Molecules

18 pages, 5267 KiB

Open AccessArticle

The Puzzle of the Regioselectivity and Molecular Mechanism of the (3+2) Cycloaddition Reaction Between E-2-(Trimethylsilyl)-1-Nitroethene and Arylonitrile N-Oxides: Molecular Electron Density Theory (MEDT) Quantumchemical Study

by Mikołaj Sadowski, Ewa Dresler and Radomir Jasiński

Molecules 2025, 30(4), 974; https://doi.org/10.3390/molecules30040974 - 19 Feb 2025

Viewed by 245

Abstract

The regioselectivity and molecular mechanism of the (3+2) cycloaddition reaction between E-2-(trimethylsilyl)-1-nitroethene and arylonitrile N-oxides were explored on the basis of the ωB97XD/6-311+G(d) (PCM) quantumchemical calculations. It was found that the earlier postulate regarding the regioselectivity of the cycloaddition stage should [...] Read more.

The regioselectivity and molecular mechanism of the (3+2) cycloaddition reaction between E-2-(trimethylsilyl)-1-nitroethene and arylonitrile N-oxides were explored on the basis of the ωB97XD/6-311+G(d) (PCM) quantumchemical calculations. It was found that the earlier postulate regarding the regioselectivity of the cycloaddition stage should be undermined. Within our research, several aspects of the title reaction were also examined: interactions between reagents, electronic structures of alkenes and nitrile oxides, the nature of transition states, the influence of the polarity solvent on the reaction selectivity and mechanism, substituent effects, etc. The obtained results offer a general conclusion for all of the important aspects of some groups of cycloaddition processes. Full article

(This article belongs to the Special Issue Quantum Chemical Calculations of Molecular Reaction Processes)

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53 pages, 6609 KiB

Open AccessReview

Research Progress in Ionic Liquid-Based Electrolytes for Electrochromic Devices

by Hao Zhang, Yixuan Liu, Xuehan Wang, Keying Feng, Qilin Wang, Zheng Chen and Zhenhua Jiang

Molecules 2025, 30(4), 973; https://doi.org/10.3390/molecules30040973 - 19 Feb 2025

Viewed by 341

Abstract

Electrochromic (EC) technology has become one of the smart technologies with the most potential for development and application at this stage. Based on electrochromic devices (ECDs), this technology has shown extraordinary potential in the fields of smart windows, display devices, and sensing systems. [...] Read more.

Electrochromic (EC) technology has become one of the smart technologies with the most potential for development and application at this stage. Based on electrochromic devices (ECDs), this technology has shown extraordinary potential in the fields of smart windows, display devices, and sensing systems. With the optimization and iteration of various core components in ECDs, the electrolyte layer, a key component, evolved from its initial liquid state to a quasi-solid state and solid state. As driven by increasing application demands, the development trend indicates that all-solid-state, transparent electrolytes will likely become the future form of the electrolyte layer. Recently, the application of ionic liquid (IL)-based electrolytes in the field of electrochromism attracted a lot of attention due to their ability to bring outstanding EC cycling stability, thermal stability, and a wider operating voltage range to ECDs, and they are regarded as the new generation of electrolyte materials with the most potential for application. Although compared with conventional electrolytes, IL-based electrolytes have the characteristics of high price, high viscosity, and low conductivity, they are still considered the most promising electrolyte materials for applications. However, so far, there has been a lack of comprehensive analysis reports on “Research progress in ionic liquid-based electrolytes for electrochromic devices” within the EC field. In this article, the research progress of IL-based electrolytes in ECDs will be summarized from three perspectives: liquid, quasi-solid, and solid state. The future development directions of IL-based electrolytes for ECDs are discussed. Full article

(This article belongs to the Special Issue Advances of Ionic Liquids in Organic, Polymer and Material Chemistry: Key Trends in Green Chemistry)

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31 pages, 5710 KiB

Open AccessArticle

Antitumor Activity, Mechanisms of Action and Phytochemical Profiling of Sub-Fractions Obtained from Ulex gallii Planch. (Fabaceae): A Medicinal Plant from Galicia (Spain)

by Lucía Bada, Hussain Shakeel Butt, Elías Quezada, Aitor Picos, Helle Wangensteen, Kari Tvete Inngjerdingen, José Gil-Longo and Dolores Viña

Molecules 2025, 30(4), 972; https://doi.org/10.3390/molecules30040972 - 19 Feb 2025

Viewed by 347

Abstract

The plant kingdom serves as a valuable resource for cancer drug development. This study explored the antitumor activity of different sub-fractions (hexane, dichloromethane and methanol) of U. gallii (gorse) methanol extract in glioblastoma (U-87MG and U-373MG) and neuroblastoma (SH-SY5Y) cell lines, along with [...] Read more.

The plant kingdom serves as a valuable resource for cancer drug development. This study explored the antitumor activity of different sub-fractions (hexane, dichloromethane and methanol) of U. gallii (gorse) methanol extract in glioblastoma (U-87MG and U-373MG) and neuroblastoma (SH-SY5Y) cell lines, along with their phytochemical profiles. Cytotoxicity was evaluated using 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) and lactate dehydrogenase (LDH) assays, and cell cycle arrest and apoptosis were assessed through flow cytometry and by measuring reactive oxygen species (ROS) and protein expression levels. D7 and D8 dichloromethane sub-fractions significantly reduced cell viability, triggered early apoptosis in SH-SY5Y and U-87MG cells and specifically increased ROS levels in U-87MG cells. Western blot analyses showed that D7 increased p53, caspase-3, caspase-8 and γH2AX expression in SH-SY5Y and U-87MG cells, while D8 specifically elevated p53 in SH-SY5Y cells and caspase-3 in both cell lines. In U-373 cells, D7 and D8 markedly reduced cell viability, with D8 inducing necrosis. Morphological changes indicative of apoptosis were also observed in all cell lines. Bioinformatic analysis of UHPLC-MS and GC-MS data tentatively identified 20 metabolites in D7 and 15 in D8, primarily flavonoids. HPLC-DAD confirmed isoprunetin and genistein as the most abundant in D7 and D8, respectively, both isolated and identified by NMR spectroscopy. Most of the flavonoids identified have been reported as antitumor agents, suggesting that these compounds may be responsible for the observed pharmacological activity. Full article

(This article belongs to the Special Issue Exploration of Natural Compounds: Pharmaceutical, Phytochemical and Biological Analyses—2nd Edition)

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17 pages, 1770 KiB

Open AccessArticle

Revisiting the Mechanistic Pathway of Gas-Phase Reactions in InN MOVPE Through DFT Calculations

by Xiaokun He, Nan Xu, Yuan Xue, Hong Zhang, Ran Zuo and Qian Xu

Molecules 2025, 30(4), 971; https://doi.org/10.3390/molecules30040971 - 19 Feb 2025

Viewed by 301

Abstract

III-nitrides are crucial materials for solar flow batteries due to their versatile properties. In contrast to the well-studied MOVPE reaction mechanism for AlN and GaN, few works report gas-phase mechanistic studies on the growth of InN. To better understand the reaction thermodynamics, this [...] Read more.

