Next Issue
Volume 26, June-1
Previous Issue
Volume 26, May-1
 
 
molecules-logo

Journal Browser

Journal Browser

Molecules, Volume 26, Issue 10 (May-2 2021) – 230 articles

Cover Story (view full-size image): Metal–organic frameworks (MOFs) encompass a rapidly expanding class of materials with diverse potential applications that underpin energy storage and energy conversion systems, molecular separation or sensing. In this account, a collaborative team from Trinity College Dublin describes the synthesis of two-dimensional Cu-porphyrin-based MOFs. The compounds are composed of extended one-dimensional, rod-based secondary building units containing either Mn(II) or Co(II) centers. The structural attributes make these compound types promising materials for future photocatalytic investigations, including bio-inspired water oxidation catalysis. View this paper
  • Issues are regarded as officially published after their release is announced to the table of contents alert mailing list.
  • You may sign up for e-mail alerts to receive table of contents of newly released issues.
  • PDF is the official format for papers published in both, html and pdf forms. To view the papers in pdf format, click on the "PDF Full-text" link, and use the free Adobe Reader to open them.
Order results
Result details
Section
Select all
Export citation of selected articles as:
18 pages, 3235 KiB  
Article
Bioactive Co(II), Ni(II), and Cu(II) Complexes Containing a Tridentate Sulfathiazole-Based (ONN) Schiff Base
by Aurora Reiss, Nicoleta Cioateră, Aurelian Dobrițescu, Mihaela Rotaru, Alice Carla Carabet, Filippo Parisi, Anca Gănescu, Irina Dăbuleanu, Cezar Ionuț Spînu and Petre Rotaru
Molecules 2021, 26(10), 3062; https://doi.org/10.3390/molecules26103062 - 20 May 2021
Cited by 23 | Viewed by 3307
Abstract
New Co(II), Ni(II), and Cu(II) complexes were synthesized with the Schiff base ligand obtained by the condensation of sulfathiazole with salicylaldehyde. Their characterization was performed by elemental analysis, molar conductance, spectroscopic techniques (IR, diffuse reflectance and UV–Vis–NIR), magnetic moments, thermal analysis, and calorimetry [...] Read more.
New Co(II), Ni(II), and Cu(II) complexes were synthesized with the Schiff base ligand obtained by the condensation of sulfathiazole with salicylaldehyde. Their characterization was performed by elemental analysis, molar conductance, spectroscopic techniques (IR, diffuse reflectance and UV–Vis–NIR), magnetic moments, thermal analysis, and calorimetry (thermogravimetry/derivative thermogravimetry/differential scanning calorimetry), while their morphological and crystal systems were explained on the basis of powder X-ray diffraction results. The IR data indicated that the Schiff base ligand is tridentate coordinated to the metallic ion with two N atoms from azomethine group and thiazole ring and one O atom from phenolic group. The composition of the complexes was found to be of the [ML2]∙nH2O (M = Co, n = 1.5 (1); M = Ni, n = 1 (2); M = Cu, n = 4.5 (3)) type, having an octahedral geometry for the Co(II) and Ni(II) complexes and a tetragonally distorted octahedral geometry for the Cu(II) complex. The presence of lattice water molecules was confirmed by thermal analysis. XRD analysis evidenced the polycrystalline nature of the powders, with a monoclinic structure. The unit cell volume of the complexes was found to increase in the order of (2) < (1) < (3). SEM evidenced hard agglomerates with micrometric-range sizes for all the investigated samples (ligand and complexes). EDS analysis showed that the N:S and N:M atomic ratios were close to the theoretical ones (1.5 and 6.0, respectively). The geometric and electronic structures of the Schiff base ligand 4-((2-hydroxybenzylidene) amino)-N-(thiazol-2-yl) benzenesulfonamide (HL) was computationally investigated by the density functional theory (DFT) method. The predictive molecular properties of the chemical reactivity of the HL and Cu(II) complex were determined by a DFT calculation. The Schiff base and its metal complexes were tested against some bacterial strains (Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, and Bacillus subtilis). The results indicated that the antibacterial activity of all metal complexes is better than that of the Schiff base. Full article
(This article belongs to the Special Issue New Trends in Developing Complexes as Biological Active Species)
Show Figures

Figure 1

42 pages, 440 KiB  
Review
Secondary Metabolites from Artemisia Genus as Biopesticides and Innovative Nano-Based Application Strategies
by Bianca Ivănescu, Ana Flavia Burlec, Florina Crivoi, Crăița Roșu and Andreia Corciovă
Molecules 2021, 26(10), 3061; https://doi.org/10.3390/molecules26103061 - 20 May 2021
Cited by 36 | Viewed by 5195
Abstract
The Artemisia genus includes a large number of species with worldwide distribution and diverse chemical composition. The secondary metabolites of Artemisia species have numerous applications in the health, cosmetics, and food sectors. Moreover, many compounds of this genus are known for their antimicrobial, [...] Read more.
The Artemisia genus includes a large number of species with worldwide distribution and diverse chemical composition. The secondary metabolites of Artemisia species have numerous applications in the health, cosmetics, and food sectors. Moreover, many compounds of this genus are known for their antimicrobial, insecticidal, parasiticidal, and phytotoxic properties, which recommend them as possible biological control agents against plant pests. This paper aims to evaluate the latest available information related to the pesticidal properties of Artemisia compounds and extracts and their potential use in crop protection. Another aspect discussed in this review is the use of nanotechnology as a valuable trend for obtaining pesticides. Nanoparticles, nanoemulsions, and nanocapsules represent a more efficient method of biopesticide delivery with increased stability and potency, reduced toxicity, and extended duration of action. Given the negative impact of synthetic pesticides on human health and on the environment, Artemisia-derived biopesticides and their nanoformulations emerge as promising ecofriendly alternatives to pest management. Full article
(This article belongs to the Special Issue Natural Secondary Metabolites II)
22 pages, 3099 KiB  
Article
Modeling Adsorption and Optical Properties for the Design of CO2 Photocatalytic Metal-Organic Frameworks
by Priscila Chacón, Joseelyne G. Hernández-Lima, Adán Bazán-Jiménez and Marco A. García-Revilla
Molecules 2021, 26(10), 3060; https://doi.org/10.3390/molecules26103060 - 20 May 2021
Cited by 4 | Viewed by 2708
Abstract
Four Metal-Organic Frameworks (MOFs) were modeled (IRMOF-C-BF2, IRMOF-C-(2)-BF2, IRMOF-C’-BF2, and IRMOF-C-CH2BF2) based on IRMOF-1. A series of linkers, based on Frustrated Lewis Pairs and coumarin moieties, were attached to IRMOF-1 to obtain MOFs [...] Read more.
Four Metal-Organic Frameworks (MOFs) were modeled (IRMOF-C-BF2, IRMOF-C-(2)-BF2, IRMOF-C’-BF2, and IRMOF-C-CH2BF2) based on IRMOF-1. A series of linkers, based on Frustrated Lewis Pairs and coumarin moieties, were attached to IRMOF-1 to obtain MOFs with photocatalytic properties. Four different linkers were used: (a) a BF2 attached to a coumarin moiety at position 3, (b) two BF2 attached to a coumarin moiety in positions 3 and 7, (c) a BF2 attached in the coumarin moiety at position 7, and (d) a CH2BF2 attached at position 3. An analysis of the adsorption properties of H2, CO2, H2O and possible CO2 photocatalytic capabilities was performed by means of computational modeling using Density Functional Theory (DFT), Time-Dependent Density Functional (TD-DFT) methods, and periodic quantum chemical wave function approach. The results show that the proposed linkers are good enough to improve the CO2 adsorption, to hold better bulk properties, and obtain satisfactory optical properties in comparison with IRMOF-1 by itself. Full article
Show Figures

