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Molecules, Volume 28, Issue 2 (January-2 2023) – 451 articles

Cover Story (view full-size image): In low-polarity solvents, the unidirectionality of the threading reaction of a series of bis-viologen axles of different lengths inside the aromatic cavity of two heteroditopic non-symmetric tris(N-phenylureido)calix[6]arene wheels allows the formation of highly preorganized interlocked [3]rotaxane structures. Furthermore, thanks to this straightforward supramolecular templating effect, the macrocycles are confined around the bis-viologen thread in an upper-to-upper geometrical arrangement in which the two calix[6]arene cavities face each other. As a result, the functionalities on the phenylureas para position (ester, carboxylic, or hydroxymethyl groups) possess the correct spatial arrangement that might lead to the realization of molecular capsules based on calix[6]arenes upon adequate bridging reactions. View this paper
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14 pages, 593 KiB  
Article
Toward Accurate yet Effective Computations of Rotational Spectroscopy Parameters for Biomolecule Building Blocks
by Vincenzo Barone, Silvia Di Grande and Cristina Puzzarini
Molecules 2023, 28(2), 913; https://doi.org/10.3390/molecules28020913 - 16 Jan 2023
Cited by 12 | Viewed by 2144
Abstract
The interplay of high-resolution rotational spectroscopy and quantum-chemical computations plays an invaluable role in the investigation of biomolecule building blocks in the gas phase. However, quantum-chemical methods suffer from unfavorable scaling with the dimension of the system under consideration. While a complete characterization [...] Read more.
The interplay of high-resolution rotational spectroscopy and quantum-chemical computations plays an invaluable role in the investigation of biomolecule building blocks in the gas phase. However, quantum-chemical methods suffer from unfavorable scaling with the dimension of the system under consideration. While a complete characterization of flexible systems requires an elaborate multi-step strategy, in this work, we demonstrate that the accuracy obtained by quantum-chemical composite approaches in the prediction of rotational spectroscopy parameters can be approached by a model based on density functional theory. Glycine and serine are employed to demonstrate that, despite its limited cost, such a model is able to predict rotational constants with an accuracy of 0.3% or better, thus paving the way toward the accurate characterization of larger flexible building blocks of biomolecules. Full article
(This article belongs to the Special Issue Structural Characterization of Biomolecules by Spectroscopic Methods)
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18 pages, 4604 KiB  
Article
Application of Natural Deep Eutectic Solvents for Extraction of Bioactive Components from Rhodiola rosea (L.)
by Nikita Tsvetov, Oksana Paukshta, Nadezhda Fokina, Natalia Volodina and Artemiy Samarov
Molecules 2023, 28(2), 912; https://doi.org/10.3390/molecules28020912 - 16 Jan 2023
Cited by 6 | Viewed by 2034
Abstract
Rhodiola rosea (L.) is a valuable source of nutrients. Nutrients have adaptogenic, immunostimulating, nootropic, anti-inflammatory and anti-cancer properties. Natural deep eutectic solvents (NADES) consisting of choline chloride and malonic, malic, tartaric or citric acids have been first used to extract biologically active substances [...] Read more.
Rhodiola rosea (L.) is a valuable source of nutrients. Nutrients have adaptogenic, immunostimulating, nootropic, anti-inflammatory and anti-cancer properties. Natural deep eutectic solvents (NADES) consisting of choline chloride and malonic, malic, tartaric or citric acids have been first used to extract biologically active substances from R. rosea. The total content of polyphenols has been determined by the Folin–Ciocalteu method for all extracts. Antioxidant activity has been determined by the phosphomolybdate method, and antiradical activity has been determined by the 2,2-diphenyl-1-picrylhydrazyl (DPPH) method. Rosavin concentration has been determined by high-performance liquid chromatography (HPLC). Extraction kinetics has been evaluated regarding the effectiveness of NADES with each other and with reference solvents (water and 50% ethanol) has been made. Extraction conditions have been optimized according to the Box–Behnken design of the experiment. The optimal parameters of the extraction process have been established. The antibacterial activity of NADES-based extracts against bacterial cultures of Micrococcus luteus, Pseudomonas fluorescens, and Bacillus subtilis has been studied. Full article
(This article belongs to the Special Issue New Approaches in the Extraction of Biomolecules from Plants–Molecular and Application Basics)
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11 pages, 2052 KiB  
Article
Controlled Assembly of Fluorophores inside a Nanoliposome
by Hiroaki Konishi, Eiji Nakata, Futa Komatsubara and Takashi Morii
Molecules 2023, 28(2), 911; https://doi.org/10.3390/molecules28020911 - 16 Jan 2023
Cited by 1 | Viewed by 1511
Abstract
Cellular compartmentalization plays an essential role in organizing the complex and multiple biochemical reactions in the cell. An artificial compartment would provide powerful strategies to develop new biochemical tools for material production and diagnosis, but it is still a great challenge to synthesize [...] Read more.
Cellular compartmentalization plays an essential role in organizing the complex and multiple biochemical reactions in the cell. An artificial compartment would provide powerful strategies to develop new biochemical tools for material production and diagnosis, but it is still a great challenge to synthesize the compartments that encapsulate materials of interest while controlling their accurate locations, numbers, and stoichiometry. In this study, we evaluated chemical characteristics of a liposome-encapsulated compartment, which has great potential to locate various materials of interest with precise control of their locations and numbers in the compartment. A nanoliposome was constructed inside a ring-shaped DNA origami skeleton according to the method of Yang et al., and further equipped with a double-stranded DNA platform to assemble molecules of interest in the nanoliposome. Upon formation of the nanoliposome, a pH-sensitive fluorophore on the bridged platform showed little or no response to the pH change of the outer buffer, ensuring that the molecules assembled on the platform are effectively shielded from the outer environment. The ring-shaped DNA skeleton equipped with a double-stranded DNA platform allows spatial assembly of several functional molecules inside the nanoliposome to isolate them from the outer environment. Full article
(This article belongs to the Special Issue Recent Advancements in Organic Fluorophores Preparation and Applications in Chemical Biology and Functional Materials)
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12 pages, 1337 KiB  
Article
Improvement of the Chemical Reactivity of Michael Acceptor of Ethacrynic Acid Correlates with Antiproliferative Activities
by Abdelmoula El Abbouchi, Nabil El Brahmi, Marie-Aude Hiebel, Hamza Ghammaz, Elmostafa El Fahime, Jérôme Bignon, Gérald Guillaumet, Franck Suzenet and Saïd El Kazzouli
Molecules 2023, 28(2), 910; https://doi.org/10.3390/molecules28020910 - 16 Jan 2023
Cited by 3 | Viewed by 1818
Abstract
The present study aims to report the design, synthesis, and biological activity of new ethacrynic acid (EA) analogs (6–10) obtained by the double modulation of the carboxylic acid moiety and the aromatic ring with the aim to increase the [...] Read more.
