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Molecules, Volume 25, Issue 5 (March-1 2020) – 240 articles

Cover Story (view full-size image): Organotin hydrides have demonstrated their potential to be used as building blocks for a great variety of organometallic compounds. Organotin hydrides with sterically shielding aryl substituents, in particular, have attracted special interest as these ligands can kinetically stabilize metastable products. As part of the Special issue “Organometallic Synthesis of Extremely Sensitive Compounds for Fundamental Investigations, Bond Activation, and Catalysis” with Guest Editor Dr. Burgert Blom, we present the synthesis of aryltin hydrides featuring a sterically encumbered aryl ligand, which exhibit enough steric protection to shield the tin hydrogen bond and make the isolated compounds more thermally stable and more tolerant towards oxygen. The steric potential is visualized on the cover. View this paper.
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Article
Unprecedented Water Effect as a Key Element in Salicyl-Glycine Schiff Base Synthesis
Molecules 2020, 25(5), 1257; https://doi.org/10.3390/molecules25051257 - 10 Mar 2020
Cited by 5 | Viewed by 2252
Abstract
Salens, as chelating, double Schiff base ligands, are an important group utilized in transition metal catalysis. They have been used to build interesting functional metal-organic frameworks (MOFs). However, salens interacting with amino acids have also found applications in receptors. Here, we intended to [...] Read more.
Salens, as chelating, double Schiff base ligands, are an important group utilized in transition metal catalysis. They have been used to build interesting functional metal-organic frameworks (MOFs). However, salens interacting with amino acids have also found applications in receptors. Here, we intended to form a “green” glycine-derived salen fragment, but the available literature data were contradictory. Therefore, we optimized the synthetic conditions and obtained the desired product as two different crystallographic polymorphs (orthorhombic Pcca and monoclinic P21/c space groups). Their structures differ in conformation at the glycine moiety, and the monoclinic form contains additional, disordered water molecules. Despite the high stability of Schiff bases, these newly obtained compounds hydrolyze in aqueous media, the process being accelerated by metal cations. These studies, accompanied by mechanistic considerations and solid-state moisture and thermal analysis, clarify the structure and behavior of this amino acid Schiff base and shed new light on the role of water in its stability. Full article
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Article
Simplified ICP OES-Based Method for Determination of 12 Elements in Commercial Bottled Birch Saps: Validation and Bioaccessibility Study
Molecules 2020, 25(5), 1256; https://doi.org/10.3390/molecules25051256 - 10 Mar 2020
Cited by 2 | Viewed by 1361
Abstract
Commercially bottled birch saps (BSs) were analyzed for several nutrient (Ca, Cu, Fe, Mg, and Zn) and toxic (As, Cd, Ni, and Pb) elements using inductively coupled plasma optical emission spectrometry (ICP OES). The method was validated under the conditions of several sample [...] Read more.
Commercially bottled birch saps (BSs) were analyzed for several nutrient (Ca, Cu, Fe, Mg, and Zn) and toxic (As, Cd, Ni, and Pb) elements using inductively coupled plasma optical emission spectrometry (ICP OES). The method was validated under the conditions of several sample preparation procedures, including a traditional digestion as well as alternative non-digestion schemes. It was found that the direct analysis of untreated BSs gives the best results, i.e., limits of detection at 0.02–5.8 ng mL−1, precision better than 5%, accuracy from 98.0% to 104.5% and determination of 12 elements in a short time (~1 min per sample). The multi-element analysis of nine commercially available bottled BSs showed that they contained mainly Mg and Ca, small quantities of Mn, Zn, Cu, and Fe, but are free from toxic elements such as As, Cd, Ni, and Pb. Additionally, the nutritional value of BSs was examined using in vitro gastro-intestinal digestion (GID) to determine the bioaccessible fraction of elements. Accordingly, bioaccessibility of nutritious ones (Ca, Cu, Fe, Mg, Zn) was <40%. Drinking daily 1 L of BSs covered <2.5% of recommended dietary intakes (RDIs) of the aforementioned elements. Only the bioaccessibility of Mn highly contributes to its RDI. Full article
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Article
Synthesis and Structure-Activity Relationship Studies of Hydrazide-Hydrazones as Inhibitors of Laccase from Trametes versicolor
Molecules 2020, 25(5), 1255; https://doi.org/10.3390/molecules25051255 - 10 Mar 2020
Cited by 10 | Viewed by 2664
Abstract
A series of hydrazide-hydrazones 1–3, the imine derivatives of hydrazides and aldehydes bearing benzene rings, were screened as inhibitors of laccase from Trametes versicolor. Laccase is a copper-containing enzyme which inhibition might prevent or reduce the activity of the plant pathogens [...] Read more.
A series of hydrazide-hydrazones 1–3, the imine derivatives of hydrazides and aldehydes bearing benzene rings, were screened as inhibitors of laccase from Trametes versicolor. Laccase is a copper-containing enzyme which inhibition might prevent or reduce the activity of the plant pathogens that produce it in various biochemical processes. The kinetic and molecular modeling studies were performed and for selected compounds, the docking results were discussed. Seven 4-hydroxybenzhydrazide (4-HBAH) derivatives exhibited micromolar activity Ki = 24–674 µM with the predicted and desirable competitive type of inhibition. The structure–activity relationship (SAR) analysis revealed that a slim salicylic aldehyde framework had a pivotal role in stabilization of the molecules near the substrate docking site. Furthermore, the presence of phenyl and bulky tert-butyl substituents in position 3 in salicylic aldehyde fragment favored strong interaction with the substrate-binding pocket in laccase. Both 3- and 4-HBAH derivatives containing larger 3-tert-butyl-5-methyl- or 3,5-di-tert-butyl-2-hydroxy-benzylidene unit, did not bind to the active site of laccase and, interestingly, acted as non-competitive (Ki = 32.0 µM) or uncompetitive (Ki = 17.9 µM) inhibitors, respectively. From the easily available laccase inhibitors only sodium azide, harmful to environment and non-specific, was over 6 times more active than the above compounds. Full article
(This article belongs to the Special Issue New Studies on the Synthesis of Biologically Active Products)
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Article
Liquid Chromatography–Tandem Mass Spectrometry for the Simultaneous Determination of Doxorubicin and its Metabolites Doxorubicinol, Doxorubicinone, Doxorubicinolone, and 7-Deoxydoxorubicinone in Mouse Plasma
Molecules 2020, 25(5), 1254; https://doi.org/10.3390/molecules25051254 - 10 Mar 2020
Cited by 6 | Viewed by 1602
Abstract
Doxorubicin, an anthracycline antitumor antibiotic, acts as a cancer treatment by interfering with the function of DNA. Herein, liquid chromatography-tandem mass spectrometry was for the first time developed and validated for the simultaneous determination of doxorubicin and its major metabolites doxorubicinol, doxorubicinone, doxorubicinolone, [...] Read more.
