title: Biodegradation of tetrabromobisphenol A by oxidases in basidiomycetous fungi and estrogenic activity of the biotransformation products.
abstract: Tetrabromobisphenol A (TBBPA) degradation was investigated using white rot fungi and their oxidative enzymes. Strains of the Trametes, Pleurotus, Bjerkandera and Dichomitus genera eliminated almost 1 mM TBBPA within 4 days. Laccase, whose role in TBBPA degradation was demonstrated in fungal cultures, was applied to TBBPA degradation alone and in combination with cellobiose dehydrogenase from Sclerotium rolfsii. Purified laccase from Trametes versicolor degraded approximately 2 mM TBBPA within 5 h, while the addition of cellobiose dehydrogenase increased the degradation rate to almost 2.5 mM within 3 h. Laccase was used to prepare TBBPA metabolites 2,6-dibromo-4-(2-hydroxypropane-2-yl) phenol (1), 2,6-dibromo-4-(2-methoxypropane-2-yl) phenol (2) and 1-(3,5-dibromo-4-hydroxyphen-1-yl)-2,2',6,6'-tetrabromo-4,4'-isopropylidene diphenol (3). As compounds 1 and 3 were identical to the TBBPA metabolites prepared by using rat and human liver fractions (Zalko et al., 2006), laccase can provide a simple means of preparing these metabolites for toxicity studies. Products 1 and 2 exhibited estrogenic effects, unlike TBBPA, but lower cell toxicity.
authors.affiliation: Institute of Microbiology, Laboratory of Biotransformation, Academy of Sciences of the Czech Republic, Vídeňská 1083, 142 20 Prague 4, Czech Republic. brona@biomed.cas.cz
authors.forename: Bronislava
authors.initials: B
authors.lastname: Uhnáková
authors.forename: Roland
authors.initials: R
authors.lastname: Ludwig
authors.forename: Jana
authors.initials: J
authors.lastname: Pěknicová
authors.forename: Ladislav
authors.initials: L
authors.lastname: Homolka
authors.forename: Ludmila
authors.initials: L
authors.lastname: Lisá
authors.forename: Miroslav
authors.initials: M
authors.lastname: Šulc
authors.forename: Alena
authors.initials: A
authors.lastname: Petříčková
authors.forename: Fatima
authors.initials: F
authors.lastname: Elzeinová
authors.forename: Helena
authors.initials: H
authors.lastname: Pelantová
authors.forename: Daniela
authors.initials: D
authors.lastname: Monti
authors.forename: Vladimír
authors.initials: V
authors.lastname: Křen
authors.forename: Dietmar
authors.initials: D
authors.lastname: Haltrich
authors.forename: Ludmila
authors.initials: L
authors.lastname: Martínková
mesh_terms: D001487:Basidiomycota / Q000378:metabolism*; D001711:Biotransformation; D045744:Cell Line, Tumor; D004967:Estrogens / Q000378:metabolism*; D006801:Humans; D010088:Oxidoreductases / Q000378:metabolism*; D011075:Polybrominated Biphenyls / Q000378:metabolism*
chemical_list: D004967:Estrogens; D011075:Polybrominated Biphenyls; D010088:Oxidoreductases; C020806:tetrabromobisphenol A