Bioactivation of zearalenone by porcine hepatic biotransformation

Veterinary Research

Volumn 36, Issue 5-6, 2005, Pages 799-810

  Malekinejad, Hassan ^a   Maas Bakker, Roel Franciscus ^a   Fink Gremmels, Johanna ^a  

^a UTRECHT UNIVERSITY   (Netherlands)

Author keywords

Biotransformation; MCF 7 cells; Oestrogenic effects; Pigs; Zearalenone

Indexed keywords

ALPHA ZEARALENOL; ALPHA ZERALANOL; BETA ZEARALENOL; ESTRADIOL; LACTONE DERIVATIVE; UNCLASSIFIED DRUG; ZEARALENONE;

ANIMAL TISSUE; ARTICLE; BIOTRANSFORMATION; CELL STRAIN MCF 7; CONTROLLED STUDY; ESTROGEN ACTIVITY; HUMAN; HUMAN CELL; LIVER; NONHUMAN; RECEPTOR BINDING;

ANIMALS; BIOLOGICAL ASSAY; BIOTRANSFORMATION; CELL LINE, TUMOR; CELL PROLIFERATION; DOSE-RESPONSE RELATIONSHIP, DRUG; ESTRADIOL; ESTROGENS, NON-STEROIDAL; HUMANS; LIVER; MOLECULAR STRUCTURE; SWINE; TIME FACTORS; ZEARALENONE;

ANIMALIA; FUSARIUM; MAMMALIA; MINK CELL FOCUS-FORMING VIRUS; SUIDAE; SUS SCROFA;

EID: 24944445105     PISSN: 09284249     EISSN: None     Source Type: Journal    
DOI: 10.1051/vetres:2005034     Document Type: Article

References (42)