Doxorubicin, an anthracycline antitumor antibiotic, acts as a cancer treatment by interfering with the function of DNA. Herein, liquid chromatography-tandem mass spectrometry was for the first time developed and validated for the simultaneous determination of doxorubicin and its major metabolites doxorubicinol, doxorubicinone, doxorubicinolone, and 7-deoxydoxorubicinone in mouse plasma. The liquid–liquid extraction of a 10 μL mouse plasma sample with chloroform:methanol (4:1, v/v) and use of the selected reaction monitoring mode led to less matrix effect and better sensitivity. The lower limits of quantification levels were 0.5 ng/mL for doxorubicin, 0.1 ng/mL for doxorubicinol, and 0.01 ng/mL for doxorubicinone, doxorubicinolone, and 7-deoxydoxorubicinone. The standard curves were linear over the range of 0.5–200 ng/mL for doxorubicin; 0.1–200 ng/mL for doxorubicinol; and 0.01–50 ng/mL for doxorubicinone, doxorubicinolone, and 7-deoxydoxorubicinone in mouse plasma. The intra and inter-day relative standard deviation and relative errors for doxorubicin and its four metabolites at four quality control concentrations were 0.9–13.6% and –13.0% to 14.9%, respectively. This method was successfully applied to the pharmacokinetic study of doxorubicin and its metabolites after intravenous administration of doxorubicin at a dose of 1.3 mg/kg to female BALB/c nude mice. Full article
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Article
Anticancer Activities of Newly Synthesized Chiral Macrocyclic Heptapeptide Candidates
Molecules 2020, 25(5), 1253; https://doi.org/10.3390/molecules25051253 - 10 Mar 2020
Cited by 23 | Viewed by 1438
Abstract
As important cancer therapeutic agents, macrocyclic peptides have recently drawn great attention, mainly because they are synthetically accessible and have lower toxicity towards normal cells. In the present work, we synthesized newly macrocyclic pyridoheptapeptide derivatives. The synthesized derivatives were characterized using standard chemical [...] Read more.
As important cancer therapeutic agents, macrocyclic peptides have recently drawn great attention, mainly because they are synthetically accessible and have lower toxicity towards normal cells. In the present work, we synthesized newly macrocyclic pyridoheptapeptide derivatives. The synthesized derivatives were characterized using standard chemical and spectroscopic analytical techniques, and their anticancer activities against human breast and hepatocellular cancer cells were investigated. Results showed that compounds 1a and 1b were the most effective against hepatocellular (HepG2) and breast (MCF-7) cancer cell lines, respectively. Full article
(This article belongs to the Special Issue Recent Advances in Anticancer Drugs II)
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Article
Antibacterial Action Mechanisms of Honey: Physiological Effects of Avocado, Chestnut, and Polyfloral Honey upon Staphylococcus aureus and Escherichia coli
Molecules 2020, 25(5), 1252; https://doi.org/10.3390/molecules25051252 - 10 Mar 2020
Cited by 10 | Viewed by 1775
Abstract
Numerous studies have explored the antibacterial properties of different types of honey from all around the world. However, the data available describing how honey acts against bacteria are few. The aim of this study was to apply a flow cytometry (FC) protocol to [...] Read more.
Numerous studies have explored the antibacterial properties of different types of honey from all around the world. However, the data available describing how honey acts against bacteria are few. The aim of this study was to apply a flow cytometry (FC) protocol to examine and characterize the primary effects of three varieties of honey (avocado, chestnut and polyfloral) upon physiological status of Staphylococcus aureus and Escherichia coli cells to reveal their antibacterial action mechanisms. The effects of honey samples on membrane potential, membrane integrity, and metabolic activity were assessed using different fluorochromes, in a 180 min time course assay. Time-kill experiments were also carried out under similar conditions. Exposure of S. aureus and E. coli to the distinct honey samples resulted in physiological changes related to membrane polarization and membrane integrity. Moreover, honey induced a remarkable metabolic disruption as primary physiological effect upon S. aureus. The different honey samples induced quite similar effects on both bacteria. However, the depth of bacteria response throughout the treatment varied depending on the concentration tested and among honey varieties, probably due to compositional differences in the honey. Full article
(This article belongs to the Special Issue Nutraceuticals: Role in Health and Disease)
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Article
Effects of Cyclic Freeze–Thaw on the Steel Bar Reinforced New-To-Old Concrete Interface
Molecules 2020, 25(5), 1251; https://doi.org/10.3390/molecules25051251 - 10 Mar 2020
Cited by 4 | Viewed by 1249
Abstract
Frost damage of concrete has significant effects on the safety and durability of concrete structures in cold regions, and the concrete structures after repair and reinforcement are still threatened by cyclic freezing and thawing. In this study, the new-to-old concrete interface was reinforced [...] Read more.
Frost damage of concrete has significant effects on the safety and durability of concrete structures in cold regions, and the concrete structures after repair and reinforcement are still threatened by cyclic freezing and thawing. In this study, the new-to-old concrete interface was reinforced by steel bar. The shear strength of the new-to-old concrete interface was tested after the new-to-old combination was subjected to cyclic freeze–thaw. The effects of the diameter of the steel bar, the compressive strength of new concrete, the number of freeze–thaw cycles and the freezing temperatures on the shear properties of new-to-old concrete interface were studied. The results showed that, in a certain range, the shear strength of the interface was proportional to the diameter of the steel bar and the strength of the new concrete. Meanwhile, the shear strength of the reinforced interface decreased with the decreasing of the freezing temperature and the increasing of the number of freeze–thaw cycles. Full article
(This article belongs to the Special Issue Structural Mechanics of Composite Materials and Structures)
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Article
Pharmacokinetics of Two Chlorine-Substituted Bis-Pyridinium Mono-Aldoximes with Regenerating Effect on Butyrylcholinesterase
Molecules 2020, 25(5), 1250; https://doi.org/10.3390/molecules25051250 - 10 Mar 2020
Cited by 2 | Viewed by 1269
Abstract
Our aim was to find chlorine-substituted antidotes against organophosphate poisoning and compare their pharmacokinetics to their parent compound, K-203. White male Wistar rats were intramuscularly injected with K-203, K-867 or K-870. Serum, brain, kidneys, liver, lung, eyes, and testes tissues were taken after [...] Read more.
