Effects of silymarin flavonolignans and synthetic silybin derivatives on estrogen and aryl hydrocarbon receptor activation

Toxicology

Volumn 215, Issue 1-2, 2005, Pages 80-89

  Plíšková, Martina ^a   Vondráček, Jan ^a,b   Křen, Vladimír ^c   Gažák, Radek ^c   Sedmera, Petr ^c   Walterová, Daniela ^d   Psotová, Jitka ^d   Šimánek, Vilím ^d   Machala, Miroslav ^a  

^a VETERINARY RESEARCH INSTITUTE   (Czech Republic)

^b INSTITUTE OF BIOPHYSICS   (Czech Republic)

^c INSTITUTE OF MICROBIOLOGY   (Czech Republic)

^d PALACKÝ UNIVERSITY   (Czech Republic)

Author keywords

Aryl hydrocarbon receptor; Estrogen receptor; Silybin diastereomers; Silymarin

Indexed keywords

23 O PIVALOYLSILYBIN; 7 O BENZYLSILYBIN; ANTINEOPLASTIC AGENT; AROMATIC HYDROCARBON RECEPTOR; ENDOCRINE DISRUPTOR; ESTRADIOL; ESTROGEN RECEPTOR; FLAVONOLIGNAN; SELECTIVE ESTROGEN RECEPTOR MODULATOR; SILIBININ; SILYMARIN; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; CHEMOPROPHYLAXIS; DRUG EFFECT; DRUG POTENCY; DRUG RECEPTOR BINDING; DRUG SAFETY; DRUG SPECIFICITY; ESTROGEN ACTIVITY; HEPATOMA CELL; IN VITRO STUDY; NONHUMAN; PRIORITY JOURNAL; RAT; REPORTER GENE;

ANIMALS; CELL LINE, TUMOR; CELL SURVIVAL; DOSE-RESPONSE RELATIONSHIP, DRUG; HUMANS; LUCIFERASES; MOLECULAR STRUCTURE; RATS; RECEPTORS, ARYL HYDROCARBON; RECEPTORS, ESTROGEN; SILYMARIN; STEREOISOMERISM;

EID: 26444583841     PISSN: 0300483X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tox.2005.06.020     Document Type: Article

References (60)

