Effects of Nereis diversicolor on the Transformation of 1‑Methylpyrene and Pyrene: Transformation Efficiency and Identification of Phase I and II Products

Linus Mattias Valdemar Malmquist, Jan Henning Christensen, Henriette Selck

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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.
Translated title of the contributionEffekten af Nereis diversicolor på omdannelsen af 1-methylpyren og pyren: Omdannelseseffektivitet og identifikation af fase I og II produkter
Original languageEnglish
JournalEnvironmental Science & Technology (Washington)
Issue number10
Pages (from-to)5383-5392
Number of pages10
Publication statusPublished - 23 Apr 2013

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