Our aim was to find chlorine-substituted antidotes against organophosphate poisoning and compare their pharmacokinetics to their parent compound, K-203. White male Wistar rats were intramuscularly injected with K-203, K-867 or K-870. Serum, brain, kidneys, liver, lung, eyes, and testes tissues were taken after 5, 15, 30, 60, and 120 min and analyzed using reversed-phase high-performance liquid chromatography. K-203, K-867, or K-870 was present in every tissue that was analyzed, including the serum, the eyes, testes, liver, kidneys, lungs, and the brain. The serum levels of K-867 and K-870 (chlorine-substituted derivatives of K-203) were nearly constant between 15 and 30 min, while their parent compound (K-203) showed peak level at 15 min after the administration of 30 µmol/rat. Neither K-203, nor K-867 or K-870 were toxic at a dose of 100 µmol/200 g in rats. Chlorine-substitution of K-867 and K-870 produced limited absorbance and distribution compared to their parent compound, K203. Full article
(This article belongs to the Special Issue Chemistry of Antidotes)
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Article
Contribution of Cross-Linker and Silica Morphology on Cr(VI) Sorption Performances of Organic Anion Exchangers Embedded into Silica Pores
Molecules 2020, 25(5), 1249; https://doi.org/10.3390/molecules25051249 - 10 Mar 2020
Cited by 7 | Viewed by 1227
Abstract
Removal of Cr(VI) from the environment represents a stringent issue because of its tremendous effects on living organisms. In this context, design of sorbents with high sorption capacity for Cr(VI) is getting a strong need. For this purpose, poly(vinylbenzyl chloride), impregnated into porous [...] Read more.
Removal of Cr(VI) from the environment represents a stringent issue because of its tremendous effects on living organisms. In this context, design of sorbents with high sorption capacity for Cr(VI) is getting a strong need. For this purpose, poly(vinylbenzyl chloride), impregnated into porous silica (PSi), was cross-linked with either N,N,N’,N’-tetramethyl-1,2-ethylenediamine (TEMED) or N,N,N’,N’-tetramethyl-1,3-propanediamine, followed by the reaction of the free -CH2Cl groups with N,N-diethyl-2-hydroxyethylamine to generate strong base anion exchangers (ANEX) inside the pores. The PSi/ANEX composite sorbents were deeply characterized by FTIR spectroscopy, SEM-energy dispersive X-ray spectroscopy (EDX), thermogravimetric analysis (TGA), and water uptake. The sorption performances of composites against Cr(VI) were investigated as a function of pH, contact time, initial concentration of Cr(VI), and temperature. It was found that the cross-linker structure and the silica morphology are the key factors controlling the sorption capacity. The adsorption process was spontaneous and endothermic and well described by pseudo-second-order kinetic and Sips isotherm models. The maximum sorption capacity of 311.2 mg Cr(VI)/g sorbent was found for the composite prepared with mesoporous silica using TEMED as cross-linker. The PSi/ANEX composite sorbents represent an excellent alternative for the removal of Cr(VI) oxyanions, being endowed with fast kinetics, equilibrium in about 60 min, and a high level of reusability in successive sorption/desorption cycles. Full article
(This article belongs to the Special Issue Application of Sorption Materials in Environment)
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Article
On Column Binding a Real-Time Biosensor for β-lactam Antibiotics Quantification
Molecules 2020, 25(5), 1248; https://doi.org/10.3390/molecules25051248 - 10 Mar 2020
Cited by 3 | Viewed by 1292
Abstract
This work aimed to develop accurate, quick, and practical tools for the detection of residues of penicillin G antibiotic in biological and non-biological samples. The assays were developed based on the binding mechanism of β-lactam to penicillin-binding proteins; samples of different concentrations [...] Read more.
This work aimed to develop accurate, quick, and practical tools for the detection of residues of penicillin G antibiotic in biological and non-biological samples. The assays were developed based on the binding mechanism of β-lactam to penicillin-binding proteins; samples of different concentrations of penicillin G were incubated with in vitro expressed 6X-Histidine-tagged soluble penicillin-binding protein (PBP2x*) of Streptococcus pneumoniae (S. pneumoniae), whereby penicillin G in samples specifically binds to PBP2x*. The fluorescent-labeled β-lactam analogue Bocillin FL was used as a competent substrate, and two different routes estimated the amounts of the penicillin G. The first route was established based on the differences in the concentration of non-bounded Bocillin FL molecules within the reactions while using a real-time polymerase chain reaction (PCR)-based method for fluorescence detection. The second route depended on the amount of the relative intensity of Bocillin FL bounded to Soluble PBP-2x*, being run on sodium dodecyl sulfate–polyacrylamide gel electrophoresis (SDS-page), visualized by a ChemiDoc-It®2 Imager, and quantified based on the fluorescence affinity of the competent substrate. While both of the methods gave a broad range of linearity and high sensitivity, the on column based real-time method is fast, non-time consuming, and highly sensitive. The method identified traces of antibiotic in the range 0.01–0.2 nM in addition to higher accuracy in comparison to the SDS-based detection method, while the sensitivity of the SDS-based method ranged between 0.015 and 2 µM). Thus, the on column based real time assay is a fast novel method, which was developed for the first time based on the binding inhibition of a fluorescence competitor material and it can be adapted to screen traces of penicillin G in any biological and environmental samples. Full article
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Article
Antioxidant, α-Glucosidase, and Nitric Oxide Inhibitory Activities of Six Algerian Traditional Medicinal Plant Extracts and 1H-NMR-Based Metabolomics Study of the Active Extract
Molecules 2020, 25(5), 1247; https://doi.org/10.3390/molecules25051247 - 10 Mar 2020
Cited by 7 | Viewed by 1581
Abstract
Claims of effective therapy against diabetes using plants including Peganum harmala L., Zygophyllum album, Anacyclus valentinus L., Ammodaucus leucotrichus, Lupinus albus, and Marrubium vulgare in Algerian empirical medicine prompted our interest in evaluating their antidiabetic activity by screening their free radical scavenging [...] Read more.
Claims of effective therapy against diabetes using plants including Peganum harmala L., Zygophyllum album, Anacyclus valentinus L., Ammodaucus leucotrichus, Lupinus albus, and Marrubium vulgare in Algerian empirical medicine prompted our interest in evaluating their antidiabetic activity by screening their free radical scavenging (DPPH), α-glucosidase, and nitric oxide (NO) inhibitory activities as well as the total phenolic content (TPC). Extracts of the selected plants were prepared using different ratios of ethanol (0, 50, 80, and 100%). In this study, 100%, and 80% ethanol extracts of L. albus were found to be the most potent, in inhibiting α-glucosidase activity with IC50 values of 6.45 and 8.66 μg/mL, respectively. The 100% ethanol extract of A. leucotrichus exhibited the highest free radical scavenging activity with an IC50 value of 26.26 μg/mL. Moreover, the highest TPC of 612.84 μg GAE/mg extract was observed in M. vulgare, extracted with 80% ethanol. Metabolite profiling of the active extract was conducted using 1H-NMR metabolomics. Partial least square analysis (PLS) was used to assess the relationship between the α-glucosidase inhibitory activity of L. albus and the metabolites identified in the extract. Based on the PLS model, isoflavonoids (lupinoisoflavone G, lupisoflavone, lupinoisolone C), amino acids (asparagine and thiamine), and several fatty acids (stearic acid and oleic acid) were identified as metabolites that contributed to the inhibition of α-glucosidase activity. The results of this study have clearly strengthened the traditional claim of the antihyperglycemic effects of L. albus. Full article
(This article belongs to the Special Issue Biological Activities of Medicinal Plants)
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Article
Discordant Activity of Kaempferol Towards Dengue Virus and Japanese Encephalitis Virus
Molecules 2020, 25(5), 1246; https://doi.org/10.3390/molecules25051246 - 10 Mar 2020
Cited by 11 | Viewed by 1834
Abstract
Kaempferol, a plant-derived flavonoid, has been reported to have activity against Japanese encephalitis virus (JEV) in BHK-21 cells. To determine the broader utility of this compound, we initially evaluated the activity of kaempferol against JEV and dengue virus (DENV) in HEK293T/17 cells. Results [...] Read more.
