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首页> 外文期刊>Environmental Science & Technology >Steroidal Aromatic 'Naphthenic Acids' in Oil Sands Process-Affected Water: Structural Comparisons with Environmental Estrogens
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Steroidal Aromatic 'Naphthenic Acids' in Oil Sands Process-Affected Water: Structural Comparisons with Environmental Estrogens

机译：受油砂加工影响的水中的甾族环烷酸：与环境雌激素的结构比较

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摘要

The large volumes, acute toxicity, estrogenicity, and antiandrogenitity of process-affected waters accruing in tailings ponds from the operations of the Alberta oil sands industries pose a significant task for environmental reclamation. Synchronous fluorescence spectra (SFS) suggest that oil sands process-affected water (OSPW) may contain aromatic car-boxylic acids, which are among the potentially environmentally important toxicants, but no such acids have yet been identified, limiting interpretations of the results of estrogenicity and other assays. Here we show that multidimensional comprehensive gas chromatography—mass spectrometry (GCxGC-MS) of methyl esters of acids in an OSPW sample produces mass spectra consistent with their assignment as C_19 and C_20 C-ring monoaromatic hydroxy steroid acids, D-ring opened hydroxy and nonhydroxy poryhydrophenanthroic acids with one aromatic and two alfcyclic rings and A-ring opened steroidal keto acids. High resolution MS data support the assignment of several of the so-called O3' species. When fractions of distilled, esterined, OSPW acid-extractable organics were examined, the putative aromatics were mainly present in a high boiling fraction; when examined by argentation thin layer chromatography, some were present in a fraction with a retardation factor between that of the methyl esters of synthetic monoalicyclic and monoaromatic acids. Ultraviolet absorption spectra of these fractions indicated the presence of benzenoid moieties. SFS of model octahydro- and tetrahydrophenanthroic acids produced emissions at the characteristic excitation wavelengths observed in some OSPW extracts, consistent with the postulations from ultraviolet spectroscopy and mass spectrometry data. We suggest the acids originate from extensive btodegradarjon of C-ring monoaromatic steroid hydrocarbons and offer a means of differentiating residues at different biodegradab'on stages in tailings ponds. Structural similarities with estrone and estradiol imply that such compounds may account for some of the environmental estrogenic activity reported in OSPW acid-extractable organics and naphthenic acids.
机译：艾伯塔省油砂工业的运营所产生的尾矿池中大量的，受过程影响的水具有急性毒性，雌激素性和抗雄激素性，这对环境开垦是一项重大任务。同步荧光光谱（SFS）表明，受油砂加工影响的水（OSPW）可能含有芳族羧酸，这是对环境潜在重要的毒物，但尚未发现此类酸，这限制了对雌激素性结果的解释和其他检测。在这里，我们显示了OSPW样品中酸的甲酯的多维综合气相色谱-质谱（GCxGC-MS）产生的质谱与其分配一致，分别为C_19和C_20 C环单芳族羟基甾体酸，D环开环羟基和带有一个芳香族环和两个杂环和一个A环的非羟基多氢邻苯二酸，可打开甾族酮酸。高分辨率MS数据支持指定几种所谓的O3'物质。当检查馏出的，酯化的，OSPW酸可萃取的有机物的馏分时，推定的芳族化合物主要以高沸点馏分的形式存在。当通过银联薄层色谱法检查时，一些以延迟因子存在于合成的单脂环酸和单芳族酸的甲酯之间的馏分中。这些级分的紫外线吸收光谱表明存在苯甲酸酯部分。在某些OSPW提取物中观察到的模型八氢和四氢邻苯二甲酸的SFS在特征激发波长处产生发射，这与紫外光谱和质谱数据的假设相符。我们建议这些酸源自C环单芳族甾族烃的大量btodegradarjon，并提供了一种区分尾矿池中不同生物降解阶段残留物的方法。与雌酮和雌二醇的结构相似性暗示此类化合物可能是OSPW酸可萃取有机物和环烷酸中报道的某些环境雌激素活性的原因。

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  • 来源
    《Environmental Science & Technology》 |2011年第22期|p.9806-9815|共10页
  • 作者

    Steven J. Rowland; Charles E. West; David Jones; Alan G. Scarlett; Richard A. Frank; L. Mark Hewitt;

  • 作者单位

    Petroleum and Environmental Geochemistry Group, Biogeochemistry Research Centre, University of Plymouth, Drake Circus,Plymouth PL4 8AA, U.K;

    Petroleum and Environmental Geochemistry Group, Biogeochemistry Research Centre, University of Plymouth, Drake Circus,Plymouth PL4 8AA, U.K;

    Petroleum and Environmental Geochemistry Group, Biogeochemistry Research Centre, University of Plymouth, Drake Circus,Plymouth PL4 8AA, U.K;

    Petroleum and Environmental Geochemistry Group, Biogeochemistry Research Centre, University of Plymouth, Drake Circus,Plymouth PL4 8AA, U.K;

    Aquatic Ecosystems Protection Research Division/Water Science & Technology Directorate, Environment Canada,867 Lakeshore Road, Burlington, ON, Canada L7R 4A6;

    Aquatic Ecosystems Protection Research Division/Water Science & Technology Directorate, Environment Canada,867 Lakeshore Road, Burlington, ON, Canada L7R 4A6;

  • 收录信息 美国《科学引文索引》(SCI);美国《工程索引》(EI);美国《生物学医学文摘》(MEDLINE);美国《化学文摘》(CA);
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