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Molecules, Volume 22, Issue 2 (February 2017)

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Cover Story (view full-size image) The immense scope for variation in dendritic molecules and their versatile functionalization, with [...] Read more.
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Open AccessArticle Design, Synthesis and Evaluation of Naphthalimide Derivatives as Potential Anticancer Agents for Hepatocellular Carcinoma
Molecules 2017, 22(2), 342; https://doi.org/10.3390/molecules22020342
Received: 13 January 2017 / Revised: 16 February 2017 / Accepted: 16 February 2017 / Published: 22 February 2017
Cited by 4 | PDF Full-text (2893 KB) | HTML Full-text | XML Full-text
Abstract
Two kinds of naphthalimide derivatives were synthesized and evaluated for in vitro their anti-hepatocellular carcinoma properties. Compound 3a with a fused thiazole fragment to naphthalimide skeleton inhibited cell migration of SMMC-7721 and HepG2, and further in vivo trials with two animal models confirmed
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Two kinds of naphthalimide derivatives were synthesized and evaluated for in vitro their anti-hepatocellular carcinoma properties. Compound 3a with a fused thiazole fragment to naphthalimide skeleton inhibited cell migration of SMMC-7721 and HepG2, and further in vivo trials with two animal models confirmed that compound 3a moderately inhibited primary H22 tumor growth (52.6%) and potently interrupted lung metastasis (75.7%) without obvious systemic toxicity at the therapeutic dose. Mechanistic research revealed that compound 3a inhibited cancerous liver cell growth mostly by inducing G2/M phase arrest. Western blotting experiments corroborated that 3a could up-regulate the cell cycle related protein expression of cyclin B1, CDK1 and p21, and inhibit cell migration by elevating the E-cadherin and attenuating integrin α6 expression. Our study showed that compound 3a is a valuable lead compound worthy of further investigation. Full article
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Open AccessArticle Lycium barbarum L. Polysaccharide (LBP) Reduces Glucose Uptake via Down-Regulation of SGLT-1 in Caco2 Cell
Molecules 2017, 22(2), 341; https://doi.org/10.3390/molecules22020341
Received: 30 December 2016 / Revised: 2 February 2017 / Accepted: 13 February 2017 / Published: 22 February 2017
Cited by 7 | PDF Full-text (6551 KB) | HTML Full-text | XML Full-text
Abstract
Lycium barbarum L. polysaccharide (LBP) is prepared from Lycium barbarum L. (L. barbarum), which is a traditional Chinese medicine. LPB has been shown to have hypoglycemic effects. In order to gain some mechanistic insights on the hypoglycemic effects of LBP, we
[...] Read more.
Lycium barbarum L. polysaccharide (LBP) is prepared from Lycium barbarum L. (L. barbarum), which is a traditional Chinese medicine. LPB has been shown to have hypoglycemic effects. In order to gain some mechanistic insights on the hypoglycemic effects of LBP, we investigated the uptake of LBP and its effect on glucose absorption in the human intestinal epithelial cell line Caco2 cell. The uptake of LBP through Caco2 cell monolayer was time-dependent and was inhibited by phloridzin, a competitive inhibitor of SGLT-1. LPB decreased the absorption of glucose in Caco2 cell, and down-regulated the expression of SGLT-1. These results suggest that LBP might be transported across the human intestinal epithelium through SGLT-1 and it inhibits glucose uptake via down-regulating SGLT-1. Full article
(This article belongs to the Special Issue Natural Polysaccharides)
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Open AccessReview Recent Advances and Applications of Molecular Docking to G Protein-Coupled Receptors
Molecules 2017, 22(2), 340; https://doi.org/10.3390/molecules22020340
Received: 12 December 2016 / Revised: 27 January 2017 / Accepted: 15 February 2017 / Published: 22 February 2017
Cited by 5 | PDF Full-text (873 KB) | HTML Full-text | XML Full-text
Abstract
The growing number of studies on G protein-coupled receptors (GPCRs) family are a source of noticeable improvement in our understanding of the functioning of these proteins. GPCRs are responsible for a vast part of signaling in vertebrates and, as such, invariably remain in
