Molecules

12 pages, 1146 KiB

Open AccessArticle

Total Synthesis of the Racemate of Laurolitsine

by Mingyu Cao, Yiming Wang, Yong Zhang, Caiyun Zhang, Niangen Chen and Xiaopo Zhang

Molecules 2024, 29(3), 745; https://doi.org/10.3390/molecules29030745 - 5 Feb 2024

Viewed by 1175

The total synthesis of laurolitsine was achieved for the first time. This reaction was accomplished in 14 steps with a 2.3% yield (this was calculated using 3-hydroxy-4-methoxybenzaldehyde as the starting material) starting from two simple materials, 3-hydroxy-4-methoxybenzaldehyde and 2-(3-hydroxy-4-methoxyphenyl)acetic acid, and the longest [...] Read more.

The total synthesis of laurolitsine was achieved for the first time. This reaction was accomplished in 14 steps with a 2.3% yield (this was calculated using 3-hydroxy-4-methoxybenzaldehyde as the starting material) starting from two simple materials, 3-hydroxy-4-methoxybenzaldehyde and 2-(3-hydroxy-4-methoxyphenyl)acetic acid, and the longest linear sequence consisted of 11 steps. The key steps included an electrophilic addition reaction in which a nitro group was reduced to an amino group using lithium tetrahydroaluminum and a Pd-catalyzed direct biaryl coupling reaction. In this paper, many of the experimental steps were optimized, and an innovative postprocessing method in which 2-(3-(benzyloxy)-4-methoxyphenyl)ethanamine is salted with oxalic acid was proposed. Full article

(This article belongs to the Section Medicinal Chemistry)

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15 pages, 5192 KiB

Open AccessArticle

A Portable Electrochemical Dopamine Detector Using a Fish Scale-Derived Graphitized Carbon-Modified Screen-Printed Carbon Electrode

by Feng Yang, Xiao Han, Yijing Ai, Bo Shao, Weipin Ding, Kai Tang and Wei Sun

Molecules 2024, 29(3), 744; https://doi.org/10.3390/molecules29030744 - 5 Feb 2024

Cited by 1 | Viewed by 1296

Abstract

In this paper, a highly conductive alkali-activated graphitized carbon (a-GC) was prepared using tilapia fish scales as precursors through enzymolysis, activation and pyrolytic carbonization methods. The prepared a-GC was modified on the surface of a screen-printed carbon electrode to construct a flexible portable [...] Read more.

In this paper, a highly conductive alkali-activated graphitized carbon (a-GC) was prepared using tilapia fish scales as precursors through enzymolysis, activation and pyrolytic carbonization methods. The prepared a-GC was modified on the surface of a screen-printed carbon electrode to construct a flexible portable electrochemical sensing platform, which was applied to the differential pulse voltametric detection of dopamine (DA) using a U-disk electrochemical workstation combined with a smart phone and Bluetooth. The prepared a-GC possesses good electrical conductivity, a large specific surface area and abundant active sites, which are beneficial for the electrooxidation of DA molecules and result in excellent sensitivity and high selectivity for DA analysis. Under the optimal conditions, the oxidation peak current of DA increased gradually, with its concentrations in the range from 1.0 μmol/L to 1000.0 μmol/L, with the detection limit as low as 0.25 μmol/L (3S/N). The proposed sensor was further applied to the determination of DA in human sweat samples, with satisfactory results, which provided an opportunity for developing noninvasive early diagnosis and nursing equipment. Full article

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17 pages, 3144 KiB

Open AccessArticle

Egg White Protein–Proanthocyanin Complexes Stabilized Emulsions: Investigation of Physical Stability, Digestion Kinetics, and Free Fatty Acid Release Dynamics

by Ting Zhang, Shanglin Li, Meng Yang, Yajuan Li, Xuanting Liu, Xiaomin Shang, Jingbo Liu, Zhiyang Du and Ting Yu

Molecules 2024, 29(3), 743; https://doi.org/10.3390/molecules29030743 - 5 Feb 2024

Cited by 3 | Viewed by 1953

Abstract

Egg white proteins pose notable limitations in emulsion applications due to their inadequate wettability and interfacial instability. Polyphenol-driven alterations in proteins serve as an effective strategy for optimizing their properties. Herein, covalent and non-covalent complexes of egg white proteins-proanthocyanins were synthesized. The analysis [...] Read more.

Egg white proteins pose notable limitations in emulsion applications due to their inadequate wettability and interfacial instability. Polyphenol-driven alterations in proteins serve as an effective strategy for optimizing their properties. Herein, covalent and non-covalent complexes of egg white proteins-proanthocyanins were synthesized. The analysis of structural alterations, amino acid side chains and wettability was performed. The superior wettability (80.00° ± 2.23°) and rigid structure (2.95 GPa) of covalent complexes established favorable conditions for their utilization in emulsions. Furthermore, stability evaluation, digestion kinetics, free fatty acid (FFA) release kinetics, and correlation analysis were explored to unravel the impact of covalent and non-covalent modification on emulsion stability, dynamic digestion process, and interlinkages. Emulsion stabilized by covalent complex exhibited exceptional stabilization properties, and FFA release kinetics followed both first-order and Korsmeyer–Peppas models. This study offers valuable insights into the application of complexes of proteins-polyphenols in emulsion systems and introduces an innovative approach for analyzing the dynamics of the emulsion digestion process. Full article

(This article belongs to the Special Issue Modifications of Biomacromolecules and Their Structure with Functional Properties)

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18 pages, 664 KiB

Open AccessArticle

Physicochemical Properties of Dried and Powdered Pear Pomace

by Anna Krajewska, Dariusz Dziki, Mustafa Abdullah Yilmaz and Fethi Ahmet Özdemir

Molecules 2024, 29(3), 742; https://doi.org/10.3390/molecules29030742 - 5 Feb 2024

Cited by 7 | Viewed by 1691

Abstract

Pear pomace, a byproduct of juice production, represents a valuable reservoir of bioactive compounds with potential health benefits for humans. This study aimed to evaluate the influence of drying method and temperature on pear pomace, specifically focusing on the drying kinetics, grinding characteristics, [...] Read more.

Pear pomace, a byproduct of juice production, represents a valuable reservoir of bioactive compounds with potential health benefits for humans. This study aimed to evaluate the influence of drying method and temperature on pear pomace, specifically focusing on the drying kinetics, grinding characteristics, color, phenolic profile (LC-MS/MS), and antioxidant activities of the powder. Drying using the contact method at 40 °C with microwave assistance demonstrated the shortest duration, whereas freeze-drying was briefer compared to contact-drying without microwave assistance. Freeze-drying resulted in brighter and more easily comminuted pomace. Lyophilized samples also exhibited higher total phenolic compound levels compared to contact-dried ones, correlating with enhanced antioxidant activity. Twenty-one phenolic compounds were identified, with dominant acids being quinic, chlorogenic, and protocatechuic. Flavonoids, primarily isoquercitrin, and rutin, were also presented. Pear pomace dried via contact at 60 °C contained more quinic and protocatechuic acids, while freeze-dried pomace at the same temperature exhibited higher levels of chlorogenic acid, epicatechin, and catechin. The content of certain phenolic components, such as gallic acid and epicatechin, also varied depending on the applied drying temperature. Full article

(This article belongs to the Section Food Chemistry)

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13 pages, 738 KiB

Open AccessReview

Phlorizin, an Important Glucoside: Research Progress on Its Biological Activity and Mechanism

by Tongjia Ni, Shuai Zhang, Jia Rao, Jiaqi Zhao, Haiqi Huang, Ying Liu, Yue Ding, Yaqian Liu, Yuchi Ma, Shoujun Zhang, Yang Gao, Liqian Shen, Chuanbo Ding and Yunpeng Sun

Molecules 2024, 29(3), 741; https://doi.org/10.3390/molecules29030741 - 5 Feb 2024

Cited by 4 | Viewed by 2459

Abstract

Phlorizin, as a flavonoid from a wide range of sources, is gradually becoming known for its biological activity. Phlorizin can exert antioxidant effects by regulating the IL-1β/IKB-α/NF-KB signaling pathway. At the same time, it exerts its antibacterial activity by reducing intracellular DNA agglutination, [...] Read more.

