Molecules

Open AccessArticle

Effects of Oat β-Glucan on the Textural and Sensory Properties of Low-Fat Set Type Pea Protein Yogurt

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Molecules 2023, 28(7), 3067; https://doi.org/10.3390/molecules28073067 (registering DOI) - 29 Mar 2023

Abstract

This study investigated the effect of oat β-glucan as a fat substitute on the structure formation, texture, and sensory properties of pea protein yogurt. The results showed that the incorporation of 0.5% β-glucan significantly accelerated the lactic acid bacteria-induced fermentation, with the time [...] Read more.

This study investigated the effect of oat β-glucan as a fat substitute on the structure formation, texture, and sensory properties of pea protein yogurt. The results showed that the incorporation of 0.5% β-glucan significantly accelerated the lactic acid bacteria-induced fermentation, with the time for reaching the target pH of 4.6 shortened from 3.5 h to 3 h (p < 0.05); increased the plastic module (G’) from 693 Pa to 764 Pa when fermenting 3 h (p < 0.05); and enhanced the water-holding capacity from 77.29% to 82.15% (p < 0.05). The identification of volatile organic compounds (VOCs) in low-fat pea protein yogurt by GC-IMS revealed a significant decrease in aldehydes and a significant increase in alcohols, ketones and acids in the pea yogurt after fermentation (p < 0.05). Among them, the levels of acetic acid, acetone, 2,3-butanedione, 3-hydroxy-2-butanone, and ethyl acetate all significantly increased with the addition of oat β-glucan (p < 0.05), thereby providing prominent fruity, sweet, and creamy flavors, respectively. Combined with the results of sensory analysis, the quality characteristics of pea protein yogurt with 1% oil by adding 1% oat β-glucan were comparable to the control sample with 3% oil. Therefore, oat β-glucan has a good potential for fat replacement in pea protein yogurt. Full article

(This article belongs to the Special Issue Extraction, Modification, Functionality and Bioactivity of Plant Proteins for a Healthy and Sustainable Food System)

Open AccessArticle

Changes in Physicochemical and Bioactive Properties of Quince (Cydonia oblonga Mill.) and Its Products

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Bożena Waszkiewicz-Robak

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Arkadiusz Szterk

Molecules 2023, 28(7), 3066; https://doi.org/10.3390/molecules28073066 (registering DOI) - 29 Mar 2023

Abstract

Quince (Cydonia oblonga Miller) is a plant that is commonly cultivated around the world, known for centuries for its valuable nutritional and healing properties. Although quince fruit are extremely aromatic, due to their high hardness and sour, astringent, and bitter taste, they [...] Read more.

Quince (Cydonia oblonga Miller) is a plant that is commonly cultivated around the world, known for centuries for its valuable nutritional and healing properties. Although quince fruit are extremely aromatic, due to their high hardness and sour, astringent, and bitter taste, they are not suitable for direct consumption in an unprocessed form. However, they are an important raw material in fruit processing, e.g., in the production of jams, jellies, and juices. Quince fruits fall under the category of temperate fruits, so their shelf life can be predicted. Considering that technological processing affects not only the organoleptic properties and shelf life but also the functional properties of fruits, the aim of this research was to determine the impact of various types of technological treatments on the physicochemical and bioactive properties of quince fruit. In fresh, boiled, and fried fruits and in freshly squeezed quince fruit juice, basic parameters, such as the content of dry matter, moisture, soluble solids (°Brix), pH, total acidity, water activity, and color parameters (L*a*b*) were determined. The content of key bioactive ingredients, i.e., tannins, carotenoids, flavonoids, phenolic acids, and total polyphenols, was also determined, as well as the antioxidant activity of raw and technologically processed (cooked, fried, and squeezed) quince fruits. The conducted research showed that fresh quince fruit and processed quince products can be a very good source of bioactive ingredients in the diet, such as tannins (3.64 ± 0.06 mg/100 g in fresh fruit; from 2.22 ± 0.02 mg/100 g to 5.59 ± 0.15 g/100 g in products), carotenoids (44.98 ± 0.18 mg/100 g in fresh fruit; from 141.88 ± 0.62 mg/100 g to 166.12 ± 0.62 mg/100 g in products), and polyphenolic compounds (246.98 ± 6.76 mg GAE/100 g in fresh fruit; from 364.53 ± 3.76 mg/100 g to 674.21 ± 4.49 mg/100 g in products). Quince fruit and quince products are also characterized by high antioxidant properties (452.41 ± 6.50 µM TEAC/100 g in fresh fruit; 520.78 ± 8.56 µM TEAC/100 g to 916.16 ± 6.55 µM TEAC/100 g in products). The choice of appropriate technological processing for the quince fruit may allow producers to obtain high-quality fruit preserves and act a starting point for the development of functional products with the addition of quince fruit in its various forms, with high health-promoting values and a wide range of applications in both the food and pharmaceutical industries. Full article

