Among the various types of industry-generated effluents, those containing phenolic compounds are serious recalcitrant. There is therefore a need to develop new technologies that emphasize the depletion of these pollutants from the environment, and that work as a viable alternative to traditional physical and chemical remediation methods. Filamentous fungi are capable of producing a great number of enzymes that efficiently transform several organic compounds. Despite the use of fungi as first-choice agents for bioremediation of hazardous contaminants, the definitions of the chemical reactions and products that are included in the fungal transformation processes still are poorly reported. In this work, Aspergillus brasiliensis efficiently transformed methyl p-coumarate under an unexpected way into two new compounds, 5-(oxiran-2-yl)benzene-1,2,3-triol (23.03%) and 4-(3-hydroxyoxiran-2-yl)benzene-1,2-diol (4.90%), along with acetophenone (72.07%). The chemical structures of derivatives were determined by gas chromatography coupled to mass spectrometry (GC-MS) analysis and a plausible bioremediation pathway for phenolic recalcitrant was proposed. Interestingly, the uncommon phenyloxirane moiety has been formed as part of the transformation from 4-vinylphenol intermediate through double bond oxidation. Certainly, our results will open new insights in the bioremediation of phenolic compounds and they will be useful guidance for future planning of other similar processes.

在各种类型的工业产生的废水中，含有酚类化合物的废水是严重的顽固性物质。因此，需要开发新技术，以强调从环境中消耗掉这些污染物，并作为传统的物理和化学修复方法的可行替代方法。丝状真菌能够产生大量能有效转化几种有机化合物的酶。尽管使用真菌作为有害污染物生物修复的首选试剂，但真菌转化过程中包括的化学反应和产物的定义仍然报道不多。在这项工作中，巴西曲霉有效地转化了甲基p-香豆酸酯以意外的方式变成了两个新化合物，5-（环氧乙烷-2-基）苯-1,2,3-三醇（23.03％）和4-（3-羟基环氧乙烷-2-基）苯-1,2 -二醇（4.90％），以及苯乙酮（72.07％）。通过气相色谱-质谱联用（GC-MS）分析确定衍生物的化学结构，并提出了酚类顽固剂的合理生物修复途径。有趣的是，作为从4-乙烯基苯酚中间体通过双键氧化的转化的一部分，已经形成了不常见的苯基环氧乙烷部分。当然，我们的结果将为酚类化合物的生物修复开辟新的见解，并将为今后其他类似工艺的规划提供有用的指导。