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Keywords = hydroxymethylation

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19 pages, 5641 KB  
Article
One-Pot Preparation of Easily Dispersible Hexagonal Mg(OH)2 Modified with THPS and Its Flame-Retardant EVA Copolymer
by Xia Liu, Haihui Xu and Jinyang Chen
Materials 2025, 18(21), 4847; https://doi.org/10.3390/ma18214847 - 23 Oct 2025
Viewed by 259
Abstract
As an eco-friendly flame-retardant additive, magnesium hydroxide (MH) is widely employed in low-smoking, halogen-free polymer materials due to its environmentally benign nature. In order to enhance flame retardancy performance, the modified MH was modified with tetrakis(hydroxymethyl)phosphonium sulfate (THPS) by a one-pot hydrothermal method. [...] Read more.
As an eco-friendly flame-retardant additive, magnesium hydroxide (MH) is widely employed in low-smoking, halogen-free polymer materials due to its environmentally benign nature. In order to enhance flame retardancy performance, the modified MH was modified with tetrakis(hydroxymethyl)phosphonium sulfate (THPS) by a one-pot hydrothermal method. The resulting morphology was characterized using scanning electron microscopy (SEM), and it shows the dispersion of nanometer particles and almost no aggregation. The X-ray photoelectron spectroscopy (XPS) along with Raman spectroscopy show that the THPS is connected with the Mg(OH)2 by chemical bond. The sample was incorporated into ethylene–vinyl acetate (EVA) to evaluate the flame retardancy was assessed via limiting oxygen index (LOI) and vertical burning tests (UL-94). The results show that THPS modified MH effectively enhanced the flame retardancy, achieving a V-0 rating and an LOI value of 31.3%. In addition, the composites retain good mechanical integrity. The thermal analysis with TGA and DTG shows the formation of the MgO decomposition product, along with water vapor and phosphorus-containing radicals released by modified MH in the combustion process, forming a strong flame-retardant protective layer. In addition, the maximum smoke density of EVA/MHP-3 composite was 155.4, lower than 411.3 for EVA/MH, with a 62.2% reduction in total smoke production. The result shows that THPS is effective for improving the flame-retardant efficiency of inorganic metal hydroxide in polymer composites. Full article
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25 pages, 5748 KB  
Article
Caffeic Acid Inhibits Degranulation, Cytokine Secretions, and IP3 Receptor 2 Gene Expression in Compound 48/80-Stimulated Mouse P815 Mast Cells
by Kai-Chi Chang and Jin-Yuarn Lin
Int. J. Mol. Sci. 2025, 26(20), 10086; https://doi.org/10.3390/ijms262010086 - 16 Oct 2025
Viewed by 266
Abstract
Caffeic acid (CA), 3-O-caffeoylquinic acid (3-CQA), and 5-O-caffeoylquinic acid (5-CQA) were subjected to treating stimulated mouse P815 mast cells to unravel their antiallergic potential. β-Hexosaminidase release, appearance, morphology change, cytokine secretions, and degranulation-related pathway gene expressions, including Mas-related G [...] Read more.
Caffeic acid (CA), 3-O-caffeoylquinic acid (3-CQA), and 5-O-caffeoylquinic acid (5-CQA) were subjected to treating stimulated mouse P815 mast cells to unravel their antiallergic potential. β-Hexosaminidase release, appearance, morphology change, cytokine secretions, and degranulation-related pathway gene expressions, including Mas-related G protein-coupled receptor, member B2 (MRGP receptor B2), and inositol 1,4,5-triphosphate receptor 2 (IP3 receptor 2), in the stimulated mast cells were measured. An ELISA was used to determine the secreted cytokines. The relative gene expression folds were analyzed with reverse transcription real-time quantitative polymerase chain reaction. Correlations between gene expressions and different parameters were analyzed using the Pearson product–moment correlation coefficient (r). The results showed that CA had a superior effect than 3-CQA and 5-CQA on reducing β-hexosaminidase release, IL-4, and IL-6 cytokine secretions by the compound 48/80 (C48/80)- and 5-hydroxymethyl-2-furaldehyde (5-HMF)-stimulated mast cells. CA increased intact mast cell numbers but reduced granule releases, evidencing that CA may soothe activated mast cells. CA reduced IP3 receptor 2 gene expression. There were positive correlations between IP3 receptor 2 gene expression and IL-4 and IL-6 cytokine secretions. Our results conclude that CA might inhibit degranulation, IL-4 and IL-6 cytokine secretions, and IP3 receptor 2 gene expression in C48/80-stimulated mouse P815 mast cells. Full article
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23 pages, 948 KB  
Article
Impact of Hot Water Extraction on the Chemical Composition of Hemp (Cannabis sativa L.)