(This article belongs to the Special Issue Impact of Processing on Plant Bioactive Composition in Sustainable Foods)

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Open AccessArticle

A PET Fluorescent Probe for Dynamic Pd²⁺ Tracking with Imaging Applications in the Nanofiber and Living Cells

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Molecules 2023, 28(7), 3065; https://doi.org/10.3390/molecules28073065 (registering DOI) - 29 Mar 2023

Abstract

Constructed on the moiety of a lactam screw ring, a near-infrared fluorescent probe RCya for Pd²⁺ was designed under the PET mechanism and synthesized by incorporating 2,4-dihydroxybenzaldehyde as the recognition group. Dynamic detection of aqueous Pd²⁺ by the probe RCya could [...] Read more.

Constructed on the moiety of a lactam screw ring, a near-infrared fluorescent probe RCya for Pd²⁺ was designed under the PET mechanism and synthesized by incorporating 2,4-dihydroxybenzaldehyde as the recognition group. Dynamic detection of aqueous Pd²⁺ by the probe RCya could be accomplished through ion competition, linear response, fluorescence-pH/time stabilities, and other optical tests. Moreover, the high selectivity, low cytotoxicity, cell permeability, and lysosome accumulation properties of RCya enabled the imaging applications on solid-state RCya–PAN composite nanofibers and in living cells. The recognition mechanism of probe RCya toward Pd²⁺ was further studied through simulation calculation and MS analysis. Full article

(This article belongs to the Section Analytical Chemistry)

Open AccessArticle

Coalescence and Break-Up Behaviors of Nanodroplets under AC Electric Field

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Molecules 2023, 28(7), 3064; https://doi.org/10.3390/molecules28073064 (registering DOI) - 29 Mar 2023

Abstract

Water must be separated from water-in-oil (W/O) emulsion because of the corrosion it brings to the relative equipment in the process of transportation and storage. It is an effective method to apply external electric field to achieve high performance of separating small, dispersed [...] Read more.

Water must be separated from water-in-oil (W/O) emulsion because of the corrosion it brings to the relative equipment in the process of transportation and storage. It is an effective method to apply external electric field to achieve high performance of separating small, dispersed water droplets from W/O emulsion; however, the coalescing micromechanism of such small salty droplets under AC electric field is unclear. In this paper, molecular dynamics simulation was adopted to investigate the coalescence and separation process of two NaCl-aqueous droplets under AC electric field and discuss the effect of AC electric field frequency, as well as the time required for contacting, the critical electric field strength, the dynamic coalescence process and the stability of the final merged droplet. The results show that the critical electric field strength of the droplet coalescence increases with the increase of frequency, while the time required for droplet contacting becomes shorter. The shrinkage function curve was applied to characterize the droplet coalescence effect and it was found that the droplets coalescence and form a nearly spherical droplet under the AC electric field with a frequency of 1.25 GHz and strength of 0.5 V/nm. When the electric field frequency is 10 GHZ, the merged droplet presents a periodic fluctuation with the same period as the AC electric field, which mainly depends on the periodic movement of cations and anions under the AC electric field. The results can provide theoretical basis for the practical application of electrostatic demulsification technology in the petroleum or chemical industry from the microscopic perspective. Full article

(This article belongs to the Special Issue Exploration of the Separation Processes in Nanomaterials)

Open AccessArticle

Taipan Natriuretic Peptides Are Potent and Selective Agonists for the Natriuretic Peptide Receptor A

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Simone Vink

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Kalyana Bharati Akondi

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Molecules 2023, 28(7), 3063; https://doi.org/10.3390/molecules28073063 (registering DOI) - 29 Mar 2023

Abstract

Cardiovascular ailments are a major cause of mortality where over 1.3 billion people suffer from hypertension leading to heart-disease related deaths. Snake venoms possess a broad repertoire of natriuretic peptides with therapeutic potential for treating hypertension, congestive heart failure, and related cardiovascular disease. [...] Read more.

