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A special issue of Molecules (ISSN 1420-3049).

Deadline for manuscript submissions: closed (31 March 2022) | Viewed by 34395

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Prof. Dr. Farid Chemat

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Groupe de Recherche en Eco-Extraction de Produits Naturel, Institut National de Recherche pour l’Agriculture, l’Alimentation et l’Environnement, Université d´Avignon et des Pays du Vaucluse, 84029 Avignon, France
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Dr. Giuseppe Cirillo

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Department of Pharmacy, Health and Nutritional Sciences, University of Calabria, 87036 Rende, Italy
Interests: nanomaterials; biomaterials; carbon nanostructures; composite and hybrid materials; biomedical applications of functional materials; therapeutic devices; surface chemistry
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Prof. Dr. Diego Muñoz-Torrero

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Laboratory of Medicinal Chemistry, Faculty of Pharmacy and Food Sciences, Institute of Biomedicine (IBUB), University of Barcelona, Avenue Joan XXIII, 27-31, E-08028 Barcelona, Spain
Interests: multitarget anti-Alzheimer agents; hybrid compounds; cholinesterase inhibitors; amyloid anti-aggregating compounds; BACE-1 inhibitors; antiprotozoan compounds
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Prof. Dr. Roman Dembinski

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Department of Chemistry, Oakland University, 146 Library Drive, Rochester, MI 48309-4479, USA
Interests: organic, organometallic, and medicinal chemistry; organic synthesis; nucleosides; heterocycles; alkynes; fluorine and fluorous; cycloisomerizations; cyclizations
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Special Issue Information

Dear Colleagues,

In 2022, the 27th volume of our journal Molecules is being published. Thanks to our readers, innumerable authors, anonymous peer reviewers, editors, and all the people working in some way for the journal who have joined their efforts for years, the journal IF has reached currently 4.412.

To highlight another consecutive year of excellence, and to give a good start to the year, a special issue entitled “Molecules in 2022” is being launched. This special issue collects high quality original research and review articles in all areas of interest covered by Molecules. The special issue aims to collect papers of our editors-in-chief, editorial board members, guest editors, societies, authors, and reviewers from Molecules. The submission deadline will be 31 March 2022. We kindly encourage all research groups to contribute up-to-date results from latest development in your laboratory.

Prof. Dr. Farid Chemat
Dr. Giuseppe Cirillo
Prof. Dr. Diego Muñoz-Torrero
Prof. Dr. Roman Dembinski
Guest Editors

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Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. All submissions that pass pre-check are peer-reviewed. Accepted papers will be published continuously in the journal (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as short communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Molecules is an international peer-reviewed open access semimonthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 2700 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

New Year Special Issue Series

This Special Issue is a part of Molecules’s New Year Special Issue Series. The series reflects on the achievements, scientific progress, and “hot topics” of the previous year in the journal. Submissions of articles whose lead authors are our Editorial Board Members are highly encouraged. However, we welcome articles from all authors.

Keywords

organic chemistry
medicinal chemistry
natural products
inorganic chemistry
physical chemistry
materials science
nanoscience
catalysis
chemical biology
analytical chemistry
supramolecular chemistry
theoretical chemistry
green chemistry
photochemistry

Published Papers (12 papers)

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Research

10 pages, 3531 KiB

Open AccessArticle

Delta-8 Tetrahydrocannabinol Product Impurities

by Colleen L. Ray, Madison P. Bylo, Jonny Pescaglia, James A. Gawenis and C. Michael Greenlief

Molecules 2022, 27(20), 6924; https://doi.org/10.3390/molecules27206924 - 15 Oct 2022

Cited by 9 | Viewed by 3805

Abstract

Due to increased concerns regarding unidentified impurities in delta-8 tetrahydrocannabinol (Δ-8 THC) consumer products, a study using Nuclear Magnetic Resonance (NMR), high performance liquid chromatography (HPLC), and mass spectrometry (MS) was conducted to further investigate these products. Ten Δ-8 THC products, including distillates and ready to use vaporizer cartridges, were analyzed. The results yield findings that the tested products contain several impurities in concentrations far beyond what is declared on certificates of analysis for these products. As Δ-8 THC is a synthetic product synthesized from cannabidiol (CBD), there are valid concerns regarding the presence of impurities in these products with unknown effects on the human body. Compounding this problem is apparent inadequate testing of these products by producers and independent laboratories. Full article