The present study aims to report the design, synthesis, and biological activity of new ethacrynic acid (EA) analogs (6–10) obtained by the double modulation of the carboxylic acid moiety and the aromatic ring with the aim to increase the chemical reactivity of Michael acceptor of EA. All obtained compounds were characterized by 1H and 13C NMR, IR, and high-resolution mass spectrometry. The antiproliferative activity was evaluated in vitro using MMT test, in a first step, against HL60 cell line and in a second step, on a panel of human cancer cell lines such as HCT116, A549, MCF7, PC3, U87-MG, and SKOV3, and normal cell line MRC5 in comparison with positive control doxorubicin. Among all the tested compounds, the product 8 containing a propargyl and a hydroxyl groups, allowing an intramolecular hydrogen bond with the keto group of EA, exhibited a pronounced and selective activity in a nanomolar range against HL60, A549, PC3, and MCF7 with IC50 values of 15, 41.2, 68.7, and 61.5 nM, respectively. Compound 8 also showed a good selectivity index (SI) against HL60 and moderate SI against the other three human cancer cells (A549, PC3, and MCF7). The study of the structure-activity relationship showed that both modifications of the carboxylic group and the introduction of an intramolecular hydrogen bond are highly required to improve the antiproliferative activities. The molecular modeling studies of compound 8 revealed that it favorably binds to the glutathione S-transferase active site, which may explain its interesting anticancer activity. These new compounds have potential to be developed as novel therapeutic agents against various cancer types. Full article
(This article belongs to the Special Issue Molecular Targets and Mechanisms of Action of Anti-cancer Agents)
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19 pages, 7691 KiB  
Article
In Silico Identification of 1-DTP Inhibitors of Corynebacterium diphtheriae Using Phytochemicals from Andrographis paniculata
by Jameel M. Al-Khayri, Sakshi Dubey, Gopishankar Thirumoorthy, Praveen Nagella, Adel Abdel-Sabour Rezk and Wael Fathi Shehata
Molecules 2023, 28(2), 909; https://doi.org/10.3390/molecules28020909 - 16 Jan 2023
Cited by 1 | Viewed by 1383
Abstract
A number of phytochemicals have been identified as promising drug molecules against a variety of diseases using an in-silico approach. The current research uses this approach to identify the phyto-derived drugs from Andrographis paniculata (Burm. f.) Wall. ex Nees (AP) for the treatment [...] Read more.
A number of phytochemicals have been identified as promising drug molecules against a variety of diseases using an in-silico approach. The current research uses this approach to identify the phyto-derived drugs from Andrographis paniculata (Burm. f.) Wall. ex Nees (AP) for the treatment of diphtheria. In the present study, 18 bioactive molecules from Andrographis paniculata (obtained from the PubChem database) were docked against the diphtheria toxin using the AutoDock vina tool. Visualization of the top four molecules with the best dockscore, namely bisandrographolide (−10.4), andrographiside (−9.5), isoandrographolide (−9.4), and neoandrographolide (−9.1), helps gain a better understanding of the molecular interactions. Further screening using molecular dynamics simulation studies led to the identification of bisandrographolide and andrographiside as hit compounds. Investigation of pharmacokinetic properties, mainly ADMET, along with Lipinski’s rule and binding affinity considerations, narrowed down the search for a potent drug to bisandrographolide, which was the only molecule to be negative for AMES toxicity. Thus, further modification of this compound followed by in vitro and in vivo studies can be used to examine itseffectiveness against diphtheria. Full article
(This article belongs to the Special Issue Antibacterial Agents from Natural Source)
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14 pages, 1085 KiB  
Review
Review on Extraction, Modification, and Synthesis of Natural Peptides and Their Beneficial Effects on Skin
by Jiabing An, Ivan Stève Nguepi Tsopmejio, Zi Wang and Wei Li
Molecules 2023, 28(2), 908; https://doi.org/10.3390/molecules28020908 - 16 Jan 2023
Cited by 2 | Viewed by 2124
Abstract
Peptides, functional nutrients with a size between those of large proteins and small amino acids, are easily absorbed by the human body. Therefore, they are seeing increasing use in clinical medicine and have revealed immunomodulatory and anti-inflammatory properties which could make them effective [...] Read more.
Peptides, functional nutrients with a size between those of large proteins and small amino acids, are easily absorbed by the human body. Therefore, they are seeing increasing use in clinical medicine and have revealed immunomodulatory and anti-inflammatory properties which could make them effective in healing skin wounds. This review sorted and summarized the relevant literature about peptides during the past decade. Recent works on the extraction, modification and synthesis of peptides were reviewed. Importantly, the unique beneficial effects of peptides on the skin were extensively explored, providing ideas for the development and innovation of peptides and laying a knowledge foundation for the clinical application of peptides. Full article
(This article belongs to the Special Issue Natural Products: Chemical Composition and Pharmacological Activity)
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14 pages, 3973 KiB  
Article
Green Synthesis of Flower-Like Carrageenan-Silver Nanoparticles and Elucidation of Its Physicochemical and Antibacterial Properties
by Syafiqah Syazwani Jaffar, Suryani Saallah, Mailin Misson, Shafiquzzaman Siddiquee, Jumardi Roslan and Wuled Lenggoro
Molecules 2023, 28(2), 907; https://doi.org/10.3390/molecules28020907 - 16 Jan 2023
Cited by 8 | Viewed by 2360
Abstract
Herein, we report the green synthesis of flower-like carrageenan-silver nanoparticles (c-AgNPs) through a facile hydrothermal reaction at 90 °C for 2 h. The reduction of silver nitrate (AgNO3) to c-AgNPs was evident by the colour change of the solution from colourless [...] Read more.
Herein, we report the green synthesis of flower-like carrageenan-silver nanoparticles (c-AgNPs) through a facile hydrothermal reaction at 90 °C for 2 h. The reduction of silver nitrate (AgNO3) to c-AgNPs was evident by the colour change of the solution from colourless to dark brown and further confirmed by a UV-Vis surface plasmon resonance (SPR) peak at ~420 nm. The FTIR spectra showed that the abundance of functional groups present in the carrageenan were responsible for the reduction and stabilisation of the c-AgNPs. The XRD pattern confirmed the crystalline nature and face-centred cubic structure of the c-AgNPs, while the EDX analysis showed the presence of a high composition of elemental silver (85.87 wt%). Interestingly, the morphological characterisations by SEM and FE-SEM revealed the formation of flower-like c-AgNPs composed of intercrossed and random lamellar petals of approximately 50 nm in thickness. The growth mechanism of flower-like c-AgNPs were elucidated based on the TEM and AFM analyses. The c-AgNPs displayed promising antibacterial properties against E. coli and S. aureus, with zones of inhibition ranging from 8.0 ± 0.0 to 11.7 ± 0.6 mm and 7.3 ± 0.6 to 9.7 ± 0.6 mm, respectively, as the concentration of c-AgNPs increased from 0.1 to 4 mg/mL. Full article
(This article belongs to the Special Issue Metal-Based Complex: Preparation and Medicinal Characteristics)
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17 pages, 4322 KiB  
Article
Hydroponic Ginseng ROOT Mediated with CMC Polymer-Coated Zinc Oxide Nanoparticles for Cellular Apoptosis via Downregulation of BCL-2 Gene Expression in A549 Lung Cancer Cell Line
by Yinping Jin, Esrat Jahan Rupa, Jinnatun Nahar, Li Ling, Aditi Mitra Puja, Reshmi Akter, Deok Chun Yang, Se Chan Kang and Hao Zhang
Molecules 2023, 28(2), 906; https://doi.org/10.3390/molecules28020906 - 16 Jan 2023
Cited by 2 | Viewed by 2122
Abstract
The unique and tailorable physicochemical features of zinc oxide nanoparticles (ZnO-NPs) synthesized from green sources make them attractive for use in cancer treatment. Hydroponic-cultured ginseng-root-synthesized ZnO-NPs (HGRCm-ZnO NPs) were coated with O-carboxymethyl chitosan (CMC) polymer, which stabilized and enhanced the biological efficacy of [...] Read more.
