Molecules

29 pages, 2645 KiB

Open AccessArticle

Synthesis and Biological Activity of New 7-Amino-oxazolo[5,4-d]Pyrimidine Derivatives

by Aleksandra Sochacka-Ćwikła, Andrzej Regiec, Michał Zimecki, Jolanta Artym, Ewa Zaczyńska, Maja Kocięba, Iwona Kochanowska, Iwona Bryndal, Anna Pyra and Marcin Mączyński

Molecules 2020, 25(15), 3558; https://doi.org/10.3390/molecules25153558 - 4 Aug 2020

Cited by 11 | Viewed by 5421

Abstract

The synthesis of a series of novel 7-aminooxazolo[5,4-d]pyrimidines 5, transformations during their synthesis and their physicochemical characteristics have been described. Complete detailed spectral analysis of the intermediates 2–4, the N′-cyanooxazolylacetamidine by-products 7 and final compounds 5 [...] Read more.

The synthesis of a series of novel 7-aminooxazolo[5,4-d]pyrimidines 5, transformations during their synthesis and their physicochemical characteristics have been described. Complete detailed spectral analysis of the intermediates 2–4, the N′-cyanooxazolylacetamidine by-products 7 and final compounds 5 has been carried out using MS, IR, 1D and 2D NMR spectroscopy. Theoretical research was carried out to explain the privileged formation of 7-aminooxazolo[5,4-d]pyrimidines in relation to the possibility of their isomer formation and the related thermodynamic aspects. Additionally, the single-crystal X-ray diffraction analysis for 5h was reported. Ten 7-aminooxazolo[5,4-d]pyrimidines 5 (SCM1–10) were biologically tested in vitro to preliminarily evaluate their immunological, antiviral and anticancer activity. Compounds SCM5 and SCM9 showed the best immunoregulatory profile. The compounds displayed low-toxicity and strongly inhibited phytohemagglutinin A-induced proliferation of human peripheral blood lymphocytes and lipopolysaccharide-induced proliferation of mouse splenocytes. Compound SCM9 caused also a moderate suppression of tumor necrosis factor α (TNF-α) production in a human whole blood culture. Of note, the compounds also inhibited the growth of selected tumor cell lines and inhibited replication of human herpes virus type-1 (HHV-1) virus in A-549 cell line. Molecular investigations showed that the compounds exerted differential changes in expression of signaling proteins in Jurkat and WEHI-231 cell lines. The activity of SCM5 is likely associated with elicitation of cell signaling pathways leading to cell apoptosis. The compounds may be of interest in terms of therapeutic utility as inhibitors of autoimmune disorders, virus replication and antitumor agents. Full article

(This article belongs to the Section Medicinal Chemistry)

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19 pages, 2960 KiB

Open AccessArticle

Facile Fabrication of Natural Polyelectrolyte-Nanoclay Composites: Halloysite Nanotubes, Nucleotides and DNA Study

by Svetlana Batasheva, Marina Kryuchkova, Ramil Fakhrullin, Giuseppe Cavallaro, Giuseppe Lazzara, Farida Akhatova, Läysän Nigamatzyanova, Vladimir Evtugyn, Elvira Rozhina and Rawil Fakhrullin

Molecules 2020, 25(15), 3557; https://doi.org/10.3390/molecules25153557 - 4 Aug 2020

Cited by 25 | Viewed by 4475

Abstract

Complexation of biopolymers with halloysite nanotubes (HNTs) can greatly affect their applicability as materials building blocks. Here we have performed a systematic investigation of fabrication of halloysite nanotubes complexes with nucleotides and genomic DNA. The binding of DNA and various nucleotide species (polyAU, [...] Read more.

Complexation of biopolymers with halloysite nanotubes (HNTs) can greatly affect their applicability as materials building blocks. Here we have performed a systematic investigation of fabrication of halloysite nanotubes complexes with nucleotides and genomic DNA. The binding of DNA and various nucleotide species (polyAU, UMP Na₂, ADP Na₃, dATP Na, AMP, uridine, ATP Mg) by halloysite nanotubes was tested using UV-spectroscopy. The study revealed that binding of different nucleotides to the nanoclay varied but was low both in the presence and absence of MgCl₂, while MgCl₂ facilitated significantly the binding of longer molecules such as DNA and polyAU. Modification of the nanotubes with DNA and nucleotide species was further confirmed by measurements of ζ-potentials. DNA-Mg-modified nanotubes were characterized using transmission electron (TEM), atomic force (AFM) and hyperspectral microscopies. Thermogravimetric analysis corroborated the sorption of DNA by the nanotubes, and the presence of DNA on the nanotube surface was indicated by changes in the surface adhesion force measured by AFM. DNA bound by halloysite in the presence of MgCl₂ could be partially released after addition of phosphate buffered saline. DNA binding and release from halloysite nanotubes was tested in the range of MgCl₂ concentrations (10–100 mM). Even low MgCl₂ concentrations significantly increased DNA sorption to halloysite, and the binding was leveled off at about 60 mM. DNA-Mg-modified halloysite nanotubes were used for obtaining a regular pattern on a glass surface by evaporation induced self-assembly process. The obtained spiral-like pattern was highly stable and resisted dissolution after water addition. Our results encompassing modification of non-toxic clay nanotubes with a natural polyanion DNA will find applications for construction of gene delivery vehicles and for halloysite self-assembly on various surfaces (such as skin or hair). Full article

(This article belongs to the Special Issue Recent Research Advance in the Halloysite Nanotubes Field)

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11 pages, 935 KiB

Open AccessCommunication

Far-Off Resonance: Multiwavelength Raman Spectroscopy Probing Amide Bands of Amyloid-β-(37–42) Peptide

by Martynas Talaikis, Simona Strazdaitė, Mantas Žiaunys and Gediminas Niaura

Molecules 2020, 25(15), 3556; https://doi.org/10.3390/molecules25153556 - 4 Aug 2020

Cited by 12 | Viewed by 3839

Abstract

Several neurodegenerative diseases, like Alzheimer’s and Parkinson’s are linked with protein aggregation into amyloid fibrils. Conformational changes of native protein into the β-sheet structure are associated with a significant change in the vibrational spectrum. This is especially true for amide bands which are [...] Read more.

Several neurodegenerative diseases, like Alzheimer’s and Parkinson’s are linked with protein aggregation into amyloid fibrils. Conformational changes of native protein into the β-sheet structure are associated with a significant change in the vibrational spectrum. This is especially true for amide bands which are inherently sensitive to the secondary structure of a protein. Raman amide bands are greatly intensified under resonance conditions, in the UV spectral range, allowing for the selective probing of the peptide backbone. In this work, we examine parallel β-sheet forming GGVVIA, the C-terminus segment of amyloid-β peptide, using UV–Vis, FTIR, and multiwavelength Raman spectroscopy. We find that amide bands are enhanced far from the expected UV range, i.e., at 442 nm. A reasonable two-fold relative intensity increase is observed for amide II mode (normalized according to the δCH₂/δCH₃ vibration) while comparing 442 and 633 nm excitations; an increase in relative intensity of other amide bands was also visible. The observed relative intensification of amide II, amide S, and amide III modes in the Raman spectrum recorded at 442 nm comparing with longer wavelength (633/785/830 nm) excited spectra allows unambiguous identification of amide bands in the complex Raman spectra of peptides and proteins containing the β-sheet structure. Full article

(This article belongs to the Special Issue Vibrational Spectroscopy as a Versatile Tool To Predict Protein Structure)

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24 pages, 3654 KiB

Open AccessReview

Atomic Details of Carbon-Based Nanomolecules Interacting with Proteins

by Luigi Di Costanzo and Silvano Geremia

Molecules 2020, 25(15), 3555; https://doi.org/10.3390/molecules25153555 - 4 Aug 2020

Cited by 17 | Viewed by 5086

Abstract

Since the discovery of fullerene, carbon-based nanomolecules sparked a wealth of research across biological, medical and material sciences. Understanding the interactions of these materials with biological samples at the atomic level is crucial for improving the applications of nanomolecules and address safety aspects [...] Read more.

