Bussmann R, Barz W. 1984. Malonyl-coenzyme A: isoflavone 7-O-glucoside-6″-O-malonyltransferase from roots of chick pea (Cicer arietinum L.). Arch. Biochem. Biophys. 234:513-21
102. Köster J, Barz W. 1981. UDP-Glucose: isoflavone 7-O- glucosyltransferase from roots of chick pea (Cicer arietinum L.). Arch. Biochem. Biophys. 212:98-104
103. Kraushofer T, Sontag G. 2002. Determination of mataiiesinol in flax seed by HPLC with coulometric electrode array detection. J. Chromatogr. B 777:61-66
104. Kulling SE, Rosenberg B, Jacobs E, Metzler M. 1999. The phytoestrogens coumoestrol and genistein induce structural chromosomal aberrations in cultured human peripheral blood lymphocytes. Arch. Toxicol. 73:50-54
105. Kwon SM, Kim SI, Chun DC, Cho NH, Chung BC, et al. 2001. Development of rat prostatitis model by oral administration of isoflavone and its characteristics. Yonsei Med. J. 42:395-404
106. Lamartiniere CA. 2000. Protection against breast cancer with genistein: a component of soy. Am. J. Clin. Nutr. 71:1705S-7S
107. Lamartiniere CA, Wang J, Smith JM, Eltoum IE. 2002. Daidzein: bioavailability, potential for reproductive toxicity, and breast cancer chemoprevention in female rats. Toxicol. Sci. 65:228-38
108. Lampe JW, Karr SC, Hutchins AM, Slavin JL. 1998. Urinary equol excretion with a soy challenge: influence of habitual diet. PTOC. Soc. Exp. Biol. Med. 3:335-39
109. Lee HP, Gourley L, Duffy SW, Esteve J, Lee J, Day NE. 1991. Dietary effects on breast-cancer risk in Singapore. Lancet 337:1197-200
110. Lee S-J, Chung H-Y, Maier CG-A, Wood AR, Dixon RA, Mabry TJ. 1998. Estrogenic flavonoids from Artemesia vulgaris L. J. Agric. Food Chem. 46:3325-29
111. Lee S-J, Wood AR, Maier CG-A, Dixon RA, Mabry TJ. 1998. Prenylated flavonoids from Maclura pomifera. Phytochemistry 49:2573-77
112. Lee YS, Chen X, Anderson JJB. 2001. Physiological concentrations of genistein stimulate the proliferation and protect against free radical-induced oxidative damage of MC3T3-E1 osteoblast-type cells. Nutr. Res. 21:1287-98
113. Lemay A, Dodin S, Kadri N, Jacques H, Forest JC. 2002. Flaxseed dietary supplement versus hormone replacement therapy in hypercholesterolemic menopausal women. Obstet. Gynecol. 100:495-504
114. Leopold AS, Erwin M, Oh J, Browning B. 1976. Phytoestrogens: adverse effects on reproduction in California quail. Science 191:98-100
115. Lephart ED, West TW, Weber KS, Rhees RW, Setchell KDR, et al. 2002. Neurobehavioral effects of dietary soy phytoestrogens. Neurotoxicol. Teratol. 24:5-16
116. Lewis NG, Davin LB. 1999. Lignons: Biosynthesis and Function, In Comprehensive Natural Products Chemistry Vol. L, ed. U Sankawa, pp. 639-712, Oxford: Elsevier
117. L'-Homme R, Brouwers E, Al-Maharik N, Lapcik O, Hampl R, et al. 2002. Time-resolved fluoroimmunoassay of plasma and urine O-desmethylangolensin. J. Steroid Biochem. Mol. Biol. 81:353-61
118. Linford NJ, Dorsa DM. 2002. 17β-Estradiol and the phytoestrogen genistein attenuate neuronal apoptosis induced by the endoplasmic reticulum calcium-ATPase inhibitor thapsigargin. Steroids 67:1029-40
119. Liu C-J, Blount JW, Steele CL, Dixon RA. 2002. Bottlenecks for metabolic engineering of isoflavone glycoconjugates in Arabidopsis. Proc. Natl. Acad. Sci. USA 99:14578-83
