Endocrine Disrupting Compounds in Water Environment: Comparison
View Latest Version
Please note this is a comparison between Version 3 by Dean Liu and Version 2 by Dean Liu.

Endocrine disrupting compounds (EDCs) are a particularly dangerous group because they have estrogenic activity. Among EDCs, the alkylphenols commonly used in households deserve attention, from where they go to sewage treatment plants, and then to water reservoirs.

  • bioremediation
  • endocrine disrupting compounds
  • laccase

1. Introduction

Environmental pollution has become a major challenge in recent years due to increasing population, urbanization, and industrialization [1]. The priority is to find the sources of EDCs and the routes by which they enter the aquatic environment.
EDC has been detected in a variety of fresh, brackish, and marine ecosystems. Due to their physical and chemical properties, EDCs can bioaccumulate, biomagnify, are persistent, and are very toxic to aquatic organisms, both for plants and animals [2].
These compounds are released into the environment from a variety of sources, primarily municipal and industrial waste, agricultural practices, animal waste, and sewage treatment plants (STP) [3]. Most of the packaging for food, cosmetic products, solvents, preservatives, and pesticides is also made of EDC-containing materials [2][4][5].
Long-term use of EDC, regardless of the concentration level, may accumulate in animals and be partially released into the environment through animal feces. In fish and the largest consumers of the food web, the rate of bioaccumulation is higher because most EDCs are lipophilic and concentrated in the fat of the consuming organisms [6]. Therefore, these substances will penetrate the food chain and ecosystems, potentially adversely affecting human health.
In agriculture, non-metabolized and non-degradable compounds in animal fertilizers still have active metabolites, reducing the quality of surface and groundwater and significantly affecting aquatic life. In water, EDCs undergo biodegradation and chemical and photochemical degradation, dilution, and sorption to sediments, which partially leads to their elimination from aquatic ecosystems [2][7][8][9].

2. Nonylphenol

The presence of nonylphenol in the environment is clearly correlated with anthropogenic activities such as sewage treatment, storage, and recycling of sewage sludge. NPEOs are used as non-ionic surfactants in industry (cellulose and paper, textiles, agriculture, metals, plastics, petroleum refining), in households in the form of detergents, solubilizers, and personal care products in non-EU countries [10][11]. Nonylphenol is a xenobiotic compound used in the production of antioxidants, additives to lubricating oils and in the production of ethoxylated surfactants nonylphenol, which is its main use (65%) [12]. As surfactants, NPs are used in cleaning agents, so their primary source in the environment are discharges of wastewater from industrial and municipal wastewater treatment plants (WWTPs), as well as land enriched with solid sewage or manure, runoff from pesticides and fertilizers on agricultural fields, and fodder livestock. Due to their cheapness, NPEO surfactants are used in various areas, for example in agricultural pesticides where surfactant is added to control the properties of pesticides [13][14]. Inadequately treated domestic sewage causes high concentrations of NP in the aquatic environment. The levels of NP depended on the size of NP discharges into the river, temperature, flow velocity, biodegradation, etc. About 60% of NP and its derivatives produced in the world ends up in water supply [15][16][17]. In addition, the presence of NP is observed in polyvinyl chloride (PVC), which can contaminate water passing through PVC plumbing [18]. Technical NP is the major form of NP that is released into the environment. Technical nonylphenol consists of a mixture of more than one hundred isomers that have an alkyl moiety attached at various positions on the phenolic ring, with para-substituted NP (4-NP). However, in the environment, the proportions of isomers may be different [13][19][20]. Due to its high hydrophobicity, resistance to biodegradation and low solubility, NP tends to accumulate in various environmental matrices [21]. NP can evaporate into the atmosphere from wastewater discharges, wastewater treatment plant (liquids and sludge) or heavily contaminated surface waters. NP binds to the aerosols generated by the wastewater treatment plant, leading to a reduction in air quality in the vicinity of STW. From the atmosphere, NP may re-enter aquatic and terrestrial ecosystems with rain and snowfall [12]. The concentration of nonylphenol in the surface layers of natural waters may decrease due to photolysis induced by sunlight [7][22]. Biodegradation of NPs is difficult due to physicochemical properties such as low solubility and high hydrophobicity. NP accumulates in environmental compartments that are characterized by a high content of organic substances, usually sewage sludge and river sediments. NP occurs in river waters in concentrations up to 4.1 μg/L and 1 mg/kg in sediments [15][16][23]. The concentration of NP in the water and sediments are shown in Table 1.
Table 1. The Bisphenol A (BPA) and nonylphenol (NP) concentrations in aquatic environments.
Environment BPA NP Location References
Surface water nd–376.6 117–865 China,

Pearl River Delta		 [24][25]
15.80–110.38 nd–104.02 China,

Honghu Lake		 [26]
16.3–30.1 - Poland, Vistula river [27]
0.71–47.40 - Philippines,

Laguna Lake		 [28]
Groundwater nd–35.54 5,6 China [29][30]
1–629 - Poland [27]
Wastewater treatment plants IW nd–5927.5 nd–9560 Poland [27]
EW nd–190 nd–9560
IW 234.6–1527.1 519.6–4183.4 China [31]
EW 3.1–623.6 13.4–471.6
Seawater 10.6–52.3 22–201 Greece,