Since the discovery of fullerene, carbon-based nanomolecules sparked a wealth of research across biological, medical and material sciences. Understanding the interactions of these materials with biological samples at the atomic level is crucial for improving the applications of nanomolecules and address safety aspects concerning their use in medicine. Protein crystallography provides the interface view between proteins and carbon-based nanomolecules. We review forefront structural studies of nanomolecules interacting with proteins and the mechanism underlying these interactions. We provide a systematic analysis of approaches used to select proteins interacting with carbon-based nanomolecules explored from the worldwide Protein Data Bank (wwPDB) and scientific literature. The analysis of van der Waals interactions from available data provides important aspects of interactions between proteins and nanomolecules with implications on functional consequences. Carbon-based nanomolecules modulate protein surface electrostatic and, by forming ordered clusters, could modify protein quaternary structures. Lessons learned from structural studies are exemplary and will guide new projects for bioimaging tools, tuning of intrinsically disordered proteins, and design assembly of precise hybrid materials. Full article

(This article belongs to the Special Issue Frontier of Protein Crystallography)

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22 pages, 3256 KiB

Open AccessArticle

Genoprotective Properties and Metabolites of β-Glucan-Rich Edible Mushrooms Following Their In Vitro Fermentation by Human Faecal Microbiota

by Athina Boulaka, Paris Christodoulou, Marigoula Vlassopoulou, Georgios Koutrotsios, Georgios Bekiaris, Georgios I. Zervakis, Evdokia K. Mitsou, Georgia Saxami, Adamantini Kyriacou, Maria Zervou, Panagiotis Georgiadis and Vasiliki Pletsa

Molecules 2020, 25(15), 3554; https://doi.org/10.3390/molecules25153554 - 4 Aug 2020

Cited by 17 | Viewed by 4322 | Correction

Abstract

A variety of bioactive compounds, constituents of edible mushrooms, in particular β-glucans, i.e., a group of β-d-glucose polysaccharides abundant in the fungal cell walls, have been linked to immunomodulating, anticancer and prebiotic activities. The aim of the study was the investigation [...] Read more.

A variety of bioactive compounds, constituents of edible mushrooms, in particular β-glucans, i.e., a group of β-d-glucose polysaccharides abundant in the fungal cell walls, have been linked to immunomodulating, anticancer and prebiotic activities. The aim of the study was the investigation of the genoprotective effects of edible mushrooms produced by Pleurotus eryngii, Pleurotus ostreatus and Cyclocybe cylindracea (Basidiomycota). Mushrooms from selected strains of the species mentioned above were fermented in vitro using faecal inocula from healthy volunteers. The cytotoxic and anti-genotoxic properties of the fermentation supernatants (FSs) were investigated in Caco-2 human colon adenocarcinoma cells. The FSs were cytotoxic in a dose-dependent manner. Non-cytotoxic concentrations were used for the genotoxicity studies, which revealed that mushrooms’ FSs have the ability to protect Caco-2 cells against tert-butyl hydroperoxide (t-BOOH), a known genotoxic agent. Their global metabolic profiling was assessed by ¹H-NMR spectroscopy. A total of 37 metabolites were identified with the use of two-dimensional (2D) homo- and hetero-nuclear NMR experiments. Multivariate data analysis monitored the metabolic variability of gut microbiota and probed to biomarkers potentially associated with the health-promoting effects of edible mushrooms. Full article

(This article belongs to the Special Issue Mushrooms:The Versatile Roles)

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13 pages, 2542 KiB

Open AccessArticle

Effects of Thymus vulgaris L., Cinnamomum verum J.Presl and Cymbopogon nardus (L.) Rendle Essential Oils in the Endotoxin-induced Acute Airway Inflammation Mouse Model

by Eszter Csikós, Kata Csekő, Amir Reza Ashraf, Ágnes Kemény, László Kereskai, Béla Kocsis, Andrea Böszörményi, Zsuzsanna Helyes and Györgyi Horváth

Molecules 2020, 25(15), 3553; https://doi.org/10.3390/molecules25153553 - 4 Aug 2020

Cited by 19 | Viewed by 4118

Abstract

Thyme (TO), cinnamon (CO), and Ceylon type lemongrass (LO) essential oils (EOs) are commonly used for inhalation. However, their effects and mechanisms on inflammatory processes are not well-documented, and the number of in vivo data that would be important to determine their potential [...] Read more.

Thyme (TO), cinnamon (CO), and Ceylon type lemongrass (LO) essential oils (EOs) are commonly used for inhalation. However, their effects and mechanisms on inflammatory processes are not well-documented, and the number of in vivo data that would be important to determine their potential benefits or risks is low. Therefore, we analyzed the chemical composition and investigated the activity of TO, CO, and LO on airway functions and inflammatory parameters in an acute pneumonitis mouse model. The components of commercially available EOs were measured by gas chromatography–mass spectrometry. Airway inflammation was induced by intratracheal endotoxin administration in mice. EOs were inhaled during the experiments. Airway function and hyperresponsiveness were determined by unrestrained whole-body plethysmography on conscious animals. Myeloperoxidase (MPO) activity was measured by spectrophotometry from lung tissue homogenates, from which semiquantitative histopathological scores were assessed. The main components of TO, CO, and LO were thymol, cinnamaldehyde, and citronellal, respectively. We provide here the first evidence that TO and CO reduce inflammatory airway hyperresponsiveness and certain cellular inflammatory parameters, so they can potentially be considered as adjuvant treatments in respiratory inflammatory conditions. In contrast, Ceylon type LO inhalation might have an irritant effect (e.g., increased airway hyperresponsiveness and MPO activity) on the inflamed airways, and therefore should be avoided. Full article

(This article belongs to the Special Issue The Therapeutic Potential of Naturally Occurring Compounds in Counteracting Oxidative Stress and Inflammation: From Basic Science to Therapy)

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14 pages, 4089 KiB

Open AccessArticle

High-Performance Cataluminescence Sensor Based on Nanosized V₂O₅ for 2-Butanone Detection

by Run-Kun Zhang, Jing-Xin Wang and Hua Cao

Molecules 2020, 25(15), 3552; https://doi.org/10.3390/molecules25153552 - 4 Aug 2020

Cited by 16 | Viewed by 3683

Abstract

The development of high-performance sensors is of great significance for the control of the volatile organic compounds (VOCs) pollution and their potential hazard. In this paper, high crystalline V₂O₅ nanoparticles were successfully synthesized by a simple hydrothermal method. The structure [...] Read more.

The development of high-performance sensors is of great significance for the control of the volatile organic compounds (VOCs) pollution and their potential hazard. In this paper, high crystalline V₂O₅ nanoparticles were successfully synthesized by a simple hydrothermal method. The structure and morphology of the prepared nanoparticles were characterized by TEM and XRD, and the cataluminescence (CTL) sensing performance was also investigated. Experiments found that the as-prepared V₂O₅ not only shows sensitive CTL response and good selectivity to 2-butanone, but also exhibits rapid response and recovery speed. The limit of detection was found to be 0.2 mg/m³ (0.07 ppm) at a signal to noise ratio of 3. In addition, the linear range exceeds two orders of magnitude, which points to the promising application of the sensor in monitoring of 2-butanone over a wide concentration range. The mechanism of the sensor exhibiting selectivity to different gas molecules were probed by quantum chemistry calculation. Results showed that the highest partial charge distribution, lowest HOMO-LUMO energy gap and largest dipole moment of 2-butanone among the tested gases result in it having the most sensitive response amongst other VOCs. Full article

(This article belongs to the Section Analytical Chemistry)

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27 pages, 20492 KiB

Open AccessArticle

Chemometric Models of Differential Amino Acids at the Na_vα and Na_vβ Interface of Mammalian Sodium Channel Isoforms

by Fernando Villa-Diaz, Susana Lopez-Nunez, Jordan E. Ruiz-Castelan, Eduardo Marcos Salinas-Stefanon and Thomas Scior

Molecules 2020, 25(15), 3551; https://doi.org/10.3390/molecules25153551 - 3 Aug 2020

Cited by 1 | Viewed by 3694

Abstract

(1) Background: voltage-gated sodium channels (Na_vs) are integral membrane proteins that allow the sodium ion flux into the excitable cells and initiate the action potential. They comprise an α (Na_vα) subunit that forms the channel pore and are coupled [...] Read more.

