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Estrogenic Compounds: Chemical Characteristics, Detection Methods, Biological and Environmental Effects

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See discussions, stats, and author profiles for this publication at: https://www.researchgate.net/publication/324686974 Estrogenic Compounds: Chemical Characteristics, Detection Methods, Biological and Environmental Effects Article in Water Air and Soil Pollution · May 2018 DOI: 10.1007/s11270-018-3796-z CITATION READS 1 232 4 authors: Maria Tereza Pamplona-Silva Dânia Elisa Christofoletti Mazzeo São Paulo State University São Paulo State University 7 PUBLICATIONS 7 CITATIONS 19 PUBLICATIONS 564 CITATIONS SEE PROFILE SEE PROFILE Jaqueline Bianchi Maria Aparecida Marin-Morales São Paulo State University 7 PUBLICATIONS 102 CITATIONS 116 PUBLICATIONS 2,808 CITATIONS SEE PROFILE SEE PROFILE Some of the authors of this publication are also working on these related projects: AVALIAÇÃO DOS EFEITOS TÓXICOS E GENÉTICOS DE MICROCISTINAS SOB SISTEMAS TESTES ANIMAIS E VEGETAIS View project AVALIAÇÃO DOS EFEITOS TOXICOGENÉTICOS DE COMPOSTOS QUÍMICOS POLUIDORES DE RECURSOS HÍDRICOS, POR MEIO DE DIFERENTES BIOENSAIOS. View project All content following this page was uploaded by Maria Tereza Pamplona-Silva on 23 April 2018. The user has requested enhancement of the downloaded file. Water Air Soil Pollut (2018) 229:144 https://doi.org/10.1007/s11270-018-3796-z Estrogenic Compounds: Chemical Characteristics, Detection Methods, Biological and Environmental Effects Maria Tereza Pamplona-Silva & Dânia Elisa Christofoletti Mazzeo & Jaqueline Bianchi & Maria Aparecida Marin-Morales Received: 10 April 2017 /Accepted: 12 April 2018 # Springer International Publishing AG, part of Springer Nature 2018 Abstract Several chemical compounds are being stud- Keywords Endocrine disruptors . Environmental ied for their capacities to cause imbalances in several estrogenicity. Estrogen receptor. Estrogenic hormones . biological systems. Some of those are able to affect the Bioassay. Epigenetic endocrine system and are known as endocrine disruptors. Many negative effects can be induced in Abbreviations the organisms by the action of these chemicals, 17αEE2 17α-Ethinylestradiol highlighting the capacity to cause a decrease in the 17βE2 17β-Estradiol fertility rate, sex inversion, and problems in embryonic 4-CP 4-Cumylphenol development and even cancer in humans. Those con- APEO Alkylphenol ethoxylates taminants can be found in different environmental con- APS Alkylphenols ditions, in groundwater, sediments, residual waters, BBzP Butylbenzyl phthalate sludges, and even in drinking water. The purpose of this BCFs Bioconcentration Factors review is to provide a general overview of the main BPA Bisphenol A estrogenic endocrine disruptors and their effects on liv- DEHP Di(2-ethylhexyl) phthalate ing organisms, showing the most frequently used tools DEP Diethyl phthalate to detect these contaminants in environmental matrices. DES Diethylstilbestrol According to the data found, there is a need to develop DiBP Diisobutyl phthalate more studies and improve the techniques, in order to DiDP Diisodecyl phthalate effectively determine the mechanism of action of these DiNP Diisononyl phthalate contaminants and, thus, establish appropriate strategies DMP Dimethyl phthalate for their removal from the environment and reduce their DnBP Di-n-butyl phthalate actions on living beings. DOP Di-n-octhyl phthalate E1 Estrone : : : E3 Estriol M. T. Pamplona-Silva D. E. C. Mazzeo J. Bianchi ED Endocrine disruptor M. A. Marin-Morales (*) Department of Biology, Institute of Biosciences, UNESP - Univ EDsA Androgenic compounds Estadual Paulista, Av. 24-A, 1515, 13, Rio Claro, SP 506-900, EDsE Estrogenic endocrine disruptors Brazil EDsT Thyroidal compounds e-mail: [email protected] EEQ Estradiol equivalent D. E. C. Mazzeo EFSA European Food Safety Authority Department of Analytical Chemistry, Institute of Chemistry, ER Estrogen receptor UNESP - Univ Estadual Paulista, Araraquara, SP, Brazil ERBA Estrogen receptor binding assay 144 Page 2 of 27 Water Air Soil Pollut (2018) 229:144 GSI Gonadal somatic index hormones (17β-estradiol (17βE2), estrone (E1), and GSI Somatic index estriol (E3)), synthetic hormones (17α-ethinylestradiol HIS Hepatosomatic index (17αEE2), diethylstilbestrol (DES)), and LOAEL Lowest observed adverse effect level phytoestrogens (isoflavones and coumestrol). More- NMDRC Nonmonotonic dose-response curve over, other industrial compounds such as the bisphenol NP Nonylphenols A (BPA), dioxin (2,3,7,8-TCDD), nonylphenols (NP), NP1EO Nonylphenol-mono-ethoxylate octylphenols (OP), phthalates, styrenes, polybrominated NP2EO Ethoxylate biphenyls (PBB), and polychlorinated biphenyls (PCB) OP Octylphenols (Diamanti-Kandarakis et al. 2010), and metals such as PAHs Polycyclic aromatic hydrocarbons