by Kamil Roman and Monika Marchwicka
Materials 2025, 18(19), 4576; https://doi.org/10.3390/ma18194576 - 2 Oct 2025
Viewed by 396
Abstract
An investigation of the effect of intense Hot Water Extraction (HWE) on the chemical properties and processability of shredded hemp stalks (Cannabis sativa L.) is presented in this study. The chemical composition of untreated hemp was compared to that of hemp subjected [...] Read more.
An investigation of the effect of intense Hot Water Extraction (HWE) on the chemical properties and processability of shredded hemp stalks (Cannabis sativa L.) is presented in this study. The chemical composition of untreated hemp was compared to that of hemp subjected to V and XV successive HWE cycles. This study investigated changes in selected chemical compounds, such as extractives, lignin, cellulose, ash, and monosaccharides such as glucose and xylose. Additionally, post-HWE liquids were analyzed. Lignin content was determined by the UV–VIS spectrophotometry method, whereas monosaccharides (glucose, xylose) and inhibitors (formic acid, acetic acid, levulinic acid, ethanol, 5-(hydroxymethyl)furfural, and furfural) were identified by HPLC. Extractives and ash were effectively removed by the HWE process, decreasing from 3.2 to 2.0% and from 3.9% to 2.7%, respectively. The reduction in acid-soluble lignin was an important finding, indicating a selective modification of the lignin matrix. By the end of V cycles, xylose content in the liquid phase significantly increased from 117.9% to 19.4%, indicating a reduction in hemicelluloses. The cellulose content of the solid material rose from 42.9% to 46.2% at the end of XV cycles. Full article
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17 pages, 304 KB  
Article
Influence of Freeze- and Spray Drying with Carrier Agents on Alkamides, Antioxidant Properties, and Process Contaminants in Echinacea purpurea Root Extract Powders
by Mariusz Kułaga, Klaudia Masztalerz, Jessica Brzezowska and Anna Michalska-Ciechanowska
Molecules 2025, 30(19), 3864; https://doi.org/10.3390/molecules30193864 - 24 Sep 2025
Viewed by 1265
Abstract
Echinacea purpurea (L.) Moench root is a rich source of alkamides and other bioactive compounds with potential health-promoting effects. This study aimed to evaluate the influence of drying technique and carrier type on alkamide content, antioxidant properties, and process contaminants in E. purpurea [...] Read more.
Echinacea purpurea (L.) Moench root is a rich source of alkamides and other bioactive compounds with potential health-promoting effects. This study aimed to evaluate the influence of drying technique and carrier type on alkamide content, antioxidant properties, and process contaminants in E. purpurea powders. Root extracts were subjected to freeze-drying or spray drying at air inlet temperatures of 150, 170, and 190 °C, with maltodextrin, pea protein isolate, or their blend used as carrier agents. The resulting powders were analyzed for physical and chemical properties, including alkamides concentration, total phenolics content, antioxidant capacity, free amino group levels, and markers of advanced Maillard reaction products. Spray-dried powders had a moisture content lower than 2.3%, compared with an average of 7.7% in freeze-dried samples. Spray drying at 150 and 170 °C combined with the maltodextrin–pea protein blend resulted in the highest alkamide levels, while total phenolics content and antioxidant capacity were retained at levels comparable to freeze-drying. Neither hydroxymethyl-L-furfural nor furfural was detected via HPLC in any sample. Overall, spray drying under the tested conditions represents a favorable alternative to freeze drying, yielding E. purpurea root extracts powders with higher alkamides content, similar antioxidant properties, and absence of process contaminants. Full article
(This article belongs to the Section Food Chemistry)
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17 pages, 3206 KB  
Article
Improvement of Quality of Sour Camel Milk by Extract of Sparassis crispa: Physicochemical Properties, Sensory Quality and Metabolic Changes
by Lina Zhao, Ruping Ma, Linyan Zhu, Jinzhi Wang, Rui Wang, Xiaojun Wu, Xiaoyan Liu, Xinhong Huang, Lianchao Zhang and Bin Liu
Foods 2025, 14(17), 3042; https://doi.org/10.3390/foods14173042 - 29 Aug 2025
Viewed by 685
Abstract
Sour camel milk, as a nutritious fermented dairy product, faces challenges in terms of quality stability. Sparassis crispa, due to its antioxidant and antibacterial properties, shows potential in improving food quality. This study aimed to investigate the effects of different active components [...] Read more.
