Molecules

17 pages, 2842 KiB

Open AccessReview

The Proteome Content of Blood Clots Observed Under Different Conditions: Successful Role in Predicting Clot Amyloid(ogenicity)

by Douglas B. Kell and Etheresia Pretorius

Molecules 2025, 30(3), 668; https://doi.org/10.3390/molecules30030668 (registering DOI) - 3 Feb 2025

Abstract

A recent analysis compared the proteome of (i) blood clots seen in two diseases—sepsis and long COVID—when blood was known to have clotted into an amyloid microclot form (as judged by staining with the fluorogenic amyloid stain thioflavin T) with (ii) that of [...] Read more.

A recent analysis compared the proteome of (i) blood clots seen in two diseases—sepsis and long COVID—when blood was known to have clotted into an amyloid microclot form (as judged by staining with the fluorogenic amyloid stain thioflavin T) with (ii) that of those non-amyloid clots considered to have formed normally. Such fibrinaloid microclots are also relatively resistant to fibrinolysis. The proteins that the amyloid microclots contained differed markedly both from the soluble proteome of typical plasma and that of normal clots, and also between the diseases studied (an acute syndrome in the form of sepsis in an ITU and a chronic disease represented by Long COVID). Many proteins in the amyloid microclots were low in concentration in plasma and were effectively accumulated into the fibres, whereas many other abundant plasma proteins were excluded. The proteins found in the microclots associated with the diseases also tended to be themselves amyloidogenic. We here ask effectively the inverse question. This is: can the clot proteome tell us whether the clots associated with a particular disease contained proteins that are observed uniquely (or are highly over-represented) in known amyloid clots relative to normal clots, and thus were in fact amyloid in nature? The answer is in the affirmative in a variety of major coagulopathies, viz., venous thromboembolism, pulmonary embolism, deep vein thrombosis, various cardiac issues, and ischaemic stroke. Galectin-3-binding protein and thrombospondin-1 seem to be especially widely associated with amyloid-type clots, and the latter has indeed been shown to be incorporated into growing fibrin fibres. These may consequently provide useful biomarkers with a mechanistic basis. Full article

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10 pages, 1946 KiB

Open AccessArticle

Synthesis and Characterization of Lignocellulose-Based Carbon Quantum Dots (CQDs) and Their Antimicrobial and Antioxidant Functionalities

by Wooseok Lee and Seonghyuk Ko

Molecules 2025, 30(3), 667; https://doi.org/10.3390/molecules30030667 (registering DOI) - 3 Feb 2025

Abstract

Carbon quantum dots (CQDs) have recently drawn enormous attention due to not only their unique chemical, biological, and optical properties but also because a variety of renewable biomasses are readily utilized as carbon sources in their synthesis. This study investigated the synthesis, characterization, [...] Read more.

Carbon quantum dots (CQDs) have recently drawn enormous attention due to not only their unique chemical, biological, and optical properties but also because a variety of renewable biomasses are readily utilized as carbon sources in their synthesis. This study investigated the synthesis, characterization, and functional evaluation of CQDs from unbleached mechanical pulp as a natural lignocellulosic resource. The CQDs were synthesized using a one-step hydrothermal synthesis with varying temperature, time, and pulp consistency. The resulting CQDs exhibit a spherical shape with a size distribution of 9.73 ± 0.82 nm and lattice parameters of 0.21 and 0.34 nm, indicating a graphite core. The photoluminescence spectra showed evident fluorescence characteristics, with an emission peak at 435 nm at an excitation wavelength of 370 nm. The as-prepared CQDs were also chemically composed of C=C and C=O bonds linked to the hydroxyl and carboxyl functional groups, which are typically found in lignocellulose-based CQDs. The CQDs demonstrated antibacterial activity exceeding 99.9% against E. coli at the lowest concentration of 0.75 mg/mL. Demonstrating its antioxidation property, the DPPH radical scavenging activity surpassed 90% with more than 40 µg/mL of the CQD solution. Full article

(This article belongs to the Special Issue Preparation, Characterization and Application of Biochemical Antimicrobial Materials and Compounds)

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24 pages, 6571 KiB

Open AccessReview

Oxazolo[5,4-d]pyrimidines as Anticancer Agents: A Comprehensive Review of the Literature Focusing on SAR Analysis

by Aleksandra Sochacka-Ćwikła and Marcin Mączyński

Molecules 2025, 30(3), 666; https://doi.org/10.3390/molecules30030666 (registering DOI) - 3 Feb 2025

Abstract

Oxazolo[5,4-d]pyrimidines have been found to exhibit a wide range of biological activities, including the inhibition of various enzymes and signaling pathways associated with carcinogenesis. The objective of this review is to demonstrate that the oxazolo[5,4-d]pyrimidine scaffold represents a valuable [...] Read more.