(1) Background: voltage-gated sodium channels (Na_vs) are integral membrane proteins that allow the sodium ion flux into the excitable cells and initiate the action potential. They comprise an α (Na_vα) subunit that forms the channel pore and are coupled to one or more auxiliary β (Na_vβ) subunits that modulate the gating to a variable extent. (2) Methods: after performing homology in silico modeling for all nine isoforms (Na_v1.1α to Na_v1.9α), the Na_vα and Na_vβ protein-protein interaction (PPI) was analyzed chemometrically based on the primary and secondary structures as well as topological or spatial mapping. (3) Results: our findings reveal a unique isoform-specific correspondence between certain segments of the extracellular loops of the Na_vα subunits. Precisely, loop S5 in domain I forms part of the PPI and assists Na_vβ1 or Na_vβ3 on all nine mammalian isoforms. The implied molecular movements resemble macroscopic springs, all of which explains published voltage sensor effects on sodium channel fast inactivation in gating. (4) Conclusions: currently, the specific functions exerted by the Na_vβ1 or Na_vβ3 subunits on the modulation of Na_vα gating remain unknown. Our work determined functional interaction in the extracellular domains on theoretical grounds and we propose a schematic model of the gating mechanism of fast channel sodium current inactivation by educated guessing. Full article

(This article belongs to the Special Issue Cheminformatics, Past, Present, and Future: From Chemistry to Nanotechnology and Complex Systems)

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13 pages, 1054 KiB

Open AccessArticle

Antidepressant Effect of Shaded White Leaf Tea Containing High Levels of Caffeine and Amino Acids

by Keiko Unno, Daisuke Furushima, Yuzuki Nomura, Hiroshi Yamada, Kazuaki Iguchi, Kyoko Taguchi, Toshikazu Suzuki, Makoto Ozeki and Yoriyuki Nakamura

Molecules 2020, 25(15), 3550; https://doi.org/10.3390/molecules25153550 - 3 Aug 2020

Cited by 13 | Viewed by 4341

Abstract

The young leaves of green tea become lighter in color than usual when protected from sunlight by a shading net for about two weeks while growing. These leaves are called “shaded white leaf tea” or SWLT. In the eluate of SWLT, the amount [...] Read more.

The young leaves of green tea become lighter in color than usual when protected from sunlight by a shading net for about two weeks while growing. These leaves are called “shaded white leaf tea” or SWLT. In the eluate of SWLT, the amount of amino acids (361 mg/L) was significantly higher than that in regular tea (53.5 mg/L). Since theanine and arginine, the first and second most abundant amino acids in SWLT, have significant antistress effects, we examined the antistress effect of SWLT on humans. SWLT or placebo green tea (3 g) was eluted with room-temperature water (500 mL). Participants consumed the tea for one week prior to pharmacy practice and continued for 10 days in the practice period. The state-trait anxiety inventory, an anxiety questionnaire, tended to be scored lower in the SWLT group than the placebo, but other stress markers showed no differences. The effect of the difference in SWLT components examined with mice showed that aspartic acid and asparagine, which are abundant in SWLT, counteracted the antistress effects of theanine and arginine. Large amounts of caffeine also interfered with SWLT’s antistress effect. Thus, SWLT, which is high in caffeine and amino acids, suppressed depressant behavior in mice. Full article

(This article belongs to the Special Issue Molecular Pharmacology of Green Tea)

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14 pages, 276 KiB

Open AccessArticle

Towards a Valorization of Corn Bioethanol Side Streams: Chemical Characterization of Post Fermentation Corn Oil and Thin Stillage

by Gabriella Di Lena, Petra Ondrejíčková, Josè Sanchez del Pulgar, Veronika Cyprichová, Tomáš Ježovič, Massimo Lucarini, Ginevra Lombardi Boccia, Stefano Ferrari Nicoli, Paolo Gabrielli, Altero Aguzzi, Irene Casini and Roberto Caproni

Molecules 2020, 25(15), 3549; https://doi.org/10.3390/molecules25153549 - 3 Aug 2020

Cited by 16 | Viewed by 4857

Abstract

First-generation biofuel biorefineries may be a starting point for the development of new value chains, as their by-products and side streams retain nutrients and valuable molecules that may be recovered and valorized for high-value applications. This study provides a chemical characterization of post-fermentation [...] Read more.

First-generation biofuel biorefineries may be a starting point for the development of new value chains, as their by-products and side streams retain nutrients and valuable molecules that may be recovered and valorized for high-value applications. This study provides a chemical characterization of post-fermentation corn oil and thin stillage, side streams of dry-grind corn bioethanol production, in view of their valorization. An overall long-term study was conducted on the two co-products collected over 1 year from a bioethanol plant. Water content, acid value, sedimentation, mineral composition, and fatty acid profiles were analyzed on post-fermentation corn oil. Results highlighted that its acid value was high (19.72–24.29 mg KOH/g), indicating high levels of free fatty acids, but stable over the year due to standardized operating conditions. The fatty acid profile was that typical of corn oil, with a prevalence of linoleic (54–59% of total fatty acids) over oleic (23–27%) and palmitic (12–17%) acids. Macronutrients, fatty acid, and mineral profiles were investigated in thin stillage. Results revealed the acidic pH (4.05–4.68) and high dilution (90–93% water) of this side stream. The dry mass was composed of fats (19–30%), proteins (8.8–12.8%), ash (8.7–9.5%), and fiber (7.3–9.8%). The concomitant presence of a variegate complex of molecules of nutritional interest in corn bioethanol co-products, with several potential high-value market applications, make the perspective of their recovery a promising strategy to create new cross-sector interconnections according to circular economy principles. Full article

(This article belongs to the Special Issue Food Sustainability: Promising By-Products for Valorization)

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12 pages, 5549 KiB

Open AccessArticle

Photochemical α-Cleavage Reaction of 3’,5’-Dimethoxybenzoin: A Combined Time-Resolved Spectroscopy and Computational Chemistry Study

by Yuanchun Li, Xiting Zhang, Zhiping Yan, Lili Du, Wenjian Tang and David Lee Phillips

Molecules 2020, 25(15), 3548; https://doi.org/10.3390/molecules25153548 - 3 Aug 2020

Cited by 1 | Viewed by 3618

Abstract

Benzoin is one of the most commonly used photoinitiators to induce free radical polymerization. Here, improved benzoin properties could be accomplished by the introduction of two methoxy substituents, leading to the formation of 3’,5’-dimethoxybenzoin (DMB) which has a higher photo-cleavage quantum yield (0.54) [...] Read more.