Cardiovascular ailments are a major cause of mortality where over 1.3 billion people suffer from hypertension leading to heart-disease related deaths. Snake venoms possess a broad repertoire of natriuretic peptides with therapeutic potential for treating hypertension, congestive heart failure, and related cardiovascular disease. We now describe several taipan (Oxyuranus microlepidotus) natriuretic peptides TNPa-e which stimulated cGMP production through the natriuretic peptide receptor A (NPR-A) with higher potencies for the rat NPR-A (rNPR-A) over human NPR-A (hNPR-A). TNPc and TNPd were the most potent, demonstrating 100- and 560-fold selectivity for rNPR-A over hNPR-A. In vivo studies found that TNPc decreased diastolic and systolic blood pressure (BP) and increased heart rate (HR) in conscious normotensive rabbits, to a level that was similar to that of human atrial natriuretic peptide (hANP). TNPc also enhanced the bradycardia due to cardiac afferent stimulation (Bezold–Jarisch reflex). This indicated that TNPc possesses the ability to lower blood pressure and facilitate cardiac vagal afferent reflexes but unlike hANP does not produce tachycardia. The 3-dimensional structure of TNPc was well defined within the pharmacophoric disulfide ring, displaying two turn-like regions (RMSD = 1.15 Å). Further, its much greater biological stability together with its selectivity and potency will enhance its usefulness as a biological tool. Full article

(This article belongs to the Special Issue Biodiscovery Downunder: Natural Products Chemistry in Australia)

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Open AccessArticle

Regioselective Cyclic Iminium Formation of Ugi Advanced Intermediates: Rapid Access to 3,4-Dihydropyrazin-2(1H)-ones and Other Diverse Nitrogen-Containing Heterocycles

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Naděžda Cankařová

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Viktor Krchňák

Molecules 2023, 28(7), 3062; https://doi.org/10.3390/molecules28073062 (registering DOI) - 29 Mar 2023

Abstract

Herein, advanced intermediates were synthesized through Ugi four-component reactions of isocyanides, aldehydes, masked amino aldehyde, and carboxylic acids, including N-protected amino acids. The presence of a masked aldehyde enabled acid-mediated deprotection and subsequent cyclization via the carbonyl carbon and the amide nitrogen. [...] Read more.

Herein, advanced intermediates were synthesized through Ugi four-component reactions of isocyanides, aldehydes, masked amino aldehyde, and carboxylic acids, including N-protected amino acids. The presence of a masked aldehyde enabled acid-mediated deprotection and subsequent cyclization via the carbonyl carbon and the amide nitrogen. Utilizing N-protected amino acid as a carboxylic acid component, Ugi intermediates could be cyclized from two possible directions to target 3,4-dihydropyrazin-2(1H)-ones. Cyclization to the amino terminus (westbound) and to the carboxyl terminus (eastbound) was demonstrated. Deliberate selection of building blocks drove the reaction regioselectively and yielded diverse heterocycles containing a 3,4-dihydropyrazin-2(1H)-one core, pyrazin-2(1H)-one, and piperazin-2-one, as well as a tricyclic framework with a 3D architecture, 2,3-dihydro-2,6-methanobenzo[h][¹,³,6]triazonine-4,7(1H,5H)-dione, from Ugi adducts under mild reaction conditions. The latter bridged heterocycle was achieved diastereoselectively. The reported chemistry represents diversity-oriented synthesis. One common Ugi advanced intermediate was, without isolation, rapidly transformed into various nitrogen-containing heterocycles. Full article

(This article belongs to the Special Issue Heterocyclic Chemistry with Applications)

Open AccessArticle

Assessment of the Anticancer Effect of Chlorojanerin Isolated from Centaurothamnus maximus on A549 Lung Cancer Cells

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Molecules 2023, 28(7), 3061; https://doi.org/10.3390/molecules28073061 (registering DOI) - 29 Mar 2023

Abstract

The goal of this study was to assess the anticancer efficacy of chlorojanerin against various cancer cells. The effects of chlorojanerin on cell cytotoxicity, cell cycle arrest, and cell apoptosis were examined using MTT assay, propidium iodide staining, and FITC Annexin V assay. [...] Read more.

The goal of this study was to assess the anticancer efficacy of chlorojanerin against various cancer cells. The effects of chlorojanerin on cell cytotoxicity, cell cycle arrest, and cell apoptosis were examined using MTT assay, propidium iodide staining, and FITC Annexin V assay. RT-PCR was employed to determine the expression levels of apoptosis-related genes. Furthermore, docking simulations were utilized to further elucidate the binding preferences of chlorojanerin with Bcl-2. According to MTT assay, chlorojanerin inhibited the proliferation of all tested cells in a dose-dependent manner with a promising effect against A549 lung cancer cells with an IC₅₀ of 10 µM. Cell growth inhibition by chlorojanerin was linked with G2/M phase cell cycle arrest in A549 treated cells. Flow cytometry analysis indicated that the proliferation inhibition effect of chlorojanerin was associated with apoptosis induction in A549 cells. Remarkably, chlorojanerin altered the expression of many genes involved in apoptosis initiation. Moreover, we determined that chlorojanerin fit into the active site of Bcl-2 according to the molecular docking study. Collectively, our results demonstrate that chlorojanerin mediated an anticancer effect involving cell cycle arrest and apoptotic cell death and, therefore, could potentially serve as a therapeutic agent in lung cancer treatment. Full article

(This article belongs to the Special Issue Biological Activities of Natural Products III)

Open AccessReview

Biosynthesis of Nanoparticles Using Plant Extracts and Essential Oils

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Sérgio Antunes Filho

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Mayara Santana dos Santos

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Otávio Augusto L. dos Santos

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Bianca Pizzorno Backx

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Molecules 2023, 28(7), 3060; https://doi.org/10.3390/molecules28073060 (registering DOI) - 29 Mar 2023

Abstract

Plant extracts and essential oils have a wide variety of molecules with potential application in different fields such as medicine, the food industry, and cosmetics. Furthermore, these plant derivatives are widely interested in human and animal health, including potent antitumor, antifungal, anti-inflammatory, and [...] Read more.