Phlorizin, as a flavonoid from a wide range of sources, is gradually becoming known for its biological activity. Phlorizin can exert antioxidant effects by regulating the IL-1β/IKB-α/NF-KB signaling pathway. At the same time, it exerts its antibacterial activity by reducing intracellular DNA agglutination, reducing intracellular protein and energy synthesis, and destroying intracellular metabolism. In addition, phlorizin also has various pharmacological effects such as antiviral, antidiabetic, antitumor, and hepatoprotective effects. Based on domestic and foreign research reports, this article reviews the plant sources, extraction, and biological activities of phlorizin, providing a reference for improving the clinical application of phlorizin. Full article

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29 pages, 12870 KiB

Open AccessArticle

Multiscale Modeling of Macromolecular Interactions between Tau-Amylin Oligomers and Asymmetric Lipid Nanodomains That Link Alzheimer’s and Diabetic Diseases

by Natalia Santos, Luthary Segura, Amber Lewis, Thuong Pham and Kwan H. Cheng

Molecules 2024, 29(3), 740; https://doi.org/10.3390/molecules29030740 - 5 Feb 2024

Cited by 2 | Viewed by 1885

Abstract

The molecular events of protein misfolding and self-aggregation of tau and amylin are associated with the progression of Alzheimer’s and diabetes, respectively. Recent studies suggest that tau and amylin can form hetero-tau-amylin oligomers. Those hetero-oligomers are more neurotoxic than homo-tau oligomers. So far, [...] Read more.

The molecular events of protein misfolding and self-aggregation of tau and amylin are associated with the progression of Alzheimer’s and diabetes, respectively. Recent studies suggest that tau and amylin can form hetero-tau-amylin oligomers. Those hetero-oligomers are more neurotoxic than homo-tau oligomers. So far, the detailed interactions between the hetero-oligomers and the neuronal membrane are unknown. Using multiscale MD simulations, the lipid binding and protein folding behaviors of hetero-oligomers on asymmetric lipid nanodomains or raft membranes were examined. Our raft membranes contain phase-separated phosphatidylcholine (PC), cholesterol, and anionic phosphatidylserine (PS) or ganglioside (GM1) in one leaflet of the lipid bilayer. The hetero-oligomers bound more strongly to the PS and GM1 than other lipids via the hydrophobic and hydrophilic interactions, respectively, in the raft membranes. The hetero-tetramer disrupted the acyl chain orders of both PC and PS in the PS-containing raft membrane, but only the GM1 in the GM1-containing raft membrane as effectively as the homo-tau-tetramer. We discovered that the alpha-helical content in the heterodimer was greater than the sum of alpha-helical contents from isolated tau and amylin monomers on both raft membranes, indicative of a synergetic effect of tau-amylin interactions in surface-induced protein folding. Our results provide new molecular insights into understanding the cross-talk between Alzheimer’s and diabetes. Full article

(This article belongs to the Special Issue Soft Matter Nanostructures—Fabrication, Interactions and Applications: In Honor of Prof. Dr. Michael Rappolt’s 60th Birthday)

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15 pages, 1461 KiB

Open AccessReview

Hyaluronan: Sources, Structure, Features and Applications

by Katarína Valachová, Mohamed E. Hassan and Ladislav Šoltés

Molecules 2024, 29(3), 739; https://doi.org/10.3390/molecules29030739 - 5 Feb 2024

Cited by 11 | Viewed by 4146

Abstract

Hyaluronan (HA) is a non-sulfated glycosaminoglycan that is present in a variety of body tissues and organs. Hyaluronan has a wide range of biological activities that are frequently influenced by molar mass; however, they also depend greatly on the source, purity, and kind [...] Read more.

Hyaluronan (HA) is a non-sulfated glycosaminoglycan that is present in a variety of body tissues and organs. Hyaluronan has a wide range of biological activities that are frequently influenced by molar mass; however, they also depend greatly on the source, purity, and kind of impurities in hyaluronan. High-molar-mass HA has anti-inflammatory, immunosuppressive, and antiangiogenic properties, while low-molar-mass HA has opposite properties. A number of chemical modifications have been performed to enhance the stability of HA and its applications in medical practice. Hyaluronan is widely applied in medicine, such as viscosupplementation, ophthalmology, otolaryngology, wound healing, cosmetics, and drug delivery. In this review, we summarized several medical applications of polymers based on the hyaluronan backbone. Full article

(This article belongs to the Special Issue Hyaluronan, 2nd Edition)

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16 pages, 2667 KiB

Open AccessArticle

Efficient Scavenging of TEMPOL Radical by Ascorbic Acid in Solution and Related Prolongation of ¹³C and ¹H Nuclear Spin Relaxation Times of the Solute

by Václav Římal, Eleonora I. Bunyatova and Helena Štěpánková

Molecules 2024, 29(3), 738; https://doi.org/10.3390/molecules29030738 - 5 Feb 2024

Viewed by 1167

Abstract

Dynamic nuclear polarization for nuclear magnetic resonance (NMR) spectroscopy and imaging uses free radicals to strongly enhance the NMR signal of a compound under investigation. At the same time, the radicals shorten significantly its nuclear spin relaxation times which reduces the time window [...] Read more.

Dynamic nuclear polarization for nuclear magnetic resonance (NMR) spectroscopy and imaging uses free radicals to strongly enhance the NMR signal of a compound under investigation. At the same time, the radicals shorten significantly its nuclear spin relaxation times which reduces the time window available for the experiments. Radical scavenging can overcome this drawback. Our work presents a detailed study of the reduction of the TEMPOL radical by ascorbic acid in solution by high-resolution NMR. Carbon-13 and hydrogen-1 nuclear spin relaxations are confirmed to be restored to their values without TEMPOL. Reaction mechanism, kinetics, and the influence of pD and viscosity are thoroughly discussed. The detailed investigation conducted in this work should help with choosing suitable concentrations in the samples for dynamic nuclear polarization and optimizing the measurement protocols. Full article

(This article belongs to the Special Issue Stable Radicals: Synthesis and Applications)

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15 pages, 3339 KiB

Open AccessArticle

Combination of a Deep Eutectic Solvent and Macroporous Resin for Green Recovery of Iridoids, Chlorogenic Acid, and Flavonoids from Eucommia ulmoides Leaves

by Yunhui Liao, Feng Chen, Haishan Tang, Wubliker Dessie and Zuodong Qin

Molecules 2024, 29(3), 737; https://doi.org/10.3390/molecules29030737 - 5 Feb 2024

Cited by 3 | Viewed by 1396

Abstract

To increase the effectiveness of using typical biomass waste as a resource, iridoids, chlorogenic acid, and flavonoids from the waste biomass of Eucommia ulmoides leaves (EULs) were extracted by deep eutectic solvents (DESs) in conjunction with macroporous resin. To optimize the extract conditions, [...] Read more.

