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Occurrence of Xenoestrogen Alkylphenols (Octylphenols and Nonylphenol) and Its Impact on the Aquatic Ecosystem

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Xenobiotics in Aquatic Animals

Abstract

The aquatic ecosystem is one of the most contaminated environments in the present scenario. Recently, the existence of endocrine-disrupting chemicals (EDCs) in the water bodies, including estrogen-like compounds, is increasing. The emerging synthetic xenoestrogen chemicals belonging to alkylphenols (octylphenols and nonylphenol) have been increasingly used as surfactants that are employed in the manufacture of detergents, personal care products, and plastic products. These alkyl phenolic compounds have already been observed in freshwater bodies, drinking water, estuary, and marine ecosystem, thereby raising concerns about their potential consequences on aquatic species. The present review documented the occurrence of alkylphenols (OP and NP) in different environmental compartments and their concentration in aquatic biota. The review aims to identify the estrogenic effect of xenoestrogen (OP and NP) on growth, various developmental stages, and reproductive system of different aquatic animals (males and females). These compounds are known to induce several alterations such as diminished reproductive behavior, change in circulating hormones, gonadosomatic index (GSI), fertilization percentage, histopathological alteration in fish gonads, change in intersex, and increased diameter of oocyte. Moreover, several studies are needed to establish the estrogenic effect of xenoestrogen (OP and NP) on different aquatic animals, especially invertebrates at different developmental stages at different doses and under various environmental conditions.

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References

  • Ackermann GE, Schwaiger J, Negele RD, Fent K (2002) Effects of long-term nonylphenol exposure on gonadal development and biomarkers of estrogenicity in juvenile dam (Awba Dam) in Ibadan, Nigeria. Aquat Toxicol 174:10–21

    Google Scholar 

  • Adeogun AO, Onibonoje K, Ibor OR, Omiwole RA, Chukwuka AV, Ugwumba AO, Ali T, Abdel-Aziz SH, El-Sayed AF, Zeid S (2017) Effects of nonylphenol on plasma steroids, vitellogenin synthesis and sex reversal in Nile tilapia (Oreochromis niloticus) fingerlings. NISCAIR-CSIR, pp 953–960

    Google Scholar 

  • Adeogun AO, Ibor OR, Chukwuka AV, Regoli F, Arukwe A (2019) The intersex phenomenon in Sarotherodon melanotheron from Lagos lagoon (Nigeria): occurrence and severity in relation to contaminants burden in sediment. Environ Pollut 244:747–756

    Article  CAS  PubMed  Google Scholar 

  • Ali TE, Aziz SHA, El-Sayed AFM, Zeid S (2017) Effects of nonylphenol on plasma steroids, vitellogenin synthesis and sex reversal in Nile tilapia (Oreochromis niloticus) fingerlings. Indian J Geo Mar Sci 46(03):521–528

    Google Scholar 

  • Amaninejad P, Hosseinzadeh Sahafi H, Soltani M, Hosseini Shekarabi SP (2018) Endocrine disrupting effects of 4-nonylphenol on plasma vitellogenin, reproductive system and histology in koi carp (Cyprinus carpio). Int Aquat Res 10(3):263–274

    Article  Google Scholar 

  • Bina B, Mohammadi F, Amin MM, Pourzamani HR, Yavari Z (2018) Determination of 4-nonylphenol and 4-tert-octylphenol compounds in various types of wastewater and their removal rates in different treatment processes in nine wastewater treatment plants of Iran. Chin J Chem Eng 26:183–190

    Article  CAS  Google Scholar 

  • Careghini A, Mastorgio AF, Saponaro S, Sezenna E (2015) Bisphenol A, nonylphenols, benzophenones, and benzotriazoles in soils, groundwater, surface water, sediments, and food: a review. Environ Sci Pollut Res 22(8):5711–5741

    Article  CAS  Google Scholar 

  • Chen WL, Gwo JC, Wang GS, Chen CY (2014) Distribution of feminizing compounds in the aquatic environment and bioaccumulation in wild tilapia tissues. Environ Sci Pollut Res Int 21(19):11349–11360