Kaempferol, a plant-derived flavonoid, has been reported to have activity against Japanese encephalitis virus (JEV) in BHK-21 cells. To determine the broader utility of this compound, we initially evaluated the activity of kaempferol against JEV and dengue virus (DENV) in HEK293T/17 cells. Results showed no significant antiviral activity against either virus. We subsequently investigated the activity of kaempferol against both JEV and DENV in BHK-21 cells. Results showed a significant inhibition of JEV infection but, surprisingly, a significant enhancement of DENV infection. The effect of kaempferol on both host protein expression and transcription was investigated and both transcriptional and translational inhibitory effects were observed, although a more marked effect was observed on host cell protein expression. Markedly, while GRP78 was increased in DENV infected cells treated with kaempferol, it was not increased in JEV infected cells treated with kaempferol. These results show that cellular alteration induced by one compound can have opposite effects on viruses from the same family, suggesting the presence of distinct replication strategies for these two viruses. Full article
(This article belongs to the Special Issue Herbal Medicines as Antivirals)
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Article
Identification of Novel Chemical Entities for Adenosine Receptor Type 2A Using Molecular Modeling Approaches
Molecules 2020, 25(5), 1245; https://doi.org/10.3390/molecules25051245 - 10 Mar 2020
Cited by 24 | Viewed by 2861
Abstract
Adenosine Receptor Type 2A (A2AAR) plays a role in important processes, such as anti-inflammatory ones. In this way, the present work aimed to search for compounds by pharmacophore-based virtual screening. The pharmacokinetic/toxicological profiles of the compounds, as well as a robust [...] Read more.
Adenosine Receptor Type 2A (A2AAR) plays a role in important processes, such as anti-inflammatory ones. In this way, the present work aimed to search for compounds by pharmacophore-based virtual screening. The pharmacokinetic/toxicological profiles of the compounds, as well as a robust QSAR, predicted the binding modes via molecular docking. Finally, we used molecular dynamics to investigate the stability of interactions from ligand-A2AAR. For the search for A2AAR agonists, the UK-432097 and a set of 20 compounds available in the BindingDB database were studied. These compounds were used to generate pharmacophore models. Molecular properties were used for construction of the QSAR model by multiple linear regression for the prediction of biological activity. The best pharmacophore model was used by searching for commercial compounds in databases and the resulting compounds from the pharmacophore-based virtual screening were applied to the QSAR. Two compounds had promising activity due to their satisfactory pharmacokinetic/toxicological profiles and predictions via QSAR (Diverset 10002403 pEC50 = 7.54407; ZINC04257548 pEC50 = 7.38310). Moreover, they had satisfactory docking and molecular dynamics results compared to those obtained for Regadenoson (Lexiscan®), used as the positive control. These compounds can be used in biological assays (in vitro and in vivo) in order to confirm the potential activity agonist to A2AAR. Full article
(This article belongs to the Section Medicinal Chemistry)
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Article
Proteomic Analysis of the Early Development of the Phalaenopsis amabilis Flower Bud under Low Temperature Induction Using the iTRAQ/MRM Approach
Molecules 2020, 25(5), 1244; https://doi.org/10.3390/molecules25051244 - 10 Mar 2020
Cited by 2 | Viewed by 1327
Abstract
Phalaenopsis amabilis, one of the most important plants in the international flower market due to its graceful shape and colorful flowers, is an orchid that undergoes vernalization and requires low-temperature treatment for flowering. There have been few reports on the proteomics of [...] Read more.
Phalaenopsis amabilis, one of the most important plants in the international flower market due to its graceful shape and colorful flowers, is an orchid that undergoes vernalization and requires low-temperature treatment for flowering. There have been few reports on the proteomics of the development of flower buds. In this study, isobaric tags for relative and absolute quantification (iTRAQ) were used to identify 5064 differentially expressed proteins in P. amabilis under low-temperature treatment; of these, 42 were associated with early floral induction, and 18 were verified by mass spectrometry multi-reaction monitoring (MRM). The data are available via ProteomeXchange under identifier PXD013908. Among the proteins associated with the vernalization pathway, PEQU_11434 (glycine-rich RNA-binding protein GRP1A-like) and PEQU_19304 (FT, VRN3 homolog) were verified by MRM, and some other important proteins related to vernalization and photoperiod pathway that were detected by iTRAQ but not successfully verified by MRM, such as PEQU_11045 (UDP-N-acetylglucosamine diphosphorylase), phytochromes A (PEQU_13449, PEQU_35378), B (PEQU_09249), and C (PEQU_41401). Our data revealed a regulation network of the early development of flower buds in P. amabilis under low temperature induction. Full article
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Article
Synthesis and Biological Evaluation of a Novel C8-Pyrrolobenzodiazepine (PBD) Adenosine Conjugate. A Study on the Role of the PBD Ring in the Biological Activity of PBD-Conjugates
Molecules 2020, 25(5), 1243; https://doi.org/10.3390/molecules25051243 - 10 Mar 2020
Cited by 2 | Viewed by 1684
Abstract
Here we sought to evaluate the contribution of the PBD unit to the biological activity of PBD-conjugates and, to this end, an adenosine nucleoside was attached to the PBD A-ring C8 position. A convergent approach was successfully adopted for the synthesis of a [...] Read more.