Sour camel milk, as a nutritious fermented dairy product, faces challenges in terms of quality stability. Sparassis crispa, due to its antioxidant and antibacterial properties, shows potential in improving food quality. This study aimed to investigate the effects of different active components of Sparassis crispa on the quality of sour camel milk. The results indicated that Component I was the most effective Sparassis crispa component in enhancing the quality of sour camel milk. The components of Component I were identified as LysoPC(0_0_18_2(9Z,12Z)), LysoPC(18_1(11Z)_0_0), and N-(2-hydroxymethyl-3-chloro-4-hydroxyphenyl) anthranilic acid, among others. It increased the total viable count of lactic acid bacteria (LAB) and water-holding capacity (WHC) while improving the texture of sour camel milk. Metabolomics analysis revealed that the first component of sour camel milk (FCS) and Sparassis crispa sour camel milk (SS) have a high degree of similarity in the composition of flavor substances. The characteristic flavor metabolites included 2-amylfuran, isoamyl alcohol, 2-methylbutyraldehyde, and 2-ethyl-1-hexanol. Additionally, the supplementation of Component I increased the levels of metabolites such as amino acids, free fatty acids, organic acids, and carbohydrates, thereby contributing to the enhanced taste and nutritional quality of sour camel milk. This intervention also strengthened carbohydrate and amino acid metabolism in LAB. These findings provide a theoretical basis for utilizing Component I to improve the quality of sour camel milk. Full article
(This article belongs to the Section Dairy)
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18 pages, 1491 KB  
Article
GABAergic and α-Glucosidase-Inhibitory Potentials of Fractions and Isolated Xanthones from Hypericum revolutum Vahl subsp. revolutum
by Maria S. Chukwuma, Lorenza Bertaina, Sophia Khom, Chika I. Chukwuma, Pieter C. Zietsman, Anke Wilhelm and Susanna L. Bonnet
Molecules 2025, 30(17), 3530; https://doi.org/10.3390/molecules30173530 - 29 Aug 2025
Viewed by 700
Abstract
This study aimed to investigate the glycaemic control potential and modulation of GABA-induced chloride currents (IGABA) of H. revolutum and the possible bioactive xanthones. Fractions from the leaf and stem extracts (dichloromethane and methanol) were assessed for in vitro α-glucosidase-inhibitory potential [...] Read more.
This study aimed to investigate the glycaemic control potential and modulation of GABA-induced chloride currents (IGABA) of H. revolutum and the possible bioactive xanthones. Fractions from the leaf and stem extracts (dichloromethane and methanol) were assessed for in vitro α-glucosidase-inhibitory potential and their ability to modulate IGABA (GABAergic effect) through GABAA receptors heterologously expressed in Xenopus oocytes. Xanthones 4-hydroxy-2,3-dimethoxy-9H-xanthen-9-one (1), 3-hydroxy-2,4-dimethoxy-9H-xanthen-9-one (2) and trans-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-5-methoxy-2,3-dihydro-7H-[1,4]dioxino[2,3-c]xanthen-7-one (3) were isolated from the stem and tested in the GABAA receptors assay, but only 3 was assessed for α-glucosidase-inhibitory action. Compared to acarbose (IC50 = 6.16 µM), 3 showed a mild to moderate α-glucosidase-inhibitory activity (IC50 = 45.1 µM), which may be attributed to the absence of a hydroxyl group at its xanthone core. Isomeric compounds 1 and 2 significantly enhanced IGABA with similar efficacy, while 3 was inactive, which may be attributed to its notable structural difference (cyclic ether substitution) compared to compounds 1 and 2. H. revolutum stem contains xanthones with α-glucosidase-inhibitory potential, which also enhance IGABA and could be further studied as a medicinal plant for managing GABAA receptor-mediated mental disorders and/or diabetes. Full article
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17 pages, 1546 KB  
Article
Association of Prenatal Polycyclic Aromatic Hydrocarbons Exposure, DNA Hydroxymethylation, and Neurodevelopment at 0 and 2 Years of Age
by Jinyu Li, Xiaomin Cao, Chengjuan Liu, Lin Cheng, Qiao Niu and Jisheng Nie
Toxics 2025, 13(9), 726; https://doi.org/10.3390/toxics13090726 - 29 Aug 2025
Viewed by 844
Abstract
Maternal exposure to polycyclic aromatic hydrocarbons (PAHs) during pregnancy may have effects on the offspring epigenome. And the change in onset epigenome may be associated with children’s neurodevelopment. The current study investigated the relationship between 5-hydroxymethylcytosine (5-hmC) levels in cord blood and PAH [...] Read more.