Figure 1

23 pages, 6575 KiB  
Article
Ligand-Dependent Conformational Transitions in Molecular Dynamics Trajectories of GPCRs Revealed by a New Machine Learning Rare Event Detection Protocol
by Ambrose Plante and Harel Weinstein
Molecules 2021, 26(10), 3059; https://doi.org/10.3390/molecules26103059 - 20 May 2021
Cited by 6 | Viewed by 2887
Abstract
Central among the tools and approaches used for ligand discovery and design are Molecular Dynamics (MD) simulations, which follow the dynamic changes in molecular structure in response to the environmental condition, interactions with other proteins, and the effects of ligand binding. The need [...] Read more.
Central among the tools and approaches used for ligand discovery and design are Molecular Dynamics (MD) simulations, which follow the dynamic changes in molecular structure in response to the environmental condition, interactions with other proteins, and the effects of ligand binding. The need for, and successes of, MD simulations in providing this type of essential information are well documented, but so are the challenges presented by the size of the resulting datasets encoding the desired information. The difficulty of extracting information on mechanistically important state-to-state transitions in response to ligand binding and other interactions is compounded by these being rare events in the MD trajectories of complex molecular machines, such as G-protein-coupled receptors (GPCRs). To address this problem, we have developed a protocol for the efficient detection of such events. We show that the novel Rare Event Detection (RED) protocol reveals functionally relevant and pharmacologically discriminating responses to the binding of different ligands to the 5-HT2AR orthosteric site in terms of clearly defined, structurally coherent, and temporally ordered conformational transitions. This information from the RED protocol offers new insights into specific ligand-determined functional mechanisms encoded in the MD trajectories, which opens a new and rigorously reproducible path to understanding drug activity with application in drug discovery. Full article
Show Figures

Figure 1

15 pages, 4143 KiB  
Article
Functionalized Hydroperoxide Formation from the Reaction of Methacrolein-Oxide, an Isoprene-Derived Criegee Intermediate, with Formic Acid: Experiment and Theory
by Michael F. Vansco, Kristen Zuraski, Frank A. F. Winiberg, Kendrew Au, Nisalak Trongsiriwat, Patrick J. Walsh, David L. Osborn, Carl J. Percival, Stephen J. Klippenstein, Craig A. Taatjes, Marsha I. Lester and Rebecca L. Caravan
Molecules 2021, 26(10), 3058; https://doi.org/10.3390/molecules26103058 - 20 May 2021
Cited by 16 | Viewed by 2828
Abstract
Methacrolein oxide (MACR-oxide) is a four-carbon, resonance-stabilized Criegee intermediate produced from isoprene ozonolysis, yet its reactivity is not well understood. This study identifies the functionalized hydroperoxide species, 1-hydroperoxy-2-methylallyl formate (HPMAF), generated from the reaction of MACR-oxide with formic acid using multiplexed photoionization mass [...] Read more.
Methacrolein oxide (MACR-oxide) is a four-carbon, resonance-stabilized Criegee intermediate produced from isoprene ozonolysis, yet its reactivity is not well understood. This study identifies the functionalized hydroperoxide species, 1-hydroperoxy-2-methylallyl formate (HPMAF), generated from the reaction of MACR-oxide with formic acid using multiplexed photoionization mass spectrometry (MPIMS, 298 K = 25 °C, 10 torr = 13.3 hPa). Electronic structure calculations indicate the reaction proceeds via an energetically favorable 1,4-addition mechanism. The formation of HPMAF is observed by the rapid appearance of a fragment ion at m/z 99, consistent with the proposed mechanism and characteristic loss of HO2 upon photoionization of functional hydroperoxides. The identification of HPMAF is confirmed by comparison of the appearance energy of the fragment ion with theoretical predictions of its photoionization threshold. The results are compared to analogous studies on the reaction of formic acid with methyl vinyl ketone oxide (MVK-oxide), the other four-carbon Criegee intermediate in isoprene ozonolysis. Full article
Show Figures

Graphical abstract

15 pages, 7302 KiB  
Article
Synthesis and Anticancer Activity Evaluation of 5-[2-Chloro-3-(4-nitrophenyl)-2-propenylidene]-4-thiazolidinones
by Kamila Buzun, Anna Kryshchyshyn-Dylevych, Julia Senkiv, Olexandra Roman, Andrzej Gzella, Krzysztof Bielawski, Anna Bielawska and Roman Lesyk
Molecules 2021, 26(10), 3057; https://doi.org/10.3390/molecules26103057 - 20 May 2021
Cited by 13 | Viewed by 2495
Abstract
A series of novel 5-[(Z,2Z)-2-chloro-3-(4-nitrophenyl)-2-propenylidene]-thiazolidinones (Ciminalum–thiazolidinone hybrid molecules) have been synthesized. Anticancer activity screening toward the NCI60 cell lines panel, gastric cancer (AGS), human colon cancer (DLD-1), and breast cancer (MCF-7 and MDA-MB-231) cell lines allowed the identification of [...] Read more.
A series of novel 5-[(Z,2Z)-2-chloro-3-(4-nitrophenyl)-2-propenylidene]-thiazolidinones (Ciminalum–thiazolidinone hybrid molecules) have been synthesized. Anticancer activity screening toward the NCI60 cell lines panel, gastric cancer (AGS), human colon cancer (DLD-1), and breast cancer (MCF-7 and MDA-MB-231) cell lines allowed the identification of 3-{5-[(Z,2Z)-2-chloro-3-(4-nitrophenyl)-2-propenylidene]-4-oxo-2-thioxothiazolidin-3-yl}propanoic acid (2h) with the highest level of antimitotic activity with mean GI50/TGI values of 1.57/13.3 μM and a certain sensitivity profile against leukemia (MOLT-4, SR), colon cancer (SW-620), CNS cancer (SF-539), melanoma (SK-MEL-5), gastric cancer (AGS), human colon cancer (DLD-1), and breast cancers (MCF-7 and MDA-MB-231) cell lines. The hit compounds 2f, 2i, 2j, and 2h have been found to have low toxicity toward normal human blood lymphocytes and a fairly wide therapeutic range. The significant role of the 2-chloro-3-(4-nitrophenyl)prop-2-enylidene (Ciminalum) substituent in the 5 position and the substituent’s nature in the position 3 of core heterocycle in the anticancer cytotoxicity levels of 4-thiazolidinone derivatives have been established Full article
Show Figures

Graphical abstract

11 pages, 2794 KiB  
Article
Inherently Area-Selective Atomic Layer Deposition of Manganese Oxide through Electronegativity-Induced Adsorption
by Yi-Cheng Li, Kun Cao, Yu-Xiao Lan, Jing-Ming Zhang, Miao Gong, Yan-Wei Wen, Bin Shan and Rong Chen
Molecules 2021, 26(10), 3056; https://doi.org/10.3390/molecules26103056 - 20 May 2021
Cited by 7 | Viewed by 3605
Abstract
Manganese oxide (MnOx) shows great potential in the areas of nano-electronics, magnetic devices and so on. Since the characteristics of precise thickness control at the atomic level and self-align lateral patterning, area-selective deposition (ASD) of the MnOx films can be [...] Read more.
Manganese oxide (MnOx) shows great potential in the areas of nano-electronics, magnetic devices and so on. Since the characteristics of precise thickness control at the atomic level and self-align lateral patterning, area-selective deposition (ASD) of the MnOx films can be used in some key steps of nanomanufacturing. In this work, MnOx films are deposited on Pt, Cu and SiO2 substrates using Mn(EtCp)2 and H2O over a temperature range of 80–215 °C. Inherently area-selective atomic layer deposition (ALD) of MnOx is successfully achieved on metal/SiO2 patterns. The selectivity improves with increasing deposition temperature within the ALD window. Moreover, it is demonstrated that with the decrease of electronegativity differences between M (M = Si, Cu and Pt) and O, the chemisorption energy barrier decreases, which affects the initial nucleation rate. The inherent ASD aroused by the electronegativity differences shows a possible method for further development and prediction of ASD processes. Full article
(This article belongs to the Special Issue Self-Assembled Materials and Bottom-Up Fabrication)
Show Figures

