Zearalenone : Properties and experimental toxicity;Zéaralénone : Propriétés et toxicité expérimentale

Revue de Medecine Veterinaire

Volumn 152, Issue 3, 2001, Pages 219-234

  Gaumy, J L ^a   Bailly, J D ^a   Burgat, V ^a   Guerre, P ^a  

^a UNIVERSITÉ DE TOULOUSE   (France)

Author keywords

Estrogenic syndrome; Estrogens; Food; Fusarium graminearum; Giberella zea; Mycotoxins; Zearalenone

Indexed keywords

EID: 0006494719     PISSN: 00351555     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (107)

1. ABBAS H.K., MIROCHA C.J., ROSILES R. et CARVAJAL M. : Decomposition of zearalenone and deoxynivalenol in the process of making tortillas from corn. Cereal Chem., 1988, 35, 15-19.
2. ABDELHAMID A.M., KELADA I.P., ALI M.M. et EL-AYOUTY S.A. : Influence of zearalenone on some metabolic, physiological and pathological aspects of female rabbits at two different ages. Arch. Tierernahr., 1992, 42, 63-70.
3. ANONYME : Aliments des animaux : dosage de la zéaralénone, 6 pages, AFNOR, NF V 18-201, 1986.
4. ANONYME : Zearalatest. Mycotoxin Testing System, En ligne, Page consultée le 17 février 2000, Adresse URL: http://www.vicam.com/ vicamy2k/zearalatest.html
5. APPELGREN L.E., ARORA R.G. et LARSSON P. : Autoradiographic studies of [3H] zearalenone in mice. Toxicology, 1982, 25, 243-253.
6. BAGNERIS R.W., GAUL J.A. et WARE G.M. : Liquid chromatographic determination of zearalenone and zearalenol in animal feeds and grains using fluorescence detection. J. Assoc. Off. Anal. Chem., 1986, 69, 894-898.
7. BAILEY D.E., COX G.E., MORGAREIDGE K. et TAYLOR J. : Acute and subacute toxicity of zearalenone in the rat. Tox. Appl. Pharmacol, 1976, 37, 144.
8. BARNA-VETRO I., GYONGYOSI A. et SOLTI L. : Monoclonal antibody-based enzyme-linked immunosorbent assay of Fusarium T-2 and zearalenone toxins in cereals. Appl. Environ. Microbiol., 1994, 60, 729-731.
9. BARTHOLOMEW R.M. et RYAN D.S. : Lack of mutagenicity of some phytoestrogens in the Salmonella/mammalian microsome assay. Mutat. Res., 1980, 78, 317-321.
10. BECCI P.J., JOHNSON W.D., HESS F.G., GALLO M.A., PARENT R.A. et TAYLOR J.M. : Combined two-generation reproduction-teratogenesis study of zearalenone in the rat. J. Appl. Toxicol., 1982, 2, 201-206.
11. BENNETT G.A., LAGODA A.A., SHOTWELL O.L. et HESSELTINE C.W. : Utilization of zearalenone-contaminated corn for ethanol production. J. Amer. Oil Chem. Soc., 1981, 58, 974-976.
12. BENNETT G.A., SHOTWELL O.L. et HESSELTINE C.W. : Destruction of zearalenone in contamined corn. J. Amer. Oil Chem. Soc., 1980, 57, 245-247.
13. BIEHL M.L., PRELUSKY D.B., KORITZ G.D., HARTIN K.E., BUCK W.B. et TRENHOLM H.L. : Biliary excretion and enteropathic cycling of zearalenone in immature pigs. Toxicol. Appl. Pharmacol., 1993, 121, 152-159.
14. BORIES G.F., PERDU-DURAND E.F., SUTRA J.F. et TULLIEZ J.E. : Evidence for glucuronidation and sulfation of zeranol and metabolites (taleranol and zearalanone) by rat and pig hepatic subfractions. Drug Metab. Dispos., 1991, 19, 140-143.
15. BOUTIBONNES P. : Antibacterial activity of zearalenone. Canad. J. Microbiol., 1979, 25, 421-423.
16. BOUTIBONNES P. et LEMARINIER S. : Cytologic alterations induced in Bacillus thuringiensis (Berliner) by zearalenone. Mycopathologia, 1981, 74, 107-111.