Maternal exposure to polycyclic aromatic hydrocarbons (PAHs) during pregnancy may have effects on the offspring epigenome. And the change in onset epigenome may be associated with children’s neurodevelopment. The current study investigated the relationship between 5-hydroxymethylcytosine (5-hmC) levels in cord blood and PAH metabolites in maternal urine at delivery and children’s neurodevelopment at birth and at age 2. We enrolled 400 pregnant women and their newborns and collected their biological samples after obtaining written informed consent. Enzyme linked immunosorbent assay kits and Chromatin immunoprecipitation kits were used to assess the DNA hydroxymethylation level in cord blood. We observed that 1-hydroxypyrene (1-OHPyr) was inversely associated with gesell developmental scale scores, positively associated with global DNA 5-hmC levels, and associated with decreased 5-hmC levels of the brain-derived neurotrophic factor (BDNF) and methyl CpG binding protein 2 (MeCP2) gene promoter. In addition, the 5-hmC levels of the BDNF and MeCP2 gene promoters were associated with motor scores. The global DNA 5-hmC was inversely associated with motor scores. Mediation analysis showed mediation effects between 1-OHPyr and motor scores by 5-hmC. The global DNA 5-hmC and MeCP2 and BDNF gene promoter 5-hmC contributed 28.51%, 27.29%, and 18.98% of the effect on motor scores changes related to 1-OHPyr. The study results suggested that 5-hmC can be a potential mechanism between prenatal PAH exposure and children’s neurodevelopment at age 2 and provide a better understanding of the role of hydroxymethylation in neurodevelopment. Full article
(This article belongs to the Section Reproductive and Developmental Toxicity)
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22 pages, 1368 KB  
Article
Liquid-Phase Hydrogenation over a Cu/SiO2 Catalyst of 5-hydroximethylfurfural to 2,5-bis(hydroxymethyl)furan Used in Sustainable Production of Biopolymers: Kinetic Modeling
by Juan Zelin, Hernán Antonio Duarte, Alberto Julio Marchi and Camilo Ignacio Meyer
Sustain. Chem. 2025, 6(3), 22; https://doi.org/10.3390/suschem6030022 - 6 Aug 2025
Viewed by 963
Abstract
2,5-bis(hydroxymethy)lfuran (BHMF), a renewable compound with extensive industrial applications, can be obtained by selective hydrogenation of the C=O group of 5-hydroxymethylfurfural (HMF), a platform molecule derived from lignocellulosic biomass. In this work, we perform kinetic modeling of the selective liquid-phase hydrogenation of HMF [...] Read more.