The unique and tailorable physicochemical features of zinc oxide nanoparticles (ZnO-NPs) synthesized from green sources make them attractive for use in cancer treatment. Hydroponic-cultured ginseng-root-synthesized ZnO-NPs (HGRCm-ZnO NPs) were coated with O-carboxymethyl chitosan (CMC) polymer, which stabilized and enhanced the biological efficacy of the nanoparticles. Nanoparticles were characterized by X-ray diffraction (XRD), UV-Vis spectroscopy, transmission electron microscopy (TEM), Fourier-transform infrared spectroscopy (FT-IR), and energy-dispersive X-ray spectroscopy (EDS). The flower-shaped nanoparticles were crystalline in nature with a particle size of 28 nm. To evaluate if these NPs had anti-lung cancer activity, analysis was performed on a human lung carcinoma cell line (A549). HGRCm-ZnO nanoparticles showed less toxicity to normal keratinocytes (HaCaTs), at concentrations up to 20 µg/mL, than A549 cancer cells. Additionally, these NPs showed dose-dependent colony formation and cell migration inhibition ability, which makes them more promising for lung cancer treatment. Additionally, Hoechst and propidium iodide dye staining also confirmed that the NP formulation had apoptotic activity in cancer cells. Further, to evaluate the mechanism of cancer cell death via checking the gene expression, HGRCm ZnO NPs upregulated the BAX and Caspase 3 and 9 expression levels but downregulated Bcl-2 expression, indicating that the nanoformulation induced mitochondrial-mediated apoptosis. Moreover, these preliminary results suggest that HGRCm ZnO NPs can be a potential candidate for future lung cancer treatment. Full article
(This article belongs to the Special Issue Green Synthetic Nanomaterials: Preparation, Mechanism, and Application)
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15 pages, 7401 KiB  
Review
Fluoropolymer: A Review on Its Emulsion Preparation and Wettability to Solid-Liquid Interface
by Lei Liang, Tao Wen, Jun Xin, Chao Su, Ke Song, Wei Zhao, Hongwu Liu and Gui Su
Molecules 2023, 28(2), 905; https://doi.org/10.3390/molecules28020905 - 16 Jan 2023
Cited by 5 | Viewed by 2257
Abstract
In the preparation of a superamphiphobic surface, the most basic method is to reduce the surface free energy of the interface. The C—F bond has a very low surface free energy, which can significantly change the wettability of the solid–liquid interface and make [...] Read more.
In the preparation of a superamphiphobic surface, the most basic method is to reduce the surface free energy of the interface. The C—F bond has a very low surface free energy, which can significantly change the wettability of the solid–liquid interface and make it a hydrophobic or oleophobic, or even superamphiphobic surface. Based on the analysis of a large number of research articles, the preparation and application progress in fluoropolymer emulsion were summarized. After that, some corresponding thoughts were put forward combined with our professional characteristics. According to recent research, the status of the fluoropolymer emulsion preparation system was analyzed. In addition, all related aspects of fluoropolymer emulsion were systematically classified in varying degrees. Furthermore, the interaction between fluoropolymer structure and properties, especially the interaction with nanomaterials, was also explored. The aim of this review is to try to attract more scholars’ attention to fluorocarbon interfacial materials. It is expected that it will make a certain theoretical and practical significance in the preparation and application of fluoropolymer. Full article
(This article belongs to the Section Macromolecular Chemistry)
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8 pages, 1112 KiB  
Article
Probing the Potential Energy Profile of the I + (H2O)3 → HI + (H2O)2OH Forward and Reverse Reactions: High Level CCSD(T) Studies with Spin-Orbit Coupling Included
by Xinyuan Zhang, Xiaoting Chen, Yan Lin, Yan Meng, Guoliang Li, Yaoming Xie and Henry F. Schaefer III
Molecules 2023, 28(2), 904; https://doi.org/10.3390/molecules28020904 - 16 Jan 2023
Viewed by 1171
Abstract
Three different pathways for the atomic iodine plus water trimer reaction I + (H2O)3 → HI + (H2O)2OH were preliminarily examined by the DFT-MPW1K method. Related to previous predictions for the F/Cl/Br + (H2O) [...] Read more.
Three different pathways for the atomic iodine plus water trimer reaction I + (H2O)3 → HI + (H2O)2OH were preliminarily examined by the DFT-MPW1K method. Related to previous predictions for the F/Cl/Br + (H2O)3 reactions, three pathways for the I + (H2O)3 reaction are linked in terms of geometry and energetics. To legitimize the results, the “gold standard” CCSD(T) method was employed to investigate the lowest-lying pathway with the correlation-consistent polarized valence basis set up to cc-pVQZ(-PP). According to the CCSD(T)/cc-pVQZ(-PP)//CCSD(T)/cc-pVTZ(-PP) results, the I + (H2O)3 → HI + (H2O)2OH reaction is predicted to be endothermic by 47.0 kcal mol−1. The submerged transition state is predicted to lie 43.7 kcal mol−1 above the separated reactants. The I···(H2O)3 entrance complex lies below the separated reactants by 4.1 kcal mol−1, and spin-orbit coupling has a significant impact on this dissociation energy. The HI···(H2O)2OH exit complex is bound by 4.3 kcal mol−1 in relation to the separated products. Compared with simpler I + (H2O)2 and I + H2O reactions, the I + (H2O)3 reaction is energetically between them in general. It is speculated that the reaction between the iodine atom and the larger water clusters may be energetically analogous to the I + (H2O)3 reaction. The iodine reaction I + (H2O)3 is connected with the analogous valence isoelectronic bromine/chlorine reactions Br/Cl + (H2O)3 but much different from the F + (H2O)3 reaction. Significant difference with other halogen systems, especially for barrier heights, are seen for the iodine systems. Full article
(This article belongs to the Topic Theoretical, Quantum and Computational Chemistry)
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25 pages, 7138 KiB  
Article
Biochemical Pilot Study on Effects of Pomegranate Seed Oil Extract and Cosmetic Cream on Neurologically Mediated Skin Inflammation in Animals and Humans: A Comparative Observational Study
by Asmaa Fathi Hamouda and Shifa Felemban
Molecules 2023, 28(2), 903; https://doi.org/10.3390/molecules28020903 - 16 Jan 2023
Cited by 6 | Viewed by 3024
Abstract
The presence of phenobarbital and formaldehyde in drugs, food, and beverages can lead to various health issues, including inflammation, oncogenesis, and neurological distress. Psychological stress leads to mood fluctuations and the onset of skin inflammation. Skin inflammation has a range of causes, including [...] Read more.
The presence of phenobarbital and formaldehyde in drugs, food, and beverages can lead to various health issues, including inflammation, oncogenesis, and neurological distress. Psychological stress leads to mood fluctuations and the onset of skin inflammation. Skin inflammation has a range of causes, including chemicals, heavy metals, infection, immune-related disorders, genetics, and stress. The various treatments for skin inflammation include medical and cosmetic creams, diet changes, and herbal therapy. In this study, we investigated the effects of Avocom-M and pomegranate seed oil extract (PSOE) against phenobarbital- and formaldehyde-induced skin biochemical changes in rats. We analyzed the constituents of PSOE using gas chromatography–mass spectrometry and inductively coupled plasma–mass spectrometry. We also observed biochemical changes in the skin of human volunteers with and without TROSYD and PSOE as a skin cream. We compared the biochemical changes in human volunteers’ skin before treatment and 21 days after the treatment stopped. The outcomes showed an improvement in the rats’ biochemical status, due to PSOE and Avocom-M treatment. The human volunteers treated with TROSYD and PSOE showed substantial amelioration of skin inflammation. PSOE, Avocom-M, and TROSYD produced beneficial effects by reducing the levels of cyclooxygenase-2, lipid peroxidation, tyrosinase, hyaluronidase, elastase, collagenase, and nitric oxide in the animals tested on and in human volunteers. Full article
(This article belongs to the Special Issue Recent Progress in Small Molecule Inhibitors as Targeted Cancer Therapy)
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21 pages, 8464 KiB  
Article
Synthesis and Antiparasitic Activity of New Trithiolato-Bridged Dinuclear Ruthenium(II)-arene-carbohydrate Conjugates
by Isabelle Holzer, Oksana Desiatkina, Nicoleta Anghel, Serena K. Johns, Ghalia Boubaker, Andrew Hemphill, Julien Furrer and Emilia Păunescu
Molecules 2023, 28(2), 902; https://doi.org/10.3390/molecules28020902 - 16 Jan 2023
Cited by 3 | Viewed by 1767
Abstract
Eight novel carbohydrate-tethered trithiolato dinuclear ruthenium(II)-arene complexes were synthesized using CuAAC ‘click’ (Cu(I)-catalyzed azide-alkyne cycloaddition) reactions, and there in vitro activity against transgenic T. gondii tachyzoites constitutively expressing β-galactosidase (T. gondii β-gal) and in non-infected human foreskin fibroblasts, HFF, was determined at [...] Read more.