Here we sought to evaluate the contribution of the PBD unit to the biological activity of PBD-conjugates and, to this end, an adenosine nucleoside was attached to the PBD A-ring C8 position. A convergent approach was successfully adopted for the synthesis of a novel C8-linked pyrrolo(2,1-c)(1,4)benzodiazepine(PBD)-adenosine(ADN) hybrid. The PBD and adenosine (ADN) moieties were synthesized separately and then linked through a pentynyl linker. To our knowledge, this is the first report of a PBD connected to a nucleoside. Surprisingly, the compound showed no cytotoxicity against murine cells and was inactive against Mycobacterium aurum and M. bovis strains and did not bind to guanine-containing DNA sequences, as shown by DNase I footprinting experiments. Molecular dynamics simulations revealed that the PBD–ADN conjugate was poorly accommodated in the DNA minor groove of two DNA sequences containing the AGA-PBD binding motif, with the adenosine moiety of the ligand preventing the covalent binding of the PBD unit to the guanine amino group of the DNA duplex. These interesting findings shed further light on the ability of the substituents attached at the C8 position of PBDs to affect and modulate the biological and biophysical properties of PBD hybrids. Full article
(This article belongs to the Special Issue Synthetic Heterocyclic Chemistry)
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Unveiling the Molecular Basis of Mascarpone Cheese Aroma: VOCs analysis by SPME-GC/MS and PTR-ToF-MS
Molecules 2020, 25(5), 1242; https://doi.org/10.3390/molecules25051242 - 10 Mar 2020
Cited by 10 | Viewed by 2506
Abstract
Mascarpone, a soft-spread cheese, is an unripened dairy product manufactured by the thermal-acidic coagulation of milk cream. Due to the mild flavor and creamy consistency, it is a base ingredient in industrial, culinary, and homemade preparations (e.g., it is a key constituent of [...] Read more.
Mascarpone, a soft-spread cheese, is an unripened dairy product manufactured by the thermal-acidic coagulation of milk cream. Due to the mild flavor and creamy consistency, it is a base ingredient in industrial, culinary, and homemade preparations (e.g., it is a key constituent of a widely appreciated Italian dessert ‘Tiramisù’). Probably due to this relevance as an ingredient rather than as directly consumed foodstuff, mascarpone has not been often the subject of detailed studies. To the best of our knowledge, no investigation has been carried out on the volatile compounds contributing to the mascarpone cheese aroma profile. In this study, we analyzed the Volatile Organic Compounds (VOCs) in the headspace of different commercial mascarpone cheeses by two different techniques: Headspace-Solid Phase Microextraction-Gas Chromatography-Mass Spectrometry (HS-SPME GC-MS) and Proton-Transfer Reaction-Mass Spectrometry coupled to a Time of Flight mass analyzer (PTR-ToF-MS). We coupled these two approaches due to the complementarity of the analytical potential—efficient separation and identification of the analytes on the one side (HS-SPME GC-MS), and effective, fast quantitative analysis without any sample preparation on the other (PTR-ToF-MS). A total of 27 VOCs belonging to different chemical classes (9 ketones, 5 alcohols, 4 organic acids, 3 hydrocarbons, 2 furans, 1 ester, 1 lactone, 1 aldehyde, and 1 oxime) have been identified by HS-SPME GC-MS, while PTR-ToF-MS allowed a rapid snapshot of volatile diversity confirming the aptitude to rapid noninvasive quality control and the potential in commercial sample differentiation. Ketones (2-heptanone and 2-pentanone, in particular) are the most abundant compounds in mascarpone headspace, followed by 2-propanone, 2-nonanone, 2-butanone, 1-pentanol, 2-ethyl-1-hexanol, furfural and 2-furanmethanol. The study also provides preliminary information on the differentiation of the aroma of different brands and product types. Full article
(This article belongs to the Special Issue Volatile Compounds and Smell Chemicals (Odor and Aroma) of Food)
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Review
A Review on Liquid Crystal Polymers in Free-Standing Reversible Shape Memory Materials
Molecules 2020, 25(5), 1241; https://doi.org/10.3390/molecules25051241 - 10 Mar 2020
Cited by 19 | Viewed by 2883
Abstract
Liquid crystal polymers have attracted massive attention as stimuli-responsive shape memory materials due to their unique reversible large-scale and high-speed actuations. These materials can be utilized to fabricate artificial muscles, sensors, and actuators driven by thermal order–disorder phase transition or transcis [...] Read more.
Liquid crystal polymers have attracted massive attention as stimuli-responsive shape memory materials due to their unique reversible large-scale and high-speed actuations. These materials can be utilized to fabricate artificial muscles, sensors, and actuators driven by thermal order–disorder phase transition or transcis photoisomerization. This review collects most commonly used liquid crystal monomers and techniques to macroscopically order and align liquid crystal materials (monodomain), highlighting the unique materials on the thermal and photo responsive reversible shape memory effects. Challenges and potential future applications are also discussed. Full article
(This article belongs to the Special Issue Advances in Shape Memory Polymers and Polymeric Nanocomposites)
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Article
Induction of Apoptosis by Gluconasturtiin-Isothiocyanate (GNST-ITC) in Human Hepatocarcinoma HepG2 Cells and Human Breast Adenocarcinoma MCF-7 Cells
Molecules 2020, 25(5), 1240; https://doi.org/10.3390/molecules25051240 - 09 Mar 2020
Cited by 5 | Viewed by 1544
Abstract
Gluconasturtiin, a glucosinolate present in watercress, is hydrolysed by myrosinase to form gluconasturtiin-isothiocyanate (GNST-ITC), which has potential chemopreventive effects; however, the underlying mechanisms of action have not been explored, mainly in human cell lines. The purpose of the study is to evaluate the [...] Read more.
Gluconasturtiin, a glucosinolate present in watercress, is hydrolysed by myrosinase to form gluconasturtiin-isothiocyanate (GNST-ITC), which has potential chemopreventive effects; however, the underlying mechanisms of action have not been explored, mainly in human cell lines. The purpose of the study is to evaluate the cytotoxicity of GNST-ITC and to further assess its potential to induce apoptosis. GNST-ITC inhibited cell proliferation in both human hepatocarcinoma (HepG2) and human breast adenocarcinoma (MCF-7) cells with IC50 values of 7.83 µM and 5.02 µM, respectively. Morphological changes as a result of GNST-ITC-induced apoptosis showed chromatin condensation, nuclear fragmentation, and membrane blebbing. Additionally, Annexin V assay showed proportion of cells in early and late apoptosis upon exposure to GNST-ITC in a time-dependent manner. To delineate the mechanism of apoptosis, cell cycle arrest and expression of caspases were studied. GNST-ITC induced a time-dependent G2/M phase arrest, with reduction of 82% and 93% in HepG2 and MCF-7 cell lines, respectively. The same treatment also led to the subsequent expression of caspase-3/7 and -9 in both cells demonstrating mitochondrial-associated cell death. Collectively, these results reveal that GNST-ITC can inhibit cell proliferation and can induce cell death in HepG2 and MCF-7 cancer cells via apoptosis, highlighting its potential development as an anticancer agent. Full article
(This article belongs to the Special Issue Biological Activity of Natural Substances and Their Derivatives)
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Review
Multitargeting Compounds: A Promising Strategy to Overcome Multi-Drug Resistant Tuberculosis
Molecules 2020, 25(5), 1239; https://doi.org/10.3390/molecules25051239 - 09 Mar 2020
Cited by 12 | Viewed by 1795
Abstract
Tuberculosis is still an urgent global health problem, mainly due to the spread of multi-drug resistant M. tuberculosis strains, which lead to the need of new more efficient drugs. A strategy to overcome the problem of the resistance insurgence could be the polypharmacology [...] Read more.
