Molecules

20 pages, 2839 KiB

Open AccessArticle

Synthesis of MeON-Glycoside Derivatives of Oleanolic Acid by Neoglycosylation and Evaluation of Their Cytotoxicity against Selected Cancer Cell Lines

by Zhichao Du, Guolong Li, Xiaoyang Zhou and Jian Zhang

Molecules 2021, 26(3), 772; https://doi.org/10.3390/molecules26030772 - 2 Feb 2021

Cited by 6 | Viewed by 3439

Abstract

A series of C-3 and C-28 MeON-neoglycosides of oleanolic acid were designed and synthesized by neoglycosylation as potential antiproliferative agents. Their cytotoxicity was evaluated in vitro against five human cancer cell lines: human non-small cell lung cancer cell line (A549), human melanoma cell [...] Read more.

A series of C-3 and C-28 MeON-neoglycosides of oleanolic acid were designed and synthesized by neoglycosylation as potential antiproliferative agents. Their cytotoxicity was evaluated in vitro against five human cancer cell lines: human non-small cell lung cancer cell line (A549), human melanoma cell line (A375), human colon cancer cell line (HCT116), human liver carcinoma cell line (HepG2), human breast adenocarcinoma cell line (MCF-7) by the Cell Counting Kit-8 (CCK-8) assay. Most of C-3 and C-28 MeON-neoglycosides of oleanolic acid exhibited notably inhibitory effects against the tested cancer cells and more sensitive to HepG2 cells than 5-Fluorouracil (5-FU). Structure-activities relationship (SAR) analysis revealed that sugar types and the d/l configuration of sugars would significantly affect their antiproliferative activities of neoglycosides. Among them, compound 8a (28-N-methoxyaminooleanane-β-d-glucoside) exhibited the most potent antiproliferative activities against HepG2 cells with IC₅₀ values of 2.1 µM. Further pharmacological experiments revealed that compound 8a could cause morphological changes and cell cycle arrest at G0/G1 phase and induce apoptosis in HepG2 cells. These results suggested that neoglycosylation could provide a rapid strategy for the discovery of potential antiproliferative agents and their possible pharmacological mechanisms need more further research. Full article

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15 pages, 2399 KiB

Open AccessArticle

Design, Synthesis and Biological Evaluation of New Pyrimidine Derivatives as Anticancer Agents

by Valentina Noemi Madia, Alice Nicolai, Antonella Messore, Alessandro De Leo, Davide Ialongo, Valeria Tudino, Francesco Saccoliti, Daniela De Vita, Luigi Scipione, Marco Artico, Samanta Taurone, Ludovica Taglieri, Roberto Di Santo, Susanna Scarpa and Roberta Costi

Molecules 2021, 26(3), 771; https://doi.org/10.3390/molecules26030771 - 2 Feb 2021

Cited by 21 | Viewed by 4489

Abstract

Background: Anticancer drug resistance is a challenging phenomenon of growing concern which arises from alteration in drug targets. Despite the fast speed of new chemotherapeutic agent design, the increasing prevalence of this phenomenon requires further research and treatment development. Recently, we reported a [...] Read more.

Background: Anticancer drug resistance is a challenging phenomenon of growing concern which arises from alteration in drug targets. Despite the fast speed of new chemotherapeutic agent design, the increasing prevalence of this phenomenon requires further research and treatment development. Recently, we reported a new aminopyrimidine compound—namely RDS 344—as a potential innovative anticancer agent. Methods: Herein, we report the design, synthesis, and anti-proliferative activity of new aminopyrimidine derivatives structurally related to RDS 3442 obtained by carrying out substitutions at position 6 of the pyrimidine core and/or on the 2-aniline ring of our hit. The ability to inhibit cell proliferation was evaluated on different types of tumors, glioblastoma, triple-negative breast cancer, oral squamous cell carcinomas and colon cancer plus on human dermal fibroblasts chosen as control of normal cells. Results: The most interesting compound was the N-benzyl counterpart of RDS 3442, namely 2a, that induced a significant decrease in cell viability in all the tested tumor cell lines, with EC₅₀s ranging from 4 and 8 μM, 4–13 times more active of hit. Conclusions: These data suggest a potential role for this class of molecules as promising tool for new approaches in treating cancers of different histotype. Full article

(This article belongs to the Section Medicinal Chemistry)

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15 pages, 299 KiB

Open AccessArticle

The Influence of Hydrolytic Enzymes on Tannin Adsorption-Desorption onto Grape Cell Walls in a Wine-Like Matrix

by Andrea Osete-Alcaraz, Encarna Gómez-Plaza, Pilar Martínez-Pérez, Florent Weiller, Julia Schückel, William G.T. Willats, John P. Moore, José M. Ros-García and Ana B. Bautista-Ortín

Molecules 2021, 26(3), 770; https://doi.org/10.3390/molecules26030770 - 2 Feb 2021

Cited by 11 | Viewed by 3536

Abstract

This study evaluates the capacity of four hydrolytic enzymes to limit the interactions between grape cell-walls and tannins and/or to favor tannin desorption. Adsorption and desorption tests were conducted by mixing a commercial seed tannin with purified skin cell-walls from Syrah grapes, in [...] Read more.

This study evaluates the capacity of four hydrolytic enzymes to limit the interactions between grape cell-walls and tannins and/or to favor tannin desorption. Adsorption and desorption tests were conducted by mixing a commercial seed tannin with purified skin cell-walls from Syrah grapes, in the presence or absence of hydrolytic enzymes, in a model-wine solution. The effects of the enzymes were evaluated by measuring the tannins in solution by High Performance Liquid Chromatography (HPLC) and the changes in the cell wall polysaccharide network by Comprehensive Microarray Polymer Profiling (COMPP) while the polysaccharides liberated from cell walls were analyzed by Size Exclusion Chromatography (SEC). The results showed that the enzymes limited the interaction between tannins and cell walls, especially cellulase, pectinase and xylanase, an effect associated with the cell wall structural modifications caused by the enzymes, which reduced their capacity to bind tannins. With regards to the tannin desorption process, enzymes did not play a significant role in liberating bound tannins. Those enzymes that showed the highest effect in limiting the adsorption of tannins and in disorganizing the cell wall structure, cellulase and pectinase, did not lead to a desorption of bound tannins, although they still showed a capacity of affecting cell wall structure. The results indicate that enzymes are not able to access those polysaccharides where tannins are bound, thus, they are not a useful tool for desorbing tannins from cell walls. The practical importance implications of these findings are discussed in the manuscript. Full article

(This article belongs to the Special Issue Wine Chemistry: The Key behind Wine Quality)

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14 pages, 2292 KiB

Open AccessArticle

New Pharmaceutical Salts of Trazodone

by Jolanta Jaśkowska, Przemysław Zaręba, Anna Drabczyk, Agnieszka Kozak, Izabela D. Madura, Zbigniew Majka and Edyta Pindelska

Molecules 2021, 26(3), 769; https://doi.org/10.3390/molecules26030769 - 2 Feb 2021

Cited by 2 | Viewed by 4922

Abstract

New pharmaceutically acceptable salts of trazodone (trazodone hydrogen bromide and trazodone 1-hydroxy-2-naphthonic acid) for the treatment of central nervous system disorders are synthesized and described. Although trazodone salts are poorly crystalline, single-crystal X-ray diffraction data for trazodone 1-hydroxy-2-naphthonic acid were collected and analyzed [...] Read more.