120. Liu C-J, Dixon RA. 2001. Elicitor-induced association of isoflavone O-methyltransferase with endomembranes prevents formation and 7-O-methylation of daidzein during isoflavonoid phytoalexin biosynthesis. Plant Cell 13:2643-58
121. Lund TD, Lephart ED. 2001. Manipulation of prenatal hormones and dietary phytoestrogens during adulthood alter the sexually dimorphic expression of visual spatial memory. BMC Neurosci. (online) 2:1-7
122. Lund TD, West TW, Tian LY, Bu LH, Simmons DL, et al. 2001. Visual spatial memory is enhanced in female rats (but inhibited in males) by dietary soy phytoestrogens. BMC Neurosci. (online) 2:1-13
123. Maggiolini M, Bonofiglio D, Marsico S, Panno ML, Cenni B, et al. 2001. Estrogen receptor α mediates the proliferative but not the cytotoxic dose-dependent effects of two major phytoestrogens on human breast cancer cells. Mol. Pharmacol. 60:595-602
124. Maier CG-A, Chapman KD, Smith DW 1995. Differential estrogenic activities of male and female plant extracts from two dioecious species. Plant Sci. 109:31-43
125. Markaverich B, Mani S, Alejandro MA, Mitchell A, Markaverich D, et al. 2002. A novel endocrine-disrupting agent in corn with mitogenic activity in human breast and prostatic cancer cells. Environ. Health Perspect. 110:169-77
126. Markaverich BM, Alejandro MA, Markaverich D, Zitzow L, Casajuna N, et al. 2002. Identification of an endocrine disrupting agent from corn with mitogenic activity. Biochem. Biophys. Res. Commun. 291:692-700
127. Maskarinec G, Williams AE, Inouye JS, Stanczyk FZ, Franke AA. 2002. A randomized isoflavone intervention among premenopausal women. Cancer Epidemiol. Biomarkers Prev. 11:195-201
128. Matsuda H, Shimoda H, Morikawa T, Yoshikawa M. 2001. Phytoestrogens from the roots of Polygonum cuspidatum (Polygonaceae): structure-requirement of hydroxyanthraquinones for estrogenic activity. Bioorg. Med. Chem. Lett. 11:1839-42
129. Mazur W. Adlercreutz H. 1998. Naturally occurring oestrogens in food. Pure Appl. Chem. 70:1759-76
130. McCann SE, Moysich KB, Freudenheim JL, Ambrosone CB, Shields PG. 2002. The risk of breast cancer associated with dietary lignans differs by CYP17 geno-type in women. J. Nutr. 132:3036-41
131. Mei J, Yeung SSC, Kung AWC. 2001. High dietary phytoestrogen intake is associated with higher bone mineral density in postmenopausal but not pre-menopausal women. J. Clin. Endocrinol. Metab. 86:5217-21
132. Mentor MR, Lamartiniere CA, Eltomn IE, Greenberg NM, Elgavish A. 2001. Genistein in the diet reduces the incidence of poorly differentiated prostatic adeno-carcinoma in transgenic mice (TRAMP). Cancer Res. 61:6777-82
133. MerzDemlow BE, Duncan AM, Wangen KE, Xu X, Carr TP, et al. 2000. Soy isoflavones improve plasma lipids in normocholesterolemic, premenopausal women. Am. J. Clin. Nutr. 71:1462-69
134. Miller-Martini DM, Chan RYK, Ip NY, Sheu SJ, Wong YH. 2001. A reporter gene assay for the detection of phytoestrogens in traditional Chinese medicine. Phytotherapy Res. 15:487-92
135. Milligan S, Kalita J, Pocock V, Heyerick A, de Cooman L, et al. 2002. Oestrogenic activity of the hop phyto-oestrogen, 8-prenylnaringenin. Reproduction (Cambridge) 123:235-42