2,5-bis(hydroxymethy)lfuran (BHMF), a renewable compound with extensive industrial applications, can be obtained by selective hydrogenation of the C=O group of 5-hydroxymethylfurfural (HMF), a platform molecule derived from lignocellulosic biomass. In this work, we perform kinetic modeling of the selective liquid-phase hydrogenation of HMF to BHMF over a Cu/SiO2 catalyst prepared by precipitation–deposition (PD) at a constant pH. Physicochemical characterization, using different techniques, confirms that the Cu/SiO2–PD catalyst is formed by copper metallic nanoparticles of 3–5 nm in size highly dispersed on the SiO2 surface. Before the kinetic study, the Cu/SiO2-PD catalyst was evaluated in three solvents: tetrahydrofuran (THF), 2-propanol (2-POH), and water. The pattern of catalytic activity and BHMF yield for the different solvents was THF > 2-POH > H2O. In addition, selectivity to BHF was the highest in THF. Thus, THF was chosen for further kinetic study. Several experiments were carried out by varying the initial HMF concentration (C0HMF) between 0.02 and 0.26 M and the hydrogen pressure (PH2) between 200 and 1500 kPa. In all experiments, BHMF selectivity was 97–99%. By pseudo-homogeneous modeling, an apparent reaction order with respect to HFM close to 1 was estimated for a C0HMF between 0.02 M and 0.065 M, while when higher than 0.065 M, the apparent reaction order changed to 0. The apparent reaction order with respect to H2 was nearly 0 when C0HMF = 0.13 M, while for C0HMF = 0.04 M, it was close to 1. The reaction orders estimated suggest that HMF is strongly absorbed on the catalyst surface, and thus total active site coverage is reached when the C0HMF is higher than 0.065 M. Several Langmuir–Hinshelwood–Hougen–Watson (LHHW) kinetic models were proposed, tested against experimental data, and statistically compared. The best fitting of the experimental data was obtained with an LHHW model that considered non-competitive H2 and HMF chemisorption and strong chemisorption of reactant and product molecules on copper metallic active sites. This model predicts both the catalytic performance of Cu/SiO2-PD and its deactivation during liquid-phase HMF hydrogenation. Full article
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16 pages, 2009 KB  
Article
Incorporation and Repair of Epigenetic Intermediates as Potential Chemotherapy Agents
by Jason L. Herring, Mark L. Sowers, James W. Conrad, Linda C. Hackfeld, Bruce Chang-Gu, Rahul Dilawari and Lawrence C. Sowers
Molecules 2025, 30(15), 3239; https://doi.org/10.3390/molecules30153239 - 1 Aug 2025
Viewed by 1275
Abstract
The incorporation of nucleoside analogs into DNA by polymerases, followed by their removal through base excision repair (BER), represents a promising strategy for cancer chemotherapy. In this study, we investigated the incorporation and cytotoxic effects of several nucleoside analogs—some of which are epigenetic [...] Read more.
The incorporation of nucleoside analogs into DNA by polymerases, followed by their removal through base excision repair (BER), represents a promising strategy for cancer chemotherapy. In this study, we investigated the incorporation and cytotoxic effects of several nucleoside analogs—some of which are epigenetic reprogramming intermediates—in the U87 glioblastoma cell line. We found that two analogs, 5-hydroxymethyl-2′-deoxyuridine (5HmdU) and trifluorothymidine (TFT), are both cytotoxic and are efficiently incorporated into genomic DNA. In contrast, the 5-carboxy analogs—5-carboxy-2′-deoxyuridine (5CadU) and 5-carboxycytidine (5CadC)—showed no cytotoxicity and were not incorporated into DNA. Interestingly, 5-hydroxymethyl-2′-deoxycytidine (5HmdC) was cytotoxic but was not directly incorporated into DNA. Instead, it was deaminated into 5HmdU, which was then incorporated and likely responsible for the observed toxicity. 5HmdU is actively removed from DNA through the BER pathways. In contrast, TFT remains stably incorporated and is neither excised by BER nor does it hydrolyze into 5CadU—a known substrate for the DNA glycosylase SMUG1. We also found that N6-benzyladenosine (BzAdo), an inhibitor of the enzyme 2′-deoxynucleoside 5′-phosphate N-hydrolase (DNPH1), enhances the cytotoxicity of 5HmdU. However, the thymidine phosphorylase inhibitor tipiracil hydrochloride (TPI) does not increase the cytotoxic effect of TFT in U87 cells. Together, these findings highlight 5HmdU and TFT as promising chemotherapeutic agents for glioblastoma, each with distinct mechanisms of action and cellular processing. Full article
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23 pages, 3376 KB  
Article
Physicochemical and Instrumental Flavor Analysis of Plant-Based Drinks with Plant Powder Additions
by Joanna Kolniak-Ostek, Agnieszka Kita, Davide Giacalone, Laura Vázquez-Araújo, Luis Noguera-Artiaga, Jessica Brzezowska and Anna Michalska-Ciechanowska
Foods 2025, 14(15), 2593; https://doi.org/10.3390/foods14152593 - 24 Jul 2025
Viewed by 1132
Abstract
This study explored the use of fruit- and herb-based powders as fortifying agents in soy- and oat-based beverages. Developed using a New Product Development approach, the powders were derived from underutilized plants rich in bioactives but with limited sensory appeal. Formulations included powders [...] Read more.