New pharmaceutically acceptable salts of trazodone (trazodone hydrogen bromide and trazodone 1-hydroxy-2-naphthonic acid) for the treatment of central nervous system disorders are synthesized and described. Although trazodone salts are poorly crystalline, single-crystal X-ray diffraction data for trazodone 1-hydroxy-2-naphthonic acid were collected and analyzed as well as compared to the previously described crystal structure of commercially available trazodone hydrochloride. The powder samples of all new salts were characterized by Fourier transform infrared spectroscopy, X-ray diffraction and ¹³C solid-state nuclear magnetic resonance spectroscopy. Spectroscopic studies were supported by gauge including projector augmented wave (GIPAW) calculations of carbon chemical shielding constants. The main goal of our research was to find salts with better physicochemical properties and to make an attempt to associate them with both the anion structure and the most prominent interactions exhibited by the protonated trazodone cation. The dissolution profiles of trazodone from tablets prepared from various salts with lactose monohydrate were investigated. The studies revealed that salts with simple anions show a fast release of the drug while the presence of more complex anion, more strongly interacting with the cation, effects a slow-release profile of the active substance and can be used for the preparation of the tables with a delay or prolonged mode of action. Full article

(This article belongs to the Section Medicinal Chemistry)

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21 pages, 4459 KiB

Open AccessArticle

Phytochemistry, Bioactivities, Pharmacokinetics and Toxicity Prediction of Selaginella repanda with Its Anticancer Potential against Human Lung, Breast and Colorectal Carcinoma Cell Lines

by Mohd Adnan, Arif Jamal Siddiqui, Walid Sabri Hamadou, Mitesh Patel, Syed Amir Ashraf, Arshad Jamal, Amir Mahgoub Awadelkareem, Manojkumar Sachidanandan, Mejdi Snoussi and Vincenzo De Feo

Molecules 2021, 26(3), 768; https://doi.org/10.3390/molecules26030768 - 2 Feb 2021

Cited by 30 | Viewed by 4531

Abstract

In this study, we investigated the bioactive potential (antibacterial and antioxidant), anticancer activity and detailed phytochemical analysis of Selaginellarepanda (S. repanda) ethanolic crude extract for the very first time using different in vitro approaches. Furthermore, computer-aided prediction of pharmacokinetic properties and safety [...] Read more.

In this study, we investigated the bioactive potential (antibacterial and antioxidant), anticancer activity and detailed phytochemical analysis of Selaginellarepanda (S. repanda) ethanolic crude extract for the very first time using different in vitro approaches. Furthermore, computer-aided prediction of pharmacokinetic properties and safety profile of the identified phytoconstituents were also employed in order to provide some useful insights for drug discovery. S. repanda, which is a rich source of potent natural bioactive compounds, showed promising antibacterial activity against the tested pathogenic bacteria (S. aureus, P. aeruginosa, E. coli and S. flexneri). The crude extract displayed favorable antioxidant activity against both 2,2-diphenyl-1-picrylhydrazyl (DPPH) (IC₅₀ = 231.6 μg/mL) and H₂O₂ (IC₅₀ = 288.3 μg/mL) molecules. S. repanda also showed favorable and effective anticancer activity against all three malignant cancer cells in a dose/time dependent manner. Higher activity was found against lung (A549) (IC₅₀ = 341.1 μg/mL), followed by colon (HCT-116) (IC₅₀ = 378.8 μg/mL) and breast (MCF-7) (IC₅₀ = 428.3 μg/mL) cancer cells. High resolution-liquid chromatography–mass spectrometry (HR-LC–MS) data of S. repanda crude extract revealed the presence of diverse bioactive/chemical components, including fatty acids, alcohol, sugar, flavonoids, alkaloids, terpenoids, coumarins and phenolics, which can be the basis and major cause for its bioactive potential. Therefore, achieved results from this study confirmed the efficacy of S. repanda and a prospective source of naturally active biomolecules with antibacterial, antioxidant and anticancer potential. These phytocompounds alone with their favorable pharmacokinetics profile suggests good lead and efficiency of S. repanda with no toxicity risks. Finally, further in vivo experimental investigations can be promoted as probable candidates for various therapeutic functions, drug discovery and development. Full article

(This article belongs to the Special Issue Biological Activities of Traditional Medicinal Plants)

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23 pages, 3105 KiB

Open AccessArticle

NMR and LC-MS-Based Metabolomics to Study Osmotic Stress in Lignan-Deficient Flax

by Kamar Hamade, Ophélie Fliniaux, Jean-Xavier Fontaine, Roland Molinié, Elvis Otogo Nnang, Solène Bassard, Stéphanie Guénin, Laurent Gutierrez, Eric Lainé, Christophe Hano, Serge Pilard, Akram Hijazi, Assem El Kak and François Mesnard

Molecules 2021, 26(3), 767; https://doi.org/10.3390/molecules26030767 - 2 Feb 2021

Cited by 15 | Viewed by 3837

Abstract

Lignans, phenolic plant secondary metabolites, are derived from the phenylpropanoid biosynthetic pathway. Although, being investigated for their health benefits in terms of antioxidant, antitumor, anti-inflammatory and antiviral properties, the role of these molecules in plants remains incompletely elucidated; a potential role in stress [...] Read more.

Lignans, phenolic plant secondary metabolites, are derived from the phenylpropanoid biosynthetic pathway. Although, being investigated for their health benefits in terms of antioxidant, antitumor, anti-inflammatory and antiviral properties, the role of these molecules in plants remains incompletely elucidated; a potential role in stress response mechanisms has been, however, proposed. In this study, a non-targeted metabolomic analysis of the roots, stems, and leaves of wild-type and PLR1-RNAi transgenic flax, devoid of (+) secoisolariciresinol diglucoside ((+) SDG)—the main flaxseed lignan, was performed using ¹H-NMR and LC-MS, in order to obtain further insight into the involvement of lignan in the response of plant to osmotic stress. Results showed that wild-type and lignan-deficient flax plants have different metabolic responses after being exposed to osmotic stress conditions, but they both showed the capacity to induce an adaptive response to osmotic stress. These findings suggest the indirect involvement of lignans in osmotic stress response. Full article

(This article belongs to the Special Issue Theme Issue Honoring Professor Robert Verpoorte’s 75th Birthday: Past, Current and Future of Natural Products Research)

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39 pages, 9029 KiB

Open AccessArticle

In Silico Studies of Lamiaceae Diterpenes with Bioinsecticide Potential against Aphis gossypii and Drosophila melanogaster

by Gabriela Cristina Soares Rodrigues, Mayara dos Santos Maia, Andreza Barbosa Silva Cavalcanti, Natália Ferreira de Sousa, Marcus Tullius Scotti and Luciana Scotti

Molecules 2021, 26(3), 766; https://doi.org/10.3390/molecules26030766 - 2 Feb 2021

Cited by 9 | Viewed by 4397

Abstract

Background: The growing demand for agricultural products has led to the misuse/overuse of insecticides; resulting in the use of higher concentrations and the need for ever more toxic products. Ecologically, bioinsecticides are considered better and safer than synthetic insecticides; they must be toxic [...] Read more.

Background: The growing demand for agricultural products has led to the misuse/overuse of insecticides; resulting in the use of higher concentrations and the need for ever more toxic products. Ecologically, bioinsecticides are considered better and safer than synthetic insecticides; they must be toxic to the target organism, yet with low or no toxicity to non-target organisms. Many plant extracts have seen their high insecticide potential confirmed under laboratory conditions, and in the search for plant compounds with bioinsecticidal activity, the Lamiaceae family has yielded satisfactory results. Objective: The aim of our study was to develop computer-assisted predictions for compounds with known insecticidal activity against Aphis gossypii and Drosophila melanogaster. Results and conclusion: Structure analysis revealed ent-kaurane, kaurene, and clerodane diterpenes as the most active, showing excellent results. We also found that the interactions formed by these compounds were more stable, or presented similar stability to the commercialized insecticides tested. Overall, we concluded that the compounds bistenuifolin L (1836) and bistenuifolin K (1931), were potentially active against A. gossypii enzymes; and salvisplendin C (1086) and salvixalapadiene (1195), are potentially active against D. melanogaster. We observed and highlight that the diterpenes bistenuifolin L (1836), bistenuifolin K (1931), salvisplendin C (1086), and salvixalapadiene (1195), present a high probability of activity and low toxicity against the species studied. Full article

(This article belongs to the Special Issue QSAR and QSPR: Recent Developments and Applications, 2nd Edition)

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56 pages, 10900 KiB

Open AccessReview

The Chemical Synthesis of the Crinine and Haemanthamine Alkaloids: Biologically Active and Enantiomerically-Related Systems that Serve as Vehicles for Showcasing New Methodologies for Molecular Assembly

by Nan Hu, Lorenzo V. White, Ping Lan and Martin G. Banwell

Molecules 2021, 26(3), 765; https://doi.org/10.3390/molecules26030765 - 2 Feb 2021

Cited by 8 | Viewed by 4910

Abstract

The title alkaloids, often referred to collectively as crinines, are a prominent group of structurally distinct natural products with additional members being reported on a regular basis. As such, and because of their often notable biological properties, they have attracted attention as synthetic [...] Read more.