III-nitrides are crucial materials for solar flow batteries due to their versatile properties. In contrast to the well-studied MOVPE reaction mechanism for AlN and GaN, few works report gas-phase mechanistic studies on the growth of InN. To better understand the reaction thermodynamics, this work revisited the gas-phase reactions involved in metal–organic vapor-phase epitaxy (abbreviated as MOVPE) growth of InN. Utilizing the M06-2X function in conjunction with Pople’s triple-ζ split-valence basis set with polarization functions, this work recharacterized all stationary points reported in previous literature and compared the differences between the structures and reaction energies. For the reaction pathways which do not include a transition state, rigorous constrained geometry optimizations were utilized to scan the PES connecting the reactants and products in adduct formation and XMIn (M, D, T) pyrolysis, confirming that there are no TSs in these pathways, which is in agreement with the previous findings. A comprehensive bonding analysis indicates that in TMIn:NH₃, the In-N demonstrates strong coordinate bond characteristics, whereas in DMIn:NH₃ and MMIn:NH₃, the interactions between the Lewis acid and base fragments lean toward electrostatic attraction. Additionally, the NBO computations show that the H radical can facilitate the migration of electrons that are originally distributed between the In-C bonds in XMIn. Based on this finding, novel reaction pathways were also investigated. When the H radical approaches MMInNH₂, MMIn:NH₃ rather than MMInHNH₂ will generate and this is followed by the elimination of CH₄ via two parallel paths. Considering the abundance of H₂ in the environment, this work also examines the reactions between H₂ and XMIn. The Mulliken charge distributions indicated that intermolecular electron transfer mainly occurs between the In atom and N atom whiling forming (DMInNH₂)₂, whereas it predominately occurs between the In atom and the N atom intramolecularly when generating (DMInNH₂)₃. Full article

(This article belongs to the Section Physical Chemistry)

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19 pages, 800 KiB

Open AccessArticle

Determination of the Polyphenol Composition of Raspberry Leaf Using LC-MS/MS

by Hind Mesfer S. Alkhudaydi, Esther Njeri Muriuki and Jeremy P. E. Spencer

Molecules 2025, 30(4), 970; https://doi.org/10.3390/molecules30040970 - 19 Feb 2025

Viewed by 410

Abstract

Background: Raspberry leaf (RL; Rubus idaeus) is a by-product of raspberry cultivation and has been proposed to be a rich source of micronutrients and potential bioactive components, including polyphenols. However, the precise chemical composition of the non-nutrient (poly)phenols in RL has not [...] Read more.

Background: Raspberry leaf (RL; Rubus idaeus) is a by-product of raspberry cultivation and has been proposed to be a rich source of micronutrients and potential bioactive components, including polyphenols. However, the precise chemical composition of the non-nutrient (poly)phenols in RL has not been as extensively studied. Objective: To evaluate the (poly)phenolic content of six RL samples from different geographical locations and to explore the impact of brewing duration on the levels of phenolic compounds available for absorption following consumption. Methods: A total of 52 polyphenolic constituents were investigated in the RL samples using Liquid Chromatography–Mass Spectrometry (LC-MS), and RL tea samples were analysed for ellagitannins, flavonoids, and phenolic acids. Tea samples were extracted using 80:20 (v/v) methanol/acidified water (0.1% formic acid) to maximise polyphenol recovery, with two sonication steps (30 and 25 min), followed by centrifugation, filtration, and storage at −18 °C. Extractions were performed in triplicate for comprehensive profiling. Additionally, raspberry leaf tea (2 g) was brewed in 200 mL of boiling water at various times (0.5–20 min) to simulate standard consumption practices; this was also performed in triplicate. This approach aimed to quantify polyphenols in the brew and identify optimal steeping times for maximum polyphenol release. Results: Raspberry leaf (RL) samples from six geographical sources were analysed, with 37 compounds identified in methanol and 37 in water out of the 52 targeted compounds, with only 7 compounds not detected in either methanol or water extracts. The analysis indicated that the total measured polyphenol content across the six samples from various sources ranged between 358.66 and 601.65 mg/100 g (p < 0.001). Ellagitannins were identified as the predominant polyphenolic compound in all RL samples, ranging from 155.27 to 394.22 mg/100 g. The phenolic acid and flavonoid concentrations in these samples exhibited a relatively narrow range, with the phenolic acids spanning from 38.87 to 119.03 mg/100 g and the flavonoids ranging from 125.03 to 156.73 mg/100 g. When brewing the tea, the 5 min extraction time was observed to yield the highest level of polyphenols (505.65 mg/100 g) (p< 0.001), which was significantly higher than that with shorter (409.84 mg/100g) and longer extraction times (429.28 mg/100 g). Notably, ellagic acid levels were highest at 5 min (380.29 mg/100 g), while phenolic acid peaked at 15 min (50.96 mg/100 g). The flavonoid content was shown to be highest at 4 min (82.58 mg/100 g). Conclusions: RL contains a relatively high level of polyphenols, particularly ellagic acid; thus, its consumption may contribute to the daily intake of these health-beneficial non-nutrient components. Full article

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17 pages, 4224 KiB

Open AccessArticle

Stability and Reusability of Tungsten Catalyst on Structured Support in Catalytic Ozonation of Textile Wastewater

by Aleksandra Kędzierska-Sar, Maciej Fronczak, Marta Gmurek and Lucyna Bilińska

Molecules 2025, 30(4), 969; https://doi.org/10.3390/molecules30040969 - 19 Feb 2025

Viewed by 274

Abstract

Since heterogeneous catalytic ozonation (HCO) has become a leading trend in advanced oxidation processes, finding new prospective catalysts has become crucial. Plasma-enhanced chemical vapor deposition (PECVD) is a method of thin-layer deposition that is useful in catalyst production on structured supports. This study [...] Read more.

Since heterogeneous catalytic ozonation (HCO) has become a leading trend in advanced oxidation processes, finding new prospective catalysts has become crucial. Plasma-enhanced chemical vapor deposition (PECVD) is a method of thin-layer deposition that is useful in catalyst production on structured supports. This study presents a novel tungsten (W)-based catalyst used in HCO for textile wastewater discoloration. By changing PECVD parameters, we were able to design and prepare several types of diverse catalysts in terms of morphology and composition. Energy-dispersive X-ray spectroscopy was used for catalyst characterization and revealed a nano-sized granular morphology. The catalyst thickness was below 500 nm, preserving the geometry of the support. The satisfactory high W catalyst activity in dye removal was investigated through a catalytic test. The increased speed in color removal, represented by the enhancement factor, was equal to 1.47 when comparing single and catalytic ozonation. A high and almost unchanged color removal efficiency was maintained over seven cycles of HCO, allowing for more than 5 h of successful use. Full article

(This article belongs to the Special Issue Catalysts: New Materials for Green Chemistry)

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10 pages, 1257 KiB

Open AccessArticle

Kinetics of Photodegradation and Durability of Inkjet Prints: A Comparative Study of Aqueous Solutions and Printed Substrates

by Barbara Blaznik, Franci Kovač and Sabina Bračko

Molecules 2025, 30(4), 968; https://doi.org/10.3390/molecules30040968 - 19 Feb 2025

Viewed by 232

Abstract

The durability of the materials is often limited as they fade under the influence of external factors, particularly light. The present research aimed to study the photodegradation of commercial inkjet inks in an aqueous solution. The results were compared with their stability on [...] Read more.

The durability of the materials is often limited as they fade under the influence of external factors, particularly light. The present research aimed to study the photodegradation of commercial inkjet inks in an aqueous solution. The results were compared with their stability on prints in order to establish the connection between the kinetics of photodegradation of dye in the solution and the durability of the final print. Thin-layer chromatography (TLC), chromatography with a mass selective detector (GC/MS), and spectrophotometric measurements were used to study the effect of light, including near UV. The results clearly show that the catalytic effect between different dyes cannot be avoided, as the inks for inkjet printing are usually a mixture of different colorants. A comparison of the results of photodegradation of the dye in solution and on the final prints does not show a direct connection due to the different influences of external factors. Consequently, it was established that it is not possible to predict the photodegradation of prints solely based on a single dye’s analysis in solution. The paper as a substrate must be included in the analysis, as it significantly influences the photodegradation of the print. Full article

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45 pages, 6993 KiB

Open AccessReview

Xanthone Dimers in Angiosperms, Fungi, Lichens: Comprehensive Review of Their Sources, Structures, and Pharmacological Properties

by Fengzhi Shi, Min Fan, Haifeng Li, Shiwei Li and Shuang Wang

Molecules 2025, 30(4), 967; https://doi.org/10.3390/molecules30040967 - 19 Feb 2025

Viewed by 347

Abstract

Xanthone dimers, a distinctive class of natural metabolites renowned for their unique structures, are abundantly present in a diverse array of angiosperms, fungi, and lichens. These compounds not only exhibit remarkable diversity but also possess a broad spectrum of biological activities. In this [...] Read more.

