White Rot Fungi Produce Novel Tire Wear Compound Metabolites and Reveal Underappreciated Amino Acid Conjugation Pathways.

White Rot Fungi Produce Novel Tire Wear Compound Metabolites and Reveal Underappreciated Amino Acid Conjugation Pathways.
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DOI:
10.1021/acs.estlett.2c00114
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发表时间:
2022-05-10
影响因子:
10.9
通讯作者:
LeFevre, Gregory H.
LeFevre, Gregory H.
中科院分区:
环境科学与生态学2区
文献类型:
--
作者:
Wiener, Erica A.;LeFevre, Gregory H.

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随着越来越多的证据表明其毒性和在环境中的广泛检测,人们越来越关注地表水和雨水中的轮胎磨损化合物(TWC)。由于TWC在雨水中普遍存在,因此需要了解命运和处理方案,包括绿色基础设施中的生物转化(例如,生物滞留)。特别是,真菌的生物转化是没有很好地研究在雨水的情况下,尽管已知的某些真菌的能力,以消除柠檬酸盐污染物。在这里,我们首次报道了真菌生物转化三氯乙酸乙酰苯胺和六甲氧基甲基三聚氰胺(HMMM)的研究。我们发现,模式白色腐菌,变色栓菌,去除乙酰苯胺和六甲基三胺,分别为81.9%和69.6%,没有显着的吸附到生物量。不除去双环胺1,3-二苯基胍。此外,我们通过高分辨率质谱法使用半非靶向代谢组学鉴定了新的TWC代谢物。关键代谢物包括HMMM生物转化产物的多种异构体,作为HMMM的可能“死端”产物的三聚氰胺(用真实标准验证),以及乙酰苯胺的谷氨酰胺缀合产物。这些代谢物对环境毒性和治疗有影响。我们发现的第一个真菌谷氨酰胺结合的产品突出了需要调查氨基酸结合作为一个重要的途径,在生物转化的污染物,在其他领域的影响,包括天然产物的发现。
There is increasing concern about tire wear compounds (TWCs) in surface water and stormwater as evidence grows on their toxicity and widespread detection in the environment. Because TWCs are prevalent in stormwater, there is a need to understand fate and treatment options including biotransformation in green infrastructure (e.g., bioretention). Particularly, fungal biotransformation is not well-studied in a stormwater context despite the known ability of certain fungi to remove recalcitrant contaminants. Here, we report the first study on fungal biotransformation of the TWCs acetanilide and hexamethoxymethylmelamine (HMMM). We found that the model white rot fungus, Trametes versicolor, removed 81.9% and 69.6% of acetanilide and HMMM, respectively, with no significant sorption to biomass. The bicyclic amine 1,3-diphenylguanidine was not removed. Additionally, we identified novel TWC metabolites using semi-untargeted metabolomics via high-resolution mass spectrometry. Key metabolites include multiple isomers of HMMM biotransformation products, melamine as a possible “dead-end” product of HMMM (verified with an authentic standard), and a glutamine-conjugated product of acetanilide. These metabolites have implications for environmental toxicity and treatment. Our discovery of the first fungal glutamine-conjugated product highlights the need to investigate amino acid conjugation as an important pathway in biotransformation of contaminants, with implications in other fields including natural products discovery.
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