To increase the effectiveness of using typical biomass waste as a resource, iridoids, chlorogenic acid, and flavonoids from the waste biomass of Eucommia ulmoides leaves (EULs) were extracted by deep eutectic solvents (DESs) in conjunction with macroporous resin. To optimize the extract conditions, the experiment of response surface was employed with the single-factor of DES composition molar ratio, liquid–solid ratio, water percentage, extraction temperature, and extraction time. The findings demonstrated that the theoretical simulated extraction yield of chlorogenic acid (CGA), geniposidic acid (GPA), aucubin (AU), geniposide (GP), rutin (RU), and isoquercetin (IQU) were 42.8, 137.2, 156.7, 5.4, 13.5, and 12.8 mg/g, respectively, under optimal conditions (hydrogen bond donor–hydrogen bond acceptor molar ratio of 1.96, liquid–solid ratio of 28.89 mL/g, water percentage of 38.44%, temperature of 317.36 K, and time of 55.59 min). Then, 12 resins were evaluated for their adsorption and desorption capabilities for the target components, and the HPD950 resin was found to operate at its optimum. Additionally, the HPD950 resin demonstrated significant sustainability and considerable potential in the recyclability test. Finally, the hypoglycemic in vitro, hypolipidemic in vitro, immunomodulatory, and anti-inflammatory effects of EUL extract were evaluated, and the correlation analysis of six active components with biological activity and physicochemical characteristics of DESs by heatmap were discussed. The findings of this study can offer a theoretical foundation for the extraction of valuable components by DESs from waste biomass, as well as specific utility benefits for the creation and development of natural products. Full article

(This article belongs to the Special Issue Biomass-Based Value-Added Bioactive Products: Recovery and Valorization)

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13 pages, 1829 KiB

Open AccessArticle

Organophosphate Triesters and Their Transformation Products in Sediments of Mangrove Wetlands in the Beibu Gulf, South China Sea

by Li Zhang, Yongze Xing, Peng Zhang, Xin Luo and Zengyuan Niu

Molecules 2024, 29(3), 736; https://doi.org/10.3390/molecules29030736 - 5 Feb 2024

Viewed by 1225

Abstract

As emerging pollutants, organophosphate esters (OPEs) have been reported in coastal environments worldwide. Nevertheless, information on the occurrence and ecological risks of OPEs, especially the related transformation products, in mangrove wetlands is scarce. For the first time, the coexistence and distribution of OP [...] Read more.

As emerging pollutants, organophosphate esters (OPEs) have been reported in coastal environments worldwide. Nevertheless, information on the occurrence and ecological risks of OPEs, especially the related transformation products, in mangrove wetlands is scarce. For the first time, the coexistence and distribution of OP triesters and their transformation products in three mangrove wetlands in the Beibu Gulf were investigated using ultrasonication and solid-phase extraction, followed by UHPLC-MS/MS detection. The studied OPEs widely existed in all the sampling sites, with the total concentrations ranging from 6.43 ng/g dry weight (dw) to 39.96 ng/g dw and from 3.33 ng/g dw to 22.50 ng/g dw for the OP triesters and transformation products, respectively. Mangrove wetlands tend to retain more OPEs than the surrounding coastal environment. Pearson correlation analysis revealed that the TOC was not the sole factor in determining the OPEs’ distribution, and degradation was not the main source of the transformation products in mangrove sediments in the Beibu Gulf. The ecological risks of selected OPEs for different organisms were also assessed, revealing a medium to high risk posed by OP diesters to organisms. The levels or coexistence of OPEs and their metabolites in mangroves need constant monitoring, and more toxicity data should be further studied to assess the effect on normal aquatic organisms. Full article

(This article belongs to the Special Issue Analysis of Residues in Environmental Samples II)

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20 pages, 6080 KiB

Open AccessArticle

Enhancement of Female Rat Fertility via Ethanolic Extract from Nigella sativa L. (Black Cumin) Seeds Assessed via HPLC-ESI-MS/MS and Molecular Docking

by Ahmed M. Nagy, Mohamed F. Abdelhameed, Asmaa S. Abd Elkarim, Tushar C. Sarker, Ahmed M. Abd-ElGawad, Abdelsamed I. Elshamy and Abdelmohsen M. Hammam

Molecules 2024, 29(3), 735; https://doi.org/10.3390/molecules29030735 - 5 Feb 2024

Cited by 2 | Viewed by 1862

Abstract

The characteristic chemical composition of Nigella seeds is directly linked to their beneficial properties. This study aimed to investigate the phytochemical composition of Nigella sativa seeds using a 100% ethanolic extract using HPLC-ESI-MS/MS. Additionally, it explored the potential biological effects of the extract [...] Read more.

The characteristic chemical composition of Nigella seeds is directly linked to their beneficial properties. This study aimed to investigate the phytochemical composition of Nigella sativa seeds using a 100% ethanolic extract using HPLC-ESI-MS/MS. Additionally, it explored the potential biological effects of the extract on female rat reproduction. Follicle Stimulating Hormone (FSH), Luteinizing Hormone (LH), Estrogen (E2), and Progesterone (P4) hormone levels were also assessed, along with the morphological and histological effects of the extract on ovarian, oviductal, and uterine tissues. Molecular docking was performed to understand the extract’s activity and its role in regulating female reproduction by assessing its binding affinity to hormonal receptors. Twenty metabolites, including alkaloids, saponins, terpenes, flavonoids, phenolic acids, and fatty acids, were found in the ethanolic extract of N. sativa seeds through the HPLC-ESI-MS/MS study. The N. sativa seed extract exhibited strong estrogenic and LH-like activities (p < 0.05) with weak FSH-like activity. Furthermore, it increased the serum levels of LH (p < 0.05), P4 hormones (p < 0.001), and E2 (p < 0.0001). Molecular docking results displayed a strong interaction with Erβ, LH, GnRH, and P4 receptors, respectively. Based on these findings, N. sativa seeds demonstrated hormone-like activities, suggesting their potential as a treatment for improving female fertility. Full article

(This article belongs to the Special Issue Extraction and Analysis of Natural Product in Food)

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16 pages, 4422 KiB

Open AccessArticle

Porous Electropolymerized Films of Ruthenium Complex: Photoelectrochemical Properties and Photoelectrocatalytic Synthesis of Hydrogen Peroxide

by Hong-Ju Yin and Ke-Zhi Wang

Molecules 2024, 29(3), 734; https://doi.org/10.3390/molecules29030734 - 5 Feb 2024

Viewed by 1156

Abstract

The photoelectrochemical cells (PECs) performing high-efficiency conversions of solar energy into both electricity and high value-added chemicals are highly desirable but rather challenging. Herein, we demonstrate that a PEC using the oxidatively electropolymerized film of a heteroleptic Ru(II) complex of [Ru(bpy)(L) [...] Read more.