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The growing number of studies on G protein-coupled receptors (GPCRs) family are a source of noticeable improvement in our understanding of the functioning of these proteins. GPCRs are responsible for a vast part of signaling in vertebrates and, as such, invariably remain in the spotlight of medicinal chemistry. A deeper insight into the underlying mechanisms of interesting phenomena observed in GPCRs, such as biased signaling or allosteric modulation, can be gained with experimental and computational studies. The latter play an important role in this process, since they allow for observations on scales inaccessible for most other methods. One of the key steps in such studies is proper computational reconstruction of actual ligand-receptor or protein-protein interactions, a process called molecular docking. A number of improvements and innovative applications of this method were documented recently. In this review, we focus particularly on innovations in docking to GPCRs. Full article
(This article belongs to the collection Molecular Docking)
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Open AccessArticle Immobilization of Lipase from Penicillium sp. Section Gracilenta (CBMAI 1583) on Different Hydrophobic Supports: Modulation of Functional Properties
Molecules 2017, 22(2), 339; https://doi.org/10.3390/molecules22020339
Received: 10 December 2016 / Revised: 14 February 2017 / Accepted: 14 February 2017 / Published: 22 February 2017
Cited by 5 | PDF Full-text (944 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Lipases are promising enzymes that catalyze the hydrolysis of triacylglycerol ester bonds at the oil/water interface. Apart from allowing biocatalyst reuse, immobilization can also affect enzyme structure consequently influencing its activity, selectivity, and stability. The lipase from Penicillium sp. section Gracilenta (CBMAI 1583)
[...] Read more.
Lipases are promising enzymes that catalyze the hydrolysis of triacylglycerol ester bonds at the oil/water interface. Apart from allowing biocatalyst reuse, immobilization can also affect enzyme structure consequently influencing its activity, selectivity, and stability. The lipase from Penicillium sp. section Gracilenta (CBMAI 1583) was successfully immobilized on supports bearing butyl, phenyl, octyl, octadecyl, and divinylbenzyl hydrophobic moieties wherein lipases were adsorbed through the highly hydrophobic opened active site. The highest activity in aqueous medium was observed for the enzyme adsorbed on octyl support, with a 150% hyperactivation regarding the soluble enzyme activity, and the highest adsorption strength was verified with the most hydrophobic support (octadecyl Sepabeads), requiring 5% Triton X-100 to desorb the enzyme from the support. Most of the derivatives presented improved properties such as higher stability to pH, temperature, and organic solvents than the covalently immobilized CNBr derivative (prepared under very mild experimental conditions and thus a reference mimicking free-enzyme behavior). A 30.8- and 46.3-fold thermostabilization was achieved in aqueous medium, respectively, by the octyl Sepharose and Toyopearl butyl derivatives at 60 °C, in relation to the CNBr derivative. The octyl- and phenyl-agarose derivatives retained 50% activity after four and seven cycles of p-nitrophenyl palmitate hydrolysis, respectively. Different derivatives exhibited different properties regarding their properties for fish oil hydrolysis in aqueous medium and ethanolysis in anhydrous medium. The most active derivative in ethanolysis of fish oil was the enzyme adsorbed on a surface covered by divinylbenzyl moieties and it was 50-fold more active than the enzyme adsorbed on octadecyl support. Despite having identical mechanisms of immobilization, different hydrophobic supports seem to promote different shapes of the adsorbed open active site of the lipase and hence different functional properties. Full article
(This article belongs to the Special Issue Enzyme Immobilization 2016)
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Open AccessArticle Synthesis of Reusable Silica Nanosphere-Supported Pt(IV) Complex for Formation of Disulfide Bonds in Peptides
Molecules 2017, 22(2), 338; https://doi.org/10.3390/molecules22020338
Received: 11 December 2016 / Revised: 10 February 2017 / Accepted: 16 February 2017 / Published: 22 February 2017
Cited by 1 | PDF Full-text (8965 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Some peptide-based drugs, including oxytocin, vasopressin, ziconotide, pramlintide, nesiritide, and octreotide, contain one intramolecular disulfide bond. A novel and reusable monodispersed silica nanosphere-supported Pt(IV) complex (SiO2@TPEA@Pt(IV)); TPEA: N-[3-(trimethoxysilyl)propyl]ethylenediamine) was synthesized via a four-step procedure and was used for the formation
[...] Read more.