Benzoin is one of the most commonly used photoinitiators to induce free radical polymerization. Here, improved benzoin properties could be accomplished by the introduction of two methoxy substituents, leading to the formation of 3’,5’-dimethoxybenzoin (DMB) which has a higher photo-cleavage quantum yield (0.54) than benzoin (0.35). To elucidate the underlying reaction mechanisms of DMB and obtain direct information of the transient species involved, femtosecond transient absorption (fs-TA) and nanosecond transient absorption (ns-TA) spectroscopic experiments in conjunction with density functional theory/time-dependent density functional theory (DFT/TD-DFT) calculations were performed. It was found that the photo-induced α-cleavage (Norrish Type I reaction) of DMB occurred from the nπ* triplet state after a rapid intersystem crossing (ISC) process (7.6 ps), leading to the generation of phenyl radicals on the picosecond time scale. Compared with Benzoin, DMB possesses two methoxy groups which are able to stabilize the alcohol radical and thus result in a stronger driving force for cleavage and a higher quantum yield of photodissociation. Two stable conformations (cis-DMB and trans-DMB) at ground state were found via DFT calculations. The influence of the intramolecular hydrogen bond on the α-cleavage of DMB was elaborated. Full article

(This article belongs to the Special Issue Practical Applications of Molecular Spectroscopy)

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13 pages, 1672 KiB

Open AccessArticle

The Influence of Anthocyanidin Profile on Antileishmanial Activity of Arrabidaea chica Morphotypes

by Carla Junqueira Moragas-Tellis, Fernando Almeida-Souza, Maria do Socorro dos Santos Chagas, Paulo Victor Ramos de Souza, João Victor Silva-Silva, Ygor Jessé Ramos, Davyson de Lima Moreira, Kátia da Silva Calabrese and Maria Dutra Behrens

Molecules 2020, 25(15), 3547; https://doi.org/10.3390/molecules25153547 - 3 Aug 2020

Cited by 17 | Viewed by 3471

Abstract

Arrabidaea chica Verlot (crajiru) is a plant used in folk medicine as an astringent, anti-inflammatory, wound healing and to treat fungal and viral diseases such as measles chickenpox and herpes. Arrabidaea chica has several morphotypes recognized but little is known about its chemical [...] Read more.

Arrabidaea chica Verlot (crajiru) is a plant used in folk medicine as an astringent, anti-inflammatory, wound healing and to treat fungal and viral diseases such as measles chickenpox and herpes. Arrabidaea chica has several morphotypes recognized but little is known about its chemical variability. In the present study the anthocyanidin profile of A. chica morphotypes collected in two seasons (summer and winter) have been examined and their activity against Leishmania infection compared. High-performance liquid chromatography coupled to a diode-array detector (HPLC-DAD-UV) and by tandem mass spectrometry with electrospray ionization (ESI-MS/MS) were used for anthocyanidin separation and identification. Antileishmanial activity was measured against promastigote forms of Leishmania amazonensis. Multivariate analysis, principal component analysis (PCA) and Pearson’s correlation were performed to classify morphotypes accordingly to their anthocyanidin profile. The presence of 6,7,3′,4′-tetrahydroxy-5-methoxyflavylium (3′-hydroxy-carajurone) (1), carajurone (2), 6,7,3′-trihydroxy-5,4′-dimethoxy-flavylium (3′-hydroxy-carajurin) (3) and carajurin (4), and three unidentified anthocyanidins were detected. Two different groups were recognized: group I containing 3′-hydroxy-carajurone; and group II with high content of carajurin. Among anthocyanidins identified in the extracts, only carajurin showed significant statistical correlation (p = 0.030) with activity against L. amazonensis. Carajurin could thus be considered as a pharmacological marker for the antileishmanial potential of the species. Full article

(This article belongs to the Section Natural Products Chemistry)

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14 pages, 606 KiB

Open AccessArticle

Synthesis and Pharmacological Effects of Diosgenin–Betulinic Acid Conjugates

by Zülal Özdemir, Michaela Rybková, Martin Vlk, David Šaman, Lucie Rárová and Zdeněk Wimmer

Molecules 2020, 25(15), 3546; https://doi.org/10.3390/molecules25153546 - 3 Aug 2020

Cited by 14 | Viewed by 4225

Abstract

The target diosgenin–betulinic acid conjugates are reported to investigate their ability to enhance and modify the pharmacological effects of their components. The detailed synthetic procedure that includes copper(I)-catalyzed Huisgen 1,3-dipolar cycloaddition (click reaction), and palladium-catalyzed debenzylation by hydrogenolysis is described together with the [...] Read more.

The target diosgenin–betulinic acid conjugates are reported to investigate their ability to enhance and modify the pharmacological effects of their components. The detailed synthetic procedure that includes copper(I)-catalyzed Huisgen 1,3-dipolar cycloaddition (click reaction), and palladium-catalyzed debenzylation by hydrogenolysis is described together with the results of cytotoxicity screening tests. Palladium-catalyzed debenzylation reaction of benzyl ester intermediates was the key step in this synthetic procedure due to the simultaneous presence of a 1,4-disubstituted 1,2,3-triazole ring in the molecule that was a competing coordination site for the palladium catalyst. High pressure (130 kPa) palladium-catalyzed procedure represented a successful synthetic step yielding the required products. The conjugate 7 showed selective cytotoxicity in human T-lymphoblastic leukemia (CEM) cancer cells (IC₅₀ = 6.5 ± 1.1 µM), in contrast to the conjugate 8 showing no cytotoxicity, and diosgenin (1), an adaptogen, for which a potential to be active on central nervous system was calculated in silico. In addition, 5 showed medium multifarious cytotoxicity in human T-lymphoblastic leukemia (CEM), human cervical cancer (HeLa), and human colon cancer (HCT 116). Betulinic acid (2) and the intermediates 3 and 4 showed no cytotoxicity in the tested cancer cell lines. The experimental data obtained are supplemented by and compared with the in silico calculated physico-chemical and absorption, distribution, metabolism, and excretion (ADME) parameters of these compounds. Full article

(This article belongs to the Special Issue Saponins: From Diversity to Structural Modification and Bioactive Responses in Model Systems)

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20 pages, 1558 KiB

Open AccessArticle

Streptomyces sp. Strain MUSC 125 from Mangrove Soil in Malaysia with Anti-MRSA, Anti-Biofilm and Antioxidant Activities

by Hefa Mangzira Kemung, Loh Teng-Hern Tan, Kok-Gan Chan, Hooi-Leng Ser, Jodi Woan-Fei Law, Learn-Han Lee and Bey-Hing Goh

Molecules 2020, 25(15), 3545; https://doi.org/10.3390/molecules25153545 - 3 Aug 2020

Cited by 38 | Viewed by 6500

Abstract

There is an urgent need to search for new antibiotics to counter the growing number of antibiotic-resistant bacterial strains, one of which is methicillin-resistant Staphylococcus aureus (MRSA). Herein, we report a Streptomyces sp. strain MUSC 125 from mangrove soil in Malaysia which was [...] Read more.

There is an urgent need to search for new antibiotics to counter the growing number of antibiotic-resistant bacterial strains, one of which is methicillin-resistant Staphylococcus aureus (MRSA). Herein, we report a Streptomyces sp. strain MUSC 125 from mangrove soil in Malaysia which was identified using 16S rRNA phylogenetic and phenotypic analysis. The methanolic extract of strain MUSC 125 showed anti-MRSA, anti-biofilm and antioxidant activities. Strain MUSC 125 was further screened for the presence of secondary metabolite biosynthetic genes. Our results indicated that both polyketide synthase (pks) gene clusters, pksI and pksII, were detected in strain MUSC 125 by PCR amplification. In addition, gas chromatography-mass spectroscopy (GC-MS) detected the presence of different chemicals in the methanolic extract. Based on the GC-MS analysis, eight known compounds were detected suggesting their contribution towards the anti-MRSA and anti-biofilm activities observed. Overall, the study bolsters the potential of strain MUSC 125 as a promising source of anti-MRSA and antibiofilm compounds and warrants further investigation. Full article

(This article belongs to the Special Issue 25th Anniversary of Molecules—Recent Advances in Natural Products-2020)

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15 pages, 708 KiB

Open AccessFeature PaperArticle

The Bioaccessibility of Antioxidants in Black Currant Puree after High Hydrostatic Pressure Treatment

by Urszula Trych, Magdalena Buniowska, Sylwia Skąpska, Szymon Starzonek and Krystian Marszałek

Molecules 2020, 25(15), 3544; https://doi.org/10.3390/molecules25153544 - 3 Aug 2020

Cited by 14 | Viewed by 3929

Abstract

The aim of the study was to investigate the effect of high-pressure processing (HPP) and thermal processing (TP) on the bioaccessibility of vitamin C and anthocyanins as well as changes in the antioxidant capacity (AC) using ABTS+• and DPPH• tests on blackcurrant ( [...] Read more.