The photoelectrochemical cells (PECs) performing high-efficiency conversions of solar energy into both electricity and high value-added chemicals are highly desirable but rather challenging. Herein, we demonstrate that a PEC using the oxidatively electropolymerized film of a heteroleptic Ru(II) complex of [Ru(bpy)(L)₂](PF₆)₂ Ru1 {bpy and L stand for 2,2′-bipyridine and 1-phenyl-2-(4-vinylphenyl)-1H-imidazo[4,5-f][1,10]phenanthroline respectively}, polyRu1, as a working electrode performed both efficient in situ synthesis of hydrogen peroxide and photocurrent generation/switching. Specifically, when biased at −0.4 V vs. saturated calomel electrode and illuminated with 100 mW·cm⁻² white light, the PEC showed a significant cathodic photocurrent density of 9.64 μA·cm⁻². Furthermore, an increase in the concentrations of quinhydrone in the electrolyte solution enabled the photocurrent polarity to switch from cathodic to anodic, and the anodic photocurrent density reached as high as 11.4 μA·cm⁻². Interestingly, in this single-compartment PEC, the hydrogen peroxide yield reached 2.63 μmol·cm⁻² in the neutral electrolyte solution. This study will serve as a guide for the design of high-efficiency metal-complex-based molecular systems performing photoelectric conversion/switching and photoelectrochemical oxygen reduction to hydrogen peroxide. Full article

(This article belongs to the Special Issue Synthesis and Applications of Transition Metal Complexes)

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21 pages, 7224 KiB

Open AccessArticle

African Under-Utilized Medicinal Leafy Vegetables Studied by Microtiter Plate Assays and High-Performance Thin-Layer Chromatography–Planar Assays

by Ibukun O. Oresanya, Ilkay Erdogan Orhan, Julia Heil and Gertrud E. Morlock

Molecules 2024, 29(3), 733; https://doi.org/10.3390/molecules29030733 - 5 Feb 2024

Viewed by 1615

Abstract

Biological activities of six under-utilized medicinal leafy vegetable plants indigenous to Africa, i.e., Basella alba, Crassocephalum rubens, Gnetum africanum, Launaea taraxacifolia, Solanecio biafrae, and Solanum macrocarpon, were investigated via two independent techniques. The total phenolic content (TPC) [...] Read more.

Biological activities of six under-utilized medicinal leafy vegetable plants indigenous to Africa, i.e., Basella alba, Crassocephalum rubens, Gnetum africanum, Launaea taraxacifolia, Solanecio biafrae, and Solanum macrocarpon, were investigated via two independent techniques. The total phenolic content (TPC) was determined, and six microtiter plate assays were applied after extraction and fractionation. Three were antioxidant in vitro assays, i.e., ferric reducing antioxidant power (FRAP), cupric reduction antioxidant capacity (CUPRAC), and 2,2-diphenyl-1-picrylhydrazyl (DPPH) scavenging, and the others were enzyme (acetylcholinesterase, butyrylcholinesterase, and tyrosinase) inhibition assays. The highest TPC and antioxidant activity from all the methods were obtained from polar and medium polar fractions of C. rubens, S. biafrae, and S. macrocarpon. The highest acetyl- and butyrylcholinesterase inhibition was exhibited by polar fractions of S. biafrae, C. rubens, and L. taraxacifolia, the latter comparable to galantamine. The highest tyrosinase inhibition was observed in the n-butanol fraction of C. rubens and ethyl acetate fraction of S. biafrae. In vitro assay results of the different extracts and fractions were mostly in agreement with the bioactivity profiling via high-performance thin-layer chromatography–multi-imaging–effect-directed analysis, exploiting nine different planar assays. Several separated compounds of the plant extracts showed antioxidant, α-glucosidase, α-amylase, acetyl- and butyrylcholinesterase-inhibiting, Gram-positive/-negative antimicrobial, cytotoxic, and genotoxic activities. A prominent apolar bioactive compound zone was tentatively assigned to fatty acids, in particular linolenic acid, via electrospray ionization high-resolution mass spectrometry. The detected antioxidant, antimicrobial, antidiabetic, anticholinesterase, cytotoxic, and genotoxic potentials of these vegetable plants, in particular C. rubens, S. biafrae, and S. macrocarpon, may validate some of their ethnomedicinal uses. Full article

(This article belongs to the Special Issue Discovery of New Functional Foods with Bioactive Compounds)

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14 pages, 2294 KiB

Open AccessArticle

Ameliorative Effects of Zingiber officinale Rosc on Antibiotic-Associated Diarrhea and Improvement in Intestinal Function

by Sung Jin Kim, Myoung-Sook Shin and You-Kyung Choi

Molecules 2024, 29(3), 732; https://doi.org/10.3390/molecules29030732 - 5 Feb 2024

Cited by 3 | Viewed by 1422

Abstract

The global increase in antibiotic consumption is related to increased adverse effects, such as antibiotic-associated diarrhea (AAD). This study investigated the chemical properties of Zingiber officinale Rosc (ZO) extract and its ameliorative effects using a lincomycin-induced AAD mouse model. Intestinal tissues were evaluated [...] Read more.

The global increase in antibiotic consumption is related to increased adverse effects, such as antibiotic-associated diarrhea (AAD). This study investigated the chemical properties of Zingiber officinale Rosc (ZO) extract and its ameliorative effects using a lincomycin-induced AAD mouse model. Intestinal tissues were evaluated for the expression of lysozyme, claudin-1, and α-defensin-1, which are associated with intestinal homeostasis. The cecum was analyzed to assess the concentration of short-chain fatty acids (SCFAs). The chemical properties analysis of ZO extracts revealed the levels of total neutral sugars, acidic sugars, proteins, and polyphenols to be 86.4%, 8.8%, 4.0%, and 0.8%, respectively. Furthermore, the monosaccharide composition of ZO was determined to include glucose (97.3%) and galactose (2.7%). ZO extract administration ameliorated the impact of AAD and associated weight loss, and water intake also returned to normal. Moreover, treatment with ZO extract restored the expression levels of lysozyme, α-defensin-1, and claudin-1 to normal levels. The decreased SCFA levels due to induced AAD showed a return to normal levels. The results indicate that ZO extract improved AAD, strengthened the intestinal barrier, and normalized SCFA levels, showing that ZO extract possesses intestinal-function strengthening effects. Full article

(This article belongs to the Special Issue Research on Natural Products for Intestinal Disorders)

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20 pages, 15030 KiB

Open AccessArticle

Angelica Sinensis Polysaccharide-Based Nanoparticles for Liver-Targeted Delivery of Oridonin

by Henglai Sun, Jijuan Nai, Biqi Deng, Zhen Zheng, Xuemei Chen, Chao Zhang, Huagang Sheng and Liqiao Zhu

Molecules 2024, 29(3), 731; https://doi.org/10.3390/molecules29030731 - 5 Feb 2024

Cited by 2 | Viewed by 1737

Abstract

The present work aimed to study the feasibility of Angelica sinensis polysaccharide (ASP) as an instinctive liver targeting drug delivery carrier for oridonin (ORI) in the treatment of hepatocellular carcinoma (HCC). ASP was reacted with deoxycholic acid (DOCA) via an esterification reaction to [...] Read more.

The present work aimed to study the feasibility of Angelica sinensis polysaccharide (ASP) as an instinctive liver targeting drug delivery carrier for oridonin (ORI) in the treatment of hepatocellular carcinoma (HCC). ASP was reacted with deoxycholic acid (DOCA) via an esterification reaction to form an ASP-DOCA conjugate. ORI-loaded ASP-DOCA nanoparticles (ORI/ASP-DOCA NPs) were prepared by the thin-film water method, and their size was about 195 nm in aqueous solution. ORI/ASP-DOCA NPs had a drug loading capacity of up to 9.2%. The release of ORI in ORI/ASP-DOCA NPs was pH-dependent, resulting in rapid decomposition and accelerated drug release at acidic pH. ORI/ASP-DOCA NPs significantly enhanced the accumulation of ORI in liver tumors through ASGPR-mediated endocytosis. In vitro results showed that ORI/ASP-DOCA NPs increased cell uptake and apoptosis in HepG2 cells, and in vivo results showed that ORI/ASP-DOCA NPs caused effective tumor suppression in H22 tumor-bearing mice compared with free ORI. In short, ORI/ASP-DOCA NPs might be a simple, feasible, safe and effective ORI nano-drug delivery system that could be used for the targeted delivery and treatment of liver tumors. Full article

(This article belongs to the Special Issue Drug Delivery Systems Based on Polysaccharides: Second Edition)

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14 pages, 2345 KiB

Open AccessArticle

Aminoquinoline-Based Tridentate (NNN)-Copper Catalyst for C–N Bond-Forming Reactions from Aniline and Diazo Compounds

by Mohsen Teimouri, Selvam Raju, Edward Acheampong, Allison N. Schmittou, Bruno Donnadieu, David O. Wipf, Brad S. Pierce, Sean L. Stokes and Joseph P. Emerson

Molecules 2024, 29(3), 730; https://doi.org/10.3390/molecules29030730 - 5 Feb 2024

Cited by 1 | Viewed by 1501

Abstract

A new tridentate Cu²⁺ complex based on (E)-1-(pyridin-2-yl)-N-(quinolin-8-yl)methanimine (PQM) was generated and characterized to support the activation of diazo compounds for the formation of new C–N bonds. This neutral Schiff base ligand was structurally characterized to coordinate with [...] Read more.

