White-rot fungus-mediated degradation of the analgesic ketoprofen and identification of intermediates by HPLC–DAD–MS and NMR

Marco‐Urrea, Ernest; Pérez‐Trujillo, Míriam; Cruz-Morató, Carles; Caminal, Glòria; Vicent, Teresa

doi:10.1016/j.chemosphere.2009.10.009

Cited by 109 publications

(68 citation statements)

References 24 publications

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“…Recently, it was reported that degradation of pharmaceuticals contained in real sewage sludges by the white rot fungus Trametes versicolor in solid-phase and bioslurry systems is now underway in their research group and preliminary assays revealed promising results (Marco-Urrea et al 2009b). These research approaches would be useful for the practical application of white rot fungi to the pharmaceutical degradation.…”

Section: Discussionmentioning

confidence: 98%

Removal of diclofenac and mefenamic acid by the white rot fungus Phanerochaete sordida YK-624 and identification of their metabolites after fungal transformation

et al. 2010

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The non-steroidal anti-inflammatory drugs diclofenac (DCF) and mefenamic acid (MFA) were treated with the white rot fungus Phanerochaete sordida YK-624. DCF completely disappeared and MFA decreased by about 90% after 6 days of treatment. It was also confirmed that the fungus almost completely removed the acute lethal toxicity of DCF and MFA towards the freshwater crustacean Thamnocephalus platyurus after 6 days of treatment. Mass spectrometric and (1)H nuclear magnetic resonance analyses demonstrated that two mono-hydroxylated DCFs (4'-hydroxydiclofenac and 5-hydroxydiclofenac) and one di-hydroxylated DCF (4',5-dihydroxydiclofenac) were formed via fungal transformation. The four metabolites of MFA were identified as 3'-hydroxymethylmefenamic acid (mono-hydroxylated MFA), 3'-hydroxymethyl-5-hydroxymefenamic acid (di-hydroxylated MFA), 3'-hydroxymethyl-6'-hydroxymefenamic acid (di-hydroxylated MFA) and 3'-carboxymefenamic acid. These results suggest that hydroxylation catalyzed by cytochrome P450 (CYP) in P. sordida YK-624 may be involved in the elimination and detoxification of DCF and MFA. This notion was further supported by the fact that smaller decreases in DCF and MFA were observed in cultures of P. sordida YK-624 incubated with 1-aminobenzotriazole, a known inhibitor of CYP.

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Section: Discussionmentioning

confidence: 98%

Removal of diclofenac and mefenamic acid by the white rot fungus Phanerochaete sordida YK-624 and identification of their metabolites after fungal transformation

et al. 2010

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“…Anew, fungi have also proven to be efficient in degrading carbamazepine [55], even under non-sterile conditions [56]. Carbamazepine degradation can be mainly attributed to the production of fungal enzymes such as manganese peroxidase and versatile peroxidase [57], although the cytochrome P450 also plays a key role in degradation [57][58].…”

Section: Potential Applications and Challengesmentioning

confidence: 99%

“…Particularly, systems with fungal pellets have been used to remove pharmaceuticals including analgesics, anti-inflammatories, β-blockers, psychiatric drugs, antibiotics and anticancer drugs [55,58,69,89,90,129,130], as well as other toxic compounds coming from hospital wastewater such as radiocontrast agents [129].…”

Section: Removal Of Pharmaceutical Compoundsmentioning

confidence: 99%

Fungal pelleted reactors in wastewater treatment: Applications and perspectives

Espinosa-Ortiz

Rene

Pakshirajan

et al. 2016

Chemical Engineering Journal

197

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“…This suggests that the biotransformation of the drug by whole fungal cultures may probably also be effected by intracellular oxidizing activities (Tran et al 2010). Marco-Urrea et al (2010b) identified three metabolites of ketoprofen transformation by Trametes versicolor: 2-[(3-hydroxy(phenyl)methyl)phenyl]-propanoic acid, the major degradation metabolite formed by reduction of the ketone group, and 2-(3-benzoyl-4-hydroxyphenyl)propanoic acid and/or 2-(3-(4-hydroxybenzoyl)phenyl)propanoic acid, which were formed by hydroxylation (Fig. 3).…”

Section: Biodegradation/biotransformation Of Ketoprofenmentioning

confidence: 99%

“…Ketoprofen 2-(3-benzoylphenyl)propanoic acid is a type of PNSAID which has been detected in soil, surface water and in influents and effluents of wastewater treatment plants in concentrations ranging from ng l -1 up to lg l -1 (Xu et al 2009;Marco-Urrea et al 2010b;Almeida et al 2013). Adsorption and transformation of ketoprofen in soil are among the processes dependent on biotic and abiotic factors in soil.…”

Section: Biodegradation/biotransformation Of Ketoprofenmentioning

confidence: 99%

Biodegradation and biotransformation of polycyclic non-steroidal anti-inflammatory drugs

Domaradzka

Guzik

Wojcieszyńska

2015

Rev Environ Sci Biotechnol

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In recent years the increased use of polycyclic non-steroidal anti-inflammatory drugs has resulted in their presence in the environment. This in turn may cause potential negative effects on living organisms. While the biotransformation mechanisms of polycyclic non-steroidal anti-inflammatory drugs in the human body and in other mammals have been extensively studied, degradation of these drugs by microorganisms has seldom been investigated and is largely unknown. Biotransformation/biodegradation of polycyclic nonsteroidal anti-inflammatory drugs is caused by fungal microorganisms, mainly white-rot fungi, and a few strains of bacteria. However, hitherto only complete degradation of olsazine was described. The first step of the transformation is most often hydroxylation catalyzed by cytochrom P-450 monooxygenases, or oxygenation by laccases and three peroxidases: lignin peroxidase, manganese-dependent peroxidase and versatile peroxidase manganese-dependent peroxidase. The aim of this work is to summarize the knowledge about the biotransformation and/or biodegradation of polycyclic non-steroidal anti-inflammatory drugs and to present their biotransformation pathways.

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White-rot fungus-mediated degradation of the analgesic ketoprofen and identification of intermediates by HPLC–DAD–MS and NMR

Cited by 109 publications

References 24 publications

Removal of diclofenac and mefenamic acid by the white rot fungus Phanerochaete sordida YK-624 and identification of their metabolites after fungal transformation

Removal of diclofenac and mefenamic acid by the white rot fungus Phanerochaete sordida YK-624 and identification of their metabolites after fungal transformation

Fungal pelleted reactors in wastewater treatment: Applications and perspectives

Biodegradation and biotransformation of polycyclic non-steroidal anti-inflammatory drugs

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