cadmium, lithium, barium, chromium, arsenic, and PBB Polybrominated biphenyls antimony are also inducers of alterations in the en- PCB Polychlorinated biphenyls docrine systems (Choe et al. 2003;Diamanti- PVC Polyvinyl chloride Kandarakis et al. 2010). SS Sewage sludge Trudeau and Tyler (2007) separated the EDs in three STP Sewage treatment plant different classes: androgenic compounds (EDsA), TCDD 2,3,7,8-Tetrachloridibenzo-p-dioxin which mimic or block natural testosterone; thyroidal TDI Tolerable daily intake compounds (EDsT), which cause direct and indirect VTG Vitellogenin effects on the thyroid gland; and estrogenic compounds WTPs Water treatment plants (EDsE), which mimic or block natural estrogen. WWTP Wastewater treatment plants Estrogenic compounds are those that possess similar YES Yeast estrogen screen properties to the hormone 17βE2 (main natural estrogen produced by the ovaries), the effects of which are in- duced by interactions with the estrogen receptor and cell systems (Schug et al. 2011). In addition, according to 1 Introduction Kiyama and Wada-Kiyama (2015), EDsE can act on two main pathways: the genomic path, linked to target The great variety of chemical compounds found in the gene transcription, and the nongenomic path, linked to environment may lead to many detrimental disorders in signaling of specific membrane receptors. These con- living organisms, due to the possibility of the interaction taminants are routinely present in the environment and of these compounds with cellular components. Some of can induce estrogenic effects, even at very low concen- them can also induce hormonal responses, similar to trations, causing reproductive and developmental disor- those produced naturally by organisms. ders, both in humans and wild animals (Jugan et al. Several natural and synthetic compounds, such 2009). Due to the relevance, diversity, and complexity as pharmaceutical drugs, pesticides, phytoestrogens, of adverse effects and chemical compounds related to complex mixtures derived from effluents, some in- estrogenic activity, only the EDsE will be discussed in dustrial wastes and several metals, can bind to this review. estrogen receptors (Hilscherova et al. 2000). When Thus, the present review intends to carry out a con- compounds interact with estrogen receptors, they cise approach regarding the main EDsE studied, de- can interfere on the synthesis, secretion, transport, scribing their known effects and mechanism of action. binding, action, or elimination of natural hormones, Additionally, the most frequently used bioassays to de- damaging the organic responses: blocking the ef- tect estrogenic activities in different environmental sam- fects of the hormones and promoting or inhibiting ples will be also highlighted. the endocrine system. The compounds that have these characteristics are called endocrine disruptors (EDs) (Rasier et al. 2006;USEPA2011). 2 Major Contributors to Estrogenic Activity Campbell et al. (2006) cite many natural and synthet- in Environmental Samples ic compounds that act as EDs, among them are agro- chemicals (atrazine, dieldrin, and toxaphene), surfac- Currently, many different chemicals have been recog- tants (alkylphenol ethoxylates (APEOs)), natural nized as potentially estrogenic; however, the EDsE may Water Air Soil Pollut (2018) 229:144 Page 3 of 27 144 not be grouped by their chemical similarity since they present estrogenic activities that result in several alter- present a high variety of chemical structures. According ations in the spermatogonia, spermatocytes, and sper- to Brzozowski et al. (1997), the presence of an aromatic matids, as well as inducing vitellogenin production in ring in the structure is the only requirement to act as an fishes (Bhatia et al. 2014). effective ligand and bind to the estrogenic receptor. APs are synthetic compounds constituted of antioxi- Classical examples of EDsE that are frequently found dants, modified polystyrene, surfactants, and PVC. Gen- in the environment, include natural and synthetic hor- erally, they are present in various effluents and are mones and chemicals as BPA, phthalates, alkylphenols constituted by different sized alkyl groups. The (APs), polycyclic aromatic hydrocarbons (PAHs), and estrogenicity of those substances is related to the reduc- agrochemicals. tion in the alkyl chain size; in other words, the smaller BPA belongs to groups derived from diphenylmethanol the chain, the greater the estrogenicity (Oliveira et al. and isophenol (Yang et al. 2015). In acid pH and high 2007; Servos 1999;USEPA2006, 2010; White et al. temperature, BPA results in a monomer that is used in 1994). The APs and their products, such as APEO, can the production of plastic and polycarbonates, which affect the reproduction of organisms that are exposed to serve to fabricate plastic bottles, CDs, and DVDs
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