Plant extracts and essential oils have a wide variety of molecules with potential application in different fields such as medicine, the food industry, and cosmetics. Furthermore, these plant derivatives are widely interested in human and animal health, including potent antitumor, antifungal, anti-inflammatory, and bactericidal activity. Given this diversity, different methodologies were needed to optimize the extraction, purification, and characterization of each class of biomolecules. In addition, these plant products can still be used in the synthesis of nanomaterials to reduce the undesirable effects of conventional synthesis routes based on hazardous/toxic chemical reagents and associate the properties of nanomaterials with those present in extracts and essential oils. Vegetable oils and extracts are chemically complex, and although they are already used in the synthesis of nanomaterials, limited studies have examined which molecules are effectively acting in the synthesis and stabilization of these nanostructures. Similarly, few studies have investigated whether the molecules coating the nanomaterials derived from these extracts and essential oils would bring benefits or somehow reduce their potential activity. This synergistic effect presents a promising field to be further explored. Thus, in this review article, we conducted a comprehensive review addressing the main groups of molecules present in plant extracts and essential oils, their extraction capacity, and available methodologies for their characterization. Moreover, we highlighted the potential of these plant products in the synthesis of different metallic nanomaterials and their antimicrobial capacity. Furthermore, we correlated the extract’s role in antimicrobial activity, considering the potential synergy between molecules from the plant product and the different metallic forms associated with nanomaterials. Full article

(This article belongs to the Special Issue Antibacterial Properties of Plant Extracts: Preparation and Application)

Open AccessReview

Recent Progress in Heterocycle Synthesis: Cyclization Reaction with Pyridinium and Quinolinium 1,4-Zwitterions

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Molecules 2023, 28(7), 3059; https://doi.org/10.3390/molecules28073059 (registering DOI) - 29 Mar 2023

Abstract

Heteroarene 1, n-zwitterions are powerful and versatile building blocks in the construction of heterocycles and have received increasing attention in recent years. In particular, pyridinium and quinolinium 1,4-zwitterions have been widely studied and used in a variety of cyclization reactions due to their [...] Read more.

Heteroarene 1, n-zwitterions are powerful and versatile building blocks in the construction of heterocycles and have received increasing attention in recent years. In particular, pyridinium and quinolinium 1,4-zwitterions have been widely studied and used in a variety of cyclization reactions due to their air stability, ease of use, and high efficiency. Sulfur- and nitrogen-based pyridinium and quinolinium 1,4-zwitterions, types of emerging heteroatom-containing synthons, have attracted much attention from chemists. These 1,4-zwitterions, which contain multiple reaction sites, have been successfully used in the synthesis of three- to eight-membered cyclic compounds over the last decade. In this review, we present the exciting progress made in the field of cyclization reactions of sulfur- and nitrogen-based pyridinium and quinolinium 1,4-zwitterions. Moreover, the mechanistic insights, the transition states, some synthetic applications, and the challenges and opportunities are also discussed. We hope to provide an overview for synthetic chemists who are interested in the heterocycle synthesis from cyclization reaction with pyridinium and quinolinium 1,4-zwitterions pyridinium and quinolinium 1,4-zwitterions. Full article

(This article belongs to the Special Issue Novel Organic Synthetic Route to Heterocyclic Compounds)

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Open AccessArticle

Half-Sandwich Type Platinum-Group Metal Complexes of C-Glucosaminyl Azines: Synthesis and Antineoplastic and Antimicrobial Activities

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Molecules 2023, 28(7), 3058; https://doi.org/10.3390/molecules28073058 (registering DOI) - 29 Mar 2023

Abstract

While platinum-based compounds such as cisplatin form the backbone of chemotherapy, the use of these compounds is limited by resistance and toxicity, driving the development of novel complexes with cytostatic properties. In this study, we synthesized a set of half-sandwich complexes of platinum-group [...] Read more.

