White-rot fungus-mediated degradation of the analgesic ketoprofen and identification of intermediates by HPLC-DAD-MS and NMR.
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.
Marco-Urrea
Ernest
E
Departament d'Enginyeria Química and Institut de Ciència i Tecnologia Ambiental, Universitat Autònoma de Barcelona (UAB), 08193 Bellaterra, Spain.
Pérez-Trujillo
Miriam
M
Cruz-Morató
Carles
C
Caminal
Gloria
G
Vicent
Teresa
T
D000700:Analgesics / Q000378:metabolism*; D001487:Basidiomycota / Q000378:metabolism; D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D007660:Ketoprofen / Q000378:metabolism*; D042845:Laccase / Q000378:metabolism*; D009682:Magnetic Resonance Spectroscopy / Q000379:methods*; D055454:Trametes / Q000378:metabolism*
D000700:Analgesics; D007660:Ketoprofen; D042845:Laccase