Eight novel carbohydrate-tethered trithiolato dinuclear ruthenium(II)-arene complexes were synthesized using CuAAC ‘click’ (Cu(I)-catalyzed azide-alkyne cycloaddition) reactions, and there in vitro activity against transgenic T. gondii tachyzoites constitutively expressing β-galactosidase (T. gondii β-gal) and in non-infected human foreskin fibroblasts, HFF, was determined at 0.1 and 1 µM. When evaluated at 1 µM, seven diruthenium-carbohydrate conjugates strongly impaired parasite proliferation by >90%, while HFF viability was retained at 50% or more, and they were further subjected to the half-maximal inhibitory concentration (IC50) measurement on T. gondii β-gal. Results revealed that the biological activity of the hybrids was influenced both by the nature of the carbohydrate (glucose vs. galactose) appended on ruthenium complex and the type/length of the linker between the two units. 23 and 26, two galactose-based diruthenium conjugates, exhibited low IC50 values and reduced effect on HFF viability when applied at 2.5 µM (23: IC50 = 0.032 µM/HFF viability 92% and 26: IC50 = 0.153 µM/HFF viability 97%). Remarkably, compounds 23 and 26 performed significantly better than the corresponding carbohydrate non-modified diruthenium complexes, showing that this type of conjugates are a promising approach for obtaining new antiparasitic compounds with reduced toxicity. Full article
(This article belongs to the Special Issue Metal-Based Drugs: Past, Present and Future)
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34 pages, 2285 KiB  
Review
Plant Essential Oils as Healthy Functional Ingredients of Nutraceuticals and Diet Supplements: A Review
by Riccardo Matera, Elena Lucchi and Luca Valgimigli
Molecules 2023, 28(2), 901; https://doi.org/10.3390/molecules28020901 - 16 Jan 2023
Cited by 17 | Viewed by 5036
Abstract
Essential oils (EOs) are mixtures of volatile molecules endowed with health-promoting biological activities that go beyond their role as aromas and natural preservatives and can be exploited to develop functional foods and diet supplements. Their composition is briefly addressed along with regulatory aspects. [...] Read more.
Essential oils (EOs) are mixtures of volatile molecules endowed with health-promoting biological activities that go beyond their role as aromas and natural preservatives and can be exploited to develop functional foods and diet supplements. Their composition is briefly addressed along with regulatory aspects. The potential health benefit of human diet supplementation with EOs is outlined through a review of the recent literature on available clinical trials and preclinical research concerning EOs activity towards: (1) irritable bowel syndrome; (2) inflammatory bowel disease; (3) regulation of microbiota; (4) gastroprotection; (5) hepatoprotection; (6) protection of the urinary tract and diuresis; (7) management of metabolic disorders including hyperglycemia and hyperlipidemia; (8) anti-inflammatory and pain control; (9) immunomodulation and protection from influenza; and (10) neuroprotection and modulation of mood and cognitive performance. The emerging potential in such activities of selected EOs is given focus, particularly green and black cumin, bergamot, orange, myrtle, peppermint, sage, eucalyptus, lavender, thyme, lemon balm, ginger, and garlic. Full article
(This article belongs to the Special Issue Advances in Functional Foods)
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14 pages, 2309 KiB  
Article
A Comparative UHPLC-Q-Trap-MS/MS-Based Metabolomics Analysis to Distinguish Foeniculum vulgare Cultivars’ Antioxidant Extracts
by Maria Assunta Crescenzi, Gilda D’Urso, Sonia Piacente and Paola Montoro
Molecules 2023, 28(2), 900; https://doi.org/10.3390/molecules28020900 - 16 Jan 2023
Cited by 1 | Viewed by 1452
Abstract
Among the environmental factors, seasonality is the one which most affects the metabolome of a plant. Depending on the harvest season, the plant may have a variable content of certain metabolites and thus may have different biological properties. Foeniculum vulgare is an annual plant [...] Read more.
Among the environmental factors, seasonality is the one which most affects the metabolome of a plant. Depending on the harvest season, the plant may have a variable content of certain metabolites and thus may have different biological properties. Foeniculum vulgare is an annual plant whose cultivation creates large amounts of waste rich in bioactive compounds. The present investigation was performed with the aim of determining the amount of biologically active compounds in F. vulgare wastes obtained from varieties of different seasonality. Ten polyphenolic compounds were quantified in the little stems and leaves of Tiziano, Pegaso, and Preludio cultivars by ultra performance liquid chromatography (UPLC) hyphenated to QTRAP mass spectrometry by using the MRM (multiple reaction monitoring) method. The antioxidant activity of hydroalcoholic extracts was then evaluated using TEAC and DPPH spectrophotometric assays, followed by a multivariate statistical analysis to determine the correlation between metabolite expression and antioxidant activity. The Preludio variety, grown in summer, showed a higher content of bioactive compounds, which guarantees it a better antioxidant power; kaempferol 3-O-glucuronide, quercetin 3-O-glucuronide, and quercetin 3-O-glucoside are the polyphenolic compounds that could be mainly responsible for the antioxidant effect of fennel. The PLS chemometric model, which correlated quantitative data obtained by a sensitive and selective LC-ESI-QTrap-MS/MS analysis of antioxidant activity, resulted in a selective tool to detect the compounds responsible for the activity shown by the extracts in chemical tests. Full article
(This article belongs to the Special Issue Natural Polyphenols in Human Health)
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22 pages, 3051 KiB  
Article
Antioxidant and Antimicrobial Evaluations of Moringa oleifera Lam Leaves Extract and Isolated Compounds
by Mmabatho Kgongoane Segwatibe, Sekelwa Cosa and Kokoette Bassey
Molecules 2023, 28(2), 899; https://doi.org/10.3390/molecules28020899 - 16 Jan 2023
Cited by 9 | Viewed by 2760
Abstract
Moringa oleifera, native to India, grows in tropical and subtropical regions around the world and has valuable pharmacological properties such as anti-asthmatic, anti-diabetic, anti-inflammatory, anti-infertility, anti-cancer, anti-microbial, antioxidant, and many more. The purpose of this study was to assess the free radical [...] Read more.
