Isomer-Specific Biodegradation of Nonylphenol in River Sediments and Structure-Biodegradability Relationship

Nonylphenol (NP), a well-known environmental estrogen with numerous isomers, is frequently found in surface water and sediments. Recent studies showed that NP isomers exhibited different estrogenicity. However, at present little information is available on its isomer-specific degradation in the bed sediment, which is the primary sink of NP in surface aquatic systems. In this study, we investigated the biodegradability of 19 NP isomers in two river sediments under oxic and anoxic conditions. Under oxic conditions, the half-lives of NP isomers in an upper river sediment ranged from 0.9 to 13.2 d. Under reduced conditions, the persistence of NP isomers generally increased, with negligible dissipation under strongly reduced conditions. In the well-aerated sediment, NP isomers with short side chain and/or bulky α-substituents were found to be more recalcitrant to degradation. Moreover, when a total of 57 molecular descriptors were examined, the degree of branching as quantified by IDWbar was found to result in the best linear correlation with half-lives of NP isomers (R2 = 0.88). These results indicated that the isomer-specificity of NP in environmental processes should be considered, and that simple molecular descriptors may be used to identify the more recalcitrant isomers, thus allowing prioritization in the evaluation of environmental fate and risks of NP isomers.