1. R. Agarwal Cell signaling and regulators of cell cycle as molecular targets for prostate cancer prevention by dietary agents Biochem. Pharmacol. 60 2000 1051 1059
2. N. Ahmad, H. Gali, S. Javed, and R. Agarwal Skin cancer chemoprotective effects of a flavonoid antioxidant silymarin are mediated via impairment of receptor tyrosine kinase signaling and perturbation in cell cycle progression Biochem. Biphys. Res. Commun. 248 1998 294 301
3. H. Babich, and E. Borenfreund Cytotoxic effects of food-additives and pharmaceuticals on cells in culture as determined with the neutral red assay J. Pharm. Sci. 79 1990 592 594
4. J. Berger, and G. Daxenbichler DNA methylation of nuclear receptor genes - possible role in malignancy J. Steroid Biochem. Mol. Biol. 80 2002 1 11
5. N. Bhatia, J. Zhao, D.M. Wolf, and R. Agarwal Inhibition of human carcinoma cell growth and DNA synthesis by silibinin, an active constituent of milk thistle: comparison with silymarin Cancer Lett. 147 1999 77 84
6. M.L. Chatterjee, S.K. Katiyar, R.R. Mohan, and R.A. Agarwal A flavonoid antioxidant, silymarin, affords exceptionally high protection against tumor promotion in the SENCAR mouse skin tumorigenesis model Cancer Res. 59 1999 622 632
7. H. de Groot, and M. Rauen Tissue injury by reactive oxygen species and the protective effects of flavonoids Fundam. Clin. Pharmacol. 12 1998 249 255
8. C. Dees, J.S. Foster, S. Ahamed, and J. Wimalasena Dietary estrogens stimulate human breast cells to enter the cell cycle Environ. Health Perspect. 105 Suppl. 3 1997 633 636
9. C. Dehmlow, J. Erhard, and H. de Groot Inhibition of Kupfer cell functions as an explanation for the hepatoprotective properties of silibinin Hepatology 23 1996 749 754
10. C. Dehmlow, N. Murawski, and H. de Groot Scavenging of reactive oxygen species and inhibition of arachidonic acid metabolism by silibinin in human cells Life Sci. 58 1996 1591 1600
11. P.H. Driggers, and J.H. Segars Estrogen action and cytoplasmic signaling pathways. Part II. The role of growth factors and phosphorylation in estrogen signaling Trends Endocrinol. Metab. 13 2002 422 427
12. K. Flora, M. Hahn, H. Rosen, and K. Benner Milk thistle (Silybum marianum) for the therapy of liver disease Am. J. Gastroenterol. 93 1998 139 143
13. R. Gažák, A. Svobodová, J. Psotová, P. Sedmera, V. Přikrylová, D. Walterová, and V. Křen Oxidised derivatives of silybin and their antiradical and antioxidant activity Bioorg. Med. Chem. 12 2004 5677 5687
14. M.G. Goodin, K.C. Fertuck, T.R. Zacharewski, and R.J. Rosengren Estrogen receptor-mediated actions of polyphenolic catechins in vivo and in vitro Toxicol. Sci. 69 2002 354 361
15. V.G. Hahn, H.D. Lehmann, M. Kurten, H. Uebel, and G. Vogel Pharmacology and toxicology of silymarin, the antihepatotoxic agent of Silybum marianum (L.) Gaertn Arzneimittelforschung 18 1968 698 704
16. D.-H. Han, M.S. Denison, H. Tachibana, and K. Yamada Relationship between estrogen receptor-binding and estrogenic activities of environmental estrogens and suppression by flavonoids Biosci. Biotechnol. Biochem. 66 2002 1479 1487
17. S.K. Katiyar, N.J. Korman, H. Mukhtar, and R. Agarwal Protective effects of silymarin against photocarcinogenesis in a mouse skin model J. Natl. Cancer Inst. 89 1997 556 566
18. N.-C. Kim, T.N. Graf, C.M. Sparacino, M.C. Wani, and M.E. Wall Complete isolation and characterization of silybins and isosilybins from milk thistle (Silybum marianum) Org. Biomol. Chem. 1 2003 1684 1689
19. V. Křen, P. Sedmera, J. Kubisch, P. Halada, V. Přikrylová, A. Jegorov, L. Cvak, R. Gebhardt, J. Ulrichová, and V. Šimánek Glycosylation of silybin. J. Chem. Soc., Perkin Trans. 1 1997 2467 2474
20. V. Křen, J. Ulrichová, P. Kosina, D. Stevenson, P. Sedmwera, V. Přikrylová, P. Halada, and V. Šimánek Chemoenzymatic preparation of silybin β-glucuronides and their biological evaluation Drug. Metabol. Dispos. 28 2000 1513 1517
21. V. Kummer, J. Mašková, J. Čanderle, Z. Zralý, J. Neča, and M. Machala Estrogenic effects of silymarin in ovariectomized rats Vet. Med. -Czech. 46 2001 17 23
22. J.C. Le Bail, F. Varnat, J.C. Nicolas, and G. Habrioux Estrogenic and antiproliferative activities on MCF-7 human breast cancer cells by flavonoids Cancer Lett. 130 1998 209 216