Oxazolo[5,4-d]pyrimidines have been found to exhibit a wide range of biological activities, including the inhibition of various enzymes and signaling pathways associated with carcinogenesis. The objective of this review is to demonstrate that the oxazolo[5,4-d]pyrimidine scaffold represents a valuable structure for the design of novel anticancer therapies. The article provides a comprehensive overview of the chemical structure and pharmacological properties of oxazolo[5,4-d]pyrimidine derivatives, drawing upon the literature and international patents from 1974 until the present. Notably, the review explores structure–activity relationships (SAR) with a view to enhancing the therapeutic efficacy of oxazolo[5,4-d]pyrimidines. Full article

(This article belongs to the Special Issue Design, Synthesis, and Analysis of Potential Drugs, 3rd Edition)

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39 pages, 6889 KiB

Open AccessReview

Insights into the Sources, Structure, and Action Mechanisms of Quinones on Diabetes: A Review

by Tingting Zhang, Mingyue Li, Jingyang Lu, Jia Wang, Min Zhang, Pharkphoom Panichayupakaranant and Haixia Chen

Molecules 2025, 30(3), 665; https://doi.org/10.3390/molecules30030665 (registering DOI) - 3 Feb 2025

Abstract

Quinones, one of the oldest organic compounds, are of increasing interest due to their abundant presence in a wide range of natural sources and their remarkable biological activity. These compounds occur naturally in green leafy vegetables, fruits, herbs, animal and marine sources, and [...] Read more.

Quinones, one of the oldest organic compounds, are of increasing interest due to their abundant presence in a wide range of natural sources and their remarkable biological activity. These compounds occur naturally in green leafy vegetables, fruits, herbs, animal and marine sources, and fermented products, and have demonstrated promising potential for use in health interventions, particularly in the prevention and management of type 2 diabetes (T2DM). This review aims to investigate the potential of quinones as a health intervention for T2DM from the multidimensional perspective of their sources, types, structure–activity relationship, glucose-lowering mechanism, toxicity reduction, and bioavailability enhancement. Emerging research highlights the hypoglycemic activities of quinones, mainly driven by their redox properties, which lead to covalent binding, and their structural substituent specificity, which leads to their non-covalent binding to biocomplexes. Quinones can improve insulin resistance and regulate glucose homeostasis by modulating mitochondrial function, inflammation, lipid profile, gastrointestinal absorption, and by acting as insulin mimetics. Meanwhile, increasing attention is being given to research focused on mitigating the toxicity of quinones during administration and enhancing their bioavailability. This review offers a critical foundation for the development of quinone-based health therapies and functional foods aimed at diabetes management. Full article

(This article belongs to the Topic Natural Bioactive Compounds as a Promising Approach to Mitigating Oxidative Stress)

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19 pages, 3728 KiB

Open AccessArticle

Exploring Bovine Serum Albumin (BSA) as a Facile Substrate for Testing of Osmolytes as Cosmetic Ingredients

by Giulia Sinesi, Lucia Salvioni, Elisabetta Ronchi, Elena Maria Gabriella Barbuzzi, Davide Prosperi, Miriam Colombo and Marco Davide Giustra

Molecules 2025, 30(3), 664; https://doi.org/10.3390/molecules30030664 (registering DOI) - 3 Feb 2025

Abstract

Osmolytes, cellular compounds that maintain osmotic balance and integrity, are gaining attention in cosmetics for their ability to modulate protein folding and stability. Their incorporation into hair and skin care products enhances hydration and strengthens cellular structures. As the cosmetic industry seeks innovative [...] Read more.

Osmolytes, cellular compounds that maintain osmotic balance and integrity, are gaining attention in cosmetics for their ability to modulate protein folding and stability. Their incorporation into hair and skin care products enhances hydration and strengthens cellular structures. As the cosmetic industry seeks innovative and effective ingredients, osmolytes remain promising candidates for further advancing technologies. This study evaluates the protective effects of four osmolytes—betaine, erythritol, glycine, and isopentyldiol—on bovine serum albumin (BSA), as a substrate, under stressors such as UV irradiation, extreme temperatures, pH changes, surfactants, and oxidative stress. Protein stability was assessed via fluorescence emission. Only betaine at 0.50% w/w provided significant protection under oxidative stress, while glycine was the most effective osmolyte under basic and acidic pH and UVC radiation. Betaine showed potential in mitigating cold-induced stress but increased stress under UVA radiation, highlighting its condition-specific effects. The study emphasizes the need for comprehensive screening and synergistic testing of osmolytes to optimize cosmetic formulations for diverse stressors. Among the tested osmolytes, glycine is a promising candidate for skin and hair care products, though further research is needed. These findings provide a rapid, cost-effective method to evaluate osmolytes’ potential, offering valuable insights for cosmetic formulation. Full article

(This article belongs to the Section Cross-Field Chemistry)

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15 pages, 2822 KiB

Open AccessArticle

Small Molecules from Medicinal Plant Iris tectorum as Histidine Kinase Inhibitor to Resensitize β-Lactam-Resistant Escherichia coli

by Youqi Ji, Yinhuan Wang, Zhangkai Xu, Danlei Chen, Zhendi Yu, Qingyi Shao, Xin Hong, Zishu Liu and Dongqing Cheng

Molecules 2025, 30(3), 663; https://doi.org/10.3390/molecules30030663 (registering DOI) - 3 Feb 2025

Abstract

Background: Due to the widespread use of broad-spectrum antibiotics, the problem of antibiotic resistance has become an increasingly serious global threat. One of the key mechanisms of Escherichia coli resistance to beta-lactam antibiotics is the production of beta-lactamase enzymes, which poses a dilemma [...] Read more.