Graphical abstract

19 pages, 2766 KiB  
Article
Evaluation of Aphicidal Effect of Essential Oils and Their Synergistic Effect against Myzus persicae (Sulzer) (Hemiptera: Aphididae)
by Qasim Ahmed, Manjree Agarwal, Ruaa Al-Obaidi, Penghao Wang and Yonglin Ren
Molecules 2021, 26(10), 3055; https://doi.org/10.3390/molecules26103055 - 20 May 2021
Cited by 20 | Viewed by 2704
Abstract
The insecticidal activities of essential oils obtained from black pepper, eucalyptus, rosemary, and tea tree and their binary combinations were investigated against the green peach aphid, Myzus persicae (Aphididae: Hemiptera), under laboratory and glasshouse conditions. All the tested essential oils significantly reduced and [...] Read more.
The insecticidal activities of essential oils obtained from black pepper, eucalyptus, rosemary, and tea tree and their binary combinations were investigated against the green peach aphid, Myzus persicae (Aphididae: Hemiptera), under laboratory and glasshouse conditions. All the tested essential oils significantly reduced and controlled the green peach aphid population and caused higher mortality. In this study, black pepper and tea tree pure essential oils were found to be an effective insecticide, with 80% mortality when used through contact application. However, for combinations of essential oils from black pepper + tea tree (BT) and rosemary + tea tree (RT) tested as contact treatment, the mortality was 98.33%. The essential oil combinations exhibited synergistic and additive interactions for insecticidal activities. The combination of black pepper + tea tree, eucalyptus + tea tree (ET), and tea tree + rosemary showed enhanced activity, with synergy rates of 3.24, 2.65, and 2.74, respectively. Essential oils formulation was effective on the mortality of aphids. Fourier Transform Infrared Spectroscopy (FTIR) analysis showed that stability of a mixture of essential oils was not affected by store temperature (15, 25, and 35 °C) and the functional groups were not changed during storage. Based on our results, the essential oils can be used as a commercial insecticide against M. persicae. Full article
Show Figures

Figure 1

15 pages, 2349 KiB  
Article
Identification of the Active Principle Conferring Anti-Inflammatory and Antinociceptive Properties in Bamboo Plant
by Bruna Araujo Sousa, Osmar Nascimento Silva, William Farias Porto, Thales Lima Rocha, Luciano Paulino Silva, Ana Paula Ferreira Leal, Danieli Fernanda Buccini, James Oluwagbamigbe Fajemiroye, Ruy de Araujo Caldas, Octávio Luiz Franco, Maria Fátima Grossi-de-Sá, Cesar de la Fuente Nunez and Susana Elisa Moreno
Molecules 2021, 26(10), 3054; https://doi.org/10.3390/molecules26103054 - 20 May 2021
Viewed by 2759
Abstract
Early plants began colonizing earth about 450 million years ago. During the process of coevolution, their metabolic cellular pathways produced a myriad of natural chemicals, many of which remain uncharacterized biologically. Popular preparations containing some of these molecules have been used medicinally for [...] Read more.
Early plants began colonizing earth about 450 million years ago. During the process of coevolution, their metabolic cellular pathways produced a myriad of natural chemicals, many of which remain uncharacterized biologically. Popular preparations containing some of these molecules have been used medicinally for thousands of years. In Brazilian folk medicine, plant extracts from the bamboo plant Guadua paniculata Munro have been used for the treatment of infections and pain. However, the chemical basis of these therapeutic effects has not yet been identified. Here, we performed protein biochemistry and downstream pharmacological assays to determine the mechanisms underlying the anti-inflammatory and antinociceptive effects of an aqueous extract of the G. paniculata rhizome, which we termed AqGP. The anti-inflammatory and antinociceptive effects of AqGP were assessed in mice. We identified and purified a protein (AgGP), with an amino acid sequence similar to that of thaumatins (~20 kDa), capable of repressing inflammation through downregulation of neutrophil recruitment and of decreasing hyperalgesia in mice. In conclusion, we have identified the molecule and the molecular mechanism responsible for the anti-inflammatory and antinociceptive properties of a plant commonly used in Brazilian folk medicine. Full article
(This article belongs to the Special Issue Natural Product-Inspired Molecules: From Weed to Remedy)
Show Figures

Graphical abstract

13 pages, 2722 KiB  
Article
TAK1/AP-1-Targeted Anti-Inflammatory Effects of Barringtonia augusta Methanol Extract
by Anh Thu Ha, Mi-Yeon Kim and Jae Youl Cho
Molecules 2021, 26(10), 3053; https://doi.org/10.3390/molecules26103053 - 20 May 2021
Cited by 6 | Viewed by 2953
Abstract
Barringtonia augusta methanol extract (Ba-ME) is a folk medicine found in the wetlands of Thailand that acts through an anti-inflammatory mechanism that is not understood fully. Here, we examine how the methanol extract of Barringtonia augusta (B. augusta) can suppress the activator [...] Read more.
Barringtonia augusta methanol extract (Ba-ME) is a folk medicine found in the wetlands of Thailand that acts through an anti-inflammatory mechanism that is not understood fully. Here, we examine how the methanol extract of Barringtonia augusta (B. augusta) can suppress the activator protein 1 (AP-1) signaling pathway and study the activities of Ba-ME in the lipopolysaccharide (LPS)-treated RAW264.7 macrophage cell line and an LPS-induced peritonitis mouse model. Non-toxic concentrations of Ba-ME downregulated the mRNA expression of cytokines, such as cyclooxygenase and chemokine ligand 12, in LPS-stimulated RAW264.7 cells. Transfection experiments with the AP-1-Luc construct, HEK293T cells, and luciferase assays were used to assess whether Ba-ME suppressed the AP-1 functional activation. A Western blot assay confirmed that C-Jun N-terminal kinase is a direct pharmacological target of Ba-ME action. The anti-inflammatory effect of Ba-ME, which functions by β-activated kinase 1 (TAK1) inhibition, was confirmed by using an overexpression strategy and a cellular thermal shift assay. In vivo experiments in a mouse model of LPS-induced peritonitis showed the anti-inflammatory effect of Ba-ME on LPS-stimulated macrophages and acute inflammatory mouse models. We conclude that Ba-ME is a promising anti-inflammatory drug targeting TAK1 in the AP-1 pathway. Full article
(This article belongs to the Special Issue Plant Extracts: Immunomodulatory and Anti-cancer Properties)
Show Figures