The title alkaloids, often referred to collectively as crinines, are a prominent group of structurally distinct natural products with additional members being reported on a regular basis. As such, and because of their often notable biological properties, they have attracted attention as synthetic targets since the mid-1950s. Such efforts continue unabated and more recent studies on these alkaloids have focused on using them as vehicles for showcasing the utility of new synthetic methods. This review provides a comprehensive survey of the nearly seventy-year history of these synthetic endeavors. Full article

(This article belongs to the Special Issue Total Synthesis of Natural Products)

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12 pages, 2256 KiB

Open AccessCommunication

Microfluidic Preparation of ⁸⁹Zr-Radiolabelled Proteins by Flow Photochemistry

by Daniel F. Earley, Amaury Guillou, Dion van der Born, Alex J. Poot and Jason P. Holland

Molecules 2021, 26(3), 764; https://doi.org/10.3390/molecules26030764 - 2 Feb 2021

Cited by 7 | Viewed by 3612

Abstract

⁸⁹Zr-radiolabelled proteins functionalised with desferrioxamine B are a cornerstone of diagnostic positron emission tomography. In the clinical setting, ⁸⁹Zr-labelled proteins are produced manually. Here, we explore the potential of using a microfluidic photochemical flow reactor to prepare ⁸⁹Zr-radiolabelled proteins. The [...] Read more.

⁸⁹Zr-radiolabelled proteins functionalised with desferrioxamine B are a cornerstone of diagnostic positron emission tomography. In the clinical setting, ⁸⁹Zr-labelled proteins are produced manually. Here, we explore the potential of using a microfluidic photochemical flow reactor to prepare ⁸⁹Zr-radiolabelled proteins. The light-induced functionalisation and ⁸⁹Zr-radiolabelling of human serum albumin ([⁸⁹Zr]ZrDFO-PEG₃-Et-azepin-HSA) was achieved by flow photochemistry with a decay-corrected radiochemical yield (RCY) of 31.2 ± 1.3% (n = 3) and radiochemical purity >90%. In comparison, a manual batch photoreactor synthesis produced the same radiotracer in a decay-corrected RCY of 59.6 ± 3.6% (n = 3) with an equivalent RCP > 90%. The results indicate that photoradiolabelling in flow is a feasible platform for the automated production of protein-based ⁸⁹Zr-radiotracers, but further refinement of the apparatus and optimisation of the method are required before the flow process is competitive with manual reactions. Full article

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

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17 pages, 2588 KiB

Open AccessFeature PaperArticle

Sulfonate-Conjugated Polyelectrolytes as Anode Interfacial Layers in Inverted Organic Solar Cells

by Elisa Lassi, Benedetta Maria Squeo, Roberto Sorrentino, Guido Scavia, Simona Mrakic-Sposta, Maristella Gussoni, Barbara Vercelli, Francesco Galeotti, Mariacecilia Pasini and Silvia Luzzati

Molecules 2021, 26(3), 763; https://doi.org/10.3390/molecules26030763 - 2 Feb 2021

Cited by 7 | Viewed by 3224

Abstract

Conjugated polymers with ionic pendant groups (CPEs) are receiving increasing attention as solution-processed interfacial materials for organic solar cells (OSCs). Various anionic CPEs have been successfully used, on top of ITO (Indium Tin Oxide) electrodes, as solution-processed anode interlayers (AILs) for conventional devices [...] Read more.

Conjugated polymers with ionic pendant groups (CPEs) are receiving increasing attention as solution-processed interfacial materials for organic solar cells (OSCs). Various anionic CPEs have been successfully used, on top of ITO (Indium Tin Oxide) electrodes, as solution-processed anode interlayers (AILs) for conventional devices with direct geometry. However, the development of CPE AILs for OSC devices with inverted geometry is an important topic that still needs to be addressed. Here, we have designed three anionic CPEs bearing alkyl-potassium-sulfonate side chains. Their functional behavior as anode interlayers has been investigated in P3HT:PC₆₁BM (poly(3-hexylthiophene): [6,6]-phenyl C61 butyric acid methyl ester) devices with an inverted geometry, using a hole collecting silver electrode evaporated on top. Our results reveal that to obtain effective anode modification, the CPEs’ conjugated backbone has to be tailored to grant self-doping and to have a good energy-level match with the photoactive layer. Furthermore, the sulfonate moieties not only ensure the solubility in polar orthogonal solvents, induce self-doping via a right choice of the conjugated backbone, but also play a role in the gaining of hole selectivity of the top silver electrode. Full article

(This article belongs to the Special Issue Organic and Hybrid Materials for Photovoltaic and Photonic Applications)

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13 pages, 9943 KiB

Open AccessArticle

Effective and Sustained Control of Soil-Borne Plant Diseases by Biodegradable Polyhydroxybutyrate Mulch Films Embedded with Fungicide of Prothioconazole

by Ge Chen, Lidong Cao, Chong Cao, Pengyue Zhao, Fengmin Li, Bo Xu and Qiliang Huang

Molecules 2021, 26(3), 762; https://doi.org/10.3390/molecules26030762 - 2 Feb 2021

Cited by 23 | Viewed by 4736

Abstract

Soil-borne diseases and plant rhizosphere nematode have caused many crop yield losses. Increased environmental awareness is leading to more restrictions on the use of certain fumigants and root irrigation methods due to their impact on human health and soil system. Therefore, it is [...] Read more.

Soil-borne diseases and plant rhizosphere nematode have caused many crop yield losses. Increased environmental awareness is leading to more restrictions on the use of certain fumigants and root irrigation methods due to their impact on human health and soil system. Therefore, it is necessary to find alternative treatments to maintain crop economic yields and environmental sustainability. In the present work, biodegradable antifungal mulches were prepared by blending poly(3-hydroxybutyrate-co-4-hydroxybutyrate) (PHB) with fungicide of prothioconazole (PRO), which were used for effective and sustained control of soil-borne plant diseases. To reveal the application prospect of the PHB/PRO composite films in the management of soilborne plant diseases, some physical and biological properties were evaluated. The proper mulch film of PHB/PRO was assessed based on its mechanical and optical properties, while water solubility and the film micromorphology was further characterized. The release patterns of composite films under different pH levels were investigated. Moreover, the in vitro antifungal bioassay and pot experiment showed satisfactory bioactivity of the PHB/PRO films against Sclerotium rolfsii Sacc., a soil-borne disease in peanut fields. This study demonstrated that the biodegradable mulch films containing PRO fungicide are capable of inhibiting soil-borne plant pathogenic fungi effectively, and this facile but powerful strategy may find wide applicability in sustainable plant and horticulture protection. Full article

(This article belongs to the Special Issue Advanced Biodegradable Polymers)

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28 pages, 2692 KiB

Open AccessArticle

Nuclear Magnetic Resonance Metabolomics Approach for the Analysis of Major Legume Sprouts Coupled to Chemometrics

by Mohamed A. Farag, Mohamed G. Sharaf El-Din, Mohamed A. Selim, Asmaa I. Owis, Sameh F. Abouzid, Andrea Porzel, Ludger A. Wessjohann and Asmaa Otify

Molecules 2021, 26(3), 761; https://doi.org/10.3390/molecules26030761 - 2 Feb 2021

Cited by 19 | Viewed by 4411

Abstract

Legume sprouts are a fresh nutritive source of phytochemicals of increasing attention worldwide owing to their many health benefits. Nuclear magnetic resonance (NMR) was utilized for the metabolite fingerprinting of 4 major legume sprouts, belonging to family Fabaceae, to be exploited for quality [...] Read more.

