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Keywords = (2-thio)barbiturates

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15 pages, 1866 KiB  
Article
Electron Spin Resonance Spectroscopy Suitability for Investigating the Oxidative Stability of Non-Alcoholic Beers
by Maria Cristina Porcu and Daniele Sanna
Oxygen 2025, 5(3), 14; https://doi.org/10.3390/oxygen5030014 - 16 Jul 2025
Viewed by 190
Abstract
Seven lager beers and seven non-alcoholic counterparts, marketed by the same producers, were analyzed for their total phenolic content (TPC), radical scavenging activity (RSA) towards the DPPH radical and ThioBarbituric Index (TBI). All beers were also subjected to spin trapping experiments at 60 [...] Read more.
Seven lager beers and seven non-alcoholic counterparts, marketed by the same producers, were analyzed for their total phenolic content (TPC), radical scavenging activity (RSA) towards the DPPH radical and ThioBarbituric Index (TBI). All beers were also subjected to spin trapping experiments at 60 °C in the presence of PBN. To our knowledge, this is the first time that non-alcoholic beers (NABs) have been subjected to spin trapping experiments coupled with Electron Spin Resonance (ESR) spectroscopy. The evolution of the intensity of the PBN radical adducts during the first 150 min was represented graphically and the intensity at 150 min (I150) and the area under the curve (AUC), were measured. The I150 and the AUC of lagers and NABs are significantly different, whereas the TPC, the EC50 of the DPPH assay, and the TBI of the two groups are superimposed. A relationship, previously proposed by us, to correlate ESR spectroscopy parameters with others obtained from UV-Vis spectrophotometry, was also applied, demonstrating its practicability. Multivariate analysis shows that clustering in two separate groups occurs only if I150 and AUC are included in the model. Based on these results, ESR spectroscopy can be applied to study the oxidative stability of NABs. Full article
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18 pages, 3489 KiB  
Article
Slow and Fast-Growing Chickens Use Different Antioxidant Pathways to Maintain Their Redox Balance during Postnatal Growth
by Edouard Coudert, Elisabeth Baéza, Pascal Chartrin, Justine Jimenez, Estelle Cailleau-Audouin, Thierry Bordeau and Cécile Berri
Animals 2023, 13(7), 1160; https://doi.org/10.3390/ani13071160 - 25 Mar 2023
Cited by 4 | Viewed by 1862
Abstract
The evolution of parameters known to be relevant indicators of energy status, oxidative stress, and antioxidant defense in chickens was followed. These parameters were measured weekly from 1 to 42 days in plasma and/or muscles and liver of two strains differing in growth [...] Read more.
The evolution of parameters known to be relevant indicators of energy status, oxidative stress, and antioxidant defense in chickens was followed. These parameters were measured weekly from 1 to 42 days in plasma and/or muscles and liver of two strains differing in growth rate. At 1-day old, in plasma, slow-growing (SG) chicks were characterized by a high total antioxidant status (TAS), probably related to higher superoxide dismutase (SOD) activity and uric acid levels compared to fast-growing (FG) chicks whereas the lipid peroxidation levels were higher in the liver and muscles of SG day-old chicks. Irrespective of the genotype, the plasma glutathione reductase (GR) and peroxidase (GPx) activities and levels of hydroperoxides and α- and γ-tocopherols decreased rapidly post-hatch. In the muscles, lipid peroxidation also decreased rapidly after hatching as well as catalase, GR, and GPx activities, while the SOD activity increased. In the liver, the TAS was relatively stable the first week after hatching while the value of thio-barbituric acid reactive substances (TBARS) and GR activity increased and GPx and catalase activities decreased. Our study revealed the strain specificities regarding the antioxidant systems used to maintain their redox balance over the life course. Nevertheless, the age had a much higher impact than strain on the antioxidant ability of the chickens. Full article
(This article belongs to the Section Animal Physiology)
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20 pages, 2941 KiB  
Article
Physical and Oxidative Water-in-Oil Emulsion Stability by the Addition of Liposomes from Shrimp Waste Oil with Antioxidant and Anti-Inflammatory Properties
by Carolina Pascual-Silva, Ailén Alemán, María Elvira López-Caballero, María Pilar Montero and María del Carmen Gómez-Guillén
Antioxidants 2022, 11(11), 2236; https://doi.org/10.3390/antiox11112236 - 13 Nov 2022
Cited by 6 | Viewed by 2870
Abstract
Liposomes made of partially purified phospholipids (PL) from Argentine red shrimp waste oil were loaded with two antioxidant lipid co-extracts (hexane-soluble, Hx and acetone-soluble, Ac) to provide a higher content of omega-3 fatty acids. The physical properties of the liposomes were characterized by [...] Read more.