Background: Due to the widespread use of broad-spectrum antibiotics, the problem of antibiotic resistance has become an increasingly serious global threat. One of the key mechanisms of Escherichia coli resistance to beta-lactam antibiotics is the production of beta-lactamase enzymes, which poses a dilemma for clinicians in selecting antibiotics when faced with resistant bacterial infections. However, research on the reversal of bacterial resistance is limited. Methods: This study involved the preparation of Iris tectorum extract and detection of its effects on antibiotics sensitivity, extended-spectrum beta-lactamase (ESBL) gene expression, and histidine kinase phosphorylation levels in β-lactam antibiotic-resistant Escherichia coli. Additionally, analyses of the active ingredients of Iris tectorum extract were conducted with a liquid chromatography–mass spectrometer, and the binding sites were predicted by molecular docking. Results: Iris tectorum extract could restore the sensitivity of Escherichia coli to beta-lactam antibiotics and reduce the expression levels of ESBL genes and histidine phosphorylation levels. The active ingredients of Iris tectorum extract may be irigenin and tectorigenin, and these two small molecules could bind to histidine kinase to inhibit phosphorylation. Conclusions: Iris tectorum extract may serve as an antibiotic adjuvant, restoring the sensitivity of antibiotic-resistant bacteria by inhibiting histidine kinase phosphorylation, thereby alleviating the problem of Escherichia coli resistance to β-lactam antibiotics. Full article

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15 pages, 1354 KiB

Open AccessArticle

Tocotrienols in Eleven Species of Hypericum Genus Leaves

by Danija Lazdiņa, Inga Mišina and Paweł Górnaś

Molecules 2025, 30(3), 662; https://doi.org/10.3390/molecules30030662 (registering DOI) - 2 Feb 2025

Abstract

Saint John’s worts or goatweeds are mostly perennial flowering plants in the Hypericaceae family, formerly under the Clusiaceae family. Teas and macerations of the plants are common in traditional medicines and modern depression and cancer therapies. The most notable bioactive compounds in Hypericum [...] Read more.

Saint John’s worts or goatweeds are mostly perennial flowering plants in the Hypericaceae family, formerly under the Clusiaceae family. Teas and macerations of the plants are common in traditional medicines and modern depression and cancer therapies. The most notable bioactive compounds in Hypericum are hyperforin and hypericin. While Hypericum contains a variety of carotenoid and phenolic compounds, which are well documented, there is little available information on tocopherols and almost none on tocotrienols. Considering the frequency of tocotrienol derivatives in Clusiaceae species, this study investigates and reports the presence of tocotrienols in eleven Hypericum species’ leaves: H. hircinum, H. hookerianum, H. calycinum, H. xylosteifolium, H. densifolium, H. prolificum, H. kalmianum, H. frondosum, H. olympicum, and two hybrids: H. × moserianum and H × ‘Rowallane’. Eight tocopherol and tocotrienol forms (α, β, γ, δ) were detected in the leaves, predominantly containing α-tocopherol. Tocotrienol content was most significant in Myriandra section species and was highest in H. prolificum (22.90 ± 0.63 mg 100 g⁻¹), while the highest tocotrienol proportion was observed in H. × ‘Rowallane’ (54.12% of total tocochromanols) and H. prolificum (37.27% of total tocochromanols). The results demonstrated significant tocochromanol accumulation in Hypericum leaves. Full article

(This article belongs to the Special Issue Extraction and Analysis of New Bioactive Compounds Derived from Natural Products, 2nd Edition)

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8 pages, 1753 KiB

Open AccessCommunication

Copper(I)-Photocatalyzed Addition of Trichloromethanesulfenyl Chloride to Olefinic Compounds

by Nejc Petek, Tilen Zorko, Martin Škrinjar, Uroš Grošelj, Jurij Svete, Drago Kočar and Bogdan Štefane

Molecules 2025, 30(3), 661; https://doi.org/10.3390/molecules30030661 (registering DOI) - 2 Feb 2025

Abstract

Atom transfer radical addition (ATRA) reactions are essential transformations in organic synthetic chemistry that enable the atom-economic difunctionalization of abundant olefin feedstocks. In this way, a rich chemical space can be opened up by well-planned combinations of simple starting materials. To build an [...] Read more.