Legume sprouts are a fresh nutritive source of phytochemicals of increasing attention worldwide owing to their many health benefits. Nuclear magnetic resonance (NMR) was utilized for the metabolite fingerprinting of 4 major legume sprouts, belonging to family Fabaceae, to be exploited for quality control purposes. Thirty-two metabolites were identified belonging to different classes, i.e., fatty acids, sugars, amino acids, nucleobases, organic acids, sterols, alkaloids, and isoflavonoids. Quantitative NMR was employed for assessing the major identified metabolite levels and multivariate data analysis was utilized to assess metabolome heterogeneity among sprout samples. Isoflavones were detected exclusively in Cicer sprouts, whereas Trigonella was characterized by 4-hydroxyisoleucine. Vicia sprouts were distinguished from other legume sprouts by the presence of L-Dopa versus acetate abundance in Lens. A common alkaloid in all sprouts was trigonelline, detected at 8–25 µg/mg, suggesting its potential role in legume seeds’ germination. Trigonelline was found at highest levels in Trigonella sprouts. The aromatic NMR region data (δ 11.0–5.0 ppm) provided a better classification power than the full range (δ 11.0–0.0 ppm) as sprout variations mostly originated from secondary metabolites, which can serve as chemotaxonomic markers. Full article

(This article belongs to the Special Issue Food and Drug Analysis Ⅱ)

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10 pages, 727 KiB

Open AccessOpinion

Which Traits of Humic Substances Are Investigated to Improve Their Agronomical Value?

by Heejung Jung, Sumin Kwon, Jae-Hwan Kim and Jong-Rok Jeon

Molecules 2021, 26(3), 760; https://doi.org/10.3390/molecules26030760 - 2 Feb 2021

Cited by 16 | Viewed by 3975

Abstract

Humic substances (HSs) are chromogenic organic assemblies that are widespread in the environment, including soils, oceans, rivers, and coal-related resources. HSs are known to directly and indirectly stimulate plants based on their versatile organic structures. Their beneficial activities have led to the rapid [...] Read more.

Humic substances (HSs) are chromogenic organic assemblies that are widespread in the environment, including soils, oceans, rivers, and coal-related resources. HSs are known to directly and indirectly stimulate plants based on their versatile organic structures. Their beneficial activities have led to the rapid market growth of agronomical HSs. However, there are still several technical issues and concerns to be addressed to advance sustainable agronomical practices for HSs and allow growers to use HSs reliably. First, it is necessary to elucidate the evident structure (component)–function relationship of HSs. Specifically, the core structural features of HSs corresponding to crop species, treatment method (i.e., soil, foliar, or immersion applications), and soil type-dependent plant stimulatory actions as well as specific plant responses (e.g., root genesis and stress resistance) should be detailed to identify practical crop treatment methodologies. These trials must then be accompanied by means to upgrade crop marketability to help the growers. Second, structural differences of HSs depending on extraction sources should be compared to develop quality control and assurance measures for agronomical uses of HSs. In particular, coal-related HSs obtainable in bulk amounts for large farmland applications should be structurally and functionally distinguishable from other natural HSs. The diversity of organic structures and components in coal-based HSs must thus be examined thoroughly to provide practical information to growers. Overall, there is a consensus amongst researchers that HSs have the potential to enhance soil quality and crop productivity, but appropriate research directions should be explored for growers’ needs and farmland applications. Full article

(This article belongs to the Special Issue Natural Organic Matter as Plant Growth Promoter: Research Activities and Technology Applications)

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12 pages, 1254 KiB

Open AccessArticle

Phytochemical Investigation and Antioxidant Activity of Globularia alypum L.

by Fadoua Asraoui, Ayoub Kounnoun, Hafssa El Cadi, Francesco Cacciola, Yassine Oulad El Majdoub, Filippo Alibrando, Filippo Mandolfino, Paola Dugo, Luigi Mondello and Adnane Louajri

Molecules 2021, 26(3), 759; https://doi.org/10.3390/molecules26030759 - 2 Feb 2021

Cited by 36 | Viewed by 6091

Abstract

The Moroccan flora is rich in medicinal plants that are commonly used in folk medicine for the treatment of various diseases. The present study was designed to investigate the total phenolic and flavonoid contents, as well as the antioxidant properties of leaves extracts [...] Read more.

The Moroccan flora is rich in medicinal plants that are commonly used in folk medicine for the treatment of various diseases. The present study was designed to investigate the total phenolic and flavonoid contents, as well as the antioxidant properties of leaves extracts from Globularia alypum L. colected from the Taza region in northeast Morocco. Additionally, the individual phenolics and volatiles of the extracts were also evaluated. The organic extracts of this plant were obtained by Soxhlet extraction using two different solvents, namely ethyl acetate and chloroform. The antioxidant capacity of leaves extracts was measured using DPPH, ABTS and FRAP assays; the phenolic profile was determined by HPLC-DAD/ESI-MS analysis, whereas the volatile composition was elucidated by GC-MS. The ethyl acetate extract analysis showed a total of 20 phenolic compounds and the determination of phenolic contents showed a significant value of 56.5 ± 0.61 µg GAE/mg of extract in comparison with the chloroform extract (18.9 ± 0.48 µg GAE/mg of extract). Also, the determination of the flavonoid contents revealed that the ethyl acetate extract contained the highest value (30.2 ± 0.55 µg CE/mg of extract) in comparison with the chloroform extract (18.0 ± 0.36 µg CE/mg of extract). Concerning the antioxidant properties, interesting values were attained for the ethyl acetate extract which exhibited higher antioxidant activity, namely IC₅₀ = 12.3 ± 3.83 µg/mL and IC50 = 37.0 ± 2.45 µg/mL for the DPPH and ABTS assays, respectively, whereas a value of 531.1 ± 17.08 (mg AAE/g DW) was obtained for the FRAP assay. Concerning the volatile profile, a total of 73 compounds were positively detected and among them n-hexadecanoic acid (13.5%) was the most abundant one. The results achieved confirm the important role of this plant as a source of natural antioxidants. Full article

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

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13 pages, 11262 KiB

Open AccessArticle

Ionogels Obtained by Thiol-Ene Photopolymerization—Physicochemical Characterization and Application in Electrochemical Capacitors

by Agnieszka Marcinkowska, Piotr Gajewski, Katarzyna Szcześniak, Mariola Sadej and Aneta Lewandowska

Molecules 2021, 26(3), 758; https://doi.org/10.3390/molecules26030758 - 2 Feb 2021

Cited by 6 | Viewed by 3181

Abstract

Flexible ionogels with good mechanical properties were obtained in situ by thiol-ene photopolymerization of trimethylolpropane tris(3-mercaptopropionate) (TMPTP) and 1,3,5-triallyl-1,3,5-triazine-2,4,6(1H,3H,5H)-trione (TATT) (with C=C: SH ratio 1:1) in four imidazolium ionic liquids (1-ethyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide—EMImNTf₂, 1-ethyl-3-methylimidazolium trifluoromethanesulfonate-EMImOTf, 1-butyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide-BMImNTf₂, and 1-butyl-3-methylimidazolium trifluoromethanesulfonate—BMImOTf) [...] Read more.