While platinum-based compounds such as cisplatin form the backbone of chemotherapy, the use of these compounds is limited by resistance and toxicity, driving the development of novel complexes with cytostatic properties. In this study, we synthesized a set of half-sandwich complexes of platinum-group metal ions (Ru(II), Os(II), Ir(III) and Rh(III)) with an N,N-bidentate ligand comprising a C-glucosaminyl group and a heterocycle, such as pyridine, pyridazine, pyrimidine, pyrazine or quinoline. The sugar-containing ligands themselves are unknown compounds and were obtained by nucleophilic additions of lithiated heterocycles to O-perbenzylated 2-nitro-glucal. Reduction of the adducts and, where necessary, subsequent protecting group manipulations furnished the above C-glucosaminyl heterocycles in their O-perbenzylated, O-perbenzoylated and O-unprotected forms. The derived complexes were tested on A2780 ovarian cancer cells. Pyridine, pyrazine and pyridazine-containing complexes proved to be cytostatic and cytotoxic on A2780 cells, while pyrimidine and quinoline derivatives were inactive. The best complexes contained pyridine as the heterocycle. The metal ion with polyhapto arene/arenyl moiety also impacted on the biological activity of the complexes. Ruthenium complexes with p-cymene and iridium complexes with Cp* had the best performance in ovarian cancer cells, followed by osmium complexes with p-cymene and rhodium complexes with Cp*. Finally, the chemical nature of the protective groups on the hydroxyl groups of the carbohydrate moiety were also key determinants of bioactivity; in particular, O-benzyl groups were superior to O-benzoyl groups. The IC₅₀ values of the complexes were in the low micromolar range, and, importantly, the complexes were less active against primary, untransformed human dermal fibroblasts; however, the anticipated therapeutic window is narrow. The bioactive complexes exerted cytostasis on a set of carcinomas such as cell models of glioblastoma, as well as breast and pancreatic cancers. Furthermore, the same complexes exhibited bacteriostatic properties against multiresistant Gram-positive Staphylococcus aureus and Enterococcus clinical isolates in the low micromolar range. Full article

(This article belongs to the Special Issue Synthesis and Applications in Catalysis or as Anticancer and Antimicrobial Agents of Unique Organometallic Compounds)

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Open AccessArticle

Cleistocalyx nervosum var. paniala Berry Seed Protects against TNF-α-Stimulated Neuroinflammation by Inducing HO-1 and Suppressing NF-κB Mechanism in BV-2 Microglial Cells

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Sakawrat Janpaijit

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Chanin Sillapachaiyaporn

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Atsadang Theerasri

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Somsri Charoenkiatkul

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Monruedee Sukprasansap

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Tewin Tencomnao

Molecules 2023, 28(7), 3057; https://doi.org/10.3390/molecules28073057 (registering DOI) - 29 Mar 2023

Abstract

Sustained inflammatory responses have been implicated in various neurodegenerative diseases (NDDs). Cleistocalyx nervosum var. paniala (CN), an indigenous berry, has been reported to exhibit several health-beneficial properties. However, investigation of CN seeds is still limited. The objective of this study was to evaluate [...] Read more.

Sustained inflammatory responses have been implicated in various neurodegenerative diseases (NDDs). Cleistocalyx nervosum var. paniala (CN), an indigenous berry, has been reported to exhibit several health-beneficial properties. However, investigation of CN seeds is still limited. The objective of this study was to evaluate the protective effects of ethanolic seed extract (CNSE) and mechanisms in BV-2 mouse microglial cells using an inflammatory stimulus, TNF-α. Using LC-MS, ferulic acid, aurentiacin, brassitin, ellagic acid, and alpinetin were found in CNSE. Firstly, we examined molecular docking to elucidate its bioactive components on inflammation-related mechanisms. The results revealed that alpinetin, aurentiacin, and ellagic acid inhibited the NF-κB activation and iNOS function, while alpinetin and aurentiacin only suppressed the COX-2 function. Our cell-based investigation exhibited that cells pretreated with CNSE (5, 10, and 25 μg/mL) reduced the number of spindle cells, which was highly observed in TNF-α treatment (10 ng/mL). CNSE also obstructed TNF-α, IL-1β, and IL-6 mRNA levels and repressed the TNF-α and IL-6 releases in a culture medium of BV-2 cells. Remarkably, CNSE decreased the phosphorylated forms of ERK, p38MAPK, p65, and IκB-α related to the inhibition of NF-κB binding activity. CNSE obviously induced HO-1 protein expression. Our findings suggest that CNSE offers good potential for preventing inflammatory-related NDDs. Full article

(This article belongs to the Special Issue Natural Products from Medicinal Plants)

Open AccessArticle

Selenonium Salt as a Catalyst for Nucleophilic Substitution Reactions in Water: Synthesis of Thiocyanites and Selenocyanates

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Alix Y. Bastidas Ángel

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Philipe Raphael O. Campos

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Eduardo E. Alberto

Molecules 2023, 28(7), 3056; https://doi.org/10.3390/molecules28073056 (registering DOI) - 29 Mar 2023

Abstract

Organothiocyanates and selenocyanates are valuable compounds, both in terms of functional group interconversion and due to their biological activities. In this contribution, we report the synthesis of a series of these important substances in a mixture of water and dimethyl carbonate (20/1 proportion) [...] Read more.