17. BOYD P. et WITTLIFF J. : Mechanism of Fusarium mycotoxin action in mammary gland. J. Toxicol. Environ. Health, 1978, 4, 1-8.
18. BRISTOL F.M. et DJURIKOVIC S. : Hyperestrogenism in female swine as the result of feeding mouldy corn. Can. Vet. J., 1971, 12, 132-135.
19. CAHAGNIER B. : Moisissures des aliments peu hydratés, 225 pages, Lavoisier Technique & Documentation, Paris, 1998.
20. CASTEGNARO M. : Les mycotoxines: des contaminants omniprésents dans l'alimentation humaine et animale, risque et prévention. In : M. MOLL and N. MOLL (éds.) : Sécurité alimentaire du consommateur. Lavoisier Tec & Doc., Paris, 1995, 55-83.
21. CHANG H.L. et DEVRIES J.W. : Short liquid Chromatographic method for determination of zearalenone and alpha-zearalenol. J. Assoc. Off. Anal. Chem., 1984, 67, 741-744.
22. CHANG W.M. et LIN J.K. : Transformation of zearalenone and zearalenol by rat erythrocytes. Food Chem. Toxicol., 1984, 22, 887-891.
23. CLARK J.H., PASZKO Z. et PECK E.J. : Nuclear binding and retention of the receptor estrogen complex : Relation to the agonistic and antagonistic properties of estriol. Endocrinology, 1977, 100, 91-96.
24. COORAY R. : Effects of some mycotoxins on mitogen-induced blastogenesis and SCE frequency in human lymphocytes. Food Chem. Toxicol., 1984, 22, 529-534.
25. DACASTO M., ROLANDO P., NACHTMANN C., CEPPA L. et NEBBIA C. : Zearalenone mycotoxicose in piglets suckling sows fed contaminated grain. Vet. Hum. Toxicol., 1995, 37, 359-361.
26. 14C zearalenone in laying hens. J. Agric. Food Chem., 1980, 28, 286-291.
27. EVERETT D.J., PERRY C.J., SCOTT K.A., MARTIN B.W. et TERRY M.K. : Estrogenic potencies of resorcylic acid lactones and 17 beta-estradiol in female rats. J Toxicol Environ Health, 1987, 20, 435-443.
28. FALK H. : Liver. In : D. SCHOTTENFELD et J.F.JR FRAUMENI (éds.) : Cancer Epidemiology and Prevention, Saunders, Toronto, 1982.
29. FITZPATRICK D.W., ARBUCKLE L.D. et HASSEN A.M. : Zearalenone metabolism and excretion in the rat : effect of different doses. J. Environ. Sci. Health, 1988, 23, 343-354.
30. GAREIS M., BAUER J., THIEM J., PLANK G., GRABLEY S. et GEDEK B. : Cleavage of zearalenone-glycoside, a "masked" mycotoxin, during digestion in swine. Zentralbl Veterinarmed, 1990, 37, 236-240.
31. GRAY L.E. JR, FERRELL J.M. et OSTBY J.S. : Alteration of behavorial sex differentiation by exposure to estrogenic compounds during a critical neonatal period : effects of zearalenone, methoxychlor, and estradiol in hamsters. Toxicol. Appl. Pharmacol., 1985, 80, 127-136.
32. GREENMAN D.L., MEHTA R.G. et WITTLIFF J.L. : Nuclear interactions of Fusarium mycotoxins with estradiol binding sites in the mouse uterus. J. Toxicol. Environ. Health, 1979, 5, 593-598.
33. HAGLER W.M., DANKO G., HORVATH L., PALYUSIK M. et MIROCHA C.J. : Transmission of zearalenone and its metabolite into ruminant milk. Acta Vet. Acad. Sci. Hung., 1980, 28, 209-216.
34. HIDY P.H., BALDWIN R.S., GRESHAM R.L., KEITH C.L. et MC MULLEN J.R. : Zearalenone and some derivatives : production and biological activities. Adv. Appl. Microbiol., 1977, 22, 59-82.