This study explored the use of fruit- and herb-based powders as fortifying agents in soy- and oat-based beverages. Developed using a New Product Development approach, the powders were derived from underutilized plants rich in bioactives but with limited sensory appeal. Formulations included powders from both widely available fruits, such as apple and pear, chosen for their accessibility and economic relevance, and less commonly consumed fruits, such as Japanese quince, rosehip, and rhubarb, which are often discarded due to sour or astringent flavors. Processing these into powders helped mask undesirable sensory traits and enabled incorporation into beverage matrices. Physicochemical analyses confirmed their technological suitability, while high polyphenol content indicated potential health benefits. Importantly, no process contaminants (furfural, 5-hydroxymethyl-L-furfural, and acrylamide) were detected, supporting the powders’ safety for food use. The integrated application of an electronic tongue and nose enabled objective profiling of taste and aroma. The electronic tongue distinguished taste profiles across formulations, revealing matrix-dependent effects and interactions, particularly with trehalose, that influenced sweetness and bitterness. The electronic nose provided consistent aroma differentiation. Overall, the results highlight the potential of these underutilized plant powders as multifunctional ingredients in plant-based beverage development. They support product innovation aligned with consumer expectations for natural, health-promoting foods. Future work will include sensory validation with consumer panels. Full article
(This article belongs to the Section Nutraceuticals, Functional Foods, and Novel Foods)
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17 pages, 2219 KB  
Article
Oil Spill Recovery of Petroleum-Derived Fuels Using a Bio-Based Flexible Polyurethane Foam
by Fabrizio Olivito, Zul Ilham, Wan Abd Al Qadr Imad Wan-Mohtar, Goldie Oza, Antonio Procopio and Monica Nardi
Polymers 2025, 17(14), 1959; https://doi.org/10.3390/polym17141959 - 17 Jul 2025
Cited by 1 | Viewed by 759
Abstract
In this study, we tested a flexible polyurethane (PU) foam, synthesized from bio-based components, for the removal of petroleum-derived fuels from water samples. The PU was synthesized via the prepolymer method through the reaction of PEG 400 with L-lysine ethyl ester diisocyanate (L-LDI), [...] Read more.
In this study, we tested a flexible polyurethane (PU) foam, synthesized from bio-based components, for the removal of petroleum-derived fuels from water samples. The PU was synthesized via the prepolymer method through the reaction of PEG 400 with L-lysine ethyl ester diisocyanate (L-LDI), followed by chain extension with 2,5-bis(hydroxymethyl)furan (BHMF), a renewable platform molecule derived from carbohydrates. Freshwater and seawater samples were artificially contaminated with commercial diesel, gasoline, and kerosene. Batch adsorption experiments revealed that the total sorption capacity (S, g/g) of the PU was slightly higher for diesel in both water types, with values of 67 g/g in freshwater and 70 g/g in seawater. Sorption kinetic analysis indicated that the process follows a pseudo-second-order kinetic model, suggesting strong chemical interactions. Equilibrium data were fitted using Langmuir and Freundlich isotherm models, with the best fit achieved by the Langmuir model, supporting a monolayer adsorption mechanism on homogeneous surfaces. The PU foam can be regenerated up to 50 times by centrifugation, maintaining excellent performance. This study demonstrates a promising application of this sustainable and bio-based polyurethane foam for environmental remediation. Full article
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23 pages, 3606 KB  
Article
Complementary Synthesis of Anti- and Syn-Hydroxymethyl 1,3-Diols via Regioselective Ring Opening of TIPS-Protected 2,3-Epoxy Alcohols: Toward Polypropionate Fragments
by Raúl R. Rodríguez-Berríos and José A. Prieto
Organics 2025, 6(3), 29; https://doi.org/10.3390/org6030029 - 10 Jul 2025
Viewed by 1558
Abstract
Hydroxymethyl 1,3-diol motifs are common structural motifs in natural products, particularly in polypropionates with important therapeutic potential. However, general and complementary methods for their regio- and diastereoselective synthesis remain limited. In this study, we expanded a second-generation epoxide-based methodology involving the regioselective cleavage [...] Read more.