Figure 1

16 pages, 4729 KiB  
Article
Synthetic Iowaite Can Effectively Remove Inorganic Arsenic from Marine Extract
by Jing Ji, Wenwen Huang, Lingchong Wang, Lu Chen, Yuanqing Wei, Rui Liu, Jianming Cheng and Hao Wu
Molecules 2021, 26(10), 3052; https://doi.org/10.3390/molecules26103052 - 20 May 2021
Cited by 1 | Viewed by 1640
Abstract
For the removal of arsenic from marine products, iowaite was prepared and investigated to determine the optimal adsorption process of arsenic. Different chemical forms of arsenic (As(III), As(V)) with varying concentrations (0.15, 1.5, 5, 10, 15, and 20 mg/L) under various conditions including [...] Read more.
For the removal of arsenic from marine products, iowaite was prepared and investigated to determine the optimal adsorption process of arsenic. Different chemical forms of arsenic (As(III), As(V)) with varying concentrations (0.15, 1.5, 5, 10, 15, and 20 mg/L) under various conditions including pH (3, 5, 7, 9, 11) and contact time (1, 2, 5, 10, 15, 30, 60, 120, 180 min) were exposed to iowaite. Adsorption isotherms and metal ions kinetic modeling onto the adsorbent were determined based on Langmuir, Freundlich, first- and second-order kinetic models. The adsorption onto iowaite varied depending on the conditions. The adsorption rates of standard solution, As(III) and As(V) exceeded 95% under proper conditions, while high complexity was noted with marine samples. As(III) and As(V) from Mactra veneriformis extraction all decreased when exposed to iowaite. The inclusion morphology and interconversion of organic arsenic limit adsorption. Iowaite can be efficiently used for inorganic arsenic removal from wastewater and different marine food products, which maybe other adsorbent or further performance of iowaite needs to be investigated for organic arsenic. Full article
(This article belongs to the Special Issue Advanced Materials in Environmental Chemistry)
Show Figures

Graphical abstract

10 pages, 2722 KiB  
Article
Lead Levels in Non-Occupationally Exposed Women with Preeclampsia
by Katarzyna Gajewska, Marzena Laskowska, Agostinho Almeida, Edgar Pinto, Katarzyna Skórzyńska-Dziduszko and Anna Błażewicz
Molecules 2021, 26(10), 3051; https://doi.org/10.3390/molecules26103051 - 20 May 2021
Cited by 6 | Viewed by 2168
Abstract
There are many controversies regarding the relationship between lead exposure andcomplications in pregnancy. Preeclampsia (PE) is a maternal hypertensive disorder which is one of the main causes of maternal and foetal mortality. The aim of our study was to assess blood lead level [...] Read more.
There are many controversies regarding the relationship between lead exposure andcomplications in pregnancy. Preeclampsia (PE) is a maternal hypertensive disorder which is one of the main causes of maternal and foetal mortality. The aim of our study was to assess blood lead level (BLL) in Polish women with PE (PE group, n = 66) compared with healthy, non-pregnant women (CNP group, n = 40) and healthy pregnant women (CP group, n = 40). BLL was determined by inductively coupled plasma mass spectrometry (ICP-MS). The systolic blood pressure (SBP), diastolic blood pressure (DBP) and BLL in the CP group were significantly lower than in the PE group (p < 0.001). Logistic regression analyses of BLL showed a significant positive relationship with the presence of PE. Furthermore, both the SBP and DBP values were positively associated with BLL. This study indicates that preeclamptic women tend to present with significantly higher BLL compared to healthy pregnant women. There were no differences in the BLL between the CP and CNP groups. Full article
Show Figures

Figure 1

11 pages, 1167 KiB  
Article
Stable Bicyclic Functionalized Nitroxides: The Synthesis of Derivatives of Aza-nortropinone–5-Methyl-3-oxo-6,8-diazabicyclo[3.2.1]-6-octene 8-oxyls
by Larisa N. Grigor’eva, Alexsei Ya. Tikhonov, Konstantin A. Lomanovich and Dmitrii G. Mazhukin
Molecules 2021, 26(10), 3050; https://doi.org/10.3390/molecules26103050 - 20 May 2021
Cited by 1 | Viewed by 1880
Abstract
In recent decades, bicyclic nitroxyl radicals have caught chemists’ attention as selective catalysts for the oxidation of alcohols and amines and as additives and mediators in directed C-H oxidative transformations. In this regard, the design and development of synthetic approaches to new functional [...] Read more.
In recent decades, bicyclic nitroxyl radicals have caught chemists’ attention as selective catalysts for the oxidation of alcohols and amines and as additives and mediators in directed C-H oxidative transformations. In this regard, the design and development of synthetic approaches to new functional bicyclic nitroxides is a relevant and important issue. It has been reported that imidazo[1,2-b]isoxazoles formed during the condensation of acetylacetone with 2-hydroxyaminooximes having a secondary hydroxyamino group are recyclized under mild basic catalyzed conditions to 8-hydroxy-5-methyl-3-oxo-6,8-diazabicyclo[3.2.1]-6-octenes. The latter, containing a sterically hindered cyclic N-hydroxy group, upon oxidation with lead dioxide in acetone, virtually quantitatively form stable nitroxyl bicyclic radicals of a new class, which are derivatives of both 2,2,6,6-tetramethyl-4-oxopiperidine-1-oxyl (TEMPON) and 3-imidazolines. Full article
Show Figures

Graphical abstract

12 pages, 781 KiB  
Article
Chemical Profiling and Antimicrobial Properties of Honey Bee (Apis mellifera L.) Venom
by Irina Tanuwidjaja, Lidija Svečnjak, Domenika Gugić, Marko Levanić, Slaven Jurić, Marko Vinceković and Mirna Mrkonjić Fuka
Molecules 2021, 26(10), 3049; https://doi.org/10.3390/molecules26103049 - 20 May 2021
Cited by 13 | Viewed by 4064
Abstract
The incidence of antibiotic resistance in pathogenic bacteria has become an alarming clinical and social problem. Therefore, the demand for alternative antimicrobial compounds has increased. In this study, a chemical profile of honey bee (Apis mellifera L.) venom (HBV) has been determined [...] Read more.
The incidence of antibiotic resistance in pathogenic bacteria has become an alarming clinical and social problem. Therefore, the demand for alternative antimicrobial compounds has increased. In this study, a chemical profile of honey bee (Apis mellifera L.) venom (HBV) has been determined by HPLC and FTIR-ATR spectroscopy, and tested for antibacterial activity, as well as efficiency with regard to conventional antibiotics. The investigated HBV was of high quality with melittin and total protein contents of 70.10 ± 7.01%, and 84.44 ± 3.12 g/100 g, respectively. The purity of HBV was confirmed by FTIR-ATR spectral profiling, which revealed a unique pattern of absorption bands that are characteristic of its major fractions. In addition, HBV showed a broad spectrum of activity against all three tested biomasses of potentially pathogenic Gram-positive and Gram-negative bacteria with MIC values ranging between 12.5 and 200 µg/mL, and MBC between 12.5 and 400 µg/mL. When compared to conventional antibiotics, HBV (400 µg) showed up to 27.8% efficiency of tetracycline (30 µg), 52.2% erythromycin (15 µg), 21.2% ciprofloxacin (5 µg), and 34.6% of ampicillin-sulbactam (20 µg). The overall results demonstrate the therapeutic potential of the analyzed HBV. Full article
(This article belongs to the Special Issue Bee Products: Recent Progress in Health Benefits Studies)
Show Figures