Thermaikos Gulf,

Northern Aegean Sea		 [32]
240 730 Japan,

Tokyo Bay coastal area		 [33]
Sediment W 7.02–13.95 - China,

Erhai Lake		 [34]
S 11.09–63.46 -
W - 75.4 Germany,

Luppe River		 [35]
S - 22,342.6
W nd–37,000 - Indonesia,

Mahakam River		 [36]
S nd–952.6 -
W <1.3–5.2 nd New Zealand,

Lyttelton Harbour		 [37]
S <0.4–9.9 nd
W 5.0–277.9 4.0–1721 Poland,

Gulf of Gdańsk

(southern Baltic Sea)		 [38]
S 2.64–60.20 0.08–1001
Drinking water 6–53 - Poland [27]
2.6–6.2 1.7–3.9 Serbia, rural area [39]
2.5–35.6 1.2–7.9 Serbia, urban area [39]
nd–not detected; IW-influent; EW–effluent; W–water; S-sediment.
The presence of NP in surface waters is correlated with anthropogenic activity and wastewater discharge from STW, industrial plants, municipal wastewater treatment plants, and rainwater discharges [12][40]. NP concentrations in rivers are subject to seasonal fluctuations with higher concentrations in summer due to increased microbial activity at higher temperatures leading to increased degradation of ethoxylates nonylphenol [41][42]. Other factors such as river flow rate, sedimentation rate, and particle size also influence the rate of degradation. NP occurs in the aquatic environment in quite different concentrations in surface waters, from several dozen ng/L to several dozen mg/L [43]. Groundwater is of particular interest as it accounts for about twenty percent of the world’s freshwater supply and is extremely susceptible to contamination by various pollutants as a result of urban activities. NP concentrations in groundwater were incredibly low [44][45][46]. The microbial decomposition of NP in aquifers is limited due to the low temperature conditions prevailing there: low temperature, low C, and low O2 content). The processes controlling the entry of pollutants into groundwater are sorption and biodegradation [12][15]. Ethoxylates nonylphenol (NPEO) ends up in significant amounts in wastewater treatment plants, where they biodegrade into several by-products, including nonylphenol, which is more resistant than the parent compound [12][47]. NP is the major degradation product, does not undergo further transformation, and is highly adsorbed in the sludge; therefore, it is often found in higher concentrations in wastewater than in tributaries [12][47][48]. In most cases, it is the strong sorption of pollutants, and not the microbiological activity, which limits the rate of biodegradation [49]. On the rate of biodegradation NPEO, the main sources of NP in WWTPs, is affected by many factors e.g., temperature, NP isomer present in the environment, oxygen availability, pH and additives of yeast extracts, surfactants, aluminum sulphate, acetate, pyruvate, lactate, manganese dioxide, iron chloride, sodium chloride, hydrogen peroxide, heavy metals, and phthalic acid esters [50][51][52]. Conventional physicochemical wastewater treatment methods have not been shown to be effective in removing endocrine disruptors such as NPs due to their low molecular weight [1][53]. Novel purification techniques, including advanced oxidation methods, UV [54], adsorption (powdered activated carbon (PAC), and granular activated carbon (GAC)), ion exchange and membrane filtration (ceramics, polymers, and zeolites) are still under analysis [55][56]. One of the other methods of NP removal is to use cells and enzymes. Tanghe et al. in 1999 first described the Sphingomonas strain that degraded NP [57]. Since then, microorganisms involved in the biodegradation of NPs in the aquatic environment have been discovered (Sphingobium, Pseudomonas, Pseudoxanthomonas, Thauera, Novosphingonium, Bacillus, Stenotrophomonas, Clostridium, Arthrobacter, Acidurvorax, Rhizobium, Corynebacterium, Traynebacterium, Rhodococcus, Candida, Phanerochaete, Bjerkandera, Mucor, Fusarium and Metarhizium) [13][52][58][59][60][61]. NP-degrading microorganisms were isolated from municipal sewage treatment plants from sludge, sewage sludge and activated sludge under aerobic and anaerobic conditions. Appropriate pH value, temperature, and the level of aeration of sewage sludge contribute to the increase of microbiological activity, and thus increase the degradation of NP. Anaerobic degradation of NP has only recently been shown. Half-lives of anaerobic degradation ranged from 23.9 to 69.3 days. The rate of anaerobic degradation of NP was enhanced by increasing the temperature and adding yeast extract or surfactants [15][43][62]. Bacterial strains are effective in improving NP biodegradation and short-chain fatty acid accumulation. The species Propionibacterium, Paludibacter, Proteiniphilum, Guggenheimella, Lactobacillus, Anaerovorax and Proteiniborus correlated with the short-chain fatty acids synthesized as a result of NP degradation [59][63]. Some bacteria and fungi produce laccase, a multifunctional enzyme. Laccases are well-known enzymes that have found application in bioremediation, both as free and immobilized enzymes. Thanks to their broad range substrate specificity, laccases are able to remove xenobiotics, including EDCs. Therefore, the white rot fungi (WRF) are a promising tool in the above-mentioned elimination of EDCs during wastewater treatment processes [64]. The advantage of fungi over bacteria in lignin mineralization results from the production and secretion of laccase-non-specific enzyme outside the cell, which gives fungi access to non-polar and insoluble substances, operation over a wide range of temperatures and pH values, and the developing fungal hyphae also make it possible to reach contaminants inaccessible to bacteria [64][65][66]. The laccase from WRF like Pleurotus eryngii, Trametes versicolor or Phanerochaete chrysosporium can adhesion to alkylphenols, because these compounds have functional groups such as amino, hydroxyl, or alkyl groups in its chemical structure, acting as electron donors for oxygenases [64][67][68][69][70][71].

