Metabolism of the pesticide metabolites 4-nitrophenol and 3,4-dichloroaniline in carrot (Daucus carota) cell suspension cultures

The metabolism of [ 14 C]-4-nitrophenol and [ 14 C]-3,4-dichloroaniline (the xenobiotics are degradation products of parathion and propanil, respectively) was studied in cell suspension cultures of carrot (Daucus carota L.). 4-Nitrophenol was transformed almost quantitatively to water-soluble conjugates with minor amounts of non-extractable residues. The conjugates identified were 1-(O-β-D-glucopyranosyl)-4-nitrobenzene and 1-(6′-O-malonyl-O-β-D-glucopyranosyl)-4-nitrobenzene. In addition, two unidentified metabolites were observed, possibly a disaccharide and another malonylated glycoside of 4-nitrophenol. Time-course studies demonstrated that 4-nitrophenol was rapidly taken up and conjugated; all metabolites remained associated with the cells rather than nutrient medium. 3,4-Dichloroaniline was transformed quantitatively to water-soluble conjugates and bound residues (3.6%). The water-soluble metabolites were identified as 6′-O-malonyl-N-(β-D-glucopyranosyl)-3,4-dichloroaniline, N-(β-D-glucopyranosyl)-3,4-dichloroaniline and N-malonyl-3,4-dichloroaniline. A time-course study showed that the glucosides were formed initially, then decreased, possibly due to hydrolysis. This decrease was paralleled by an increase of the main metabolite, N-malonyl-3,4-dichloroaniline, which was predominantly recovered from the medium.