Tuberculosis is still an urgent global health problem, mainly due to the spread of multi-drug resistant M. tuberculosis strains, which lead to the need of new more efficient drugs. A strategy to overcome the problem of the resistance insurgence could be the polypharmacology approach, to develop single molecules that act on different targets. Polypharmacology could have features that make it an approach more effective than the classical polypharmacy, in which different drugs with high affinity for one target are taken together. Firstly, for a compound that has multiple targets, the probability of development of resistance should be considerably reduced. Moreover, such compounds should have higher efficacy, and could show synergic effects. Lastly, the use of a single molecule should be conceivably associated with a lower risk of side effects, and problems of drug–drug interaction. Indeed, the multitargeting approach for the development of novel antitubercular drugs have gained great interest in recent years. This review article aims to provide an overview of the most recent and promising multitargeting antitubercular drug candidates. Full article
(This article belongs to the Special Issue Recent Advances in Antitubercular Drug Discovery)
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Article
Variation Patterns of the Volatiles during Germination of the Foxtail Millet (Setaria Italic): The Relationship between the Volatiles and Fatty Acids in Model Experiments
Molecules 2020, 25(5), 1238; https://doi.org/10.3390/molecules25051238 - 09 Mar 2020
Cited by 6 | Viewed by 1271
Abstract
Functional and nutritional compounds are increased during foxtail millet germination while bad smell is produced due to the fatty acid oxidation. To eliminate the unpleasant aroma, the origins of the volatiles must be known. A comprehensive two-dimensional gas chromatography-time-of-flight mass spectrometry showed forty-nine [...] Read more.
Functional and nutritional compounds are increased during foxtail millet germination while bad smell is produced due to the fatty acid oxidation. To eliminate the unpleasant aroma, the origins of the volatiles must be known. A comprehensive two-dimensional gas chromatography-time-of-flight mass spectrometry showed forty-nine volatiles containing 8 ketones, 10 aldehydes, 20 alkanes, 4 alcohols, 5 alkenes, and 2 furans were tentatively identified, and they increased during the germination of the foxtail millet. To identify the origin of some volatiles, model experiments by adding 6 fatty acids to the crude enzymes of the foxtail millet was designed, and 17 volatiles could be detected. The saturated fatty acids (palmitic acid and stearic acid) had no contributions to the formation of the volatiles, whereas the unsaturated fatty acid played important roles in the formation of volatiles. Among the unsaturated fatty acids, palmitoleic acid and linoleic acid produced most aldehydes, alcohols, and ketones, while linolenic acid produced the most alkanes and alkenes. This study will be helpful for controlling the smell of germinated seeds from the raw material selection. Full article
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Article
HPLC-DAD-Guided Isolation of Diversified Chaetoglobosins from the Coral-Associated Fungus Chaetomium globosum C2F17
Molecules 2020, 25(5), 1237; https://doi.org/10.3390/molecules25051237 - 09 Mar 2020
Cited by 11 | Viewed by 1597
Abstract
Cytochalasans have continuously aroused considerable attention among the chemistry and pharmacology communities due to their structural complexities and pharmacological significances. Sixteen structurally diverse chaetoglobosins, 10-(indol-3-yl)-[13]cytochalasans, including a new one, 6-O-methyl-chaetoglobosin Q (1), were isolated from the coral-associated fungus Chaetomium [...] Read more.
Cytochalasans have continuously aroused considerable attention among the chemistry and pharmacology communities due to their structural complexities and pharmacological significances. Sixteen structurally diverse chaetoglobosins, 10-(indol-3-yl)-[13]cytochalasans, including a new one, 6-O-methyl-chaetoglobosin Q (1), were isolated from the coral-associated fungus Chaetomium globosum C2F17. Their structures were accomplished by extensive spectroscopic analysis combined with single-crystal X-ray crystallography and ECD calculations. Meanwhile, the structures and absolute configurations of the previously reported compounds 6, 12, and 13 were confirmed by single-crystal X-ray analysis for the first time. Chaetoglobosins E (6) and Fex (11) showed significant cytotoxicity against a panel of cancer cell lines, K562, A549, Huh7, H1975, MCF-7, U937, BGC823, HL60, Hela, and MOLT-4, with the IC50 values ranging from 1.4 μM to 9.2 μM. Full article
(This article belongs to the Special Issue Natural Products from Fungi)
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Article
Use of Oak and Cherry Wood Chips during Alcoholic Fermentation and the Maturation Process of Rosé Wines: Impact on Phenolic Composition and Sensory Profile
Molecules 2020, 25(5), 1236; https://doi.org/10.3390/molecules25051236 - 09 Mar 2020
Cited by 5 | Viewed by 1835
Abstract
There is a lack of knowledge about the use of different wood species on rosé wine production. Thus, this work focused on the impact of the addition of wood chips from oak and cherry trees during the alcoholic fermentation and maturation process on [...] Read more.
There is a lack of knowledge about the use of different wood species on rosé wine production. Thus, this work focused on the impact of the addition of wood chips from oak and cherry trees during the alcoholic fermentation and maturation process on rosé wine characteristics. Therefore, phenolic composition and sensory characteristics were monitored during the rosé wines’ production. The use of wood chips during alcoholic fermentation induced a significant increase of phenolic content in rosé musts. During rosé wine maturation, the wood chip contact induced significantly higher values of colored anthocyanins, color intensity, and polymeric pigments, and significantly lower values of color hue in the corresponding rosé wines. In terms of sensory profile, a tendency for lower scores of “overall appreciation” were attributed to control rosé wine, while significantly higher scores for “color intensity” descriptor were attributed to all rosé wines matured in contact with wood chips. For the majority of phenolic parameters and individual phenolic compounds quantified, a clear and specific influence of the use of oak and cherry wood chips was not detected, except for (+)-catechin, where the rosé wines produced in contact with cherry chips showed the highest values. This study provides relevant information for winemakers about the impact of the use of wood chips on rosé wine quality. Full article
(This article belongs to the Special Issue Alcoholic Beverages Aging Technologies)
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Article
Determination of the Metabolite Content of Brassica juncea Cultivars Using Comprehensive Two-Dimensional Liquid Chromatography Coupled with a Photodiode Array and Mass Spectrometry Detection
Molecules 2020, 25(5), 1235; https://doi.org/10.3390/molecules25051235 - 09 Mar 2020
Cited by 10 | Viewed by 1675
Abstract
Plant-based foods are characterized by significant amounts of bioactive molecules with desirable health benefits beyond basic nutrition. The Brassicaceae (Cruciferae) family consists of 350 genera; among them, Brassica is the most important one, which includes some crops and species of great worldwide economic [...] Read more.