35. HOBSON W., BAILEY J. et FULLER G.B. : Hormone effects of zearalenone in nonhuman primates. J. Toxicol. Environ. Health, 1977, 3, 43-57.
36. INGEROWSKI G. et STAN H. : In vitro metabolism of the anabolic drug zeranol. J. Environ. Pathol. Toxicol., 1979, 2, 1173-1182.
37. INGEROWSKI G.H., SCHEUTWINKEL-REICH M. et STAN H.J. : Mutagenicity studies on veterinary anabolic drugs with the Salmonella/microsome test. Mutat. Res., 1981, 91, 93-98.
38. INTERNATIONAL AGENCY FOR RESEARCH ON CANCER (IARC) : Toxins derived from Fusarium graminearum, F. culmorum and F. crookwellense : zéaralénone, déoxynivalénol, nivalénol and fusarenone X. In : IARC Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans, IARC, Lyon, 1993, 397-444.
39. ITO Y. et OHTSUBO K. : Effects of neonatal administration of zearalenone on the reproductive physiology of female mice. J. Vet. Med. Sci., 1994, 56, 1155-1159.
40. KALLELA K. et VASENIUS L. : The effects of rumen fluid on the content of zearalenone in animal fodder. Nord. Vet. Med., 1982, 34, 336-339.
41. KATZENELLENBOGEN B.S., KATZENELLENBOGEN J.A. et MORDECAI D. : Zearalenones : Characterization of the estrogenic potencies and receptor interactions of a series of fungal β-resorcylic acid lactones. Endocrinology, 1979, 105, 33-40.
42. KIANG D.T., KENNEDY B.J., PATHRE S.V. et MIROCHA C.J. : Binding characteristics of zearalenone analogs to estrogen receptors. Cancer Res., 1978, 38, 3611-3615.
43. KIESSLING K.H. : The effect of zearalenone on growth rate, organ weight and muscle fibre composition in growing rats. Acta Pharmacol. Toxicol., 1982, 51, 154-158.
44. KIESSLING K.H. et PETTERSSON H. : Metabolism of zearalenone in rat liver. Acta Pharmacol. Toxicol., 1978, 43, 285-290.
45. KITAGAWA M., TASHIRO F. et UENO Y. : Interaction between zearalenone, an estrogenic mycotoxin, and the estrogen receptor of the rat brain. Proc. Japan. Assoc. Mycotoxicol., 1982, 15, 28-30.
46. KOLLARCZIK B., GAREIS M. et HANELT M. : In vitro transformation of the Fusarium mycotoxins deoxynivalenol and zearalenone by the normal gut mycoflora of pigs. Nat. Toxins, 1994, 2, 105-110.
47. KUCZUC M., BENSON P., HEATH H. et HAYES A. : Evaluation of the mutagenic potential of mycotoxins using Salmonella typhimurium and Saccharomyces cerevisiae. Mutat. Res., 1978, 53, 11-20.
48. KUIPER-GOODMAN T., SCOTT P.M. et WATANABE H. : Risk assessment of the mycotoxin zearalenone. Regulatory Toxicology and Pharmacology, 1987, 7, 253-306.
49. KUMAGAI S. et SHIMIZU T. : Neonatal exposure to zearalenone causes persistent anovulatory estrus in the rat. Arch. Toxicol., 1982, 50, 279-286.
50. KUMAR S.A., O'CONNOR D.L., SEEGER J.L., BEACH T.A. et DICKERMAN H.W. : Purification and characterization of creatine kinase, an estrogen-induced protein (IP) from immature rats. Biochem. Biophys. Res. Commun., 1983, 111, 156-165.
51. KUO C.H., TAUB D., HOFFSOMMER R.D. et WENDLER N.L. : The resolution of ±-zearalenone. Determination of the absolute configuration of the natural enantiomorph. Chem. Commun., 1967, 761-762.
52. LINDSAY D.G. : Zeranol : a "Nature-Identical" Oestrogen ? Fd Chem. Toxic., 1985, 23, 767-774.
53. LIU M.-T., RAM B.P., HART L.P. et PESTKA J.J. : Indirect enzymelinked immunoassay for the mycotoxin zearalenone. Appl. Environ. Microbiol., 1985, 50, 332-336.
