Abstract
Although biotransformation is generally considered to be the main process by which to remove pharmaceuticals, both in sewage treatment plants and in aquatic environments, quantitative information on specific compounds is scarce. In this study, the transformations of diclofenac (DCF), naproxen (NPX), and bisoprolol (BSP) were studied under aerobic and anaerobic conditions using inocula taken from activated and digested sludge processes, respectively. Whereas concentration decays were monitored by LC–tandem mass spectrometry, oxygen consumption and methane production were used for the evaluation of the performance of overall conditions. DCF was recalcitrant against both aerobic and anaerobic biotransformation. More than one third of the BSP disappeared under aerobic conditions, whereas only 14% was anaerobically biotransformed in 161 days. Under aerobic conditions, complete removal of NPX was evident within 14 days, but anaerobic transformation was also efficient. Formation of 6-O-desmethylnaproxen, a previously reported aerobic metabolite, was also detected under anaerobic conditions and persisted for 161 days.
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References
Alexander M (1997) Microbial communities and interactions: a prelude. In: Hurst CJ, Knudsen GR, McInerney MJ, Stetzenbach LD, Walter MV (eds) Manual of environmental microbiology. ASM Press, Washington, DC, pp 707–708
Carballa M, Omil F, Ternes T, Lema JM (2007) Fate of pharmaceutical and personal care products (PPCPs) during anaerobic digestion of sewage sludge. Water Res 41:2139–2150
Falany CN, Ström P, Swedmark S (2005) Sulphation of o-desmethylnaproxen and related compounds by human cytosolic sulfotransferases. Br J Clin Pharmacol 60:632–640
Giger W, Brunner PH, Schaffner C (1984) 4-Nonylphenol in sewage sludge: accumulation of toxic metabolites from nonionic surfactants. Science 225:623–625
Gröning J, Held C, Garten C, Claussznitzer U, Kaschabek SR, Schlömann M (2007) Transformation of diclofenac by the indigenous microflora of river sediments and identification of a major intermediate. Chemosphere 69:509–516
Gros M, Petrovic M, Barcelo D (2007) Wastewater treatment plants as a pathway for aquatic contamination by pharmaceuticals in the Ebro River Basin (northeast Spain). Environ Toxicol Chem 26:1553–1562
Heberer T (2002) Occurrence, fate, and removal of pharmaceutical residues in the aquatic environment: a review of recent research data. Toxicol Lett 131:5–17
Hoeger B, Köllner B, Dietrich DR, Hitzfeld B (2005) Water-borne diclofenac affects kidney and gill integrity and selected immune parameters in brown trout (Salmo trutta f. fario). Aquat Toxicol 75:53–64
International Organisation for Standardisation (1995) Water quality—Evaluation of the “ultimate” anaerobic biodegradability of organic compounds in digested sludge: Method by measurement of the biogas production. ISO 11734. ISO Geneva, Switzerland
Joss A, Andersen H, Ternes T, Richle P, Siegrist H (2004) Removal of estrogens in municipal wastewater treatment under aerobic and anaerobic conditions: consequences for plant optimization. Environ Sci Technol 38:3047–3055
Joss A, Zabczynski S, Göbel A, Hoffmann B, Löffler D, McArdell CS, Ternes TA et al (2006) Biological degradation of pharmaceuticals in municipal wastewater treatment: proposing a classification scheme. Water Res 40:1686–1696
Kolpin DW, Furlong ET, Meyer MT, Thurman EM, Zaugg SD, Barber LB et al (2002) Pharmaceuticals, hormones and other organic wastewater contaminants in U.S. streams, 1999–2000: a national reconnaissance. Environ Sci Technol 36:1202–1211
Kosjek T, Žigon D, Kralj B, Heath E (2008) The use of quadrupole-time-of-flight mass spectrometer for the elucidation of diclofenac biotransformation products in wastewater. J Chromatogr 1215:57–63
Lambert W, Sommer U (2007) Limnoecology, 2nd edn. Oxford University Press, Oxford, UK