Xanthone dimers, a distinctive class of natural metabolites renowned for their unique structures, are abundantly present in a diverse array of angiosperms, fungi, and lichens. These compounds not only exhibit remarkable diversity but also possess a broad spectrum of biological activities. In this comprehensive review spanning from 1966 to 2024, we synthesized the relevant literature to delve into the natural occurrence, biological potency, molecular structure and chemical diversity of xanthone dimers. The aim of this review is to serve as an insightful reference point for future scientific inquiries into xanthone dimers and their potential applications. Full article

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12 pages, 1499 KiB

Open AccessArticle

Effects of Additional Mesopores and the Surface Modification of the Y-Type Zeolite on the Alkane Oxidation Activity of Iron Complex-Encapsulated Catalysts

by Takamasa Takeda, Masaya Okamura, Syuhei Yamaguchi, Hidenori Yahiro and Shiro Hikichi

Molecules 2025, 30(4), 966; https://doi.org/10.3390/molecules30040966 - 19 Feb 2025

Viewed by 208

Abstract

Catalytic alkane hydroxylation activities of the iron complex encapsulated into the micropore of the Y-type zeolite and mesoporous zeolites, the latter of which were obtained by the partial removal of aluminum and alkaline treatment, have been explored by using H₂O₂ [...] Read more.

Catalytic alkane hydroxylation activities of the iron complex encapsulated into the micropore of the Y-type zeolite and mesoporous zeolites, the latter of which were obtained by the partial removal of aluminum and alkaline treatment, have been explored by using H₂O₂ as the oxidant. The iron complex with tris(pyridylmethyl)amine (=TPA) encapsulated into the micropore of the genuine Y-type zeolite was a more stable and effective cyclohexane hydroxylating heterogeneous catalyst compared to the corresponding copper analogue as well as the non-encapsulated homogeneous Fe-TPA complex. The chemical modification of the zeolite supports with the organic groups led to changing the catalytic activity depending on the size and the hydrophobic or hydrophilic nature of the added organic groups. When the content of water in the solvent was increased, the activity of the hydrophilic longer chain-modified catalyst was improved compared to that applied on the reaction with the non-aqueous solvent. The hydrophobic fluoroalkyl modifier located near the entrance of the micropore hindered the access of the substrate and aqueous H₂O₂ to the encapsulated iron complex site in the genuine Y-type zeolite. On the other hand, the hydrophobic modification effectively improved the activity of the catalyst with the zeolite support having higher amounts of mesopores. The synergistic effect of the wider bore diameters and the hydrophobic nature derived from the fluoroalkyl chains led to the concentration of the hydrocarbon substrate near the active iron complex. Full article

(This article belongs to the Special Issue Synthesis and Applications of Zeolites and Related Porous Materials as Adsorbents and Catalysts)

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19 pages, 2419 KiB

Open AccessArticle

Promiscuity in Polyphenol–Protein Interactions—Monitoring Protein Conformational Change upon Polyphenol–Protein Binding by Nano-Differential Fluorimetry (Nano-DSF)

by Dorothea Schmidt, Amelie Wohlers and Nikolai Kuhnert

Molecules 2025, 30(4), 965; https://doi.org/10.3390/molecules30040965 - 19 Feb 2025

Viewed by 227

Abstract

In this article, we introduce nano-differential fluorimetry (nano-DSF) as an analytical technique that is suitable for investigating polyphenol–protein interactions in solution. Nano-DSF monitors conformational changes in proteins induced by external agents upon interaction at the molecular level. We demonstrate the suitability of this [...] Read more.

In this article, we introduce nano-differential fluorimetry (nano-DSF) as an analytical technique that is suitable for investigating polyphenol–protein interactions in solution. Nano-DSF monitors conformational changes in proteins induced by external agents upon interaction at the molecular level. We demonstrate the suitability of this technique to qualitatively monitor an interaction between selected dietary polyphenols and selected proteins including BSA, ovalbumin, amylase, pepsin, trypsin, mucin and ACE-1. Protein conformational changes induced by dietary polyphenols can be investigated. As a major advantage, measurements are carried out at a high dilution, avoiding the precipitation of polyphenol–protein complexes, allowing the rapid and efficient acquisition of quantitative and qualitative binding data. From this concentration, quantitative binding data could be obtained from the fluorescence response curve in line with published values for the association constants. We demonstrate that qualitative interactions can also be established for real food extracts such as cocoa, tea or coffee containing mixtures of dietary polyphenols. Most importantly, we demonstrate that polyphenols of very different structural classes interact with the same protein target. Conversely, multiple protein targets show an affinity to a series of structurally diverse polyphenols, therefore suggesting a dual level of promiscuity with respect to the protein target and polyphenol structure. Full article

(This article belongs to the Special Issue Bioactive Phenolic and Polyphenolic Compounds, Volume III)

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17 pages, 909 KiB

Open AccessArticle

Supercritical Fluid Extraction of Lipids from Rowanberry Pomace with Pure CO₂ and Its Mixtures with Ethanol Followed by the On-Line Separation of Fractions

by Viive Sarv, Rajeev Bhat, Laura Jūrienė, Renata Baranauskienė, Dalia Urbonavičienė, Pranas Viškelis and Petras Rimantas Venskutonis

Molecules 2025, 30(4), 964; https://doi.org/10.3390/molecules30040964 - 19 Feb 2025

Viewed by 221

Abstract

Fruit processing by-products contain various classes of bioactive constituents, which may find applications as ingredients for foods, nutraceuticals or cosmeceuticals. This study explored the fractionation of lipophilic rowanberry pomace extracts isolated with pure supercritical CO₂ and its mixtures with a co-solvent ethanol [...] Read more.

Fruit processing by-products contain various classes of bioactive constituents, which may find applications as ingredients for foods, nutraceuticals or cosmeceuticals. This study explored the fractionation of lipophilic rowanberry pomace extracts isolated with pure supercritical CO₂ and its mixtures with a co-solvent ethanol by their on-line separation at subcritical conditions. Rowanberry pomace lipids were extracted with supercritical CO₂ (42.4 MPa, 53 °C) using 0–7% of ethanol, and then fractionated by reducing the first separator’s (S1) pressure to 7 MPa and cooling it to 0, −10 and −20 °C to precipitate the ‘heavier’ fraction (HF). The second separator (S2) was depressurized at ambient temperatures to collect the ‘lighter’ fraction (LF). The yield of the LF increased by decreasing the S1 temperature and increasing the amount of the co-solvent. The concentration of β-carotene was increased in the LF by decreasing the S1 temperature and increasing the co-solvent concentration; at −20 °C it was 66.7% higher than in the non-fractionated extract. The concentrations of tocopherols and phytosterols were also remarkably higher in the LF. In total, 62 compounds were identified in the headspace volatile fraction of the LF, benzaldehyde and benzyl alcohol being the most abundant constituents. In conclusion, fractionation enabled us to obtain fractions with higher concentrations of the selected classes of lipophilic rowanberry constituents. Full article

(This article belongs to the Special Issue Supercritical Fluid Extraction of Natural Bioactive Compounds)

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22 pages, 18245 KiB

Open AccessArticle

Co-Improvement in Electrocatalytic Hydrogen Evolution Performance of MoS₂ by Ni Doping and Graphene Oxide Compounding

by Guiquan Guo, Yuqin Li, Shujiao Zhang, Cuijuan Xing and Qi Wang

Molecules 2025, 30(4), 963; https://doi.org/10.3390/molecules30040963 - 19 Feb 2025

Viewed by 228

Abstract

Molybdenum disulfide (MoS₂) is a promising catalyst for hydrogen evolution through water electrolysis with low cost and high efficiency, but its hydrogen evolution performance can be further improved. Using sodium molybdate (Na₂MoO₄·2H₂O) and thiourea (NH [...] Read more.