54. LONG G.G. et DIEKMAN M.A. : Effect of zearalenone on early pregnancy in guinea pigs. Am. J. Vet. Res., 1989, 50, 1220-1223.
55. MAAROUFI K., CHEKIR L., CREPPY E.E., ELLOUZ F. et BACHA H. : Zearalenone induces modifications of haematological and biochemical parameters in rats. Toxicon, 1996, 34, 535-540.
56. MARTIN P.M., HORWITZ K.B., RYAN D.S. et MCGUIRE W.L. : Phytoestrogen interaction with estrogen receptors in human breast cancer cells. Endocrinology, 1978, 103, 1860-1867.
57. MATSUURA Y., YOSHIZAWA T. et MOROOKA N. : Effect of food additives and heating on the decomposition of zearalenone in wheat flour. J. Food Hyg. Soc. Jpn., 1981, 22, 293-298.
58. MCNUTT S.H., PURWIN P. et MURRAY C. : Vulvovaginitis in swine. J. Am. Vet. Med. Assoc., 1928, 73, 484-492.
59. MEDINA M.B. et SHERMAN J.T. : High performance liquid chromatographic separation of anabolic oestrogens and ultraviolet detection of 17β-oestradiol, zeranol, diethylstilboestrol or zearalenone in avian muscle tissue extracts. Food Addit. Contam., 1986, 3, 263-272.
60. MERCK INDEX. Twelfth Edition, 1996, 1730-1731.
61. MEYER K., USLEBER E., MARTLBAUER E. et BAUER J. : Demonstration of zearalenone metabolites in bile of breeding sows with fertility disturbances. Berl. Munch. Tierarztl. Wochenschr., 1997, 110, 281-283.
62. MILES C.O., ERASMUSON A.F., WILKINS A.L., TOWERS N.R., SMITH B.L., GARTHWAITE I., SCAHILL E.G. et HANSEN R.P. : Ovine metabolism of zearalenone to α-zearalanol (zeranol). J. Agric. Food Chem., 1996, 44, 3244-3250.
63. MIROCHA C.J., CHRISTENSEN C.M. et NELSON G.H. : F-2 (Zearalenone) ; estrogenic mycotoxin from Fusarium. In : S. KADIS, A. CIEGLER A. et S.J. AJL (éds.) : Microbial toxins, Academic Press, New-York, 1971, 107-138.
64. MIROCHA C.J., PATHRE S.V. et ROBISON T.S. : Comparative metabolism of zearalenone and transmission into bovine milk. Food Cosmet. Toxicol., 1981, 19, 25-30.
65. MIROCHA C.J., PATHRE S.V., BEHRENS J. et SCHAUERHAMER B. : Uterotropic activity of cis and trans isomers of zearalenone and zearalenol. Appl. Environ. Microbiol., 1978, 35, 986-987.
66. ème éd. Paris, Masson et Cie., 1974.
67. NIKOV G.N., HOPKINS N.B. BOUE S. et ALWORTH W.L. : Interactions of dietary estrogens with human estrogen receptors and the effect on estrogen receptor-estrogen response element complex formation. Environ. Health Perspect., 2000, 108, 867-872.
68. OKOYE Z.S.C. : Stability of zearalenone in naturally contaminated corn during Nigerian traditional brewing. Food Add. Contamin., 1987, 4, 57-59.
69. OLSEN M. et KIESSLING K.H. : Species differences in zearalenone-reducing activity in subcellular fractions of liver from female domestic animals. Acta Pharmacol. Toxicol., 1983, 52, 287-291.
70. OLSEN M., MALMLOF K., PETTERSSON H., SANDHOLM K. et KIESSLING K.H. : Plasma and urinary levels of zearalenone and alpha-zearalenol in a prepubertal gilt fed zearalenone. Acta Pharmacol. Toxicol., 1985, 56, 239-243.
71. OLSEN M., MIROCHA C.J., ABBAS H.K. et JOHANSSON B. : Metabolism of high concentrations of dietary zearalenone by young male turkey poults. Poult. Sci., 1986, 65, 1905-1910.
