scholarly journals 2,2-Bis(4-Hydroxyphenyl)-1-Propanol—A Persistent Product of Bisphenol A Bio-Oxidation in Fortified Environmental Water, as Identified by HPLC/UV/ESI-MS

Toxics ◽  
2021 ◽  
Vol 9 (3) ◽  
pp. 49
Author(s):  
Małgorzata Drzewiecka ◽  
Monika Beszterda ◽  
Magdalena Frańska ◽  
Rafał Frański

Biodegradation of bisphenol A in the environmental waters (lake, river, and sea) has been studied on the base of fortification of the samples taken and the biodegradation products have been analyzed using HPLC/UV/ESI-MS. Analysis of the characteristic fragmentation patterns of [M-H]− ions permitted unambiguous identification of the biodegradation products as 2,2-bis(4-hydroxyphenyl)-1-propanol or as p-hydroxyacetophenone, depending on the type of surface water source. The formation of 2,2-bis(4-hydroxyphenyl)-1-propanol was much more common than that of p-hydroxyacetophenone. Moreover, 2,2-Bis(4-hydroxyphenyl)-1-propanol has not been further biodegraded, in contrast to the p-hydroxyacetophenone, which was further mineralized. It has been proved, for the first time, that 2,2-bis(4-hydroxyphenyl)-1-propanol can be regarded as persistent product of bisphenol A biodegradation in the fortified environmental waters.

2020 ◽  
Author(s):  
Anna Baranova ◽  
Alexey Chistov ◽  
Maxim Shuvalov ◽  
Anton Tyurin ◽  
Mikhail Biryukov ◽  
...  

Nonribosomal cyclopeptide cyclosporin A (CsA), produced by fungus <i>Tolypocladium inflatum</i>, is an extremely important immunosuppressive drug used in organ transplantations and for therapy of autoimmune diseases. Here we report for the first time production of CsA, along with related cyclosporins B and C, by <i>Tolypocladium inflatum </i>strains of marine origin (White Sea). Cyclosporins A–C contain an unusual amino acid, (4<i>R</i>)-4-((<i>E</i>)-2-butenyl)-4,<i>N</i>-dimethyl-l-threonine (MeBmt), and are prone to isomerization to non-active isocyclosporine by N→O acyl shift of valine connected to MeBmt in acidic conditions. CsA and isoCsA are not distinguishable in MS analysis of [M+H]<sup>+</sup> ions due to the rapid [CsA+H]<sup>+</sup>→[isoCsA+H]<sup>+</sup> conversion. We found that the N→O acyl shift is completely suppressed in cyclosporine [M+2H]<sup>2+</sup> ions, and their MS/MS fragmentation can be used for rapid and unambiguous analysis of cyclosporins and isocylosporins. The fragmentation patterns of [CyA+2H]<sup>2+</sup> and [isoCyA+2H]<sup>2+</sup> ions were analyzed and explained. The developed approach could be useful for MS analysis of other peptides containing β-hydroxy-α-amino acids.


2020 ◽  
Author(s):  
Anna Baranova ◽  
Alexey Chistov ◽  
Maxim Shuvalov ◽  
Anton Tyurin ◽  
Mikhail Biryukov ◽  
...  

Nonribosomal cyclopeptide cyclosporin A (CsA), produced by fungus <i>Tolypocladium inflatum</i>, is an extremely important immunosuppressive drug used in organ transplantations and for therapy of autoimmune diseases. Here we report for the first time production of CsA, along with related cyclosporins B and C, by <i>Tolypocladium inflatum </i>strains of marine origin (White Sea). Cyclosporins A–C contain an unusual amino acid, (4<i>R</i>)-4-((<i>E</i>)-2-butenyl)-4,<i>N</i>-dimethyl-l-threonine (MeBmt), and are prone to isomerization to non-active isocyclosporine by N→O acyl shift of valine connected to MeBmt in acidic conditions. CsA and isoCsA are not distinguishable in MS analysis of [M+H]<sup>+</sup> ions due to the rapid [CsA+H]<sup>+</sup>→[isoCsA+H]<sup>+</sup> conversion. We found that the N→O acyl shift is completely suppressed in cyclosporine [M+2H]<sup>2+</sup> ions, and their MS/MS fragmentation can be used for rapid and unambiguous analysis of cyclosporins and isocylosporins. The fragmentation patterns of [CyA+2H]<sup>2+</sup> and [isoCyA+2H]<sup>2+</sup> ions were analyzed and explained. The developed approach could be useful for MS analysis of other peptides containing β-hydroxy-α-amino acids.


2020 ◽  
Vol 26 (5) ◽  
pp. 369-375
Author(s):  
Monika Beszterda ◽  
Rafał Frański

The extracts from the bark of Prunus avium and Prunus cerasus have been analyzed by using high pressure liquid chromatography/electrospray ionization mass spectrometry. For the first time in the bark of Prunus species flavonoid C-glycosides have been detected. On the basis of the characteristic fragmentation patterns of their [M-H]− and [M + H]+ ions, three flavonoid C-glycosides have been identified, namely apigenin-6,8-di-C-glucoside (vicenin-2), apigenin-6-C-glucoside (isovitexin) and chrysin-8-C-glucoside. Taking into account the widely studied biological activities of flavonoid C-glycosides, the barks of these common fruit trees seem to be interesting materials of potential medical or cosmetic application.