(This article belongs to the Special Issue Molecules in 2022)

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11 pages, 5024 KiB

Open AccessArticle

A Convenient, Rapid, Conventional Heating Route to MIDA Boronates

by Andrew McGown, Anthony K. Edmonds, Daniel Guest, Verity L. Holmes, Chris Dadswell, Ramón González-Méndez, Charles A. I. Goodall, Mark C. Bagley, Barnaby W. Greenland and John Spencer

Molecules 2022, 27(16), 5052; https://doi.org/10.3390/molecules27165052 - 09 Aug 2022

Viewed by 1807

Abstract

A cheap, conventional, sealed heating reactor proved to be a useful alternative to a microwave reactor in the synthesis of a >20-member MIDA boronate library (MIDA = N-methyliminodiacetic acid). Reaction times were 10 min and work-ups were minimal, saving on energy and [...] Read more.

(This article belongs to the Special Issue Molecules in 2022)

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18 pages, 674 KiB

Open AccessArticle

Comparative Evaluation of the Nutrients, Phytochemicals, and Antioxidant Activity of Two Hempseed Oils and Their Byproducts after Cold Pressing

by Cristina Occhiuto, Gianluigi Aliberto, Mariarosaria Ingegneri, Domenico Trombetta, Clara Circosta and Antonella Smeriglio

Molecules 2022, 27(11), 3431; https://doi.org/10.3390/molecules27113431 - 26 May 2022

Cited by 17 | Viewed by 2383

Abstract

Recently, there has been a growing interest in the recovery of agri-food waste within the circular economy perspective. In this study, the nutritional, phytochemical, and biological features of the cold-pressed hempseed oil (HSO) and hempseed meal (HSM) of two industrial hemp varieties (USO 31 and Futura 75, THC ≤ 0.2%) were evaluated. The HSOs showed a high total phenols and flavonoid content, which were confirmed by LC-DAD-ESI-MS analysis, with rutin as the most abundant compound (56.93–77.89 µg/100 FW). They also proved to be a rich source of tocopherols (81.69–101.45 mg/100 g FW) and of a well-balanced ω-6 to ω-3 fatty acid ratio (3:1) with USO 31, which showed the best phytochemical profile and consequently the best antioxidant activity (about two times higher than Futura 75). The HSMs still retained part of the phytochemicals identified in the HSOs (polyphenols, tocopherols, and the preserved ω-6/ω-3 fatty acids ratio) and a modest antioxidant activity. Furthermore, they showed a very interesting nutritional profile, which was very rich in proteins (29.88–31.44 g/100 g FW), crude fibers (18.39–19.67 g/100 g), and essential and non-essential amino acids. Finally, only a restrained amount of anti-nutritional factors (trypsin inhibitors, phytic acid, and condensed tannins) was found, suggesting a promising re-use of these byproducts in the nutraceutical field. Full article

(This article belongs to the Special Issue Molecules in 2022)

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13 pages, 2911 KiB

Open AccessArticle

Cyanide Biodegradation by Trichoderma harzianum and Cyanide Hydratase Network Analysis

by Narges Malmir, Mohammadreza Zamani, Mostafa Motallebi, Najaf Allahyari Fard and Lukhanyo Mekuto

Molecules 2022, 27(10), 3336; https://doi.org/10.3390/molecules27103336 - 23 May 2022

