Rainbow Trout (Oncorhynchus mykiss) Can Eliminate Chiral Organochlorine Compounds Enantioselectively

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Abstract
Dietary accumulation of four chiral organochlorine compoundsα-hexachlorocyclohexane (α-HCH), trans-chlordane, and chlorobiphenyls (CBs) 95 and 136by immature rainbow trout (Oncorhynchus mykiss) was studied to determine if fish can accumulate and eliminate these compounds enantioselectively. Fish rapidly accumulated all four compounds from food spiked at micrograms per gram concentrations during a 40-d feeding period. Depuration half-lives were from 13 d for (±)-α-HCH to 375 d for (±)-CB 136. Fish preferentially eliminated (−)-trans-chlordane and (+)-CB 136, with significant nonracemic residues observed after 20 d. These results are consistent with field measurements of these compounds in fish as well as known metabolic pathways. Enantiomeric fractions (EFs) for these two compounds changed significantly over the course of the experiment, suggesting that trout were enantioselectively biotransforming the compounds during the 238-d depuration phase. CB 95 and α-HCH residues were racemic throughout the experiment. High biomagnification factors for CB 95 suggest that it was not metabolized. Minimum values for metabolic elimination rates calculated from EF suggest that at least 58% of the trans-chlordane depuration rate can be attributed to metabolism, and all of the CB 136 depuration rate can be attributed to it. This study highlights the potential of chiral analysis as a tracer of in vivo biotransformation processes of xenobiotic compounds.

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