Lifelong and prenatal effects of phytoestrogens

Current Bioactive Compounds

Volumn 7, Issue 3, 2011, Pages 172-179

  Zierau, Oliver ^a   Power, Krista A ^b  

^a DRESDEN UNIVERSITY OF TECHNOLOGY   (Germany)

^b AGRICULTURE AND AGRI FOOD CANADA   (Canada)

Author keywords

Estrogen receptor; Isoflavone; Lifelong and prenatal; Lignan; Phytoestrogen

Indexed keywords

DAIDZEIN; GENISTEIN; ISOFLAVONE DERIVATIVE; LIGNAN DERIVATIVE; MATAIRESINOL; PHYTOESTROGEN; SECOISOLARICIRESINOL;

AGING; ARTICLE; BREAST CANCER; CANCER PREVENTION; DIETARY INTAKE; DRUG ACTIVITY; EMBRYO DEVELOPMENT; ESTROGEN ACTIVITY; FETUS DEVELOPMENT; GERM LINE; HEALTH HAZARD; HORMONAL CARCINOGENESIS; HORMONAL REGULATION; HUMAN; MENOPAUSAL SYNDROME; NONHUMAN; POSTNATAL DEVELOPMENT; PRIORITY JOURNAL; PUBERTY; SOUTHEAST ASIA; SOYBEAN;

EID: 80051711925     PISSN: 15734072     EISSN: 18756646     Source Type: Journal    
DOI: 10.2174/157340711796817931     Document Type: Article

References (88)

