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首页> 外文期刊>Environmental Science & Technology >Enantioselective Transport and Biotransformation of Chiral Hydroxylated Metabolites of Polychlorinated Biphenyls in Whole Poplar Plants
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Enantioselective Transport and Biotransformation of Chiral Hydroxylated Metabolites of Polychlorinated Biphenyls in Whole Poplar Plants

机译：杨树全植物中多氯联苯的手性羟基化代谢产物的对映选择性转运和生物转化

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摘要

Hydroxylated metabolites of polychlorinated biphenyls (OH-PCBs) have been found to be ubiquitous in the environment due to the oxidative metabolism of their parent PCBs. With more polarity, OH-PCBs may be more toxic and mobile than their parent compounds. However, the behavior and fate of OH-PCBs have been neglected in the environment because they are not the original contaminants. Some of these hydroxylated metabolites are chiral, and chiral compounds can be used to probe biological metabolic processes. Therefore, chiral OH-PCBs were selected to study their uptake, translocation, transformation, and enantioselectivity in plants in this work. Poplars (Populus deltoides X nigra, DN34), a model plant with complete genoinic sequence, were hydroponically exposed to 5-hydroxy-2,2',3,4',6-pentachlorobiphenyi (5-OH-PCB91) and 5-hydroxy-2,2',3,5',6-pentachlorobiphenyl (5-OH-PCB9S) for 10 days. Chiral 5-OH-PCB91 and 5-OH-PCB95 were dearly shown to be sorbed, taken up, and translocated in whole poplars, and they were detected in various tissues of whole poplars. However, the enantioselectivity of poplar for 5-OH-PCB91 and 5-OH-PCB95 proved to be quite different. The second-eluting enantiomer of OH-PCB95, separated on a chiral column (Phenomena Lux Cellulose-1), was enantioselectively removed in whole poplar. Enantiomeric fractions in the middle xylem, top bark, top xylem, and stem, reached 0.803 ± 0.022, 0.643 ±0.110,0.835 ± 0.087, and 0.830 ± 0.029, respectively. Therefore, 5-OH-PCB95 was significantly enantioselectively biotransformed inside poplar tissues, in contrast to nearly racemic mixtures of 5-OH-PCB95 remaining in hydroponic solutions. Unlike 5-OH-PCB95, 5-OH-PCB91 remained nearly racemic in most tissues of whole poplars during 10 day exposure, suggesting the enantiomers of 5-OH-PCB91 were equally transported and metabolized in whole poplars. This is the first evidence of enantioselectivity of chiral OH-PCBs and suggests that poplars can enantioselectively biotransform at least one chiral OH-PCB: namely, 5-OH-PCB95.
机译：由于其母体多氯联苯的氧化代谢，已发现多氯联苯（OH-PCBs）的羟基化代谢产物在环境中无处不在。具有更多极性的OH-PCBs与其母体化合物相比可能更具毒性和移动性。但是，OH-PCBs的行为和命运在环境中已被忽略，因为它们不是原始污染物。这些羟基化代谢物中的一些是手性的，手性化合物可用于探测生物代谢过程。因此，在这项工作中，选择手性OH-PCBs来研究其在植物中的吸收，易位，转化和对映选择性。将具有完整遗传序列的模型植物白杨（Populus deltoides X nigra，DN34）静水暴露于5-hydroxy-2,2'，3,4'，6-pentachlorobiphenyi（5-OH-PCB91）和5-hydroxy -2,2'，3,5'，6-五氯联苯（5-OH-PCB9S）历时10天。强烈显示手性5-OH-PCB91和5-OH-PCB95在整个杨树中被吸附，吸收和转运，并在整个杨树的各种组织中检测到它们。然而，杨树对5-OH-PCB91和5-OH-PCB95的对映选择性被证明是完全不同的。在手性柱上分离的OH-PCB95的第二种洗脱对映异构体（Phenomena Lux Cellulose-1），在整个杨树中被对映选择性去除。中木质部，顶部树皮，顶部木质部和茎中的对映体分数分别达到0.803±0.022、0.643±0.110、0.835±0.087和0.830±0.029。因此，与5-OH-PCB95几乎残留在水培溶液中的外消旋混合物相比，5-OH-PCB95在杨树组织内部具有明显的对映选择性生物转化。与5-OH-PCB95不同，在暴露10天的整个杨树的大部分组织中，5-OH-PCB91几乎保持外消旋状态，这表明5-OH-PCB91的对映异构体在整个杨树中均被转运和代谢。这是手性OH-PCBs对映选择性的第一个证据，表明白杨可以对映体选择性地生物转化至少一种手性OH-PCB，即5-OH-PCB95。

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  • 来源
    《Environmental Science & Technology》 |2014年第20期|12213-12220|共8页
  • 作者

    Guangshu Zhai; Sarah M. Gutowski; Hans-Joachim Lehmler; Jerald L. Schnoor;

  • 作者单位

    Department of Civil and Environmental Engineering and IIHR Hydroscience and Engineering, The University of Iowa Iowa Citv Iowa 52242, United States;

    Department of Civil and Environmental Engineering and IIHR Hydroscience and Engineering, The University of Iowa Iowa Citv Iowa 52242, United States;

    Department of Occupational and Environmental Health, The University of Iowa, Iowa City, Iowa 52242, United States;

    Department of Civil and Environmental Engineering and IIHR Hydroscience and Engineering, The University of Iowa Iowa Citv Iowa 52242, United States,Department of Occupational and Environmental Health, The University of Iowa, Iowa City, Iowa 52242, United States;

  • 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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