The aim of the study was to investigate the effect of high-pressure processing (HPP) and thermal processing (TP) on the bioaccessibility of vitamin C and anthocyanins as well as changes in the antioxidant capacity (AC) using ABTS+• and DPPH• tests on blackcurrant (Ribes nigrum L.) puree during the steps in the digestive process. The puree was subjected to HPP at 200, 400, and 600 MPa for 5 min (room temperature) or TP at 85 °C for 10 min. The controls were untreated puree (P) and fruit crushed in a mortar (M). All the samples were digested in a static in vitro digestion model, including the mouth, stomach, and small intestine, and subjected to dialysis. The vitamin C, anthocyanin, and antioxidant capacity were monitored at each step of the digestion process. The potential bioaccessibility of the antioxidants studied was calculated in relation to the undigested sample. TP and HPP enabled a high content of vitamin C, anthocyanins, and AC to be maintained. After simulated digestion in the small intestine, a significant decrease was observed in the vitamin C and anthocyanins (approximately 98%) content. However, a high stability (approximately 70%) of both compounds was noted at the gastric stage. HPP and TP significantly affected the potential bioaccessibility of vitamin C and anthocyanins, although the bioaccessibility of both compounds in the samples treated using HPP was higher than when using TP. Moreover, the potential bioaccessibility of vitamin C after HPP treatment (400 and 600 MPa) was higher than the bioaccessibility calculated for the M and P control samples. TP and HPP treatment negatively affected anthocyanin bioaccessibility after dialysis. The most favorable pressure was 400 MPa, as it allowed maintaining the best antioxidant activity after digestion. Full article

(This article belongs to the Special Issue Bioactive Compounds of Fruits, Vegetables and Mushrooms)

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19 pages, 5030 KiB

Open AccessArticle

Efficient Removal of Bisphenol A Using Nitrogen-Doped Graphene-Like Plates from Green Petroleum Coke

by Zhipeng Liu, Quanyong Wang, Bei Zhang, Tao Wu and Yujiang Li

Molecules 2020, 25(15), 3543; https://doi.org/10.3390/molecules25153543 - 3 Aug 2020

Cited by 7 | Viewed by 3581

Abstract

Green petroleum coke, a form of industrial waste produced in the oil-refining process, was used to synthesize nitrogen-doped graphene-like plates (N-GLPs) together with melamine. In this study, characterization and batch experiments were performed to elucidate the interaction mechanism of N-GLPs and bisphenol A [...] Read more.

Green petroleum coke, a form of industrial waste produced in the oil-refining process, was used to synthesize nitrogen-doped graphene-like plates (N-GLPs) together with melamine. In this study, characterization and batch experiments were performed to elucidate the interaction mechanism of N-GLPs and bisphenol A (BPA). Structural analysis of N-GLPs, including scanning electron microscopy (SEM), X-ray diffraction (XRD), Fourier transform infrared spectroscopy (FT-IR), Brunauer-Emmett-Teller (BET), and X-ray photoelectron spectroscopy (XPS), showed an obvious graphene-like structure and successful nitrogen doping. In addition, compared with 8.0 m²/g for green petroleum coke, the BET surface area of N-GLPs markedly increased to 96.6 m²/g. The influences of various factors, including contact time, temperature, and initial pH on BPA removal efficiency were investigated. It was found that 92.0% of BPA was successfully removed by N-GLPs at 50 °C. Based on the adsorption experiments, it was shown that electrostatic attraction, hydrogen bonding, and π-π interaction enhanced the adsorption capacity of N-GLPs for BPA. According to the thermodynamic data, the adsorption process was spontaneous, physical, and endothermic in nature. Therefore, N-GLPs are efficient adsorbent material to remove BPA from wastewater. Full article

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39 pages, 6114 KiB

Open AccessReview

Nanobioconjugates for Signal Amplification in Electrochemical Biosensing

by Sebastian Cajigas and Jahir Orozco

Molecules 2020, 25(15), 3542; https://doi.org/10.3390/molecules25153542 - 3 Aug 2020

Cited by 20 | Viewed by 4522

Abstract

Nanobioconjugates are hybrid materials that result from the coalescence of biomolecules and nanomaterials. They have emerged as a strategy to amplify the signal response in the biosensor field with the potential to enhance the sensitivity and detection limits of analytical assays. This critical [...] Read more.

Nanobioconjugates are hybrid materials that result from the coalescence of biomolecules and nanomaterials. They have emerged as a strategy to amplify the signal response in the biosensor field with the potential to enhance the sensitivity and detection limits of analytical assays. This critical review collects a myriad of strategies for the development of nanobioconjugates based on the conjugation of proteins, antibodies, carbohydrates, and DNA/RNA with noble metals, quantum dots, carbon- and magnetic-based nanomaterials, polymers, and complexes. It first discusses nanobioconjugates assembly and characterization to focus on the strategies to amplify a biorecognition event in biosensing, including molecular-, enzymatic-, and electroactive complex-based approaches. It provides some examples, current challenges, and future perspectives of nanobioconjugates for the amplification of signals in electrochemical biosensing. Full article

(This article belongs to the Special Issue Nanochemistry: Good Beginnings for a Cross-Disciplinary Platform)

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16 pages, 3955 KiB

Open AccessArticle

Sustainable Development of Enhanced Luminescence Polymer-Carbon Dots Composite Film for Rapid Cd²⁺ Removal from Wastewater

by Mohammed Abdullah Issa and Zurina Z. Abidin

Molecules 2020, 25(15), 3541; https://doi.org/10.3390/molecules25153541 - 3 Aug 2020

Cited by 27 | Viewed by 4217

Abstract

As a remedy for environmental pollution, a versatile synthetic approach has been developed to prepare polyvinyl alcohol (PVA)/nitrogen-doped carbon dots (CDs) composite film (PVA-CDs) for removal of toxic cadmium ions. The CDs were first synthesized using carboxymethylcellulose (CMC) of oil palms empty fruit [...] Read more.

As a remedy for environmental pollution, a versatile synthetic approach has been developed to prepare polyvinyl alcohol (PVA)/nitrogen-doped carbon dots (CDs) composite film (PVA-CDs) for removal of toxic cadmium ions. The CDs were first synthesized using carboxymethylcellulose (CMC) of oil palms empty fruit bunch wastes with the addition of polyethyleneimine (PEI) and then the CDs were embedded with PVA. The PVA-CDs film possess synergistic functionalities through increasing the content of hydrogen bonds for chemisorption compared to the pure CDs. Optical analysis of PVA-CDs film was performed by ultraviolet-visible and fluorescence spectroscopy. Compared to the pure CDs, the solid-state PVA-CDs displayed a bright blue color with a quantum yield (QY) of 47%; they possess excitation-independent emission and a higher Cd²⁺ removal efficiency of 91.1%. The equilibrium state was achieved within 10 min. It was found that adsorption data fit well with the pseudo-second-order kinetic and Langmuir isotherm models. The maximum adsorption uptake was 113.6 mg g⁻¹ at an optimal pH of 7. Desorption experiments showhe that adsorbent can be reused fruitfully for five adsorption-desorption cycles using 0.1 HCl elution. The film was successfully applied to real water samples with a removal efficiency of 95.34% and 90.9% for tap and drinking water, respectively. The fabricated membrane is biodegradable and its preparation follows an ecofriendly green route. Full article

(This article belongs to the Special Issue Innovative Materials and Methods for the Removal of Pollutants from the Environment)

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16 pages, 6221 KiB

Open AccessArticle

New Series of Double-Modified Colchicine Derivatives: Synthesis, Cytotoxic Effect and Molecular Docking

by Julia Krzywik, Maral Aminpour, Ewa Maj, Witold Mozga, Joanna Wietrzyk, Jack A. Tuszyński and Adam Huczyński

Molecules 2020, 25(15), 3540; https://doi.org/10.3390/molecules25153540 - 2 Aug 2020

Cited by 13 | Viewed by 5104

Abstract

Colchicine is a well-known anticancer compound showing antimitotic effect on cells. Its high cytotoxic activity against different cancer cell lines has been demonstrated many times. In this paper we report the syntheses and spectroscopic analyses of novel colchicine derivatives obtained by structural modifications [...] Read more.