136. Milligan SR, Kalita JC, Heyerick A, Rong H, de Cooman L, de Keukeleire D. 1999. Identification of a potent phytoestrogen in hops (Humulus lupulus L.) and beer. J. Clin. Endocrinol. Metab. 84:2249-52
137. Mitchell JH, Cawood E, Kinniburgh D, Provan A, Collins AR, Irvine DS. 2001. Effect of a phytoestrogen food supplement on reproductive health in normal males. Clin. Sci. London 100:613-18
138. Miyamoto M, Matsushita Y, Kikokawa A, Fukuda C, Iijima Y, et al. 1998. Prenylflavonoids: A new class of non-steroidal phytoestrogen (Part 2). Estrogenic effects of 8-isopentenylnaringenin on bone metabolism. Planta Med. 64:516-19
139. Mizutani K, Keda K, Kawai Y, Yamori Y. 2001. Protective effect of resveratrol on oxidative damage in male and female stroke-prone spontaneously hypertensive rats. Clin. Exp. Pharmacol. Physiol. 28:55-59
140. Morabito N, Crisafulli A, Vergara C, Gaudio A, Lasco A, et al. 2002. Effects of genistein and hormone-replacement therapy on bone loss in early postmenopausal women: a randomized double-blind placebo-controlled study. J. Bone Miner. Res. 17:1904-12
141. Naciff JM, Jump ML, Torontali SM, Carr GJ, Tiesman JP, et al. 2002. Gene expression profile induced by 17α-ethynyl estradiol, bisphenol A, and genistein in the developing female reproductive system of the rat. Toxicol. Sci. 68:184-99
142. Nakajima N, Ishihara K, Hamada H. 2001. Functional glucosylation of kojic acid and daidzein with the Eucalyptus membrane-associated UDP- glucosyltransferase reaction system. J. Biosci. Bioeng. 92:469-71
143. Nelsen J, Barrette EP, Tsouronis C, Basch S, Bent S, et al. 2002. Red clover (Trifolium pratense) monograph: a clinical decision support tool. J. Herb. Pharmacotherapy 2:49-72
144. Newbold RR, Banks EP, Bullock B, Jefferson WN. 2001. Uterine adenocarcinoma in mice treated neonatally with genistein. Cancer Res. 61:4325-28
145. Nogowski L. 1999. Effects of phytoestrogen coumestrol on lipid and carbohydrate metabolism in young ovariectomized rats may be independent of its estrogenicity. J. Nutr. Biochem. 10:664-69
146. Okazaki K, Okazaki S, Nakamura H, Kitamura Y, Hatayama K, et al. 2002. A repeated 28-day oral dose toxicity study of genistein in rats, based on the 'Enhanced OECD Test Guideline 407' for screening endocrine-disrupting chemicals. Arch. Toxicol. 76:553-59
147. Pagano L, Teofili L, Mele L, Piantelli M, Ranelletti FO, et al. 1999. Oral ipriflavone (7-isopropoxy-isoflavone) treatment for elderly patients with resistant acute leukemias. Ann. Oncol. 10:124-25
148. Pan W, Ikeda K, Takebe M, Yamori Y. 2001. Genistein, daidzein and glycitein inhibit growth and DNA synthesis of aortic smooth muscle cells from stroke-prone spontaneously hypertensive rats. J. Nutr. 131:1154-58
149. Peluso MR, Winters TA, Shanahan MF, Banz WJ. 2000. A cooperative interaction between soy protein and its isoflavone-enriched fraction lowers hepatic lipids in male obese Zucker rats and reduces blood platelet sensitivity in male Sprague-Dawley rats. J. Nutr. 130:2333-42
150. Pillow PC, Duphorne CM, Shine C, Contois JH, Strom SS, et al. 1999. Development of a database for assessing dietary phytoestrogen intake. Nutr. Cancer 33:3-19