1. Dixon, R.A. Phytoestrogens. Annu. Rev. Plant Biol., 2004, 55, 225-261.
2. Ren, M.Q.; Kuhn, G.; Wegner, J.; Chen, J. Isoflavones, substances with multi-biological and clinical properties. Eur. J. Nutr., 2001, 40(4), 135-146.
3. Moeller, F.J.; Zierau, O.; Hertrampf, T.; Bliedtner, A.; Diel, P.; Vollmer, G. Long-term effects of dietary isoflavones on uterine gene expression profiles. J. Steroid Biochem. Mo.l Biol., 2009, 113(3-5), 296-303.
4. Bennetts, H.W.; Underwood, E.J.; Shier, F.L. A specific breeding problem of sheep on subterranean clover pastures in Western Australia. Br. Vet. J., 1946, 102(11), 348-352.
5. Fletcher, R.J. Food sources of phyto-oestrogens and their precursors in Europe. Br. J. Nutr., 2003, 89 (Suppl 1), S39-43.
6. Franke, A.A.; Hankin, J.H.; Yu, M.C.; Maskarinec, G; Low, S; Custer, L.J. Isoflavone levels in soy foods consumed by multiethnic populations in Singapore and Hawaii. J. Agric. Food Chem., 1999, 47(3), 977-986.
7. Reinli, K.; Block, G. Phytoestrogen content of foods-a compendium of literature values. Nutr. Cancer, 1996, 26(2), 123-148.
8. Xu, W.H.; Zheng, W.; Xiang, Y.B.; Ruan, Z.X.; Cheng, J.R.; Dai, Q.; Gao, Y.T.; Shu, X.O. Soya food intake and risk of endometrial cancer among Chinese women in Shanghai: population based casecontrol study. BMJ, 2004, 328(7451), 1285.
9. NTP, NTP Multigenerational Reproductive Study of Genistein (CAS No. 446-72-0) in Sprague-Dawley Rats (Feed Study). Natl. Toxicol. Prog. Tech. Rep. Ser., 2008(539), 1-266.
10. King, A.; Young, G. Characteristics and occurrence of phenolic phytochemicals. J. Am. Diet Assoc., 1999, 99(2), 213-218.
11. Rice, S.; Whitehead, S.A. Phytoestrogens oestrogen synthesis and breast cancer. J. Steroid Biochem. Mol. Biol., 2008, 108(3-5), 186-195.
12. Setchell, K.D.; Cassidy, A. Dietary isoflavones: biological effects and relevance to human health. J. Nutr., 1999, 129(3), 758S-767S.
13. Akaza, H.; Miyanaga, N.; Takashima, N.; Naito, S.; Hirao, Y.; Tsukamoto, T.; Mori, M. Is daidzein non-metabolizer a high risk for prostate cancer? A case-controlled study of serum soybean isoflavone concentration. Jpn. J. Clin. Oncol., 2002, 32(8), 296-300.
14. 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., 1995, 208(1), 40-43.
15. Blair, Robert M.; Appt, Susan E.; Bennetau-Pelissero, Catherine; Clarkson, Thomas B.; Anthony, Mary S.; Lamothe, Valerie; Potter, Susan M. Dietary soy and soy isoflavones have gender-specific effects on plasma lipids and isoflavones in golden Syrian f(1)b hybrid hamsters. J. Nutr., 2002, 132(12), 3585-3591.
16. Brown, N.M; Setchell K.D. Animal models impacted by phytoestrogens in commercial chow: implications for pathways influenced by hormones. Lab. Invest., 2001, 81(5), 735-747.
17. Lundh, T. Metabolism of estrogenic isoflavones in domestic animals. Proc. Soc. Exp. Biol. Med., 1995, 208(1), 33-39.
18. Barkhem, T.; Carlsson, B.; Nilsson, Y.; Enmark, E.; Gustafsson, J.A.; Nilsson, S. Differential response of estrogen receptor alpha and estrogen receptor beta to partial estrogen agonists/antagonists. Mol. Pharmacol., 1998, 54(1), 105-112.
19. Cos, P.; De Bruyne, T.; Apers, S.; Vanden Berghe, D.; Pieters, L.; Vlietinck, A.J. Phytoestrogens: recent developments. Planta Med., 2003, 69(7), 589-599.
20. Kuiper, G.G.; Lemmen, J.G.; Carlsson, B.; Corton, J.C.; Safe, S.H.; Van Der Saag, P.T.; Van Der Burg, B.; Gustafsson, J.A. Interaction of estrogenic chemicals and phytoestrogens with estrogen receptor beta. Endocrinology, 1998, 139(10), 4252-4263.
21. Akiyama, T.; Ishida, J.; Nakagawa, S.; Ogawara, H.; Watanabe, S.; Itoh, N.; Shibuya, M.; Fukami, Y. Genistein, a specific inhibitor of tyrosine-specific protein kinases. J. Biol. Chem., 1987, 262(12), 5592-5595.
