Nonylphenols estrogenicity

Cyprid major protein is a larval storage protein necessary for successful metamorphosis. " Production of cyprid major protein was increased in the barnacle Balanus amphitrite following exposure to both nonylphenol and estradiol, suggesting that it may be a potential biomarker of estrogen exposure in invertebrates such as barnacles. " "... 

Hemandez-Raquet G, Soef A, Delgenes N, Balaguer P (2007) Removal of the endocrine disrupter nonylphenol and its estrogenic activity in sludge treatment processes. Water Res 41 2643-2651... 

Koh YKK, Chiu TY, Boobis AR, Scrimshaw MD, Bagnall JP, Soares A, Pollard S, Cartmell E, Lester JN (2009) Influence of operating parameters on the biodegradation of steroid estrogens and nonylphenolic compounds during biological wastewater treatment processes. Environ Sci Technol 43 6646-6654... 

Although the occurrence of the non-ionic surfactant nonylphenol ethoxylate (NPEO Fig. 6.7.1) and its biodegradation intermediates in the aquatic environment has attracted large interest [18] because of the potential of some biotransformation products to mimic estrogenic effects, their fate and distribution in soil environments has been only investigated in a few cases. 

Petrovic A, Diaz A, Ventura F, Barceld D (2003) Occurrence and removal of estrogenic short-chain ethoxy nonylphenolic compounds and their halogenated derivatives during drinking water production. Environ Sci Technol 37 4442-4448... 

Nonylphenol has recently been shown to have estrogenic properties, triggering mitotic activity in rat endometrium and cell proliferation in estrogen-sensitive tumor cells. Potential toxicity to humans who may be exposed to nonylphenol through leaching of plastics has not been determined. 

Depending upon the circumstance and desired effects, endocrine-disrupting chemicals can be either good or bad. The endocrine system is a finely balanced system responsible for fertility and many of the feminine and masculine traits we are all familiar with. Endocrine disruptors are used by millions of women in the form of the pill to control fertility. Chemicals in birth control pills subtly manipulate the endocrine system to reduce fertility. Unfortunately, we now know that many chemicals are capable of influencing the endocrine systems. When these chemicals, such as DDT and TCDD, are released into the environment, they reduce the fertility of wildlife. Exposure to endocrine disruptors is linked to decreased fertility in shellfish, fish, birds, and mammals. Endocrine disruptors such as nonylphenol have been shown to feminize male fish, interfering with reproduction. Some studies have also linked exposure to endocrine disruptors to decreases in human male sperm count. Ironically, urinary metabolites of the birth control pill as well as the female hormone estrogen pass through waste treatment plants and are released into the aquatic environment, where even small concentrations cause feminization of male fish. 

Tsutsumi Y, Haneda T, Nishida T (2001) Removal of estrogenic activities of bisphenol A and nonylphenol by oxidative enzymes from lignin-degrading basidiomycetes. Chemosphere 42 271-276... 

This phenomenon may be also important for all natural estrogens and endocrine-disrupting chemicals (EDCs) which are weak acids, such as 17 -estra-diol, estriol, ethynylestradiol, diethylstilbestrol, nonylphenol, octylphenol, bisphenol-A (BPA), tetrabromobisphenol-A (TBBA), hydroxy polychlorinated biphenyls, and other compounds with hydroxylated aromatic rings. 

Environmental chemicals such as p-nonylphenol (NP), 4-ferf.-octylphenol (OP), 4-ferf.-pentylphenol (TPP), bisphenol-A (BPA), tetrabromobisphenol-A (TBBA), butylbenzylphthalate (BBP), di- -butylphthalate (DBP), butylated hydroxyanisole (BHA), p-chloro-ra-cresol, p-chloro-o-cresol, ds-nonachlor, frans-nonachlor, and the herbicide alachlor [2-chloro-iV-(2,6-diethylphenyl)-N-(methoxymethyl) acetamide] have been discovered to be weakly estrogenic [128,129,137,138]. 

Linear alkylbenzenesulfonates (LAS), alcohol ethoxylates (AEO), and nonylphenol ethoxylates (NPEO) are synthetic surfactants used in the formulation of detergents and other cleaning products and are widely applied in the dye and leather industry and other industrial processes. These compounds, considered as estrogenic, have aroused considerable interest due to the large quantities produced globally. Their low volatility and anionic form make LC-based methods the preferred approach [7]. Due to the presence of different positional isomers, to the biodegradation intermediates, and to the lack of reference standards, LC-MS, and in particular with ESI, is the only technique which enables their identification and quantification in environmental waters. 

Nonylphenol (Figure 5.28), a surfactant intermediate, has an -OH substituted ring structure similar to estradiol but with a long carbon chain attached. Nonylphenol does have estrogenic activity but only 9.0 X 10 6 that of estradiol (Pait and Nelson 2002). 

Recently, the hazardous effects of endocrine disruptors (environmental hormones) such as bisphenol A and nonylphenol on the human body have been reported, and led to the initiation of many studies concerning the detection and structural determination of these compounds present in tiny amounts [57]. As one of the QSAR analyses of environmental hormones, the relationship between their biological activity and chemical hardness has been reported [16]. By applying these analytical methods, the molecular toxicity and estrogen-like activity of environmental hormones have been found... 

Soto AM, Justicia H, Wray JW, Sonnenschein C. p-Nonylphenol An estrogenic xenobiotic released from modified polystyrene. Environ Health Perspect 1991 92 167-73. 

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