Atom transfer radical addition (ATRA) reactions are essential transformations in organic synthetic chemistry that enable the atom-economic difunctionalization of abundant olefin feedstocks. In this way, a rich chemical space can be opened up by well-planned combinations of simple starting materials. To build an efficient photocatalytic transformation, the reactivity of trichloromethanesulfenyl chloride toward alkenes and alkynes was investigated under photocatalytic Cu(I) reaction conditions. In this study, we found that trichloromethanesulfenyl chloride can be added to a series of olefins (such as styrenes and electron-rich and -poor olefins) in the presence of 1 mol% [Cu(dmp)₂]BF₄ photocatalyst and blue LED irradiation, producing α-chloro trichloromethylthioethers in good yields. Experimental and theoretical (DFT) mechanistic studies are consistent with the proposed radical chain mechanism of transformation. This study may serve as a valuable reference for the development of new coupling reactions that are economical and highly efficient processes. Full article

(This article belongs to the Section Organic Chemistry)

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12 pages, 3923 KiB

Open AccessArticle

Evaluation of the Antibacterial Activity of Cinnamic Acid and Its Derivatives: Synergistic Effects with Cloxacillin

by Tomasz Zawiła, Denis Swolana, Jakub Rok, Zuzanna Rzepka and Robert D. Wojtyczka

Molecules 2025, 30(3), 660; https://doi.org/10.3390/molecules30030660 (registering DOI) - 2 Feb 2025

Abstract

Staphylococcus epidermidis is a widely prevalent microorganism whose key virulence factors include a high ability to adhere to synthetic surfaces and the capacity to form biofilms. The widespread distribution of multidrug-resistant strains (e.g., MRSE—methycillin-resistant Staphylococcus epidermidis) compels researchers to explore new therapeutic [...] Read more.

Staphylococcus epidermidis is a widely prevalent microorganism whose key virulence factors include a high ability to adhere to synthetic surfaces and the capacity to form biofilms. The widespread distribution of multidrug-resistant strains (e.g., MRSE—methycillin-resistant Staphylococcus epidermidis) compels researchers to explore new therapeutic approaches. Cinnamic acid and its derivatives are common plant-derived compounds known for their broad range of biological activities, including antimicrobial properties. The phenotypic assays conducted in this study revealed a strong anti-biofilm activity of the investigated compounds. Confocal laser scanning microscopy allowed for the visualization of structural changes within the biofilm and facilitated the assessment of bacterial cell viability in relation to the concentration of the tested substances. Full article

(This article belongs to the Special Issue Natural Products as New Antiviral/Antiparasitic/Antibacterial/Antimicrobial Treatment Options)

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18 pages, 2645 KiB

Open AccessArticle

Charge Regulation in Liquid Films Stabilized by Ionic Surfactants: Change in Adsorption with Film Thickness and Phase Transitions

by Iglika M. Dimitrova and Radomir I. Slavchov

Molecules 2025, 30(3), 659; https://doi.org/10.3390/molecules30030659 (registering DOI) - 1 Feb 2025

Abstract

When a liquid film is thinning, the charge and the potential of its surfaces change simultaneously due to the interaction between the two surfaces. This phenomenon is an example for charge regulation and has been known for half a century for systems featuring [...] Read more.

When a liquid film is thinning, the charge and the potential of its surfaces change simultaneously due to the interaction between the two surfaces. This phenomenon is an example for charge regulation and has been known for half a century for systems featuring aqueous solutions in contact with metals, salts, biological surfaces covered by protolytes, etc. Few studies, however, investigated regulation in foam and emulsion films, where the charge is carried by soluble ionic surfactants. This work presents an analysis of the phenomenon for surfactants that follow the classical Davies adsorption isotherm. The electrostatic disjoining pressure Π_el was analyzed, and the Davies isotherm was shown to lead to Π_el ∝ h^−1/2 behavior at a small film thickness h. As usual, the charge regulation regime (constant chemical potential of the surfactant) corresponded to a dependence of Π_el on h between those for constant charge and constant electric potential regimes. The role of the background electrolyte was also studied. At the water–air interface, many ionic surfactants exhibit a surface phase transition. We show that the interaction between the two surfaces of a foam film can trigger the phase transition (i.e., the film changes its charge abruptly), and two films of different h values can coexist in equilibrium with each other – one covered by surfactant in the 2D gaseous state and another in the 2D liquid state. Full article

(This article belongs to the Special Issue Amphiphilic Molecules, Interfaces and Colloids: 2nd Edition)

15 pages, 2711 KiB

Open AccessArticle

Melatonin Pre-Treatment Protects Erythrocytes Against Subsequent Oxidative Damage

by Tomas Jasenovec, Rastislav Vazan, Dominika Radosinska, Roman Gardlik and Jana Radosinska

Molecules 2025, 30(3), 658; https://doi.org/10.3390/molecules30030658 (registering DOI) - 1 Feb 2025

Abstract

Research on the effects of melatonin on erythrocyte deformability has yielded mixed results. While some studies reported improvements, others found no effect, and a few even noted a deterioration in deformability. Moreover, the impact of melatonin may vary between healthy erythrocytes and those [...] Read more.