3. BPA

BPA is a monomer in the production of polycarbonate plastics and epoxy resins, and as an additive in the production of PVC coatings is added to various plastics as a plasticizer. These materials are used in food storage containers, water, baby bottles, food, and drink cans. Under the influence of elevated temperature, BPA may migrate from containers to food and beverages [4][72]. BPA-derived monomers, especially bis-GMA (methacrylate bisphenol–glycidyl) are used in dental materials, from where they can be released [73]. The release of BPA to the aquatic environment takes place in several ways, including from production plants, from wastewater as a result of incomplete treatment, or in physicochemical and biological processes in treatment units, from leachate from landfills, as well as from leaching from discarded BPA-based products [24][74][75][76][77]. The problem is also sludge from recycled paper, the production of which uses BPA as a reactive agent. These sediments are used as fertilizers in agriculture, eventually contaminating the groundwater with BPA [78]. BPA also enters groundwater through its release to landfill leachate [44][79][80][81][82]. The results showed that the leaching of BPA from polyethylene microplastics (LDPE) and polycarbonate (PC) was 2.68 μg/g and 14.45 μg/g, respectively [83]. Studies have shown that diffusion of BPA in the environment is related to the hydrolysis of PC: processing time for polycarbonate bottles in the presence of water is only a few (3–7) years [84]. BPA concentrations in surface water vary depending on the location, sampling period and depth of sampling. Studies in which both water and sediment were collected indicate significantly higher BPA concentrations in the sediments than in the upper water column, which is related to the slowing down of biodegradation processes in anaerobic environments [79][85][86][87]. Rivers in Europe and North America with higher BPA concentrations detected are commonly associated with production facilities [84][86]. Although BPA dissolved in surface water has a short half-life due to photo- and microbial degradation, its metabolites can persist much longer [88]. The BPA metabolites can be toxic for aquatic organisms [76]. Like BPA, its metabolites are xenoestrogens, e.g., 4.40-dihydroxy-methylstilbene and 4-methyl-2,4-bis (4-hydroxyphenyl) pent-1-ene (MBP), whose estrogenic activity levels exceed BPA levels respectively 40- and 300-fold [89][90]. Observed BPA concentrations in oceans and estuaries are low compared to freshwater systems (Table 1). It is related to the fact that sewage from municipal and mixed municipal-industrial wastewater treatment plants is the main source of environmental BPA, and its runoff goes to rivers [74][85][91][92][93][94]. BPA is leached faster in marine systems than in freshwater systems [95][96], and microbial degradation may be slower [97][98]. Moreover, the bioavailable fraction of dissolved BPA may increase with salinity [96]. The poor biodegradability of BPA in nature leads to the contamination of surface and groundwater. Researchers can remove BPA using the following methods: photodegradation (TiO2) is the most commonly studied and uses photocatalyst, adsorption (natural adsorbents, carbon and graphene, clay, nanomaterials, and composite materials), biodegradation with the use of microorganisms, or phytoremediation [9][99][100][101][102]. The main source of microorganisms in biodegradation is activated sludge from WWTPs. Bacillus thuringiensis, Pseudomonas putida YC-AE1, Sphingomonas paucimobilis FJ-4, Lactococcus lactis, Bacillus subtilis and many more bacteria are capable to use BPA as substrate in their metabolism [84][103]. Among fungi, BPA degradation was observed in Saccharomyces cerevisiae and WRF [104][105]. WRF converts BPA into a much less reactive substance in enzymatic oxidation. The oxidized form of BPA does not bind to ERα dependent estrogen receptors. This may be due to laccase oxidation of both BPA hydroxyl groups. The product obtained by laccase catalyzed oxidation of BPA is 2,2-bis (4-phenylquinone) propane [106].