Some peptide-based drugs, including oxytocin, vasopressin, ziconotide, pramlintide, nesiritide, and octreotide, contain one intramolecular disulfide bond. A novel and reusable monodispersed silica nanosphere-supported Pt(IV) complex (SiO2@TPEA@Pt(IV)); TPEA: N-[3-(trimethoxysilyl)propyl]ethylenediamine) was synthesized via a four-step procedure and was used for the formation of intramolecular disulfide bonds in peptides. Transmission electron microscopy (TEM) and chemical mapping results for the Pt(II) intermediates and for SiO2@TPEA@Pt(IV) show that the silica nanospheres possess a monodisperse spherical structure and contain uniformly-distributed Si, O, C, N, Cl, and Pt. The valence state of Pt on the silica nanospheres was characterized by X-ray photoelectron spectroscopy (XPS). The Pt(IV) loaded on SiO2@TPEA@Pt(IV) was 0.15 mmol/g, as determined by UV-VIS spectrometry. The formation of intramolecular disulfides in six dithiol-containing peptides of variable lengths by the use of SiO2@TPEA@Pt(IV) was investigated, and the relative oxidation yields were determined by high-performance liquid chromatography (HPLC). In addition, peptide 1 (Ac-CPFC-NH2) was utilized to study the reusability of SiO2@TPEA@Pt(IV). No significant decrease in the relative oxidation yield was observed after ten reaction cycles. Moreover, the structure of SiO2@TPEA@Pt(IV) after being used for ten cycles was determined to be similar to its initial one, demonstrating the cycling stability of the complex. Full article
(This article belongs to the Section Organic Chemistry)
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Open AccessArticle A Photocatalytic Rotating Disc Reactor with TiO2 Nanowire Arrays Deposited for Industrial Wastewater Treatment
Molecules 2017, 22(2), 337; https://doi.org/10.3390/molecules22020337
Received: 12 December 2016 / Revised: 6 February 2017 / Accepted: 14 February 2017 / Published: 22 February 2017
Cited by 2 | PDF Full-text (16869 KB) | HTML Full-text | XML Full-text
Abstract
A photocatalytic rotating disc reactor (PRD-reactor) with TiO2 nanowire arrays deposited on a thin Ti plate is fabricated and tested for industrial wastewater treatment. Results indicate that the PRD-reactor shows excellent decolorization capability when tested with methyl orange (>97.5%). Advanced oxidation processes
[...] Read more.
A photocatalytic rotating disc reactor (PRD-reactor) with TiO2 nanowire arrays deposited on a thin Ti plate is fabricated and tested for industrial wastewater treatment. Results indicate that the PRD-reactor shows excellent decolorization capability when tested with methyl orange (>97.5%). Advanced oxidation processes (AOP), including photocatalytic oxidation and photolytic reaction, occurred during the processing. Efficiency of the AOP increases with reduction in light absorption pathlength, which enhanced the photocatalytic reaction, as well as by increasing oxygen exposure of the wastewater thin film due to the rotating disc design. It is found that, with a small dosage of hydrogen peroxide, the mineralization efficiency of industrial biodegraded wastewater can be enhanced, with a superior mineralization of >75% total organic carbon (TOC) removal. This is due to the fact that the TiO2 photocatalysis and hydrogen peroxide processes generate powerful oxidants (hydroxyl radicals) that can strongly improve photocatalytic oxidation efficiency. Application of this industrial wastewater treatment system is benefited from the TiO2 nanowire arrays, which can be fabricated by a mild solvothermal method at 80 °C and under atmospheric pressure. Similar morphologies and microstructures are found for the TiO2 nanowire arrays deposited on a large metal Ti disc, which makes the wastewater treatment process more practical and economical. Full article
(This article belongs to the Special Issue Solar Photocatalysis)
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Open AccessArticle Diastereoselective Synthesis of Spirocyclopropanes under Mild Conditions via Formal [2 + 1] Cycloadditions Using 2,3-Dioxo-4-benzylidene-pyrrolidines
Molecules 2017, 22(2), 328; https://doi.org/10.3390/molecules22020328
Received: 16 January 2017 / Revised: 14 February 2017 / Accepted: 16 February 2017 / Published: 22 February 2017
Cited by 1 | PDF Full-text (2243 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
A highly diastereoselective cyclopropanation of cyclic enones with sulfur ylides was developed under catalyst-free conditions, producing multifunctional spirocyclopropanes in generally excellent yields (up to 99% yield and >99:1 d.r.). The asymmetric version of this method was realized by using an easily available chiral
[...] Read more.
