SYNTHESIS AND ESTROGENIC ACTIVITY OF BISPHENOL A MONO- AND DI-β-D-GLUCOPYRANOSIDES, PLANT METABOLITES OF BISPHENOL A

2003 ◽  
Vol 22 (10) ◽  
pp. 2275 ◽  
Author(s):  
Kaori Morohoshi ◽  
Fujio Shiraishi ◽  
Yukiko Oshima ◽  
Tomoko Koda ◽  
Nobuyoshi Nakajima ◽  
...  
Keyword(s):  
Bisphenol A ◽  
Estrogenic Activity ◽  
Plant Metabolites

scholarly journals Characterization of Estrogenic Activity and Site-Specific Accumulation of Bisphenol-A in Epididymal Fat Pad: Interfering Effects on the Endocannabinoid System and Temporal Progression of Germ Cells

2021 ◽  
Vol 22 (5) ◽  
pp. 2540
Author(s):  
Teresa Chioccarelli ◽  
Marina Migliaccio ◽  
Antonio Suglia ◽  
Francesco Manfrevola ◽  
Veronica Porreca ◽  
...  
Keyword(s):  
Bisphenol A ◽  
Germ Cell ◽  
Germ Cells ◽  
Estrogenic Activity ◽  
Endocannabinoid System ◽  
Perinatal Period ◽  
Cell Junction ◽  
Cell Content ◽  
Site Specific ◽  
Epididymal Fat

The objective of this work has been to characterize the estrogenic activity of bisphenol-A (BPA) and the adverse effects on the endocannabinoid system (ECS) in modulating germ cell progression. Male offspring exposed to BPA during the foetal-perinatal period at doses below the no-observed-adverse-effect-level were used to investigate the exposure effects in adulthood. Results showed that BPA accumulates specifically in epididymal fat rather than in abdominal fat and targets testicular expression of 3β-hydroxysteroid dehydrogenase and cytochrome P450 aromatase, thus promoting sustained increase of estrogens and a decrease of testosterone. The exposure to BPA affects the expression levels of some ECS components, namely type-1 (CB1) and type-2 cannabinoid (CB2) receptor and monoacylglycerol-lipase (MAGL). Furthermore, it affects the temporal progression of germ cells reported to be responsive to ECS and promotes epithelial germ cell exfoliation. In particular, it increases the germ cell content (i.e., spermatogonia while reducing spermatocytes and spermatids), accelerates progression of spermatocytes and spermatids, promotes epithelial detachment of round and condensed spermatids and interferes with expression of cell–cell junction genes (i.e., zonula occcludens protein-1, vimentin and β-catenin). Altogether, our study provides evidence that early exposure to BPA produces in adulthood sustained and site-specific BPA accumulation in epididymal fat, becoming a risk factor for the reproductive endocrine pathways associated to ECS.

Increased levels of bisphenol A (BPA) in Thai girls with precocious puberty

2016 ◽  
Vol 0 (0) ◽  
Author(s):  
Vichit Supornsilchai ◽  
Chutima Jantarat ◽  
Wichit Nosoognoen ◽  
Sopon Pornkunwilai ◽  
Suttipong Wacharasindhu ◽  
...  
Keyword(s):  
Bisphenol A ◽  
Estrogenic Activity ◽  
Age At Onset ◽  
Ultra Performance Liquid Chromatography ◽  
Cross Sectional Study ◽  
Normal Weight ◽  
Control Groups ◽  
Limit Of Quantification ◽  
Cross Sectional ◽  
Liquid Chromatography Tandem Mass

AbstractReports on the secular trend of pubertal onset indicate a recent earlier start especially in girls. Bisphenol A (BPA), which posses estrogenic activity, might be a cause of advanced puberty. The objective of the study was to determine the association between BPA and advanced puberty.A cross-sectional study was conducted in patients with advanced puberty (n=41) compared to age-matched controls (n=47). Anthropometric measurements, estradiol, basal and gonadotropin releasing hormone (GnRH)-stimulated follicle stimulating hormone (FSH) and luteinizing hormone (LH) levels, uterine sizes, ovarian diameters and bone ages were obtained. Urinary BPA concentrations were analyzed by ultra-performance liquid chromatography-tandem mass spectrometry (UPLC/MSMS) with the lower limit of quantification (LLOQ) of 0.05 ng/mL.The median adjust-BPA concentration in advanced puberty group was higher than in control groups [1.44 vs. 0.59 μg/g creatinine (Cr): p<0.05]. We also found that the median adjust-BPA concentration in girls with advanced puberty who were overweight/obese, was greater than in the normal pubertal overweight/obese girls (1.74 vs. 0.59 μg/g Cr: p<0.05), and was in the same trend among normal weight girls with advanced and normal puberty (0.83 vs. 0.49 μg/g Cr: p=0.09), but not statistically significant.The present findings suggest that BPA exposure appears to be related to an earlier age at onset of puberty especially in obese girls.