Research on the effects of melatonin on erythrocyte deformability has yielded mixed results. While some studies reported improvements, others found no effect, and a few even noted a deterioration in deformability. Moreover, the impact of melatonin may vary between healthy erythrocytes and those subjected to oxidative stress. This study investigated the dose-dependent effects of melatonin on erythrocytes under baseline conditions and oxidative stress, using both pre- and post-stress incubation protocols. Oxidative damage was induced with tert-butyl hydroperoxide (TBHP), and its extent was assessed via dichlorofluorescein fluorescence. Erythrocyte deformability was measured using ektacytometry, and osmotic resistance was assessed through hemolytic assays. The results showed that incubation with TBHP led to a dose-dependent decline in both erythrocyte deformability and osmotic resistance. While melatonin treatment had no observable effect on intact erythrocytes, it enhanced deformability in oxidatively damaged erythrocytes when administered before oxidative stress was induced. However, the beneficial effect was not evident when melatonin was applied after oxidative damage. Additionally, melatonin incubation had no impact on the ability of erythrocytes to resist the hypotonic environment. In conclusion, this study supports the notion that the antioxidant properties of melatonin can improve erythrocyte functional status, as reflected by enhanced deformability, but not osmotic resistance. Notably, this effect was observed only in erythrocytes that were exposed to oxidative damage after melatonin incubation, not in intact cells. Full article

(This article belongs to the Section Medicinal Chemistry)

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22 pages, 1426 KiB

Open AccessArticle

Phytochemical Profile and Biological Activities of the Endemic Thymbra nabateorum Occurring in AlUla County, South-West Saudi Arabia

by Mohamed Djamel Miara, Sami Youssef, Yassine Fendane, Hassan Boukcim, Sami D. Almalki, Shauna K. Rees, Benjamin P.Y.-H. Lee, Abdalsamad Aldabaa, Hamdi Bendif and Ahmed H. Mohamed

Molecules 2025, 30(3), 657; https://doi.org/10.3390/molecules30030657 (registering DOI) - 1 Feb 2025

Abstract

Thymbra nabateorum, a plant species from the Lamiaceae family, is endemic to the Nabatian region, which spans southern Jordan and northwestern Saudi Arabia. It is renowned for its traditional uses and rich phytochemical profile. This study aims to examine the phytochemical composition [...] Read more.

Thymbra nabateorum, a plant species from the Lamiaceae family, is endemic to the Nabatian region, which spans southern Jordan and northwestern Saudi Arabia. It is renowned for its traditional uses and rich phytochemical profile. This study aims to examine the phytochemical composition of T. nabateorum and evaluate its biological activities, including antioxidant capacity, cytotoxic effects on cancer cell lines, and enzyme inhibition relevant to diabetes and neurodegenerative diseases. The essential oil (EO) and methanol extract of T. nabateorum were analyzed using Gas Chromatography–Mass Spectrometry (GC-MS) and High-Performance Liquid Chromatography (HPLC). Antioxidant activity was assessed using the DPPH radical scavenging assay. Cytotoxicity was evaluated against MDA-MB231 and LNCaP cancer cell lines using the MTT assay. Enzyme inhibition assays were conducted to determine the inhibitory effects on α-amylase, α-glucosidase, and butyrylcholinesterase. GC-MS analysis revealed thymol (82.30%) as the major component of the essential oil, while HPLC identified significant phenolic compounds in the methanol extract, including diosmin (118.75 mg/g) and hesperidin (22.18 mg/g). The DPPH assay demonstrated strong antioxidant activity, with the methanol extract showing an IC50 of 11.97 μg/mL for α-amylase and 31.99 μg/mL for α-glucosidase, indicating notable antidiabetic potential. Cytotoxicity tests revealed significant antiproliferative effects against both cancer cell lines, with lower IC50 values compared to standard treatments. T. nabateorum exhibits substantial antioxidant, cytotoxic, and enzyme inhibition activities, supporting its traditional medicinal uses. These findings provide a scientific basis for further research into its bioactive compounds and potential applications in modern pharmacology, particularly in developing natural therapeutic agents for oxidative stress-related diseases and cancer. Full article

(This article belongs to the Section Natural Products Chemistry)

21 pages, 7878 KiB

Open AccessArticle

Carboxyethylsilanetriol-Functionalized Al-MIL-53-Supported Palladium Catalyst for Enhancing Suzuki–Miyaura Cross-Coupling Reaction

by Yucang Liang, Xin Ning and Yanzhong Zhen

Molecules 2025, 30(3), 656; https://doi.org/10.3390/molecules30030656 (registering DOI) - 1 Feb 2025

Abstract

The application of metal–organic frameworks (MOFs) has attracted increasing attention in organic synthesis. The modification of MOFs can efficiently tailor the structure and improve the property for meeting ongoing demand in various applications, such as the alteration of gas adsorption and separation, catalytic [...] Read more.