Colchicine is a well-known anticancer compound showing antimitotic effect on cells. Its high cytotoxic activity against different cancer cell lines has been demonstrated many times. In this paper we report the syntheses and spectroscopic analyses of novel colchicine derivatives obtained by structural modifications at C7 (carbon-nitrogen single bond) and C10 (methylamino group) positions. All the obtained compounds have been tested in vitro to determine their cytotoxicity toward A549, MCF-7, LoVo, LoVo/DX, and BALB/3T3 cell lines. The majority of obtained derivatives exhibited higher cytotoxicity than colchicine, doxorubicin and cisplatin against the tested cancerous cell lines. Additionally, most of the presented derivatives were able to overcome the resistance of LoVo/DX cells. Additionally, their mode of binding to β-tubulin was evaluated in silico. Molecular docking studies showed that apart from the initial amides 1 and 2, compound 14, which had the best antiproliferative activity (IC₅₀ = 0.1–1.6 nM), stood out also in terms of its predicted binding energy and probably binds best into the active site of βI-tubulin isotype. Full article

(This article belongs to the Special Issue Anticancer Drug Discovery and Development)

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20 pages, 6957 KiB

Open AccessArticle

Dissolving Cellulose in 1,2,3-Triazolium- and Imidazolium-Based Ionic Liquids with Aromatic Anions

by Martin Brehm, Julian Radicke, Martin Pulst, Farzaneh Shaabani, Daniel Sebastiani and Jörg Kressler

Molecules 2020, 25(15), 3539; https://doi.org/10.3390/molecules25153539 - 2 Aug 2020

Cited by 30 | Viewed by 5870

Abstract

We present 1,2,3-triazolium- and imidazolium-based ionic liquids (ILs) with aromatic anions as a new class of cellulose solvents. The two anions in our study, benzoate and salicylate, possess a lower basicity when compared to acetate and therefore should lead to a lower amount [...] Read more.

We present 1,2,3-triazolium- and imidazolium-based ionic liquids (ILs) with aromatic anions as a new class of cellulose solvents. The two anions in our study, benzoate and salicylate, possess a lower basicity when compared to acetate and therefore should lead to a lower amount of N-heterocyclic carbenes (NHCs) in the ILs. We characterize their physicochemical properties and find that all of them are liquids at room temperature. By applying force field molecular dynamics (MD) simulations, we investigate the structure and dynamics of the liquids and find strong and long-lived hydrogen bonds, as well as significant

π

–

π

stacking between the aromatic anion and cation. Our ILs dissolve up to 8.5 wt.-% cellulose. Via NMR spectroscopy of the solution, we rule out chain degradation or derivatization, even after several weeks at elevated temperature. Based on our MD simulations, we estimate the enthalpy of solvation and derive a simple model for semi-quantitative prediction of cellulose solubility in ILs. With the help of Sankey diagrams, we illustrate the hydrogen bond network topology of the solutions, which is characterized by competing hydrogen bond donors and acceptors. The hydrogen bonds between cellulose and the anions possess average lifetimes in the nanosecond range, which is longer than found in common pure ILs. Full article

(This article belongs to the Special Issue Ionic Liquids, from Their Synthesis to Their Applications)

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25 pages, 865 KiB

Open AccessReview

Natural Compounds for Wood Protection against Fungi—A Review

by Magdalena Broda

Molecules 2020, 25(15), 3538; https://doi.org/10.3390/molecules25153538 - 2 Aug 2020

Cited by 126 | Viewed by 15180

Abstract

Wood is a renewable, versatile material with multiple applications and the largest terrestrial pool of sequestered carbon. However, it is susceptible to degradation, mainly caused by wood-decaying fungi. Since several traditional wood preservatives have been banned owing to their detrimental effects on humans [...] Read more.

Wood is a renewable, versatile material with multiple applications and the largest terrestrial pool of sequestered carbon. However, it is susceptible to degradation, mainly caused by wood-decaying fungi. Since several traditional wood preservatives have been banned owing to their detrimental effects on humans and the environment, extending the lifespan of wood products using new generation natural preservatives is an imperative from the perspectives of human health and environmental protection. Several natural compounds of plant and animal origin have been tested for their fungicidal properties, including essential oils, tannins, wood extractives, alkaloids, propolis or chitosan; and their enormous potential in wood protection has been shown. Although they are not free of limitations, the potential methods to overcome their drawbacks and enhance their bioactivity already exist, such as co-impregnation with different polymers, cross-linkers, metal chelators or antioxidants. The presence of the discrepancies between laboratory tests and the field performance, as well as legislation-related problems resulting from the lack of standards defining the quality and performance of natural protective formulations, however, create an urgent need for further thorough research and arrangements. The collaboration with other industries interested in the utilisation of natural active compounds will reduce the associated costs, thus, will facilitate the successful implementation of alternative antifungal agents. Full article

(This article belongs to the Special Issue Natural Products and Their Semi-synthetic Derivatives against Bacteria, Fungi and Parasites)

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26 pages, 3812 KiB

Open AccessFeature PaperArticle

Spin Density Topology

by Giovanna Bruno, Giovanni Macetti, Leonardo Lo Presti and Carlo Gatti

Molecules 2020, 25(15), 3537; https://doi.org/10.3390/molecules25153537 - 2 Aug 2020

Cited by 26 | Viewed by 5074

Abstract

Despite its role in spin density functional theory and it being the basic observable for describing and understanding magnetic phenomena, few studies have appeared on the electron spin density subtleties thus far. A systematic full topological analysis of this function is lacking, seemingly [...] Read more.

Despite its role in spin density functional theory and it being the basic observable for describing and understanding magnetic phenomena, few studies have appeared on the electron spin density subtleties thus far. A systematic full topological analysis of this function is lacking, seemingly in contrast to the blossoming in the last 20 years of many studies on the topological features of other scalar fields of chemical interest. We aim to fill this gap by unveiling the kind of information hidden in the spin density distribution that only its topology can disclose. The significance of the spin density critical points, the 18 different ways in which they can be realized and the peculiar topological constraints on their number and kind, arising from the presence of positive and negative spin density regions, is addressed. The notion of molecular spin graphs, spin maxima (minima) joining paths, spin basins and of their valence is introduced. We show that two kinds of structures are associated with a spin–polarized molecule: the usual one, defined through the electron density gradient, and the magnetic structure, defined through the spin density gradient and composed in general by at least two independent spin graphs, related to spin density maxima and minima. Several descriptors, such as the spin polarization index, are introduced to characterize the properties of spin density critical points and basins. The study on the general features of the spin density topology is followed by the specific example of the water molecule in the ³B₁ triplet state, using spin density distributions of increasing accuracy. Full article

(This article belongs to the Special Issue Advances in the Theory of Chemical Bonding)

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29 pages, 1218 KiB

Open AccessArticle

GC-MS Phytochemical Profiling, Pharmacological Properties, and In Silico Studies of Chukrasia velutina Leaves: A Novel Source for Bioactive Agents

by Israt Jahan, Marzia Rahman Tona, Sanjida Sharmin, Mohammed Aktar Sayeed, Fatamatuz Zuhura Tania, Arkajyoti Paul, Md. Nazim Uddin Chy, Ahmed Rakib, Talha Bin Emran and Jesus Simal-Gandara

Molecules 2020, 25(15), 3536; https://doi.org/10.3390/molecules25153536 - 2 Aug 2020

Cited by 44 | Viewed by 7236

Abstract

Chukrasia velutina is a local medicinal plant commonly known as chikrassy in Bangladesh, India, China, and other South Asian countries. The leaves, bark, and seeds are vastly used as herbal medicine for fever and diarrhea, and its leaves essential oils are used for [...] Read more.