Moringa oleifera, native to India, grows in tropical and subtropical regions around the world and has valuable pharmacological properties such as anti-asthmatic, anti-diabetic, anti-inflammatory, anti-infertility, anti-cancer, anti-microbial, antioxidant, and many more. The purpose of this study was to assess the free radical scavenging ability of two extracts and two pure compounds of M. oleifera Lam (hexane, ethanol, compound E3, and compound Ra) against reactive oxygen species, as well as their reducing power and antimicrobial activities. Bioautography antioxidant assay, 2,2-diphenyl-1-picrylhydrazyl (DPPH), hydrogen peroxide (H2O2) free radical scavenging, and iron (iii) (Fe3+ to Fe2+) chloride reducing power assays were used to assess the extracts’ qualitative and quantitative free radical scavenging activities. Furthermore, the extract and the compounds were tested against both Gram-positive and Gram-negative bacterial strains suspended in Mueller–Hinton Broth. The extracts and pure compounds showed noteworthy antioxidant potential, with positive compound bands in the Rf range of 0.05–0.89. DPPH), H2O2, and Fe3+ to Fe2+ reduction assays revealed that ethanol extract has a high antioxidant potential, followed by compound E3, compound Ra, and finally hexane extract. Using regression analysis, the half maximal inhibitory concentration (IC50) values for test and control samples were calculated. Compound Ra and ethanol exhibited high antioxidant activity at concentrations as low as ≈0.28 mg/mL in comparison with n-hexane extract, compound E3, ascorbic acid, and butylated hydroxytoluene standards. The radical scavenging activity of almost all M. oleifera plant extracts against DPPH was observed at 0.28 mg/mL; however, the highest activity was observed at the same concentration for ascorbic acid and butylated hydroxytoluene (BHT) with a low IC50 value of 0.08 mg/mL and compound Ra and ethanol with a low IC50 of 0.4 mg/mL, respectively. The extracts and pure compounds of M. oleifera have little to no antibacterial potential. M. oleifera extracts contain antioxidant agents efficient to alleviate degenerative conditions such as cancer and cardiovascular disease but have little activity against infectious diseases. Full article
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15 pages, 5223 KiB  
Article
Nanocapsule of MnS Nanopolyhedron Core@CoS Nanoparticle/Carbon Shell@Pure Carbon Shell as Anode Material for High-Performance Lithium Storage
by Peng Yang, Yongfeng Yuan, Dong Zhang, Qiuhe Yang, Shaoyi Guo and Jipeng Cheng
Molecules 2023, 28(2), 898; https://doi.org/10.3390/molecules28020898 - 16 Jan 2023
Cited by 6 | Viewed by 1696
Abstract
MnS has been explored as an anode material for lithium-ion batteries due to its high theoretical capacity, but low electronic conductivity and severe volume change induce low reversible capacity and poor cycling performance. In this work, the nanocapsule consisting of MnS nanopolyhedrons confined [...] Read more.
MnS has been explored as an anode material for lithium-ion batteries due to its high theoretical capacity, but low electronic conductivity and severe volume change induce low reversible capacity and poor cycling performance. In this work, the nanocapsule consisting of MnS nanopolyhedrons confined in independent, closed and conductive hollow polyhedral nanospheres is prepared by embedding MnCO3 nanopolyhedrons into ZIF-67, followed by coating of RF resin and gaseous sulfurization/carbonization. Benefiting from the unique nanocapsule structure, especially inner CoS/C shell and outer pure C shell, the MnS@CoS/C@C composite as anode material presents excellent cycling performance (674 mAh g−1 at 1 A g−1 after 300 cycles; 481 mAh g−1 at 5 A g−1 after 300 cycles) and superior rate capability (1133.3 and 650.6 mAh g−1 at 0.1 and 4 A g−1), compared to the control materials (MnS and MnS@CoS/C) and other MnS composites. Kinetics measurements further reveal a high proportion of the capacitive effect and low reaction impedance of MnS@CoS/C@C. SEM and TEM observation on the cycled electrode confirms superior structural stability of MnS@CoS/C@C during long-term cycles. Excellent lithium storage performance and the convenient synthesis strategy demonstrates that the MnS@CoS/C@C nanocapsule is a promising high-performance anode material. Full article
(This article belongs to the Special Issue Electrochemistry of Thin Films and Nanostructured Materials)
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44 pages, 5425 KiB  
Review
Shaking Things from the Ground-Up: A Systematic Overview of the Mechanochemistry of Hard and High-Melting Inorganic Materials
by Thomas Auvray and Tomislav Friščić
Molecules 2023, 28(2), 897; https://doi.org/10.3390/molecules28020897 - 16 Jan 2023
Cited by 8 | Viewed by 3077
Abstract
We provide a systematic overview of the mechanochemical reactions of inorganic solids, notably simple binary compounds, such as oxides, nitrides, carbides, sulphides, phosphides, hydrides, borides, borane derivatives, and related systems. Whereas the solid state has been traditionally considered to be of little synthetic [...] Read more.
We provide a systematic overview of the mechanochemical reactions of inorganic solids, notably simple binary compounds, such as oxides, nitrides, carbides, sulphides, phosphides, hydrides, borides, borane derivatives, and related systems. Whereas the solid state has been traditionally considered to be of little synthetic value by the broader community of synthetic chemists, the solid-state community, and in particular researchers focusing on the reactions of inorganic materials, have thrived in building a rich and dynamic research field based on mechanically-driven transformations of inorganic substances typically seen as inert and high-melting. This review provides an insight into the chemical richness of such mechanochemical reactions and, at the same time, offers their tentative categorisation based on transformation type, resulting in seven distinct groupings: (i) the formation of adducts, (ii) the reactions of dehydration; (iii) oxidation–reduction (redox) reactions; (iv) metathesis (or exchange) reactions; (v) doping and structural rearrangements, including reactions involving the reaction vessel (the milling jar); (vi) acid–base reactions, and (vii) other, mixed type reactions. At the same time, we offer a parallel description of inorganic mechanochemical reactions depending on the reaction conditions, as those that: (i) take place under mild conditions (e.g., manual grinding using a mortar and a pestle); (ii) proceed gradually under mechanical milling; (iii) are self-sustained and initiated by mechanical milling, i.e., mechanically induced self-propagating reactions (MSRs); and (iv) proceed only via harsh grinding and are a result of chemical reactivity under strongly non-equilibrium conditions. By elaborating on typical examples and general principles in the mechanochemistry of hard and high-melting substances, this review provides a suitable complement to the existing literature, focusing on the properties and mechanochemical reactions of inorganic solids, such as nanomaterials and catalysts. Full article
(This article belongs to the Special Issue A Themed Issue in Honor of Professor Robin D. Rogers - "A Scientific Journey within Green Chemistry")
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14 pages, 1723 KiB  
Article
New Copper(II)-L-Dipeptide-Bathophenanthroline Complexes as Potential Anticancer Agents—Synthesis, Characterization and Cytotoxicity Studies—And Comparative DNA-Binding Study of Related Phen Complexes
by Carlos Y. Fernández, Natalia Alvarez, Analu Rocha, Javier Ellena, Antonio J. Costa-Filho, Alzir A. Batista and Gianella Facchin
Molecules 2023, 28(2), 896; https://doi.org/10.3390/molecules28020896 - 16 Jan 2023
Cited by 7 | Viewed by 2045
Abstract
Searching for new copper compounds which may be useful as antitumor drugs, a series of new [Cu(L-dipeptide)(batho)] (batho:4,7-diphenyl-1,10-phenanthroline, L-dipeptide: Gly-Val, Gly-Phe, Ala-Gly, Ala-Ala, Ala-Phe, Phe-Ala, Phe-Val and Phe-Phe) complexes were synthesized and characterized. To interpret the experimental IR spectra, [Cu(ala-gly)(batho)] was modelled in [...] Read more.
