Degradation mechanisms of oxytetracycline in the environment

doi:10.1016/S2095-3119(18)62121-5

摘要/Abstract

Abstract:

Over the past few decades, the usage of oxytetracycline (OTC), a kind of antibiotic, has increased with the development of aquaculture and livestock breeding. However, about 30–90% of the applied antibiotics are excreted as the parent compounds into the environment, especially with the application of animal manure to agricultural fields. This large influx of antibiotics may lead to the destruction of the natural microbial ecological community and pose great threats to human beings through the food chain. Therefore, the fate and toxicity of OTC in the environment are issues of great concern. Degradation of OTC, including the non-biodegradation and biodegradation, and the biological toxicity of its degradation products or metabolites, are reviewed in this paper. The non-biodegradation pathways include hydroxylation, quinonization, demethylation, decarbonylation, dehydration and secondary alcohol oxidation. Light (particularly UV light), pH and oxidizing substances play important roles in non-biodegradation. Biodegradation products include 4-epi-OTC (EOTC), 2-acetyl-2-decarboxy-amido-OTC (ADOTC), α-apo-OTC and β-apo-OTC. EOTC is an epimer and identied except for the configuration of the C4 dimethylamino group of OTC. Temperature and pH are the main factors affecting biodegradation pathways of OTC. In addition, this review discusses concerns over the biological toxicity of OTC degradation products.

Key words:

oxytetracycline , degradation pathways , biotoxicity , degradation products

. [J]. Journal of Integrative Agriculture, 2019, 18(9): 1953-1960.

LI Zhao-jun, QI Wei-ning, FENG Yao, LIU Yuan-wang, Ebrahim Shehata, LONG Jian . Degradation mechanisms of oxytetracycline in the environment[J]. Journal of Integrative Agriculture, 2019, 18(9): 1953-1960.