151. Pino AM, Valladares LE, Palma MA, Mancilla AM, Yanez M, Albala C. 2000. Dietary isoflavones affect sex hormone-binding globulin levels in postmenopausal women. J. din. Endocrinol. Metab. 85:2797-800
152. Pocock VJ, Sales GD, Milligan SR. 2002. Comparison of the oestrogenic effects of infant milk formulae, oestradiol and the phytoestrogen coumestrol delivered continuously in the drinking water to ovariectomised mice. Food Chem. Toxicol. 40:643-51
153. Preisig CL, VanEtten HD, Moreau RA. 1991. Induction of 6a-hydroxymaackiain 3-0-methyltransferase and phenylalanine ammonia-lyase mRNA translational activities during the biosynthesis of pisatin. Arch. Biochem. Biophys. 290:468-73
154. Rassi CM, Lieberherr M, Chaumaz G, Pointillart A, Cournot G. 2002. Down-regulation of osteoclast differentiation by daidzein via caspase. J. Bone Miner. Res. 17:630-38
155. Regal JF, Fraser DG, Weeks CE, Greenberg NA. 2000. Dietary phytoestrogens have anti-inflammatory activity in a guinea pig model of asthma. Proc. Soc. Exp. Biol. Med. 223:372-78
156. Reinli K, Block G. 1996. Phytoestrogen content of foods - a compendium of literature values. Nutr. Cancer 26:123-48
157. Rice-Evans CA, Miller NJ. 1996. Antioxidant activities of flavonoids as bioactive components of food. Biochem. Soc. Trans. 24:790-94
158. Roberts D, Rao VDN, Schlaff WD, Awoniyi CA. 2000. Effects of chronic dietary exposure to genistein, a phytoestrogen, during various stages of development on reproductive hormones and spermatogenesis in rats. Endocrine 13:281-86
159. Sarkar FH, Li Y. 2002. Mechanisms of cancer chemoprevention by soy isoflavone genistein. Cancer Metastasis Rev. 21:265-80
160. Saxena VK, Bhadoria BK. 1990. 3′-Prenyl-4′-methoxyisoflavone 7-O-beta-D-(2"-O-p-coumaroyl")glucopyranoside, a novel phytoestrogen from Sopubia delphinifolia. J. Nat. Prod. 53:62-65
161. Schmitt E, Stopper H. 2001. Estrogenic activity of naturally occurring anthocyanidins. Nutr. Cancer 41:145-49
162. Schröder J. 1997. A family of plant-specific polyketide synthases: facts and predictions. Trends Plant Sci. 2:373-78
163. Seested S, Norgaard P, Ranvig H. 2000. Factors affecting the phytoestrogen content of clover and lucerne and its influence on female fertility in ruminants. Dansk Veterinaertidsskrift 83:6-12
164. Setchell KDR, Brown NM, Desai P, Zimmer-Nechemias L, Wolfe BE, et al. 2001. Bioavailability of pure isoflavones in healthy humans and analysis of commercial soy isoflavone supplements. J. Nutr. 131:13628-758
165. Setchell KDR, Brown NM, Lydeking-Olsen E. 2002. The clinical importance of the metabolite equol - a clue to the effectiveness of soy and its isoflavones. J. Nutr. 132:3577-84
166. Setchell KDR, Cassidy A. 1999. Dietary isoflavones: biological effects and relevance to human health. J. Nutr. 129:7588-67S
167. Singletary KW, Frey RS, Li JY. 2002. Differential effects of genistein on cell proliferation, cyclin B1, and p34cdc2 in transformed and nontransformed human breast cells. Pharmaceut. Biol. 40 (suppl.):35-42
168. Slavin JL, Karr SC, Hutchins AM, Lampe JW. 1998. Influence of soybean processing, habitual diet, and soy dose on urinary isoflavonoid excretion. Am. J. Clin. Nutr. 68:1492S-5S