Flexible ionogels with good mechanical properties were obtained in situ by thiol-ene photopolymerization of trimethylolpropane tris(3-mercaptopropionate) (TMPTP) and 1,3,5-triallyl-1,3,5-triazine-2,4,6(1H,3H,5H)-trione (TATT) (with C=C: SH ratio 1:1) in four imidazolium ionic liquids (1-ethyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide—EMImNTf₂, 1-ethyl-3-methylimidazolium trifluoromethanesulfonate-EMImOTf, 1-butyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide-BMImNTf₂, and 1-butyl-3-methylimidazolium trifluoromethanesulfonate—BMImOTf) used in the range 50 to 70 wt.%. The mechanical and electrochemical properties of obtained ionogels were examined. Ionogels with ionic liquids (ILs) with NTf₂⁻ anion are more puncture resistant than with OTf⁻ anion. Moreover, ionogels with the NTF₂⁻ anion have better electrochemical properties than those with the OTf⁻ anion. Although it should be noted that ionogels with the EMIm⁺ cation have a higher conductivity than the BMIm⁺. This is connected with intermolecular interactions between polymer matrix and IL related to the polarity of IL described by the Kamlet-Taft parameters. These parameters influence the morphology of the polymer matrix (as shown by the SEM micrograph), which is formed by interconnected polymer spheres. Full article

(This article belongs to the Special Issue Materials for Emerging Electrochemical Devices)

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9 pages, 4548 KiB

Open AccessArticle

[Cr^III₈Ni^II₆]ⁿ⁺ Heterometallic Coordination Cubes

by Helen M. O’Connor, Sergio Sanz, Aaron J. Scott, Mateusz B. Pitak, Wim T. Klooster, Simon J. Coles, Nicholas F. Chilton, Eric J. L. McInnes, Paul J. Lusby, Høgni Weihe, Stergios Piligkos and Euan K. Brechin

Molecules 2021, 26(3), 757; https://doi.org/10.3390/molecules26030757 - 2 Feb 2021

Cited by 4 | Viewed by 3451

Abstract

Three new heterometallic [Cr^III₈Ni^II₆] coordination cubes of formulae [Cr^III₈Ni^II₆L₂₄(H₂O)₁₂](NO₃)₁₂ (1), [Cr^III₈Ni^II₆L₂₄(MeCN)₇ [...] Read more.

Three new heterometallic [Cr^III₈Ni^II₆] coordination cubes of formulae [Cr^III₈Ni^II₆L₂₄(H₂O)₁₂](NO₃)₁₂ (1), [Cr^III₈Ni^II₆L₂₄(MeCN)₇(H₂O)₅](ClO₄)₁₂ (2), and [Cr^III₈Ni^II₆L₂₄Cl₁₂] (3) (where HL = 1-(4-pyridyl)butane-1,3-dione), were synthesised using the paramagnetic metalloligand [Cr^IIIL₃] and the corresponding Ni^II salt. The magnetic skeleton of each capsule describes a face-centred cube in which the eight Cr^III and six Ni^II ions occupy the eight vertices and six faces of the structure, respectively. Direct current magnetic susceptibility measurements on (1) reveal weak ferromagnetic interactions between the Cr^III and Ni^II ions, with J_Cr-Ni = + 0.045 cm⁻¹. EPR spectra are consistent with weak exchange, being dominated by the zero-field splitting of the Cr^III ions. Excluding wheel-like structures, examples of large heterometallic clusters containing both Cr^III and Ni^II ions are rather rare, and we demonstrate that the use of metalloligands with predictable bonding modes allows for a modular approach to building families of related polymetallic complexes. Compounds (1)–(3) join the previously published, structurally related family of [M^III₈M^II₆] cubes, where M^III = Cr, Fe and M^II = Cu, Co, Mn, Pd. Full article

(This article belongs to the Special Issue Advances in Chemical Crystallography: A Themed Issue Honoring Professor Alexandra M. Z. Slawin on the Occasion of Her 60th Birthday)

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10 pages, 1233 KiB

Open AccessArticle

H₂O-Induced Hydrophobic Interactions in MS-Guided Counter-Current Chromatography Separation of Anti-Cancer Mollugin from Rubia cordifolia

by Liping Zeng, Tianyi Xu, Jie Meng, Dingfang Wu and Shihua Wu

Molecules 2021, 26(3), 751; https://doi.org/10.3390/molecules26030751 - 2 Feb 2021

Cited by 3 | Viewed by 2613

Abstract

Counter-current chromatography (CCC) is a unique liquid–liquid partition chromatography and largely relies on the partition interactions of solutes and solvents in two-phase solvents. Usually, the two-phase solvents used in CCC include a lipophilic organic phase and a hydrophilic aqueous phase. Although a large [...] Read more.

Counter-current chromatography (CCC) is a unique liquid–liquid partition chromatography and largely relies on the partition interactions of solutes and solvents in two-phase solvents. Usually, the two-phase solvents used in CCC include a lipophilic organic phase and a hydrophilic aqueous phase. Although a large number of partition interactions have been found and used in the CCC separations, there are few studies that address the role of water on solvents and solutes in the two-phase partition. In this study, we presented a new insight that H₂O (water) might be an efficient and sensible hydrophobic agent in the n-hexane-methanol-based two-phase partition and CCC separation of lipophilic compounds, i.e., anti-cancer component mollugin from Rubia cordifolia. Although the n-hexane-methanol-based four components solvent systems of n-hexane-ethyl acetate-methanol-water (HEMWat) is one of the most popular CCC solvent systems and widely used for natural products isolation, this is an interesting trial to investigate the water roles in the two-phase solutions. In addition, as an example, the bioactive component mollugin was targeted, separated, and purified by MS-guided CCC with hexane-methanol and minor water as a hydrophobic agent. It might be useful for isolation and purification of lipophilic mollugin and other bioactive compounds complex natural products and traditional Chinese medicines. Full article

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12 pages, 2945 KiB

Open AccessArticle

Chemical Constituents from Roots of Sophora davidii (Franch.) Skeels and Their Glucose Transporter 4 Translocation Activities

by Kangdi Li, Yuanren Ma, Tongxi Zhou, Xinzhou Yang and Ho-Young Choi

Molecules 2021, 26(3), 756; https://doi.org/10.3390/molecules26030756 - 1 Feb 2021

Cited by 7 | Viewed by 2888

Abstract

Sophora davidii (Franch.) Skeels is a multi-purpose traditional medicine that has long been used for the treatment of various diseases. To discover the potential bioactive composition of S. davidii, a chemical investigation was thus performed. In this research, two new stilbene oligomers, [...] Read more.

Sophora davidii (Franch.) Skeels is a multi-purpose traditional medicine that has long been used for the treatment of various diseases. To discover the potential bioactive composition of S. davidii, a chemical investigation was thus performed. In this research, two new stilbene oligomers, Davidiol E–F (1–2), one new 4-aryl-substituted isoflavan Davidinin A (3), and one new 2-arylbenzofuran dimer, Shandougenine C (4), as well as six known compounds (5–10) were obtained from the ethyl acetate fraction of Sophora davidii (Franch.) Skeels. The structures of new compounds were established by extensive 1D and 2D nuclear magnetic resonance (NMR) spectra with mass spectroscopy data. The absolute configuration of 1–3 was assigned by comparing its experimental and calculated electronic circular dichroism (ECD) spectra. Compounds 1–10 promoted glucose transporter 4 (GLUT-4) translocations by the range of 1.28–2.60 folds, respectively. Compound 9 showed the most potent glucose transporter 4 translocations with 1.60 fold enhancement. The result attained in this study indicated that the separation and characterization of these compounds plays an important role in the research and development of new anti-diabetic drugs and pharmaceutical industry. Full article

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10 pages, 1383 KiB

Open AccessFeature PaperArticle

Jean-Louis Luche and the Interpretation of Sonochemical Reaction Mechanisms

by Mircea Vinatoru and Timothy J. Mason

Molecules 2021, 26(3), 755; https://doi.org/10.3390/molecules26030755 - 1 Feb 2021

Cited by 12 | Viewed by 3689

Abstract

Sonochemistry can be broadly defined as the science of chemical and physical transformations produced under the influence of sound. The use of sound energy is rather a young branch of chemistry and does not have the clear definitive rules of other, more established, [...] Read more.