Bisphenol A emission factors from industrial sources and elimination rates in a sewage treatment plant

2003 ◽  
Vol 47 (10) ◽  
pp. 117-122 ◽  
Author(s):  
M. Fuerhacker
Keyword(s):  
Bisphenol A ◽  
Estrogenic Activity ◽  
Animal Experiments ◽  
Elimination Rate ◽  
Sewage Treatment Plant ◽  
Treatment Plant ◽  
Emission Factors ◽  
Point Sources ◽  
In Vitro Test

Bisphenol A (BPA) is widely used for the production of epoxy resins and polycarbonate plastics and is considered an endocrine disruptor. Special in vitro test systems and animal experiments showed a weak estrogenic activity. Aquatic wildlife especially could be endangered by waste water discharges. To manage possible risks arising from BPA emissions the major fluxes need to be investigated and the sources of the contamination of municipal treatment plants need to be determined. In this study, five major industrial point sources, two different household areas and the influent and effluent of the corresponding treatment plant (WWTP) were monitored simultaneously at a plant serving 120,000 population equivalents. A paper producing plant was the major BPA contributor to the influent load of the wastewater treatment plant. All the other emissions from point sources, including the two household areas, were considerably lower. The minimum elimination rate in the WTTP could be determined at 78% with an average of 89% of the total BPA-load. For a possible pollution-forecast, or for a comparison between different point sources, emission factors based on COD-emissions were calculated for industrial and household point sources at BPA/COD-ratios between 1.4 ×10−6-125×10−6 and 1.3×10−6-6.3×10−6, respectively.

S2O82−/UV-C and H2O2/UV-C treatment of Bisphenol A: Assessment of toxicity, estrogenic activity, degradation products and results in real water

Chemosphere ◽  
2015 ◽  
Vol 119 ◽  
pp. S115-S123 ◽  
Author(s):  
Tugba Olmez-Hanci ◽  
Duygu Dursun ◽  
Egemen Aydin ◽  
Idil Arslan-Alaton ◽  
Binhan Girit ◽  
...  
Keyword(s):  
Bisphenol A ◽  
Estrogenic Activity ◽  
Degradation Products ◽  
Uv C

scholarly journals The Xenoestrogen Bisphenol A Inhibits Postembryonic Vertebrate Development by Antagonizing Gene Regulation by Thyroid Hormone

Endocrinology ◽  
2009 ◽  
Vol 150 (6) ◽  
pp. 2964-2973 ◽  
Author(s):  
Rachel A. Heimeier ◽  
Biswajit Das ◽  
Daniel R. Buchholz ◽  
Yun-Bo Shi
Keyword(s):  
Bisphenol A ◽  
Estrogenic Activity ◽  
Sex Differentiation ◽  
Inhibitory Effect ◽  
Vertebrate Development ◽  
Developmental Context ◽  
Mammalian Embryos ◽  
Intestinal Remodeling

Bisphenol A (BPA), a chemical widely used to manufacture plastics, is estrogenic and capable of disrupting sex differentiation. However, recent in vitro studies have shown that BPA can also antagonize T3 activation of the T3 receptor. The difficulty in studying uterus-enclosed mammalian embryos has hampered the analysis on the direct effects of BPA during vertebrate development. This study proposed to identify critical T3 pathways that may be disrupted by BPA based on molecular analysis in vivo. Because amphibian metamorphosis requires T3 and encompasses the postembryonic period in mammals when T3 action is most critical, we used this unique model for studying the effect of BPA on T3-dependent vertebrate development at both the morphological and molecular levels. After 4 d of exposure, BPA inhibited T3-induced intestinal remodeling in premetamorphic Xenopus laevis tadpoles. Importantly, microarray analysis revealed that BPA antagonized the regulation of most T3-response genes, thereby explaining the inhibitory effect of BPA on metamorphosis. Surprisingly, most of the genes affected by BPA in the presence of T3 were T3-response genes, suggesting that BPA predominantly affected T3-signaling pathways during metamorphosis. Our finding that this endocrine disruptor, well known for its estrogenic activity in vitro, functions to inhibit T3 pathways to affect vertebrate development in vivo and thus not only provides a mechanism for the likely deleterious effects of BPA on human development but also demonstrates the importance of studying endocrine disruption in a developmental context in vivo.