    Article  CAS  PubMed  Google Scholar 

  • Cheng Y, Shan Z, Zhou J, Bu Y, Li P, Lu S (2017) Effects of 4-nonylphenol in drinking water on the reproductive capacity of Japanese quails (Coturnix japonica). Chemosphere 175:219–227

    Article  CAS  PubMed  Google Scholar 

  • Cheng JR, Wang K, Yu J, Yu ZX, Yu XB, Zhang ZZ (2018) Distribution and fate modeling of 4-nonylphenol, 4-t-octylphenol, and bisphenol a in the Yong River of China. Chemosphere 195:594–605

    Article  CAS  PubMed  Google Scholar 

  • Christensen LJ, Korsgaard B, Bjerregaard P (1999) The effect of 4-nonylphenol on the synthesis of vitellogenin in the flounder Platichthys flesus. Aquat Toxicol 46:211–219

    Article  CAS  Google Scholar 

  • Ciocan CM, Cubero-Leon E, Puinean AM, Hill EM, Minier C, Osada M, Rotchell JM (2010) Effects of estrogen exposure in mussels, Mytilus edulis, at different stages of gametogenesis. Environ Pollut 158(9):2977–2984

    Article  CAS  PubMed  Google Scholar 

  • David D, Fenet H, Gomez E (2009) Alkylphenols in marine environments: distribution monitoring strategies and detection considerations. Mar Pollut Bull 58(7):256–262

    Article  Google Scholar 

  • Demska-Zakes K, Zakes Z (2006) Induction of testis-ova in pikeperch (Sander lucioperca (L.)) exposed to 4- nonylphenol. Arch Pol Fish 14(1):29–39

    Google Scholar 

  • Dong RR, Yang SJ, Feng RJ, Fang LL, Sun YL, Zhang YG, Wang DS (2014) Complete feminization of catfish by feeding Limnodilus, an annelid worm collected in contaminated streams. Environ Res 133:371–379

    Article  CAS  PubMed  Google Scholar 

  • Dumitrescu G, Ciochina LP, Voia S, Dronca D, Boca L (2010) Histological changes induced in gonads, liver and kidney of zebra fish (Danio rerio) under the effect octylphenol (OP). Sci Papers Anim Sci Biotechnol 43(1):484–489

    Google Scholar 

  • Errico S, Nicolucci C, Migliaccio M, Micale V, Mita DG, Diano N (2017) Analysis and occurrence of some phenol endocrine disruptors in two marine sites of the northern coast of Sicily (Italy). Mar Pollut Bull 120(1–2):68–74

    Article  CAS  PubMed  Google Scholar 

  • EUROSTAT (2019) Chemicals production and consumption statistics. https://ec.europa.eu/eurostat/documents/3217494/10165279/KS-DK-19-001-EN-N.pdf/76651a29-b817-eed4-f9f2-92bf692e1ed9

  • Fernandes D, Zanuy S, Bebianno MJ, Porte C (2008) Chemical and biochemical tools to assess pollution exposure in cultured fish. Environ Pollut 152(1):728–735

    Article  Google Scholar 

  • Gavrilescu M, Demnerova K, Aamand J, Agathos S, Fava F (2015) Emerging pollutants in the environment: present and future challenges in biomonitoring, ecological risks and bioremediation. New Biotechnol 32:147–156

    Article  CAS  Google Scholar 

  • Hu X-L, Sun Z-W, Wang J-J, An M, Duan S-S (2014) Sublethal toxic effects of nonylphenol ethoxylate and nonylphenol to Moina macrocopa. Bull Environ Contam Toxicol 93:204–208

    Article  CAS  PubMed  Google Scholar 

  • Ismail NAH, Wee SY, Aris AZ (2018) Bisphenol A and alkylphenols concentrations in selected mariculture fish species from Pulau Kukup, Johor, Malaysia. Mar Pollut Bull 127:536–540

    Article  CAS  PubMed  Google Scholar 

  • Jobling S, Sheahan D, Osborne A, Matthiessen P, Sumpter JP (1996) Inhibition of testicular growth in rainbow trout (Oncorhynchus mykiss) exposed to estrogenic alkylphenolic chemicals. Environ Toxicol Chem 343:143–155