Sonochemistry can be broadly defined as the science of chemical and physical transformations produced under the influence of sound. The use of sound energy is rather a young branch of chemistry and does not have the clear definitive rules of other, more established, divisions such as those in cycloaddition reactions or photochemistry. Nevertheless, there are a few guidelines which can help to predict what is going to happen when a reaction mixture is submitted to ultrasonic irradiation. Jean-Louis Luche, formulated some ideas of the mechanistic pathways involved in sonochemistry more than 30 years ago. He introduced the idea of “true” and “false” sonochemical reactions both of which are the result of acoustic cavitation. The difference was that the former involved a free radical component whereas only mechanical effects played a role the latter. The authors of this paper were scientific collaborators and friends of Jean-Louis Luche during those early years and had the chance to discuss and work with him on the mechanisms of sonochemistry. In this paper we will review the original rules (laws) as predicted by Jean-Louis Luche and how they have been further developed and extended in recent years. Full article

(This article belongs to the Special Issue Sonochemistry: Understanding of Ultrasonic-Based Phenomena and Innovative Applications in Chemistry: A Commemorative Issue in Honor of Dr. Jean-Louis Luche)

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21 pages, 2564 KiB

Open AccessArticle

In Vitro and In Vivo Antitumor Activity of Indolo[2,3-b] Quinolines, Natural Product Analogs from Neocryptolepine Alkaloid

by Najla Altwaijry, Samah El-Ghlban, Ibrahim E.-T. El Sayed, Mohamed El-Bahnsawye, Asmaa I. Bayomi, Rehab M. Samaka, Elkhabiry Shaban, Elshaymaa I. Elmongy, Thanaa A. El-Masry, Hytham M. A. Ahmed and Nashwah G. M. Attallah

Molecules 2021, 26(3), 754; https://doi.org/10.3390/molecules26030754 - 1 Feb 2021

Cited by 21 | Viewed by 4671

Abstract

Neocryptolepine (5-methyl-5H-indolo[2,3-b] quinoline) analogs were synthesized and evaluated in vitro and in vivo for their effect versus Ehrlich ascites carcinoma (EAC). The analogs showed stronger cytotoxic activity against EAC cells than the reference drug. The in vivo evaluation of the target compounds against [...] Read more.

Neocryptolepine (5-methyl-5H-indolo[2,3-b] quinoline) analogs were synthesized and evaluated in vitro and in vivo for their effect versus Ehrlich ascites carcinoma (EAC). The analogs showed stronger cytotoxic activity against EAC cells than the reference drug. The in vivo evaluation of the target compounds against EAC-induced solid tumor in the female albino Swiss mice revealed a remarkable decrease in the tumor volume (TV) and hepatic lipid peroxidation. A noticeable increase of both superoxide dismutase (SOD) and catalase (CAT) levels was reported (p < 0.001), which set-forth proof of their antioxidant effect. In addition, the in vitro antioxidant activity of the neocryptolepine analogs was screened out using the DPPH method and showed promising activities activity. The histopathological investigations affirmed that the tested analogs have a remarkable curative effect on solid tumors with minimal side-effect on the liver. The study also includes illustrated mechanism of the antitumor activity at the cell level by flow cytometry. The cell cycle analysis showed that the neocryptolepine analogs extensively increase the aggregation of tumor cells in three phases of the cell cycle (G0/G1, S and G2/M) with the emergence of a hypo-diploid DNA content peak (sub-G1) in the cell cycle experiments, which is a clear-cut for the apoptotic cell population. Furthermore, the immunological study manifested a significant elevation in splenic lymphocyte count (p < 0.001) with the elevation of the responsiveness of lymphocytes to phytohemagglutinin (PHA). These results indicate that these naturally-based neocryptolepine alkaloids exhibit marked antitumor activity in vivo and represent an important lead in the development of natural-based anticancer drugs. Full article

(This article belongs to the Collection Novel Approache of Anticancer Therapy)

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23 pages, 2623 KiB

Open AccessReview

Bioethanol Production by Enzymatic Hydrolysis from Different Lignocellulosic Sources

by Katja Vasić, Željko Knez and Maja Leitgeb

Molecules 2021, 26(3), 753; https://doi.org/10.3390/molecules26030753 - 1 Feb 2021

Cited by 167 | Viewed by 17585

Abstract

As the need for non-renewable sources such as fossil fuels has increased during the last few decades, the search for sustainable and renewable alternative sources has gained growing interest. Enzymatic hydrolysis in bioethanol production presents an important step, where sugars that are fermented [...] Read more.

As the need for non-renewable sources such as fossil fuels has increased during the last few decades, the search for sustainable and renewable alternative sources has gained growing interest. Enzymatic hydrolysis in bioethanol production presents an important step, where sugars that are fermented are obtained in the final fermentation process. In the process of enzymatic hydrolysis, more and more new effective enzymes are being researched to ensure a more cost-effective process. There are many different enzyme strategies implemented in hydrolysis protocols, where different lignocellulosic biomass, such as wood feedstocks, different agricultural wastes, and marine algae are being used as substrates for an efficient bioethanol production. This review investigates the very recent enzymatic hydrolysis pathways in bioethanol production from lignocellulosic biomass. Full article

(This article belongs to the Special Issue Lignocellulosic Biomass to Biofuels and Biochemicals)

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14 pages, 1396 KiB

Open AccessReview

Potential of Sulforaphane as a Natural Immune System Enhancer: A Review

by Andrea Mahn and Antonio Castillo

Molecules 2021, 26(3), 752; https://doi.org/10.3390/molecules26030752 - 1 Feb 2021

Cited by 69 | Viewed by 10739

Abstract

Brassicaceae are an outstanding source of bioactive compounds such as ascorbic acid, polyphenols, essential minerals, isothiocyanates and their precursors, glucosinolates (GSL). Recently, GSL gained great attention because of the health promoting properties of their hydrolysis products: isothiocyanates. Among them, sulforaphane (SFN) became the [...] Read more.

Brassicaceae are an outstanding source of bioactive compounds such as ascorbic acid, polyphenols, essential minerals, isothiocyanates and their precursors, glucosinolates (GSL). Recently, GSL gained great attention because of the health promoting properties of their hydrolysis products: isothiocyanates. Among them, sulforaphane (SFN) became the most attractive one owing to its remarkable health-promoting properties. SFN may prevent different types of cancer and has the ability to improve hypertensive states, to prevent type 2 diabetes–induced cardiomyopathy, and to protect against gastric ulcer. SFN may also help in schizophrenia treatment, and recently it was proposed that SFN has potential to help those who struggle with obesity. The mechanism underlying the health-promoting effect of SFN relates to its indirect action at cellular level by inducing antioxidant and Phase II detoxifying enzymes through the activation of transcription nuclear factor (erythroid-derived 2)-like (Nrf2). The effect of SFN on immune response is generating scientific interest, because of its bioavailability, which is much higher than other phytochemicals, and its capacity to induce Nrf2 target genes. Clinical trials suggest that sulforaphane produces favorable results in cases where pharmaceutical products fail. This article provides a revision about the relationship between sulforaphane and immune response in different diseases. Special attention is given to clinical trials related with immune system disorders. Full article

(This article belongs to the Special Issue Bioactive Compounds on Health and Disease)

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19 pages, 2588 KiB

Open AccessReview

Advances in Cryochemistry: Mechanisms, Reactions and Applications

by Lu-Yan An, Zhen Dai, Bin Di and Li-Li Xu

Molecules 2021, 26(3), 750; https://doi.org/10.3390/molecules26030750 - 1 Feb 2021

Cited by 8 | Viewed by 5059

Abstract

It is counterintuitive that chemical reactions can be accelerated by freezing, but this amazing phenomenon was discovered as early as the 1960s. In frozen systems, the increase in reaction rate is caused by various mechanisms and the freeze concentration effect is the main [...] Read more.