22. Mezei, O.; Banz, W.J.; Steger, R.W.; Peluso, M.R.; Winters, T.A.; Shay, N. Soy isoflavones exert antidiabetic and hypolipidemic effects through the PPAR pathways in obese Zucker rats and murine RAW 264.7 cells. J. Nutr., 2003, 133(5), 1238-1243.
23. Nguyen, T.T.; Tran, E.; Nguyen, T.H.; Do, P.T.; Huynh, T.H.; Huynh, H., The role of activated MEK-ERK pathway in quercetininduced growth inhibition and apoptosis in A549 lung cancer cells. Carcinogenesis, 2004, 25(5), 647-659.
24. Olson, S.H.; Bandera, E.V.; Orlow, I. Variants in estrogen biosynthesis genes, sex steroid hormone levels, and endometrial cancer: a HuGE review. Am. J. Epidemiol., 2007, 165(3), 235-245.
25. Setchell, K.D. Phytoestrogens: the biochemistry, physiology, and implications for human health of soy isoflavones. Am. J. Clin. Nutr., 1998, 68(6 Suppl), 1333S-1346S.
26. Wilson, T.; March, H.; Banz, W.J.; Hou, Y.; Adler, S.; Meyers, C.Y.; Winters, T.A.; Maher, M.A. Antioxidant effects of phyto-and synthetic-estrogens on cupric ion-induced oxidation of human lowdensity lipoproteins in vitro. Life Sci., 2002, 70(9), 2287-2297.
27. Moeller, F.J.; Diel, P.; Zierau, O.; Hertrampf, T.; Maass, J.; Vollmer, G. Long-term dietary isoflavone exposure enhances estrogen sensitivity of rat uterine responsiveness mediated through estrogen receptor alpha. Toxicol. Lett., 2010, 196(3), 142-513.
28. Parkin, D.M.; Bray F.; Ferlay J.; Pisani P. Global cancer statistics, 2002. CA Cancer J. Clin., 2005, 55(2), 74-108.
29. Bouker, K.B.; Hilakivi-Clarke, L. Genistein: does it prevent or promote breast cancer? Environ. Health Perspect., 2000, 108(8), 701-708.
30. Travis, R.C.; Allen, N.E.; Appleby, P.N.; Spencer, E.A.; Roddam, A.W.; Key, T.J. A prospective study of vegetarianism and isoflavone intake in relation to breast cancer risk in British women. Int. J. Cancer, 2008, 122(3), 705-710.
31. Korde, L.A.; Wu, A.H.; Fears, T.; Nomura, A.M.Y.; West, D.W.; Kolonel, L.N.; Pike, M.C.; Hoover, R.N.; Ziegler, R.G. Childhood soy intake and breast cancer risk in Asian American women. Cancer Epidemiol. Biomarkers Prev., 2009, 18(4), 1050-1059.
32. Wu, A.H.; Wan, P.; Hankin, J.; Tseng, C.C.; Yu, M.C.; Pike, M.C. Adolescent and adult soy intake and risk of breast cancer in Asian-Americans. Carcinogenesis, 2002, 23(9),1491-1496.
33. Messina, M.; Hilakivi-Clarke, L. Early intake appears to be the key to the proposed protective effects of soy intake against breast cancer. Nutr. Cancer, 2009, 61(6), 792-798.
34. Lamartiniere, C.A.; Cotroneo M.S.; Fritz W.A.; Wang J.; Mentor-Marcel R.; Elgavish A. Genistein chemoprevention: timing and mechanisms of action in murine mammary and prostate. J. Nutr., 2002, 132(3), 552S-558S.
35. Hakkak, R.; Korourian, S.; Shelnutt, S.R.; Lensing, S.; Ronis, M.J.J.; Badger, T.M. Diets containing whey proteins or soy protein isolate protect against 7,12-dimethylbenz(a)anthracene-induced mammary tumors in female rats. Cancer Epidemiol. Biomarkers Prev., 2000, 9(1), 113-117.
36. Luijten, M.; Verhoef, A.; Dormans, J.A.M.A.; Beems, R.B.; Cremers, H.W.J.M.; Nagelkerke, N.J.D.; Adlercreutz, H.; Penalvo, J.L.; Piersma, A.H. Modulation of mammary tumor development in Tg.NK (MMTV/c-neu) mice by dietary fatty acids and life stage specific exposure to phytoestrogens. Reprod. Toxicol., 2007, 23(3), 407-413.
37. Unfer, V.; Casini, M.L.; Costabile, L.; Mignosa, M.; Gerli, S.; Di Renzo, G.C. Endometrial effects of long-term treatment with phytoestrogens: a randomized, double-blind, placebo-controlled study. Fertil. Steril., 2004, 82(1), 145-148.
38. Newbold, R.R.; Banks, E.P.; Bullock, B.; Jefferson, W.N. Uterine adenocarcinoma in mice treated neonatally with genistein. Cancer Res., 2001, 61(11), 4325-4328.