Cited by 5 | Viewed by 1991

Abstract

Cyanide is a poisonous and dangerous chemical that binds to metals in metalloenzymes, especially cytochrome C oxidase and, thus, interferes with their functionalities. Different pathways and enzymes are involved during cyanide biodegradation, and cyanide hydratase is one of the enzymes that is involved in such a process. In this study, cyanide resistance and cyanide degradation were studied using 24 fungal strains in order to find the strain with the best capacity for cyanide bioremediation. To confirm the capacity of the tested strains, cyano-bioremediation and the presence of the gene that is responsible for the cyanide detoxification was assessed. From the tested organisms, Trichoderma harzianum (T. harzianum) had a significant capability to resist and degrade cyanide at a 15 mM concentration, where it achieved an efficiency of 75% in 7 days. The gene network analysis of enzymes that are involved in cyanide degradation revealed the involvement of cyanide hydratase, dipeptidase, carbon–nitrogen hydrolase-like protein, and ATP adenylyltransferase. This study revealed that T. harzianum was more efficient in degrading cyanide than the other tested fungal organisms, and molecular analysis confirmed the experimental observations. Full article

(This article belongs to the Special Issue Molecules in 2022)

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15 pages, 3660 KiB

Open AccessArticle

Solubility and Permeability Enhancement of Oleanolic Acid by Solid Dispersion in Poloxamers and γ-CD

by Chiara De Stefani, Jessika Lodovichi, Laura Albonetti, Maria Cristina Salvatici, José Carlos Quintela, Anna Rita Bilia and Maria Camilla Bergonzi

Molecules 2022, 27(9), 3042; https://doi.org/10.3390/molecules27093042 - 09 May 2022

Cited by 5 | Viewed by 2962

Abstract

Oleanolic acid (OA) is a pentacyclic triterpenoid widely found in the Oleaceae family, and it represents 3.5% of the dry weight of olive leaves. OA has many pharmacological activities, such as hepatoprotection, anti-inflammatory, anti-oxidant, anti-diabetic, anti-tumor, and anti-microbic activities. Its therapeutic application is limited by its poor water solubility, bioavailability, and permeability. In this study, solid dispersions (SDs) were developed to overcome these OA limitations. Solubility studies were conducted to evaluate different hydrophilic polymers, drug-to-polymer ratios, and preparation methods. Poloxamer 188, Poloxamer 407, and γ-CD exhibited the highest increases in terms of OA solubility, regardless of the method of preparation. Binary systems were characterized using differential scanning calorimetry (DSC), X-ray diffraction (XRPD), and Fourier transform infrared spectroscopy (FTIR). In addition, pure compounds and SDs were analyzed using scanning electron microscopy (SEM) in order to observe both the morphology and the particle surface. In vitro dissolution studies were performed for P407, P188, and γ-CD SDs. Preparation using the solvent evaporation method (SEM) produced the highest increase in the dissolution profiles of all three polymers with respect to the OA solution. Finally, the effect of SDs on OA permeability was evaluated with an in vitro parallel artificial membrane permeability assay (PAMPA). The formulation improved passive permeation across the simulated barrier due to OA increased solubility. The dissolution and PAMPA results indicate that the amorphization of OA by SD preparation could be a useful method to enhance its oral absorption, and it is also applicable on an industrial scale. Full article

(This article belongs to the Special Issue Molecules in 2022)

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21 pages, 6056 KiB

Open AccessArticle

Gas Sensors Based on Porous Ceramic Bodies of MSnO₃ Perovskites (M = Ba, Ca, Zn): Formation and Sensing Properties towards Ethanol, Acetone, and Toluene Vapours

by Yasser H. Ochoa-Muñoz, Ruby Mejía de Gutiérrez, Jorge E. Rodríguez-Páez, Isabel Gràcia and Stella Vallejos

Molecules 2022, 27(9), 2889; https://doi.org/10.3390/molecules27092889 - 30 Apr 2022