Chukrasia velutina is a local medicinal plant commonly known as chikrassy in Bangladesh, India, China, and other South Asian countries. The leaves, bark, and seeds are vastly used as herbal medicine for fever and diarrhea, and its leaves essential oils are used for antimicrobial purposes. In this study, we discuss the neuropsychiatric properties of C. velutina leaves through several animal models, quantitative and qualitative phytochemical analysis, and computational approaches. Neuropsychiatric effects were performed in rodents on the methanolic extract of C. velutina leaves (MECVL). Antidepressant, anxiolytic, and sedative effects experimented through these rodent models were used such as the force swimming test (FST), tail suspension test (TST), hole board test (HBT), elevated plus maze test (EPMT), light/dark box test (LDBT), open field test (OFT), and hole cross test (HCT). In these rodent models, 200 and 400 mg/kg doses were used which exhibited a significant result in the force swimming and tail suspension test (p < 0.001) for the antidepressant effect. In the anxiolytic study, the results were significant in the hole board, elevated plus maze, and light/dark box test (p < 0.001) for doses of 200 and 400 mg/kg. The result was also significant in the open field and hole cross test (p < 0.001) for sedative action in the sake of similar doses. Moreover, qualitative and quantitative studies were also performed through phytochemical screening and GC-MS analysis, and fifty-seven phytochemical compounds were found. These compounds were analyzed for pharmacokinetics properties using the SwissADME tool and from them, thirty-five compounds were considered for the molecular docking analysis. These phytoconstituents were docking against the human serotonin receptor, potassium channel receptor, and crystal structure of human beta-receptor, where eight of the compounds showed a good binding affinity towards the respective receptors considered to the reference standard drugs. After all of these analyses, it can be said that the secondary metabolite of C. velutina leaves (MECVL) could be a good source for inhibiting the neuropsychiatric disorders which were found on animal models as well as in computational studies. Full article

(This article belongs to the Special Issue Modern Analytical Techniques in Metabolomics Analysis)

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14 pages, 3006 KiB

Open AccessFeature PaperArticle

Viscosified Solid Lipidic Nanoparticles Based on Naringenin and Linolenic Acid for the Release of Cyclosporine A on the Skin

by Sonia Trombino, Camilla Servidio, Annarita Stella Laganà, Filomena Conforti, Mariangela Marrelli and Roberta Cassano

Molecules 2020, 25(15), 3535; https://doi.org/10.3390/molecules25153535 - 2 Aug 2020

Cited by 19 | Viewed by 3890

Abstract

Psoriasis is one of the most common human skin disorders. Although its pathogenesis is complex and not completely know, the hyperactivation of the immune system seem to have a key role. In this regard, among the most effective systemic therapeutics used in psoriasis, [...] Read more.

Psoriasis is one of the most common human skin disorders. Although its pathogenesis is complex and not completely know, the hyperactivation of the immune system seem to have a key role. In this regard, among the most effective systemic therapeutics used in psoriasis, we find cyclosporine, an immunosuppressive medication. However, one of the major problems associated with the use of cyclosporine is the occurrence of systemic side effects such as nephrotoxicity, hypertension, etc. The present work fits in this context and its aim is the design of suitable platforms for cyclosporine topical release in psoriasis treatment. The main objective is to achieve local administration of cyclosporine in order to reduce its systemic absorption and, consequently, its side effects. In order to improve dermal penetration, solid lipid nanoparticles (SLNs) are used as carriers, due to their lipophilicity and occlusive properties, and naringenin and linolenic acid are chosen, due to their properties, as starting materials for SLNs design. In order to have dermatological formulations and further modulate drug release, SLNs are incorporated in several topical vehicles obtaining gels with different degree of lipophilicity. Potential applications for psoriasis treatment were evaluated by considering the encapsulation efficiency, release profiles, in vitro skin permeation, and anti-inflammatory effects. Full article

(This article belongs to the Special Issue Role of Hyaluronan in Biomedicine)

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16 pages, 3393 KiB

Open AccessFeature PaperArticle

Potential Use of Waste Activated Sludge Hydrothermally Treated as a Renewable Fuel or Activated Carbon Precursor

by J. A. Villamil, E. Diaz, M. A. de la Rubia and A. F. Mohedano

Molecules 2020, 25(15), 3534; https://doi.org/10.3390/molecules25153534 - 2 Aug 2020

Cited by 22 | Viewed by 4263

Abstract

In this work, dewatered waste activated sludge (DWAS) was subjected to hydrothermal carbonization to obtain hydrochars that can be used as renewable solid fuels or activated carbon precursors. A central composite rotatable design was used to analyze the effect of temperature (140–220 °C) [...] Read more.

In this work, dewatered waste activated sludge (DWAS) was subjected to hydrothermal carbonization to obtain hydrochars that can be used as renewable solid fuels or activated carbon precursors. A central composite rotatable design was used to analyze the effect of temperature (140–220 °C) and reaction time (0.5–4 h) on the physicochemical properties of the products. The hydrochars exhibited increased heating values (up to 22.3 MJ/kg) and their air-activation provided carbons with a low BET area (100 m²/g). By contrast, chemical activation with K₂CO₃, KOH, FeCl₃ and ZnCl₂ gave carbons with a well-developed porous network (BET areas of 410–1030 m²/g) and substantial contents in mesopores (0.079–0.271 cm³/g) and micropores (0.136–0.398 cm³/g). The chemically activated carbons had a fairly good potential to adsorb emerging pollutants such as sulfamethoxazole, antipyrine and desipramine from the liquid phase. This was especially the case with KOH-activated hydrochars, which exhibited a maximum adsorption capacity of 412, 198 and 146 mg/g, respectively, for the previous pollutants. Full article

(This article belongs to the Special Issue New Materials for a Sustainable Future)

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11 pages, 1051 KiB

Open AccessArticle

Constituents of Huberantha jenkinsii and Their Biological Activities

by Htoo Tint San, Tanawat Chaowasku, Wanwimon Mekboonsonglarp, Ratchanee Rodsiri, Boonchoo Sritularak, Hathairat Buraphaka, Waraporn Putalun and Kittisak Likhitwitayawuid

Molecules 2020, 25(15), 3533; https://doi.org/10.3390/molecules25153533 - 2 Aug 2020

Cited by 5 | Viewed by 3385

Abstract

The phytochemical investigation of Huberantha jenkinsii resulted in the isolation of two new and five known compounds. The new compounds were characterized as undescribed 8-oxoprotoberberine alkaloids and named huberanthines A and B, whereas the known compounds were identified as allantoin, oxylopinine, N- [...] Read more.