Liposomes made of partially purified phospholipids (PL) from Argentine red shrimp waste oil were loaded with two antioxidant lipid co-extracts (hexane-soluble, Hx and acetone-soluble, Ac) to provide a higher content of omega-3 fatty acids. The physical properties of the liposomes were characterized by Transmission Electron Microscopy (TEM), Dynamic Light Scattering (DLS) and Differential Scanning Calorimetry (DSC). The antioxidant and anti-inflammatory activity of the lipid extracts and liposomal suspensions were evaluated in terms of Superoxide and ABTS radical scavenging capacities and TNF-α inhibition. Uni-lamellar spherical liposomes (z-average ≈ 145 nm) with strong negative ζ potential (≈ −67 mV) were obtained in all cases. The high content of neutral lipids in the Hx extract caused structural changes in the bilayer membrane and decreased entrapment efficiency regarding astaxanthin and EPA + DHA contents. The liposomes loaded with the Hx/Ac extracts showed higher antioxidant and anti-inflammatory activity compared with empty liposomes. The liposomal dispersions improved the physical and oxidative stability of water-in-oil emulsions as compared with the PL extract, inducing pronounced close packing of water droplets. The liposomes decreased hydroperoxide formation in freshly made emulsions and prevented thio-barbituric acid-reactive substances (TBARS) accumulation during chilled storage. Liposomes from shrimp waste could be valuable nanocarriers and stabilizers in functional food emulsions. Full article
(This article belongs to the Special Issue Lipid Oxidation in Food and Antioxidant Strategies)
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15 pages, 3171 KiB  
Article
Comparing C2=O and C2=S Barbiturates: Different Hydrogen-Bonding Patterns of Thiobarbiturates in Solution and the Solid State
by Chenming Li, Philipp Hilgeroth, Nazmul Hasan, Dieter Ströhl, Jörg Kressler and Wolfgang H. Binder
Int. J. Mol. Sci. 2021, 22(23), 12679; https://doi.org/10.3390/ijms222312679 - 24 Nov 2021
Cited by 8 | Viewed by 3121
Abstract
Carbonyl-centered hydrogen bonds with various strength and geometries are often exploited in materials to embed dynamic and adaptive properties, with the use of thiocarbonyl groups as hydrogen-bonding acceptors remaining only scarcely investigated. We herein report a comparative study of C2=O and C2=S barbiturates [...] Read more.
Carbonyl-centered hydrogen bonds with various strength and geometries are often exploited in materials to embed dynamic and adaptive properties, with the use of thiocarbonyl groups as hydrogen-bonding acceptors remaining only scarcely investigated. We herein report a comparative study of C2=O and C2=S barbiturates in view of their differing hydrogen bonds, using the 5,5-disubstituted barbiturate B and the thiobarbiturate TB as model compounds. Owing to the different hydrogen-bonding strength and geometries of C2=O vs. C2=S, we postulate the formation of different hydrogen-bonding patterns in C2=S in comparison to the C2=O in conventional barbiturates. To study differences in their association in solution, we conducted concentration- and temperature-dependent NMR experiments to compare their association constants, Gibbs free energy of association ∆Gassn., and the coalescence behavior of the N-H‧‧‧S=C bonded assemblies. In Langmuir films, the introduction of C2=S suppressed 2D crystallization when comparing B and TB using Brewster angle microscopy, also revealing a significant deviation in morphology. When embedded into a hydrophobic polymer such as polyisobutylene, a largely different rheological behavior was observed for the barbiturate-bearing PB compared to the thiobarbiturate-bearing PTB polymers, indicative of a stronger hydrogen bonding in the thioanalogue PTB. We therefore prove that H-bonds, when affixed to a polymer, here the thiobarbiturate moieties in PTB, can reinforce the nonpolar PIB matrix even better, thus indicating the formation of stronger H-bonds among the thiobarbiturates in polymers in contrast to the effects observed in solution. Full article
(This article belongs to the Special Issue Supramolecular Materials)
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16 pages, 683 KiB  
Article
Evaluation of Lipid Oxidation, Volatile Compounds and Vibrational Spectroscopy of Silver Carp (Hypophthalmichthys molitrix) during Ice Storage as Related to the Quality of Its Washed Mince
by Sasinee Kunyaboon, Kanjana Thumanu, Jae W. Park, Chompoonuch Khongla and Jirawat Yongsawatdigul
Foods 2021, 10(3), 495; https://doi.org/10.3390/foods10030495 - 25 Feb 2021
Cited by 44 | Viewed by 4298
Abstract
Changes in the lipid oxidation of silver carp (Hypophthalmichthys molitrix) stored in ice for 14 days and that of its respective washed mince were evaluated. Total lipid, phospholipid, polyunsaturated fatty acid (PUFA) and monounsaturated fatty acid (MUFA) contents of the skin, [...] Read more.