Cited by 6 | Viewed by 2202

Abstract

In this work, the gas-sensing functionality of porous ceramic bodies formed by the slip casting technique was studied using perovskite nanoparticles of an MSnO₃ system (M = Ba, Ca, Zn) synthesized by a chemical route. The performance and reliability of the sensitive materials in the presence of different volatile organic compounds (acetone, ethanol, and toluene), and other gases (CO, H₂ and NO₂) were analysed. The ZnSnO₃, BaSnO₃, and CaSnO₃ sensors showed sensitivities of 40, 16, and 8% ppm⁻¹ towards acetone, ethanol, and toluene vapours, respectively. Good repeatability and selectivity were also observed for these gaseous analytes, as well as excellent stability for a period of 120 days. The shortest response times were recorded for the ZnSnO₃ sensors (e.g., 4 s for 80 ppm acetone) with marked responses to low concentrations of acetone (1000 ppb). These results are attributed to the porosity of the sensitive materials, which favours the diffusion of gases, induces surface defects, and provides greater surface area and good sensitivity to acetone, as is seen in the case of ZnSnO₃. Full article

(This article belongs to the Special Issue Molecules in 2022)

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15 pages, 1586 KiB

Open AccessArticle

Lymph Nodes Draining Infections Investigated by PET and Immunohistochemistry in a Juvenile Porcine Model

by Pia Afzelius, Malene Kjelin Morsing, Ole Lerberg Nielsen, Aage Kristian Olsen Alstrup, Svend Borup Jensen and Lars Jødal

Molecules 2022, 27(9), 2792; https://doi.org/10.3390/molecules27092792 - 27 Apr 2022

Cited by 1 | Viewed by 2602

Abstract

Background: [¹⁸F]FDG and [¹¹C]methionine accumulate in lymph nodes draining S. aureus -infected foci. The lymph nodes were characterized by weight, [¹¹C]methionine- and [¹⁸F]FDG-positron emissions tomography (PET)/computed tomography (CT), and immunohistochemical (IHC)-staining. Methods: 20 pigs inoculated with S. aureus into the right femoral artery were PET/CT-scanned with [¹⁸F]FDG, and nine of the pigs were additionally scanned with [¹¹C]methionine. Mammary, medial iliac, and popliteal lymph nodes from the left and right hind limbs were weighed. IHC-staining for calculations of area fractions of Ki-67, L1, and IL-8 positive cells was done in mammary and popliteal lymph nodes from the nine pigs. Results: The pigs developed one to six osteomyelitis foci. Some pigs developed contiguous infections of peri-osseous tissue and inoculation-site abscesses. Weights of mammary and medial iliac lymph nodes and their [¹⁸F]FDG maximum Standardized Uptake Values (SUV_FDGmax) showed a significant increase in the inoculated limb compared to the left limb. Popliteal lymph node weight and their FDG uptake did not differ significantly between hind limbs. Area fractions of Ki-67 and IL-8 in the right mammary lymph nodes and SUV_Metmax in the right popliteal lymph nodes were significantly increased compared with the left side. Conclusion: The PET-tracers [¹⁸F]FDG and [¹¹C]methionine, and the IHC- markers Ki-67 and IL-8, but not L1, showed increased values in lymph nodes draining soft tissues infected with S. aureus. The increase in [¹¹C]methionine may indicate a more acute lymph node response, whereas an increase in [¹⁸F]FDG may indicate a more chronic response. Full article

(This article belongs to the Special Issue Molecules in 2022)

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22 pages, 2644 KiB

Open AccessArticle

Secondary Metabolism Rearrangements in Linum usitatissimum L. after Biostimulation of Roots with COS Oligosaccharides from Fungal Cell Wall

by Redouan Elboutachfaiti, Roland Molinié, David Mathiron, Yannis Maillot, Jean-Xavier Fontaine, Serge Pilard, Anthony Quéro, Clément Brasselet, Marguerite Dols-Lafargue, Cédric Delattre and Emmanuel Petit

Molecules 2022, 27(7), 2372; https://doi.org/10.3390/molecules27072372 - 06 Apr 2022