A new tridentate Cu²⁺ complex based on (E)-1-(pyridin-2-yl)-N-(quinolin-8-yl)methanimine (PQM) was generated and characterized to support the activation of diazo compounds for the formation of new C–N bonds. This neutral Schiff base ligand was structurally characterized to coordinate with copper(II) in an equatorial fashion, yielding a distorted octahedral complex. Upon characterization, this copper(II) complex was used to catalyze an efficient and cost-effective protocol for C–N bond formation between N-nucleophiles and copper carbene complexes arising from the activation of diazo carbonyl compounds. A substrate scope of approximately 15 different amine-based substrates was screened, yielding 2° or 3° amine products with acceptable to good yields under mild reaction conditions. Reactivity towards phenol and thiophenol were also screened, showing relatively weak C–O or C–S bond formation under optimized conditions. Full article

(This article belongs to the Special Issue Featured Papers in Organometallic Chemistry)

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15 pages, 6560 KiB

Open AccessArticle

In Vivo Wound Healing Potential and Molecular Pathways of Amniotic Fluid and Moringa Olifera-Loaded Nanoclay Films

by Akram Ashames, Munaza Ijaz, Manal Buabeid, Haya Yasin, Sidra Yaseen, Richie R. Bhandare and Ghulam Murtaza

Molecules 2024, 29(3), 729; https://doi.org/10.3390/molecules29030729 - 5 Feb 2024

Cited by 2 | Viewed by 1638

Abstract

Cutaneous wounds pose a significant health burden, affecting millions of individuals annually and placing strain on healthcare systems and society. Nanofilm biomaterials have emerged as promising interfaces between materials and biology, offering potential for various biomedical applications. To explore this potential, our study [...] Read more.

Cutaneous wounds pose a significant health burden, affecting millions of individuals annually and placing strain on healthcare systems and society. Nanofilm biomaterials have emerged as promising interfaces between materials and biology, offering potential for various biomedical applications. To explore this potential, our study aimed to assess the wound healing efficacy of amniotic fluid and Moringa olifera-loaded nanoclay films by using in vivo models. Additionally, we investigated the antioxidant and antibacterial properties of these films. Using a burn wound healing model on rabbits, both infected and non-infected wounds were treated with the nanoclay films for a duration of twenty-one days on by following protocols approved by the Animal Ethics Committee. We evaluated wound contraction, proinflammatory mediators, and growth factors levels by analyzing blood samples. Histopathological changes and skin integrity were assessed through H&E staining. Statistical analysis was performed using SPSS software (version 2; Chicago, IL, USA) with significance set at p < 0.05. Our findings demonstrated a significant dose-dependent increase in wound contraction in the 2%, 4%, and 8% AMF-Me.mo treatment groups throughout the study (p < 0.001). Moreover, macroscopic analysis revealed comparable effects (p > 0.05) between the 8% AMF-Me.mo treatment group and the standard treatment. Histopathological examination confirmed the preservation of skin architecture and complete epidermal closure in both infected and non-infected wounds treated with AMF-Me.mo-loaded nanofilms. RT-PCR analysis revealed elevated concentrations of matrix metalloproteinases (MMPs) and vascular endothelial growth factor (VEGF), along with decreased levels of tumor necrosis factor-alpha (TNF-α) in AMF-Me.mo-loaded nanofilm treatment groups. Additionally, the antimicrobial activity of AMF-Me.mo-loaded nanofilms contributed to the decontamination of the wound site, positioning them as potential candidates for effective wound healing. However, further extensive clinical trials-based studies are necessary to confirm these findings. Full article

(This article belongs to the Special Issue Polysaccharide-Based Biopolymer: Recent Development and Applications)

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39 pages, 3914 KiB

Open AccessReview

Natural Compounds in Non-Melanoma Skin Cancer: Prevention and Treatment

by Szymon Kowalski, Julia Karska, Maciej Tota, Katarzyna Skinderowicz, Julita Kulbacka and Małgorzata Drąg-Zalesińska

Molecules 2024, 29(3), 728; https://doi.org/10.3390/molecules29030728 - 4 Feb 2024

Cited by 4 | Viewed by 3574

Abstract

The elevated occurrence of non-melanoma skin cancer (NMSC) and the adverse effects associated with available treatments adversely impact the quality of life in multiple dimensions. In connection with this, there is a necessity for alternative approaches characterized by increased tolerance and lower side [...] Read more.

The elevated occurrence of non-melanoma skin cancer (NMSC) and the adverse effects associated with available treatments adversely impact the quality of life in multiple dimensions. In connection with this, there is a necessity for alternative approaches characterized by increased tolerance and lower side effects. Natural compounds could be employed due to their safety profile and effectiveness for inflammatory and neoplastic skin diseases. These anti-cancer drugs are often derived from natural sources such as marine, zoonotic, and botanical origins. Natural compounds should exhibit anti-carcinogenic actions through various pathways, influencing apoptosis potentiation, cell proliferation inhibition, and metastasis suppression. This review provides an overview of natural compounds used in cancer chemotherapies, chemoprevention, and promotion of skin regeneration, including polyphenolic compounds, flavonoids, vitamins, alkaloids, terpenoids, isothiocyanates, cannabinoids, carotenoids, and ceramides. Full article

(This article belongs to the Section Medicinal Chemistry)

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18 pages, 9567 KiB

Open AccessReview

Recent Developments in Functional Polymers via the Kabachnik–Fields Reaction: The State of the Art

by Rui Yuan, Xianzhe He, Chongyu Zhu and Lei Tao

Molecules 2024, 29(3), 727; https://doi.org/10.3390/molecules29030727 - 4 Feb 2024

Viewed by 1455

Abstract

Recently, multicomponent reactions (MCRs) have attracted much attention in polymer synthesis. As one of the most well-known MCRs, the Kabachnik–Fields (KF) reaction has been widely used in the development of new functional polymers. The KF reaction can efficiently introduce functional groups into polymer [...] Read more.

Recently, multicomponent reactions (MCRs) have attracted much attention in polymer synthesis. As one of the most well-known MCRs, the Kabachnik–Fields (KF) reaction has been widely used in the development of new functional polymers. The KF reaction can efficiently introduce functional groups into polymer structures; thus, polymers prepared via the KF reaction have unique α-aminophosphonates and show important bioactivity, metal chelating abilities, and flame-retardant properties. In this mini-review, we mainly summarize the latest advances in the KF reaction to synthesize functional polymers for the preparation of heavy metal adsorbents, multifunctional hydrogels, flame retardants, and bioimaging probes. We also discuss some emerging applications of functional polymers prepared by means of the KF reaction. Finally, we put forward our perspectives on the further development of the KF reaction in polymer chemistry. Full article

(This article belongs to the Section Organic Chemistry)

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10 pages, 2293 KiB

Open AccessArticle

Improved Process for the Continuous Acylation of 1,3-Benzodioxole

by Davide Pollon, Francesca Annunziata, Stefano Paganelli, Lucia Tamborini, Andrea Pinto, Sabrina Fabris, Maria Antonietta Baldo and Oreste Piccolo

Molecules 2024, 29(3), 726; https://doi.org/10.3390/molecules29030726 - 4 Feb 2024

Viewed by 1450

Abstract

The acylation of 1,3-benzodioxole was studied in a continuous process using a recyclable heterogeneous substoichiometric catalyst. In a short time period (30 min), at 100 °C, the conversion rate was 73%, with a selectivity of 62% of the desired acylated product; the reaction [...] Read more.