1. Ahamed S., Foster J.S., Bukovsky A., Wimalasena J., Signal transduction through the Ras/Erk pathway is essential for the mycoestrogen zearalenone-induced cell-cycle progression in MCF-7 cells, Mol. Carcinog. 30 (2001) 88-98.
2. Amet Y., Simon B., Quemener E., Mangin P., Floch H.H., Abalain J.H., Partial purification of 3 alpha- and 3 beta-hydroxysteroid dehydrogenases from human hyperplastic prostate. Comparison between the two enzymes, J. Steroid. Biochem. Mol. Biol. 41 (1992) 689-692.
3. Andersen H.R., Andersson A.M., Arnold S.F., Autrup H., Barfoed M., Beresford N.A., et al., Comparison of short-term estrogenicity tests for identification of hormone-disrupting chemicals, Environ. Health Perspect. 107 Suppl. 1 (1999) 89-108.
4. Biehl M.L., Prelusky D.B., Koritz G.D., Hartin K.E., Buck W.B., Trenholm H.L., Biliary excretion and enterohepatic cycling of zearalenone in immature pigs, Toxicol. Appl. Pharmacol. 121 (1993) 152-159.
5. Bories G.F., Perdu-Durand E.F., Sutra J.F., Tulliez J.E., Evidence for glucuronidation and sulfation of zeranol and metabolites (taleranol and zearalanone) by rat and pig hepatic subfractions, Drug. Metab. Dispos. 19 (1991) 140-143.
6. Briske-Anderson M.J., Finley J.W., Newman S.M., The influence of culture time and passage number on the morphological and physiological development of Caco-2 cells, Proc. Soc. Exp. Biol. Med. 214 (1997) 248-257.
7. Chang K., Kurtz H.J., Mirocha C.J., Effects of the mycotoxin zearalenone on swine reproduction, Am. J. Vet. Res. 40 (1979) 1260-1267.
8. Dacasto M., Rolando P., Nachtmann C., Ceppa L., Nebbia C., Zearalenone mycotoxicosis in piglets suckling sows fed contaminated grain, Vet. Hum. Toxicol. 37 (1995) 359-361.
9. Dees C., Foster J.S., Ahamed S., Wimalasena J., Dietary estrogens stimulate human breast cells to enter the cell cycle, Environ. Health Perspect. 105 Suppl. 3 (1997) 633-636.
10. Devleeschouwer N., Legros N., Olea-Serrano N., Paridaens R., Leclercq G., Estrogen conjugates and serum factors mediating the estrogenic trophic effect on MCF-7 cell growth, Cancer Res. 47 (1987) 5883-5887.
11. Diel P., Smolnikar K., Michna H., In vitro test systems for the evaluation of the estrogenic activity of natural products, Planta Med. 65 (1999) 197-203.
12. Esquenet M., Swinnen J.V., Heyns W., Verhoeven G., LNCaP prostatic adenocarcinoma cells derived from low and high passage numbers display divergent responses not only to androgens but also to retinoids, J. Steroid Biochem. Mol. Biol. 62 (1997) 391-399.
13. Gajecki M., Zearalenone-undesirable substances in feed, Pol. J. Vet. Sci. 5 (2002) 117-122.
14. Gao H., Bodine P.V., Murrills R., Bex F.J., Bilezikian J.P., Morris S.A., PTH-dependent adenylyl cyclase activation in SaOS-2 cells: passage dependent effects on G protein interactions, J. Cell. Physiol. 193 (2002) 10-18.
15. Gingras S., Simard J., Induction of 3beta-hydroxysteroid dehydrogenase/isomerase type 1 expression by interleukin-4 in human normal prostate epithelial cells, immortalized keratinocytes, colon, and cervix cancer cell lines, Endocrinology 140 (1999) 4573-4584.
16. Gloy J., Greger R., Schollmeyer P., Huber M., Pavenstadt H., Influence of cell culture conditions and passage number on the response of membrane voltage to ATP and angiotensin II in rat mesangial cells, Ren. Physiol. Biochem. 17 (1994) 62-72.
17. Goya L., Feng P.T., Aliabadi S., Timiras P.S., Effect of growth factors on the in vitro growth and differentiation of early and late passage C6 glioma cells, Int. J. Dev. Neurosci. 14 (1996) 409-417.
18. Huang W., Carlsen B., Rudkin G.H., Shah N., Chung C., Ishida K., Yamaguchi D.T., Miller T.A., Effect of serial passage on gene expression in MC3T3-E1 preosteoblastic cells: a microarray study, Biochem. Biophys. Res. Commun. 281 (2001) 1120-1126.
19. Hudson R.W., Comparison of 3 alpha-hydroxysteroid dehydrogenase activities in the microsomal fractions of hyperplastic, malignant and normal human prostatic tissues, J. Steroid Biochem. 20 (1984) 829-833.
20. Ju Y.H., Carlson K.E., Sun J., Pathak D., Katzenellenbogen B.S., Katzenellenbogen J.A., Helferich W.G., Estrogenic effects of extracts from cabbage, fermented cabbage, and acidified brussels sprouts on growth and gene expression of estrogen-dependent human breast cancer (MCF-7) cells, J. Agric. Food Chem. 48 (2000) 4628-4634.
