Effekten af Nereis diversicolor på omdannelsen af 1-methylpyren og pyren: Omdannelseseffektivitet og identifikation af fase I og II produkter

Linus Mattias Valdemar Malmquist, Jan Henning Christensen, Henriette Selck

Publikation: Bidrag til tidsskriftTidsskriftartikelForskningpeer review

Resumé

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.
Bidragets oversatte titelEffekten af Nereis diversicolor på omdannelsen af 1-methylpyren og pyren: Omdannelseseffektivitet og identifikation af fase I og II produkter
OriginalsprogEngelsk
TidsskriftEnvironmental Science & Technology (Washington)
Vol/bind47
Udgave nummer10
Sider (fra-til)5383-5392
Antal sider10
ISSN0013-936X
DOI
StatusUdgivet - 23 apr. 2013

Citer dette

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title = "Effects of Nereis diversicolor on the Transformation of 1‑Methylpyrene and Pyrene: Transformation Efficiency and Identification of Phase I and II Products",
abstract = "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-substitutedPAHs, whose toxicities are unknown. This study demonstrates the need to consider fate and effects of substituted PAHs and their metabolites in risk assessments.",
author = "Malmquist, {Linus Mattias Valdemar} and Christensen, {Jan Henning} and Henriette Selck",
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Effects of Nereis diversicolor on the Transformation of 1‑Methylpyrene and Pyrene : Transformation Efficiency and Identification of Phase I and II Products. / Malmquist, Linus Mattias Valdemar; Christensen, Jan Henning; Selck, Henriette.

I: Environmental Science & Technology (Washington), Bind 47, Nr. 10, 23.04.2013, s. 5383-5392.

Publikation: Bidrag til tidsskriftTidsskriftartikelForskningpeer review

TY - JOUR

T1 - Effects of Nereis diversicolor on the Transformation of 1‑Methylpyrene and Pyrene

T2 - Transformation Efficiency and Identification of Phase I and II Products

AU - Malmquist, Linus Mattias Valdemar

AU - Christensen, Jan Henning

AU - Selck, Henriette

PY - 2013/4/23

Y1 - 2013/4/23

N2 - 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-substitutedPAHs, whose toxicities are unknown. This study demonstrates the need to consider fate and effects of substituted PAHs and their metabolites in risk assessments.

AB - 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-substitutedPAHs, whose toxicities are unknown. This study demonstrates the need to consider fate and effects of substituted PAHs and their metabolites in risk assessments.

U2 - 10.1021/es400809p

DO - 10.1021/es400809p

M3 - Journal article

VL - 47

SP - 5383

EP - 5392

JO - Environmental Science & Technology (Washington)

JF - Environmental Science & Technology (Washington)

SN - 0013-936X

IS - 10

ER -