Hydroxymethyl 1,3-diol motifs are common structural motifs in natural products, particularly in polypropionates with important therapeutic potential. However, general and complementary methods for their regio- and diastereoselective synthesis remain limited. In this study, we expanded a second-generation epoxide-based methodology involving the regioselective cleavage of TIPS-monoprotected cis- and trans-2,3-epoxy alcohols using alkenyl Grignard reagents. Regioselective ring opening of cis-epoxides provided anti-1,3-diols, while trans-epoxides afforded the corresponding syn-1,3-diols. The use of cis-propenylmagnesium bromide and vinyl Grignard reagents enabled direct access to cis- and terminal homoallylic 1,3-diols, respectively, with moderate to good yields (46–88%) and excellent regioselectivities (95:5). In contrast, reactions with trans-propenyl Grignard reagent led to partial alkene isomerization, limiting their synthetic utility. To address this, a complementary two-step approach employing propynyl alanate addition followed by sodium/ammonia reduction was incorporated, providing access to trans-homoallylic 1,3-diols with high diastereoselectivity. All 1,3-diols were characterized by NMR spectroscopy, confirming regioselective epoxide opening. These combined strategies offer a practical and modular platform for the synthesis of syn- and anti-hydroxymethylated 1,3-diols and their application to the construction of polypropionate-type fragments, supporting future efforts in the total synthesis of polyketide natural products. Full article
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24 pages, 3140 KB  
Article
Physicochemical and Sensory Evaluation of Romanian Monofloral Honeys from Different Supply Chains
by Elena Daniela Bratosin, Delia Mirela Tit, Manuela Bianca Pasca, Anamaria Lavinia Purza, Gabriela Bungau, Ruxandra Cristina Marin, Andrei Flavius Radu and Daniela Gitea
Foods 2025, 14(13), 2372; https://doi.org/10.3390/foods14132372 - 4 Jul 2025
Cited by 3 | Viewed by 1070
Abstract
Honey quality and authenticity are influenced by floral origin, processing, and storage, with implications for composition and sensory appeal. This study offers a comparative assessment of eight monofloral honey samples, representing five botanical varieties: acacia, linden, rapeseed, lavender, and thyme. For acacia, linden, [...] Read more.
Honey quality and authenticity are influenced by floral origin, processing, and storage, with implications for composition and sensory appeal. This study offers a comparative assessment of eight monofloral honey samples, representing five botanical varieties: acacia, linden, rapeseed, lavender, and thyme. For acacia, linden, and rapeseed, both producer-sourced and commercial honeys were analyzed, while lavender and thyme samples were available only from local beekeepers. The botanical origin of each sample was confirmed using morphological markers of pollen grains. Physicochemical characterization included acidity, pH, moisture content, refractive index, hydroxymethyl furfural (HMF), proline concentration, and carbohydrate profiling by HPLC-RID. Acacia honey exhibited the lowest acidity and HMF levels, alongside the highest fructose/glucose (F/G) ratios, indicating superior freshness, lower crystallization risk, and a sweeter flavor profile. In contrast, rapeseed honey showed elevated glucose levels and the lowest F/G ratio, confirming its tendency to crystallize rapidly. All samples recorded proline concentrations well above the quality threshold (180 mg/kg), supporting their authenticity and proper maturation. The estimated glycemic index (eGI) varied between 43.91 and 62.68 and was strongly inversely correlated with the F/G ratio (r = −0.98, p < 0.001). Sensory evaluation highlighted acacia honey from producers as the most appreciated across visual, tactile, and flavor attributes. Correlation analyses further revealed consistent links between sugar composition and both physical and sensory properties. Overall, the findings reinforce the value of integrated analytical and sensory profiling in assessing honey quality and authenticity. Full article
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20 pages, 1185 KB  
Article
Optimization of Fermentation Parameters for Enhanced Bioethanol Production by Multistress-Tolerant Saccharomycodes ludwigii APRE2 Using Undetoxified Sugarcane Bagasse Hydrolysate
by Preekamol Klanrit, Sudarat Thanonkeo, Warayutt Pilap, Jirawan Apiraksakorn, Khanittha Fiala, Ratanaporn Leesing, Mamoru Yamada and Pornthap Thanonkeo
Energies 2025, 18(13), 3428; https://doi.org/10.3390/en18133428 - 30 Jun 2025
Viewed by 712
Abstract
The presence of various inhibitory compounds in lignocellulosic hydrolysates poses a significant challenge for bioethanol production, requiring yeasts with exceptional multistress tolerance. This study introduces the novel application and demonstrates the robust performance of the nonconventional yeast Saccharomycodes ludwigii APRE2 for efficient bioethanol [...] Read more.
