| Title | Identification and Environmental Implications of Photo-Transformation Products of Trenbolone Acetate Metabolites. |
| Publication Type | Journal Article |
| Year of Publication | 2013 |
| Journal | Environmental Science & Technology |
| Volume | 47 |
| Issue | 10 |
| Pagination | 5031 - 5041 |
| Authors | Kolodziej, Edward P., Shen Qu, Kristy L. Forsgren, Sarah A. Long, James B. Gloer, Gerrad D. Jones, Daniel Schlenk, Jonas Baltrusaitis, and David M. Cwiertny |
| Publisher | American Chemical Society |
| ISBN Number | 0013-936X |
| Keywords | photodegrdn trenbolone acetate metabolite Oryzias ecotoxicity |
| Abstract | Despite the widespread use of the anabolic androgen trenbolone acetate (TBA) in animal agriculture, evidence demonstrating the occurrence of TBA metabolites such as 17β-trenbolone (17β-TBOH), 17α-trenbolone (17α-TBOH), and trendione (TBO) is relatively scarce, potentially due to rapid transformation processes such as direct photolysis. Therefore, we investigated the phototransformation of TBA metabolites and assocd. ecol. implications by characterizing the photoproducts arising from the direct photolysis of 17β-TBOH, 17α-TBOH, and TBO and their assocd. ecotoxicity. LC-HRMS/MS anal. identified a range of hydroxylated products that were no longer photoactive, with primary photoproducts consisting of monohydroxy species and presumptive diastereomers. Also obsd. were higher-order hydroxylated products probably formed via subsequent reaction of primary photoproducts. NMR anal. confirmed the formation of 12,17-dihydroxy-estra-5(10),9(11),dien-3-one (12-hydroxy-TBOH; 2.2 mg), 10,12,17-trihydroxy-estra-4,9(11),dien-3-one (10,12-dihydroxy-TBOH; 0.7 mg), and a ring-opened 11,12-dialdehyde oxidn. product (TBOH-11,12-dialdehyde; 1.0 mg) after irradn. of ∼14 mg of 17β-trenbolone. Though unconfirmed by NMR, our data suggest that the formation of addnl. isomeric products may occur, likely due to the reactivity of the unique 4,9,11 conjugated triene structure of trenbolone. In vivo exposure studies employing Japanese medaka (Oryzias latipes) indicate that low concns. of 17α-TBOH photoproduct mixts. can alter ovarian follicular development, and photoproducts alter whole-body 17β-estradiol levels. Therefore, direct photolysis yields photoproducts with strong structural similarity to parent steroids, and these photoproducts still retain enough biol. activity to elicit observable changes to endocrine function at trace concns. These data indicate that environmental transformation processes do not necessarily reduce steroid hormone ecotoxicity. [on SciFinder(R)] |