Oxidation of bisphenol A by permanganate: reaction kinetics and removal of estrogenic activity

2013 ◽  
Vol 67 (8) ◽  
pp. 1867-1872 ◽  
Author(s):  
Jingjing Yang ◽  
Gang Wen ◽  
Ji Zhao ◽  
Xiaoling Shao ◽  
Jun Ma
Keyword(s):  
Bisphenol A ◽  
Reaction Kinetics ◽  
Estrogenic Activity ◽  
Complete Removal ◽  
Order Rate Constant ◽  
Second Order ◽  
Specific Rate ◽  
Order Rate ◽  
Ph Dependency ◽  
Ph Range

The kinetics for reaction between bisphenol A (BPA) and permanganate was examined over pH range of 5.0–9.9 and the estrogenic activity of aqueous BPA solution after oxidation was assessed by yeast two-hybrid assay. Reaction kinetics follows the second-order rate law, with the apparent second-order rate constant of 15.1 ± 1.1 M−1s−1 at pH 6.0 and 25°C and the activation energy of 48.7 kJ/mol. The kinetics exhibits pH dependency and the specific rate constants related to speciation of BPA are 50 ± 28 M−1s−1, 9.6 (±0.6) × 103 M−1s−1 and 1.4 (±0.1) × 104 M−1s−1 for BPA, BPA− and BPA2−, respectively. The results of the estrogenic/antiestrogenic activity test show that there is a hysteresis for the removal of estrogenic activity of aqueous BPA solution at pH 7.3. Removal of BPA is completed in 10 min, but complete removal of estrogenic activity requires a further 20 min.

Synthesis of potential bisphenol A substitutes by isomerising metathesis of renewable raw materials

2017 ◽  
Vol 19 (13) ◽  
pp. 3051-3060 ◽  
Author(s):  
A. S. Trita ◽  
L. C. Over ◽  
J. Pollini ◽  
S. Baader ◽  
S. Riegsinger ◽  
...  
Keyword(s):  
Bisphenol A ◽  
Estrogenic Activity ◽  
Raw Materials ◽  
Building Blocks ◽  
Renewable Raw Materials

Plant-derived alkenyl arenes were converted into polymer building blocks with low estrogenic activity via isomerising metathesis.

In vitro Estrogenicity of Resin Composites

2004 ◽  
Vol 83 (3) ◽  
pp. 222-226 ◽  
Author(s):  
H. Wada ◽  
H. Tarumi ◽  
S. Imazato ◽  
M. Narimatsu ◽  
S. Ebisu
Keyword(s):  
Bisphenol A ◽  
Reporter Gene ◽  
Estrogenic Activity ◽  
Reporter Gene Assay ◽  
Resin Composites ◽  
Minimum Concentration ◽  
Tert Butyl ◽  
Gene Assay

Previously, we have reported that sealants incorporating bisphenol A dimethacrylate showed estrogenicity by a reporter gene assay. This study tested the hypothesis that commercial composites, which contain various monomers and additives, exhibit estrogenic activity in vitro. The estrogenic activities of eluates obtained from 24 composites and 18 chemicals identified from the composites tested were examined with the use of the reporter gene assay. Among the 24 composites, 6 products were estrogenic, and among the 18 constituents, 1 photostabilizer, 2-hydroxy-4-methoxy-benzophenone (HMBP), 1 photoinitiator, 2,2-dimethoxy-2-phenyl-acetophenone (DMPA), and 1 inhibitor, 2,6-di- tert-butyl- p-cresol (BHT) had significant estrogenic activity. The concentration of HMBP in 4 estrogenic eluates was greater than the minimum concentration required for estrogenicity, and DMPA was found at a higher level than the minimum estrogenic concentration in the remaining 2 estrogenic specimens. These results suggest that the observed estrogenic activity of 6 composites is associated with the elution of either HMBP or DMPA.

scholarly journals Adverse Effects of Bisphenol A Exposure on Glucose Metabolism Regulation

2016 ◽  
Vol 10 (1) ◽  
pp. 122-130 ◽  
Author(s):  
Ciro Menale ◽  
Damiano G. Mita ◽  
Nadia Diano ◽  
Sabrina Diano
Keyword(s):  
Insulin Resistance ◽  
Glucose Metabolism ◽  
Adverse Effects ◽  
Bisphenol A ◽  
Estrogenic Activity ◽  
Endocrine Function ◽  
Peripheral Tissues ◽  
Metabolism Regulation

Bisphenol A (BPA) is used as basic chemical compound in the production of polycarbonate food containers or epoxy resins coating metallic cans for food and beverages conservation. Its xeno-estrogenic activity alters endocrine-metabolic pathways modulating glucose metabolism and increasing the risk of developing diabetes, insulin resistance, and obesity. Based on in vitro and in vivo experimental research, here we report some of the major BPA adverse effects on tissues that play a key role in the regulation on the whole body’s metabolism. Evidences have shown that BPA is able to exert its endocrine disrupting action altering glucose metabolism and contributing to the onset of metabolic disorders, acting on liver functions and affecting insulin production by the pancreas. Exposure to BPA has been reported also to modulate glucose utilization in muscles, as well as to interfere with adipose tissue endocrine function. In addition, to peripheral tissues, recent studies have shown that BPA by acting in the Central Nervous System affects neuroendocrine regulation of glucose metabolism, promoting glucose metabolism dysfunction such as glucose intolerance and insulin resistance. Thus, exposure to BPA seems to be an important risk factor in the onset of obesity and metabolic syndrome. However, its mechanisms of action need to be further investigated to provide a major evaluation of risk assessment.

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