The acylation of 1,3-benzodioxole was studied in a continuous process using a recyclable heterogeneous substoichiometric catalyst. In a short time period (30 min), at 100 °C, the conversion rate was 73%, with a selectivity of 62% of the desired acylated product; the reaction was run continuously for 6 h, showing excellent stability and selectivity. Moreover, the unreacted starting material, 1,3-benzodioxole, can be easily separated by distillation and recycled. Full article

(This article belongs to the Special Issue Research on Heterogeneous Catalysis)

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18 pages, 3908 KiB

Open AccessArticle

Discovery of Novel Antitumor Small-Molecule Agent with Dual Action of CDK2/p-RB and MDM2/p53

by Zhaofeng Liu, Yifei Yang, Xiaohui Sun, Runchen Ma, Wenjing Zhang, Wenyan Wang, Gangqiang Yang, Hongbo Wang, Jianzhao Zhang, Yunjie Wang and Jingwei Tian

Molecules 2024, 29(3), 725; https://doi.org/10.3390/molecules29030725 - 4 Feb 2024

Cited by 1 | Viewed by 1826

Abstract

Cell cycle-dependent kinase 2 (CDK2) is located downstream of CDK4/6 in the cell cycle and regulates cell entry into S-phase by binding to Cyclin E and hyper-phosphorylating Rb. Proto-oncogene murine double minute 2 (MDM2) is a key negative regulator of p53, which is [...] Read more.

Cell cycle-dependent kinase 2 (CDK2) is located downstream of CDK4/6 in the cell cycle and regulates cell entry into S-phase by binding to Cyclin E and hyper-phosphorylating Rb. Proto-oncogene murine double minute 2 (MDM2) is a key negative regulator of p53, which is highly expressed in tumors and plays an important role in tumorigenesis and progression. In this study, we identified a dual inhibitor of CDK2 and MDM2, III-13, which had good selectivity for inhibiting CDK2 activity and significantly reduced MDM2 expression. In vitro results showed that III-13 inhibited proliferation of a wide range of tumor cells, regardless of whether Cyclin E1 (CCNE1) was overexpressed or not. The results of in vivo experiments showed that III-13 significantly inhibited proliferation of tumor cells and did not affect body weight of mice. The results of the druggability evaluation showed that III-13 was characterized by low bioavailability and poor membrane permeability when orally administered, suggesting the necessity of further structural modifications. Therefore, this study provided a lead compound for antitumor drugs, especially those against CCNE1-amplified tumor proliferation. Full article

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22 pages, 4389 KiB

Open AccessArticle

Biospeciation of Oxidovanadium(IV) Imidazolyl–Carboxylate Complexes and Their Action on Glucose-Stimulated Insulin Secretion in Pancreatic Cells

by Vital Ugirinema, Frank Odei-Addo, Carminita L. Frost and Zenixole R. Tshentu

Molecules 2024, 29(3), 724; https://doi.org/10.3390/molecules29030724 - 4 Feb 2024

Cited by 1 | Viewed by 1674

Abstract

The reaction of the vanadyl ion (VO²⁺) with imidazole-4-carboxylic acid (Im4COOH), imidazole-2-carboxylic acid (Im2COOH) and methylimidazole-2-carboxylic acid (MeIm2COOH), respectively, in the presence of small bioligands (bL) [oxalate (Ox), lactate (Lact), citrate (Cit) and phosphate (Phos)] and high-molecular-weight (HMW) human serum proteins [...] Read more.

The reaction of the vanadyl ion (VO²⁺) with imidazole-4-carboxylic acid (Im4COOH), imidazole-2-carboxylic acid (Im2COOH) and methylimidazole-2-carboxylic acid (MeIm2COOH), respectively, in the presence of small bioligands (bL) [oxalate (Ox), lactate (Lact), citrate (Cit) and phosphate (Phos)] and high-molecular-weight (HMW) human serum proteins [albumin (HSA) and transferrin (hTf)] were studied in aqueous solution using potentiometric acid–base titrations. The species distribution diagrams for the high-molecular-mass (HMM) proteins with oxidovanadium(IV) under physiological pH were dominated by VO(HMM)₂, VOL(HMM) for unsubstituted ligands (L⁻ = Im4COO⁻ and Im2COO⁻). However, for the N-substituted MeIm2COOH, the species distribution diagrams under physiological pH were dominated by VOL₂, VO(HMM)₂ and VO₂L₂(HMM). These species were further confirmed by LC-MS, MALDI-TOF-MS and EPR studies. The glucose-stimulated insulin secretion (GSIS) action of the complexes was investigated using INS-1E cells at a 1 µM concentration, which was established through cytotoxicity studies via the MTT assay. The neutral complexes, especially VO(MeIm2COO)₂, showed promising results in the stimulation of insulin secretion than the cationic [VO(MeIm2CH₂OH)₂]²⁺ complex and the vanadium salt. Oxidovanadium(IV) complexes reduced insulin stimulation significantly under normoglycaemic levels but showed positive effects on insulin secretion under hyperglycaemic conditions (33.3 mM glucose media). The islets exposed to oxidovanadium(IV) complexes under hyperglycaemic conditions displayed a significant increase in the stimulatory index with 1.19, 1.75, 1.53, 1.85, 2.20 and 1.29 observed for the positive control (sulfonylurea:gliclazide), VOSO₄, VO(Im4COO)₂, VO(Im2COO)₂, VO(MeIm2COO)₂ and VO(MeIm2CH₂OH)₂²⁺, respectively. This observation showed a potential further effect of vanadium complexes towards type 2 diabetes and has been demonstrated for the first time in this study. Full article

(This article belongs to the Special Issue Advances in Vanadium Complexes)

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17 pages, 19240 KiB

Open AccessArticle

Influence of the Tensile Strain on Electron Transport of Ultra-Thin SiC Nanowires

by Qin Tan, Jie Li, Kun Liu, Rukai Liu and Vladimir Skuratov

Molecules 2024, 29(3), 723; https://doi.org/10.3390/molecules29030723 - 4 Feb 2024

Cited by 1 | Viewed by 1130

Abstract

The influence of nanomechanical tensile behavior on electron transport is especially interesting for ultra-thin SiC nanowires (NWs) with different diameters. Our studies theoretically show that these NWs can hold stable electron transmission in some strain ranges and that stretching can enhance the electron [...] Read more.