Larsson JDG, de Pedro C, Paxeus N (2007) Effluent from drug manufactures contains extremely high levels of pharmaceuticals. J Hazard Mater 148:751–755
Metcalfe CD, Miao X, Koenig BG, Struger J (2003) Distribution of acidic and neutral drugs in surface waters near sewage treatment plants in the lower Great Lakes, Canada. Environ Toxicol Chem 22:2881–2889
Oaks JL, Gilbert M, Virani MZ, Watson RT, Meteyer CU, Rideout BA et al (2004) Diclofenac residues as the cause of vulture population decline in Pakistan. Nature 427:630–633
Organisation for Economic Co-Operation and Development (1992) OECD guideline for testing of chemicals. 301F Ready biodegradability: manometric respirometry test. OECD, Paris, France
Quintana JB, Weiss S, Reemtsma T (2005) Pathways and metabolites of microbial degradation of selected acidic pharmaceutical and their occurrence in municipal wastewater treated by a membrane bioreactor. Water Res 39:2654–2664
Ramil M, El Aref T, Fink G, Scheurer M, Ternes TA (2010) Fate of beta blockers in aquatic-sediment systems: sorption and biotransformation. Environ Sci Technol 44:962–970
Richardson ML, Bowron JM (1985) The fate of pharmaceutical chemicals in the aquatic environment. J Pharm Pharmacol 37:1–12
Rogers H (1996) Sources, behaviour and fate of organic contaminants during sewage treatment and in sewage sludges. Sci Total Environ 185:3–26
Schwartz H, Licht R-E, Radunz H-E (1993) Microbial metabolism of the beta-adrenoreceptor antagonist bisoprolol. Appl Microbiol Biotechnol 40:382–385
Ternes TA (1998) Occurrence of drugs in German sewage treatment plants and rivers. Water Res 32:3245–3260
Tran NH, Urase T, Kusakabe O (2009) The characteristics of enriched nitrifier culture in the degradation of selected pharmaceutically active compounds. J Hazard Mater 171:1051–1057
Triebskorn R, Casper H, Heyd A, Eikemper R, Köhler H-R, Schwaiger J (2004) Toxic effects of the non-steroidal anti-inflammatory drug diclofenac. Part II. Cytological effects in liver, kidney, gills and intestine of rainbow trout (Oncorhynchus mykiss). Aquat Toxicol 68:151–166
Urase T, Kikuta T (2005) Separate estimation of adsorption and degradation of pharmaceutical substances and estrogens in the activated sludge process. Water Res 39:1289–1300
Vieno NM, Tuhkanen T, Kronberg L (2005) Seasonal variations in the occurrence of pharmaceuticals in effluents from a sewage treatment plant and in the recipient water. Environ Sci Technol 29:8220–8226
Walter MV, Crawford RL (1997) Biotransformation and biodegradation. In: Hurst CJ, Knudsen GR, McInerney MJ, Stetzenbach LD, Walter MV (eds) Manual of environmental microbiology. ASM Press, Washington, DC, pp 707–708
Wick A, Fink G, Joss A, Siegrist H, Ternes T (2009) Fate of beta blockers and psycho-active drugs in conventional wastewater treatment. Water Res 43:1060–1074
Wilson BH, Smith GB, Rees JF (1986) Biotransformations of selected alkylbenzenes and halogenated aliphatic hydrocarbons in methanogenic aquifer material: a microcosm study. Environ Sci Technol 20:997–1002
Yu JT, Bouwer EJ, Coelhan M (2006) Occurrence and biodegradability studies of selected pharmaceuticals and personal care products in sewage effluent. Agric Water Manage 86:72–80
Acknowledgements
The study was supported by grants from the Academy of Finland (No 109823) and the Finnish graduate school in Environmental Science and Technology. The authors thank Mervi Koistinen for technical assistance, the research group of Jukka Rintala for analytic tools to measure methane, and the research group of Leif Kronberg from Åbo Akademi University, Finland, for the synthesis of 6-O-desmethylnaproxen.
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Lahti, M., Oikari, A. Microbial Transformation of Pharmaceuticals Naproxen, Bisoprolol, and Diclofenac in Aerobic and Anaerobic Environments. Arch Environ Contam Toxicol 61, 202–210 (2011). https://doi.org/10.1007/s00244-010-9622-2
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DOI: https://doi.org/10.1007/s00244-010-9622-2