Organothiocyanates and selenocyanates are valuable compounds, both in terms of functional group interconversion and due to their biological activities. In this contribution, we report the synthesis of a series of these important substances in a mixture of water and dimethyl carbonate (20/1 proportion) using potassium thio- or selenocyanates salts and organic bromides. The key to the effectiveness of the reaction is a chalcogen bond interaction between a selenonium salt catalyst and the organic substrate. Full article

(This article belongs to the Special Issue Advances in Selenium Catalysts and Antioxidants)

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Open AccessArticle

Yield and Composition of the Essential Oil of the Opopanax Genus in Turkey

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Molecules 2023, 28(7), 3055; https://doi.org/10.3390/molecules28073055 (registering DOI) - 29 Mar 2023

Abstract

The genus Opopanax W. Koch (Apiaceae) is represented by four species in Turkey. The composition of the essential oil of Opopanax genus members (Apiaceae) growing in Turkey was investigated in this study. GC-MS was used to analyze the composition of Opopanax essential oil [...] Read more.

The genus Opopanax W. Koch (Apiaceae) is represented by four species in Turkey. The composition of the essential oil of Opopanax genus members (Apiaceae) growing in Turkey was investigated in this study. GC-MS was used to analyze the composition of Opopanax essential oil samples that were taken from their natural environments. The Clevenger apparatus was used to hydrodistill the plant’s aerial parts, and the yields were determined to be between 0.2% v/w (for O. siifolius) and 0.4% (for O. hispidus, O. chironium, and O. persicus). The results and the chemical data provided some information and clues on the chemotaxonomy of the genus Opopanax. In this study, γ-elemene, butanoic acid octyl ester, and cylopropane were the main compounds identified in the essential oils of O. chironium, O. hispidus, and O. persicus. In particular, hexynyl n-valerate was most abundant in the essential oil of O. chironium, cyclopropane in that of O. hispidus, γ-elemene in that of O. persicus, and n-hexadecanoic acid/palmitic acid in that of O. siifolius. In a chemotaxonomic approach, the essential oil analysis of the Opopanax species revealed that these species conformed in a cluster analysis with their morphological classification. The constituents of the essential oils of all examined in the genus Opopanax were determined in this study, which is the most thorough one to date. This study provides new information about the composition of the essential oils of the investigated species. Full article

(This article belongs to the Special Issue Extraction, Separation and Identification of Compounds from Natural Sources)

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Open AccessArticle

4,5-Dihydro-5-Oxo-Pyrazolo[1,5-a]Thieno[2,3-c]Pyrimidine: A Novel Scaffold Containing Thiophene Ring. Chemical Reactivity and In Silico Studies to Predict the Profile to GABA_A Receptor Subtype

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Maria Paola Giovannoni

Molecules 2023, 28(7), 3054; https://doi.org/10.3390/molecules28073054 (registering DOI) - 29 Mar 2023

Abstract

The isosteric replacement of the benzene with thiophene ring is a chemical modification widely applied in medicinal chemistry. Several drugs containing the thiophene ring are marketed for treating various pathologies (osteoporosis, peripheral artery disorder, psychosis, anxiety and convulsion). Taking into account this evidence [...] Read more.

The isosteric replacement of the benzene with thiophene ring is a chemical modification widely applied in medicinal chemistry. Several drugs containing the thiophene ring are marketed for treating various pathologies (osteoporosis, peripheral artery disorder, psychosis, anxiety and convulsion). Taking into account this evidence and as a continuation of our study in the GABA_A receptor modulators field, we designed and synthesized new compounds containing the thiophene ring with 4,5-dihydro-5-oxo-pyrazolo[1,5-a]thieno[2,3-c]pyrimidine and pyrazolo[1,5-a]thieno[2,3-c] pyrimidine scaffold. Moreover, these cores, never reported in the literature, are isosteres of pyrazolo[1,5-a]quinazolines (PQ), previously published by us as GABA_AR subtype ligands. We introduced in the new scaffold those functions and groups (esters, ketones, alpha/beta-thiophene) that in our PQ derivatives were responsible for the activity, and at the same time, we have extensively investigated the reactivity of the new nucleus regarding the alkylation, reduction, halogenation and hydrolyses. On the six final designed compounds (12c–f, 22a,b) molecular docking and dynamic simulation studies have been performed. The analysis of dynamic simulation, applying our reported model ‘Proximity Frequencies’, collocates with high probability 12c, 22b, in the agonist class towards α1β2γ2-GABA_AR. Full article

(This article belongs to the Special Issue Synthesis of Heteroaromatic Compounds)

Open AccessReview

Localized Therapeutic Approaches Based on Micro/Nanofibers for Cancer Treatment

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Molecules 2023, 28(7), 3053; https://doi.org/10.3390/molecules28073053 (registering DOI) - 29 Mar 2023

Abstract

Cancer remains one of the most challenging health problems worldwide, and localized therapeutic approaches based on micro/nanofibers have shown potential for its treatment. Micro/nanofibers offer several advantages as a drug delivery system, such as high surface area, tunable pore size, and sustained release [...] Read more.