Plant-based foods are characterized by significant amounts of bioactive molecules with desirable health benefits beyond basic nutrition. The Brassicaceae (Cruciferae) family consists of 350 genera; among them, Brassica is the most important one, which includes some crops and species of great worldwide economic importance. In this work, the metabolite content of three different cultivars of Brassica juncea, namely ISCI Top, “Broad-leaf,” and ISCI 99, was determined using comprehensive two-dimensional liquid chromatography coupled with a photodiode array and mass spectrometry detection. The analyses were carried out under reversed-phase conditions in both dimensions, using a combination of a 250-mm microbore cyano column and a 50-mm RP-Amide column in the first and second dimension (2D), respectively. A multi (three-step) segmented-in-fraction gradient for the 2D separation was advantageously investigated here for the first time, leading to the identification of 37 metabolites. In terms of resolving power, orthogonality values ranged from 62% to 69%, whereas the corrected peak capacity values were the highest for B. juncea ISCI Top (639), followed by B. juncea “Broad-leaf” (502). Regarding quantification, B. juncea cv. “Broad-leaf” presented the highest flavonoid content (1962.61 mg/kg) followed by B. juncea cv. ISCI Top (1002.03 mg/kg) and B. juncea cv. ISCI 99 (211.37 mg/kg). Full article
(This article belongs to the Special Issue Recent Advances in Food and Natural Product Analysis)
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Article
Surface Compositional Change of Iron Oxide Porous Nanorods: A Route for Tuning their Magnetic Properties
Molecules 2020, 25(5), 1234; https://doi.org/10.3390/molecules25051234 - 09 Mar 2020
Cited by 1 | Viewed by 1158
Abstract
The capability of synthesizing specific nanoparticles (NPs) by varying their shape, size and composition in a controlled fashion represents a typical set of engineering tools that tune the NPs magnetic response via their anisotropy. In particular, variations in NP composition mainly affect the [...] Read more.
The capability of synthesizing specific nanoparticles (NPs) by varying their shape, size and composition in a controlled fashion represents a typical set of engineering tools that tune the NPs magnetic response via their anisotropy. In particular, variations in NP composition mainly affect the magnetocrystalline anisotropy component, while the different magnetic responses of NPs with isotropic (i.e., spherical) or elongated shapes are mainly caused by changes in their shape anisotropy. In this context, we propose a novel route to obtain monodispersed, partially hollow magnetite nanorods (NRs) by colloidal synthesis, in order to exploit their shape anisotropy to increase the related coercivity; we then modify their composition via a cation exchange (CE) approach. The combination of a synthetic and post-synthetic approach on NRs gave rise to dramatic variations in their magnetic features, with the pores causing an initial magnetic hardening that was further enhanced by the post-synthetic introduction of a manganese oxide shell. Indeed, the coupling of the core and shell ferrimagnetic phases led to even harder magnetic NRs. Full article
(This article belongs to the Special Issue Advances in Metal Oxide Nanoparticles)
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Communication
Synthesis of Functionalized Indoles via Palladium-Catalyzed Cyclization of N-(2-allylphenyl) Benzamide: A Method for Synthesis of Indomethacin Precursor
Molecules 2020, 25(5), 1233; https://doi.org/10.3390/molecules25051233 - 09 Mar 2020
Cited by 5 | Viewed by 1810
Abstract
We developed an efficient method for synthesis of substituted N-benzoylindole via Pd(II)-catalyzed C–H functionalization of substituted N-(2-allylphenyl)benzamide. The reaction showed a broad substrate scope (including N-acetyl and N-Ts substrates) and substituted indoles were obtained in good to excellent yields. [...] Read more.
We developed an efficient method for synthesis of substituted N-benzoylindole via Pd(II)-catalyzed C–H functionalization of substituted N-(2-allylphenyl)benzamide. The reaction showed a broad substrate scope (including N-acetyl and N-Ts substrates) and substituted indoles were obtained in good to excellent yields. The most distinctive feature of this method lies in the high selectivity for N-benzoylindole over benzoxazine, and this is the first example of Pd(II)-catalyzed synthesis of substituted N-benzoylindole. Notably, this new method was applied for the synthesis of key intermediate of indomethacin. Full article
(This article belongs to the Special Issue Organic Synthesis via Transition Metal-Catalysis)
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Article
Development of the Method for Determination of Volatile Sulfur Compounds (VSCs) in Fruit Brandy with the Use of HS–SPME/GC–MS
Molecules 2020, 25(5), 1232; https://doi.org/10.3390/molecules25051232 - 09 Mar 2020
Cited by 11 | Viewed by 1726
Abstract
Volatile sulfur compounds (VSCs) play an important role in the aroma profile of fermented beverages. However, because of their low concentration in samples, their analysis is difficult. The headspace solid-phase microextraction (HS–SPME) technique coupled with gas chromatography and mass spectrometry (GC–MS) is one [...] Read more.
Volatile sulfur compounds (VSCs) play an important role in the aroma profile of fermented beverages. However, because of their low concentration in samples, their analysis is difficult. The headspace solid-phase microextraction (HS–SPME) technique coupled with gas chromatography and mass spectrometry (GC–MS) is one of the methods successfully used to identify VSCs in wine and beer samples. However, this method encounters more obstacles when spirit beverages are analyzed, as the ethanol content of the matrix decreases the method sensitivity. In this work, different conditions applied during HS–SPME/GC–MS analysis, namely: ethanol concentration, salt addition, time and temperature of extraction, as well as fiber coating, were evaluated in regard to 19 sulfur compounds. The best results were obtained when 50/30 μm Divinylbenzene/Carboxen/Polydimethylsiloxane (DVB/CAR/PDMS) was used to preconcentrate the analytes from the sample at 35 °C for 30 min. The dilution of samples to 2.5% v/v ethanol and the addition of 20% w/v NaCl along with 1% EDTA significantly improves the sensitivity of extraction. The optimized method was applied to three fruit brandy samples (plum, pear, and apple) and quantification of VSCs was performed. A total of 10 compounds were identified in brandy samples and their concentration varied greatly depending on the raw material used from production. The highest concentration of identified VSCs was found in apple brandy (82 µg/L). Full article
(This article belongs to the Special Issue Bioactives and Functional Ingredients in Foods and Beverages)
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Article
Incorporation of Lutein on Layered Double Hydroxide for Improving the Environmental Stability
Molecules 2020, 25(5), 1231; https://doi.org/10.3390/molecules25051231 - 09 Mar 2020
Cited by 10 | Viewed by 1259
Abstract
To overcome the poor stability of natural lutein to environmental factors, layered double hydroxide was incorporated by a green mechanical grinding process. The influences of external factors (chemical reagents, heating and light) on the stability of lutein before and after being loaded were [...] Read more.