21. Kawabata Y., Tashiro F., Ueno Y., Synthesis of a specific protein induced by zearalenone and its derivatives in rat uterus, J. Biochem. (Tokyo) 91 (1982) 801-808.
22. Kennedy D.G., Hewitt S.A., McEvoy J.D., Currie J.W., Cannavan A., Blanchflower W.J., Elliot C.T., Zeranol is formed from Fusarium spp. toxins in cattle in vivo, Food Addit. Contam. 15 (1998) 393-400.
23. Kleinova M., Zollner P., Kahlbacher H., Hochsteiner W., Lindner W., Metabolic profiles of the mycotoxin zearalenone and of the growth promoter zeranol in urine, liver, and muscle of heifers, J. Agric. Food Chem. 50 (2002) 4769-4776.
24. 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 139 (1998) 4252-4263.
25. Kuiper-Goodman T., Scott P.M., Watanabe H., Risk assessment of the mycotoxin zearalenone, Regul. Toxicol. Pharmacol. 7 (1987) 253-306.
26. Lowry O.H., Rosebrough N.J., Fair A.L., Randall R.J., Protein measurement with the Folin phenol reagent, J. Biol. Chem. 193 (1951) 265-275.
27. Miles C.O.A.F., Alistair L.W., Wilkins A.L., Neal R.T., Barry L.S., Ian G., Bryan G.S., Richard P.H., Ovine metabolism of Zearalenone to alpha-zearalanol (Zeranol), J. Agric. Food Chem. 44 (1996) 3244-3250.
28. Mirocha C.J., Schauerhamer B., Pathre S.V., Isolation, detection, and quantitation of zearalenone in maize and barley, J. Assoc. Off. Anal. Chem. 57 (1974) 1104-1110.
29. Olsen M., Kiessling K.H., Species differences in zearalenone-reducing activity in subcellular fractions of liver from female domestic animals, Acta Pharmacol. Toxicol. (Copenhagen) 52 (1983) 287-291.
30. Penning T.M., 3 alpha-hydroxysteroid dehydrogenase: three dimensional structure and gene regulation, J. Endocrinol. 150 Suppl. (1996) S175-S187.
31. Penning T.M., Pawlowski J.E., Schlegel B.P., Jez J.M., Lin H.K., Hoog S.S., Bennett M.J., Lewis M., Mammalian 3 alpha-hydroxysteroid dehydrogenases, Steroids 61 (1996) 508-523.
32. Pezzi V., Mathis J.M., Rainey W.E., Carr B.R., Profiling transcript levels for steroidogenic enzymes in fetal tissues, J. Steroid Biochem. Mol. Biol. 87 (2003) 181-189.
33. Pirog E.C., Collins D.C., Metabolism of dihydrotestosterone in human liver: importance of 3alpha- and 3beta-hydroxysteroid dehydrogenase, J. Clin. Endocrinol. Metab. 84 (1999) 3217-3221.
34. Rutten A.A., Falke H.E., Catsburg J.F., Topp R., Blaauboer B.J., van Holsteijn I., Doom L., van Leeuwen F.X., Interlaboratory comparison of total cytochrome P-450 and protein determinations in rat liver microsomes. Reinvestigation of assay conditions, Arch. Toxicol. 61 (1987) 27-33.
35. Shier W.T., Shier A.C., Xie W., Mirocha C.J., Structure-activity relationships for human estrogenic activity in zearalenone mycotoxins, Toxicon 39 (2001) 1435-1438.
36. Soto A.M., Sonnenschein C., Chung K.L., Fernandez M.F., Olea N., Serrano F.O., The E-SCREEN assay as a tool to identify estrogens: an update on estrogenic environmental pollutants, Environ. Health Perspect. 103 Suppl. 7 (1995) 113-122.
37. Soto A.M., Fernandez M.F., Luizzi M.F., Oles Karasko A.S., Sonnenschein C., Developing a marker of exposure to xenoestrogen mixtures in human serum, Environ. Health Perspect. 105 Suppl. 3 (1997) 647-654.
38. Thomas J.L., Mason J.I., Brandt S., Spencer B.R. Jr., Norris W., Structure/function relationships responsible for the kinetic differences between human type 1 and type 2 3beta-hydroxysteroid dehydrogenase and for the catalysis of the type 1 activity, J. Biol. Chem. 277 (2002) 42795-42801.
39. Trenholm H.L., Warner R.M., Fitzpatrick D.W., Rapid, sensitive liquid chromatographic method for determination of zearalenone and alpha- and beta-zearalenol in wheat, J. Assoc. Off. Anal. Chem. 67 (1984) 968-972.
40. Ueno Y., Tashiro F., Alpha-Zearalenol, a major hepatic metabolite in rats of zearalenone, an estrogenic mycotoxin of Fusarium species, J. Biochem. (Tokyo) 89 (1981) 563-571.
41. Weaver G.A., Kurtz H.J., Mirocha C.J., Bates F.Y., Behrens J.C., Robinson T.S., Gipp W.F., Mycotoxin-induced abortions in swine, Can. Vet. J. 19 (1978) 72-74.
42. Yang H.H., Aulerich R.J., Helferich W., Yamini B., Chou K.C., Miller E.R., Bursian S.J., Effects of zearalenone and/or tamoxifen on swine and mink reproduction, J. Appl. Toxicol. 15 (1995) 223-232.