Figure 1

14 pages, 390 KiB  
Article
Characterization of the Key Aroma-Active Compounds in Yongchuan Douchi (Fermented Soybean) by Application of the Sensomics Approach
by Shuqi Wang, Yuan Chang, Bing Liu, Haitao Chen, Baoguo Sun and Ning Zhang
Molecules 2021, 26(10), 3048; https://doi.org/10.3390/molecules26103048 - 20 May 2021
Cited by 21 | Viewed by 2743
Abstract
Yongchuan douchi is a traditional fermented soya bean product which is popular in Chinese dishes due to its unique flavor. In this study, the key aroma-active compounds of Yongchuan douchi were characterized by the combined gas chromatography–olfactometry (GC–O) and gas chromatography−mass spectrometry (GC–MS) [...] Read more.
Yongchuan douchi is a traditional fermented soya bean product which is popular in Chinese dishes due to its unique flavor. In this study, the key aroma-active compounds of Yongchuan douchi were characterized by the combined gas chromatography–olfactometry (GC–O) and gas chromatography−mass spectrometry (GC–MS) with sensory evaluation. In total, 49 aroma compounds were sniffed and identified, and 20 of them with high flavor dilution factors (FD) and odor activity values (OAVs) greater than one were screened by applied aroma extract dilution analysis (AEDA) and quantitated analysis. Finally, aroma recombination and omission experiments were performed and 10 aroma-active compounds were thought to have contributed significantly including 2,3-butanedione (butter, cheese), dimethyl trisulfide (garlic-like), acetic acid (pungent sour), acetylpyrazine (popcorn-like), 3-methylvaleric acid (sweaty), 4-methylvaleric acid (sweaty), 2-mehoxyphenol (smoky), maltol (caramel), γ-nonanolactone (coconut-like), eugenol (woody) and phenylacetic acid (flora). In addition, sensory evaluation showed that the flavor profile of Yongchuan douchi mainly consisted of sauce-like, sour, nutty, smoky, caramel and fruity notes. Full article
(This article belongs to the Section Applied Chemistry)
Show Figures

Figure 1

15 pages, 2583 KiB  
Article
Synthesis of the [11]Cyclacene Framework by Repetitive Diels–Alder Cycloadditions
by John B. Bauer, Fatima Diab, Cäcilia Maichle-Mössmer, Hartmut Schubert and Holger F. Bettinger
Molecules 2021, 26(10), 3047; https://doi.org/10.3390/molecules26103047 - 20 May 2021
Cited by 1 | Viewed by 2516
Abstract
The Diels–Alder cycloaddition between bisdienes and bisdienophile incorporating the 7-oxa-bicyclo[2.2.1]heptane unit are well known to show high diastereoselectivity that can be exploited for the synthesis of molecular belts. The related bisdiene 5,6,7,8-tetramethylidene-2-bicyclo[2.2.2]octene is a valuable building block for the synthesis of photoprecursors for [...] Read more.
The Diels–Alder cycloaddition between bisdienes and bisdienophile incorporating the 7-oxa-bicyclo[2.2.1]heptane unit are well known to show high diastereoselectivity that can be exploited for the synthesis of molecular belts. The related bisdiene 5,6,7,8-tetramethylidene-2-bicyclo[2.2.2]octene is a valuable building block for the synthesis of photoprecursors for acenes, but it has not been employed for the synthesis of molecular belts. The present work investigates by computational means the Diels–Alder reaction between these bisdiene building blocks with syn-1,4,5,8-tetrahydro-1,4:5,8-diepoxyanthracene, which shows that the diastereoselectivity of the Diels–Alder reaction of the etheno-bridged bisdiene is lower than that of the epoxy-bridged bisdiene. The reaction of the etheno-bridged bisdiene and syn-1,4,5,8-tetrahydro-1,4:5,8-diepoxyanthracene in 2:1 ratio yields two diastereomers that differ in the orientation of the oxa and etheno bridges based on NMR and X-ray crystallography. The all-syn diastereomer can be transformed into a molecular belt by inter- and intramolecular Diels–Alder reactions with a bifunctional building block. The molecular belt could function as a synthetic intermediate en route to a [11]cyclacene photoprecursor. Full article
(This article belongs to the Special Issue Diels-Alder Reaction in Organic Synthesis)
Show Figures

Graphical abstract

21 pages, 3524 KiB  
Article
Aloe djiboutiensis: Antioxidant Activity, Molecular Networking-Based Approach and In Vivo Toxicity of This Endemic Species in Djibouti
by Abdirahman Elmi, Fatouma Mohamed Abdoul-Latif, Rosella Spina, François Dupire, Stéphanie Philippot, Champy Marie-France, Hugues Jacobs and Dominique Laurain-Mattar
Molecules 2021, 26(10), 3046; https://doi.org/10.3390/molecules26103046 - 20 May 2021
Cited by 3 | Viewed by 5524
Abstract
For the first time, the study of the antioxidant activity, the characterization of the phytoconstituants, and the evaluation of in vitro and in vivo toxicity of A. djiboutiensis leave and latex are performed. The antioxidant activity of both latex (ADL) and the methanolic [...] Read more.
For the first time, the study of the antioxidant activity, the characterization of the phytoconstituants, and the evaluation of in vitro and in vivo toxicity of A. djiboutiensis leave and latex are performed. The antioxidant activity of both latex (ADL) and the methanolic extract of leaves (ADM) is determined using 1-diphenyl-2-picrylhydrazyl (DPPH), 2,2′-azino-bis 3-ethylbenzothiazoline-6-sulphonic acid (ABTS) scavenging radical methods and ferric reducing/antioxidant power (FRAP) assay. The phytochemical study of latex is done using Liquid Chromatography-Mass Spectrometry (LC-MS/MS) and a molecular networking-based approach. The evaluation of in vivo toxicity is performed on mice by oral gavage with a suspension of ADL. Our results show that weak antioxidant activity of ADL and ADM in opposition to their high polyphenol, 83.01 mg and 46.4 mg expressed in gallic acid equivalent (GAE)/g of dry weight (DW), respectively, and flavonoid contents 13.12 mg and 4.25 mg expressed in quercetin equivalent (QE)/g dry weight (DW), respectively. Using the Global Natural Products Social Molecular Networking (GNPS) website, nine (9) anthraquinones derivatives, ten (10) chromones derivatives, two (2) flavonols/ chromones isomers are annotated in the molecular network. The treated mice do not display abnormalities in their general physical appearance and biochemistry parameters, compared to the controls. Only glucose and calcium levels are slightly higher in male treated mice compared to the vehicles. Full article
(This article belongs to the Special Issue Antioxidants in Plant Sciences)
Show Figures

Figure 1

26 pages, 6260 KiB  
Article
Effect of Saffron Extract on the Hepatotoxicity Induced by Copper Nanoparticles in Male Mice
by Azza A. Attia, Heba S. Ramdan, Rasha A. Al-Eisa, Bassant O. A. Adle Fadle and Nahla S. El-Shenawy
Molecules 2021, 26(10), 3045; https://doi.org/10.3390/molecules26103045 - 20 May 2021
Cited by 6 | Viewed by 2382
Abstract
Background: Nanotechnology application has widespread use in many products. Copper nanoparticles (CuNPs) are widely used in industrial applications. The present study was conducted to investigate the effect of the ethanolic saffron extract (ESE) as a natural antioxidant on the hepatotoxicity induced by CuNPs [...] Read more.
Background: Nanotechnology application has widespread use in many products. Copper nanoparticles (CuNPs) are widely used in industrial applications. The present study was conducted to investigate the effect of the ethanolic saffron extract (ESE) as a natural antioxidant on the hepatotoxicity induced by CuNPs in male mice. Methods: The characterization of CuNPs was determined using ultraviolet–visible absorption spectroscopy, particle size analysis, zeta potential, Fourier-transform infrared spectroscopy, and electron microscope. The effect of saffron on the hepatotoxicity induced by CuNPs in mice was evaluated by evaluating the survival rate of the mice, oxidative stress, antioxidant capacity, DNA evaluation, as well as its effect on the histology and transmission electron microscope of the liver. Results: The results revealed that all parameters were affected in a dose-dependent manner by CuNPs. These effects have been improved when the treatment of CuNPs is combined with ethanolic saffron extract. Conclusions: We can conclude that saffron and its bioactive crocin portion can prevent CuNP-induced oxidative liver damage. This substance should be useful as a new pharmacological tool for oxidative stress prevention. Full article
Show Figures