A highly diastereoselective cyclopropanation of cyclic enones with sulfur ylides was developed under catalyst-free conditions, producing multifunctional spirocyclopropanes in generally excellent yields (up to 99% yield and >99:1 d.r.). The asymmetric version of this method was realized by using an easily available chiral sulfur ylide, affording products with moderate to good stereoselectivity. Full article
(This article belongs to the collection Heterocyclic Compounds)
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Open AccessArticle A Study on the Electro-Optical Properties of Thiol-Ene Polymer Dispersed Cholesteric Liquid Crystal (PDChLC) Films
Molecules 2017, 22(2), 317; https://doi.org/10.3390/molecules22020317
Received: 1 December 2016 / Revised: 2 February 2017 / Accepted: 9 February 2017 / Published: 22 February 2017
Cited by 2 | PDF Full-text (4582 KB) | HTML Full-text | XML Full-text
Abstract
In this study, a polymer dispersed cholesteric liquid crystal (PDChLC) film obtained via a one-step fabrication technique based on photopolymerization of a thiol-acrylate reaction system was prepared and characterized for the first time. The effects of the chiral dopant, the influence of thiol
[...] Read more.
In this study, a polymer dispersed cholesteric liquid crystal (PDChLC) film obtained via a one-step fabrication technique based on photopolymerization of a thiol-acrylate reaction system was prepared and characterized for the first time. The effects of the chiral dopant, the influence of thiol monomer functionality and content on the morphology and subsequent performance of the PDChLC films were systematically investigated. It was demonstrated that the addition of a small amount of chiral dopant slightly increased the driving voltage, but decreased the off-state transmittance significantly. Furthermore, scanning electron micrographs (SEM) shown that the liquid crystal (LC) droplet size decreased at first and then increased with the increasing amount of thiol monomer functionality, while increasing the thiol content increased the LC droplet size. Correspondingly, the electro-optical switching behavior was directly dependent on LC droplet size. By tuning the raw material composition, PDChLC film with optimized electro-optical performance was prepared. Full article
(This article belongs to the Special Issue Advances in Organic Nanophotonics)
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Open AccessArticle Immobilized Trienzymatic System with Enhanced Stabilization for the Biotransformation of Lactose
Molecules 2017, 22(2), 284; https://doi.org/10.3390/molecules22020284
Received: 29 November 2016 / Revised: 7 February 2017 / Accepted: 8 February 2017 / Published: 22 February 2017
Cited by 1 | PDF Full-text (1467 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
The use of ketohexose isomerases is a powerful tool in lactose whey processing, but these enzymes can be very sensitive and expensive. Development of immobilized/stabilized biocatalysts could be a further option to improve the process. In this work, β-galactosidase from Bacillus circulans,
[...] Read more.