参考文献

Alcock R E, Sweetman A, Jones K C. 1999. Assessment of organic contaminant fate in waste water treatment plants. Selected compounds and physicochemical properties. Chemosphere, 38, 2247–2262.
Arabpour N, Ejhieh A N. 2016. Photodegradation of cotrimaxazole by clinoptilolite-supported nickel oxide. Process Safety and Environmental Protection, 102, 431–440.
Arikan O A, Sikora L J, Mulbry W, Khan S U, Rice C, Foster G D. 2006. The fate and effect of oxytetracycline during the anaerobic digestion of manure from therapeutically treated calves. Process Biochemistry, 41, 1637–1643.
Aytekin C, Eoin C, Halil H. 2018. Degradation of oxytetracycline under autotrophic nitrifying conditions in a membrane aerated biofilm reactor and community fingerprinting. Journal of Hazardous Materials, 356, 26–33.
Bautitz I R, Nogueira R F P. 2007. Degradation of tetracycline by photo-Fenton process - Solar irradiation and matrix effects. Journal of Photochemistry & Photobiology (A: Chemistry), 187, 33–39.
Belkacem S, Bouafia S, Chabani M. 2017. Study of oxytetracycline degradation by means ofanodic oxidation process using platinized titanium (Ti/Pt) anode and modeling by artificial neuralnetworks. Process Safety and Environmental Protection, 111, 170–179.
Bound J P, Voulvoulis N. 2006. Predicted and measured concentrations for selected pharmaceuticals in UK rivers: implications for risk assessment. Water Research, 40, 2885–2892.
Brambilla G, Patrizii M, Filippis S D, Bonazzi G, Mantovi P, Barchi D, Migliore L. 2007. Oxytetracycline as environmental contaminant in arable lands. Analytical Chimica Acta, 586, 326–329.
Chen G X, He W W, Wang Y, Zou Y D, Liang J B, Liao X D, Wu Y B. 2014. Effect of different oxytetracycline addition methods on its degradation behavior in soil. Science of the Total Environment, 479–480, 241–246.
Chen Y, Xi X, Yu G, Cao Q, Wang B, Vince F, Hong Y. 2015. Pharmaceutical compounds in aquatic environment in China: Locally screening and environmental risk assessment. Frontiers of Environmental Science & Engineering, 9, 394–401.
Cheng D M, Liu X H, Zhao S J, Cui B S, Bai J H, Li Z J. 2017. Influence of the natural colloids on the multi-phase distributions of antibiotics in the surface water from the largest lake in North China. Science of the Total Environment, 578, 649–659.
Cheng D M, Xie Y J, Yu Y J, Liu X H, Zhao S G, Cui B S, Bai J H. 2016. Occurrence and partitioning of antibiotics in the water column and bottom sediments from the intertidal zone in the Bohai Bay, China. Wetlands, 36, S167–S179.
Doi A M, Stoskopf M K. 2000. The kinetics of OTC degradation in deionized water under varying temperature, pH, light, substrate, and organic matter. Journal of Aquatic Animal Health, 12, 246–253.
Fleming A. 2001. On the antibacterial action of cultures of a penicillium, with special reference to their use in the isolation of B. influenzae. Bulletin of the World Health Organization, 79, 780–790.
Galli E, Brancaleoni E, Mario F D, Donati E, Frattoni M, Polcaro C M, Rapanà P. 2008. Mycelium growth and degradation of creosote-treated wood by basydiomycetes. Chemosphere, 72, 1069–1072.
Giokas D L, Vlessidis A G. 2007. Application of a novel chemometric approach to the determination of aqueous photolysis rates of organic compounds in natural waters. Talanta, 71, 288–295.
Halling-Sørensen B, Sengeløv G, Tjørnelund J. 2002. Toxicity of tetracyclines and tetracycline degradation products to environmentally relevant bacteria including selected tetracycline resistant bacteria. Archives of Environmental Contamination and Toxicology, 42, 263–271.
Han H X, Xiao H L, Lu Z M. 2016. Short-term toxicity assessments of an antibiotic metabolite in Wistar rats and its metabonomics analysis by ultra-high performance liquid chromatography coupled to quadrupole time-of-flight mass spectrometry. Toxicology and Applied Pharmacology, 293, 1–9.
He X, Mezyk S P, Michael L, Fatta-Kassinos D, Dionysiou D D. 2014. Degradation kinetics and mechanism of β-lactam antibiotics by the activation of H2O2 and Na2S2O8 under UV-254 nm irradiation. Journal of Hazard Mater, 279, 375–383.
He X M, Pelaez M, Westrick J A, O’Shea K E, Hiskia A, Triantis T, Kaloudis T, Stefan M I, Cruz A A, Dionysiou D D. 2012. Efficient removal of microcystin-LR by UV-C/H2O2 in synthetic and natural water samples. Water Research, 46, 1501–1510.
Ho Y B, Zakaria M P, Latif P A, Saari N. 2013. Degradation of veterinary antibiotics and hormone during broiler manure composting. Bioresour Technology, 131, 476–484.
Jacobsen A M, Halling-Sørensen B, Ingerslev F, Hansen S H. 2004. Simultaneous extraction of tetracycline, macrolide and sulfonamide antibiotics from agricultural soils using pressurised liquid extraction, followed by solid-phase extraction and liquid chromatographyetandem mass spectrometry. Journal of Chromatography (A), 1038, 157–170.
Khan M H, Bae H, Jung J Y. 2010. Tetracycline degradation by ozonation in the aqueous phase: Proposed degradation intermediates and pathway. Journal of Hazardous Materials, 181, 659–665.
Kwon J. 2011. Mobility of veterinary drugs in soil with application of manure compost. Bulletin of Environmental Contamination and Toxicology, 87, 40–44.
Kümmerer K. 2009. Antibiotics in the aquatic environment - A review - Part I. Chemosphere, 75, 417–434.
Liu L L, Wu W, Zhang J Y, Lv P, Xu L, Yan Y C. 2018. Progress of research on the toxicology of antibiotic pollution in aquatic organisms. Acta Ecologica Sinica, 38, 36–41.