    Google Scholar 

  • Kuzikova I, Rybalchenko O, Kurashov E, Krylova Y, Safronova V, Medvedeva N (2020) Defense responses of the marine-derived fungus Аspergillus tubingensis to alkylphenols stress. Water Air Soil Pollut 231(6):1–18

    Article  Google Scholar 

  • Lalonde B, Garron C (2021) Nonylphenol, octylphenol, and nonylphenol ethoxylates dissemination in the Canadian freshwater environment. Arch Environ Contam Toxicol 80(2):319–330

    Article  CAS  PubMed  Google Scholar 

  • Li Z, Zhang W, Shan B (2019) The effects of urbanization and rainfall on the distribution of, and risks from, phenolic environmental estrogens in river sediment. Environ Pollut 250:1010–1018

    Article  CAS  PubMed  Google Scholar 

  • Maack G, Segner H (2004) Life-stage-dependent sensitivity of zebrafish (Danio rerio) to estrogen exposure. Comp Biochem Physiol C Toxicol Pharmacol 139(1–3):47–55. https://doi.org/10.1016/j.cca.2004.09.004

    Article  CAS  PubMed  Google Scholar 

  • Matozzo V, Marin MG (2005) Can 4-nonylphenol induce vitellogenin-like proteins in the clam Tapes philippinarum? Environ Res 97:43–49

    Article  CAS  PubMed  Google Scholar 

  • Meijide FJ, Vázquez GR, Piazza YG, Babay PA, Itria RF, Nostro FLL (2016) Effects of waterborne exposure to 17β-estradiol and 4-tert-octylphenol on early life stages of the South American cichlid fish Cichlasoma dimerus. Ecotoxicol Environ Saf 124:82–90

    Article  CAS  PubMed  Google Scholar 

  • Miyagawa S, Sato T, Iguchi T (2016) Handbook of hormones, comparative endocrinology for basic and clinical research. Subchapter 101A – Nonylphenol

    Google Scholar 

  • Naderi M, Mousavi SM, Safahieh A, Ghatrami ER, Zargham D (2014) Effects of 4- nonylphenol on balance of steroid and thyroid hormones in sexually immature male yellowfin seabream (Acanthopagrus latus). Environ Toxicol 29:459–465

    Article  CAS  PubMed  Google Scholar 

  • Naidu R, Arias Espana VA, Liu Y, Jit J (2016) Emerging contaminants in the environment: risk-based analysis for better management. Chemosphere 154:350–357

    Article  CAS  PubMed  Google Scholar 

  • Nazari E, Suja F (2016) Effects of 17β-estradiol (E2) on aqueous organisms and its treatment problem: a review. Rev Environ Health 31(4):465–491

    Article  CAS  PubMed  Google Scholar 

  • Pal A, Gin KYH, Lin AYC, Reinhard M (2010) Impacts of emerging organic contaminants on freshwater resources: review of recent occurrences, sources, fate and effects. Sci Total Environ 408(24):6062–6069

    Article  CAS  PubMed  Google Scholar 

  • Paris F, Balaguer P, Terouanne B, Servant N, Lacoste C, Cravedi JP, Nicolas JC, Sultan C (2002) Phenylphenols, biphenols, bisphenol-A and 4-tert-octylphenol exhibit alpha and beta estrogen activities and antiandrogen activity in reporter cell lines. Mol Cell Endocrinol 193:43–49

    Article  CAS  PubMed  Google Scholar 

  • Rather MA, Dhandare BC (2019) Genome-wide identification of doublesex and Mab-3-related transcription factor (DMRT) genes in Nile tilapia (Oreochromis niloticus). Biotechnology reports 24:e00398

    Article  PubMed  PubMed Central  Google Scholar 

  • Rather MA, Basha SH, Bhat IA, Sharma N, Nandanpawar P, Badhe M, Sharma R (2017) Characterization, molecular docking, dynamics simulation and metadynamics of kisspeptin receptor with kisspeptin. Int J Biol Macromol 101:241–253

    Article  CAS  PubMed  Google Scholar 

  • Rey Vázquez G, Meijide FJ, Lo Nostro FL (2016) Recovery of the reproductive capability following exposure to 4-tert-octylphenol in the neotropical cichlid fish Cichlasoma dimerus. Bull Environ Contam Toxicol 96(5):585–590