The use of ketohexose isomerases is a powerful tool in lactose whey processing, but these enzymes can be very sensitive and expensive. Development of immobilized/stabilized biocatalysts could be a further option to improve the process. In this work, β-galactosidase from Bacillus circulans, l-arabinose (d-galactose) isomerase from Enterococcus faecium, and d-xylose (d-glucose) isomerase from Streptomyces rubiginosus were immobilized individually onto Eupergit C and Eupergit C 250 L. Immobilized activity yields were over 90% in all cases. With the purpose of increasing thermostability of derivatives, two post-immobilization treatments were performed: alkaline incubation to favor the formation of additional covalent linkages, and blocking of excess oxirane groups by reacting with glycine. The greatest thermostability was achieved when alkaline incubation was carried out for 24 h, producing l-arabinose isomerase-Eupergit C derivatives with a half-life of 379 h and d-xylose isomerase-Eupergit C derivatives with a half-life of 554 h at 50 °C. Preliminary assays using immobilized and stabilized biocatalysts sequentially to biotransform lactose at pH 7.0 and 50 °C demonstrated improved performances as compared with soluble enzymes. Further improvements in ketohexose productivities were achieved when the three single-immobilizates were incubated simultaneously with lactose in a mono-reactor system. Full article
(This article belongs to the Special Issue Enzyme Immobilization 2016)
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Open AccessArticle Synthesis, Characterization and Antibacterial Studies of N-(Benzothiazol-2-yl)-4-chlorobenzenesulphonamide and Its Neodymium(III) and Thallium(III) Complexes
Molecules 2017, 22(2), 153; https://doi.org/10.3390/molecules22020153
Received: 9 November 2016 / Revised: 4 January 2017 / Accepted: 4 January 2017 / Published: 22 February 2017
Cited by 1 | PDF Full-text (3711 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
N-(Benzothiazol-2-yl)-4-chlorobenzenesulphonamide (NBTCS) was synthesized by condensation reaction of 4-chlorobenzenesulphonyl chloride and 2-aminobenzothiazole in acetone under reflux. Neodymium(III) and thallium(III) complexes of the ligand were also synthesized. Both ligand and metal complexes were characterized using UV-Vis, IR, 1H- and 13C-NMR spectroscopies,
[...] Read more.
N-(Benzothiazol-2-yl)-4-chlorobenzenesulphonamide (NBTCS) was synthesized by condensation reaction of 4-chlorobenzenesulphonyl chloride and 2-aminobenzothiazole in acetone under reflux. Neodymium(III) and thallium(III) complexes of the ligand were also synthesized. Both ligand and metal complexes were characterized using UV-Vis, IR, 1H- and 13C-NMR spectroscopies, elemental analysis and molar conductance measurement. IR studies revealed that the ligand is tridentate and coordinates to the metal ions through nitrogen and oxygen atoms of the sulphonamide group and nitrogen atom attached to benzothiazole ring. The neodymium(III) complex displays a coordination number of eight while thallium(III) complex displays a coordination number of six. The ligand and its complexes were screened in vitro for their antibacterial activities against Escherichia coli strains (E. coli 6 and E. coli 13), Proteus species, Staphylococcus aureus and Pseudomonas aeruginosa using the agar well diffusion technique. The synthesized compounds were found to be more active against the microorganisms screened relative to ciprofloxacin, gentamicin and co-trimoxazole. Full article
(This article belongs to the Special Issue Sulfur-Nitrogen Heteroaromatics)
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Open AccessArticle New Route Synthesis of Thiadiazoles, Bisthiadiazoles, Thiadiazolotriazines, and Pyrazolothiadiazoles Based on Hydrazonoyl Halides and Dihydrazinylthiadiazole
Molecules 2017, 22(2), 336; https://doi.org/10.3390/molecules22020336
Received: 1 January 2017 / Accepted: 15 February 2017 / Published: 21 February 2017
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Abstract
Synthesis and characterization of new thiadiazoles, bisthiadiazoles from the reaction of mono- and di-hydrazonoyl halides with various hydrazinecarbodithioate derivatives were studied. Treatment of hydrazonoyl halides with 2,5-dihydrazinyl-1,3,4-thiadiazole afforded new bistriazines containing thiadiazole; we also examined the reaction of 2,5-dihydrazinyl-1,3,4-thiadiazole with active methylene compounds
[...] Read more.