23. D.Y.-W. Lee, and Y. Liu Molecular structure and stereochemistry of silybin A, silybin B, isosilybin A, and isosilybin B, isolated from Silybum marianum (milk thistle) J. Nat. Prod. 66 2003 1171 1174
24. J. Legler, C.E. van den Brink, A. Brouwer, A.J. Murk, P.T. van der Saag, A.D. Vethaak, and B. van den Burg Development of a stably transfected estrogen receptor-mediated luciferase reporter gene assay in the human T47D breast cancer cell line Toxicol. Sci. 48 1999 55 66
25. P. Letteron, G. Labbe, C. Degott, A. Berson, B. Fromenty, M. Delaforge, D. Larrey, and D. Pessayre Mechanism for the protective effects of silymarin against carbon tetrachloride-induced lipid peroxidation and hepatotoxicity in mice Biochem. Pharmacol. 39 1990 2027 2034
26. C. Levy, L.D. Seeff, and K.D. Lindor Use of herbal supplements for chronic liver disease Clin. Gastroenterol. Hepatol. 2 2004 947 956
27. M. Machala, L. Bláha, H.-J. Lehmler, M. Plíš ková, Z. Májková, P. Kapplová, I. Sovadinová, J. Vondráček, T. Malmberg, and L.W. Robertson Toxicity of hydroxylated and quinoid PCB metabolites: inhibition of gap junctional intercellular communication and activation of aryl hydrocarbon and estrogen receptors in hepatic and mammary cells Chem. Res. Toxicol. 17 2004 340 347
28. M. Machala, J. Vondráček, L. Bláha, M. Ciganek, and J. Neča Aryl hydrocarbon receptor-mediated activity of mutagenic polycyclic aromatic hydrocarbons determined using in vitro reporter gene assay Mutat. Res. 497 2001 49 62
29. M.-P. Miguez, I. Anundi, L.A. Sainz-Pardo, and K.O. Lindros Comparative study of the hepatoprotective effect of silymarin and silybin on isolated rat hepatocytes Toxicol. In Vitro 8 1994 581 583
30. R.J. Miksicek Commonly occurring plant flavonoids have estrogenic activity Mol. Pharmacol. 44 1993 37 43
31. L. Mira, M. Silva, and C.F. Manso Scavenging of reactive oxygen species by silibinin dihemisuccinate Biochem. Pharmacol. 48 1994 753 759
32. P. Morazzoni, and E. Bombardelli Silybum marianum (Carduus marianus) Fitoterapia 66 1995 3 42
33. S.O. Mueller, S. Simon, K. Chae, M. Metzler, and K.S. Korach Phytoestrogens and their human metabolites show distinct agonistic and antagonistic properties on estrogen receptor α (ERα) and ERβ in human cells Toxicol. Sci. 80 2004 14 25
34. P. Muriel, T. Garciapina, V. Perz-Alvarez, and M. Mourelle Silymarin protects against paracetamol-induced lipid peroxidation and liver damage J. Appl. Toxicol. 12 1992 439 442
35. A.J. Murk, P.E.G. Leonards, A.S. Bulder, A.S. Jonas, M.J.C. Rozemeijer, M.S. Denison, J.H. Koeman, and A. Brouwer The CALUX (chemical-activated luciferase expression) assay adopted and validated for measuring TCDD equivalents in blood plasma Environ. Toxicol. Chem. 16 1997 1583 1589
36. D.W. Nebert, T.P. Dalton, A.B. Okey, and F.J. Gonzalez Role of aryl hydrocarbon receptor-mediated induction of the CYP1 enzymes in environmental toxicity and cancer J. Biol. Chem. 279 2004 23847 23850
37. M.G. Quaglia, E. Bossú, E. Donati, G. Mazzanti, and A. Brandt Determination of silymarin in the extract from the dried Silybum marianum fruits by high performance liquid chromatography and capillary electrophoresis J. Pharm. Biomed. Anal. 19 1999 435 442
38. B. Rickling, B. Hans, R. Kramarczyk, G. Krombiegel, and R. Weyhenmeyer Two high performance liquid chromatographic assays for the determination of free and total silibinin diastereoisomers in plasma using column switching with electrochemical detection and reverse phase chromatography with ultraviolet detection J. Chromatogr. B 670 1995 267 277
39. S. Safe, and M. Wormke Inhibitory aryl hydrocarbon receptor-estrogen receptor alpha cross-talk and mechanisms of action Chem. Res. Toxicol. 16 2003 807 816
40. D. Seidlová-Wuttke, T. Becker, V. Christoffel, H. Jarry, and W. Wuttke Silymarin is a selective estrogen receptor β (ERβ) agonist and has estrogenic effects in the metaphysis of the femur but no or antiestrogenic effects in uterus of ovariectomized (ovx) rats J. Steroid Biochem. Mol. Biol. 86 2003 179 188
41. V. Šimánek, V. Křen, J. Ulrichová, J. Vičar, and L. Cvak Silymarin: what is in the name...? An appeal for a change of editorial policy Hepatology 32 2000 442 443