Searching for new copper compounds which may be useful as antitumor drugs, a series of new [Cu(L-dipeptide)(batho)] (batho:4,7-diphenyl-1,10-phenanthroline, L-dipeptide: Gly-Val, Gly-Phe, Ala-Gly, Ala-Ala, Ala-Phe, Phe-Ala, Phe-Val and Phe-Phe) complexes were synthesized and characterized. To interpret the experimental IR spectra, [Cu(ala-gly)(batho)] was modelled in the gas phase using DFT at the B3LYP/LANL2DZ level of theory and the calculated vibrational frequencies were analyzed. Solid-state characterization is in agreement with pentacoordinate complexes of the general formula [Cu(L-dipeptide)(batho)]·x solvent, similar to other [Cu(L-dipeptide)(diimine)] complexes. In solution, the major species are heteroleptic, as in the solid state. The mode of binding to the DNA was evaluated by different techniques, to understand the role of the diimine and the dipeptide. To this end, studies were also performed with complexes [CuCl2(diimine)], [Cu(L-dipeptide)(diimine)] and free diimines, with phenanthroline, neocuproine and 3,4,7,8-tetramethyl-phenanthroline. The cytotoxicity of the complexes was determined on human cancer cell lines MDA-MB-231, MCF-7 (breast, the first triple negative), and A549 (lung epithelial) and non-tumor cell lines MRC-5 (lung) and MCF-10A (breast). [Cu(L-dipeptide)(batho)] complexes are highly cytotoxic as compared to cisplatin and [Cu(L-dipeptide)(phenanthroline)] complexes, being potential candidates to study their in vivo activity in the treatments of aggressive tumors for which there is no curative pharmacological treatment. Full article
(This article belongs to the Special Issue Metal-Based Drugs Ⅱ)
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28 pages, 8328 KiB  
Article
A Bridge too Far? Comparison of Transition Metal Complexes of Dibenzyltetraazamacrocycles with and without Ethylene Cross-Bridges: X-ray Crystal Structures, Kinetic Stability, and Electronic Properties
by Ashlie N. Walker, Megan A. Ayala, Somrita Mondal, Mackenzie C. Bergagnini, Phuong John D. Bui, Stephanie N. Chidester, Chad I. Doeden, Louise Esjornson, Brian R. Sweany, Leslie Garcia, Jeanette A. Krause, Allen G. Oliver, Timothy J. Prior and Timothy J. Hubin
Molecules 2023, 28(2), 895; https://doi.org/10.3390/molecules28020895 - 16 Jan 2023
Cited by 1 | Viewed by 1683
Abstract
Tetraazamacrocycles, cyclic molecules with four nitrogen atoms, have long been known to produce highly stable transition metal complexes. Cross-bridging such molecules with two-carbon chains has been shown to enhance the stability of these complexes even further. This provides enough stability to use the [...] Read more.
Tetraazamacrocycles, cyclic molecules with four nitrogen atoms, have long been known to produce highly stable transition metal complexes. Cross-bridging such molecules with two-carbon chains has been shown to enhance the stability of these complexes even further. This provides enough stability to use the resulting compounds in applications as diverse and demanding as aqueous, green oxidation catalysis all the way to drug molecules injected into humans. Although the stability of these compounds is believed to result from the increased rigidity and topological complexity imparted by the cross-bridge, there is insufficient experimental data to exclude other causes. In this study, standard organic and inorganic synthetic methods were used to produce unbridged dibenzyl tetraazamacrocycle complexes of Co, Ni, Cu, and Zn that are analogues of known cross-bridged tetraazamacrocycles and their transition metal complexes to allow direct comparison of molecules that are identical except for the cross-bridge. The syntheses of the known tetraazamacrocycles and the new transition metal complexes were successful with high yields and purity. Initial chemical characterization of the complexes was conducted by UV-Visible spectroscopy, while cyclic voltammetry showed more marked differences in electronic properties from bridged versions. Direct comparison studies of the unbridged and bridged compounds’ kinetic stabilities, as demonstrated by decomposition using high acid concentration and elevated temperature, showed that the cyclen-based complex stability did not benefit from cross-bridging. This is likely due to poor complementarity with the Cu2+ ion while cyclam-based complexes benefited greatly. We conclude that ligand–metal complementarity must be maintained in order for the topological and rigidity constraints imparted by the cross-bridge to contribute significantly to complex robustness. Full article
(This article belongs to the Special Issue Recent Advance in Transition Metal Complexes and Their Applications)
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16 pages, 4254 KiB  
Article
Preparation, Purification and Characterization of Antibacterial and ACE Inhibitory Peptides from Head Protein Hydrolysate of Kuruma Shrimp, Marsupenaeus japonicus
by Jie Zhou, Qiuyu Han, Tomoyuki Koyama and Shoichiro Ishizaki
Molecules 2023, 28(2), 894; https://doi.org/10.3390/molecules28020894 - 16 Jan 2023
Cited by 3 | Viewed by 1806
Abstract
Kuruma shrimp (Marsupenaeus japonicus) heads, as the main by-product of the seafood processing industry, are rich in underutilized high-quality protein. After papain hydrolysis at 50 °C for 4 h, the protein hydrolysate of shrimp heads was found to show notable antibacterial and [...] Read more.
Kuruma shrimp (Marsupenaeus japonicus) heads, as the main by-product of the seafood processing industry, are rich in underutilized high-quality protein. After papain hydrolysis at 50 °C for 4 h, the protein hydrolysate of shrimp heads was found to show notable antibacterial and angiotensin I-converting enzyme (ACE) inhibitory activities. After purification using two stages of revered-phase high-performance liquid chromatography (RP-HPLC), the antibacterial peptide VTVP and the ACE inhibitory peptide ARL/I were successfully identified from most active fractions by LC–MS/MS. Peptide VTVP was a desirable hydrophobic peptide, with a MIC value in the range from 1.62 to 8.03 mM against all tested pathogens. Peptide ARL/I exhibited potent ACE inhibitory activity, with an IC50 value of 125.58 µM, and was found to be a competitive inhibitor based on the Lineweaver–Burk plot. Moreover, the result of the molecular docking simulation indicated that the interaction binding between ARL/I and ACE was mainly stabilized by hydrogen bonds, as well as forming a coordinate bond with the Zn2+ site. The purified peptides did not show hemolytic activity toward rabbit erythrocytes. To sum up, the bioactive peptides isolated from shrimp heads could be applicable for food or pharmaceutical areas as promising ingredients. Full article
(This article belongs to the Special Issue 2nd Edition of Food Bioactives: Chemical Challenges and Bio-Opportunities)
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12 pages, 1873 KiB  
Article
Selenylated Imidazo[1,2-a]pyridine Induces Cell Senescence and Oxidative Stress in Chronic Myeloid Leukemia Cells
by Gabriella Teles Burkner, Dhébora Albuquerque Dias, Kamylla Fernanda Souza de Souza, Anna Júlia Papa de Araújo, Denise Caroline Luiz Soares Basilio, Fernanda Tondello Jacobsen, Ana Carolina Rabello de Moraes, Saulo Euclides Silva-Filho, Marcos Filipe de Oliveira Cavalcante, Cassio Augusto de Oliveira Moraes, Sumbal Saba, Maria Lígia Rodrigues Macedo, Edgar Julian Paredes-Gamero, Jamal Rafique and Eduardo Benedetti Parisotto
Molecules 2023, 28(2), 893; https://doi.org/10.3390/molecules28020893 - 16 Jan 2023
Cited by 6 | Viewed by 1835
Abstract
Imidazo[1,2-a]pyridines (IPs) have been studied regarding drug development. The objective of this work was to evaluate the antileukemic capacity of IP derivatives by screening their ability as a pro-oxidant. IP derivatives were synthesized and oral bioavailability and toxicity were analyzed in [...] Read more.
