Departament d'Enginyeria Química and Institut de Ciència i Tecnologia Ambiental, Universitat Autònoma de Barcelona (UAB), 08193 Bellaterra, Spain.
Chemosphere. 2010 Jan;78(4):474-81. doi: 10.1016/j.chemosphere.2009.10.009. Epub 2009 Nov 12.
Ketoprofen is a nonsteroidal anti-inflammatory drug that has been detected in the environment in the range of ng L(-1)-microg L(-1) due to its low degradability in some wastewater treatment plants. In this study, the use of the white-rot fungus Trametes versicolor to effectively degrade ketoprofen in a defined liquid medium was assessed. The fungus eliminated ketoprofen to nondetectable levels in 24h when it was added at 10mgL(-1) whereas at low concentration of 40microgL(-1) it was almost completely removed (95%) after 5h. Low extracellular laccase activity was detected in the T. versicolor cultures but the addition of the laccase-mediator system did not lead to ketoprofen oxidation. The cytochrome P-450 inhibitor 1-aminobenzotriazole reduced ketoprofen oxidation. These data suggest that the first oxidation step is cytochrome P450 mediated. During time-course degradation experiments, three intermediates were structurally elucidated and quantified by HPLC-DAD-MS and NMR: 2-[3-(4-hydroxybenzoyl)phenyl]-propanoic acid, 2-[(3-hydroxy(phenyl)methyl)phenyl]-propanoic acid, and 2-(3-benzoyl-4-hydroxyphenyl)-propanoic acid. The latter was reported for the first time in biological systems. After 7 d of incubation, only small amounts of 2-[(3-hydroxy(phenyl)methyl)phenyl]-propanoic acid (0.08mg) remained in the liquid medium in comparison with the initial ketoprofen dose (1.0mg), suggesting possible mineralization of ketoprofen.
酮洛芬是一种非甾体抗炎药，由于其在一些污水处理厂中的低降解性，其在环境中的浓度范围为 ng L(-1)-μg L(-1)。在本研究中，评估了白腐真菌糙皮侧耳（Trametes versicolor）有效降解确定液体培养基中酮洛芬的能力。当真菌以 10mgL(-1)的浓度添加时，可在 24 小时内将酮洛芬消除至无法检测的水平，而在低浓度 40μg L(-1)时，5 小时后几乎完全去除（95%）。在糙皮侧耳培养物中检测到低细胞外漆酶活性，但添加漆酶-介体系统并未导致酮洛芬氧化。细胞色素 P-450 抑制剂 1-氨基苯并三唑降低了酮洛芬的氧化。这些数据表明，第一步氧化是细胞色素 P450 介导的。在时间过程降解实验中，通过 HPLC-DAD-MS 和 NMR 结构阐明并定量了三种中间体：2-[3-(4-羟基苯甲酰基)苯基]-丙酸、2-[(3-羟基（苯基）甲基）苯基]-丙酸和 2-(3-苯甲酰基-4-羟基苯基）-丙酸。后一种物质在生物系统中首次报道。在 7 天的孵育后，与初始酮洛芬剂量（1.0mg）相比，液体培养基中仅残留少量 2-[(3-羟基（苯基）甲基）苯基]-丙酸（0.08mg），表明酮洛芬可能被矿化。