72. OLSEN M., PETTERSSON H., SANDHOLM K., VISCONTI A. et KIESSLING K.-H. : Metabolism of zearalenone by sow intestinal mucosa in vitro. Food Chem. Toxic., 1987, 25, 681-683.
73. OLSEN M.E., PETTERSSON H.I., SANDHOLM K.A. et KIESSLING K.H.C. : Quantitative liquid chromatographic method using fluorescence detection for determining zearalenone and its metabolites in blood plasma and urine. J. Assoc. Off. Anal. Chem., 1985, 68, 632-635.
74. PALYUSIK M., HARRACH B., MIROCHA C.J. et PATHRE S.V. : Transmission of zearalenone and zearalenol into porcine milk. Acta Vet. Acad. Sci. Hung., 1980, 28, 217-222.
75. PFOHL-LESZKOWICZ A., CHEKIR-GHEDIRA L., BACHA H. : Genotoxicity of zearalenone, an estrogenic mycotoxin : DNA adduct formation in female mouse tissues. Carcinogenesis, 1995, 16, 2315-20.
76. POMPA G., MONTESISSA C., DI LAURO F.M. et FADINI L. : The metabolism of zearalenone in subcellular fractions from rabbit and hen hepatocytes and its estrogenic activity in rabbits. Toxicology, 1986, 42, 69-75.
77. POWELL-JONES W., RAEFORD S. et LUCIER G.W. : Binding properties of zearalenone mycotoxins to hepatic estrogens receptors. Mol. Pharmacol., 1981, 20, 35-42.
78. PRELUSKY D.B., SCOTT P.M., TRENHOLM H.L. et LAWRENCE G.A. : Minimal transmission of zearalenone to milk of dairy cows. J. Environ. Sci. Health, 1990, 25, 87-103.
79. PULLAR E.M. et LEREW W.M. : Vulvovaginitis of swine. Aust. Vet. J., 1937, 13, 28.
80. REISS N.A. et KAYE A.M. : Identification of the major component of the estrogen-induced protein of rat uterus as the BB isozyme of creatine kinase. J. Biol. Chem., 1981, 256, 5741-5749.
81. RUDDICK J.A., SCOTT P.M. et HARWIN J. : Teratological evaluation of zearalenone administered orally to the rat. Bull. Environ. Contam. Toxicol., 1976, 15, 678-681.
82. RUZSAS C., BIRO-GOSZTONYI M., WOLLER L. et MESS B. : Effect of the fungal toxin (zearalenone) on the reproductive system and fertility of male and female rats. Acta Biol. Acad. Sci. Hung., 1979, 30, 335-345.
83. SAENZ DE RODRIGUEZ C.A. : Environmental hormone contamination in Puerto Rico. N. Engl. J. Med., 1984, 310, 1741-1742.
84. SAENZ DE RODRIGUEZ C.A., BOUGIOVANNI A.M. et CONDE DE BORREGO L. : An epidemic of precocious development in Puerto Rican children. J. Pediatr., 1985, 107, 393-396.
85. SCHWADORF K. et MULLER H.M. : Determination of alpha- and beta-zearalenol and zearalenone in cereals by gas chromatography with ion-trap detection. J. Chromatogr., 1992, 595, 259-267.
86. SEEGER J.I. et KUMAR S.A. : Induction of creatine kinase in immature rat uteri by zearalenone, an estrogenic mycotoxin. Biochem. Int., 1985,10, 597-602.
87. SHEEHAN D.M., BRANHAM W.S., MEDLOCK K.L. et SHANMUGASUNDARAM E.R.B. : Estrogenic activity of zearalenone and zearalanol in the neonatal uterus. Teratology, 1984, 29, 383-392.
88. SHIER W.T. : Estrogenic mycotoxins. Revue Med. Vet., 1998, 149, 599-604.
89. SHREEVE B.J., PATTERSON D.S.P. et ROBERTS B.A. : The "carry-over" of aflatoxin, ochratoxin and zearalenone from naturally contamined feed to tissues, urine and milk of dairy cows. Food Cosmet. Toxicol., 1979, 17, 151-152.
