title: Mutagenicity, dioxin-like activity and bioaccumulation of alkylated picene and chrysene derivatives in a German lignite.
abstract: In a former study, a German lignite extract exhibited toxicity to Danio rerio and Caenorhabditis elegans and was shown to have mutagenic and dioxin-like activity. Besides the comparatively low content of known toxic polycyclic aromatic hydrocarbons (PAH), highly intensive peaks of m/z 274 and m/z 324 were observed during the chromatographic analysis. These compounds are assumed to be alkylated chrysenes and picenes (3,3,7-trimethyl-1,2,3,4-tetrahydrochrysene, 1,2-(1'-isopropylpropano)-7-methylchrysene and an isomer of the latter, 1,2,9-trimethyl-1,2,3,4-tetrahydropicene and 2,2,9-trimethyl-1,2,3,4-tetrahydropicene). These compounds are intermediates in the diagenetic formation of chrysene and picene from triterpenoids. Due to their general high abundance in lignites and the toxicity observed for the lignite extract, the mechanism-specific toxicity and bioavailability of these compounds were investigated in the present study using the approach of effect-directed analysis. After the separation of the compounds from other PAH, their mutagenic activity (Ames Fluctuation test) and dioxin-like activity (EROD activity) were studied. Both, mutation induction factor (up to 2.9±2.7) and dioxin-like activity (Bio-TEQ of 224±75 pg/g; represents the amount (pg) 2,3,7,8-tetrachlorodibenzo-p-dioxin per g coal that would provoke the same toxic effect) were rather low. Bioavailability estimated by the bioaccumulation test with Lumbriculus variegatus was also very limited. Based on the obtained results, the environmental risk of the highly abundant alkylated chrysenes and picenes in lignites is concluded to be low.
authors.affiliation: University of Münster, Institute of Geology and Palaeontology-Applied Geology, Corrensstrasse 24, 48149 Münster, Germany.
authors.forename: Wiebke
authors.initials: W
authors.lastname: Meyer
authors.affiliation: RWTH Aachen University, Institute for Environmental Research, Department of Ecosystem Analysis, Worringerweg 1, 52074 Aachen, Germany.
authors.forename: Thomas-Benjamin
authors.initials: TB
authors.lastname: Seiler
authors.affiliation: University of Münster, Institute of Geology and Palaeontology-Applied Geology, Corrensstrasse 24, 48149 Münster, Germany.
authors.forename: Andreas
authors.initials: A
authors.lastname: Christ
authors.affiliation: RWTH Aachen University, Institute for Environmental Research, Department of Ecosystem Analysis, Worringerweg 1, 52074 Aachen, Germany.
authors.forename: Regine
authors.initials: R
authors.lastname: Redelstein
authors.affiliation: J.W.Goethe-University Frankfurt am Main, Institute for Atmospheric and Environmental Sciences, Department of Environmental Analytical Chemistry, Altenhöferallee 1, 60438 Frankfurt/Main, Germany.
authors.forename: Wilhelm
authors.initials: W
authors.lastname: Püttmann
authors.affiliation: RWTH Aachen University, Institute for Environmental Research, Department of Ecosystem Analysis, Worringerweg 1, 52074 Aachen, Germany; Key Laboratory of Yangtze River Environment of Education, Ministry of China, College of Environmental Science and Engineering, Tongji University, Shanghai 200092, China; College of Resources and Environmental Science, Chongqing University, Chongqing 400030, China; School of Environment, Nanjing University, China.
authors.forename: Henner
authors.initials: H
authors.lastname: Hollert
authors.affiliation: University of Münster, Institute of Geology and Palaeontology-Applied Geology, Corrensstrasse 24, 48149 Münster, Germany. Electronic address: achten@uni-muenster.de.
authors.forename: Christine
authors.initials: C
authors.lastname: Achten
mesh_terms: D000478:Alkylation; D002911:Chrysenes / Q000633:toxicity*; D003031:Coal / Q000633:toxicity; D004147:Dioxins / Q000633:toxicity*; D009153:Mutagens / Q000633:toxicity*
chemical_list: D002911:Chrysenes; D003031:Coal; D004147:Dioxins; D009153:Mutagens; C031180:chrysene; C056699:picene
keywords: Ames Fluctuation test; Bioavailability; EROD assay; Effect-directed analysis (EDA); Lumbriculus variegatus; Polycyclic aromatic hydrocarbons