Changes in the lipid oxidation of silver carp (Hypophthalmichthys molitrix) stored in ice for 14 days and that of its respective washed mince were evaluated. Total lipid, phospholipid, polyunsaturated fatty acid (PUFA) and monounsaturated fatty acid (MUFA) contents of the skin, belly flap and mince decreased as the storage time in ice increased. The washing process decreased the lipid contents but concentrated their phospholipid counterparts. The fish belly flap exhibited the highest thio-barbituric acid reactive substances (TBARS) value, while the mince had the lowest. 1-Hexanol, 1-octen-3-ol, and 1-hexanal were key volatile compounds detected in the belly flaps of fish stored for 7–14 days. Hexanal was the only major volatile compound found in washed mince prepared from fish stored for an extended period in ice, but in a much lower amount compared with that in the belly flap. FTIR (Fourier transform infra-red) spectra revealed a decrease in the number of cis double bonds, methylene groups and phosphate groups in lipids extracted from fish stored in ice for 7–14 days as compared with those extracted from fresh fish. Principle component analysis (PCA) revealed that the FT-Raman band at 1747 cm−1 could be a potential marker for tracking the degree of lipid oxidation in the belly flap of silver carp stored in ice. In addition, IR bands indicating phosphate group (925, 825 cm−1) in oil extracted from washed mince were correlated with the extent of the lipid oxidation of the raw material. Full article
(This article belongs to the Special Issue New Insights into Lipid Oxidation in Foods)
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13 pages, 5916 KiB  
Article
Enamine Barbiturates and Thiobarbiturates as a New Class of Bacterial Urease Inhibitors
by M. Ali, Assem Barakat, Ayman El-Faham, Abdullah Mohammed Al-Majid, Sammer Yousuf, Sajda Ashraf, Zaheer Ul-Haq, M. Iqbal Choudhary, Beatriz G. de la Torre and Fernando Albericio
Appl. Sci. 2020, 10(10), 3523; https://doi.org/10.3390/app10103523 - 20 May 2020
Cited by 8 | Viewed by 3805
Abstract
Urease is a therapeutic target associated with several important diseases and health problems. Based on our previous work on the inhibition of glucosidase and other enzymes and exploiting the privileged structure assigned to the (thio)barbiturate (pyrimidine) scaffold, here we tested the capacity of [...] Read more.
Urease is a therapeutic target associated with several important diseases and health problems. Based on our previous work on the inhibition of glucosidase and other enzymes and exploiting the privileged structure assigned to the (thio)barbiturate (pyrimidine) scaffold, here we tested the capacity of two (thio)barbiturate-based compound collections to inhibit urease. Several compounds showed more activity than acetohydroxamic acid as a standard tested compound. In addition, by means of a conformational study and using the Density Functional Theory (DFT) method, we identified energetically low-lying conformers. Finally, we undertook a docking study to explore the binding mechanism of these new pyrimidine derivatives as urease inhibitors. Full article
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15 pages, 3609 KiB  
Article
A Biochemical Approach to Detect Oxidative Stress in Infertile Women Undergoing Assisted Reproductive Technology Procedures
by Matteo Becatti, Rossella Fucci, Amanda Mannucci, Victoria Barygina, Marco Mugnaini, Luciana Criscuoli, Claudia Giachini, Francesco Bertocci, Rita Picone, Giacomo Emmi, Paolo Evangelisti, Francesca Rizzello, Cinzia Cozzi, Niccolò Taddei, Claudia Fiorillo and Maria Elisabetta Coccia
Int. J. Mol. Sci. 2018, 19(2), 592; https://doi.org/10.3390/ijms19020592 - 16 Feb 2018
Cited by 50 | Viewed by 5458
Abstract
Oxidative stress plays a major role in critical biological processes in human reproduction. However, a reliable and biologically accurate indicator of this condition does not yet exist. On these bases, the aim of this study was to assess and compare the blood and [...] Read more.
