Metabolic fate of 2,4-dichlorophenol and related plant residues in rats.

This study compared the metabolic fate of [(14)C]-DCP, [(14)C]-residues from radish plants, and purified [(14)C]-DCP-(acetyl)glucose following oral administration in rats. A rapid excretion of radioactivity in urine occurred for [(14)C]-DCP, [(14)C]-DCP-(acetyl)glucose, and soluble residues, 69, 85, and 69% within 48 h, respectively. Radio-HPLC profiles of 0-24 h urine from rats fed [(14)C]-DCP and [(14)C]-DCP-(acetyl)glucose were close and qualitatively similar to those obtained from plant residues. No trace of native plant residues was detected under the study conditions. The structures of the two major peaks were identified by MS as the glucuronide and the sulfate conjugates of DCP. The characterization of a dehydrated glucuronide conjugate by MS and NMR of DCP was unusual. In contrast to soluble residues, bound residues were mainly excreted in feces, 90% within 48 h, whereas total residues were eliminated in both urine and feces. For total residues, the radioactivity in feces was higher than expected from the percentage of soluble and bound residues in radish plants. This result highlighted that less absorption took place when residues were present in the plant matrix as compared to plant-free residues and DCP.

Metabolic fate of [14C] chlorophenols in radish (Raphanus sativus), lettuce (Lactuca sativa), and spinach (Spinacia oleracea).

Chlorophenols are potentially harmful pollutants that are found in numerous natural and agricultural systems. Plants are a sink for xenobiotics, which occur either intentionally or not, as they are unable to eliminate them although they generally metabolize them into less toxic compounds. The metabolic fate of [ (14)C] 4-chlorophenol (4-CP), [ (14)C] 2,4-dichlorophenol (2,4-DCP), and [ (14)C] 2,4,5-trichlorophenol (2,4,5-TCP) was investigated in lettuce, spinach, and radish to locate putative toxic metabolites that could become bioavailable to food chains. Radish plants were grown on sand for four weeks before roots were dipped in a solution of radiolabeled chlorophenol. The leaves of six-week old lettuce and spinach were treated. Three weeks after treatments, metabolites from edible plant parts were extracted and analyzed by high performance liquid chromatography (HPLC) and characterized by mass spectrometry (MS), and nuclear magnetic resonance spectroscopy (NMR). Characterization of compounds highlighted the presence of complex glycosides. Upon hydrolysis in the digestive tract of animals or humans, these conjugates could return to the toxic parent compound, and this should be kept in mind for registration studies.