It is counterintuitive that chemical reactions can be accelerated by freezing, but this amazing phenomenon was discovered as early as the 1960s. In frozen systems, the increase in reaction rate is caused by various mechanisms and the freeze concentration effect is the main reason for the observed acceleration. Some accelerated reactions have great application value in the chemistry synthesis and environmental fields; at the same time, certain reactions accelerated at low temperature during the storage of food, medicine, and biological products should cause concern. The study of reactions accelerated by freezing will overturn common sense and provide a new strategy for researchers in the chemistry field. In this review, we mainly introduce various mechanisms for accelerating reactions induced by freezing and summarize a variety of accelerated cryochemical reactions and their applications. Full article

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16 pages, 932 KiB

Open AccessReview

A Review of the Discriminant Analysis Methods for Food Quality Based on Near-Infrared Spectroscopy and Pattern Recognition

by Jian Zeng, Yuan Guo, Yanqing Han, Zhanming Li, Zhixin Yang, Qinqin Chai, Wu Wang, Yuyu Zhang and Caili Fu

Molecules 2021, 26(3), 749; https://doi.org/10.3390/molecules26030749 - 1 Feb 2021

Cited by 49 | Viewed by 5372

Abstract

Near-infrared spectroscopy (NIRS) combined with pattern recognition technique has become an important type of non-destructive discriminant method. This review first introduces the basic structure of the qualitative analysis process based on near-infrared spectroscopy. Then, the main pretreatment methods of NIRS data processing are [...] Read more.

Near-infrared spectroscopy (NIRS) combined with pattern recognition technique has become an important type of non-destructive discriminant method. This review first introduces the basic structure of the qualitative analysis process based on near-infrared spectroscopy. Then, the main pretreatment methods of NIRS data processing are investigated. Principles and recent developments of traditional pattern recognition methods based on NIRS are introduced, including some shallow learning machines and clustering analysis methods. Moreover, the newly developed deep learning methods and their applications of food quality analysis are surveyed, including convolutional neural network (CNN), one-dimensional CNN, and two-dimensional CNN. Finally, several applications of these pattern recognition techniques based on NIRS are compared. The deficiencies of the existing pattern recognition methods and future research directions are also reviewed. Full article

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32 pages, 3050 KiB

Open AccessReview

Wearable Biosensors: An Alternative and Practical Approach in Healthcare and Disease Monitoring

by Atul Sharma, Mihaela Badea, Swapnil Tiwari and Jean Louis Marty

Molecules 2021, 26(3), 748; https://doi.org/10.3390/molecules26030748 - 1 Feb 2021

Cited by 168 | Viewed by 18654

Abstract

With the increasing prevalence of growing population, aging and chronic diseases continuously rising healthcare costs, the healthcare system is undergoing a vital transformation from the traditional hospital-centered system to an individual-centered system. Since the 20th century, wearable sensors are becoming widespread in healthcare [...] Read more.

With the increasing prevalence of growing population, aging and chronic diseases continuously rising healthcare costs, the healthcare system is undergoing a vital transformation from the traditional hospital-centered system to an individual-centered system. Since the 20th century, wearable sensors are becoming widespread in healthcare and biomedical monitoring systems, empowering continuous measurement of critical biomarkers for monitoring of the diseased condition and health, medical diagnostics and evaluation in biological fluids like saliva, blood, and sweat. Over the past few decades, the developments have been focused on electrochemical and optical biosensors, along with advances with the non-invasive monitoring of biomarkers, bacteria and hormones, etc. Wearable devices have evolved gradually with a mix of multiplexed biosensing, microfluidic sampling and transport systems integrated with flexible materials and body attachments for improved wearability and simplicity. These wearables hold promise and are capable of a higher understanding of the correlations between analyte concentrations within the blood or non-invasive biofluids and feedback to the patient, which is significantly important in timely diagnosis, treatment, and control of medical conditions. However, cohort validation studies and performance evaluation of wearable biosensors are needed to underpin their clinical acceptance. In the present review, we discuss the importance, features, types of wearables, challenges and applications of wearable devices for biological fluids for the prevention of diseased conditions and real-time monitoring of human health. Herein, we summarize the various wearable devices that are developed for healthcare monitoring and their future potential has been discussed in detail. Full article

(This article belongs to the Special Issue Smart Non-invasive Sensor Technologies for Healthcare and Biomedical Applications)

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16 pages, 1934 KiB

Open AccessArticle

NMR Structure Determinations of Small Proteins Using only One Fractionally 20% ¹³C- and Uniformly 100% ¹⁵N-Labeled Sample

by Harri A. Heikkinen, Sofia M. Backlund and Hideo Iwaï

Molecules 2021, 26(3), 747; https://doi.org/10.3390/molecules26030747 - 1 Feb 2021

Cited by 6 | Viewed by 5019

Abstract

Uniformly ¹³C- and ¹⁵N-labeled samples ensure fast and reliable nuclear magnetic resonance (NMR) assignments of proteins and are commonly used for structure elucidation by NMR. However, the preparation of uniformly labeled samples is a labor-intensive and expensive step. Reducing the portion [...] Read more.

Uniformly ¹³C- and ¹⁵N-labeled samples ensure fast and reliable nuclear magnetic resonance (NMR) assignments of proteins and are commonly used for structure elucidation by NMR. However, the preparation of uniformly labeled samples is a labor-intensive and expensive step. Reducing the portion of ¹³C-labeled glucose by a factor of five using a fractional 20% ¹³C- and 100% ¹⁵N-labeling scheme could lower the total chemical costs, yet retaining sufficient structural information of uniformly [¹³C, ¹⁵N]-labeled sample as a result of the improved sensitivity of NMR instruments. Moreover, fractional ¹³C-labeling can facilitate reliable resonance assignments of sidechains because of the biosynthetic pathways of each amino-acid. Preparation of only one [20% ¹³C, 100% ¹⁵N]-labeled sample for small proteins (<15 kDa) could also eliminate redundant sample preparations of 100% ¹⁵N-labeled and uniformly 100% [¹³C, ¹⁵N]-labeled samples of proteins. We determined the NMR structures of a small alpha-helical protein, the C domain of IgG-binding protein A from Staphylococcus aureus (SpaC), and a small beta-sheet protein, CBM64 module using [20% ¹³C, 100% ¹⁵N]-labeled sample and compared with the crystal structures and the NMR structures derived from the 100% [¹³C, ¹⁵N]-labeled sample. Our results suggest that one [20% ¹³C, 100% ¹⁵N]-labeled sample of small proteins could be routinely used as an alternative to conventional 100% [¹³C, ¹⁵N]-labeling for backbone resonance assignments, NMR structure determination, ¹⁵N-relaxation analysis, and ligand–protein interaction. Full article

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16 pages, 1697 KiB

Open AccessArticle

Solubility Data, Solubility Parameters and Thermodynamic Behavior of an Antiviral Drug Emtricitabine in Different Pure Solvents: Molecular Understanding of Solubility and Dissolution

by Faiyaz Shakeel, Nazrul Haq, Ibrahim Alsarra and Sultan Alshehri

Molecules 2021, 26(3), 746; https://doi.org/10.3390/molecules26030746 - 31 Jan 2021

Cited by 13 | Viewed by 3185

Abstract

The solubility values, various Hansen solubility parameters (HSPs) and thermodynamic behavior of emtricitabine (ECT) in twelve different pure solvents (PS) were estimated using various experimental as well as computational methods. Experimental solubility values (x_e) of ECT in twelve different PS [...] Read more.