Synthesis and characterization of new thiadiazoles, bisthiadiazoles from the reaction of mono- and di-hydrazonoyl halides with various hydrazinecarbodithioate derivatives were studied. Treatment of hydrazonoyl halides with 2,5-dihydrazinyl-1,3,4-thiadiazole afforded new bistriazines containing thiadiazole; we also examined the reaction of 2,5-dihydrazinyl-1,3,4-thiadiazole with active methylene compounds to afford new pyrazoles containing thiadiazole compounds. The new synthesized compounds were identified by elemental analysis and various spectral data (Fourier transform infrared spectroscopy, mass spectrometry, 1H and 13C nuclear magnetic resonance). Full article
(This article belongs to the Special Issue Sulfur-Nitrogen Heteroaromatics)
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Open AccessArticle One-Pot Conversion of Epoxidized Soybean Oil (ESO) into Soy-Based Polyurethanes by MoCl2O2 Catalysis
Molecules 2017, 22(2), 333; https://doi.org/10.3390/molecules22020333
Received: 14 January 2017 / Revised: 16 February 2017 / Accepted: 17 February 2017 / Published: 21 February 2017
Cited by 3 | PDF Full-text (2315 KB) | HTML Full-text | XML Full-text
Abstract
An innovative and eco-friendly one-pot synthesis of bio-based polyurethanes is proposed via the epoxy-ring opening of epoxidized soybean oil (ESO) with methanol, followed by the reaction of methoxy bio-polyols intermediates with 2,6-tolyl-diisocyanate (TDI). Both synthetic steps, methanolysis and polyurethane linkage formation, are promoted
[...] Read more.
An innovative and eco-friendly one-pot synthesis of bio-based polyurethanes is proposed via the epoxy-ring opening of epoxidized soybean oil (ESO) with methanol, followed by the reaction of methoxy bio-polyols intermediates with 2,6-tolyl-diisocyanate (TDI). Both synthetic steps, methanolysis and polyurethane linkage formation, are promoted by a unique catalyst, molybdenum(VI) dichloride dioxide (MoCl2O2), which makes this procedure an efficient, cost-effective, and environmentally safer method amenable to industrial scale-up. Full article
(This article belongs to the Section Organic Chemistry)
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Open AccessArticle Evaluation of Extraction and Degradation Methods to Obtain Chickpeasaponin B1 from Chickpea (Cicer arietinum L.)
Molecules 2017, 22(2), 332; https://doi.org/10.3390/molecules22020332
Received: 19 January 2017 / Revised: 15 February 2017 / Accepted: 17 February 2017 / Published: 21 February 2017
Cited by 3 | PDF Full-text (3982 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
The objective of this research is to implement extraction and degradation methods for the obtainment of 3-O-[α-l-rhamnopyranosyl-(1→2)-β-d-galactopyranosyl] soyasapogenol B (chickpeasaponin B1) from chickpea. The effects of microwave-assisted extraction (MAE) processing parameters—such as ethanol concentration, solvent/solid ratio, extraction
[...] Read more.
The objective of this research is to implement extraction and degradation methods for the obtainment of 3-O-[α-l-rhamnopyranosyl-(1→2)-β-d-galactopyranosyl] soyasapogenol B (chickpeasaponin B1) from chickpea. The effects of microwave-assisted extraction (MAE) processing parameters—such as ethanol concentration, solvent/solid ratio, extraction temperature, microwave irradiation power, and irradiation time—were evaluated. Using 1g of material with 8 mL of 70% aqueous ethanol and an extraction time of 10 min at 70 °C under irradiation power 400W provided optimal extraction conditions. Compared with the conventional extraction techniques, including heat reflux extraction (HRE), Soxhlet extraction (SE), and ultrasonic extraction (UE), MAE produced higher extraction efficiency under a lower extraction time. DDMP (2,3-dihydro-2,5-dihydroxy-6-methyl-4H-pyran-4-one) saponin can be degraded to structurally stable saponin B by the loss of its DDMP group. The influence of pH and the concentration of potassium hydroxide on transformation efficiency of the target compound was investigated. A solution of 0.25 M potassium hydroxide in 75% aqueous ethanol was suitable for converting the corresponding DDMP saponins of chickpeasaponin B1. The implementation by the combining MAE technique and alkaline hydrolysis method for preparing chickpeasaponin B1 provides a convenient technology for future applications. Full article
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Open AccessArticle ZYZ-772 Prevents Cardiomyocyte Injury by Suppressing Nox4-Derived ROS Production and Apoptosis
Molecules 2017, 22(2), 331; https://doi.org/10.3390/molecules22020331
Received: 16 January 2017 / Revised: 10 February 2017 / Accepted: 13 February 2017 / Published: 21 February 2017
Cited by 3 | PDF Full-text (3502 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Nox-dependent signaling plays critical roles in the development of heart failure, cardiac hypertrophy, and myocardial infarction. NADPH oxidase 4 (Nox4) as a major source of oxidative stress in the heart offers a new therapeutic target in cardiovascular disease. In the present work, a
[...] Read more.