References

  1. Azizi, D.; Arif, A.; Blair, D.; Dionne, J.; Filion, Y.; Ouarda, Y.; Pazmino, A.G.; Pulicharla, R.; Rilstone, V.; Tiwari, B.; et al. A Comprehensive Review on Current Technologies for Removal of Endocrine Disrupting Chemicals from Wastewaters. Environ. Res. 2022, 207, 112196.
  2. Ismail, N.A.H.; Wee, S.Y.; Aris, A.Z. Multi-Class of Endocrine Disrupting Compounds in Aquaculture Ecosystems and Health Impacts in Exposed Biota. Chemosphere 2017, 188, 375–388.
  3. Diamanti-Kandarakis, E.; Bourguignon, J.P.; Giudice, L.C.; Hauser, R.; Prins, G.S.; Soto, A.M.; Zoeller, R.T.; Gore, A.C. Endocrine-Disrupting Chemicals: An Endocrine Society Scientific Statement. Endocr. Rev. 2009, 30, 293–342.
  4. Metcalfe, C.D.; Bayen, S.; Desrosiers, M.; Muñoz, G.; Sauvé, S.; Yargeau, V. An Introduction to the Sources, Fate, Occurrence and Effects of Endocrine Disrupting Chemicals Released into the Environment. Environ. Res. 2022, 207, 112658.
  5. Giulivo, M.; Lopez de Alda, M.; Capri, E.; Barceló, D. Human Exposure to Endocrine Disrupting Compounds: Their Role in Reproductive Systems, Metabolic Syndrome and Breast Cancer. A Review. Environ. Res. 2016, 151, 251–264.
  6. Darbre, P.D. Endocrine Disruptors and Obesity. Curr. Obes. Rep. 2017, 6, 18–27.
  7. Dalrymple, O.K.; Yeh, D.H.; Trotz, M.A. Removing Pharmaceuticals and Endocrine-Disrupting Compounds from Wastewater by Photocatalysis. J. Chem. Technol. Biotechnol. 2007, 82, 121–134.
  8. Tijani, J.O.; Fatoba, O.O.; Petrik, L.F. A Review of Pharmaceuticals and Endocrine-Disrupting Compounds: Sources, Effects, Removal, and Detections. Water Air Soil Pollut. 2013, 224, 1770.
  9. Gao, X.; Kang, S.; Xiong, R.; Chen, M. Environment-Friendly Removal Methods for Endocrine Disrupting Chemicals. Sustainability 2020, 12, 7615.
  10. de Bruin, W.; Kritzinger, Q.; Bornman, R.; Korsten, L. Occurrence, Fate and Toxic Effects of the Industrial Endocrine Disrupter, Nonylphenol, on Plants—A Review. Ecotoxicol. Environ. Saf. 2019, 181, 419–427.
  11. Noorimotlagh, Z.; Mirzaee, S.A.; Martinez, S.S.; Rachoń, D.; Hoseinzadeh, M.; Jaafarzadeh, N. Environmental Exposure to Nonylphenol and Cancer Progression Risk—A Systematic Review. Environ. Res. 2020, 184, 109263.
  12. Soares, A.; Guieysse, B.; Jefferson, B.; Cartmell, E.; Lester, J.N. Nonylphenol in the Environment: A Critical Review on Occurrence, Fate, Toxicity and Treatment in Wastewaters. Environ. Int. 2008, 34, 1033–1049.
  13. Bhandari, G.; Bagheri, A.R.; Bhatt, P.; Bilal, M. Occurrence, Potential Ecological Risks, and Degradation of Endocrine Disrupter, Nonylphenol, from the Aqueous Environment. Chemosphere 2021, 275, 1300132.
  14. Björklund, K.; Cousins, A.P.; Strömvall, A.M.; Malmqvist, P.A. Phthalates and Nonylphenols in Urban Runoff: Occurrence, Distribution and Area Emission Factors. Sci. Total Environ. 2009, 407, 4665–4672.
  15. Yuan, S.Y.; Yu, C.H.; Chang, B.V. Biodegradation of Nonylphenol in River Sediment. Environ. Pollut. 2004, 127, 425–430.
  16. Lu, Z.; Gan, J. Isomer-Specific Biodegradation of Nonylphenol in River Sediments and Structure-Biodegradability Relationship. Environ. Sci. Technol. 2014, 48, 1008–1014.
  17. Kovarova, J.; Blahova, J.; Divisova, L.; Svobodova, Z. Alkylphenol Ethoxylates and Alkylphenols-Update Information on Occurrence, Fate and Toxicity in Aquatic Environment. Pol. J. Vet. Sci. 2013, 16, 763–772.
  18. Kawamura, Y.; Ogawa, Y.; Mutsuga, M. Migration of Nonylphenol and Plasticizers from Polyvinyl Chloride Stretch Film into Food Simulants, Rapeseed Oil, and Foods. Food Sci. Nutr. 2017, 5, 390–398.
  19. Thiele, B.; Heinke, V.; Kleist, E.; Guenther, K. Contribution to the Structural Elucidation of 110 Isomers of Technical P-Nonylphenol. Environ. Sci. Technol. 2004, 38, 3405–3411.
  20. Preuss, T.G.; Gehrhardt, J.; Schirmer, K.; Coors, A.; Rubach, M.; Russ, A.; Jones, P.D.; Giesy, J.P.; Ratte, H.T. Nonylphenol Isomers Differ in Estrogenic Activity. Environ. Sci. Technol. 2006, 40, 5147–5153.
  21. Krupinski, M.; Długoński, J. Biodegradacja nonylofenoli przez wybrane grupy mikroorganizmów. Post. Mikrobiol. 2011, 50, 313–319.
  22. Oluwole, A.O.; Omotola, E.O.; Olatunji, O.S. Pharmaceuticals and Personal Care Products in Water and Wastewater: A Review of Treatment Processes and Use of Photocatalyst Immobilized on Functionalized Carbon in AOP Degradation. BMC Chem. 2020, 14, 62.
  23. Liu, Z.; Kanjo, Y.; Mizutani, S. Removal Mechanisms for Endocrine Disrupting Compounds (EDCs) in Wastewater Treatment-Physical Means, Biodegradation, and Chemical Advanced Oxidation: A Review. Sci. Total Environ. 2009, 407, 731–748.
