Transformation of nonsubstituted and alkyl-substituted polycyclic aromatic hydrocarbons (PAHs) by the benthic invertebrate Nereis diversicolor was compared in this study. Pyrene and 1-methylpyrene were used as model compounds for nonsubstituted and alkyl-substituted PAHs, respectively. Qualitative and quantitative analyses of metabolites and parent compounds in worm tissue, water, and sediment were performed. Transformation of 1-methylpyrene generated the benzylic hydroxylated phase I product, 1-pyrenecarboxylic acid that comprised 90% of the total metabolites of 1-methylpyrene, and was mainly found in water extracts. We tentatively identified 1-methylpyrene glucuronides and 1-carbonylpyrene glycine as phase II metabolites not previously reported in literature. Pyrene was biotransformed to 1-hydroxypyrene, pyrene-1-sulfate, pyrene-1-glucuronide, and pyrene glucoside sulfate, with pyrene-1-glucuronide as the most prominent metabolite. Transformation of 1-methylpyrene (21% transformed) was more than 3 times as efficient as pyrene transformation (5.6% transformed). Because crude oils contain larger amounts of C1−C4-substituted PAHs than nonsubstituted PAHs, the rapid and efficient transformation of sediment-associated 1-methylpyrene may result in a high exposure of water-living organisms to metabolites of alkyl-substituted PAHs, whose toxicities are unknown. This study demonstrates the need to consider fate and effects of substituted PAHs and their metabolites in risk assessments.
|Publication date||Sep 2013|
|Number of pages||1|
|Publication status||Published - Sep 2013|
|Event||2013 International Symposium on Polycyclic Aromatic Compounds - Oregon State University , Corvallis, Oregon, United States|
Duration: 8 Sep 2013 → 12 Sep 2013
|Conference||2013 International Symposium on Polycyclic Aromatic Compounds|
|Location||Oregon State University|
|Period||08/09/2013 → 12/09/2013|
Malmquist, L. M. V., Christensen, J. H., & Selck, H. (2013). Effects of Nereis diversicolor on the Transformation of 1-Methylpyrene and Pyrene: Transformation Efficiency and Identification of Phase I and II Products. Poster session presented at 2013 International Symposium on Polycyclic Aromatic Compounds, Corvallis, Oregon, United States.