Transformation of ring-(14)C-labelled tetrabromobisphenol-A (TBBPA) was studied in an oxic soil slurry with and without amendment with Sphingomonas sp. strain TTNP3, a bacterium degrading bisphenol-A. TBBPA degradation was accompanied by mineralization and formation of metabolites and bound-residues. The biotransformation was stimulated in the slurry bio-augmented with strain TTNP3, via a mechanism of metabolic compensation, although this strain did not grow on TBBPA. In the absence and presence of strain TTNP3, six and nine metabolites, respectively, were identified. The initial O-methylation metabolite (TBBPA-monomethyl ether) and hydroxytribromobisphenol-A were detected only when strain TTNP3 was present. Four primary metabolic pathways of TBBPA in the slurries are proposed: oxidative skeletal rearrangements, O-methylation, ipso-substitution, and reductive debromination. Our study provides for the first time the information about the complex metabolism of TBBPA in oxic soil and suggests that type II ipso-substitution could play a significant role in the fate of alkylphenol derivatives in the environment.

中文翻译：

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在没有和有烷基酚降解细菌Sphingomonas sp。的情况下，四溴双酚A在土壤淤浆中的命运和代谢。菌株TTNP3。

研究了在有或没有用鞘氨醇单胞菌修饰的含氧土壤浆液中环（14）C标记的四溴双酚-A（TBBPA）的转化。菌株TTNP3，一种降解双酚A的细菌。TBBPA降解伴随着矿化作用，代谢产物和结合残留物的形成。尽管该菌株未在TBBPA上生长，但它通过代谢补偿机制刺激了以TTNP3菌株生物增强的浆液中的生物转化。在不存在和存在菌株TTNP3的情况下，分别鉴定出6种和9种代谢物。仅当存在TTNP3菌株时，才检测到初始的O-甲基化代谢产物（TBBPA-单甲醚）和羟基三溴双酚-A。提出了TBBPA在浆液中的四个主要代谢途径：氧化性骨架重排，O-甲基化，ipso取代，和还原性脱溴。我们的研究首次提供了含氧土壤中TBBPA复杂代谢的信息，并表明II型ipso取代可在环境中烷基酚衍生物的命运中发挥重要作用。