Imidazo[1,2-a]pyridines (IPs) have been studied regarding drug development. The objective of this work was to evaluate the antileukemic capacity of IP derivatives by screening their ability as a pro-oxidant. IP derivatives were synthesized and oral bioavailability and toxicity were analyzed in silico. Redox screening was performed on human Kasumi, KG-1, K562, and Jurkat leukemia cells. The IP derivative and the most responsive leukemic cell were selected for cytotoxicity, cell proliferation, cell senescence, and oxidative stress assays. The predictive toxicity analysis showed a possible effect on the reproductive system, but without mutagenic, carcinogenic, or irritability effects. MRK-107 against K562 cells was the compound that showed the best redox profile. MRK-107 did not induce cell death in K562 and monocyte cells. However, this compound was able to decrease cell proliferation and increase cell senescence after 48 and 72 h. Furthermore, MRK-107 induced oxidative stress in K562 cells after 72 h, increasing lipid peroxidation and decreasing reduced glutathione (GSH) contents. This study demonstrated that MRK-107-induced senescence with the involvement of oxidative stress is a possible mechanism of action, addressing this compound as a potential antitumor drug against chronic myeloid leukemia. Full article
(This article belongs to the Special Issue Chalcogens in Medicinal Chemistry)
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16 pages, 1547 KiB  
Article
Synthesis and Behavior of Hexamethylenetetramine-Based Ionic Liquids as an Active Ingredient in Latent Curing Formulations with Ethylene Glycol for DGEBA
by Dawid Zielinski, Andrea Szpecht, Paulina Hinc and Marcin Smiglak
Molecules 2023, 28(2), 892; https://doi.org/10.3390/molecules28020892 - 16 Jan 2023
Cited by 4 | Viewed by 2733
Abstract
The paper presents the preparation of new ionic liquids based on hexamethylenetetramine with bis(trifluoromethanesulfonyl)imide and dicyanamide anion, which were characterized in detail in terms of their purity (Ion Chromatography) and thermal properties (Differential Scanning Calorimetry), as well as stability. The obtained substances were [...] Read more.
The paper presents the preparation of new ionic liquids based on hexamethylenetetramine with bis(trifluoromethanesulfonyl)imide and dicyanamide anion, which were characterized in detail in terms of their purity (Ion Chromatography) and thermal properties (Differential Scanning Calorimetry), as well as stability. The obtained substances were used to develop curing systems with ethylene glycol, which were successfully tested for their application with bisphenol A diglycidyl ether molecule. In addition, the curing process and its relationship to the structure of the ionic liquid are characterized in detail. The research showed that hexamethylenetetramine-based new ionic liquids can be successfully designed using well-known and simple synthetic methods—the Delepine reaction. Moreover, attention was paid to their stability, related limitations, and the application of hexamethylenetetramine-based ionic liquids in epoxy-curing systems. Full article
(This article belongs to the Special Issue Feature Papers in Materials Chemistry)
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17 pages, 798 KiB  
Article
Commiphora wildii Merxm. Essential Oil: Natural Heptane Source and Co-Product Valorization
by Djallel Mansouri, Anne Landreau, Thomas Michel, Clément De Saint Jores, Bienvenue Razafimandimby, Marie Kempf, Stéphane Azoulay, Nicolas Papaiconomou and Xavier Fernandez
Molecules 2023, 28(2), 891; https://doi.org/10.3390/molecules28020891 - 16 Jan 2023
Viewed by 1933
Abstract
As an alternative to fossil volatile hydrocarbon solvents used nowadays in perfumery, investigation on essential oil of Commiphora wildii Merxm. oleo gum resin as a source of heptane is reported here. Heptane, representing up to 30 wt-% of this oleo gum resin, was [...] Read more.
As an alternative to fossil volatile hydrocarbon solvents used nowadays in perfumery, investigation on essential oil of Commiphora wildii Merxm. oleo gum resin as a source of heptane is reported here. Heptane, representing up to 30 wt-% of this oleo gum resin, was successfully isolated from the C. wildii essential oil, using an innovative double distillation process. Isolated heptane was then used as a solvent in order to extract some noble plants of perfumery. It was found that extracts obtained with this solvent were more promising in terms of sensory analysis than those obtained from fossil-based heptane. In addition, in order to valorize the essential oil depleted from heptane, chemical composition of this oil was found to obtain, and potential biological activity properties were studied. A total of 172 different compounds were identified by GC-MS in the remaining oil. In vitro tests—including hyaluronidase, tyrosinase, antioxidant, elastase and lipoxygenase, as well as inhibitory tests against two yeasts and 21 bacterial strains commonly found on the skin—were carried out. Overall, bioassays results suggest this heptane-depleted essential oil is a promising active ingredient for cosmetic applications. Full article
(This article belongs to the Special Issue Chemistry of Essential Oils: The Incredible Wealth of Plants)
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13 pages, 2382 KiB  
Communication
New Insights into Conformationally Restricted Carbonic Anhydrase Inhibitors
by Jacob Combs, Murat Bozdag, Lochlin D. Cravey, Anusha Kota, Robert McKenna, Andrea Angeli, Fabrizio Carta and Claudiu T. Supuran
Molecules 2023, 28(2), 890; https://doi.org/10.3390/molecules28020890 - 16 Jan 2023
Cited by 5 | Viewed by 1676
Abstract
This paper reports an investigation into the impact of pyridyl functional groups in conjunction with hydroxide-substituted benzenesulfonamides on the inhibition of human carbonic anhydrase (CA; EC 4.2.1.1) enzymes. These compounds were tested in vitro of CA II and CA IX, two physiologically important [...] Read more.
This paper reports an investigation into the impact of pyridyl functional groups in conjunction with hydroxide-substituted benzenesulfonamides on the inhibition of human carbonic anhydrase (CA; EC 4.2.1.1) enzymes. These compounds were tested in vitro of CA II and CA IX, two physiologically important CA isoforms. The most potent inhibitory molecules against CA IX, 3g, 3h, and 3k, were studied to understand their binding modes via X-ray crystallography in adduct with CA II and CA IX-mimic. This research further adds to the field of CA inhibitors to better understand ligand selectivity between isoforms found in humans. Full article
(This article belongs to the Special Issue Enzyme Inhibitors: Design, Synthesis and Biological Evaluation)
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14 pages, 2107 KiB  
Article
Isolation and Characterization of Collagen and Collagen Peptides with Hyaluronidase Inhibition Activity Derived from the Skin of Marlin (Istiophoridae)
by Qiu-Yu Han, Tomoyuki Koyama, Shugo Watabe, Yuji Nagashima and Shoichiro Ishizaki
Molecules 2023, 28(2), 889; https://doi.org/10.3390/molecules28020889 - 16 Jan 2023
Cited by 3 | Viewed by 2274
Abstract
Type I and V collagens are the major components of fibrillogenic proteins in fish skin, and their hydrolysis products possess hyaluronidase inhibitory activity. In this study, for the first time, type I and V collagens were isolated from the skin of shortbill spearfish [...] Read more.