To overcome the poor stability of natural lutein to environmental factors, layered double hydroxide was incorporated by a green mechanical grinding process. The influences of external factors (chemical reagents, heating and light) on the stability of lutein before and after being loaded were evaluated. The results confirmed that lutein was mainly adsorbed on the surface of layered double hydroxide (LDH) via the chemical interaction. Compared with pure lutein, the thermal decomposition of lutein/LDH was improved from 100 °C to 300 °C, and the retention ratio of lutein was increased by about 8.64% and 21.47% after 96 h of light exposure and accelerated degradation, respectively. It is expected that the stable lutein/LDH composites may constitutean additive in animal feed. Full article
(This article belongs to the Section Colorants)
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Article
Melatonin Promotes the Proliferation of Chicken Sertoli Cells by Activating the ERK/Inhibin Alpha Subunit Signaling Pathway
Molecules 2020, 25(5), 1230; https://doi.org/10.3390/molecules25051230 - 09 Mar 2020
Cited by 5 | Viewed by 1256
Abstract
Melatonin influences physiological processes such as promoting proliferation and regulating cell development and function, and its effects on chicken Sertoli cells are unknown. Therefore, we investigated the effects of melatonin on cell proliferation and its underlying mechanisms in chicken Sertoli cells. Chicken Sertoli [...] Read more.
Melatonin influences physiological processes such as promoting proliferation and regulating cell development and function, and its effects on chicken Sertoli cells are unknown. Therefore, we investigated the effects of melatonin on cell proliferation and its underlying mechanisms in chicken Sertoli cells. Chicken Sertoli cells were exposed to varying melatonin concentrations (1, 10, 100, and 1000 nM), and the melatonin-induced effects on cell proliferation were measured by Cell Counting Kit 8 (CCK-8), 5-ethynyl-2’-deoxyuridine (EdU), real-time qPCR, and western blotting. We found that 1000 nM melatonin significantly (p < 0.05) promoted cell proliferation in chicken Sertoli cells. Furthermore, melatonin significantly (p < 0.05) increased the expression of inhibin alpha subunit (INHA), and the silencing of INHA reversed the melatonin-induced effects on Sertoli cell proliferation. We also found that melatonin activates the extracellular-regulated protein kinase (ERK) signaling pathway. To explore the role of the ERK signaling pathway in melatonin-induced cell proliferation, PD98059 (an inhibitor of EKR1/2) was used to pre-treat chicken Sertoli cells. The melatonin-induced proliferation of chicken Sertoli cells was reversed by PD98059, with decreased cell viability, weakened cell proliferation, and down-regulated expression of the proliferating cell nuclear antigen (PCNA), cyclin D1 (CCND1) and INHA. In summary, our results indicate that melatonin promotes the proliferation of chicken Sertoli cells by activating the ERK/inhibin alpha subunit signaling pathway. Full article
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Article
Sanguinarine Induces Apoptosis in Papillary Thyroid Cancer Cells via Generation of Reactive Oxygen Species
Molecules 2020, 25(5), 1229; https://doi.org/10.3390/molecules25051229 - 09 Mar 2020
Cited by 10 | Viewed by 2028
Abstract
Sanguinarine (SNG), a natural compound with an array of pharmacological activities, has promising therapeutic potential against a number of pathological conditions, including malignancies. In the present study, we have investigated the antiproliferative potential of SNG against two well-characterized papillary thyroid cancer (PTC) cell [...] Read more.
Sanguinarine (SNG), a natural compound with an array of pharmacological activities, has promising therapeutic potential against a number of pathological conditions, including malignancies. In the present study, we have investigated the antiproliferative potential of SNG against two well-characterized papillary thyroid cancer (PTC) cell lines, BCPAP and TPC-1. SNG significantly inhibited cell proliferation of PTC cells in a dose and time-dependent manner. Western blot analysis revealed that SNG markedly attenuated deregulated expression of p-STAT3, without affecting total STAT3, and inhibited growth of PTC via activation of apoptotic and autophagy signaling cascade, as SNG treatment of PTC cells led to the activation of caspase-3 and caspase-8; cleavage of PARP and activation of autophagy markers. Further, SNG-mediated anticancer effects in PTC cells involved the generation of reactive oxygen species (ROS) as N-acetyl cysteine (NAC), an inhibitor of ROS, prevented SNG-mediated antiproliferative, apoptosis and autophagy inducing action. Interestingly, SNG also sensitized PTC cells to chemotherapeutic drug cisplatin, which was inhibited by NAC. Finally, SNG suppressed the growth of PTC thyrospheres and downregulated stemness markers ALDH2 and SOX2. Altogether, the findings of the current study suggest that SNG has anticancer potential against PTC cells as well its derived cancer stem-like cells, most likely via inactivation of STAT3 and its associated signaling molecules. Full article
(This article belongs to the Special Issue Bioactive Natural Compounds and Their Mechanisms of Action)
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Article
Metabolomics Combined with Multivariate Statistical Analysis for Screening of Chemical Markers between Gentiana scabra and Gentiana rigescens
Molecules 2020, 25(5), 1228; https://doi.org/10.3390/molecules25051228 - 09 Mar 2020
Cited by 5 | Viewed by 1566
Abstract
Gentianae Radix et Rhizome (Longdan in Chinese, GRR) in Chinese Pharmacopoeia is derived from the dried roots and rhizomes of Gentiana scabra and G. rigescens, that have long been used for heat-clearing and damp-drying in the medicinal history of China. However, the [...] Read more.
Gentianae Radix et Rhizome (Longdan in Chinese, GRR) in Chinese Pharmacopoeia is derived from the dried roots and rhizomes of Gentiana scabra and G. rigescens, that have long been used for heat-clearing and damp-drying in the medicinal history of China. However, the characterization of the chemical components of two species and the screening of chemical markers still remain unsolved. In current research, the identification and characterization of chemical components of two species was performed using ultra-high-performance liquid chromatography (UHPLC) coupled with linear ion trap-Orbitrap (LTQ-Orbitrap) mass spectrometry. Subsequently, the chemical markers of two species were screened based on metabolomics and multivariate statistical analysis. In total, 87 chemical constituents were characterized in G. scabra (65 chemical constituents) and G. rigescens (51 chemical constituents), with 29 common chemical constituents being discovered. Thereafter, 11 differential characteristic components which could differentiate the two species were designated with orthogonal partial least squares discriminant analysis (OPLS-DA) and random forest (RF) iterative modeling. Finally, seven characteristic components identified as (+)-syringaresinol, lutonarin, trifloroside, 4-O-β-d-glu-trifloroside, 4″-O-β-d-glucopyranosy1-6′-O-(4-O-β-d-glucaffeoyl)-linearroside, macrophylloside a and scabraside were selected as the chemical markers for the recognition of two Gentiana species. It was implied that the results could distinguish the GRR derived from different botanical sources, and also be beneficial in the rational clinical use of GRR. Full article
(This article belongs to the Section Analytical Chemistry)
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