Formation of phthalates during the degradation of N-phenyl-2-naphthylamine by soil bacteria

Abstract

N-phenyl-2-naphthylamine (N-PNA) and phthalates are classified as antibiotic substances. The appearance and accumulation of these substances in the biosphere is associated with their technogenic and biogenic origin (metabolites of plants and bacteria). In this article, we compare the degrading action of such soil bacteria as Rhizobium leguminosarum bv. viceae, Bradyrhizobium japonicum, Pseudomonas syringae pv. pisi, Clavibacter michiganensis sps. Sepedonicus and Azotobacter chroococcum against N-PNA. These bacteria differ in their interaction with pea plants (Pisum sativum L.) synthesising N-PNA. The degradation products were studied using gas chromatography-mass spectrometry in ethyl acetate extracts obtained from culture liquid media, in which N-PNA at a concentration of 10 μM and the bacteria under study were introduced. The decrease in the N-PNA concentration in the extracts obtained using ethyl acetate from culture media, in which N-PNA had been added to a concentration of 100 μM, was monitored following two days of bacterial growth using the methods of high-performance liquid chromatography. It was shown that all the studied bacterial species are capable of degrading N-PNA with the formation of phthalates. The Rhizobium bacteria, endosymbionts of pea plants synthesising N-PNA, and free-living nitrogen-fixing bacteria of the Azotobacter genus showed the highest degrading activity. It was found that N-PNA reduced the viability of all types of bacteria, although to a varying degree. N-PNA had the most negative effect on the viability of the Azotobacter genus, although these bacteria showed a high degrading action against N-PNA. The dependence between the negative effect of NPNA on bacterial viability and the N-PNA concentration was mildly pronounced for Rhizobium and Pseudomonas, although being significant for Bradyrhizobium and Clavibacter.