title: In vivo metabolism and organ distribution of a branched 14C-nonylphenol isomer in pond snails, Lymnaea stagnalis L.
abstract: The branched isomers of p-nonylphenol (NP) are perceived to be more resistant to biodegradation in aquatic environments as well as to have more estrogen-like toxicity than the straight chain isomers. By use of GC-MS, some of them have been identified and found to exist in higher concentrations in the isomeric compound mixture than the straight chain isomers. The investigations of the distribution and metabolism of these branched isomers in aquatic organisms are therefore considered to be important in understanding the mechanisms of toxicity of NP. A single tertiary isomer of NP, 4(3'-,6'-dimethyl-3'-heptyl)-phenol, was synthesized in the laboratory and used in in vivo studies of its organ distribution and metabolism in Lymnaea stagnalis L., following a constant exposure of the organisms to 14C-NP isomer in water over a period of 8 days at an average exposure concentration of 105 ppb (range: 93-116 ppb). The results obtained clearly showed the distribution and bioconcentration of the isomer residues in various internal organs of Lymnaea after uptake in water and food. Analysis of the extracts of the organ tissues and faeces by HPLC and GC-MS after digestion with Pankreatin/beta-glucuronidase and nitric acid, respectively, showed that the isomer was metabolized by conjugation to glucuronic acid and hydroxylation to a catechol. The findings from these studies and their implications in the biotransformation and estrogenicity of NP in Lymnaea stagnalis L. are further discussed in detail in this paper.
authors.affiliation: Institut für Okologische Chemie, GSF-Forschungszentrum für Umwelt und Gesundheit, Ingolstädter Landstrasse 1, D-85764 Neuherberg, Muenchen, Germany.
authors.forename: J O
authors.initials: JO
authors.lastname: Lalah
authors.forename: K-W
authors.initials: KW
authors.lastname: Schramm
authors.forename: G F
authors.initials: GF
authors.lastname: Severin
authors.forename: D
authors.initials: D
authors.lastname: Lenoir
authors.forename: B
authors.initials: B
authors.lastname: Henkelmann
authors.forename: A
authors.initials: A
authors.lastname: Behechti
authors.forename: K
authors.initials: K
authors.lastname: Guenther
authors.forename: A
authors.initials: A
authors.lastname: Kettrup
mesh_terms: D000818:Animals; D001711:Biotransformation; D002851:Chromatography, High Pressure Liquid; D005243:Feces / Q000737:chemistry; D008401:Gas Chromatography-Mass Spectrometry; D020723:Glucuronic Acid; D006900:Hydroxylation; D007536:Isomerism; D008195:Lymnaea; D010636:Phenols / Q000378:metabolism* / Q000493:pharmacokinetics*; D011960:Receptors, Estrogen / Q000187:drug effects / Q000502:physiology; D014018:Tissue Distribution
chemical_list: D010636:Phenols; D011960:Receptors, Estrogen; C025256:nonylphenol; D020723:Glucuronic Acid