39. Thigpen, J.E.; Locklear, J.; Haseman, J.K.; Saunders, H.; Grant, M.F.; Forsythe, D.B. Effects of the dietary phytoestrogens daidzein and genistein on the incidence of vulvar carcinomas in 129/J mice. Cancer Detect. Prev., 2001, 25(6), 527-532.
40. McVey, M.J.; Cooke, G.M.; Curran, I.H. Altered testicular microsomal steroidogenic enzyme activities in rats with lifetime exposure to soy isoflavones. J. Steroid Biochem. Mol. Biol., 2004, 92(5), 435-446.
41. Roberts, D.; Veeramachaneni, D.N.R.; Schlaff, W.D.; Awoniyi, C.A. Effects of chronic dietary exposure to genistein, a phytoestrogen, during various stages of development on reproductive hormones and spermatogenesis in rats. Endocrine, 2000, 13(3), 281-286.
42. Jarred, R.A.; McPherson, S.J.; Jones, M.E.E.; Simpson, E.R.; Risbridger, G.P. Anti-androgenic action by red clover-derived dietary isoflavones reduces non-malignant prostate enlargement in aromatase knockout (ArKo) mice. Prostate, 2003, 56(1), 54-64.
43. Mori, M.; Sagara, M.; Ikeda, K.; Miki T.; Yamori Y. Soy isoflavones improve bone metabolism in postmenopausal Japanese women. Clin. Exp. Pharmacol. Physiol., 2004, 31 (Suppl 2), S44-46.
44. Mardon, J.; Mathey, J.; Kati-Coulibaly, S.; Puel, C.; Davicco, M.-J.; Lebecque, P.; Horcajada, M.-N.; Coxam, V. Influence of lifelong soy isoflavones consumption on bone mass in the rat. Exp. Biol. Med. (Maywood), 2008, 233(2), 229-237.
45. Lephart, E.D.; Galindo, E.; Bu, L.H. Stress (hypothalamicpituitary-adrenal axis) and pain response in male rats exposed lifelong to high vs. low phytoestrogen diets. Neurosci. Lett., 2003, 342(1-2), 65-68.
46. Lephart, E.D.; Rhees, R.W.; Setchell, K.D.R.; Bu, L.H.; Lund, T.D. Estrogens and phytoestrogens: brain plasticity of sexually dimorphic brain volumes. J. Steroid Biochem. Mol. Biol., 2003, 85(2-5), 299-309.
47. Lund, T.D.; West, T.W.; Tian, L.Y.; Bu, L.H.; Simmons, D.L.; Setchell, K.D.R.; Adlercreutz, H.; Lephart, E.D. Visual spatial memory is enhanced in female rats (but inhibited in males) by dietary soy phytoestrogens. BMC Neurosci., 2001, 2, 20.
48. Flynn, K.M.; Ferguson, S.A.; Delclos, K.B.; Newbold, R.R. Multigenerational exposure to dietary genistein has no severe effects on nursing behavior in rats. Neurotoxicology, 2000, 21(6), 997-1001.
49. Kuhnle, G.C.; Dell'Aquila, C.; Aspinall, S.M.; Runswick, S.A.; Mulligan, A.A.; Bingham, S.A. Phytoestrogen content of beverages, nuts, seeds, and oils. J. Agric. Food Chem., 2008, 56(16), 7311-7315.
50. Thompson, L.U.; Boucher, B.A.; Liu, Z.; Cotterchio, M.; Kreiger, N. Phytoestrogen content of foods consumed in Canada, including isoflavones, lignans, and coumestan. Nutr. Cancer, 2006, 54(2), 184-201.
51. Lehraiki, A.; Attoumbre, J.; Bienaime, C.; Matifat, F.; Bensaddek, L.; Nava-Saucedo, E.; Fliniaux, M.A.; Ouadid-Ahidouch, H.; Baltora-Rosset, S. Extraction of lignans from flaxseed and evaluation of their biological effects on breast cancer MCF-7 and MDA-MB-231 cell lines. J. Med. Food, 2010, 13(4), 834-841.
52. Muir, A.D., Flax lignans--analytical methods and how they influence our lunderstanding of biological activity. J. AOAC Int., 2006, 89(4), 1147-1157.
53. Lampe, J.W. Isoflavonoid and lignan phytoestrogens as dietary biomarkers. J. Nutr., 2003, 133 (Suppl 3), 956S-964S.
54. Kuhnle, G.G.C.; Dell'Aquila, C.; Aspinall, S.M.; Runswick, S.A.; Mulligan, A.A.; Bingham, S.A. Phytoestrogen content of foods of animal origin: dairy products, eggs, meat, fish, and seafood. J. Agric. Food Chem., 2008, 56(2), 10099-10104.
55. Basu, S.; Thomas, J.; Acharya, S. Prospects for growth in global nutraceutical and functional food markets: a canadian perspective. Austr. J. Basic Appl. Sci., 2007(1), 637-649.