The application of metal–organic frameworks (MOFs) has attracted increasing attention in organic synthesis. The modification of MOFs can efficiently tailor the structure and improve the property for meeting ongoing demand in various applications, such as the alteration of gas adsorption and separation, catalytic activity, stability, and sustainability or reusability. In this study, carboxyethylsilanetriol (CEST) disodium salt was used as a dual-functional ligand for modified Al-MIL-53 to fabricate CEST-functionalized Al-MIL-53 samples through a hydrothermal reaction of aluminum nitrate, terephthalic acid, and CEST disodium salt by varying the molar ratio of CEST to terephthalic acid and keeping a constant molar ratio of Al³⁺/-COOH of 1:1. The structure, composition, morphology, pore feature, and stability were characterized by XRD, different spectroscopies, electron microscopy, N₂ physisorption, and thermogravimetric analysis. With increasing CEST content, CEST-Al-MIL-53 still preserves an Al-MIL-53-like structure, but the microstructure changed compared with pure Al-MIL-53 due to the integration of CEST. Such a CEST-Al-MIL-53 was used as the support to load Pd particles and afford a catalyst Pd/CEST-Al-MIL-53 for Suzuki–Miyaura C-C cross-coupling reaction of aryl halides and phenylboronic acid under basic conditions. The resulting Pd/CEST-Al-MIL-53 showed a high catalytic activity compared with Pd/Al-MIL-53, due to the nanofibrous structure of silicon species-integrated CEST-Al-MIL-53. The nanofiber microstructure undergoes a remarkable transformation into intricate 3D cross-networks during catalytic reaction, which enables the leachable Pd particles to orientally redeposit and inlay into these networks as the monodisperse spheres and thereby effectively preventing Pd particles from aggregation and leaching, therefore demonstrating a high catalytic performance, long-term stability, and enhanced reusability. Obviously, the integration of CEST into MOFs can effectively prevent the leaching of active Pd species and ensure the re-deposition during catalysis. Moreover, catalytic performance strongly depended on catalyst dosage, temperature, time, solvent, and the type of the substituted group on benzene ring. This work further extends the catalytic application of hybrid metal–organic frameworks. Full article

(This article belongs to the Section Inorganic Chemistry)

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45 pages, 12731 KiB

Open AccessReview

Recent Developments in Stereoselective Reactions of Sulfoxonium Ylides

by Ciarán O’Shaughnessy, Mukulesh Mondal and Nessan J. Kerrigan

Molecules 2025, 30(3), 655; https://doi.org/10.3390/molecules30030655 (registering DOI) - 1 Feb 2025

Abstract

This review probes the recent developments in stereoselective reactions within the area of sulfoxonium ylide chemistry since the early 2000s. An abundance of research has been applied to sulfoxonium ylide chemistry since its emergence in the early 1960s. There has been a continued [...] Read more.

This review probes the recent developments in stereoselective reactions within the area of sulfoxonium ylide chemistry since the early 2000s. An abundance of research has been applied to sulfoxonium ylide chemistry since its emergence in the early 1960s. There has been a continued effort since then with work in traditional areas, such as epoxidation, aziridination and cyclopropanation. Efforts have also been applied in novel areas, such as olefination and insertion reactions, to develop stereoselective methodologies using organocatalysis and transition metal catalysis. The growing research area of interrupted Johnson–Corey–Chaykovsky reactions is also described, whereby unexpected stereoselective cyclopropanation and epoxidation methodologies have been developed. In general, the most observed mechanistic pathway of sulfoxonium ylides is the formal cycloaddition: (2 + 1) (e.g., epoxides, cyclopropanes, aziridines), (3 + 1) (e.g., oxetanes, azetidines), (4 + 1) (e.g., indanones, indolines). This pathway involves the formation of a zwitterionic intermediate through nucleophilic addition of the carbanion to an electrophilic site. An intramolecular cyclization occurs, constructing the cyclic product. Insertion reactions of sulfoxonium ylides to X–H bonds (e.g., X = S, N or P) are also observed, whereby protonation of the carbanion is followed by a nucleophilic addition of X, to form the inserted product. Full article

(This article belongs to the Special Issue Featured Reviews in Organic Chemistry 2025)

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34 pages, 2238 KiB

Open AccessReview

Epigallocatechin Gallate (EGCG): Pharmacological Properties, Biological Activities and Therapeutic Potential

by Lucia Capasso, Luigi De Masi, Carmina Sirignano, Viviana Maresca, Adriana Basile, Angela Nebbioso, Daniela Rigano and Paola Bontempo

Molecules 2025, 30(3), 654; https://doi.org/10.3390/molecules30030654 (registering DOI) - 1 Feb 2025

Abstract

Epigallocatechin gallate (EGCG), the predominant catechin in green tea, comprises approximately 50% of its total polyphenol content and has garnered widespread recognition for its significant therapeutic potential. As the principal bioactive component of Camellia sinensis, EGCG is celebrated for its potent antioxidant, [...] Read more.