    Article  PubMed  Google Scholar 

  • Rivero CLG, Barbosa AC, Ferreira MFN, Dorea JG, Grisolia CK (2008) Evaluation of genotoxicity and effects on reproduction of nonylphenol in Oreochromis niloticus (Pisces: Cichlidae). Ecotoxicology 17:732–737

    Article  CAS  PubMed  Google Scholar 

  • Ruczyńska W, Szlinder-Richert J, Nermer T (2020) The occurrence and distribution of nonylphenols and nonylphenol ethoxylates in different species of fish. Environ Sci: Processes Impacts 22(4):1057–1070

    Google Scholar 

  • Salgueiro-González N, Turnes-Carou I, Muniategui-Lorenzo S, López-Mahía P, Prada-Rodríguez D (2012) Fast and selective pressurized liquid extraction with simultaneous in cell clean up for the analysis of alkylphenols and bisphenol A in bivalve molluscs. J Chromatogr A 1270:80–87

    Article  PubMed  Google Scholar 

  • Salgueiro-González N, Turnes-Carou I, Viñas L, Besada V, Muniategui-Lorenzo S, López-Mahía P, Prada-Rodríguez D (2016) Occurrence of alkylphenols and bisphenol a in wild mussel samples from the Spanish Atlantic coast and Bay of Biscay. Mar Pollut Bull 106(1–2):360–365

    Article  PubMed  Google Scholar 

  • Saravanan M, Nam SE, Eom HJ, Lee DH, Rhee JS (2019) Long-term exposure to waterborne nonylphenol alters reproductive physiological parameters in economically important marine fish. Comp Biochem Physiol C Toxicol Pharmacol 216:10–18

    Article  CAS  PubMed  Google Scholar 

  • Sayed AEDH, Mahmoud UM, Mekkawy IA (2012) Reproductive biomarkers to identify endocrine disruption in Clarias gariepinus exposed to 4-nonylphenol. Ecotoxicol Environ Saf 78:310–319

    Article  CAS  PubMed  Google Scholar 

  • Sharma VK, Anquandah GA, Yngard RA, Kim H, Fekete J, Bouzek K et al (2009) Nonylphenol, octylphenol, and bisphenol-a in the aquatic environment: a review on occurrence, fate, and treatment. J Environ Sci Health A 44(5):423–442

    Article  CAS  Google Scholar 

  • Shirdel I, Kalbassi MR, Esmaeilbeigi M, Tinoush B (2020) Disruptive effects of nonylphenol on reproductive hormones, antioxidant enzymes, and histology of liver, kidney and gonads in Caspian trout smolts. Comp Biochem Physiol C Toxicol Pharmacol 232:108756

    Article  CAS  PubMed  Google Scholar 

  • Soares A, Guieysse B, Jefferson B, Cartmell E, Lester JN (2008) Nonylphenol in the environment: a critical review on occurrence, fate, toxicity and treatment in wastewaters. Environ Int 34(7):1033–1049

    Article  CAS  PubMed  Google Scholar 

  • Staniszewska M, Falkowska L, Grabowski P, Kwaśniak J, Mudrak-Cegiołka S, Reindl AR, Zgrundo A (2014) Bisphenol A, 4-tert-octylphenol, and 4-nonylphenol in the Gulf of Gdańsk (Southern Baltic). Arch Environ Contam Toxicol 67(3):335–347

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Suman RC, Jiwatram GG (2021) 4-Nonylphenol affects the structure and function of testis in catfish H. fossilis and C. batrachus. J Sci Res 65(5):155–163

    Google Scholar 

  • Sumpter JP, Jobling S (2013) The occurrence, causes, and consequences of estrogens in the aquatic environment. Environ Toxicol Chem 32(2):249–251

    Article  CAS  PubMed  Google Scholar 

  • Sundaray JK, Rather MA, Kumar S, Agarwal D (2021) Recent updates in molecular endocrinology and reproductive physiology of fish. Springer, Singapore

    Book  Google Scholar 

  • Thompson PA, Khatami M, Baglole CJ, Sun J, Harris SA, Moon EY (2015) Environmental immune disruptors, inflammation and cancer risk. Carcinogenesis, Chemosphere 256–266