56. Gagnon, N.; Cortes, C.; Petit, H.V.Weekly excretion of the mammalian lignan enterolactone in milk of dairy cows fed flaxseed meal. J. Dairy Res., 2009, 76(4), 455-458.
57. Adlercreutz, H.; Heikkinen, R.; Woods, M.; Fotsis, T.; Dwyer, J.T.; Goldin, B.R.; Gorbach, S.L. Excretion of the lignans enterolactone and enterodiol and of equol in omnivorous and vegetarian postmenopausal women and in women with breast cancer. Lancet, 1982, 2(8311), 1295-1299.
58. Boccardo, F.; Lunardi, G.; Guglielmini, P.; Parodi, M.; Murialdo, R.; Schettini, G.; Rubagotti, A. Serum enterolactone levels and the risk of breast cancer in women with palpable cysts. Eur. J. Cancer, 2004, 40(1), 84-89.
59. Dai, Q.; Franke, A.A.; Jin, F.; Shu, X.O.; Hebert, J.R.; Custer, L.J.; Cheng, J.; Gao, Y.T.; Zheng, W. Urinary excretion of phytoestrogens and risk of breast cancer among Chinese women in Shanghai. Cancer Epidemiol. Biomarkers Prev., 2002, 11(9), 815-821.
60. Ingram, D.; Sanders, K.; Kolybaba, M.; Lopez, D. Case-control study of phyto-oestrogens and breast cancer. Lancet, 1997, 350(9083), 990-994.
61. Linseisen, J.; Piller, R.; Hermann, S.; Chang-Claude, J. Dietary phytoestrogen intake and premenopausal breast cancer risk in a German case-control study. Int. J. Cancer, 2004, 110(2), 284-290.
62. McCann, S.E.; Muti, P.; Vito, D.; Edge, S.B.; Trevisan, M.; Freudenheim, J.L. Dietary lignan intakes and risk of pre-and postmenopausal breast cancer. Int. J. Cancer, 2004, 11(3), 440-443.
63. Pietinen, P.; Stumpf, K.; Mannisto, S.; Kataja, V.; Uusitupa, M.; Adlercreutz, H. Serum enterolactone and risk of breast cancer: a case-control study in eastern Finland. Cancer Epidemiol. Biomarkers Prev., 2001, 10(4), 339-344.
64. Touillaud, M.S.; Thiebaut, A.C.M.; Fournier, A.; Niravong, M.; Boutron-Ruault, M.-C.; Clavel-Chapelon, F. Dietary lignan intake and postmenopausal breast cancer risk by estrogen and progesterone receptor status. J. Natl. Cancer Inst., 2007, 99(6), 475-486.
65. den Tonkelaar, I.; Keinan-Boker, L.; Van't Veer, P.; Arts, C.J.M.; Adlercreutz, H.; Thijssen, J.H.H.; Peeters, P.H.M. Urinary phytoestrogens and postmenopausal breast cancer risk. Cancer Epidemiol. Biomarkers Prev., 2001, 10(3), 223-228.
66. Horn-Ross, P.L.; Hoggatt K.J.; West D.W.; Krone M.R.; Stewart S.L.; Anton H.; Bernstei C.L.; Deapen D.; Peel D.; Pinder R.; Reynolds P.; Ross R.K; Wright W.; Ziogas. Recent diet and breast cancer risk: the California Teachers Study (USA). Cancer Causes Control, 2002, 13(5), 407-415.
67. Horn-Ross, P.L.; John E.M.; Lee M.; Stewart S.L.; Koo J.; Sakoda L.C.; Shiau A.C.; Goldstein J.; Davis P.; Perez-Stable E.J. Phytoestrogen consumption and breast cancer risk in a multiethnic population: the Bay Area Breast Cancer Study. Am. J. Epidemiol., 2001, 154(5), 434-441.
68. Keinan-Boker, L.; van Der Schouw, Y.T.; Grobbee, D.E.; Peeters, P.H.M. Dietary phytoestrogens and breast cancer risk. Am. J. Clin. Nutr., 2004, 79(2), 282-288.
69. Kilkkinen, A.; Virtamo, J.; Vartiainen, E.; Sankila, R.; Virtanen, M.J.; Adlercreutz, H.; Pietinen, P. Serum enterolactone concentration is not associated with breast cancer risk in a nested casecontrol study. Int. J. Cancer, 2004, 108(2), 277-280.
70. Zeleniuch-Jacquotte, A.; Adlercreutz, H.; Shore, R.E.; Koenig, K.L.; Kato, I.; Arslan, A.A.; Toniolo, P. Circulating enterolactone and risk of breast cancer: a prospective study in New York. Br. J. Cancer, 2004, 91(1), 99-105.
71. Hulten, K.; Winkvist, A.; Lenner, P.; Johansson, R.; Adlercreutz, H.; Hallmans, G. An incident case-referent study on plasma enterolactone and breast cancer risk. Eur. J. Nutr., 2002, 41(4), 168-176.
72. Buck, K.; Zaineddin, A.K.; Vrieling, A.; Linseisen, J.; Chang-Claude, J. Meta-analyses of lignans and enterolignans in relation to breast cancer risk. Am. J. Clin. Nutr., 2010, 92(1), 141-153.