The influence of nanomechanical tensile behavior on electron transport is especially interesting for ultra-thin SiC nanowires (NWs) with different diameters. Our studies theoretically show that these NWs can hold stable electron transmission in some strain ranges and that stretching can enhance the electron transmission around the Fermi level (E_F) at the strains over 0.5 without fracture for a single-atom SiC chain and at the strains not over 0.5 for thicker SiC NWs. For each size of SiC NW, the tensile strain has a tiny effect on the number of device density of states (DDOSs) peaks but can increase the values. Freshly broken SiC NWs also show certain values of DDOSs around E_F. The maximum DDOS increases significantly with the diameter, but interestingly, the DDOS at E_F shows little difference among the three sizes of devices in the late stage of the stretching. Essentially, high electron transmission is influenced by high DDOSs and delocalized electronic states. Analysis of electron localization functions (ELFs) indicates that appropriate tensile stress can promote continuous electronic distributions to contribute electron transport, while excessively large stretching deformation of SiC NWs would split electronic distributions and consequently hinder the movement of electrons. These results provide strong theoretical support for the use of ultra-thin SiC NWs in nano-sensors for functional and controllable electronic devices. Full article

(This article belongs to the Special Issue Recent Advancements in Density Functional Theory (DFT) and beyond for Computational Chemistry)

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27 pages, 2900 KiB

Open AccessReview

Early Diagnosis of Neurodegenerative Diseases: What Has Been Undertaken to Promote the Transition from PET to Fluorescence Tracers

by Nicolò Bisi, Luca Pinzi, Giulio Rastelli and Nicolò Tonali

Molecules 2024, 29(3), 722; https://doi.org/10.3390/molecules29030722 - 4 Feb 2024

Cited by 3 | Viewed by 2306

Abstract

Alzheimer’s Disease (AD) and Parkinson’s Disease (PD) represent two among the most frequent neurodegenerative diseases worldwide. A common hallmark of these pathologies is the misfolding and consequent aggregation of amyloid proteins into soluble oligomers and insoluble β-sheet-rich fibrils, which ultimately lead to neurotoxicity [...] Read more.

Alzheimer’s Disease (AD) and Parkinson’s Disease (PD) represent two among the most frequent neurodegenerative diseases worldwide. A common hallmark of these pathologies is the misfolding and consequent aggregation of amyloid proteins into soluble oligomers and insoluble β-sheet-rich fibrils, which ultimately lead to neurotoxicity and cell death. After a hundred years of research on the subject, this is the only reliable histopathological feature in our hands. Since AD and PD are diagnosed only once neuronal death and the first symptoms have appeared, the early detection of these diseases is currently impossible. At present, there is no effective drug available, and patients are left with symptomatic and inconclusive therapies. Several reasons could be associated with the lack of effective therapeutic treatments. One of the most important factors is the lack of selective probes capable of detecting, as early as possible, the most toxic amyloid species involved in the onset of these pathologies. In this regard, chemical probes able to detect and distinguish among different amyloid aggregates are urgently needed. In this article, we will review and put into perspective results from ex vivo and in vivo studies performed on compounds specifically interacting with such early species. Following a general overview on the three different amyloid proteins leading to insoluble β-sheet-rich amyloid deposits (amyloid β_1–42 peptide, Tau, and α-synuclein), a list of the advantages and disadvantages of the approaches employed to date is discussed, with particular attention paid to the translation of fluorescence imaging into clinical applications. Furthermore, we also discuss how the progress achieved in detecting the amyloids of one neurodegenerative disease could be leveraged for research into another amyloidosis. As evidenced by a critical analysis of the state of the art, substantial work still needs to be conducted. Indeed, the early diagnosis of neurodegenerative diseases is a priority, and we believe that this review could be a useful tool for better investigating this field. Full article

(This article belongs to the Section Medicinal Chemistry)

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19 pages, 792 KiB

Open AccessReview

The Role of the PTEN Tumor Suppressor Gene and Its Anti-Angiogenic Activity in Melanoma and Other Cancers

by Jacqueline Maphutha, Danielle Twilley and Namrita Lall

Molecules 2024, 29(3), 721; https://doi.org/10.3390/molecules29030721 - 4 Feb 2024

Cited by 4 | Viewed by 2174

Abstract

Human malignant melanoma and other solid cancers are largely driven by the inactivation of tumor suppressor genes and angiogenesis. Conventional treatments for cancer (surgery, radiation therapy, and chemotherapy) are employed as first-line treatments for solid cancers but are often ineffective as monotherapies due [...] Read more.

Human malignant melanoma and other solid cancers are largely driven by the inactivation of tumor suppressor genes and angiogenesis. Conventional treatments for cancer (surgery, radiation therapy, and chemotherapy) are employed as first-line treatments for solid cancers but are often ineffective as monotherapies due to resistance and toxicity. Thus, targeted therapies, such as bevacizumab, which targets vascular endothelial growth factor, have been approved by the US Food and Drug Administration (FDA) as angiogenesis inhibitors. The downregulation of the tumor suppressor, phosphatase tensin homolog (PTEN), occurs in 30–40% of human malignant melanomas, thereby elucidating the importance of the upregulation of PTEN activity. Phosphatase tensin homolog (PTEN) is modulated at the transcriptional, translational, and post-translational levels and regulates key signaling pathways such as the phosphoinositide 3-kinase (PI3K)/protein kinase B (Akt) and mitogen-activated protein kinase (MAPK) pathways, which also drive angiogenesis. This review discusses the inhibition of angiogenesis through the upregulation of PTEN and the inhibition of hypoxia-inducible factor 1 alpha (HIF-1-α) in human malignant melanoma, as no targeted therapies have been approved by the FDA for the inhibition of angiogenesis in human malignant melanoma. The emergence of nanocarrier formulations to enhance the pharmacokinetic profile of phytochemicals that upregulate PTEN activity and improve the upregulation of PTEN has also been discussed. Full article

(This article belongs to the Special Issue Molecular Targets and Mechanisms of Action of Anti-cancer Agents)

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11 pages, 1915 KiB

Open AccessArticle

Metabolites from Streptomyces aureus (VTCC43181) and Their Inhibition of Mycobacterium tuberculosis ClpC1 Protein

by Thao Thi Phuong Tran, Ni Ngoc Thi Huynh, Ninh Thi Pham, Dung Thi Nguyen, Chien Van Tran, Uyen Quynh Nguyen, Anh Ngoc Ho, Joo-Won Suh, Jinhua Cheng, Thao Kim Nu Nguyen, Sung Van Tran and Duc Minh Nguyen

Molecules 2024, 29(3), 720; https://doi.org/10.3390/molecules29030720 - 4 Feb 2024

Viewed by 1413

Abstract

Tuberculosis is one of the most common infectious diseases in the world, caused by Mycobacterium tuberculosis. The outbreak of multiple drug-resistant tuberculosis has become a major challenge to prevent this disease worldwide. ClpC1 is a Clp ATPase protein of Mycobacterium tuberculosis, [...] Read more.

Tuberculosis is one of the most common infectious diseases in the world, caused by Mycobacterium tuberculosis. The outbreak of multiple drug-resistant tuberculosis has become a major challenge to prevent this disease worldwide. ClpC1 is a Clp ATPase protein of Mycobacterium tuberculosis, functioning as a chaperon when combined with the Clp complex. ClpC1 has emerged as a new target to discover anti-tuberculosis drugs. This study aimed to explore the ClpC1 inhibitors from actinomycetes, which have been known to provide abundant sources of antibiotics. Two cyclic peptides, including nocardamin (1), halolitoralin A (3), and a lactone pleurone (2), were isolated from the culture of Streptomyces aureus (VTCC43181). The structures of these compounds were determined based on the detailed analysis of their spectral data and comparison with references. This is the first time these compounds have been isolated from S. aureus. Compounds 1–3 were evaluated for their affection of ATPase activity of the recombinant ClpC1 protein. Of these compounds, halolitoralin A (1), a macrocyclic peptide, was effective for the ATPase hydrolysis of the ClpC1 protein. Full article

(This article belongs to the Section Bioorganic Chemistry)

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12 pages, 5995 KiB

Open AccessCommunication

Keto-Adamantane-Based Macrocycle Crystalline Supramolecular Assemblies Showing Selective Vapochromism to Tetrahydrofuran

by Zunhua Li, Yingzi Tan, Manhua Ding, Linli Tang and Fei Zeng

Molecules 2024, 29(3), 719; https://doi.org/10.3390/molecules29030719 - 4 Feb 2024

Cited by 3 | Viewed by 1179

Abstract

Here, we report the synthesis of adamantane-based macrocycle 2 by combining adamantane building blocks with π-donor 1,3-dimethoxy-benzene units. An unpredictable keto-adamantane-based macrocycle 3 was obtained by the oxidation of 2 using DDQ as an oxidant. Moreover, a new type of macrocyclic molecule-based CT [...] Read more.