    Google Scholar 

  • Tiwari M, Sahu SK, Pandit GG (2016) Distribution and estrogenic potential of endocrine disrupting chemicals (EDCs) in estuarine sediments from Mumbai, India. Environ Sci Pollut Res 23(18):18789–18799

    Article  CAS  Google Scholar 

  • Uğuz C, İşcan M, Togan İ (2009) Alkylphenols in the environment and their adverse effects on living organisms. Kocatepe Vet J 2(1):49–58

    Google Scholar 

  • US EPA (2010) Nonylphenol (NP) and nonylphenol ethoxylates (NPEs) action plan

    Google Scholar 

  • Van Zijl MC, Aneck-Hahn NH, Swart P, Hayward S, Genthe B, De Jager C (2017) Estrogenic activity, chemical levels and health risk assessment of municipal distribution point water from Pretoria and Cape Town, South Africa. Chemosphere 186:305–313

    Article  PubMed  Google Scholar 

  • Vargas-Berrones K, Bernal-Jácome L, de León-Martínez LD, Flores-Ramírez R (2020a) Emerging pollutants (EPs) in Latin América: a critical review of under-studied EPs, case of study-nonylphenol. Sci Total Environ 726:138493

    Article  CAS  PubMed  Google Scholar 

  • Vargas-Berrones K, de León-Martínez LD, Bernal-Jácome L, Rodriguez-Aguilar M, Ávila-Galarza A, Flores-Ramírez R (2020b) Rapid analysis of 4-nonylphenol by solid phase microextraction in water samples. Talanta 209:120546

    Article  CAS  PubMed  Google Scholar 

  • Wang, B., Dong, F., Chen, S., Chen, M., Bai, Y., Tan, J., & Wang, Q. (2016). Phenolic endocrine disrupting chemicals in an urban receiving river (Panlong river) of Yunnan–Guizhou plateau: occurrence, bioaccumulation and sources. Ecotoxicol Environ Saf, 128, 133–142

    Google Scholar 

  • Wu M, Pan C, Yang M, Xu B, Le X, Ma J, Cai L, Chen J (2016) Chemical analysis of fish bile extracts for monitoring endocrine disrupting chemical exposure in water: bisphenol A, alkylphenols, and norethindrone. Environ Toxicol Chem 35(1):182–190. https://doi.org/10.1002/etc.3176

    Article  PubMed  Google Scholar 

  • WWF (2020) Nature. In: WWF (ed) Toxic chemicals, pp 462–473

    Google Scholar 

  • Yang W, Gao X, Wu Y, Wan L, Lu C, Huang J, Zhang W (2021) Chemical-and species-specific toxicity of nonylphenol and octylphenol to microalgae Chlorella pyrenoidosa and Scenedesmus obliquus. Environ Toxicol Pharmacol 81:103517

    Article  CAS  PubMed  Google Scholar 

  • Zafar I, Iftikhar R, Ahmad SU, Rather MA (2021) Genome wide identification, phylogeny, and synteny analysis of sox gene family in common carp (Cyprinus carpio). Biotechnol Rep 30:e00607

    Article  CAS  Google Scholar 

  • Zaytseva TB, Medvedeva NG, Mamontova VN (2015) Peculiarities of the effect of octyl-and nonylphenols on the growth and development of microalgae. Inland Water Biol 8(4):406–413

    Article  Google Scholar 

  • Zhao JL, Huang Z, Zhang QQ, Ying-He L, Wang TT, Yang YY, Ying GG (2021) Distribution and mass loads of xenoestrogens bisphenol a, 4-nonylphenol, and 4-tert-octylphenol in rainfall runoff from highly urbanized regions: a comparison with point sources of wastewater. J Hazard Mater 401:123747

    Article  CAS  PubMed  Google Scholar 

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Prasad, G.S., Rout, S.K., Malik, M.M., Karmakar, S., Amin, A., Ahmad, I. (2023). Occurrence of Xenoestrogen Alkylphenols (Octylphenols and Nonylphenol) and Its Impact on the Aquatic Ecosystem. In: Rather, M.A., Amin, A., Hajam, Y.A., Jamwal, A., Ahmad, I. (eds) Xenobiotics in Aquatic Animals. Springer, Singapore. https://doi.org/10.1007/978-981-99-1214-8_13

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