Epigallocatechin gallate (EGCG), the predominant catechin in green tea, comprises approximately 50% of its total polyphenol content and has garnered widespread recognition for its significant therapeutic potential. As the principal bioactive component of Camellia sinensis, EGCG is celebrated for its potent antioxidant, anti-inflammatory, cardioprotective, and antitumor properties. The bioavailability and metabolism of EGCG within the gut microbiota underscore its systemic effects, as it is absorbed in the intestine, metabolized into bioactive compounds, and transported to target organs. This compound has been shown to influence key physiological pathways, particularly those related to lipid metabolism and inflammation, offering protective effects against a variety of diseases. EGCG’s ability to modulate cell signaling pathways associated with oxidative stress, apoptosis, and immune regulation highlights its multifaceted role in health promotion. Emerging evidence underscores EGCG’s therapeutic potential in preventing and managing a range of chronic conditions, including cancer, cardiovascular diseases, neurodegenerative disorders, and metabolic syndromes. Given the growing prevalence of lifestyle-related diseases and the increasing interest in natural compounds, EGCG presents a promising avenue for novel therapeutic strategies. This review aims to summarize current knowledge on EGCG, emphasizing its critical role as a versatile natural bioactive agent with diverse clinical applications. Further exploration in both experimental and clinical settings is essential to fully unlock its therapeutic potential. Full article

(This article belongs to the Special Issue Natural Products: Isolation, Analysis and Biological Activity, 2nd Edition)

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20 pages, 2542 KiB

Open AccessReview

Gamma-Tocopherol: A Comprehensive Review of Its Antioxidant, Anti-Inflammatory, and Anticancer Properties

by Basma Es-Sai, Hicham Wahnou, Salma Benayad, Soufiane Rabbaa, Yassir Laaziouez, Riad El Kebbaj, Youness Limami and Raphaël Emmanuel Duval

Molecules 2025, 30(3), 653; https://doi.org/10.3390/molecules30030653 (registering DOI) - 1 Feb 2025

Abstract

Gamma-tocopherol (γ-tocopherol), a major isoform of vitamin E, exhibits potent antioxidant, anti-inflammatory, and anticancer properties, making it a promising therapeutic candidate for treating oxidative stress-related diseases. Unlike other tocopherol isoforms, γ-tocopherol effectively neutralizes reactive oxygen species (ROS) and reactive nitrogen species (RNS), providing [...] Read more.

Gamma-tocopherol (γ-tocopherol), a major isoform of vitamin E, exhibits potent antioxidant, anti-inflammatory, and anticancer properties, making it a promising therapeutic candidate for treating oxidative stress-related diseases. Unlike other tocopherol isoforms, γ-tocopherol effectively neutralizes reactive oxygen species (ROS) and reactive nitrogen species (RNS), providing robust cellular protection against oxidative damage and lipid peroxidation. Its anti-inflammatory effects are mediated through the modulation of pathways involving cyclooxygenase-2 (COX-2) and tumor necrosis factor-alpha (TNF-α), reducing chronic inflammation and its associated risks. In cancer therapy, γ-tocopherol demonstrates multifaceted activity, including the inhibition of tumor growth, induction of apoptosis, and suppression of angiogenesis, with significant efficacy observed in cancers such as prostate, lung, and colon. Preclinical and clinical studies support its efficacy in mitigating oxidative stress, inflammation, and cancer progression, with excellent tolerance at physiological levels. However, high doses necessitate careful evaluation to minimize adverse effects. This review consolidates current knowledge on γ-tocopherol’s biological activities and clinical implications, underscoring its importance as a natural compound for managing inflammation, oxidative stress, and cancer. As a perspective, advancements in nanoformulation technology could enhance γ-tocopherol’s bioavailability, stability, and targeted delivery, offering the potential to optimize its therapeutic application in the future. Full article

(This article belongs to the Special Issue Advances in Plant-Sourced Natural Compounds as Anticancer Agents)

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28 pages, 1215 KiB

Open AccessReview

Towards Improved Bioavailability of Cereal Inositol Phosphates, Myo-Inositol and Phenolic Acids

by Krzysztof Żyła and Aleksandra Duda

Molecules 2025, 30(3), 652; https://doi.org/10.3390/molecules30030652 (registering DOI) - 1 Feb 2025

Abstract

Cereals are among the foods rich in myo-inositol hexakisphosphate (phytic acid, IP6), lower myo-inositol phosphates (IPx), a wide range of phenolic compounds, as well as vitamins, minerals, oligosaccharides, phytosterols and para-aminobenzoic acid, and are attributed with multiple bioactivities, particularly associated with [...] Read more.

