Metabolism of¹⁴C-labeled polychlorinated biphenyl congeners by wheat cell suspension cultures

Abstract

The metabolism of [UL-(14)C]-2,2',5,5'-tetrachlorobiphenyl ((14)C-PCB-52), [UL-(14)C]-2,2',4,4',5,5'-hexachlorobiphenyl ((14)C-PCB-153, and a congeneric mixture of [UL-(14)C]-labeled polychlorinated biphenyls ((14)C-PCB-Mix) was studied in cell suspension cultures of wheat (Triticum aestivum L. cv. 'Heines Koga II'). About 50% of applied (14)C-PCB-52 (20 μg/assay) was transformed during 96 h of incubation. While 7.6% on non-extractable residues emerged, turnover of (14)C-PCB-52 was mainly due to soluble polar metabolites. These were subjected to chemical glycoside cleavage. In the resulting hydrolysate, four aglycons were identified by GC-EIMS, namely four tetrachloro-hydroxy-biphenyl isomers (C6H6Cl4O, M(+·) at m/z = 306, 308, 310 and 312), and one trichloro-hydroxy-biphenyl (C6H7Cl3O, M(+·) at m/z = 272, 274 and 276). Number and character of hydroxylated products pointed to cytochromes P450 as enzymatic catalysts of hydroxylation. (14)C-PCB-153 was metabolized by wheat to minor degree if at all. Due to GC-EIMS analysis, of (14)C-PCB-Mix consisted of biphenyl, one mono-, four di-, seven tri-, eleven tetra-, and four pentachlorobiphenyls besides traces of further mono- and hexachlorobiphenyls. Among these were PCB-28, PCB-52, PCB 101, and PCB-118 (identified by seven key congeners standard). The mixture resembled industrial products Clophen A30 or Aroclor 1016. Metabolic turnover of applied (14)C-PCB-Mix (15 μg/assay) was 30% after 96 h; 8.4% of non-extractable residues emerged. Using DDE (p,p'-dichlorodiphenyl-dichloroethylene) as internal standard it was demonstrated that biphenyl, one monochloro-, two dichloro-, and one trichlorobiphenyl were completely metabolized to polar products. Partial metabolization occurred with one di-, five tri-, and four tetrachlorobiphenyls. Two tri-, four tetra-, and all pentachlorbiphenyls proved to be stable. Due to strong interference by matrix, evaluation of three congeners was not possible. In addition to wheat, results of similar experiments with cell cultures of other species are briefly mentioned.

Biotic and Abiotic Transformation Pathways of a Short-Chain Chlorinated Paraffin Congener, 1,2,5,6,9,10-C10H16Cl6, in a Rice Seedling Hydroponic Exposure System

“…The total amount of CP-4 in the planted exposure system reduced linearly (Figure S9, R 2 = 0.992) during the tested period, and only 21.4 ± 1.6% of the initial amount of parent compound was recovered in the seedling exposure system after 7 days, meaning that a great amount of CP-4 was constantly metabolized in rice seedlings. Because only the extractable CP-4 left in the exposure system was analyzed for a mass balance calculation, the sequestrated CP-4 and metabolites binding to the cell wall that were barely extracted with organic solvents − were included in the unrecovered CP-4. Thus, the Phase III metabolism of xenobiotics (sequestration of CP-4) , were even covered in the portion of CP-4 metabolized by rice seedlings.…”