Biodegradation of the analgesic naproxen by Trametes versicolor and identification of intermediates using HPLC-DAD-MS and NMR

Marco‐Urrea, Ernest; Pérez‐Trujillo, Míriam; Blánquez, Paqui; Vicent, Teresa; Caminal, Glòria

doi:10.1016/j.biortech.2009.11.019

Cited by 173 publications

(83 citation statements)

References 38 publications

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“…Noteworthy Trametes hirsuta halved the initial amount of 9 out to 17 pharmaceuticals set at realistic concentrations (20-500 ng/l) (Haroune et al 2014). The removal of naproxen and diclofenac by T. versicolor was almost complete at 10 mg/l and at 45-55 µg/l (Marco- Urrea et al 2010a, Marco-Urrea et al 2010b). …”

Section: Urrea Et Al 2009)mentioning

confidence: 98%

“…The development of this technology could take into consideration also the coimmobilization of different enzymes typology e.g. as laccases and cytochrome P450 which played both an active role in the conversion of diclofenac and naproxen by T. versicolor (Marco-Urrea et al 2010a, Marco-Urrea et al 2010b). …”

Section: Fungal Laccasesmentioning

confidence: 99%

“…Luminescent bacteria V. fischeri (UNI EN ISO 11348-3) was used for the conversion of NP by 4 fungi (Soares et al 2006), BPA and TCS by laccases from T. versicolor (Kim and Nicell 2006c), sulfonamide antibiotics by laccases from Perenniporia sp. (Weng et al 2013), naproxen (Marco-Urrea et al 2010b) and several pharmaceuticals and recognized EDCs by laccases from T. versicolor (Cruz-Moratò et al 2014). …”

Section: Toxicity Evaluationmentioning

confidence: 99%

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Section: Urrea Et Al 2009)mentioning

confidence: 98%

Section: Fungal Laccasesmentioning

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Section: Toxicity Evaluationmentioning

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“…While the transformation mechanisms of non-steroidal antiinflammatory drugs in the human body and in other animals have been extensively studied, the degradation of these drugs by bacteria has been seldom investigated and remains largely unknown (Quintana et al, 2005;Marco-Urrea et al, 2010;Wojcieszyńska et al, 2014). It is suggested that the transformation of naproxen by Trametes versicolor or activated sludge may occur by 2-(6-hydroxynaphthalen-2-yl)propanoic acid and 1-(6-metho xynaphthalen-2-yl)ethanone formation (Quintana et al, 2005;Marco-Urrea et al, 2010;Lahti and Oikari, 2011). Marco-Urrea et al (2010) suggested participation of laccase and cytochrome P-450 system in biotransformation of this drug in fungi.…”

Section: Introductionmentioning

confidence: 99%

“…It is suggested that the transformation of naproxen by Trametes versicolor or activated sludge may occur by 2-(6-hydroxynaphthalen-2-yl)propanoic acid and 1-(6-metho xynaphthalen-2-yl)ethanone formation (Quintana et al, 2005;Marco-Urrea et al, 2010;Lahti and Oikari, 2011). Marco-Urrea et al (2010) suggested participation of laccase and cytochrome P-450 system in biotransformation of this drug in fungi. Among bacteria, only Stenotrophomonas maltophilia KB2 is known to be able to cometabolically degrade naproxen (Wojcieszyńska et al, 2014).…”

Section: Introductionmentioning

confidence: 99%

Enzymes Involved in Naproxen Degradation by Planococcus sp. S5

Wojcieszyńska

Domaradzka

Hupert-Kocurek

2016

Polish Journal of Microbiology

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A b s t r a c tNaproxen is a one of the most popular non-steroidal anti-inflammatory drugs (NSAIDs) entering the environment as a result of high consumption. For this reason, there is an emerging need to recognize mechanisms of its degradation and enzymes engaged in this process. Planococcus sp. S5 is a gram positive strain able to degrade naproxen in monosubstrate culture (27%). However, naproxen is not a sufficient growth substrate for this strain. In the presence of benzoate, 4-hydroxybenzoic acid, 3,4-dihydroxybenzoic acid or vanillic acid as growth substrates, the degradation of 21.5%, 71.71%, 14.75% and 8.16% of naproxen was observed respectively. It was shown that the activity of monooxygenase, hydroxyquinol 1,2-dioxygenase, protocatechuate 3,4-dioxygenase and protocatechuate 4,5-dioxyegnase in strain S5 was induced after growth of the strain with naproxen and 4-hydroxybenzoate. Moreover, in the presence of naproxen activity of gentisate 1,2-dioxygenase, enzyme engaged in 4-hydroxybenzoate metabolism, was completely inhibited. The obtained results suggest that monooxygenase and hydroxyquinol 1,2-dioxygenase are the main enzymes in naproxen degradation by Planococcus sp. S5. 178acid produced by Prunus domestica, Melissa officinalis or Vitis vinifera or vanillic acid identified in Juglans regia or Chenopodium murales (Ghareib et al., 2010;Kakkar and Bais, 2014). The objective of our study is to examine the ability of Planococcus sp. S5 to degrade naproxen in either mono-or disubstrate cultures with plant aromatic compounds as growth substrates. Plano coccus sp. S5 was chosen for this study since it degrades salicylate (Łabużek et al., 2003), which is not only the intermediate of naphthalene degradation and mimetic of naproxen, but also belongs to non-steroidal antiinflammatory drugs. Additionally, the aim of this study is to identify enzymes engaged in naproxen degradation by Planococcus sp. S5 in cometabolic conditions. Experimental Materials and MethodsMedia and culture conditions. Planococcus sp. S5 was routinely cultivated in BBL nutrient broth at 30°C and 130 rpm for 24 hours. Then 6 mg/l naproxen was added to the culture. After 48 hours, cells were harvested by centrifugation (5.000 × g at 4°C for 15 min), washed with fresh sterile medium and used as inoculum. Degradation of naproxen in a monosubstrate, as well as cometabolic systems, was performed in 500 ml Erlenmeyer flasks containing 250 ml of the mineral salts medium (Greń et al., 2010) inoculated with cells to a final optical density of about 1.5 and 0.5 at λ = 600 nm (OD600) for the monosubstrate and cometabolic systems, respectively. For degradation experiments two control cultures were prepared. The uninoculated control (I) consisted of 250 ml of sterile mineral salts medium, while the heatkilled control (II) consisted of 250 ml of autoclaved culture prepared under conditions identical to those of the experimental cultures. Naproxen was added to each flask to obtain a final concentration of 6 mg/l, and all cultures were incubated with shakin...

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Applications of NMR Techniques for the Identification and Structure Elucidation of Emerging Organic and Other Xenobiotic Organic Contaminants

Preiß

Godejohann

2014

Transformation Products of Emerging Contaminants in the Environment

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Biodegradation of the analgesic naproxen by Trametes versicolor and identification of intermediates using HPLC-DAD-MS and NMR

Cited by 173 publications

References 38 publications

Fungal Bioremediation of Emerging Micropollutants in Municipal Wastewaters

Fungal Bioremediation of Emerging Micropollutants in Municipal Wastewaters

Enzymes Involved in Naproxen Degradation by Planococcus sp. S5

Applications of NMR Techniques for the Identification and Structure Elucidation of Emerging Organic and Other Xenobiotic Organic Contaminants

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