Zearalanone

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Background

Zearalanone (ZAN) is an estrogen receptor agonist and also an androgen receptor antagonist [1]. Zearalenone (ZEN), a β-resorcyclic acid lactone (RAL), is a non-steroidal estrogenic mycotoxin biosynthesized by several Fusarium species. Zearalenone (ZEN) is the well-known mycotoxin present in numerous agricultural products [1][2][3][4]. In the human endometrial Ishikawa cell line, zearalenone (ZEN) exhibited strong oestrogenicity [4].When incubated Fusarium semitectum on sorghum, the ratio of ZAN to ZEN remained constant after 5 days, suggesting that ZAN might not be suitable for use as an internal standard [5]. Zearalanone, a major phase I metabolite of zearalenone (ZEN), is an estrogen receptor agonist and also an androgen receptor antagonist. In MCF-7 cells, Zearalanone strongly induced cell proliferation with EC50 value of 1.21 nM and showed significant estrogenic activity. Zearalanone behaved as full hERα agonist. In PALM cells, Zearalanone acted as a hAR antagonist that strongly inhibited the luciferase activity induced by 0.3 nM of R1881, the synthetic androgen [1].

[1]. Molina-Molina JM, Real M, Jimenez-Diaz I, et al. Assessment of estrogenic and anti-androgenic activities of the mycotoxin zearalenone and its metabolites using in vitro receptor-specific bioassays. Food Chem Toxicol.2014 Dec;74:233-9.
[2]. Baldwin RS, Williams RD, Terry MK. Zeranol: a review of the metabolism, toxicology, and analytical methods for detection of tissue residues. Regul Toxicol Pharmacol. 1983 Mar;3(1):9-25.
[3]. Migdalof BH, Dugger HA, Heider JG, et al. Biotransformation of zeranol: disposition and metabolism in the female rat, rabbit, dog, monkey and man. Xenobiotica. 1983 Apr;13(4):209-21.
[4]. Le Guevel R, Pakdel F. Assessment of oestrogenic potency of chemicals used as growth promoter by in-vitro methods. Hum Reprod. 2001 May;16(5):1030-6.
[5]. Aoyama K, Ishikuro E, Noriduki H, et al. Formation Ratios of Zearalanone, Zearalenols, and Zearalanols versus Zearalenone during Incubation of Fusarium semitectum on Sorghum and Ratios in Naturally Contaminated Sorghum. Shokuhin Eiseigaku Zasshi. 2015;56(6):247-51.