Cereals are among the foods rich in myo-inositol hexakisphosphate (phytic acid, IP6), lower myo-inositol phosphates (IPx), a wide range of phenolic compounds, as well as vitamins, minerals, oligosaccharides, phytosterols and para-aminobenzoic acid, and are attributed with multiple bioactivities, particularly associated with the prevention of metabolic syndrome and colon cancer. The bran fraction of wheat, maize, brown rice and other cereals contains high levels of phytate, free and total phenolics, and endogenous enzymes such as amylases, phytase, xylanase, β-glucanase and feruloyl esterase, whose activities can be increased by germination. The preliminary steps of digestion begin in the oral cavity where substrates for the action of endogenous cereal and salivary enzymes start to be released from the food matrix. IP6 released from phytate complexes with arabinoxylans, starch and protein bodies would eventually enhance the absorption of nutrients, including phenolics, by regulating tight junctions and, together with ferulic acid (FA), would maintain cell barrier integrity and epithelial antibacterial immunity. In addition, both IP6 and FA exert potent and complementary antioxidant effects, while FA together with IPx generated through advanced hydrolysis of IP6 by endogenous and microbial phytases may affect digestive enzyme activity and incretin secretion, resulting in modulated insulin and glucagon release and prevention of various diabetic complications. Contrary to widespread negative attitudes towards phytate, in this review, we present the strategy of selecting cereals with high phytate and phenolic content, as well as high endogenous phytase, feruloyl esterase and endoxylanase activities, to produce value-added health-promoting foods. The advanced hydrolysis of phytate and phenolic compounds by cereal and/or microbial enzymes would generate substantial amounts of “enzymatically generated inositol” (EGI), including IP6, IPx and myo-inositol, the compounds that, together with free FA, provide enhanced bioavailability of cereal nutrients through multiple synergistic effects not previously realised. Full article

19 pages, 1716 KiB

Open AccessArticle

Elucidating the Mechanism of Coumarin Homodimerization Using 3-Acetylcoumarin Derivatives

by Kristina B. Simeonova, Ana I. Koleva, Nevena I. Petkova-Yankova, Anna-Mariya R. Zlatanova, Vesela Lozanova, Rositca D. Nikolova and Petko St. Petkov

Molecules 2025, 30(3), 651; https://doi.org/10.3390/molecules30030651 (registering DOI) - 1 Feb 2025

Abstract

The current study is a continuation of our previous investigations into the radical homodimeric reaction mechanism of 3-acetylcoumarin. In the current study, the effects of different substituents on the coumarin ring of 3-acetylcoumarin are investigated both experimentally and theoretically. Several 3-acetylcoumarin derivatives (substituted [...] Read more.

The current study is a continuation of our previous investigations into the radical homodimeric reaction mechanism of 3-acetylcoumarin. In the current study, the effects of different substituents on the coumarin ring of 3-acetylcoumarin are investigated both experimentally and theoretically. Several 3-acetylcoumarin derivatives (substituted at C-6, C-7, and C-8) were tested in the optimized reaction conditions under ultrasound irradiation, and biscoumarin species were isolated and characterized. The elucidation of the substituent’s effect was further investigated by means of DFT calculations (free-energy calculations, NBO analysis), both in the initial substituted coumarins and in the formed radicals. It was observed that the presence of substituents at the C-6 and C-8 positions in the coumarin moiety would not affect significantly the formation of a radical, while a group at position C-7 could either stabilize or destabilize the formed radical depending on the electronic properties of the substituent. Full article

(This article belongs to the Special Issue Coumarin and Its Derivatives III)

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24 pages, 2072 KiB

Open AccessReview

Machine Learning Descriptors for CO₂ Capture Materials

by Ibrahim B. Orhan, Yuankai Zhao, Ravichandar Babarao, Aaron W. Thornton and Tu C. Le

Molecules 2025, 30(3), 650; https://doi.org/10.3390/molecules30030650 (registering DOI) - 1 Feb 2025

Abstract

The influence of machine learning (ML) on scientific domains continues to grow, and the number of publications at the intersection of ML, CO₂ capture, and material science is growing rapidly. Approaches for building ML models vary in both objectives and the methods [...] Read more.

The influence of machine learning (ML) on scientific domains continues to grow, and the number of publications at the intersection of ML, CO₂ capture, and material science is growing rapidly. Approaches for building ML models vary in both objectives and the methods through which materials are represented (i.e., featurised). Featurisation based on descriptors, being a crucial step in building ML models, is the focus of this review. Metal organic frameworks, ionic liquids, and other materials are discussed in this paper with a focus on the descriptors used in the representation of CO₂-capturing materials. It is shown that operating conditions must be included in ML models in which multiple temperatures and/or pressures are used. Material descriptors can be used to differentiate the CO₂ capture candidates through descriptors falling under the broad categories of charge and orbital, thermodynamic, structural, and chemical composition-based descriptors. Depending on the application, dataset, and ML model used, these descriptors carry varying degrees of importance in the predictions made. Design strategies can then be derived based on a selection of important features. Overall, this review predicts that ML will play an even greater role in future innovations in CO₂ capture. Full article

(This article belongs to the Special Issue Machine Learning in Green Chemistry)

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