Liu Y, He X, Duan X. 2016. Significant role of UV and carbonate radical on the degradation of oxytetracycline in UV-AOPs: Kinetics and mechanism. Water Research, 95, 195–204.
Liu Y, He X, Duan X, Fu Y, Dionysiou D D. 2015. Photochemical degradation of oxytetracycline: Influence of pH and role of carbonate radical. Chemical Engineering Journal, 276, 113–121.
Liu Y W, Feng Y, Cheng D M, Xue J M, Wakelin S A, Hu H Y, Li Z J. 2017. Gentamicin degradation and changes in fungal diversity and physicochemical properties during composting of gentamicin production residue. Bioresource Technology, 244, 905–912.
Liu Y W, Feng Y, Cheng D M, Xue J M, Wakelin S, Li Z J. 2018. Dynamics of bacterial composition and the fate of antibiotic resistance genes and mobile genetic elements during the co-composting with gentamicin fermentation residue and lovastatin fermentation residue. Bioresource Technology, 261, 249–256.
Loftin K A, Adams C D, Meyer M T, Surampalli R. 2008. Effects of ionic strength, temperature, and pH on degradation of selected antibiotics. Journal of Environmental Quality, 37, 378–386.
Magdaleno A, Carusso S, Moretton J. 2017. Toxicity and genotoxicity of three antimicrobials commonly used in veterinary medicine. Bulletin of Environmental Contamination and Toxicology, 99, 315–320.
Martínez-Carballo E, González-Barreiro C, Scharf S, Gans O. 2007. Environmental monitoring study of selected veterinary antibiotics in animal manure and soils in Austria. Environmental Pollution, 148, 570–579.
Migliore L, Fiori M, Spadoni A, Galli E. 2012. Biodegradation of oxytetracycline by Pleurotus ostreatus mycelium: a mycoremediation technique. Journal of Hazardous Materials, 215–216, 227–232.
Pham V A, Kim D G, Ko S O. 2018. Cu@Fe3O4 core-shell nanoparticle-catalyzed oxidative degradation of the antibiotic oxytetracycline in pre-treated landfill leachate. Chemosphere, 191, 639–650.
Pouliquen H, Delepee R, Larhantec-Verdier M, Morvan M L, Bris H L. 2007. Comparative hydrolysis and photolysis of four antibacterial agents (oxytetracycline, oxolinic acid, flumequine and florfenicol) in deionised water, freshwater and seawater under abiotic conditions. Aquaculture, 262, 23–28.
Ramaswamy J, Prasher S O, Patel R M, Hussain S A, Barrington S F. 2010. The effect of compostingon the degradation of a veterinary pharmaceutical. Bioresource Technology, 101, 2294–2299.
Shemer H, Kunukcu Y K, Linden K G. 2006. Degradation of the pharmaceutical Metronidazole via UV, Fenton and photo-Fenton processes. Chemosphere, 63, 269–276.
Shen D S, Tao X Q, Shen L J, Wang M Z. 2014. Residues of veterinary antibiotics in pig feeds and manures in Zhejiang Province. Advanced Materials Research, 1010–1012, 301–304.
Shen Y, Wei Y, Zheng J, Fang Y, Chen L. 2009. Biodegradation of tetracycline antibiotics residues in swine manure. The Chinese Journal of Process Engineering, 9, 962–968. (in Chinese)
Shi J, Liao X D, Wu Y B, Liang J B. 2011. Effect of antibiotics onmethane arising from anaerobic digestion of pig manure. Animal Feed Science & Technology, 166, 457–463.
Sturini M, Speltini A, Maraschi F, Pretali L, Profumo A, Fasani E, Albini A, Migliavacca R, Nucleo E. 2012. Photodegradation of fluoroquinolones in surface water and antimicrobial activity of the photoproducts. Water Research, 46, 5575–5582.
Tian S F, Zhang H Q. 2011. Degradation of tetracycline in aqueous media by ozonation in an internal loop-lift reactor. Journal of Hazardous Materials, 192, 35–43.
Varavithya W, Chulajata R, Ayudthya P S, Preeyasombat C. 1971. Fanconi syndrome caused by degraded tetracycline. Journal of the Medical Association of Thailand, 54, 62–67.
Wang Q Q, Yates S R. 2008. Laboratory study of oxytetracycline degradation kinetics in animal manure and soil. Journal of Agricultural and Food Chemistry, 56, 1683–1688.
Wen X, Jia Y, Li J. 2010. Enzymatic degradation of tetracycline and oxytetracycline by crude manganese peroxidase prepared from Phanerochaete chrysosporium. Journal of Hazardous Materials, 177, 924–928.
Winckler C, Grafe A. 2001. Use of veterinary drugs in intensive animal production: Evidence for persistence of tetracycline in pig slurry. Journal of Soils and Sedments, 1, 66–70.
Wu D, Huang Z, Yang K, Graham D, Xie B. 2015. Relationships between antibiotics and antibiotic resistance gene levels in municipal solid waste leachates in Shanghai, China. Environment Science & Technology, 49, 4122–4128.
Wu J G, Jiang Y X, Zha L Y, Ye Z M, Zhou Z F, Ye J F, Zhou H W. 2010. Tetracycline degradation by ozonation, and evaluation of biodegradability and toxicity of ozonation byproducts. Canadian Journal of Civil Engineering, 37, 1485–1491.
Wu X F, Wei Y S, Zheng J X, Zhao X, Zhong W K. 2011. The behavior of tetracyclines and their degradation products during swine manure composting. Bioresource Technology, 102, 5924–5931.
Xu Y, Guo C, Luo Y, Lv J, Zhang Y, Lin H, Wang L, Xu J. 2016. Occurrence and distribution of antibiotics, antibiotic resistance genes in the urban rivers in Beijing, China. Environmental Pollution, 213, 833–840.
Xuan R, Arisi L, Wang Q, Yates S R, Biswas K C. 2009. Hydrolysis and photolysis of oxytetracycline in aqueous solution. Journal of Environmental Science and Health (Part B: Pesticides Food Contaminants and Agricultural Wastes), 45, 73–81.
Zhou L J, Ying G G, Liu S, Zhang R Q, Lai H J, Chen Z F, Pan C G. 2013. Excretion masses and environmental occurrence of antibiotics in typical swine and dairy cattle farms in China. Science of the Total Environment, 444, 183–195.