90. STOB M., BALDWIN R.S., TUITE J., ANDREWS F.N. et GILLETTE K.G. : Isolation of an anabolic uterotropic compound from corn infested with Gibberella zeae. Nature, 1962, 196, 1318.
91. TANAKA T., HASEGAWA A., MATSUKI Y., LEE U.-S. et UENO Y. : Rapid and sensitive determination of zearalenone in cereals by high-performance liquid chromatography with fluorescence detection. J. Chromatogr., 1985, 328, 271-278.
92. TASHIRO F., KAWABATA Y. et UENO Y. : Synthesis of a specific protein induced by zearalenone and its derivatives in rat uterus. J. Biochem., 1982, 91, 801-808.
93. TAUB D., GIROTRA N.N., HOFFSOMMER R.D., KUO C.H., SLATES H.L., WEBER S. et WENDLER N.L. : Total synthesis of the macrolide, zearalenone. Tetrahedron, 1968, 24, 2443-2461.
94. TRENHOLM H.L., WARNER R.M. et FARNWORTH E.R. : High performance liquid Chromatographic method using fluorescence detection for quantitative analysis of zearalenone and α-zearalenol in blood plasma. J. Assoc. Off. Anal. Chem., 1981, 64, 302-310.
95. TRENHOLM H.L., WARNER R.M. et FITZPATRICK D.W. : Rapid, sensitive liquid Chromatographic method for determination of zearalenone and α- and β-zearalenol in wheat. J. Assoc. Off. Anal. Chem., 1984, 67, 968-972.
96. TURNER G.V., PHILLIPS T.D., HEIDELBAUGH N.D. et RUSSEL L.H. : High pressure liquid Chromatographic determination of zearalenone in chicken tissues. J. Assoc. Off. Anal. Chem., 1983, 66, 102-104.
97. UENO Y. et KUBOTA K. : DNA-attacking ability of carcinogenic mycotoxins in recombination-deficient mutant cells of Bacillus subtilis. Cancer Res., 1976, 36, 445-451.
98. UENO Y. et YAGASAKI S. : Accelerating effect of zearalenone on RNA and protein syntheses in the uterus of ovariectomized mice. Japan. J. Exp. Med., 1975, 45, 199-205.
99. UENO Y., TASHIRO F. et KOBAYASHIT. : Species differencies in zearalenone-reductase activity. Food Chem. Toxicol., 1983, 21, 167-173.
100. URRY W.H., WEHRMEISTER H.L., HODGE E.B. et HIDY P.H. : The structure of zearalenone. Tetrahedron Let., 1966, 27, 3109-3114.
101. VERDEAL K., BROWN R.R., RICHARDSON T. et RYAN D.S. : Affinity of phytoestrogens for estradiol-binding proteins and effect of coumestrol on growth of 7, 12-dimethylbenz[a]anthracene-induced rat mammary tumours. J. Natl. Cancer Inst., 1980, 64, 285-290.
102. WARNER R., RAM B.P., HART L.P. et PESTKA J.J. : Screening of zearalenone in corn by competitive enzyme-linked immunosorbent assay. J. Agric. Food Chem., 1986, 34, 714-717.
103. WEHNER F., MARASAS W. et THIEL P. : Lack of mutagenicity to Salmonella typhimurium of some Fusarium mycotoxins. Appl. Environ. Microbiol., 1978, 35, 659-662.
104. WEISBURGER J.H. et WILLIAMS G.M. : The distinct health risk analyses required for genotoxic carcinogens and promoting agents. Environ. Health Perspect., 1983, 50, 233-245.
105. WILLIAMS B.A., MILLS K.T., BURROUGHS C.D. et BERN H.A. : Reproductive alterations in female C57BL/Crgl mice exposed neonatally to zearalenone, an estrogenic mycotoxin. Cancer. Lett., 1989, 46, 225-230.
106. WILLIE T.D. et MOREHOUSE L.G. : Mycotoxic fungi, mycotoxins, mycotoxicoses : Mycotoxic fungi and chemistry of mycotoxins, 538 pages, 1977.
107. YAGER J.D. et LIEHR J.G. : Molecular mechanisms of estrogen carcinogenesis. Annu. Rev. Pharmacol. Toxicol., 1996, 36, 203-232.