Molybdenum disulfide (MoS₂) is a promising catalyst for hydrogen evolution through water electrolysis with low cost and high efficiency, but its hydrogen evolution performance can be further improved. Using sodium molybdate (Na₂MoO₄·2H₂O) and thiourea (NH₂CSNH₂) as raw materials, MoS₂ was prepared by the hydrothermal method. Ni-doped MoS₂(Ni-MoS₂) was prepared by using nickel dichloride dihydrate (NiCl₂·2H₂O) as a Ni source and doping Ni into MoS₂ by the hydrothermal method. Under the conditions of different temperatures (190 °C, 200 °C, and 210 °C) and different Ni doping molar ratios (2%, 3%, and 4%), the optimum temperature and doping ratio of the prepared materials were explored by conducting a hydrogen evolution reaction (HER) by the electrolysis of water. The results showed that the optimum preparation temperature was 200 °C and the optimum molar ratio of Ni doping was 3%. Graphene oxide (GO) was obtained by oxidation of graphite (G), and then Ni-MoS₂/GO was prepared by the hydrothermal method with Ni-MoS₂ and GO. The performance of HER was tested. The materials were characterized by X-ray diffraction (XRD), scanning electron microscope (SEM), high-resolution transmission electron microscope (HRTEM), and X-ray photoelectron spectroscopy (XPS). The results show that the composite Ni-MoS₂/GO has good HER performance, which is better than that of MoS₂ or Ni-MoS₂. In 0.5 M H₂SO₄ solution, the η₁₀ is as low as 196 mV, the Tafel slope is 122 mV/dec, the C_dl is 13.98 mF/cm², and it has good stability. The enhancement of electrocatalytic activity is mainly due to the doping of a small amount of Ni, which increases the defects of the catalyst and forms more active sites. GO improves the conductivity of the material. Ni doping and GO compounding promote the HER performance of MoS₂. Full article

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24 pages, 3141 KiB

Open AccessReview

Advanced Nanomedicine Delivery Systems for Cardiovascular Diseases: Viral and Non-Viral Strategies in Targeted Therapy

by Qian Chen, Tong Yu, Jingyi Gong and Hongli Shan

Molecules 2025, 30(4), 962; https://doi.org/10.3390/molecules30040962 - 19 Feb 2025

Viewed by 288

Abstract

Cardiovascular diseases (CVDs) represent a leading global health crisis, significantly impairing patients’ quality of life and posing substantial risks to their survival. Conventional therapies for CVDs often grapple with challenges such as inadequate targeting precision, suboptimal therapeutic efficacy, and potential adverse side effects. [...] Read more.

Cardiovascular diseases (CVDs) represent a leading global health crisis, significantly impairing patients’ quality of life and posing substantial risks to their survival. Conventional therapies for CVDs often grapple with challenges such as inadequate targeting precision, suboptimal therapeutic efficacy, and potential adverse side effects. To address these shortcomings, researchers are intensively developing advanced drug delivery systems characterized by high specificity and selectivity, excellent biodegradability, superior biocompatibility, and minimal toxicity. These innovative systems enable the precise delivery of pharmaceuticals with high drug-loading capacities, minimal leakage, and expansive specific surface areas, thereby enhancing therapeutic outcomes. In this review, we summarize and classify various drug delivery materials targeting CVDs and application values. We also evaluate the feasibility and efficacy of viral and non-viral vectors for the treatment of CVDs, the existing limitations and application prospects are also discussed. We hope that this review will provide new perspectives for the future development of drug delivery systems for the treatment of CVDs, ultimately contributing to improved patient care and outcomes. Full article

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27 pages, 8522 KiB

Open AccessArticle

Ultrasound-Assisted Extraction of Polysaccharides from Lyophyllum decastes: Structural Analysis and Bioactivity Assessment

by Qiong Wu, Bin Liang, Jiaming Wang and Yonggang Dai

Molecules 2025, 30(4), 961; https://doi.org/10.3390/molecules30040961 - 19 Feb 2025

Viewed by 283

Abstract

This study employed ultrasound-assisted extraction (UAE) to isolate polysaccharides from Lyophyllum decastes, which were subsequently fractionated into two components, LDP-A1 and LDP-B1, using DEAE cellulose-52 and Sephacryl S-500. The structural characteristics of the polysaccharides were preliminarily analyzed using high-performance liquid chromatography (HPLC), [...] Read more.

This study employed ultrasound-assisted extraction (UAE) to isolate polysaccharides from Lyophyllum decastes, which were subsequently fractionated into two components, LDP-A1 and LDP-B1, using DEAE cellulose-52 and Sephacryl S-500. The structural characteristics of the polysaccharides were preliminarily analyzed using high-performance liquid chromatography (HPLC), Fourier-transform infrared (FTIR) spectroscopy, scanning electron microscopy (SEM), X-ray diffraction (XRD), and Congo red staining. The results indicate significant differences between LDP-A1 and LDP-B1 in terms of molecular weight, monosaccharide composition, and structural features. LDP-A1 (2.27 × 10⁶ Da) exhibits a significantly higher molecular weight compared to LDP-B1 (9.80 × 10⁵ Da), with distinct differences in monosaccharide types and content. Both polysaccharides contain β-glycosidic bonds. LDP-B1 adopts a sheet-like structure with an amorphous internal arrangement and a triple-helix configuration, whereas LDP-A1 is rod-shaped, with a crystalline internal structure, and lacks the triple-helix configuration. In terms of biological activity, both polysaccharides exhibit certain activities, but LDP-B1 shows significantly stronger activity in antioxidant, hypoglycemic, anti-inflammatory, and anticancer effects. In summary, LDPs exhibit significant biological activity, especially outstanding performance in antioxidant, hypoglycemic, anti-inflammatory, and anticancer effects, proving their potential for development in functional foods and pharmaceuticals. Their unique structural characteristics and diverse biological activities provide a solid theoretical foundation for further exploration of LDPs in health promotion and disease prevention, opening up new research directions and application prospects. Full article

(This article belongs to the Special Issue Research and Application of Plant Sourced Polysaccharides—2nd Edition)

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19 pages, 2227 KiB

Open AccessReview

Anticancer Activity of Ether Derivatives of Chrysin

by Arkadiusz Sokal, Patryk Mruczek, Mateusz Niedoba, Agnieszka Dewalska, Klaudia Stocerz and Monika Kadela-Tomanek

Molecules 2025, 30(4), 960; https://doi.org/10.3390/molecules30040960 - 19 Feb 2025

Viewed by 341

Abstract

Chrysin, a naturally occurring flavonoid, exhibits a broad spectrum of biological activities, including showing anticancer properties. However, its clinical application is limited by poor bioavailability and low solubility. The introduction of an amine, amide, ester, or alkoxy group to a flavone skeleton influences [...] Read more.

Chrysin, a naturally occurring flavonoid, exhibits a broad spectrum of biological activities, including showing anticancer properties. However, its clinical application is limited by poor bioavailability and low solubility. The introduction of an amine, amide, ester, or alkoxy group to a flavone skeleton influences the biological activity. This review also discusses hybrid compounds, such as the chrysin–porphyrin hybrid, which are characterized by higher biological activity and better bioavailability properties than single molecules. This review concentrates on the anticancer activity of chrysin and its derivatives against the most popular cancers, such as breast, lung, prostate, and gastrointestinal tumors. Full article

(This article belongs to the Special Issue Synthesis, Identification and Biological Evaluation of Novel Natural and Derivative Products)

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18 pages, 2347 KiB

Open AccessArticle

Bioconversion of Liquid and Solid Lipid Waste by Yarrowia lipolytica Yeast: A Study of Extracellular Lipase Biosynthesis and Microbial Lipid Production

by Katarzyna Wierzchowska, Karolina Szulc, Bartłomiej Zieniuk and Agata Fabiszewska

Molecules 2025, 30(4), 959; https://doi.org/10.3390/molecules30040959 - 19 Feb 2025

Viewed by 280

Abstract

This study investigated the capabilities of Yarrowia lipolytica strains to grow in media with different hydrophobic wastes from the meat industry. The yeast growth, cellular lipid accumulation, production of lipases, and degree of utilization of liquid and solid lipid wastes were studied in [...] Read more.