169. Stattin P, Adlercreutz H, Tenkanen L, Jellum E, Lumme S, et al. 2002. Circulating enterolactone and prostate cancer risk: a nordic nested case-control study. Int. J. Cancer 99:124-29
170. Steele CL, Gijzen M, Qutob D, Dixon RA. 1999. Molecular characterization of the enzyme catalyzing the aryl migration reaction of isoflavonoid biosynthesis in soybean. Arch. Biochem. Biophys. 367:147-50
171. Steensma A, Noteborn HPJM, vander-Jagt RCM, Polman THG, Mengelers MJB, Kuiper HA. 1999. Bioavailability of genistein, daidzein, and their glycosides in intestinal epithelial Caco-2 cells. Environ. Toxicol. Pharmacol. 7:209-11
172. Stevens JF, Miranda CL, Buhler DR, Deinzer ML. 1998. Chemistry and biology of hop flavonoids. J. Am. Soc. Brew. Chem. 56:136-45
173. Strom SS, Yamamura Y, Duphorne CM, Spitz MR, Babaian RJ, et al. 1999. Phytoestrogen intake and prostate cancer: a case-control study using a new database. Nutr. Cancer. 33:20-25
174. Suh D-Y, Fukuma K, Kagami J, Yamazaki Y, Shibuya M, et al. 2000.
175. Sumner LW, Mendes P, Dixon RA. 2003. Plant metabolomics: large-scale phytochemistry in the functional genomics era. Phytochemistry 62:817-36
176. Tamir S, Eizenberg M, Somjen D, Sarit I, Vaya J. 2001. Estrogen-like activity of glabrene and other constituents isolated from licorice root. J. Steroid Biochem. Mol. Biol. 78:291-298
177. Tekel J, de Keukeleire D, HaoJing R, Daeseleire E, van Peteghem C. 1999. Determination of the hop-derived phytoestrogen, 8-prenylnaringenin, in beer by gas chromatography/mass spectrometry. J. Agric. Food Chem. 47:5059-63
178. Tikkanen MJ, Adlercreutz H. 2000. Dietary soy-derived isoflavone phytoestrogens: could they have a role in coronary heart disease prevention? Biochem. Pharmacol. 60:1-5
179. Tikkanen MJ, Wahala K, Ojala S, Vihma V, Adlercreutz H. 1998. Effect of soybean phytoestrogen intake on low density lipoprotein oxidation resistance. Proc. Natl. Acad. Sci. USA 95:3106-10
180. Tinwell H, Soames AR, Foster JR, Ashby J. 2000. Estradiol-type activity of coumestrol in mature and immature ovariectomized rat uterotrophic assays. Environ. Health Perspect. 108:631-34
181. Tolleson WH, Doerge DR, Churchwell MI, Marques MM, Roberts DW. 2002. Metabolism of biochanin A and formononetin by human liver microsomes in vitro. J. Agric. Food Chem. 50:4783-90
182. den Tonkelaar I, Keinan-Boker L, Vant-Veer P, Arts CJM, Adlercreutz H, et al. 2001. Urinary phytoestrogens and post-menopausal breast cancer risk. Cancer Epidemiol. Biomarkers Prev. 10:223-28
183. Uckun FM, Evans WE, Forsyth CJ, Waddick KG, Ahlgren LT, et al. 1995. Biotherapy of B-cell precursor leukemia by targeting genistein to CD 19-associated tyrosine kinases. Science 267:886-91
184. Usui T, Ikeda Y, Tagami T, Matsuda K, Moriyama K, et al. 2002. The phytochemical lindleyin, isolated from Rhei rhizoma, mediates hormonal effects through estrogen receptors. J. Endocrinol. 175:289-96
185. van der Schouw YT, Pijpe A, Lebrun CEI, Bots ML, Peelers PHM, et al. 2002. Higher than usual dietary intake of phytoestrogens is associated with lower aortic stiffness in postmenopausal women. Arteriosclerosis Thrombosis Vascular Biol. 22:1316-22