  24. Yang, Y.; Lu, L.; Zhang, J.; Yang, Y.; Wu, Y.; Shao, B. Simultaneous Determination of Seven Bisphenols in Environmental Water and Solid Samples by Liquid Chromatography-Electrospray Tandem Mass Spectrometry. J. Chromatogr. A 2014, 1328, 26–34.
  25. Xu, W.; Yan, W.; Huang, W.; Miao, L.; Zhong, L. Endocrine-Disrupting Chemicals in the Pearl River Delta and Coastal Environment: Sources, Transfer, and Implications. Environ. Geochem. Health 2014, 36, 1095–1104.
  26. Yang, Y.; Cao, X.; Zhang, M.; Wang, J. Occurrence and Distribution of Endocrine-Disrupting Compounds in the Honghu Lake and East Dongting Lake along the Central Yangtze River, China. Environ. Sci. Pollut. Res. Int. 2015, 22, 17644–17652.
  27. Ślósarczyk, K.; Jakóbczyk-Karpierz, S.; Różkowski, J.; Witkowski, A.J. Occurrence of Pharmaceuticals and Personal Care Products in the Water Environment of Poland: A Review. Water 2021, 13, 2283.
  28. Katrina, K.M.; Espino, M.P. Occurrence and Distribution of Hormones and Bisphenol A in Laguna Lake, Philippines. Chemosphere 2020, 256, 127122.
  29. Lu, J.; Wu, J.; Zhang, C.; Zhang, Y. Possible Effect of Submarine Groundwater Discharge on the Pollution of Coastal Water: Occurrence, Source, and Risks of Endocrine Disrupting Chemicals in Coastal Groundwater and Adjacent Seawater Influenced by Reclaimed Water Irrigation. Chemosphere 2020, 250, 126323.
  30. Li, Z.; Xiang, X.; Li, M.; Ma, Y.; Wang, J.; Liu, X. Occurrence and Risk Assessment of Pharmaceuticals and Personal Care Products and Endocrine Disrupting Chemicals in Reclaimed Water and Receiving Groundwater in China. Ecotoxicol. Environ. Saf. 2015, 119, 74–80.
  31. Ben, W.; Zhu, B.; Yuan, X.; Zhang, Y.; Yang, M.; Qiang, Z. Occurrence, Removal and Risk of Organic Micropollutants in Wastewater Treatment Plants across China: Comparison of Wastewater Treatment Processes. Water Res. 2018, 130, 38–46.
  32. Arditsoglou, A.; Voutsa, D. Occurrence and Partitioning of Endocrine-Disrupting Compounds in the Marine Environment of Thermaikos Gulf, Northern Aegean Sea, Greece. Mar. Pollut. Bull. 2012, 64, 2443–2452.
  33. Song, J.; Nagae, M.; Takao, Y.; Soyano, K. Field Survey of Environmental Estrogen Pollution in the Coastal Area of Tokyo Bay and Nagasaki City Using the Japanese Common Goby Acanthogobius flavimanus. Environ. Pollut. 2020, 258, 113673.
  34. Shen, J.; Li, X.; Wang, X.; Feng, J.; He, X.; Jiang, S.; Zhou, A.; Ouyang, X. Study on the Release Potential of BPA and Steroid Estrogens in the Sediments of Erhai Lake, a Typical Plateau Lake of China. Bull. Environ. Contam. Toxicol. 2020, 105, 882–891.
  35. Müller, A.K.; Markert, N.; Leser, K.; Kämpfer, D.; Crawford, S.E.; Schäffer, A.; Segner, H.; Hollert, H. Assessing Endocrine Disruption in Freshwater Fish Species from a “Hotspot” for Estrogenic Activity in Sediment. Environ. Pollut. 2020, 257, 113636.
  36. Hadibarata, T.; Ayu Kristanti, R.; Hossam Mahmoud, A. Occurrence of Endocrine-Disrupting Chemicals (EDCs) in River Water and Sediment of the Mahakam River. J. Water Health 2020, 18, 38–47.
  37. Emnet, P.; Mahaliyana, A.S.; Northcott, G.; Gaw, S. Organic Micropollutants in Wastewater Effluents and the Receiving Coastal Waters, Sediments, and Biota of Lyttelton Harbour (Te Whakaraupō), New Zealand. Arch. Environ. Contam. Toxicol. 2020, 79, 461–477.
  38. Zaborska, A.; Siedlewicz, G.; Szymczycha, B.; Dzierzbicka-Głowacka, L.; Pazdro, K. Legacy and Emerging Pollutants in the Gulf of Gdańsk (Southern Baltic Sea)–Loads and Distribution Revisited. Mar. Pollut. Bull. 2019, 139, 238–255.
  39. Čelić, M.; Škrbić, B.D.; Insa, S.; Živančev, J.; Gros, M.; Petrović, M. Occurrence and Assessment of Environmental Risks of Endocrine Disrupting Compounds in Drinking, Surface and Wastewaters in Serbia. Environ. Pollut. 2020, 262, 114344.
  40. Wang, S.; Wu, W.; Liu, F.; Yin, S.; Bao, Z.; Liu, H. Spatial Distribution and Migration of Nonylphenol in Groundwater Following Long-Term Wastewater Irrigation. J. Contam. Hydrol. 2015, 177, 85–92.
  41. Gao, D.; Li, Z.; Guan, J.; Liang, H. Seasonal Variations in the Concentration and Removal of Nonylphenol Ethoxylates from the Wastewater of a Sewage Treatment Plant. J. Environ. Sci. 2017, 54, 217–223.
  42. Li, Z.; Gibson, M.; Liu, C.; Hu, H. Seasonal Variation of Nonylphenol Concentrations and Fluxes with Influence of Flooding in the Daliao River Estuary, China. Environ. Monit. Assess. 2013, 185, 5221–5230.
  43. Mao, Z.; Zheng, X.F.; Zhang, Y.Q.; Tao, X.X.; Li, Y.; Wang, W. Occurrence and Biodegradation of Nonylphenol in the Environment. Int. J. Mol. Sci. 2012, 13, 491–505.