This study investigated the capabilities of Yarrowia lipolytica strains to grow in media with different hydrophobic wastes from the meat industry. The yeast growth, cellular lipid accumulation, production of lipases, and degree of utilization of liquid and solid lipid wastes were studied in shaken cultures in media with organic and inorganic nitrogen sources. The effects of the type of waste, initial concentration of carbon source, Yarrowia strain, and inoculum size were investigated in two experimental sets using the Latin Square 5 × 5 design method. Post-frying rapeseed oil from chicken frying was selected as the carbon source to promote biomass growth. In contrast, the solid lipid fraction from meat broths promoted efficient lipid accumulation and yeast lipolytic activity. An initial concentration of the carbon source at 8% m/v stimulated efficient lipid biosynthesis and lipase production, while 2.5% v/v inoculum provided optimal conditions for the growth and utilization of hydrophobic substrates. No significant differences were observed in the particle dispersion of the liquid and solid wastes in the culture media (span = 2.51–3.23). The maximum emulsification index (62%) was observed in the culture of the Y. lipolytica KKP 323 strain in the medium with post-frying rapeseed oil from chicken frying, which was correlated with biosurfactant synthesis. It was concluded that the type of waste, its structure, and its composition affected various physiological yeast responses. Full article

(This article belongs to the Special Issue Exclusive Feature Papers in Macromolecular Chemistry)

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23 pages, 9235 KiB

Open AccessReview

Recent Advances in Resveratrol Derivatives: Structural Modifications and Biological Activities

by Xiaohan Liu, Jian Pei, Jiahui Li, Huiyu Zhu, Xiaoyu Zheng, Xingxing Zhang, Banfeng Ruan and Liuzeng Chen

Molecules 2025, 30(4), 958; https://doi.org/10.3390/molecules30040958 - 19 Feb 2025

Viewed by 291

Abstract

Resveratrol, a naturally occurring phenolic stilbene molecule, has been intensively researched for its anti-inflammatory, anticancer, antioxidant, antibacterial, and neuroprotective properties. However, due to its limited absorption and probable hepatotoxicity, it is difficult to employ directly as a medication, limiting its therapeutic applicability. Over [...] Read more.

Resveratrol, a naturally occurring phenolic stilbene molecule, has been intensively researched for its anti-inflammatory, anticancer, antioxidant, antibacterial, and neuroprotective properties. However, due to its limited absorption and probable hepatotoxicity, it is difficult to employ directly as a medication, limiting its therapeutic applicability. Over the last five years, numerous structural changes in resveratrol have been widely studied, resulting in considerable improvements in pharmacological activity and drug availability. This work reviews the biological activities and structure–activity relationships (SARs) of resveratrol derivatives, with the goal of providing useful insights for the discovery of new resveratrol derivatives. Full article

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12 pages, 1558 KiB

Open AccessArticle

Cytochalasins from the Ash Endophytic Fungus Nemania diffusa DSM 116299

by Özge Demir, Katharina Schmidt, Barbara Schulz, Theresia E. B. Stradal and Frank Surup

Molecules 2025, 30(4), 957; https://doi.org/10.3390/molecules30040957 - 19 Feb 2025

Viewed by 271

Abstract

The secondary metabolome of Nemania diffusa, isolated as an ash endophytic fungus, was analyzed in detail. From its cultures, a previously undescribed cytochalasin 1 was isolated using preparative HPLC, together with six known congeners: 18-dehydroxy-cytochalasin E (2), cytochalasins Z₇ [...] Read more.

The secondary metabolome of Nemania diffusa, isolated as an ash endophytic fungus, was analyzed in detail. From its cultures, a previously undescribed cytochalasin 1 was isolated using preparative HPLC, together with six known congeners: 18-dehydroxy-cytochalasin E (2), cytochalasins Z₇ (3), Z₈ (4), and E (5), 18-dehydroxy-17-didehydro-cytochalasin E (6), and K Steyn (7). The structures of these compounds were determined using data from high-resolution mass spectrometry (HR-MS), in combination with 1D and 2D nuclear magnetic resonance (NMR) spectroscopy. Metabolites 1–4 share a characteristic 12-membered lactone moiety, placing them within a rarely examined cytochalasin subclass. Thus, the compounds were incorporated into our ongoing screening campaign to study the structure–activity relationship of this metabolite family. We initially determined their cytotoxicity in eukaryotic mouse fibroblast L929 cells using an MTT-based colorimetric assay, and further investigated their effect on the cellular actin dynamics of the human osteosarcoma cell line U-2OS in detail. Unexpectedly, we discovered a high number of irreversible compounds (1, 2, and 4). Additionally, we highlighted specific structural features within the 12-membered cytochalasin subclass that may play a role in directing the reversibility of these compounds. Full article

(This article belongs to the Special Issue Natural Products: Extraction, Analysis and Biological Activities)

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10 pages, 3189 KiB

Open AccessArticle

Anti-Melanogenic Effects of L-Theanine on B16F10 Cells and Zebrafish

by Chih-Li Yu, Haiyue Pang, Zhao Run and Guey-Horng Wang

Molecules 2025, 30(4), 956; https://doi.org/10.3390/molecules30040956 - 19 Feb 2025

Viewed by 264

Abstract

L-Theanine, a natural amino acid found in green tea (Camellia sinensis) leaves, is known for its diverse psychotropic effects. This study aimed to evaluate the inhibitory effect of L-theanine on melanin production and uncover its regulatory mechanism. We evaluated the anti-melanogenic [...] Read more.

L-Theanine, a natural amino acid found in green tea (Camellia sinensis) leaves, is known for its diverse psychotropic effects. This study aimed to evaluate the inhibitory effect of L-theanine on melanin production and uncover its regulatory mechanism. We evaluated the anti-melanogenic activities of L-theanine in vitro and in vivo. In B16F10 murine melanoma cells induced by α-melanocyte-stimulating hormone, melanin content and intracellular tyrosinase activity were determined, and melanogenesis-related protein expression and signaling pathways were analyzed by Western blotting. Melanin reduction was further assessed using the zebrafish (Danio rerio) test. L-Theanine reduced the intracellular tyrosinase activity and melanin content of B16F10 cells. It also attenuated the expression of melanogenesis-related proteins, such as microphthalmia- associated transcription factor, tyrosinase (TYR), TYR-related protein-1, and dopachrome tautomerase. L-Theanine modulated the protein kinase A (PKA), cAMP responder element binding protein (CREB), phosphorylation of/protein kinase B (Akt), glycogen synthase kinase-3β (GSK-3β), and β-catenin. The antimelanogenic activity of L-theanine (<2 mg/mL) was further confirmed using zebrafish larvae. L-Theanine inhibited melanogenesis by downregulating the PKA/CREB and Akt/GSK-3β/β-catenin signaling pathways. In summary, L-theanine shows potential as a skin-whitening compound, warranting further investigation for its possible applications in cosmetic and pharmaceutical products. Full article

(This article belongs to the Special Issue Functional Molecules as Novel Cosmetic Ingredients)

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14 pages, 1683 KiB

Open AccessArticle

Natural Polyamine Spermidine Inhibits the In Vitro Oxidation of LDL

by Christine Rossmann, Azra Darko, Gerd Kager, Gerhard Ledinski, Willibald Wonisch, Thomas Wagner, Seth Hallström, Gilbert Reibnegger, Margret Paar and Gerhard Cvirn

Molecules 2025, 30(4), 955; https://doi.org/10.3390/molecules30040955 - 19 Feb 2025

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Abstract

Spermidine is a natural autophagy-inducer and anti-aging compound. Herein, we investigated a potential autophagy-independent mechanism of spermidine, namely its capability to directly impede LDL oxidation, an early step in atherogenesis. In our in vitro-model, LDL oxidation was induced by the addition of CuCl [...] Read more.

