title: Identification of toxic products of anthracene photomodification in simulated sunlight.
abstract: Currently, the evidence of a rapid photomodification of anthracene under sunlight resulting in enhanced toxicity exists; however, the chemical causes of toxicity are still unknown. The present study aimed at filling this gap by irradiation of an anthracene suspension with simulated sunlight and subsequent effect-directed fractionation and analysis of toxic products with respect to the inhibition of bacterial energy metabolism of Vibrio fischeri, reproduction of the green algae Scenedesmus vacuolatus, and genotoxicity in the umuC test. Algal toxicity of anthracene was hardly modified by irradiation prior to testing and distributed over all fractions with emphasis on the fractions containing anthracene-9,10-dione and a photometabolite suggested to be 10-hydroxyanthrone. Bacterial toxicity and genotoxicity in contrast emerged only when anthracene was irradiated. Anthracene-1,4-dione, a so-far-unknown trace photometabolite, was identified as a very potent toxicant dominating the toxicity of photomodified anthracene to V. fischeri. In genotoxic fractions, 1-hydroxyanthracene-9,10-dione and 1,4-dihydroxyanthracene-9,10-dione were identified and confirmed as genotoxicants. The results stress the potential of effect-directed analysis approaches in contrast to mere chemical analysis in studies aiming at toxicologically relevant photomodified substances.
authors.affiliation: Department of Chemical Ecotoxicology, UFZ Centre for Environmental Research Leipzig-Halle, Permoserstrasse 15, 04318 Leipzig, Germany. wb@uoe.ufz.de
authors.forename: Werner
authors.initials: W
authors.lastname: Brack
authors.forename: Rolf
authors.initials: R
authors.lastname: Altenburger
authors.forename: Eberhard
authors.initials: E
authors.lastname: Küster
authors.forename: Bettina
authors.initials: B
authors.lastname: Meissner
authors.forename: Klaus-Dieter
authors.initials: KD
authors.lastname: Wenzel
authors.forename: Gerrit
authors.initials: G
authors.lastname: Schüürmann
mesh_terms: D000873:Anthracenes / Q000737:chemistry* / Q000633:toxicity*; D004259:DNA-Directed DNA Polymerase; D029968:Escherichia coli Proteins / Q000235:genetics; D009152:Mutagenicity Tests; D010777:Photochemistry; D012486:Salmonella typhimurium / Q000235:genetics; D044444:Scenedesmus / Q000187:drug effects / Q000502:physiology; D013472:Sunlight; D014733:Vibrio; D014874:Water Pollutants, Chemical / Q000633:toxicity*
chemical_list: D000873:Anthracenes; D029968:Escherichia coli Proteins; D014874:Water Pollutants, Chemical; C078202:UmuC protein, E coli; D004259:DNA-Directed DNA Polymerase; C034020:anthracene