Molecules ◽  
2018 ◽  
Vol 23 (11) ◽  
pp. 2994 ◽  
Author(s):  
Stefan Fritzsche ◽  
Susan Billig ◽  
Robby Rynek ◽  
Ramarao Abburi ◽  
Elena Tarakhovskaya ◽  
...  

The great research interest in the quantification of reactive carbonyl compounds (RCCs), such as methylglyoxal (MGO) in biological and environmental samples, is reflected by the fact that several publications have described specific strategies to perform this task. Thus, many reagents have also been reported for the derivatization of RCCs to effectively detect and quantify the resulting compounds using sensitive techniques such as liquid chromatography coupled with mass spectrometry (LC-MS). However, the choice of the derivatization protocol is not always clear, and a comparative evaluation is not feasible because detection limits from separate reports and determined with different instruments are hardly comparable. Consequently, for a systematic comparison, we tested 21 agents in one experimental setup for derivatization of RCCs prior to LC-MS analysis. This consisted of seven commonly employed reagents and 14 similar reagents, three of which were designed and synthesized by us. All reagents were probed for analytical responsiveness of the derivatives and stability of the reaction mixtures. The results showed that derivatives of 4-methoxyphenylenediamine and 3-methoxyphenylhydrazine—reported here for the first time for derivatization of RCCs—provided a particularly high responsiveness with ESI-MS detection. We applied the protocol to investigate MGO contamination of laboratory water and show successful quantification in a lipoxidation experiment. In summary, our results provide valuable information for scientists in establishing accurate analysis of RCCs.


2018 ◽  
Vol 56 (6) ◽  
pp. 681
Author(s):  
Hoang Le Tuan Anh

By using various chromatographic methods, two sterols and one flavone, vernoniamygda A (1), vernoniamygda B (2), and luteolin (3) were isolated from the methanol extract of the leaves of Vernonia amygdalina. Their structures were determined using 1D, 2D-NMR and ESI-MS analysis as well as by comparison with the reported data. Compounds 1 and 2 were reported from natural for the first time.


2015 ◽  
Vol 53 (8) ◽  
pp. 1257-1264 ◽  
Author(s):  
Guilherme Julião Zocolo ◽  
Glauco Pilon dos Santos ◽  
Josiane Vendemiatti ◽  
Francine Inforçato Vacchi ◽  
Gisela de Aragão Umbuzeiro ◽  
...  

Planta Medica ◽  
2012 ◽  
Vol 78 (11) ◽  
Author(s):  
N Fabre ◽  
E Deharo ◽  
HL Le ◽  
C Girardi ◽  
A Valentin ◽  
...  

2017 ◽  
Author(s):  
Tales Carvalho-Resende

The Environmental Water Stress in Transboundary River Basins indicator focuses on the water quantity aspect and considers hydrological alterations from monthly dynamics of the natural flow regime due to anthropogenic water uses and dam operations. For more information, visit: http://twap-rivers.org/ Basin Stress Surface water Transboundary


2000 ◽  
Vol 42 (3-4) ◽  
pp. 115-123 ◽  
Author(s):  
R. Shoji ◽  
A. Sakoda ◽  
Y. Sakai ◽  
M. Suzuki

The quality of environmental waters such as rivers is often deteriorated by various kinds of trace and unidentified chemicals despite the recent development of sewage systems and wastewater treatment technologies. In addition to contamination by particular toxicants, complex toxicity due to multi-component chemicals could be much more serious. The environmental situation in bodies of water in Japan led us to apply bioassays for monitoring the water quality of environmental waters in order to express the direct and potential toxicity to human beings and ecosystems rather than determinating concentrations of particular chemicals. However, problems arose from the fact that bioassays for pharmaceutical purposes generally required complicated, time-consuming, expert procedures. Also, a methodology for feedback of the resultant toxicity data to water environment management has not been established yet. To this end, we developed a novel bioassay based on the low-density lipoprotein (LDL) uptake activity of human hepatoblastoma cells. The assay enabled us to directly detect the toxicity of environmental waters within 4 hours of exposure. This is a significantly quick and easy procedure as compared to that of conventional bioassays. The toxicity data for 255 selected chemicals and environmental waters obtained by this method were organized by a mathematical equation in order to make those data much more effectively and practically useful to the management of environmental waters. Our methodology represents a promising example of applying bioassays to monitor environmental water quality and generating potential solutions to the toxicity problems encountered.


2012 ◽  
Vol 66 (5) ◽  
pp. 1103-1109 ◽  
Author(s):  
Zenghu Qin ◽  
Mingwei Tong ◽  
Lin Kun

Due to the surface water in the upper reaches of Yangtze River in China containing large amounts of silt and algae, high content of microorganisms and suspended solids, the water in Yangtze River cannot be used for cooling a heat pump directly. In this paper, the possibility of using Yangtze River, which goes through Chongqing, a city in southwest China, as a heat source–sink was investigated. Water temperature and quality of the Yangtze River in the Chongqing area were analyzed and the performance of water source heat pump units in different sediment concentrations, turbidity and algae material conditions were tested experimentally, and the water quality standards, in particular surface water conditions, in the Yangtze River region that adapt to energy-efficient heat pumps were also proposed. The experimental results show that the coefficient of performance heat pump falls by 3.73% to the greatest extent, and the fouling resistance of cooling water in the heat exchanger increases up to 25.6% in different water conditions. When the sediment concentration and the turbidity in the river water are no more than 100 g/m3 and 50 NTU respectively, the performance of the heat pump is better, which can be used as a suitable river water quality standard for river water source heat pumps.


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