  44. Lacorte, S.; Latorre, A.; Guillamon, M.; Barceló, D. Nonylphenol, Octyphenol, and Bisphenol A in Groundwaters as a Result of Agronomic Practices. Sci. World J. 2002, 2, 1095–1100.
  45. Stuart, M.E.; Manamsa, K.; Talbot, J.C.; Crane, E.J. Emerging Contaminants in Groundwater; Open Report OR/11/013; British Geological Survey: Keyworth, UK, 2011.
  46. Vulliet, E.; Tournier, M.; Vauchez, A.; Wiest, L.; Baudot, R.; Lafay, F.; Kiss, A.; Cren-Olivé, C. Survey Regarding the Occurrence of Selected Organic Micropollutants in the Groundwaters of Overseas Departments. Environ. Sci. Pollut. Res. 2014, 21, 7512–7521.
  47. Langford, K.H.; Scrimshaw, M.D.; Birkett, J.W.; Lester, J.N. Degradation of Nonylphenolic Surfactants in Activated Sludge Batch Tests. Water Res. 2005, 39, 870–876.
  48. Koh, Y.K.K.; Lester, J.N.; Scrimshaw, M.D. Fate and Behavior of Alkylphenols and Their Polyethoxylates in an Activated Sludge Plant. Bull. Environ. Contam. Toxicol. 2005, 75, 1098–1106.
  49. Johnson, M.A.; Song, X.; Seagren, E.A. A Quantitative Framework for Understanding Complex Interactions between Competing Interfacial Processes and In Situ Biodegradation. J. Contam. Hydrol. 2013, 146, 16–36.
  50. Gabriel, F.L.P.; Routledge, E.J.; Heidlberger, A.; Rentsch, D.; Guenther, K.; Giger, W.; Sumpter, J.P.; Kohler, H.P.E. Isomer-Specific Degradation and Endocrine Disrupting Activity of Nonylphenols. Environ. Sci. Technol. 2008, 42, 6399–6408.
  51. Ruiz, Y.; Medina, L.; Borusiak, M.; Ramos, N.; Pinto, G.; Valbuena, O. Biodegradation of Polyethoxylated Nonylphenols. ISRN Microbiol. 2013, 2013, 284950.
  52. de Weert, J.; Viñas, M.; Grotenhuis, T.; Rijnaarts, H.; Langenhoff, A. Aerobic Nonylphenol Degradation and Nitro-Nonylphenol Formation by Microbial Cultures from Sediments. Appl. Microbiol. Biotechnol. 2010, 86, 761–771.
  53. Ho, H.; Watanabe, T. Distribution and Removal of Nonylphenol Ethoxylates and Nonylphenol from Textile Wastewater—A Comparison of a Cotton and a Synthetic Fiber Factory in Vietnam. Water 2017, 9, 386.
  54. Carotenuto, M.; Libralato, G.; Gürses, H.; Siciliano, A.; Rizzo, L.; Guida, M.; Lofrano, G. Nonylphenol Deca-Ethoxylate Removal from Wastewater by UV/H2O2: Degradation Kinetics and Toxicity Effects. Process Saf. Environ. Prot. 2019, 124, 1–7.
  55. Ouyang, W.; Chen, T.; Shi, Y.; Tong, L.; Chen, Y.; Wang, W.; Yang, J.; Xue, J. Physico-Chemical Processes. Water Environ. Res. 2019, 91, 1350–1377.
  56. Kose-Mutlu, B.; Ersahin, M.E.; Ozgun, H.; Kaya, R.; Kinaci, C.; Koyuncu, I. Influence of Powdered and Granular Activated Carbon System as a Pre-Treatment Alternative for Membrane Filtration of Produced Water. J. Chem. Technol. Biotechnol. 2017, 92, 283–291.
  57. Tanghe, T.; Dhooge, W.; Verstraete, W. Isolation of a Bacterial Strain Able to Degrade Branched Nonylphenol. Appl. Environ. Microbiol. 1999, 65, 746–751.
  58. Chandran, H.; Meena, M.; Sharma, K. Microbial Biodiversity and Bioremediation Assessment Through Omics Approaches. Front. Environ. Chem. 2020, 1, 570326.
  59. Corvini, P.F.X.; Schäffer, A.; Schlosser, D. Microbial Degradation of Nonylphenol and Other Alkylphenols—Our Evolving View. Appl. Microbiol. Biotechnol. 2006, 72, 223–243.
  60. Bai, N.; Abuduaini, R.; Wang, S.; Zhang, M.; Zhu, X.; Zhao, Y. Nonylphenol Biodegradation Characterizations and Bacterial Composition Analysis of an Effective Consortium NP-M2. Environ. Pollut. 2017, 220, 95–104.
  61. Ma, J.; Chen, F.Y.; Tang, Y.; Wang, X.G. Research on Degradation Characteristics of Nonylphenol in Water by Highly Effective Complex Microorganisms. E3S Web Conf. 2018, 53, 04016.
  62. Chang, B.V.; Yu, C.H.; Yuan, S.Y. Degradation of Nonylphenol by Anaerobic Microorganisms from River Sediment. Chemosphere 2004, 55, 493–500.
  63. Duan, X.; Wang, X.; Xie, J.; Feng, L.; Yan, Y.; Wang, F.; Zhou, Q. Acidogenic Bacteria Assisted Biodegradation of Nonylphenol in Waste Activated Sludge during Anaerobic Fermentation for Short-Chain Fatty Acids Production. Bioresour. Technol. 2018, 268, 692–699.
  64. Grelska, A.; Noszczyńska, M. White Rot Fungi Can Be a Promising Tool for Removal of Bisphenol A, Bisphenol S, and Nonylphenol from Wastewater. Environ. Sci. Pollut. Res. Int. 2020, 27, 39958–39976.
  65. Balcázar-López, E.; Méndez-Lorenzo, L.H.; Batista-García, R.A.; Esquivel-Naranjo, U.; Ayala, M.; Kumar, V.V.; Savary, O.; Cabana, H.; Herrera-Estrella, A.; Folch-Mallol, J.L. Xenobiotic Compounds Degradation by Heterologous Expression of a Trametes sanguineus Laccase in Trichoderma Atroviride. PLoS ONE 2016, 11, e0147997.