Cancer remains one of the most challenging health problems worldwide, and localized therapeutic approaches based on micro/nanofibers have shown potential for its treatment. Micro/nanofibers offer several advantages as a drug delivery system, such as high surface area, tunable pore size, and sustained release properties, which can improve drug efficacy and reduce side effects. In addition, functionalization of these fibers with nanoparticles can enhance their targeting and therapeutic capabilities. Localized delivery of drugs and/or other therapeutic agents via micro/nanofibers can also help to overcome the limitations of systemic administration, such as poor bioavailability and off-target effects. Several studies have shown promising results in preclinical models of cancer, including inhibition of tumor growth and improved survival rates. However, more research is needed to overcome technical and regulatory challenges to bring these approaches to clinical use. Localized therapeutic approaches based on micro/nanofibers hold great promise for the future of cancer treatment, providing a targeted, effective, and minimally invasive alternative to traditional treatments. The main focus of this review is to explore the current treatments utilizing micro/nanofibers, as well as localized drug delivery systems that rely on fibrous structures to deliver and release drugs for the treatment of cancer in a specific area. Full article

(This article belongs to the Special Issue Review Papers in Materials Chemistry)

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Open AccessArticle

Critical Analysis of Association Constants between Calixarenes and Nitroaromatic Compounds Obtained by Fluorescence. Implications for Explosives Sensing

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Alexandre S. Miranda

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Paula M. Marcos

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José R. Ascenso

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Mário N. Berberan-Santos

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Peter J. Cragg

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Rachel Schurhammer

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Christophe Gourlaouen

Molecules 2023, 28(7), 3052; https://doi.org/10.3390/molecules28073052 (registering DOI) - 29 Mar 2023

Abstract

The binding behaviour of two ureido-hexahomotrioxacalix[3]arene derivatives bearing naphthyl (1) and pyrenyl (2) fluorogenic units at the lower rim towards selected nitroaromatic compounds (NACs) was evaluated. Their affinity, or lack of it, was determined by UV-Vis absorption, fluorescence and [...] Read more.

The binding behaviour of two ureido-hexahomotrioxacalix[3]arene derivatives bearing naphthyl (1) and pyrenyl (2) fluorogenic units at the lower rim towards selected nitroaromatic compounds (NACs) was evaluated. Their affinity, or lack of it, was determined by UV-Vis absorption, fluorescence and NMR spectroscopy. Different computational methods were also used to further investigate any possible complexation between the calixarenes and the NACs. All the results show no significant interaction between calixarenes 1 and 2 and the NACs in either dichloromethane or acetonitrile solutions. Moreover, the fluorescence quenching observed is only apparent and merely results from the absorption of the NACs at the excitation wavelength (inner filter effect). This evidence is in stark contrast with reports in the literature for similar calixarenes. A naphthyl urea dihomooxacalix[4]arene (3) is also subject to the inner filter effect and is shown to form a stable complex with trinitrophenol; however, the equilibrium association constant is greatly overestimated if no correction is applied (9400 M⁻¹ vs 3000 M⁻¹), again stressing the importance of taking into account the inner filter effect in these systems. Full article

(This article belongs to the Special Issue Calixarene Complexes: Synthesis, Properties and Applications II)

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Open AccessReview

Ionic Liquids as Promisingly Multi-Functional Participants for Electrocatalyst of Water Splitting: A Review

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Molecules 2023, 28(7), 3051; https://doi.org/10.3390/molecules28073051 (registering DOI) - 29 Mar 2023

Abstract

Ionic liquids (ILs), as one of the most concerned functional materials in recent decades, have opened up active perspectives for electrocatalysis. In catalyst preparation, ILs act as characteristic active components besides media and templates. Compared with catalysts obtained using ordinary reagents, IL-derived catalysts [...] Read more.

