Tracing the Biotransformation of PCBs and PBDEs in Common Carp (Cyprinus carpio) Using Compound-Specific and Enantiomer-Specific Stable Carbon Isotope Analysis.

Compound-specific and enantiomer-specific carbon isotope composition was investigated in terms of biotransformation of polychlorinated biphenyls (PCBs) and polybrominated diphenyl ethers (PBDEs) as well as atropisomers of chiral PCB congeners in fish by exposing common carp (Cyprinus carpio) to certain PCB and PBDE congeners. The calculated carbon isotope enrichment factors (ε) for PCB 8, 18, and 45 were -1.99, -1.84, and -1.70‰, respectively, providing evidence of the metabolism of these congeners in fish. The stable carbon isotopic compositions of PBDE congeners clearly reflect the debromination of PBDEs in carp. Significant isotopic fractionation was also observed during the debromination process of BDE 153 (ε = -0.86‰). Stereoselective elimination of chiral PCB congeners 45, 91, and 95 was observed, indicating a stereoselective biotransformation process. The similar ε values for E1-PCB 45 (-1.63‰) and E2-PCB 45 (-1.74‰) indicated that both atropisomers were metabolized by the same reaction mechanisms and stereoselection did not occur at carbon bond cleavage. However, the ε values of (+)-PCB 91 (-1.5‰) and (-)-PCB 95 (-0.77‰) were significantly different from those of (-)-PCB 91 and (+)-PCB 95, respectively. In the latter, no significant isotopic fractionations were observed, indicating that the stereoselective elimination of PCB 91 and 95 could be caused by a different reaction mechanism in the two atropisomers.