  66. Cabana, H.; Jiwan, J.L.H.; Rozenberg, R.; Elisashvili, V.; Penninckx, M.; Agathos, S.N.; Jones, J.P. Elimination of Endocrine Disrupting Chemicals Nonylphenol and Bisphenol A and Personal Care Product Ingredient Triclosan Using Enzyme Preparation from the White Rot Fungus Coriolopsis polyzona. Chemosphere 2007, 67, 770–778.
  67. Chang, B.V.; Chang, Y.M. Biodegradation of Toxic Chemicals by Pleurotus eryngii in Submerged Fermentation and Solid-State Fermentation. J. Microbiol. Immunol. Infect. 2016, 49, 175–181.
  68. Mo, D.; Zeng, G.; Yuan, X.; Chen, M.; Hu, L.; Li, H.; Wang, H.; Xu, P.; Lai, C.; Wan, J.; et al. Molecular Docking Simulation on the Interactions of Laccase from Trametes versicolor with Nonylphenol and Octylphenol Isomers. Bioprocess Biosyst. Eng. 2018, 41, 331–343.
  69. Soares, A.; Guieysse, B.; Mattiasson, B. Influence of Agitation on the Removal of Nonylphenol by the White-Rot Fungi Trametes versicolor and Bjerkandera sp. BOL 13. Biotechnol. Lett. 2006, 28, 139–143.
  70. Xu, P.; Lai, C.; Zeng, G.; Huang, D.; Chen, M.; Song, B.; Peng, X.; Wan, J.; Hu, L.; Duan, A.; et al. Enhanced Bioremediation of 4-Nonylphenol and Cadmium Co-Contaminated Sediment by Composting with Phanerochaete chrysosporium Inocula. Bioresour. Technol. 2018, 250, 625–634.
  71. Huang, D.; Qin, X.; Xu, P.; Zeng, G.; Peng, Z.; Wang, R.; Wan, J.; Gong, X.; Xue, W. Composting of 4-Nonylphenol-Contaminated River Sediment with Inocula of Phanerochaete chrysosporium. Bioresour. Technol. 2016, 221, 47–54.
  72. Ginter-Kramarczyk, D.; Zembrzuska, J.; Kruszelnicka, I.; Zając-Woźnialis, A.; Ciślak, M. Influence of Temperature on the Quantity of Bisphenol A in Bottled Drinking Water. Int. J. Environ. Res. Public Health 2022, 19, 5710.
  73. Drozdz, K.; Wysokinski, D.; Krupa, R.; Wozniak, K. Bisphenol A-Glycidyl Methacrylate Induces a Broad Spectrum of DNA Damage in Human Lymphocytes. Arch. Toxicol. 2011, 85, 1453–1461.
  74. Gewurtz, S.B.; Tardif, G.; Power, M.; Backus, S.M.; Dove, A.; Dubé-Roberge, K.; Garron, C.; King, M.; Lalonde, B.; Letcher, R.J. Bisphenol A in the Canadian Environment: A Multimedia Analysis. Sci. Total Environ. 2021, 755, 142472.
  75. Rotimi, O.A.; Olawole, T.D.; de Campos, O.C.; Adelani, I.B.; Rotimi, S.O. Bisphenol A in Africa: A Review of Environmental and Biological Levels. Sci. Total Environ. 2021, 764, 142854.
  76. Nath, A.; Biswas, S.; Pal, A. A Comprehensive Review on BPA Degradation by Heterogeneous Fenton-like Processes. Water Sci. Technol. 2022, 86, 714–745.
  77. Bousoumah, R.; Leso, V.; Iavicoli, I.; Huuskonen, P.; Viegas, S.; Porras, S.P.; Santonen, T.; Frery, N.; Robert, A.; Ndaw, S. Biomonitoring of Occupational Exposure to Bisphenol A, Bisphenol S and Bisphenol F: A Systematic Review. Sci. Total Environ. 2021, 783, 146905.
  78. Mohapatra, D.P.; Brar, S.K.; Tyagi, R.D.; Surampalli, R.Y. Physico-Chemical Pre-Treatment and Biotransformation of Wastewater and Wastewater Sludge-Fate of Bisphenol A. Chemosphere 2010, 78, 923–941.
  79. Careghini, A.; Mastorgio, A.F.; Saponaro, S.; Sezenna, E. Bisphenol A, Nonylphenols, Benzophenones, and Benzotriazoles in Soils, Groundwater, Surface Water, Sediments, and Food: A Review. Environ. Sci. Pollut. Res. 2015, 22, 5711–5741.
  80. Dueñas-Moreno, J.; Mora, A.; Cervantes-Avilés, P.; Mahlknecht, J. Groundwater Contamination Pathways of Phthalates and Bisphenol A: Origin, Characteristics, Transport, and Fate—A Review. Environ. Int. 2022, 170, 107550.
  81. Teuten, E.L.; Saquing, J.M.; Knappe, D.R.U.; Barlaz, M.A.; Jonsson, S.; Björn, A.; Rowland, S.J.; Thompson, R.C.; Galloway, T.S.; Yamashita, R. Transport and Release of Chemicals from Plastics to the Environment and to Wildlife. Philos. Trans. R. Soc. Lond. B Biol. Sci. 2009, 364, 2027–2045.
  82. Narevski, A.C.; Novaković, M.I.; Petrović, M.Z.; Mihajlović, I.J.; Maoduš, N.B.; Goran, V.V. Occurrence of Bisphenol A and Microplastics in Landfill Leachate: Lessons from South East Europe. Environ. Sci. Pollut. Res. Int. 2021, 28, 42196–42203.
  83. Liu, J.; Zhang, L.; Lu, G.; Jiang, R.; Yan, Z.; Li, Y. Occurrence, Toxicity and Ecological Risk of Bisphenol A Analogues in Aquatic Environment—A Review. Ecotoxicol. Environ. Saf. 2021, 208, 111481.
  84. Xing, J.; Zhang, S.; Zhang, M.; Hou, J. A Critical Review of Presence, Removal and Potential Impacts of Endocrine Disruptors Bisphenol A. Comp. Biochem. Physiol. Part-C Toxicol. Pharmacol. 2022, 254, 109275.
  85. Goeury, K.; Munoz, G.; Vo Duy, S.; Prévost, M.; Sauvé, S. Occurrence and Seasonal Distribution of Steroid Hormones and Bisphenol A in Surface Waters and Suspended Sediments of Quebec, Canada. Environ. Adv. 2022, 8, 100199.