Cited by 5 | Viewed by 2657

Abstract

In vitro culture of flax (Linum usitatissimum L.) was exposed to chitosan oligosaccharides (COS) in order to investigate the effects on the growth and secondary metabolites content in roots and shoots. COS are fragments of chitosan released from the fungal cell wall during plant–pathogen interactions. They can be perceived by the plant as pathogen-associated signals, mediating local and systemic innate immune responses. In the present study, we report a novel COS oligosaccharide fraction with a degree of polymerization (DP) range of 2–10, which was produced from fungal chitosan by a thermal degradation method and purified by an alcohol-precipitation process. COS was dissolved in hydroponic medium at two different concentrations (250 and 500 mg/L) and applied to the roots of growing flax seedlings. Our observations indicated that the growth of roots and shoots decreased markedly in COS-treated flax seedlings compared to the control. In addition, the results of a metabolomics analysis showed that COS treatment induced the accumulation of (neo)lignans locally at roots, flavones luteolin C-glycosides, and chlorogenic acid in systemic responses in the shoots of flax seedlings. These phenolic compounds have been previously reported to exhibit a strong antioxidant and antimicrobial activities. COS oligosaccharides, under the conditions applied in this study (high dose treatment with a much longer exposure time), can be used to indirectly trigger metabolic response modifications in planta, especially secondary metabolism, because during fungal pathogen attack, COS oligosaccharides are among the signals exchanged between the pathogen and host plant. Full article

(This article belongs to the Special Issue Molecules in 2022)

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12 pages, 3505 KiB

Open AccessArticle

Intermolecular Halogen Bond Detected in Racemic and Optically Pure N-C Axially Chiral 3-(2-Halophenyl)quinazoline-4-thione Derivatives

by Ryosuke Matsui, Erina Niijima, Tomomi Imai, Hiroyuki Kobayashi, Akiko Hori, Azusa Sato, Yuko Nakamura and Osamu Kitagawa

Molecules 2022, 27(7), 2369; https://doi.org/10.3390/molecules27072369 - 06 Apr 2022

Cited by 3 | Viewed by 2211

Abstract

The halogen bond has been widely used as an important supramolecular tool in various research areas. However, there are relatively few studies on halogen bonding related to molecular chirality. 3-(2-Halophenyl)quinazoline-4-thione derivatives have stable atropisomeric structures due to the rotational restriction around an N-C single bond. In X-ray single crystal structures of the racemic and optically pure N-C axially chiral quinazoline-4-thiones, we found that different types of intermolecular halogen bonds (C=S⋯X) are formed. That is, in the racemic crystals, the intermolecular halogen bond between the ortho-halogen atom and sulfur atom was found to be oriented in a periplanar conformation toward the thiocarbonyl plane, leading to a syndiotactic zig-zag array. On the other hand, the halogen bond in the enantiomerically pure crystals was oriented orthogonally toward the thiocarbonyl plane, resulting in the formation of a homochiral dimer. These results indicate that the corresponding racemic and optically pure forms in chiral molecules are expected to display different halogen bonding properties, respectively, and should be separately studied as different chemical entities. Full article

(This article belongs to the Special Issue Molecules in 2022)

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19 pages, 2946 KiB

Open AccessArticle

NMR, LC-MS Characterization of Rydingia michauxii Extracts, Identification of Natural Products Acting as Modulators of LDLR and PCSK9

by Stefania Sut, Aminallah Tahmasebi, Nicola Ferri, Irene Ferrarese, Ilaria Rossi, Giovanni Panighel, Maria Giovanna Lupo, Filippo Maggi, Akbar Karami and Stefano Dall’Acqua

Molecules 2022, 27(7), 2256; https://doi.org/10.3390/molecules27072256 - 30 Mar 2022