The presence of various inhibitory compounds in lignocellulosic hydrolysates poses a significant challenge for bioethanol production, requiring yeasts with exceptional multistress tolerance. This study introduces the novel application and demonstrates the robust performance of the nonconventional yeast Saccharomycodes ludwigii APRE2 for efficient bioethanol production directly from undetoxified sugarcane bagasse hydrolysate (SBH) at 37 °C. This approach critically eliminates the need for the costly detoxification pretreatments often required in industrial processes. Initial experiments confirmed S. ludwigii APRE2’s capability to ferment undetoxified SBH. To optimize fermentation efficiency, a central composite design (CCD) approach was implemented. This statistical method identified the following precise optimal parameters: sugar concentration (143.95 g/L), diammonium phosphate (4.99 g/L), pH (4.98), yeast extract (8.94 g/L), and magnesium sulfate (2.22 g/L). Under these optimized conditions, impressive results were achieved: a maximum ethanol concentration of 38.11 g/L, productivity of 1.59 g/L·h, and yield of 0.45 g/g. Notably, the ethanol productivity and theoretical yield achieved by S. ludwigii APRE2 using this inhibitor-rich, undetoxified SBH (containing acetic acid, formic acid, furfural, and 5-(hydroxymethyl)furfural) were superior to those previously reported for other ethanologenic yeasts under similar challenging conditions. This research establishes S. ludwigii APRE2 as a highly promising and industrially viable candidate for sustainable bioethanol production from lignocellulosic biomass, with its key novelty being its superior performance on undetoxified feedstocks, potentially reducing overall production costs. Full article
(This article belongs to the Special Issue Biomass and Waste-to-Energy for Sustainable Energy Production)
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Article
Discovery of Novel Phenolic Compounds from Eutypa lata Through OSMAC Approach: Structural Elucidation and Antibiotic Potential
by Ana Cotán, Inmaculada Izquierdo-Bueno, Abdellah Ezzanad, Laura Martín, Manuel Delgado, Isidro G. Collado and Cristina Pinedo-Rivilla
Int. J. Mol. Sci. 2025, 26(12), 5774; https://doi.org/10.3390/ijms26125774 - 16 Jun 2025
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Abstract
Among grapevine trunk diseases, Eutypa dieback, caused by the fungus Eutypa lata, is one of the most critical ones, due to its widespread infection in vineyards and the lack of effective treatments. This fungus is a vascular pathogen that enters grapevines through [...] Read more.
Among grapevine trunk diseases, Eutypa dieback, caused by the fungus Eutypa lata, is one of the most critical ones, due to its widespread infection in vineyards and the lack of effective treatments. This fungus is a vascular pathogen that enters grapevines through pruning wounds. The infection process is associated with phytotoxic metabolites produced by the fungus, and as such, the identification of new metabolites from different culture conditions and broths could provide valuable insights into the fungus’s enzymatic system and help its control. For the purposes of this study, the OSMAC (one strain, many compounds) approach was applied to investigate the secondary metabolism of E. lata strain 311 isolated from Vitis vinifera plants in Spain. A total of twenty metabolites were isolated, including five reported for the first time from E. lata and four that are newly identified compounds in the literature: eulatagalactoside A, (R)-2-(4′-hydroxy-3′-methylbut-1′-yn-1′-yl)-4-(hydroxymethyl)phenol, (S)-7-hydroxymethyl-3-methyl-2,3-dihydro-1-benzoxepin-3-ol, and (3aR,4S,5R,7aS)-4,5-dihydroxy-6-((R)-3′-methylbuta-1′,3′-dien-1′-ylidene)hexahydrobenzo[d][1,3]dioxol-2-one. These compounds were extracted from fermentation broths using silica gel column chromatography and high-performance liquid chromatography (HPLC). Their structures were elucidated through extensive 1D and 2D NMR spectroscopy, along with high-resolution electrospray ionization mass spectrometry (HRESIMS). Compounds were evaluated for phytotoxicity against Phaseolus vulgaris, with only eulatagalactoside A producing white spots after 48 h. Additionally, the antibacterial activity against Escherichia coli, Staphylococcus aureus, and Klebsiella pneumoniae of selected compounds was tested. The compounds (R)-2-(4′-hydroxy-3′-methylbut-1′-yn-1′-yl)-4-(hydroxymethyl)phenol and (S)-7-(hydroxymethyl)-3-methyl-2,3-dihydrobenzo[b]oxepin-3-ol showed the most significant antimicrobial activity against Gram-positive bacteria, inhibiting S. aureus by over 75%, with IC50 values of 511.4 µg/mL and 617.9 µg/mL, respectively. Full article
(This article belongs to the Special Issue Molecular Characterization of Plant–Microbe Interactions)
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