  86. Staples, C.; van der Hoeven, N.; Clark, K.; Mihaich, E.; Woelz, J.; Hentges, S. Distributions of Concentrations of Bisphenol A in North American and European Surface Waters and Sediments Determined from 19 Years of Monitoring Data. Chemosphere 2018, 201, 448–458.
  87. Zheng, C.; Liu, J.; Ren, J.; Shen, J.; Fan, J.; Xi, R.; Chen, W.; Chen, Q. Occurrence, Distribution and Ecological Risk of Bisphenol Analogues in the Surface Water from a Water Diversion Project in Nanjing, China. Int. J. Environ. Res. Public Health 2019, 16, 3296.
  88. Flint, S.; Markle, T.; Thompson, S.; Wallace, E. Bisphenol A Exposure, Effects, and Policy: A Wildlife Perspective. J. Environ. Manag. 2012, 104, 19–34.
  89. Yamaguchi, A.; Ishibashi, H.; Kohra, S.; Arizono, K.; Tominaga, N. Short-Term Effects of Endocrine-Disrupting Chemicals on the Expression of Estrogen-Responsive Genes in Male Medaka. Aquat. Toxicol. 2005, 72, 239–249.
  90. Okuda, K.; Takiguchi, M.; Yoshihara, S. In Vivo Estrogenic Potential of 4-Methyl-2,4-Bis(4-Hydroxyphenyl)Pent-1-Ene, an Active Metabolite of Bisphenol A, in Uterus of Ovariectomized Rat. Toxicol. Lett. 2010, 197, 7–11.
  91. Zhao, X.; Qiu, W.; Zheng, Y.; Xiong, J.; Gao, C.; Hu, S. Occurrence, Distribution, Bioaccumulation, and Ecological Risk of Bisphenol Analogues, Parabens and Their Metabolites in the Pearl River Estuary, South China. Ecotoxicol. Environ. Saf. 2019, 180, 43–52.
  92. Xie, J.; Zhao, N.; Zhang, Y.; Hu, H.; Zhao, M.; Jin, H. Occurrence and Partitioning of Bisphenol Analogues, Triclocarban, and Triclosan in Seawater and Sediment from East China Sea. Chemosphere 2022, 287, 132218.
  93. Mukhopadhyay, M.; Sampath, S.; Muñoz-Arnanz, J.; Jiménez, B.; Chakraborty, P. Plasticizers and Bisphenol A in Adyar and Cooum Riverine Sediments, India: Occurrences, Sources and Risk Assessment. Environ. Geochem. Health 2020, 42, 2789–2802.
  94. Huang, Z.; Hua, P.; Wang, Z.; Li, R.; Dong, L.; Hu, B.X.; Zhang, J. Environmental Behavior and Potential Driving Force of Bisphenol A in the Elbe River: A Long-Term Trend Study. Sci. Total Environ. 2021, 761, 143251.
  95. Sajiki, J.; Yonekubo, J. Leaching of Bisphenol A (BPA) to Seawater from Polycarbonate Plastic and Its Degradation by Reactive Oxygen Species. Chemosphere 2003, 51, 55–62.
  96. Hu, X.; Peng, J.; Liu, J.; Jiang, G.; Jönsson, J.Å. Evaluating the Impacts of Some Environmentally Relevant Factors on the Availability of Bisphenol A with Negligible-Depletion SPME. Chemosphere 2006, 65, 1935–1941.
  97. Corrales, J.; Kristofco, L.A.; Steele, W.B.; Yates, B.S.; Breed, C.S.; Williams, E.S.; Brooks, B.W. Global Assessment of Bisphenol A in the Environment: Review and Analysis of Its Occurrence and Bioaccumulation. Dose Response 2015, 13, 1559325815598308.
  98. Kang, J.H.; Kondo, F. Bisphenol A Degradation in Seawater Is Different from That in River Water. Chemosphere 2005, 60, 1288–1292.
  99. Ismail, W.N.W.; Mokhtar, S.U. Various Methods for Removal, Treatment, and Detection of Emerging Water Contaminants. In Emerging Contaminants; IntechOpen: London, UK, 2020.
  100. Popov, N. Removal of Emerging Pollutants from Aqueous Matrices; Ana, Q., António, R., Paulo, B., Eds.; Instituto Politécnico de Bragança: Bragança, Portugal, 2020; pp. 17–26.
  101. Jari, Y.; Roche, N.; Necibi, M.C.; el Hajjaji, S.; Dhiba, D.; Chehbouni, A. Emerging Pollutants in Moroccan Wastewater: Occurrence, Impact, and Removal Technologies. J. Chem. 2022, 2022, 9727857.
  102. Bhatnagar, A.; Anastopoulos, I. Adsorptive Removal of Bisphenol A (BPA) from Aqueous Solution: A Review. Chemosphere 2017, 168, 885–902.
  103. Eio, E.J.; Kawai, M.; Tsuchiya, K.; Yamamoto, S.; Toda, T. Biodegradation of Bisphenol A by Bacterial Consortia. Int. Biodeterior. Biodegrad. 2014, 96, 166–173.
  104. Jasińska, A.; Soboń, A.; Różalska, S.; Średnicka, P. Bisphenol a Removal by the Fungus Myrothecium Roridum IM 6482—Analysis of the Cellular and Subcellular Level. Int. J. Mol. Sci. 2021, 22, 10676.
  105. Chai, W.; Handa, Y.; Suzuki, M.; Saito, M.; Kato, N.; Horiuchi, A.C.A. Biodegradation of Bisphenol A by Fungi. Appl. Biochem. Biotechnol. 2005, 120, 175–182.
  106. Bolli, A.; Galluzzo, P.; Ascenzi, P.; del Pozzo, G.; Manco, I.; Vietri, M.T.; Mita, L.; Altucci, L.; Mita, D.G.; Marino, M. Laccase Treatment Impairs Bisphenol A-Induced Cancer Cell Proliferation Affecting Estrogen Receptor α-Dependent Rapid Signals. IUBMB Life 2008, 60, 843–852.
More
© Text is available under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/)
ScholarVision Creations
Feedback