Cited by 2 | Viewed by 2590

Abstract

Rydingia michauxii (Briq.) Scheen and V.A.Albert (Lamiaceae) is used in Iranian traditional medicine to treat malaria, diabetes, hyperlipidemia, rheumatism and cardiovascular diseases. NMR and LC-DAD-MSⁿ analyses were used to establish extract composition and phenylethanoid, flavonoid glycosides, lignans, labdane diterpenes and iridoids were identified and quantified. The main constituents were isolated, and structures were elucidated based on NMR, polarimetric and MS measurements. A new natural compound, ent-labda-8(17),13-dien-18-glucopyranosyl ester-15,16-olide is described here. The effects of ent-labda-8(17),13-dien-18-oic acid-15,16-olide (1), ent-labda-8(17),13-dien-18-glucopyranosyl es-ter-15,16-olide (2), antirrhinoside (3), echinacoside (4), verbascoside (5), and apigenin 6,8-di-C-glucoside (6), on the low-density lipoprotein receptor (LDLR) and proprotein convertase subtilisin/kexin type 9 (PCSK9), were studied in the human hepatocarcinoma cell line Huh7. Among the six constituents, (3) showed the strongest induction of the LDLR (3.7 ± 2.2 fold vs. control) and PCSK9 (3.2 ± 1.5 fold vs. control) at a concentration of 50 µM. The in vitro observations indicated a potential lipid lowering activity of (3) with a statin-like mechanism of action. Full article

(This article belongs to the Special Issue Molecules in 2022)

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12 pages, 3727 KiB

Open AccessArticle

Determination of Methyl Methanesulfonate and Ethyl Methylsulfonate in New Drug for the Treatment of Fatty Liver Using Derivatization Followed by High-Performance Liquid Chromatography with Ultraviolet Detection

by Yue Wang, Jing Feng, Song Wu, Huihui Shao, Wenxuan Zhang, Kun Zhang, Hanyilan Zhang and Qingyun Yang

Molecules 2022, 27(6), 1950; https://doi.org/10.3390/molecules27061950 - 17 Mar 2022

Cited by 4 | Viewed by 2539

Abstract

A new derivatization high-performance liquid chromatography method with ultraviolet detection was developed and validated for the quantitative analysis of methanesulfonate genotoxic impurities in an innovative drug for the treatment of non-alcoholic fatty liver disease. In this study, sodium dibenzyldithiocarbamate was used as a derivatization reagent for the first time to enhance the sensitivity of the analysis, and NaOH aqueous solution was chosen as a pH regulator to avoid the interference of the drug matrix. Several key experimental parameters of the derivatization reaction were investigated and optimized. In addition, specificity, linearity, precision, stability, and accuracy were validated. The determined results of the samples were consistent with those obtained from the derivatization gas chromatography–mass spectrometry analysis. Thus, the proposed method is a reliable and practical protocol for the determination of trace methanesulfonate genotoxic impurities in drugs containing mesylate groups. Full article

(This article belongs to the Special Issue Molecules in 2022)

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15 pages, 2326 KiB

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CO₂ to CO Electroreduction, Electrocatalytic H₂ Evolution, and Catalytic Degradation of Organic Dyes Using a Co(II) meso-Tetraarylporphyrin

by Mouhieddinne Guergueb, Frédérique Loiseau, Florian Molton, Habib Nasri and Axel Klein

Molecules 2022, 27(5), 1705; https://doi.org/10.3390/molecules27051705 - 05 Mar 2022

Cited by 4 | Viewed by 2155

Abstract

The meso-tetrakis(4-(trifluoromethyl)phenyl)porphyrinato cobalt(II) complex [Co(TMFPP)] was synthesised in 93% yield. The compound was studied by ¹H NMR, UV-visible absorption, and photoluminescence spectroscopy. The optical band gap Eg was calculated to 2.15 eV using the Tauc plot method and a semiconducting character is suggested. Cyclic voltammetry showed two fully reversible reduction waves at E_1/2 = −0.91 V and E_1/2 = −2.05 V vs. SCE and reversible oxidations at 0.30 V and 0.98 V representing both metal-centred (Co(0)/Co(I)/Co(II)/Co(III)) and porphyrin-centred (Por²⁻/Por⁻) processes. [Co(TMFPP)] is a very active catalyst for the electrochemical formation of H₂ from DMF/acetic acid, with a Faradaic Efficiency (FE) of 85%, and also catalysed the reduction of CO₂ to CO with a FE of 90%. Moreover, the two triarylmethane dyes crystal violet and malachite green were decomposed using H₂O₂ and [Co(TMFPP)] as catalyst with an efficiency of more than 85% in one batch. Full article

(This article belongs to the Special Issue Molecules in 2022)

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