Spermidine is a natural autophagy-inducer and anti-aging compound. Herein, we investigated a potential autophagy-independent mechanism of spermidine, namely its capability to directly impede LDL oxidation, an early step in atherogenesis. In our in vitro-model, LDL oxidation was induced by the addition of CuCl₂ in the presence of increasing concentrations of spermidine, and the degree of oxidation of the lipid, as well as of the protein part of LDL, was measured. We found that spermidine concentration-dependently inhibited the production of lipid hydroperoxides, malondialdehyde, and oxidation-specific immune epitopes in the LDL particle, associated with decreased relative electrophoretic mobilities, respectively. For example, the LPO content was significantly lower when LDL was oxidized in the presence of 500 µg/mL spermidine (26.9 ± 1.6 nmol/mg LDL) than in the absence of spermidine (180.6 ± 7.7 nmol/mg LDL, p < 0.0001). When oxLDL was obtained under increasing spermidine concentrations, its cytotoxicity in EA.hy926 cells concentration-dependently decreased. Quantum chemical calculations show that the reaction between spermidine and hydroxyl radicals is exergonic. We conclude that spermidine is a direct inhibitor of LDL oxidation due to its capability to scavenge hydroxyl radicals. Thus, spermidine supplementation might be a suitable tool to impede atherogenesis and associated (cardio)vascular diseases. Further prospective clinical studies are needed to evaluate the potential atheroprotective/health-promoting effects of spermidine-rich diets. Full article

(This article belongs to the Section Medicinal Chemistry)

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14 pages, 109001 KiB

Open AccessArticle

Construction and Regulation of Polymer@Silica Microspheres with Double-Shell Hollow Structures

by Mingxiu Jiang, Yuanyuan Yang, Jiawei Feng, Zhaopan Wang and Wei Deng

Molecules 2025, 30(4), 954; https://doi.org/10.3390/molecules30040954 - 18 Feb 2025

Viewed by 263

Abstract

Microspheres with well-defined hollow structures have been attracting interest due to their unique morphology and fascinating properties. Herein, a strategy for morphology and size control of hollow polymer@silica microspheres is proposed. Multilayer core–shell polymer microspheres, containing substantial carboxyl groups inside, evolve into microspheres [...] Read more.

Microspheres with well-defined hollow structures have been attracting interest due to their unique morphology and fascinating properties. Herein, a strategy for morphology and size control of hollow polymer@silica microspheres is proposed. Multilayer core–shell polymer microspheres, containing substantial carboxyl groups inside, evolve into microspheres with a 304 nm hollow structure after alkali treatment, which are used to construct hollow polymer@silica microspheres by coating the inorganic layer using the layer-by-layer (LBL) and sol–gel methods, respectively. The inorganic shell thickness of hollow polymer@silica microspheres can be adjusted from 15 nm to 33 nm by the self-assembled layers in the LBL method and from 15 nm to 63 nm by the dosage of precursor in the sol–gel method. Compared to the LBL method, the hollow polymer@silica microspheres prepared via the sol–gel method have a uniform and dense inorganic shell, thus ensuring the complete spherical morphology of the microspheres after calcination, even if the inorganic shell thickness is only 15 nm. Moreover, the hollow polymer@silica microspheres prepared via the sol–gel method exhibit improved compression resistance and good opacity, remaining intact at 16,000 psi and providing the corresponding coating with transmittance lower than 35.1%. This work highlights the morphology regulation of microspheres prepared by different methods and provides useful insights for the design of composites microspheres with controllable structures. Full article

(This article belongs to the Special Issue Heterophase Polymerization and Functional Polymer Microspheres/Microcapsules)

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13 pages, 10501 KiB

Open AccessArticle

Rational Design of Metal-Free Nitrogen-Doped Carbon for Controllable Reduction of CO₂ to Syngas

by Guangbin An, Kang Wang, Min Yang, Jiye Zhang, Haijian Zhong, Liang Wang and Huazhang Guo

Molecules 2025, 30(4), 953; https://doi.org/10.3390/molecules30040953 - 18 Feb 2025

Viewed by 301

Abstract

The electrocatalytic reduction of CO₂ (ECO₂RR) to syngas with tunable CO/H₂ ratios offers a promising route for sustainable energy conversion and chemical production. Here, we report a series of N-doped carbon black (NCBx) catalysts with tailored nitrogen species that [...] Read more.

The electrocatalytic reduction of CO₂ (ECO₂RR) to syngas with tunable CO/H₂ ratios offers a promising route for sustainable energy conversion and chemical production. Here, we report a series of N-doped carbon black (NCBx) catalysts with tailored nitrogen species that enable precise control over the composition of syngas. Among the catalysts, NCB3 exhibits the optimal performance, achieving high CO selectivity (64.14%) and activity (1.9 mA cm⁻²) in an H-type cell at −0.9 V. Furthermore, NCB3 produces syngas with a wide range of CO/H₂ ratios (0.52 to 4.77) across the applied potentials (−0.5 to −1.0 V). Stability tests confirm the robust durability of NCB3, which maintains consistent activity and selectivity over prolonged electrolysis. This work demonstrates the critical role of nitrogen species in tuning ECO₂RR pathways and establishes a strategy for designing efficient and stable carbon-based catalysts for CO₂ utilization and syngas production. Full article

(This article belongs to the Special Issue Inorganic/Organic Catalysts: Moving towards an Efficient, Green, and Sustainable Future)

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15 pages, 1710 KiB

Open AccessArticle

Profiling and Bioactivity of Polyphenols from the Omani Medicinal Plant Terminalia dhofarica (syn. Anogeissus dhofarica)

by Jonas Kappen, Luay Rashan, Katrin Franke and Ludger A. Wessjohann

Molecules 2025, 30(4), 952; https://doi.org/10.3390/molecules30040952 - 18 Feb 2025

Viewed by 297

Abstract

Several polyphenol-rich Terminalia species (Combretaceae) are known to accelerate wound healing. Recently, the Omani medicinal plant Anogeissus dhofarica (now Terminalia dhofarica) was attributed to the genus Terminalia based on phylogenetic studies. Leaves, bark, and extracts of T. dhofarica are traditionally used for [...] Read more.

Several polyphenol-rich Terminalia species (Combretaceae) are known to accelerate wound healing. Recently, the Omani medicinal plant Anogeissus dhofarica (now Terminalia dhofarica) was attributed to the genus Terminalia based on phylogenetic studies. Leaves, bark, and extracts of T. dhofarica are traditionally used for various medicinal purposes, including wound treatment and personal hygiene. In the present study, the phytochemical profile of leaves from T. dhofarica was evaluated by ultra-high-performance liquid chromatography coupled with electrospray ionization high-resolution mass spectrometry (UHPLC-ESI-HRMS) and nuclear magnetic resonance (NMR) spectroscopy. Simple phenolics, polyphenolics (e.g., flavonoids and tannins) and their glucosides were characterized as major metabolite classes. In addition, 20 phenolics were isolated and structurally identified. Nine of these compounds were never described before for T. dhofarica. For the first time, we provide complete NMR data for 1-O-galloyl-6-O-p-coumaroyl-d-glucose (1). Biological screening demonstrated moderate efficacy against the Gram-negative bacterium Aliivibrio fischeri, the phytopathogenic fungus Septoria tritici, and the oomycete Phytophthora infestans. In summary, the data expand the knowledge of the phytochemistry of the underexplored species T. dhofarica and underscore its potential for therapeutic applications, particularly in the context of traditional medicine. Full article

(This article belongs to the Special Issue Natural Polyphenols in Human Health (Volume II))

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18 pages, 5607 KiB

Open AccessArticle

Effect of the Positioning of Metal Centers on a Cavitand in the Ruthenium-Catalyzed N-Alkylation of Amines

by Neslihan Şahin, Christophe Gourlaouen and David Sémeril

Molecules 2025, 30(4), 951; https://doi.org/10.3390/molecules30040951 - 18 Feb 2025

Viewed by 178

Abstract

Two bis-ruthenium(II) complexes, namely N,N′-{5,17-diamino-4(24),6(10),12(16),18(22)-tetramethylenedioxy-2,8,14,20-tetrapentylresorcin[4]arene}-bis-[dichloro-(p-cymene)-ruthenium(II)] (1) and N,N′-{5,11-diamino-4(24),6(10),12(16), 18(22)-tetramethylenedioxy-2,8,14,20-tetrapentylresorcin[4]arene}-bis-[dichloro-(p-cymene)-ruthenium(II)] (2) were synthesized and tested as catalysts in the N-alkylation of primary amines with arylmethyl alcohol using the green [...] Read more.