Type I and V collagens are the major components of fibrillogenic proteins in fish skin, and their hydrolysis products possess hyaluronidase inhibitory activity. In this study, for the first time, type I and V collagens were isolated from the skin of shortbill spearfish and striped marlin. Type I (2α1[I]α2[I]) and type V (α1[V]α3[V]α2[V]) collagens composed of distinct α-peptide chains with comparable structures were investigated using sodium dodecyl sulfate polyacrylamide gel electrophoresis (SDS-PAGE) and UV spectrophotometric chromatography. After enzymatic digestion, the collagen peptides were purified by using ultrafiltration (30 KDa) and high-performance liquid chromatography (RP-HPLC) to yield CPI-F3 and CPV-F4 fractions with strong hyaluronidase inhibition rates (42.17% and 30.09%, respectively). Based on the results of simulated gastrointestinal fluid, temperature, and pH stability assays, CPI-F3 and CPV-F4 exhibited stability in gastric fluid and showed no significant changes under the temperature range from 50 to 70 °C (p > 0.05). The results of this first research on the bioactivity of type V collagen peptides provide valuable information for the biomedical industry and show the potential for future bioactivity investigations of type V collagen and its peptides. Full article
(This article belongs to the Special Issue 2nd Edition of Food Bioactives: Chemical Challenges and Bio-Opportunities)
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8 pages, 1254 KiB  
Communication
Determination of Free Histidine in Complex Hair Care Products with Minimum Sample Preparation Using Cation-Exchange Chromatography and Post Column Derivatization
by Apostolia Tsiasioti, Constantinos K. Zacharis and Paraskevas D. Tzanavaras
Molecules 2023, 28(2), 888; https://doi.org/10.3390/molecules28020888 - 16 Jan 2023
Cited by 2 | Viewed by 1314
Abstract
In this communication, we describe the first analytical method for the determination of free histidine in hair care products (shampoos and conditioners). Cation-exchange chromatography combined with postcolumn derivatization and fluorimetric detection enabled the accurate (recovery: 83.5–114.8%) and precise (2.4–5.6% RSD) determination of free [...] Read more.
In this communication, we describe the first analytical method for the determination of free histidine in hair care products (shampoos and conditioners). Cation-exchange chromatography combined with postcolumn derivatization and fluorimetric detection enabled the accurate (recovery: 83.5–114.8%) and precise (2.4–5.6% RSD) determination of free histidine without matrix interferences at concentration levels down to 1.5 mg kg−1. Real commercially available samples were found to contain the amino acid at levels ranging between 70 and 535 mg kg−1. Full article
(This article belongs to the Special Issue Derivatization in Analytical Chemistry-II)
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41 pages, 3920 KiB  
Review
Major Phytochemicals: Recent Advances in Health Benefits and Extraction Method
by Ashwani Kumar, Nirmal P, Mukul Kumar, Anina Jose, Vidisha Tomer, Emel Oz, Charalampos Proestos, Maomao Zeng, Tahra Elobeid, Sneha K and Fatih Oz
Molecules 2023, 28(2), 887; https://doi.org/10.3390/molecules28020887 - 16 Jan 2023
Cited by 38 | Viewed by 11032
Abstract
Recent scientific studies have established a relationship between the consumption of phytochemicals such as carotenoids, polyphenols, isoprenoids, phytosterols, saponins, dietary fibers, polysaccharides, etc., with health benefits such as prevention of diabetes, obesity, cancer, cardiovascular diseases, etc. This has led to the popularization of [...] Read more.
Recent scientific studies have established a relationship between the consumption of phytochemicals such as carotenoids, polyphenols, isoprenoids, phytosterols, saponins, dietary fibers, polysaccharides, etc., with health benefits such as prevention of diabetes, obesity, cancer, cardiovascular diseases, etc. This has led to the popularization of phytochemicals. Nowadays, foods containing phytochemicals as a constituent (functional foods) and the concentrated form of phytochemicals (nutraceuticals) are used as a preventive measure or cure for many diseases. The health benefits of these phytochemicals depend on their purity and structural stability. The yield, purity, and structural stability of extracted phytochemicals depend on the matrix in which the phytochemical is present, the method of extraction, the solvent used, the temperature, and the time of extraction. Full article
(This article belongs to the Special Issue Determination, Health Benefits and Metabolism of Food Bioactives)
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12 pages, 1119 KiB  
Article
Polyoxypregnane Glycosides from Root of Marsdenia tenacissima and Inhibited Nitric Oxide Levels in LPS Stimulated RAW 264.7 Cells
by Zhi Na, Pianchou Gongpan and Qingfei Fan
Molecules 2023, 28(2), 886; https://doi.org/10.3390/molecules28020886 - 16 Jan 2023
Cited by 1 | Viewed by 1398
Abstract
Six new polyoxypregnane glycosides, marstenacisside F1–F3 (1–3), G1–G2 (4–5) and H1 (6), as well as 3-O-β-D-glucopyranosyl-(1→4)-6-deoxy-3-O-methyl-β-D-allopyranosyl-(1→4)-β-D-oleandropyranosyl-11α,12β-di-O-benzoyl-tenacigenin B (7), were isolated from the roots of Marsdenia tenacissima [...] Read more.
Six new polyoxypregnane glycosides, marstenacisside F1–F3 (1–3), G1–G2 (4–5) and H1 (6), as well as 3-O-β-D-glucopyranosyl-(1→4)-6-deoxy-3-O-methyl-β-D-allopyranosyl-(1→4)-β-D-oleandropyranosyl-11α,12β-di-O-benzoyl-tenacigenin B (7), were isolated from the roots of Marsdenia tenacissima. Their structures were established by an extensive interpretation of their 1D and 2D NMR and HRESIMS data. Compounds 1–7 were tenacigenin B derivatives with an oligosaccharide chain at C-3. This was the first time that compound 7 had been isolated from the title plant and its 1H and 13C NMR data were reported. Compounds 4 and 5 were the first examples of C21 steroid glycoside bearing unique β-glucopyranosyl-(1→4)-β-glucopyranose sugar moiety. All the isolated compounds were evaluated for anti-inflammatory activity by inhibiting nitric oxide (NO) production in the lipopolysaccharide-induced RAW 264.7 cells. The results showed that marstenacisside F1 and F2 exhibited significant NO inhibitory activity with an inhibition rate of 48.19 ± 4.14% and 70.33 ± 5.39%, respectively, at 40 μM, approximately equal to the positive control (L-NMMA, 68.03 ± 0.72%). Full article
(This article belongs to the Special Issue Natural Products from Medicinal Plants)
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10 pages, 1328 KiB  
Review
Ca2+-Sensitive Potassium Channels
by Razan Orfali and Nora Albanyan
Molecules 2023, 28(2), 885; https://doi.org/10.3390/molecules28020885 - 16 Jan 2023
Cited by 9 | Viewed by 2105
Abstract
The Ca2+ ion is used ubiquitously as an intracellular signaling molecule due to its high external and low internal concentration. Many Ca2+-sensing ion channel proteins have evolved to receive and propagate Ca2+ signals. Among them are the Ca2+ [...] Read more.
The Ca2+ ion is used ubiquitously as an intracellular signaling molecule due to its high external and low internal concentration. Many Ca2+-sensing ion channel proteins have evolved to receive and propagate Ca2+ signals. Among them are the Ca2+-activated potassium channels, a large family of potassium channels activated by rises in cytosolic calcium in response to Ca2+ influx via Ca2+-permeable channels that open during the action potential or Ca2+ release from the endoplasmic reticulum. The Ca2+ sensitivity of these channels allows internal Ca2+ to regulate the electrical activity of the cell membrane. Activating these potassium channels controls many physiological processes, from the firing properties of neurons to the control of transmitter release. This review will discuss what is understood about the Ca2+ sensitivity of the two best-studied groups of Ca2+-sensitive potassium channels: large-conductance Ca2+-activated K+ channels, KCa1.1, and small/intermediate-conductance Ca2+-activated K+ channels, KCa2.x/KCa3.1. Full article
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4 pages, 2251 KiB  
Correction
Correction: Thang et al. Effects of Different Colored LEDs on the Enhancement of Biologically Active Ingredients in Callus Cultures of Gynura procumbens (Lour.) Merr. Molecules 2019, 24, 4336
by Thang Tung Lian, Myat Myat Moe, Yong Ju Kim and Keuk Soo Bang
Molecules 2023, 28(2), 884; https://doi.org/10.3390/molecules28020884 - 16 Jan 2023
Viewed by 904
Abstract
There were some errors in the original publication [...] Full article
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