73. Velentzis, L.S.; Cantwell, M.M.; Cardwell, C.; Keshtgar, M.R.; Leathem, A.J.; Woodside, J.V. Lignans and breast cancer risk in pre-and post-menopausal women: meta-analyses of observational studies. Br. J. Cancer, 2009, 100(9), 1492-1498.
74. Thanos, J.; Cotterchio, M.; Boucher, B.A.; Kreiger, N.; Thompson, L.U. Adolescent dietary phytoestrogen intake and breast cancer risk (Canada). Cancer Causes Control, 2006, 17(10), 1253-1261.
75. Shu, X.O.; Jin F.; Dai Q.; Wen W.; Potter J.D.; Kushi L.H.; Ruan Z.; Gao Y.T.; Zheng W. Soyfood intake during adolescence and subsequent risk of breast cancer among Chinese women. Cancer Epidemiol. Biomarkers Prev., 2001, 10(5), 483-488.
76. Hilakivi-Clarke, L.; Onojafe, I.; Raygada, M.; Cho, E.; Skaar, T.; Russo, I.; Clarke, R. Prepubertal exposure to zearalenone or genistein reduces mammary tumorigenesis. Br. J. Cancer, 1999, 80(11), 1682-1688.
77. Howlin, J.; McBryan, J.; Martin, F. Pubertal mammary gland development: insights from mouse models. J. Mammary Gland Biol. Neoplasia, 2006, 11(3-4), 283-297.
78. Russo, I.H.; Russo, J. Role of hormones in mammary cancer initiation and progression. J. Mammary Gland Biol. Neoplasia, 1998, 3(1), 49-61.
79. Mueller, S.O.; Simon, S.; Chae, K.; Metzler, M.; Korach, K.S. Phytoestrogens and their human metabolites show distinct agonistic and antagonistic properties on estrogen receptor alpha (ERalpha) and ERbeta in human cells. Toxicol. Sci., 2004, 80(1), 14-25.
80. Penttinen, P.; Jaehrling, J.; Damdimopoulos, A.E.; Inzunza, J.; Lemmen, J.G.; van der Saag, P.; Pettersson, K.; Gauglitz, G.; Maekelae, S.; Pongratz, I. Diet-derived polyphenol metabolite enterolactone is a tissue-specific estrogen receptor activator. Endocrinology, 2007, 148(10), 4875-4886.
81. Penttinen-Damdimopoulou, P.E.; Power, K.A.; Hurmerinta, T.T.; Nurmi, T.; van der Saag, P.T.; Maekelae, S.I. Dietary sources of lignans and isoflavones modulate responses to estradiol in estrogen reporter mice. Mol. Nutr. Food Res., 2009, 53(8), 996-1006.
82. Chen, J.; Tan, K.P.; Ward, W.E.; Thompson, L.U. Exposure to flaxseed or its purified lignan during suckling inhibits chemically induced rat mammary tumorigenesis. Exp. Biol. Med. (Maywood), 2003, 228(8), 951-958.
83. Khan, G.; Penttinen, P.; Cabanes, A.; Foxworth, A.; Chezek, A.; Mastropole, K.; Yu, B.; Smeds, A.; Halttunen, T.; Good, C.; Maekelae, S.; Hilakivi-Clarke, L. Maternal flaxseed diet during pregnancy or lactation increases female rat offspring's susceptibility to carcinogen-induced mammary tumorigenesis. Reprod. Toxicol., 2007, 23(3), 397-406.
84. Yu, B; Khan, G.; Foxworth, A.; Huang, K.; Hilakivi-Clarke, L. Maternal dietary exposure to fiber during pregnancy and mammary tumorigenesis among rat offspring. Int. J. Cancer, 2006, 119(10), 2279-2286.
85. Tan, K.P.; Chen, J.; Ward, W.E.; Thompson, L.U. Mammary gland morphogenesis is enhanced by exposure to flaxseed or its major lignan during suckling in rats. Exp. Biol. Med. (Maywood), 2004, 229(2), 147-157.
86. Eliasson, C.; Kamal-Eldin, A.; Andersson, R.; Aman, P. Highperformance liquid chromatographic analysis of secoisolariciresinol diglucoside and hydroxycinnamic acid glucosides in flaxseed by alkaline extraction. J. Chromatogr. A, 2003, 1012(2), 151-159.
87. Henley, D.V.; Korach, K.S. Physiological effects and mechanisms of action of endocrine disrupting chemicals that alter estrogen signaling. Hormones (Athens), 2010, 9(3), 191-205.
88. Tou, J.C.; Thompson, L.U. Exposure to flaxseed or its lignan component during different developmental stages influences rat mammary gland structures. Carcinogenesis, 1999, 20(9), 1831-1835.