Ionic liquids (ILs), as one of the most concerned functional materials in recent decades, have opened up active perspectives for electrocatalysis. In catalyst preparation, ILs act as characteristic active components besides media and templates. Compared with catalysts obtained using ordinary reagents, IL-derived catalysts have a special structure and catalytic performance due to the influence of IL’s special physicochemical properties and structures. This review mainly describes the use of ILs as modifiers and reaction reagents to prepare electrocatalysts for water splitting. The designability of ILs provides opportunities for the ingenious composition of cations or anions. ILs containing heteroatoms (N, O, S, P, etc.) and transition metal anion (FeCl₄⁻, NiCl₃⁻, etc.) can be used to directly prepare metal phosphides, sulfides, carbides and nitrides, and so forth. The special physicochemical properties and supramolecular structures of ILs can provide growth conditions for catalysts that are different from the normal media environment, inducing special structure and high performance. ILs as heteroatom sources are safe, green and easy to operate compared with traditional heteroatom sources. The strategy for using ILs as reagents is expected to realize 100% atomic transformation of reactants, in line with the concept of green chemistry. This review reflects the discovered work with the best findings from the literature. It will offer readers a deeper understanding on the development of IL-derived electrocatalysts and inspire them to ingeniously design high-performance electrocatalysts for water splitting. Full article

(This article belongs to the Section Inorganic Chemistry)

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Open AccessArticle

Evolution of Seed-Soluble and Insoluble Tannins during Grape Berry Maturation

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Molecules 2023, 28(7), 3050; https://doi.org/10.3390/molecules28073050 (registering DOI) - 29 Mar 2023

Abstract

Condensed tannins (CT) in wine are derived from the seeds and skins of grapes, and their composition and content contribute to the bitterness/astringency characteristics and ageing potential of the wine. Global warming has accelerated the ripening process of grape berries, making them out [...] Read more.

Condensed tannins (CT) in wine are derived from the seeds and skins of grapes, and their composition and content contribute to the bitterness/astringency characteristics and ageing potential of the wine. Global warming has accelerated the ripening process of grape berries, making them out of sync with seed ripening. To understand the influence of berry ripening on the seed CT composition and content, we analyzed the changes in the soluble and insoluble CT in the seeds of ‘Cabernet Sauvignon’ grapes from two vineyards over two years. The results showed that the seed-soluble CT presented a slight downward trend in fluctuation during grape berry development, while the insoluble CT increased continuously before the véraison and remained at a high level afterwards. Relatively speaking, a lower sugar increment in developing grape berries favored the conversion of seed CT towards a higher degree of polymerization. The terminal unit of soluble CT was dominated by epigallocatechin gallate, the content of which decreased as the seeds matured. It is suggested that the seeds should be fully matured to reduce this bitter component in tannins. This study provides a reference for us to control the grape ripening process and produce high-quality grapes for wine making. Full article

(This article belongs to the Section Natural Products Chemistry)

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Open AccessArticle

Characterization of Complexes between Imidacloprid and β-Cyclodextrin: Evaluation of the Toxic Activity in Algae and Rotifers

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Molecules 2023, 28(7), 3049; https://doi.org/10.3390/molecules28073049 (registering DOI) - 29 Mar 2023

Abstract

The development of new formulations can be driven by the knowledge of host–guest complexes using cyclodextrins which have the ability to include guest molecules within their hydrophobic cavities, improving the physicochemical properties of the guest. To rationally explore new pesticide formulations, the effects [...] Read more.

The development of new formulations can be driven by the knowledge of host–guest complexes using cyclodextrins which have the ability to include guest molecules within their hydrophobic cavities, improving the physicochemical properties of the guest. To rationally explore new pesticide formulations, the effects of cyclodextrins on the properties of such guest molecules need to be explored. Imidacloprid is a neonicotinoid systemic insecticide used worldwide. In this study, the inclusion complexes of Imidacloprid (IMI) with β-cyclodextrin (β-CD) were prepared in the solid state by co-precipitation and the physical mixing method, with a stoichiometry of 1:1 and 1:2 molar ratios. The obtained products, Imidacloprid:β-cyclodextrin inclusion complex (IMI:β-CD), were characterized in the solid state by Fourier transform-infrared (FT-IR) spectroscopy and X-ray powder diffractometry (XRD). In solution, the 1:1 stoichiometry for the inclusion complexes was established by the Job plot method, and the binding constant of IMI:β-CD was determined by UV–vis titration. The toxicity was determined in producers and primary consumers of the freshwater trophic chain, the green alga Raphidocelis subcapitata and the rotifer Brachionus calyciflorus, respectively. The results indicated that Imidacloprid forms inclusion complexes with CDs showing improved physicochemical properties compared to free Imidacloprid. The formation of the inclusion complex reduced the chronic toxicity in rotifers when IMI concentrations were close to those of environmental concern (tenths/hundredths of micromoles/L). Therefore, CD inclusion complexes could provide important advantages to be considered for the future industrial production of new formulations. Full article

(This article belongs to the Special Issue Cyclodextrin Chemistry and Toxicology II)

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