186. Vogt T, Jones P. 2000. Glycosyltransferases in plant natural product synthesis: characterization of a supergene family. Trends Plant Sci. 5:380-86
187. Wallerath T, Deckert G, Ternes T, Anderson H, Li H, et al. 2002. Resveratrol, a polyphenolic phytoalexin present in red wine, enhances expression and activity of endothelial nitric oxide synthase. Circulation 106:1652-58
188. Wang C, Kurzer MS. 1997. Phytoestrogen concentration determines effects on DNA synthesis in human breast cancer cells. Nutr. Cancer 28:236-47
189. Wang CC, Prasain JK, Barnes S. 2002. Review of the methods used in the determination of phytoestrogens. J. Chromatog. B 777:3-28
190. Wang HJ, Murphy PA. 1994. Isoflavone content in commercial soybean foods. J. Agric. Food Chem. 42:1666-73
191. Wang LQ. 2002. Mammalian phytoestrogens: Enterodiol and enterolactone. J. Chromatogr. B 777:289-309
192. Wang W, Liu LQ, Higuchi CM, Chen H. 1998. Induction of NADPH:quinone reductase by dietary phytoestrogens in colonie colo205 cells. Biochem. Pharmacol. 56:189-95
193. Whitten PL, Lewis C, Russell E, Naftolin F. 1995. Potential adverse effects of phytoestrogens. J. Nutr. 125:771S-6S
194. Wu C, Yang Y, Yao W, Lu F, Wu J, Chang C. 2002. Epidemiological evidence of increased bone mineral density in habitual tea drinkers. Arch. Intern. Med. 162:1001-106
195. Wu SH, Ramonell K, Gollub J, Somerville S. 2001. Plant gene expression profiling with DNA microarrays. Plant Physiol. Biochem. 39:917-26
196. Yamaguchi M. 2002. Isoflavone and bone metabolism: its cellular mechanism and preventive role in bone loss. J. Health Sci. 48:209-22
197. Yamamoto H, Senda M, Inoue K. 2000. Flavanone 8-dimethylallyltransferase in Sophora flavescens cell suspension cultures. Phytochemistry 54:649-55
198. Yanagihara K, Ito A, Toge T, Numoto M. 1993. Antiproliferative effects of isoflavones on human cancer cell lines established from the gastrointestinal tract. Cancer Res. 53:5815-21
199. Yellayi S, Naaz A, Szewczykowski MS, Sato T, Woods JA, et al. 2002. The phytoestrogen genistein induces thymic and immune changes: a human health concern. Proc. Natl. Acad. Sci. USA. 99:7616-21
200. Yellayi S, Zakroczymski MA, Selvaraj V, Valli VE, Ghanta V, et al. 2003. The phytoestrogen genistein suppresses cell-mediated immunity in mice. J. Endocrinol. 176:267-74
201. Yu O, Jung W, Shi J, Croes RA, Fader GM, et al. 2000. Production of the isoflavones genistein and daidzein in non-legume dicot and monocot tissues. Plant Physiol. 124:781-94
202. Zava DT, Duwe G. 1997. Estrogenic antiproliferative properties of genistein and other flavonoids in human breast cancer cells in vitro. Nutr. Cancer 27:31-40
203. Zhang Y, Song TT, Cunnick JE, Murphy PA, 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
204. Zierau O, Gester S, Schwab P, Metz P, Kolba S, et al. 2002. Estrogenic activity of the phytoestrogens naringenin, 6-(1,1-dimethylallyl)naringenin and 8-prenylnaringenin. Planta Med. 68:449-51
205. Zubieta C, Dixon RA, Noel JP. 2001. Crystal structures of chalcone O-methyltransferase and isoflavone O-methyltransferase reveal the structural basis for substrate specificity in plant O-methyltransferases. Nat. Struct. Biol. 8:271-79