The solubility values, various Hansen solubility parameters (HSPs) and thermodynamic behavior of emtricitabine (ECT) in twelve different pure solvents (PS) were estimated using various experimental as well as computational methods. Experimental solubility values (x_e) of ECT in twelve different PS were obtained at T = 298.2 K to 318.2 K and p = 0.1 MPa. The x_e values of ECT were correlated by “van’t Hoff, Apelblat and Buchowski-Ksiazaczak λh models”. Various HSPs for ECT and twelve different PS were also calculated using “HSPiP software”. The x_e values of ECT were estimated maximum in polyethylene glycol-400 (PEG-400; 1.41 × 10⁻¹), followed by ethylene glycol, Transcutol-HP, propylene glycol, methanol, water, isopropanol, ethanol, 1-butanol, dimethyl sulfoxide, 2-butanol and EA (1.28 × 10⁻³) at T = 318.2 K. “Apparent thermodynamic analysis” showed an “endothermic and entropy-driven dissolution” of ECT. Overall, PEG-400 was found as the best/ideal solvent for solubility/miscibility of ECT compared to other solvents studied. Full article

(This article belongs to the Special Issue 25th Anniversary of Molecules—Recent Advances in Molecular Liquids)

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14 pages, 2661 KiB

Open AccessArticle

Fungicidal Activity of Volatile Organic Compounds Emitted by Burkholderia gladioli Strain BBB-01

by Ying-Tong Lin, Cheng-Cheng Lee, Wei-Ming Leu, Je-Jia Wu, Yu-Cheng Huang and Menghsiao Meng

Molecules 2021, 26(3), 745; https://doi.org/10.3390/molecules26030745 - 31 Jan 2021

Cited by 21 | Viewed by 3737

Abstract

A Burkholderia gladioli strain, named BBB-01, was isolated from rice shoots based on the confrontation plate assay activity against several plant pathogenic fungi. The genome of this bacterial strain consists of two circular chromosomes and one plasmid with 8,201,484 base pairs in total. [...] Read more.

A Burkholderia gladioli strain, named BBB-01, was isolated from rice shoots based on the confrontation plate assay activity against several plant pathogenic fungi. The genome of this bacterial strain consists of two circular chromosomes and one plasmid with 8,201,484 base pairs in total. Pangenome analysis of 23 B. gladioli strains suggests that B. gladioli BBB-01 has the closest evolutionary relationship to B. gladioli pv. gladioli and B. gladioli pv. agaricicola. B. gladioli BBB-01 emitted dimethyl disulfide and 2,5-dimethylfuran when it was cultivated in lysogeny broth and potato dextrose broth, respectively. Dimethyl disulfide is a well-known pesticide, while the bioactivity of 2,5-dimethylfuran has not been reported. In this study, the inhibition activity of the vapor of these two compounds was examined against phytopathogenic fungi, including Magnaporthe oryzae, Gibberella fujikuroi, Sarocladium oryzae, Phellinus noxius and Colletotrichumfructicola, and human pathogen Candida albicans. In general, 2,5-dimethylfuran is more potent than dimethyl disulfide in suppressing the growth of the tested fungi, suggesting that 2,5-dimethylfuran is a potential fumigant to control plant fungal disease. Full article

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16 pages, 2889 KiB

Open AccessArticle

Experimental and Computational Evaluation of Chloranilic Acid as an Universal Chromogenic Reagent for the Development of a Novel 96-Microwell Spectrophotometric Assay for Tyrosine Kinase Inhibitors

by Ibrahim A. Darwish, Hany W. Darwish, Nasr Y. Khalil and Ahmed Y. A. Sayed

Molecules 2021, 26(3), 744; https://doi.org/10.3390/molecules26030744 - 31 Jan 2021

Cited by 7 | Viewed by 2983

Abstract

The tyrosine kinase inhibitors (TKIs) are chemotherapeutic drugs used for the targeted therapy of various types of cancer. This work discusses the experimental and computational evaluation of chloranilic acid (CLA) as a universal chromogenic reagent for developing a novel 96-microwell spectrophotometric assay (MW-SPA) [...] Read more.

The tyrosine kinase inhibitors (TKIs) are chemotherapeutic drugs used for the targeted therapy of various types of cancer. This work discusses the experimental and computational evaluation of chloranilic acid (CLA) as a universal chromogenic reagent for developing a novel 96-microwell spectrophotometric assay (MW-SPA) for TKIs. The reaction resulted in an instantaneous formation of intensely purple colored products with TKIs. Spectrophotometric results confirmed that the reactions proceeded via the formation of charge-transfer complexes (CTCs). The physical parameters were determined for the CTCs of all TKIs. Computational calculations and molecular modelling for the CTCs were conducted, and the site(s) of interaction on each TKI molecule were determined. Under the optimized conditions, Beer’s law correlating the absorbances of the CTCs with the concentrations of TKIs were obeyed in the range of 10–500 µg/well with good correlation coefficients (0.9993–0.9998). The proposed MW-SPA fully validated and successfully applied for the determination of all TKIs in their bulk forms and pharmaceutical formulations (tablets). The proposed MW-SPA is the first assay that can analyze all the TKIs on a single assay system without modifications in the detection wavelength. The advantages of the proposed MW-SPA are simple, economic and, more importantly, have high throughput. Full article

(This article belongs to the Special Issue Derivatization in Analytical Chemistry)

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21 pages, 2863 KiB

Open AccessArticle

Bioactive Secoiridoids in Italian Extra-Virgin Olive Oils: Impact of Olive Plant Cultivars, Cultivation Regions and Processing

by Ilario Losito, Ramona Abbattista, Cristina De Ceglie, Andrea Castellaneta, Cosima Damiana Calvano and Tommaso R.I. Cataldi

Molecules 2021, 26(3), 743; https://doi.org/10.3390/molecules26030743 - 31 Jan 2021

Cited by 17 | Viewed by 4503

Abstract

In the last two decades, phenolic compounds occurring in olive oils known as secoiridoids have attracted a great interest for their bioactivity. Four major olive oil secoiridoids, i.e., oleuropein and ligstroside aglycones, oleacin and oleocanthal, were previously characterized in our laboratory using reversed-phase [...] Read more.

In the last two decades, phenolic compounds occurring in olive oils known as secoiridoids have attracted a great interest for their bioactivity. Four major olive oil secoiridoids, i.e., oleuropein and ligstroside aglycones, oleacin and oleocanthal, were previously characterized in our laboratory using reversed-phase liquid chromatography with electrospray ionization-Fourier transform-mass spectrometry (RPLC-ESI-FTMS). The same analytical approach, followed by multivariate statistical analysis (i.e., Principal Component Analysis), was applied here to a set of 60 Italian extra-virgin olive oils (EVOO). The aim was to assess the secoiridoid contents as a function of olive cultivars, place of cultivation (i.e., different Italian regions) and olive oil processing, in particular two- vs. three-phase horizontal centrifugation. As expected, higher secoiridoid contents were generally found in olive oils produced by two-phase horizontal centrifugation. Moreover, some region/cultivar-related trends were evidenced, as oleuropein and ligstroside aglycones prevailed in olive oils produced in Apulia (Southern Italy), whereas the contents of oleacin and oleocanthal were relatively higher in EVOO produced in Central Italy (Tuscany, Lazio and Umbria). A lower content of all the four secoiridoids was generally found in EVOO produced in Sicily (Southern Italy) due to the intrinsic low abundance of these bioactive compounds in cultivars typical of that region. Full article

(This article belongs to the Special Issue Isolation, Identification and Bioactivity of Food-Derived Compounds)

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Molecules, Volume 26, Issue 3 (February-1 2021) – 256 articles

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