Two bis-ruthenium(II) complexes, namely N,N′-{5,17-diamino-4(24),6(10),12(16),18(22)-tetramethylenedioxy-2,8,14,20-tetrapentylresorcin[4]arene}-bis-[dichloro-(p-cymene)-ruthenium(II)] (1) and N,N′-{5,11-diamino-4(24),6(10),12(16), 18(22)-tetramethylenedioxy-2,8,14,20-tetrapentylresorcin[4]arene}-bis-[dichloro-(p-cymene)-ruthenium(II)] (2) were synthesized and tested as catalysts in the N-alkylation of primary amines with arylmethyl alcohol using the green “hydrogen borrowing” methodology. The catalytic results were compared with those obtained when the N-{5-amino-4(24),6(10),12(16),18(22)-tetramethylenedioxy-2,8,14,20-tetrapentyl-resorcin[4]arene}-[dichloro-(p-cymene)-ruthenium(II)] (3) complex was employed as catalyst. The rate of the N-alkylation of aniline with benzyl alcohol increased in the order 3 < 1 ≪ 2, which highlights the importance of the relative positioning of the two metal centers on the upper rim of the resorcin[4]arene. Theoretical investigations suggest that the grafting of the two “RuCl₂(p-cymene)NH₂” moieties on two distal aromatic rings of the cavitand allows a cooperative effect between a ruthenium atom and the coordinated amine of the second metal center. Full article

(This article belongs to the Section Organometallic Chemistry)

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13 pages, 2884 KiB

Open AccessArticle

The Production and Characterization of an Aminolyzed Polyhydroxyalkanoate Membrane and Its Cytocompatibility with Osteoblasts

by Qiulan Luo, Fuming Zou, Dongjuan Yang, Yongping Huang, Dajie Xian, Ying Nie, Zhenxia Zhang, Yuzhong Zheng, Yaqun Liu, Fei Zhou, Peikui Yang, Yuting Jiang, Xianjing Huang and Xianghui Zou

Molecules 2025, 30(4), 950; https://doi.org/10.3390/molecules30040950 - 18 Feb 2025

Viewed by 197

Abstract

Polyhydroxyalkanoates (PHAs), recognized as a medical biomaterial, have been proven to promote cell proliferation and tissue repair. PHA has a variety of forms: PHB, PHV, PHHx, and PHBHHx, etc. In this study, PHBHHx was selected as the precursor to fabricate biopolyester films. Specifically, [...] Read more.

Polyhydroxyalkanoates (PHAs), recognized as a medical biomaterial, have been proven to promote cell proliferation and tissue repair. PHA has a variety of forms: PHB, PHV, PHHx, and PHBHHx, etc. In this study, PHBHHx was selected as the precursor to fabricate biopolyester films. Specifically, a novel type of biopolyester film was generated through an ammonolysis cross-linking reaction in conjunction with polyamidoamine dendrimer G2.0 (PAMAM). The properties of the resultant biopolyester films were comprehensively evaluated, encompassing surface characteristics, amino group content, and water contact angle. The drug-loading properties and compatibility with osteoblasts of the biopolyester films were also determined. The findings revealed that following aminolysis, the biopolyester film surface exhibited enhanced roughness and an enlarged surface area. Moreover, as the aminolysis duration extended, the hydrophilicity and drug-loading efficiency were significantly augmented. Post-aminolysis, the PHBHHx membrane exhibited a more favorable environment for the adhesion and proliferation of osteoblasts. Overall, the biopolyester film developed in this study provides novel insights and materials for tissue engineering, especially bone tissue repair. Full article

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15 pages, 2620 KiB

Open AccessArticle

Structural Identification of Physalis alkekengi L. Polysaccharides

by Yun Zhang, Xuan Wen, Neng Xu, Hongyan Fu, Ge Lv, Wenjie Yu, Lina Wei and Lin Zhao

Molecules 2025, 30(4), 949; https://doi.org/10.3390/molecules30040949 - 18 Feb 2025

Viewed by 207

Abstract

Physalis alkekengi L. fruit polysaccharides can reduce blood sugar, regulate blood lipids, and improve intestinal flora structure. However, the specific polysaccharide components exerting these effects are unclear. In this study, we extracted, separated, purified, and characterized the P. alkekengi polysaccharides Phy-1a, Phy-1b, and [...] Read more.

Physalis alkekengi L. fruit polysaccharides can reduce blood sugar, regulate blood lipids, and improve intestinal flora structure. However, the specific polysaccharide components exerting these effects are unclear. In this study, we extracted, separated, purified, and characterized the P. alkekengi polysaccharides Phy-1a, Phy-1b, and Phy-1c. Ion chromatography showed that Phy-1b was mainly composed of rhamnose, arabinose, galactose, glucose, and xylose at a molar ratio of 3.0:19.8:47.5:20.9:8.8, and Phy-1c was composed of rhamnose, arabinose, galactose, glucose, xylose, mannose, ribose Galactosamine hydrochloride and Glucosamine hydrochloride at a molar ratio of 10.4:7.9:22.8:30.5:4.6:4.4:19.4:3.9:5.8. Neither of these polysaccharides contained uronic acid, indicating their neutral property. Methylation analysis and nuclear magnetic resonance spectroscopy showed that Phy-1b was mainly composed of terminal sugars (1-Araf); 1,5-Araf; 1,4-Xylp; 1-Glcp; 2,4-Rhap; 1,3-Glcp; 1,4-Galp; 1,4-Glcp; 1,3-Galp; 1,6-Glcp; 1,3,6-Glcp; and 1,4,6-Galp at a molar ratio of 5.2:7.1:7.8:13.7:6.3:11.2:7.0:16.3:7.4:6.0:6.8:5.3, with the main chain being →2)-α-L-Rhap-(1→4)-β-d-Galp-(1→4)-β-d-Galp-(1→[3)-β-d-Glcp-(1]2→3)-β-d-Glcp-(1→[4)-β-d-Glcp-(1]2→ and the branched chains being β-L-Araf-(1→5)-β-L-Araf-(1→, β-d-Glcp-(1→4)-β-d-Xylp-(1→ 3)-β-d-Galp-(1→, and β-d-Glcp-(1→6)-β-d-Glcp-(1→. The three fragments, respectively, pass through the O-4 key of →2,4)-α-l-Rhap-(1→, O-6 key of →4,6)-β-d-Galp-(1→, and O-6 of →3,6)-β-d-Glcp-(1→ connected to the main chain. These results provide a reference for enhancing the utilization value of P. alkekengi resources to promote its high-value and efficient processing. Full article

(This article belongs to the Special Issue Activity and Structural Characteristics of Polysaccharides)

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26 pages, 7079 KiB

Open AccessArticle

An Appealing, Robust Access to Furo-Fused Heteropolycycles

by Alice Benzi, Lara Bianchi, Gianluca Giorgi, Giovanni Lentini, Massimo Maccagno, Guglielmo Marcantoni Taddei, Giovanni Petrillo and Cinzia Tavani

Molecules 2025, 30(4), 948; https://doi.org/10.3390/molecules30040948 - 18 Feb 2025

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Abstract

Recently, nitrostilbenes characterized by two different or differently substituted aryl moieties, obtainable from the initial ring-opening of 3-nitrobenzo[b]thiophene with amines, have proved, by means of a stepwise double coupling with phenolic-type bidentate C/O nucleophiles, to be valuable precursors of oxygen-containing heteropolycycles [...] Read more.