Here, we report the synthesis of adamantane-based macrocycle 2 by combining adamantane building blocks with π-donor 1,3-dimethoxy-benzene units. An unpredictable keto-adamantane-based macrocycle 3 was obtained by the oxidation of 2 using DDQ as an oxidant. Moreover, a new type of macrocyclic molecule-based CT cocrystal was prepared through exo-wall CT interactions between 3 and DDQ. The cocrystal material showed selective vapochromism behavior towards THF, specifically, among nine volatile organic solvents commonly used in the laboratory. Powder X-ray diffraction; UV-Vis diffuse reflectance spectroscopy; ¹H NMR; and single crystal X-ray diffraction analyses revealed that color changes are attributed to the vapor-triggered decomplexation of cocrystals. Full article

(This article belongs to the Special Issue Macrocyclic Compounds: Derivatives and Applications)

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31 pages, 3425 KiB

Open AccessReview

Traditional Uses, Chemical Constituents and Pharmacological Activities of the Toona sinensis Plant

by Mengyao Zhao, Huiting Li, Rongshen Wang, Shuying Lan, Yuxin Wang, Yuhua Zhang, Haishan Sui and Wanzhong Li

Molecules 2024, 29(3), 718; https://doi.org/10.3390/molecules29030718 - 4 Feb 2024

Cited by 1 | Viewed by 1961

Abstract

Toona sinensis (A. Juss.) Roem., which is widely distributed in China, is a homologous plant resource of medicine and food. The leaves, seeds, barks, buds and pericarps of T. sinensis can be used as medicine with traditional efficacy. Due to its extensive use [...] Read more.

Toona sinensis (A. Juss.) Roem., which is widely distributed in China, is a homologous plant resource of medicine and food. The leaves, seeds, barks, buds and pericarps of T. sinensis can be used as medicine with traditional efficacy. Due to its extensive use in traditional medicine in the ancient world, the T. sinensis plant has significant development potential. In this review, 206 compounds, including triterpenoids (1–133), sesquiterpenoids (134–135), diterpenoids (136–142), sterols (143–147), phenols (148–167), flavonoids (168–186), phenylpropanoids (187–192) and others (193–206), are isolated from the T. sinensis plant. The mass spectrum cracking laws of representative compounds (64, 128, 129, 154–156, 175, 177, 179 and 183) are reviewed, which are conducive to the discovery of novel active substances. Modern pharmacological studies have shown that T. sinensis extracts and their compounds have antidiabetic, antidiabetic nephropathy, antioxidant, anti-inflammatory, antitumor, hepatoprotective, antiviral, antibacterial, immunopotentiation and other biological activities. The traditional uses, chemical constituents, compound cracking laws and pharmacological activities of different parts of T. sinensis are reviewed, laying the foundation for improving the development and utilization of its medicinal value. Full article

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13 pages, 3231 KiB

Open AccessArticle

TLC-Bioautography-Guided Isolation and Assessment of Antibacterial Compounds from Manuka (Leptospermum scoparium) Leaf and Branch Extracts

by Wenliang Xu, Danxia Shi, Kuanmin Chen and David G. Popovich

Molecules 2024, 29(3), 717; https://doi.org/10.3390/molecules29030717 - 4 Feb 2024

Cited by 1 | Viewed by 1599

Abstract

A rapid procedure for the targeted isolation of antibacterial compounds from Manuka (Leptospermum scoparium) leaf and branch extracts was described in this paper. Antibacterial compounds from three different Manuka samples collected from New Zealand and China were compared. The active compounds [...] Read more.

A rapid procedure for the targeted isolation of antibacterial compounds from Manuka (Leptospermum scoparium) leaf and branch extracts was described in this paper. Antibacterial compounds from three different Manuka samples collected from New Zealand and China were compared. The active compounds were targeted by TLC-bioautography against S. aureus and were identified by HR-ESI-MS, and -MS/MS analysis in conjunction with Compound Discoverer 3.3. The major antibacterial component, grandiflorone, was identified, along with 20 β-triketones, flavonoids, and phloroglucinol derivatives. To verify the software identification, grandiflorone underwent purification via column chromatography, and its structure was elucidated through NMR analysis, ultimately confirming its identity as grandiflorone. This study successfully demonstrated that the leaves and branches remaining after Manuka essential oil distillation serve as excellent source for extracting grandiflorone. Additionally, we proposed an improved TLC-bioautography protocol for evaluating the antibacterial efficacy on solid surfaces, which is suitable for both S. aureus and E. coli. The minimum effective dose (MED) of grandiflorone was observed to be 0.29–0.59 μg/cm² against S. aureus and 2.34–4.68 μg/cm² against E. coli, respectively. Furthermore, the synthetic plant growth retardant, paclobutrazol, was isolated from the samples obtained in China. It is hypothesized that this compound may disrupt the synthesis pathway of triketones, consequently diminishing the antibacterial efficacy of Chinese Manuka extract in comparison to that of New Zealand. Full article

(This article belongs to the Special Issue Selected Scholars' Exclusive Papers on Natural Products Chemistry)

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15 pages, 8436 KiB

Open AccessArticle

Study on the Physical and Rheological Characterisation of Low-Density Polyethylene (LDPE)/Recycled Crumb Rubber (RCR) on Asphalt Binders

by Shibo Zhang, Yong Yan, Yang Yang and Rongxin Guo

Molecules 2024, 29(3), 716; https://doi.org/10.3390/molecules29030716 - 4 Feb 2024

Viewed by 1374

Abstract

Recycled crumb rubber (RCR) is considered a reliable asphalt modifier and a solution to the problem of scrap tyre recycling. RCR-modified asphalt (RCRMA) typically has good low-temperature performance and storage stability. However, the pre-treatment of crumb rubber (CR) impairs its physical properties, resulting [...] Read more.

Recycled crumb rubber (RCR) is considered a reliable asphalt modifier and a solution to the problem of scrap tyre recycling. RCR-modified asphalt (RCRMA) typically has good low-temperature performance and storage stability. However, the pre-treatment of crumb rubber (CR) impairs its physical properties, resulting in poor high-temperature performance, which limits the industrial application of RCRMA. In this study, low-density polyethylene (LDPE) composite RCR was used to modify asphalt, and LDPE/RCR-composite-modified asphalt (L-RCRMA) was produced to compensate for the deficiencies in the high-temperature performance of RCRMA. The comprehensive physical properties of L-RCRMA were elucidated using tests such as the conventional properties, rotational viscosity, and rheological tests. The results showed that the incorporation of LDPE improved the high-temperature stability and rutting resistance of the asphalt, but an excessive amount of LDPE impaired the low-temperature performance and storage stability of L-RCRMA. Therefore, it is necessary to control the amount of LDPE to balance the performance of the asphalt. On this basis, we recommend a dosage of 20% for RCR and 1.5% for LDPE. Full article

(This article belongs to the Section Materials Chemistry)

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