42. R.P. Singh, and R. Agarwal Flavonoid antioxidant silymarin and skin cancer Antioxid. Redox Signal 4 2002 655 663
43. R.P. Singh, A.K. Tyangi, J. Zhao, and R. Agarwal Silymarin inhibits growth and causes regression of established skin tumors in SENCAR mice via modulation of mitogen-activated protein kinases and induction of apoptosis Carcinogenesis 23 2002 499 510
44. J. Sonnenbichler, F. Scalera, I. Sonnenbichler, and R. Weyhenmeyer Stimulatory effect of silibinin and silicristin from the milk thistle Silybum marianum on kidney cells J. Pharm. Exp. Ther. 290 1999 1375 1383
45. J. Sonnenbichler, and I. Zetl Specific binding of a flavonolignane derivative to an estradiol receptor V. Cody E. Middleton J.B. Karbone A. Berck Progress in Clinical and Biological Research vol. 280 1988 Alan R. Liss, Inc. New York 369 374
46. J. Sonnenbichler, J. Mattersberger, and H. Rosen Stimulation of RNA synthesis in rat liver and isolated hepatocytes by silybin, an antihepatotoxic agent from Silybum marianum L Gaertn. Hoppe Seyler's Z. Physiol. Chem. 357 1976 1171 1180
47. A. Ström, J. Hartman, J.S. Foster, S. Kietz, J. Wimalasena, and J.-Å. Gustafsson Estrgen receptor β inhibits 17β-estradiol- stimulated proliferation of the breast cancer cell line T47D Proc. Natl. Acad. Sci. U.S.A. 101 2004 1566 1571
48. P. Thelen, H. Jarry, R.-H. Ringert, and W. Wuttke Silibinin down-regulates prostate epithelium-derived Ets transcription factor in LNCaP prostate cancer cells Planta Med. 70 2004 397 400
49. D. Trompier, H. Baubichon-Cortay, X.B. Chang, M. Maitrejean, D. Barron, J.R. Riordon, and A. Di Pietro Multiple flavonoid-binding sites within multidrug resistance protein MRP1 Cell. Mol. Life Sci. 60 2003 2164 2177
50. A. Valenzuela, R. Guerra, and A. Garrido Silybin dihemisuccinate protects rat erythrocytes against phenylhydrazine-induced lipid peroxidation and hemolysis Planta Med. 1987 402 405
51. V.H. Wagner, P. Diesel, and M. Seitz Chemistry and analysis of silymarin from Silybum marianum Gaertn Arzneimittelforschung 24 1974 466 471
52. S. Wenzel, H. Stolte, and M. Soose Effects of silibinin and antioxidants on high glucose-induced alterations of fibronectin turnover in human mesanglial cell cultures J. Pharm. Exp. Ther. 279 1996 1520 1526
53. R. Weyhenmeyer, H. Mascher, and J. Birkmayer Study on dose-linearity of the pharmacokinetics of silibinin diastereomers using a new stereospecific assay Int. J. Clin. Pharmacol. Ther. Toxicol. 30 1992 134 138
54. S. Zhang, C. Qin, and S.H. Safe Flavonoids as aryl hydrocarbon receptor agonists/antagonists: effects of structure and cell context Environ. Health Perspect. 111 2003 1877 1882
55. J. Zhao, M.L. Chatterjee, Y. Sharma, and R. Agarwal Inhibitory effect of a flavonoid antioxidant silymarin on benzoyl peroxide-induced tumor promotion, oxidative stress and inflammatory responses in SENCAR mouse skin Carcinogenesis 21 2000 811 816
56. J. Zhao, Y. Sharma, and R. Agarwal A flavonoid antioxidant, silymarin, affords significant inhibition against 12-O-tetradecanoylphorbol 13-acetate-caused modulation of antioxidant and inflammatory enzymes, and cyclooxygenase 2 and interleukin-1a expression in SENCAR mouse epidermis: implications in the prevention of stage I tumor Mol. Carcinogen. 26 1999 321 333
57. W. Zhu, J.-S. Zhang, and Y.F. Young Silymarin inhibits function of the androgen receptor by reducing nuclear localization of the receptor in the human prostate cancer cell line LNCaP Carcinogenesis 22 2001 1399 1403
58. X. Zi, and R. Agarwal Modulation of mitogen-activated protein kinase activation and cell cycle regulators by the potent skin cancer preventive agent silymarin Biochem. Biophys. Res. Commun. 263 1999 528 536
59. X. Zi, and R. Agarwal Silibinin decreases prostate-specific antigen with cell growth inhibition via G1 arrest, leading to differentiation of prostate carcinoma cells: implications for prostate cancer intervention Proc. Natl. Acad. Sci. U.S.A. 96 1999 7490 7495
60. X. Zi, J. Zhang, R. Agarwal, and M. Pollak Silibinin up-regulates insulin-like growth factor-binding protein 3 expression and inhibits proliferation of androgen-independent prostate cancer cells Cancer Res. 60 2000 5617 5620