Recently, nitrostilbenes characterized by two different or differently substituted aryl moieties, obtainable from the initial ring-opening of 3-nitrobenzo[b]thiophene with amines, have proved, by means of a stepwise double coupling with phenolic-type bidentate C/O nucleophiles, to be valuable precursors of oxygen-containing heteropolycycles and of fully conjugated systems therefrom via an efficient 6π-electrocyclization and final aromatization. Herein, the methodology is extended, after suitable optimization, to diverse heterophenols to afford new appealing heteropolycyclic systems of potential interest as drug leads. The synthetic results are fully consistent with up-to-date quantomechanical calculations. For some of the new molecules, a significant fluorescence is reported, with a potential for future applications, e.g., in the field of optical devices. Full article

(This article belongs to the Special Issue Heterocyclic Compounds for Drug Design and Drug Discovery)

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14 pages, 1204 KiB

Open AccessReview

From Origin to the Present: Establishment, Mechanism, Evolutions and Biomedical Applications of the CRISPR/Cas-Based Macromolecular System in Brief

by Zheng Yuan

Molecules 2025, 30(4), 947; https://doi.org/10.3390/molecules30040947 - 18 Feb 2025

Viewed by 679

Abstract

Advancements in biological and medical science are intricately linked to the biological central dogma. In recent years, gene editing techniques, especially CRISPR/Cas systems, have emerged as powerful tools for modifying genetic information, supplementing the central dogma and holding significant promise for disease diagnosis [...] Read more.

Advancements in biological and medical science are intricately linked to the biological central dogma. In recent years, gene editing techniques, especially CRISPR/Cas systems, have emerged as powerful tools for modifying genetic information, supplementing the central dogma and holding significant promise for disease diagnosis and treatment. Extensive research has been conducted on the continuously evolving CRISPR/Cas systems, particularly in relation to challenging diseases, such as cancer and HIV infection. Consequently, the integration of CRISPR/Cas-based techniques with contemporary medical approaches and therapies is anticipated to greatly enhance healthcare outcomes for humans. This review begins with a brief overview of the discovery of the CRISPR/Cas system. Subsequently, using CRISPR/Cas9 as an example, a clear description of the classical molecular mechanism underlying the CRISPR/Cas system was given. Additionally, the development of the CRISPR/Cas system and its applications in gene therapy and high-sensitivity disease diagnosis were discussed. Furthermore, we address the prospects for clinical applications of CRISPR/Cas-based gene therapy, highlighting the ethical considerations associated with altering genetic information. This brief review aims to enhance understanding of the CRISPR/Cas macromolecular system and provide insight into the potential of genetic macromolecular drugs for therapeutic purposes. Full article

(This article belongs to the Section Chemical Biology)

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23 pages, 409 KiB

Open AccessArticle

Diplopterys pubipetala (Malpighiaceae): Insights into Antioxidant, Antibacterial, and Antifungal Activities with Chemical Composition Analysis via UHPLC-MS/MS and GC/MS

by Veronica de Melo Sacramento, Vanessa de Andrade Royo, Pedro Henrique Fonseca Veloso, Kamila Soares Freitas Souto, Alisson Samuel Portes Caldeira, Carlos Henrique Gomes Martins, Sara Lemes de Souza, Ezequias Pessoa de Siqueira, Fernando Ribeiro Cassiano, Afrânio Farias de Melo Júnior, Dario Alves de Oliveira, Elytania Veiga Mnezes and Tânia Maria de Almeida Alves

Molecules 2025, 30(4), 946; https://doi.org/10.3390/molecules30040946 - 18 Feb 2025

Viewed by 316

Abstract

Diplopterys pubipetala (Malpighiaceae) is a liana native to the Brazilian Cerrado biome, traditionally used in Ayahuasca preparations. Despite its cultural importance, research on its chemical composition and biological activities, which may have therapeutic potential, is limited. This study investigated the volatile and non-volatile [...] Read more.

Diplopterys pubipetala (Malpighiaceae) is a liana native to the Brazilian Cerrado biome, traditionally used in Ayahuasca preparations. Despite its cultural importance, research on its chemical composition and biological activities, which may have therapeutic potential, is limited. This study investigated the volatile and non-volatile secondary metabolites of D. pubipetala leaves, their antioxidant capacity, and their antibacterial and antifungal activities. Volatile compounds were identified using gas chromatography-mass spectrometry (GC-MS) coupled to solid-phase microextraction (SPME), while non-volatile compounds were annotated using UHPLC-MS/MS-ESI-Q-TOF. Antioxidant capacity was evaluated by DPPH assay, and antimicrobial activity was assessed in vitro against Staphylococcus aureus, Escherichia coli, Pseudomonas aeruginosa, and Candida species (C. albicans, C. tropicalis, C. glabrata). GC-MS analysis revealed 25 predominant volatile compounds, including ethyl dodecanoate, ethyl tetradecanoate, nonanoic acid, and 5-methylhexan-2-one, with documented antifungal, antioxidant, and antimicrobial activities. The crude extract and ethyl acetate fraction showed strong antioxidant capacity (EC₅₀ 9.83 µg/mL and 6.42 µg/mL, respectively), and antifungal effects were observed against Candida species. This study provides the first comprehensive investigation of the antioxidant capacity and antibacterial and antifungal activities of D. pubipetala, together with a detailed chemical profile of its volatile compounds. Full article

(This article belongs to the Special Issue Phytochemistry and Biological Activity Perspectives of Medicinal Plants)

18 pages, 2046 KiB

Open AccessArticle

Dynamic Environmental Interactions Shape the Volatile Compounds of Agarwood Oils Extracted from Aquilaria sinensis Using Supercritical Carbon Dioxide

by Wenxian Zhang, Sizhu Qian, Dehuai Wu, Qiaoling Yan, Jen-Ping Chung and Yongmei Jiang

Molecules 2025, 30(4), 945; https://doi.org/10.3390/molecules30040945 - 18 Feb 2025

Viewed by 342

Abstract

Aquilaria spp. are a highly valuable plant species found in the Chinese herbal medicine and agarwood fragrance supplement industries for fumigation, combustion and perfume. The phytochemical composition of agarwood oils (extracts) was derived from Aquilaria sinensis and its subspecies ‘Qi-Nan’ using supercritical CO [...] Read more.

Aquilaria spp. are a highly valuable plant species found in the Chinese herbal medicine and agarwood fragrance supplement industries for fumigation, combustion and perfume. The phytochemical composition of agarwood oils (extracts) was derived from Aquilaria sinensis and its subspecies ‘Qi-Nan’ using supercritical CO₂ extraction technology. Gas chromatography connected with a mass spectrometry apparatus was employed for qualitative and quantitative analyses. Comparing the agarwood oils from six planting areas, 12 common components were obtained, among which sesquiterpenes and chromones had the highest relative content. Genetic and environmental factors had the greatest impact on the three chromones, especially on 2-phenyl-4H-chromen-4-one. According to the PCA and PLS-DA models, the ‘Qi-Nan’ was derived from a variety selected from the native A. sinensis, and the difference in the volatile components was able to indirectly prove that it was genetically heterogeneous with the native A. sinensis. Using the 73 components obtained from GC–MS analysis, the VIP values and S-plots were generated using the OPLS-DA model. Seven components with VIP values > 1.0 were selected from two groups of agarwood oils of the native A. sinensis and ‘Qi-Nan’ subspecies. In addition, by analyzing 12 common components, the differential components with VIP values > 1 were 2-phenyl-4H-chromen-4-one and 2-(4-methoxyphenethyl)-4H-chromen-4-one. Chromones were the main component of agarwood oils extracted by supercritical CO₂, and 2-phenyl-4H-chromen-4-one could be used as a volatile marker, especially in the ‘Qi-Nan’ subspecies, where this marker exhibited more prominent characteristics. Full article

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