Report

Product-to-Parent Reversion of Trenbolone: Unrecognized Risks for Endocrine Disruption

Science  18 Oct 2013:
Vol. 342, Issue 6156, pp. 347-351
DOI: 10.1126/science.1243192

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Return of the Steroid

Trace levels of organic contaminants enter aquatic ecosystems from a variety of sources, including runoff of from agricultural lands. When these compounds and their metabolites break down, it is generally assumed that they become inert and pose less ecological risk. Qu et al. (p. 347, published online 26 September) tracked the sunlight-mediated transformation of metabolites of trenbolone acetate (TBA)—a common growth-promoting steroid given to beef cattle—across a number of conditions in the laboratory and in the field. When the degradation products were exposed to dark conditions following photodegradation, they surprisingly reverted back to TBA metabolites, including analog steroidal compounds similar to TBA with unknown biological effects.

Abstract

Trenbolone acetate (TBA) is a high-value steroidal growth promoter often administered to beef cattle, whose metabolites are potent endocrine-disrupting compounds. We performed laboratory and field phototransformation experiments to assess the fate of TBA metabolites and their photoproducts. Unexpectedly, we observed that the rapid photohydration of TBA metabolites is reversible under conditions representative of those in surface waters (pH 7, 25°C). This product-to-parent reversion mechanism results in diurnal cycling and substantial regeneration of TBA metabolites at rates that are strongly temperature- and pH-dependent. Photoproducts can also react to produce structural analogs of TBA metabolites. These reactions also occur in structurally similar steroids, including human pharmaceuticals, which suggests that predictive fate models and regulatory risk assessment paradigms must account for transformation products of high-risk environmental contaminants such as endocrine-disrupting steroids.

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