Figure 1

23 pages, 6988 KiB  
Article
Ribes nigrum Leaf Extract Preferentially Inhibits IFN-γ-Mediated Inflammation in HaCaT Keratinocytes
by Andrea Magnavacca, Stefano Piazza, Anna Cammisa, Marco Fumagalli, Giulia Martinelli, Flavio Giavarini, Enrico Sangiovanni and Mario Dell’Agli
Molecules 2021, 26(10), 3044; https://doi.org/10.3390/molecules26103044 - 20 May 2021
Cited by 5 | Viewed by 2921
Abstract
Ribes nigrum L. (blackcurrant) leaf extracts, due to high levels of flavonols and anthocyanins, have been shown to exhibit beneficial effects in inflammatory diseases. However, whereas their traditional use has been investigated and validated in several models of inflammation and oxidative stress, the [...] Read more.
Ribes nigrum L. (blackcurrant) leaf extracts, due to high levels of flavonols and anthocyanins, have been shown to exhibit beneficial effects in inflammatory diseases. However, whereas their traditional use has been investigated and validated in several models of inflammation and oxidative stress, the possible impact on skin disorders is still largely unknown. The purpose of this work was to elucidate the effects of R. nigrum leaf extract (RNLE) on keratinocyte-derived inflammatory mediators, elicited by a Th1 or Th2 cytokine milieu. HaCaT cells were challenged with TNF-α, either alone or in combination with the costimulatory cytokines IFN-γ or IL-4, and the release of proinflammatory cytokines and mediators (IL-8, IL-6, s-ICAM-1, and TSLP) was evaluated. The results showed that RNLE preferentially interferes with IFN-γ signaling, demonstrating only negligible activity on TNF-α or IL-4. This effect was attributed to flavonols, which might also account for the ability of RNLE to impair TNF-α/IL-4-induced TSLP release in a cAMP-independent manner. These results suggest that RNLE could have an antiallergic effect mediated in keratinocytes via mechanisms beyond histamine involvement. In conclusion, the discovery of RNLE preferential activity against IFN-γ-mediated inflammation suggests potential selectivity against Th1 type response and the possible use in Th1 inflammatory diseases. Full article
(This article belongs to the Special Issue Bioactive Compounds for Cosmeceuticals against Skin Diseases)
Show Figures

Figure 1

18 pages, 1724 KiB  
Article
Synthesis and α-Glucosidase Inhibition Activity of 2-[3-(Benzoyl/4-bromobenzoyl)-4-hydroxy-1,1-dioxido-2H-benzo[e][1,2]thiazin-2-yl]-N-arylacetamides: An In Silico and Biochemical Approach
by Furqan Ahmad Saddique, Sana Aslam, Matloob Ahmad, Usman Ali Ashfaq, Muhammad Muddassar, Sadia Sultan, Saman Taj, Muzammil Hussain, Dae Sung Lee and Magdi E. A. Zaki
Molecules 2021, 26(10), 3043; https://doi.org/10.3390/molecules26103043 - 20 May 2021
Cited by 15 | Viewed by 2494
Abstract
Diabetes mellitus (DM) is a chronic disorder and has affected a large number of people worldwide. Insufficient insulin production causes an increase in blood glucose level that results in DM. To lower the blood glucose level, various drugs are employed that block the [...] Read more.
Diabetes mellitus (DM) is a chronic disorder and has affected a large number of people worldwide. Insufficient insulin production causes an increase in blood glucose level that results in DM. To lower the blood glucose level, various drugs are employed that block the activity of the α-glucosidase enzyme, which is considered responsible for the breakdown of polysaccharides into monosaccharides leading to an increase in the intestinal blood glucose level. We have synthesized novel 2-(3-(benzoyl/4-bromobenzoyl)-4-hydroxy-1,1-dioxido-2H-benzo[e][1,2]thiazin-2-yl)-N-arylacetamides and have screened them for their in silico and in vitro α-glucosidase inhibition activity. The derivatives 11c, 12a, 12d, 12e, and 12g emerged as potent inhibitors of the α-glucosidase enzyme. These compounds exhibited good docking scores and excellent binding interactions with the selected residues (Asp203, Asp542, Asp327, His600, Arg526) during in silico screening. Similarly, these compounds also showed good in vitro α-glucosidase inhibitions with IC50 values of 30.65, 18.25, 20.76, 35.14, and 24.24 μM, respectively, which were better than the standard drug, acarbose (IC50 = 58.8 μM). Furthermore, a good agreement was observed between in silico and in vitro modes of study. Full article
(This article belongs to the Section Bioorganic Chemistry)
Show Figures

Graphical abstract

28 pages, 2165 KiB  
Review
Bioactive Components of Salvia and Their Potential Antidiabetic Properties: A Review
by Aswir Abd Rashed and Devi-Nair Gunasegavan Rathi
Molecules 2021, 26(10), 3042; https://doi.org/10.3390/molecules26103042 - 20 May 2021
Cited by 19 | Viewed by 3736
Abstract
The utilization of therapeutic plants is expanding around the globe, coupled with the tremendous expansion of alternative medicine and growing demand in health treatment. Plants are applied in pharmaceuticals to preserve and expand health—physically, mentally and as well as to treat particular health [...] Read more.
The utilization of therapeutic plants is expanding around the globe, coupled with the tremendous expansion of alternative medicine and growing demand in health treatment. Plants are applied in pharmaceuticals to preserve and expand health—physically, mentally and as well as to treat particular health conditions and afflictions. There are more than 600 families of plants identified so far. Among the plants that are often studied for their health benefit include the genus of Salvia in the mint family, Lamiaceae. This review aims to determine the bioactive components of Salvia and their potential as antidiabetic agents. The search was conducted using three databases (PubMed, EMBASE and Scopus), and all relevant articles that are freely available in the English language were extracted within 10 years (2011–2021). Salvia spp. comprises many biologically active components that can be divided into monoterpenes, diterpenes, triterpenes, and phenolic components, but only a few of these have been studied in-depth for their health benefit claims. The most commonly studied bioactive component was salvianolic acids. Interestingly, S. miltiorrhiza is undoubtedly the most widely studied Salvia species in terms of its effectiveness as an antidiabetic agent. In conclusion, we hope that this review stimulates more studies on bioactive components from medicinal plants, not only on their potential as antidiabetic agents but also for other possible health benefits. Full article
(This article belongs to the Special Issue Bioactive Compounds on Health and Disease)
Show Figures

Figure 1

14 pages, 7751 KiB  
Article
Design, Synthesis, and Antitumor Activity of Olmutinib Derivatives Containing Acrylamide Moiety
by Xiaohan Hu, Sheng Tang, Feiyi Yang, Pengwu Zheng, Shan Xu, Qingshan Pan and Wufu Zhu
Molecules 2021, 26(10), 3041; https://doi.org/10.3390/molecules26103041 - 20 May 2021
Cited by 7 | Viewed by 2371
Abstract
Two series of olmutinib derivatives containing an acrylamide moiety were designed and synthesized, and their IC50 values against cancer cell lines (A549, H1975, NCI-H460, LO2, and MCF-7) were evaluated. Most of the compounds exhibited moderate cytotoxic activity against the five cancer cell [...] Read more.
Two series of olmutinib derivatives containing an acrylamide moiety were designed and synthesized, and their IC50 values against cancer cell lines (A549, H1975, NCI-H460, LO2, and MCF-7) were evaluated. Most of the compounds exhibited moderate cytotoxic activity against the five cancer cell lines. The most promising compound, H10, showed not only excellent activity against EGFR kinase but also positive biological activity against PI3K kinase. The structure–activity relationship (SAR) suggested that the introduction of dimethylamine scaffolds with smaller spatial structures was more favorable for antitumor activity. Additionally, the substitution of different acrylamide side chains had different effects on the activity of compounds. Generally, compounds H7 and H10 were confirmed as promising antitumor agents. Full article
Show Figures

