Abstract
In the literature, it has been shown that the naturally occurring trans-zearalenone (ZEN) is transformed by ultraviolet irradiation to cis-ZEN. However, the practical relevance of this transformation in animal feeding remains unclear. The aim of the present preliminary investigation was to examine the effect of UV-irradiation on the concentration of trans-ZEN in a natural feed matrix at different dry matter contents to simulate the dry and wet feeding techniques usually applied in pig feeding. Four variants, air dry or wet ZEN-contaminated ground maize either irradiated or not were tested and analysed with conventional HPLC-FLD for trans-ZEN changes, which were further examined for cis-ZEN formation by HPLC-MS/MS. In conclusion, it could be shown that, under the investigated wet feed conditions, naturally occurring trans-ZEN was partially converted by ultraviolet irradiation to its cis counterpart. In contrast, the cis/trans isomerization seemed not to be relevant in dry maize. The consequence of this finding for practical liquid feeding systems for pigs requires further investigation. Additionally, an improvement of the analytical method for cis-ZEN determination is needed.
Similar content being viewed by others
References
Abbas HK, Shier WT, Mirocha CJ (1984) Sensitivity of cultured human and mouse fibroblasts to trichothecenes. J Assoc Off Anal Chem 67(3):607–610
EFSA (2004) Opinion of the scientific panel on contaminants in the food chain on a request from the commission related to zearalenone (ZON) as undesirable substance in animal feed (Question N EFSA-Q-2003-037). EFSA J 89:1–35
Kiang DT, Kennedy BJ, Pathre SV, Mirocha CJ (1978) Binding characteristics of zearalenone analogs to estrogen receptors. Cancer Res 38(11 Pt 1):3611–3615
Köppen R, Riedel J, Emmerling F, Koch M (2012a) (3S,11Z)-14,16-Dihy-droxy-3-methyl-3,4,5,6,9,10-hexa-hydro-1H-2-benz-oxacyclo-tet ra-decine-1,7(8H)-dione (cis-zearalenone): a redetermination. Acta Crystallogr Sect E Struct Rep Online 68(Pt 3):o832. doi:10.1107/S1600536812002735
Köppen R, Riedel J, Proske M, Drzymala S, Rasenko T, Durmaz V, Weber M, Koch M (2012b) Photochemical trans-/cis-isomerization and quantitation of zearalenone in edible oils. J Agric Food Chem 60(47):11733–11740
Miles CO, Erasmuson AF, Wilkins AL, Towers NR, Smith BL, Garthwaite I, Scahill BG, Hansen RP (1996) Ovine metabolism of zearalenone to alpha-zearalanol (zeranol). J Agric Food Chem 44(10):3244–3250
Mirocha CJ, Pathre SV, Behrens J, Schauerhamer B (1978) Uterotropic activity of cis and trans isomers of zearalenone and zearalenol. Appl Environ Microbiol 35(5):986–987
Munoz L, Castro JL, Cardelle M, Castedo L, Riguera R (1989) Acetylated mycotoxins from Fusarium-Graminearum. Phytochemistry 28(1):83–85. doi:10.1016/0031-9422(89)85014-9
Naumann C, Bassler R (2006) Die chemische Untersuchung von Futtermitteln. 3. Auflage., 6. Erg., 16.9.2. VDLUFA, Darmstadt
Naumann C, Bassler R (2012) Die chemische Untersuchung von Futtermitteln. 3. Auflage., 8. Erg., 3.1. VDLUFA, Darmstadt
Peters CA (1972) Photochemistry of zearalenone and its derivatives. J Med Chem 15(8):867–& doi:10.1021/Jm00278a028
Rempe I, Kersten S, Brezina U, Hermeyer K, Beineke A, Dänicke S (2013) Time-dependent effects of graded levels of Fusarium toxin-contaminated maize in diets for female piglets. World Mycotoxin J 6(1):51–63. doi:10.3920/Wmj2012.1494
Richardson KE, Hagler WM, Mirocha CJ (1985) Production of zearalenone, alpha-zearalenol and beta-zearalenol, and alpha-zearalenol and beta-zearalanol by Fusarium Spp in rice culture. J Agric Food Chem 33(5):862–866. doi:10.1021/Jf00065a024
Shier WT, Shier AC, Xie W, Mirocha CJ (2001) Structure-activity relationships for human estrogenic activity in zearalenone mycotoxins. Toxicon 39(9):1435–1438. doi:10.1016/S0041-0101(00)00259-2
Smyth MR, Frischkorn CGB (1980) Simultaneous determination of the trans and cis forms of zearalenone in cereal products by high-performance liquid-chromatography with voltammetric detection. Anal Chim Acta 115:293–300. doi:10.1016/S0003-2670(01)93168-X
Conflict of interest
None
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Brezina, U., Kersten, S., Valenta, H. et al. UV-induced cis-trans isomerization of zearalenone in contaminated maize. Mycotoxin Res 29, 221–227 (2013). https://doi.org/10.1007/s12550-013-0178-7
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s12550-013-0178-7