Oxidative stress plays a major role in critical biological processes in human reproduction. However, a reliable and biologically accurate indicator of this condition does not yet exist. On these bases, the aim of this study was to assess and compare the blood and follicular fluid (FF) redox status of 45 infertile subjects (and 45 age-matched controls) undergoing in vitro fertilization (IVF), and explore possible relationships between the assessed redox parameters and IVF outcomes. Reactive Oxygen Species (ROS) production, assessed by flow cytometry analysis in blood leukocytes and granulosa cells, significantly increased (p < 0.05) in infertile patients. Also, oxidative stress markers—ThioBarbituric Acid-Reactive Substances (TBARS) as an index of lipid peroxidation, and Oxygen Radical Absorbance Capacity (ORAC) to account for total antioxidant capacity, both assayed by fluorometric procedures—in blood and FF were significantly (p < 0.001) modified in infertile patients compared to the control group. Moreover, a significant correlation between blood redox markers and FF redox markers was evident. An ORAC/TBARS ratio, defined as the redox index (RI), was obtained in the plasma and FF of the patients and controls. In the patients, the plasma RI was about 3.4-fold (p < 0.0001) lower than the control, and the FF RI was about six-fold (p < 0.0001) lower than the control. Interestingly, both the plasma RI and FF RI results were significantly correlated (p < 0.05) to the considered outcome parameters (metaphase II, fertilization rate, and ongoing pregnancies). Given the reported findings, a strict monitoring of redox parameters in assisted reproductive techniques and infertility management is recommended. Full article
(This article belongs to the Section Molecular Pathology, Diagnostics, and Therapeutics)
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12 pages, 351 KiB  
Article
Radical-Scavenging Activity of Thiols, Thiobarbituric Acid Derivatives and Phenolic Antioxidants Determined Using the Induction Period Method for Radical Polymerization of Methyl Methacrylate
by Yoshinori Kadoma and Seiichiro Fujisawa
Polymers 2012, 4(2), 1025-1036; https://doi.org/10.3390/polym4021025 - 16 Apr 2012
Cited by 15 | Viewed by 8755
Abstract
The radical-scavenging activities of two thiols, eight (thio)barbituric acid derivatives and six chain-breaking phenolic antioxidants were investigated using the induction period method for polymerization of methyl methacrylate (MMA) initiated by thermal decomposition of 2,2’-azobisisobutyronitrile (AIBN) and monitored by differential scanning calorimetry (DSC). The [...] Read more.
The radical-scavenging activities of two thiols, eight (thio)barbituric acid derivatives and six chain-breaking phenolic antioxidants were investigated using the induction period method for polymerization of methyl methacrylate (MMA) initiated by thermal decomposition of 2,2’-azobisisobutyronitrile (AIBN) and monitored by differential scanning calorimetry (DSC). The induction period (IP) for the thiols 2-mercaptoethanol (ME) and 2-mercapto-1-methylimidazole (MMI) was about half that for phenolic antioxidants. Except for the potent inhibitor 5,5-dimethyl-2-thiobarbituric acid (3), the IP for thiobarbituric acid derivatives was about one tenth of that for phenolic antioxidants. The IP for 1,3,5-trimethyl-2-thiobarbituric acid (1) and 5-allyl-1, 3-dimethyl-2-thiobarbituric acid (7) was less than that of the control, possibly due to inhibition by a small amount of atmospheric oxygen in the DSC container. The ratio of the chain inhibition to that of chain propagation (CI/CP) for the thiols and thiobarbituric acid compounds except for 1, 3 and 7 was about 10 times greater or greater than that for phenolic compounds. A kinetic chain length (KCL) about 10% greater than that of the control was observed for 1, suggesting that 1 had chain transfer reactivity in the polymerization of MMA. The average molecular weight of polymers formed from thiobarbituric acid derivatives is discussed. Full article
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