The phytochemical investigation of Huberantha jenkinsii resulted in the isolation of two new and five known compounds. The new compounds were characterized as undescribed 8-oxoprotoberberine alkaloids and named huberanthines A and B, whereas the known compounds were identified as allantoin, oxylopinine, N-trans-feruloyl tyramine, N-trans-p-coumaroyl tyramine, and mangiferin. The structure determination was accomplished by spectroscopic methods. To evaluate therapeutic potential in diabetes and Parkinson’s disease, the isolates were subjected to assays for their α-glucosidase inhibitory activity, cellular glucose uptake stimulatory activity, and protective activity against neurotoxicity induced by 6-hydroxydopamine (6-OHDA). The results suggested that mangiferin was the most promising lead compound, demonstrating significant activity in all the test systems. Full article

(This article belongs to the Section Natural Products Chemistry)

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33 pages, 5516 KiB

Open AccessReview

Cellulose-Based Carbon Molecular Sieve Membranes for Gas Separation: A Review

by Tiago Araújo, Gabriel Bernardo and Adélio Mendes

Molecules 2020, 25(15), 3532; https://doi.org/10.3390/molecules25153532 - 1 Aug 2020

Cited by 35 | Viewed by 7924

Abstract

In the field of gas separation and purification, membrane technologies compete with conventional purification processes on the basis of technical, economic and environmental factors. In this context, there is a growing interest in the development of carbon molecular sieve membranes (CMSM) due to [...] Read more.

In the field of gas separation and purification, membrane technologies compete with conventional purification processes on the basis of technical, economic and environmental factors. In this context, there is a growing interest in the development of carbon molecular sieve membranes (CMSM) due to their higher permeability and selectivity and higher stability in corrosive and high temperature environments. However, the industrial use of CMSM has been thus far hindered mostly by their relative instability in the presence of water vapor, present in a large number of process streams, as well as by the high cost of polymeric precursors such as polyimide. In this context, cellulosic precursors appear as very promising alternatives, especially targeting the production of CMSM for the separation of O₂/N₂ and CO₂/CH₄. For these two gas separations, cellulose-based CMSM have demonstrated performances well above the Robeson upper bound and above the performance of CMSM based on other polymeric precursors. Furthermore, cellulose is an inexpensive bio-renewable feed-stock highly abundant on Earth. This article reviews the major fabrication aspects of cellulose-based CMSM. Additionally, this article suggests a new tool to characterize the membrane performance, the Robeson Index. The Robeson Index, θ, is the ratio between the actual selectivity at the Robeson plot and the corresponding selectivity—for the same permeability—of the Robeson upper bound; the Robeson Index measures how far the actual point is from the upper bound. Full article

(This article belongs to the Special Issue Lignocellulosic Materials)

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33 pages, 1623 KiB

Open AccessReview

Bioactive Compounds and Metabolites from Grapes and Red Wine in Breast Cancer Chemoprevention and Therapy

by Danielly C. Ferraz da Costa, Luciana Pereira Rangel, Julia Quarti, Ronimara A. Santos, Jerson L. Silva and Eliane Fialho

Molecules 2020, 25(15), 3531; https://doi.org/10.3390/molecules25153531 - 1 Aug 2020

Cited by 35 | Viewed by 7713

Abstract

Phytochemicals and their metabolites are not considered essential nutrients in humans, although an increasing number of well-conducted studies are linking their higher intake with a lower incidence of non-communicable diseases, including cancer. This review summarizes the current findings concerning the molecular mechanisms of [...] Read more.

Phytochemicals and their metabolites are not considered essential nutrients in humans, although an increasing number of well-conducted studies are linking their higher intake with a lower incidence of non-communicable diseases, including cancer. This review summarizes the current findings concerning the molecular mechanisms of bioactive compounds from grapes and red wine and their metabolites on breast cancer—the most commonly occurring cancer in women—chemoprevention and treatment. Flavonoid compounds like flavonols, monomeric catechins, proanthocyanidins, anthocyanins, anthocyanidins and non-flavonoid phenolic compounds, such as resveratrol, as well as their metabolites, are discussed with respect to structure and metabolism/bioavailability. In addition, a broad discussion regarding in vitro, in vivo and clinical trials about the chemoprevention and therapy using these molecules is presented. Full article

(This article belongs to the Special Issue Anticancer Properties of Natural and Derivative Products)

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18 pages, 2112 KiB

Open AccessArticle

Flavonoids and Terpenoids with PTP-1B Inhibitory Properties from the Infusion of Salvia amarissima Ortega

by Eric Salinas-Arellano, Araceli Pérez-Vásquez, Isabel Rivero-Cruz, Rafael Torres-Colin, Martín González-Andrade, Manuel Rangel-Grimaldo and Rachel Mata

Molecules 2020, 25(15), 3530; https://doi.org/10.3390/molecules25153530 - 1 Aug 2020

Cited by 19 | Viewed by 4285

Abstract

An infusion prepared from the aerial parts of Salvia amarissima Ortega inhibited the enzyme protein tyrosine phosphatase 1B (PTP-1B) (IC₅₀~88 and 33 μg/mL, respectively). Phytochemical analysis of the infusion yielded amarisolide (1), 5,6,4′-trihydroxy-7,3′-dimethoxyflavone (2), 6-hydroxyluteolin (3 [...] Read more.

An infusion prepared from the aerial parts of Salvia amarissima Ortega inhibited the enzyme protein tyrosine phosphatase 1B (PTP-1B) (IC₅₀~88 and 33 μg/mL, respectively). Phytochemical analysis of the infusion yielded amarisolide (1), 5,6,4′-trihydroxy-7,3′-dimethoxyflavone (2), 6-hydroxyluteolin (3), rutin (4), rosmarinic acid (5), isoquercitrin (6), pedalitin (7) and a new neo-clerodane type diterpenoid glucoside, named amarisolide G (8a,b). Compound 8a,b is a new natural product, and 2–6 are reported for the first time for the species. All compounds were tested for their inhibitory activity against PTP-1B; their IC₅₀ values ranged from 62.0 to 514.2 μM. The activity was compared to that of ursolic acid (IC₅₀ = 29.14 μM). The most active compound was pedalitin (7). Docking analysis predicted that compound 7 has higher affinity for the allosteric site of the enzyme. Gas chromatography coupled to mass spectrometry analyses of the essential oils prepared from dried and fresh materials revealed that germacrene D (15) and β-selinene (16), followed by β-caryophyllene (13) and spathulenol (17) were their major components. An ultra-high performance liquid chromatography coupled to mass spectrometry method was developed and validated to quantify amarisolide (1) in the ethyl acetate soluble fraction of the infusion of S. amarissima. Full article

(This article belongs to the Special Issue From Ethnobotany to Ecopharmacognosy: Chemical Characterization and Bioactivity Evaluation of Medicinal and Aromatic Plants)

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13 pages, 1230 KiB

Open AccessReview

Invasive Plants: Turning Enemies into Value

by Patrícia Máximo, Luísa M. Ferreira, Paula S. Branco and Ana Lourenço

Molecules 2020, 25(15), 3529; https://doi.org/10.3390/molecules25153529 - 1 Aug 2020

Cited by 20 | Viewed by 4464

Abstract

In this review, a brief description of the invasive phenomena associated with plants and its consequences to the ecosystem is presented. Five worldwide invasive plants that are a threat to Portugal were selected as an example, and a brief description of each is [...] Read more.

In this review, a brief description of the invasive phenomena associated with plants and its consequences to the ecosystem is presented. Five worldwide invasive plants that are a threat to Portugal were selected as an example, and a brief description of each is presented. A full description of their secondary metabolites and biological activity is given, and a resume of the biological activity of extracts is also included. The chemical and pharmaceutical potential of invasive species sensu lato is thus acknowledged. With this paper, we hope to demonstrate that invasive species have potential positive attributes even though at the same time they might need to be controlled or eradicated. Positive attributes include chemical and pharmaceutical properties and developing these could help mitigate the costs of management and eradication. Full article

(This article belongs to the Section Natural Products Chemistry)

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