Graphical abstract

21 pages, 6727 KiB  
Article
The Phytochemical Analysis of Vinca L. Species Leaf Extracts Is Correlated with the Antioxidant, Antibacterial, and Antitumor Effects
by Alexandra Ciorîță, Cezara Zăgrean-Tuza, Augustin C. Moț, Rahela Carpa and Marcel Pârvu
Molecules 2021, 26(10), 3040; https://doi.org/10.3390/molecules26103040 - 19 May 2021
Cited by 11 | Viewed by 3998
Abstract
The phytochemical analysis of Vinca minor, V. herbacea, V. major, and V. major var. variegata leaf extracts showed species-dependent antioxidant, antibacterial, and cytotoxic effects correlated with the identified phytoconstituents. Vincamine was present in V. minor, V. major, and [...] Read more.
The phytochemical analysis of Vinca minor, V. herbacea, V. major, and V. major var. variegata leaf extracts showed species-dependent antioxidant, antibacterial, and cytotoxic effects correlated with the identified phytoconstituents. Vincamine was present in V. minor, V. major, and V. major var. variegata, while V. minor had the richest alkaloid content, followed by V. herbacea. V. major var. variegata was richest in flavonoids and the highest total phenolic content was found in V. herbacea which also had elevated levels of rutin. Consequently, V. herbacea had the highest antioxidant activity followed by V. major var. variegata. Whereas, the lowest one was of V. major. The V. minor extract showed the most efficient inhibitory effect against both Staphylococcusaureus and E. coli. On the other hand, V. herbacea had a good anti-bacterial potential only against S. aureus, which was most affected at morphological levels, as indicated by scanning electron microscopy. The Vinca extracts acted in a dose-depended manner against HaCaT keratinocytes and A375 melanoma cells and moreover, with effects on the ultrastructure, nitric oxide concentration, and lactate dehydrogenase release. Therefore, the Vinca species could be exploited further for the development of alternative treatments in bacterial infections or as anticancer adjuvants. Full article
(This article belongs to the Special Issue Plant Extracts: Technologies, Characterizations and Applications)
Show Figures

Graphical abstract

18 pages, 5606 KiB  
Article
Influence of Gas Supply Changes on the Formation Process of Complex Mixed Gas Hydrates
by Mengdi Pan and Judith M. Schicks
Molecules 2021, 26(10), 3039; https://doi.org/10.3390/molecules26103039 - 19 May 2021
Cited by 5 | Viewed by 2072
Abstract
Natural gas hydrate occurrences contain predominantly methane; however, there are increasing reports of complex mixed gas hydrates and coexisting hydrate phases. Changes in the feed gas composition due to the preferred incorporation of certain components into the hydrate phase and an inadequate gas [...] Read more.
Natural gas hydrate occurrences contain predominantly methane; however, there are increasing reports of complex mixed gas hydrates and coexisting hydrate phases. Changes in the feed gas composition due to the preferred incorporation of certain components into the hydrate phase and an inadequate gas supply is often assumed to be the cause of coexisting hydrate phases. This could also be the case for the gas hydrate system in Qilian Mountain permafrost (QMP), which is mainly controlled by pores and fractures with complex gas compositions. This study is dedicated to the experimental investigations on the formation process of mixed gas hydrates based on the reservoir conditions in QMP. Hydrates were synthesized from water and a gas mixture under different gas supply conditions to study the effects on the hydrate formation process. In situ Raman spectroscopic measurements and microscopic observations were applied to record changes in both gas and hydrate phase over the whole formation process. The results demonstrated the effects of gas flow on the composition of the resulting hydrate phase, indicating a competitive enclathration of guest molecules into the hydrate lattice depending on their properties. Another observation was that despite significant changes in the gas composition, no coexisting hydrate phases were formed. Full article
(This article belongs to the Special Issue Gas Hydrates: Formation, Structures, and Properties)
Show Figures

Graphical abstract

14 pages, 2448 KiB  
Review
Chemistry and Pharmacological Activity of Sesquiterpenoids from the Chrysanthemum Genus
by Sai Jiang, Mengyun Wang, Zichen Jiang, Salman Zafar, Qian Xie, Yupei Yang, Yang Liu, Hanwen Yuan, Yuqing Jian and Wei Wang
Molecules 2021, 26(10), 3038; https://doi.org/10.3390/molecules26103038 - 19 May 2021
Cited by 13 | Viewed by 3451
Abstract
Plants from the Chrysanthemum genus are rich sources of chemical diversity and, in recent years, have been the focus of research on natural products chemistry. Sesquiterpenoids are one of the major classes of chemical constituents reported from this genus. To date, more than [...] Read more.
Plants from the Chrysanthemum genus are rich sources of chemical diversity and, in recent years, have been the focus of research on natural products chemistry. Sesquiterpenoids are one of the major classes of chemical constituents reported from this genus. To date, more than 135 sesquiterpenoids have been isolated and identified from the whole genus. These include 26 germacrane-type, 26 eudesmane-type, 64 guaianolide-type, 4 bisabolane-type, and 15 other-type sesquiterpenoids. Pharmacological studies have proven the biological potential of sesquiterpenoids isolated from Chrysanthemum species, reporting anti-inflammatory, antibacterial, antitumor, insecticidal, and antiviral activities for these interesting molecules. In this paper, we provide information on the chemistry and bioactivity of sesquiterpenoids obtained from the Chrysanthemum genus which could be used as the scientific basis for their future development and utilization. Full article
Show Figures

Graphical abstract

11 pages, 1660 KiB  
Article
Evaluation of Motor Coordination and Antidepressant Activities of Cinnamomum osmophloeum ct. Linalool Leaf Oil in Rodent Model
by Hui-Ting Chang, Mei-Ling Chang, Yen-Ting Chen, Shang-Tzen Chang, Fu-Lan Hsu, Chia-Chen Wu and Cheng-Kuen Ho
Molecules 2021, 26(10), 3037; https://doi.org/10.3390/molecules26103037 - 19 May 2021
Cited by 8 | Viewed by 2725
Abstract
Cinnamomum plants (Lauraceae) are a woody species native to South and Southeast Asia forests, and are widely used as food flavors and traditional medicines. This study aims to evaluate the chemical constituents of Cinnamomum osmophloeum ct. linalool leaf oil, and its antidepressant and [...] Read more.
Cinnamomum plants (Lauraceae) are a woody species native to South and Southeast Asia forests, and are widely used as food flavors and traditional medicines. This study aims to evaluate the chemical constituents of Cinnamomum osmophloeum ct. linalool leaf oil, and its antidepressant and motor coordination activities and the other behavioral evaluations in a rodent animal model. The major component of leaf oil is linalool, confirmed by GC-MS analysis. Leaf oil would not induce the extra body weight gain compared to the control mice at the examined doses after 6 weeks of oral administration. The present results provide the first evidence for motor coordination and antidepressant effects present in leaf oil. According to hypnotic, locomotor behavioral, and motor coordination evaluations, leaf oil would not cause side effects, including weight gain, drowsiness and a diminishment in the motor functions, at the examined doses. In summary, these results revealed C. osmophloeum ct. linalool leaf essential oil is of high potential as a therapeutic supplement for minor/medium depressive syndromes. Full article
(This article belongs to the Special Issue The Functional Applications of Medicinal Plants)
Show Figures

Graphical abstract

12 pages, 1888 KiB  
Article
Antiplatelet Activity of Coumarins: In Vitro Assays on COX-1
by Cristina Zaragozá, Francisco Zaragozá, Irene Gayo-Abeleira and Lucinda Villaescusa
Molecules 2021, 26(10), 3036; https://doi.org/10.3390/molecules26103036 - 19 May 2021
Cited by 8 | Viewed by 2119
Abstract
Atherosclerotic cardiovascular disease is the leading cause of death in developed countries. Therefore, there is an increasing interest in developing new potent and safe antiplatelet agents. Coumarins are a family of polyphenolic compounds with several pharmacological activities, including platelet aggregation inhibition. However, their [...] Read more.
Atherosclerotic cardiovascular disease is the leading cause of death in developed countries. Therefore, there is an increasing interest in developing new potent and safe antiplatelet agents. Coumarins are a family of polyphenolic compounds with several pharmacological activities, including platelet aggregation inhibition. However, their antiplatelet mechanism of action needs to be further elucidated. The aim of this study is to provide insight into the biochemical mechanisms involved in this activity, as well as to establish a structure–activity relationship for these compounds. With this purpose, the antiplatelet aggregation activities of coumarin, esculetin and esculin were determined in vitro in human whole blood and platelet-rich plasma, to set the potential interference with the arachidonic acid cascade. Here, the platelet COX activity was evaluated from 0.75 mM to 6.5 mM concentration by measuring the levels of metabolites derived from its activity (MDA and TXB2), together with colorimetric assays performed with the pure recombinant enzyme. Our results evidenced that the coumarin aglycones present the greatest antiplatelet activity at 5 mM and 6.5 mM on aggregometry experiments and inhibiting MDA levels. Full article
(This article belongs to the Special Issue Coumarin and Its Derivatives)
Show Figures

Figure 1

14 pages, 2190 KiB  
Article
Solvent-Free Mechanochemical Synthesis of High Transition Biphenyltetracarboxydiimide Liquid Crystals
by Jehan Y. Al-Humaidi, Siham A. Alissa, Kanubhai D. Katariya, Khulood A. Abu Al-Ola, Mohamed Hagar and Khaled D. Khalil
Molecules 2021, 26(10), 3035; https://doi.org/10.3390/molecules26103035 - 19 May 2021
Cited by 7 | Viewed by 1779
Abstract
A series of high temperature alkyl and alkoxy biphenyltetracarboxydiimide liquid crystals have been prepared under ball mill method using solvent-free mechanochemical approach. The thermal properties of the prepared compounds were investigated by deferential scanning calorimetry (DSC) measurements and the textures were identified by [...] Read more.
A series of high temperature alkyl and alkoxy biphenyltetracarboxydiimide liquid crystals have been prepared under ball mill method using solvent-free mechanochemical approach. The thermal properties of the prepared compounds were investigated by deferential scanning calorimetry (DSC) measurements and the textures were identified by polarized optical microscope (POM). The compounds showed smectic mesomorphic behaviour. The results showed the increasing nature of transition temperature Cr-SmC with chain length with increments of the SmC mesophase range. However, the mesophase range of the SmA was decreased with the terminal chain length either for the alkyl or alkoxy terminal groups. Moreover, the DFT theoretical calculations have been conducted give a detailed projection of the structure of the prepared compounds. A conformational investigation of the biphenyl part has been studied. A deep illustration of the experimental mesomorphic behaviour has been discussed in terms of the calculated aspect ratio. A projection of the frontier molecular orbitals as well as molecular electrostatic potential has been studied to show the effect of the polarity of the terminal chains on the level and the gab of the FMOs and the distribution of electrostatic charges on the prepared molecules. Full article
(This article belongs to the Special Issue Mechanochemical Synthesis of Organic Compounds)
Show Figures

Figure 1

20 pages, 2923 KiB  
Article
Design, Synthesis, and Evaluation of Dihydropyranopyrazole Derivatives as Novel PDE2 Inhibitors for the Treatment of Alzheimer’s Disease
by Yan Zhou, Jinjian Li, Han Yuan, Rui Su, Yue Huang, Yiyou Huang, Zhe Li, Yinuo Wu, Haibin Luo, Chen Zhang and Ling Huang
Molecules 2021, 26(10), 3034; https://doi.org/10.3390/molecules26103034 - 19 May 2021
Cited by 7 | Viewed by 2029
Abstract
Phosphodiesterase 2 (PDE2) has been regarded as a novel target for the treatment of Alzheimer’s disease (AD). In this study, we obtained (R)-LZ77 as a hit compound with moderate PDE2 inhibitory activity (IC50 = 261.3 nM) using a high-throughput [...] Read more.
Phosphodiesterase 2 (PDE2) has been regarded as a novel target for the treatment of Alzheimer’s disease (AD). In this study, we obtained (R)-LZ77 as a hit compound with moderate PDE2 inhibitory activity (IC50 = 261.3 nM) using a high-throughput virtual screening method based on molecular dynamics. Then, we designed and synthesized 28 dihydropyranopyrazole derivatives as PDE2 inhibitors. Among them, compound (+)-11h was the most potent PDE2 inhibitor, with an IC50 value of 41.5 nM. The molecular docking of PDE2-(+)-11h reveals that the 4-(trifluoromethyl)benzyl)oxyl side chain of the compound enters the H-pocket and forms strong hydrophobic interactions with L770/L809/F862, which improves inhibitory activity. The above results may provide insight for further structural optimization of highly potent PDE2 inhibitors and may lay the foundation for their use in the treatment of AD. Full article
(This article belongs to the Section Medicinal Chemistry)
Show Figures

Graphical abstract

13 pages, 3468 KiB  
Article
Anti-Melanogenic Properties of Velutin and Its Analogs
by Se-Hui Jung, Hee-Young Heo, Jung-Won Choe, Jaehyun Kim and Kooyeon Lee
Molecules 2021, 26(10), 3033; https://doi.org/10.3390/molecules26103033 - 19 May 2021
Cited by 4 | Viewed by 2609
Abstract
Velutin, one of the flavones contained in natural plants, has various beneficial activities, such as skin whitening, as well as anti-inflammatory, anti-allergic, antioxidant, and antimicrobial activities. However, the relationship between the structure of velutin and its anti-melanogenesis activity is not yet investigated. In [...] Read more.
Velutin, one of the flavones contained in natural plants, has various beneficial activities, such as skin whitening, as well as anti-inflammatory, anti-allergic, antioxidant, and antimicrobial activities. However, the relationship between the structure of velutin and its anti-melanogenesis activity is not yet investigated. In this study, we obtained 12 velutin derivatives substituted at C5, C7, C3′, and C4′ of the flavone backbone with hydrogen, hydroxyl, and methoxy functionalities by chemical synthesis, to perform SAR analysis of velutin structural analogues. The SAR study revealed that the substitution of functional groups at C5, C7, C3′, and C4′ of the flavone backbone affects biological activities related to melanin synthesis. The coexistence of hydroxyl and methoxy at the C5 and C7 position is essential for inhibiting tyrosinase activity. However, 1,2-diol compounds substituted at C3′ and C4′ of flavone backbone induce apoptosis of melanoma cells. Further, substitution at C3′ and C4′ with methoxy or hydrogen is essential for inhibiting melanogenesis. Thus, this study would be helpful for the development of natural-derived functional materials to regulate melanin synthesis. Full article
(This article belongs to the Special Issue Flavonoids and Their Disease Prevention and Treatment Potential 2021)
Show Figures

Figure 1

Previous Issue
Next Issue
Back to TopTop