Nox-dependent signaling plays critical roles in the development of heart failure, cardiac hypertrophy, and myocardial infarction. NADPH oxidase 4 (Nox4) as a major source of oxidative stress in the heart offers a new therapeutic target in cardiovascular disease. In the present work, a novel flavonoid was isolated from Zanthoxylum bungeanum. Its structure was elucidated as Quercetin-3-O-(6′′-O-α-l-rhamnopyransoyl)-β-d-glucopyranoside-7-O-β-d-glucopyranoside (ZYZ-772) for the first time. ZYZ-772 exhibited significant cardio-protective property against CoCl2 induced H9c2 cardiomyocyte cells injury. In CoCl2 stimulated cardiomyocyte injury, ZYZ-772 inhibited expression of Nox4, and alleviated ROS overproduction. Importantly, ROS triggered MAPKs phosphorylation and P53 signaling mediated apoptosis were restored by ZYZ-772. Our findings present the first piece of evidence for the therapeutic properties of ZYZ-772 in preventing cardiomyocyte injury, which could be attributed to the suppression of Nox4/MAPKs/P53 axis. This will offer a novel therapeutic strategy for the treatment of cardiac ischemia disease. Full article
(This article belongs to the Special Issue Natural Product: A Continuing Source of Novel Drug Leads)
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Open AccessArticle Metabolic Profiling and Identification of Shikonins in Root Periderm of Two Invasive Echium spp. Weeds in Australia
Molecules 2017, 22(2), 330; https://doi.org/10.3390/molecules22020330
Received: 17 December 2016 / Revised: 13 February 2017 / Accepted: 15 February 2017 / Published: 21 February 2017
Cited by 2 | PDF Full-text (1910 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Metabolic profiling can be successfully implemented to analyse a living system’s response to environmental conditions by providing critical information on an organism’s physiological state at a particular point in time and allowing for both quantitative and qualitative assessment of a specific subset(s) of
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Metabolic profiling can be successfully implemented to analyse a living system’s response to environmental conditions by providing critical information on an organism’s physiological state at a particular point in time and allowing for both quantitative and qualitative assessment of a specific subset(s) of key metabolites. Shikonins are highly reactive chemicals that affect various cell signalling pathways and possess antifungal, antibacterial and allelopathic activity. Based on previous bioassay results, bioactive shikonins, are likely to play important roles in the regulation of rhizosphere interactions with neighbouring plants, microbes and herbivores. An effective platform allowing for rapid identification and accurate profiling of numerous structurally similar, difficult-to-separate bioactive isohexenylnaphthazarins (shikonins) was developed using UHPLC Q-TOF MS. Root periderm tissues of the invasive Australian weeds Echium plantagineum and its congener E. vulgare were extracted overnight in ethanol for shikonin profiling. Shikonin production was evaluated at seedling, rosette and flowering stages. Five populations of each species were compared for qualitative and quantitative differences in shikonin formation. Each species showed little populational variation in qualitative shikonin production; however, shikonin was considerably low in one population of E. plantagineum from Western New South Wales. Seedlings of all populations produced the bioactive metabolite acetylshikonin and production was upregulated over time. Mature plants of both species produced significantly higher total levels of shikonins and isovalerylshikonin > dimethylacrylshikonin > shikonin > acetylshikonin in mature E. plantagineum. Although qualitative metabolic profiles in both Echium spp. were nearly identical, shikonin abundance in mature plant periderm was approximately 2.5 times higher in perennial E. vulgare extracts in comparison to those of the annual E. plantagineum. These findings contribute to our understanding of the biosynthesis of shikonins in roots of two related invasive plants and their expression in relation to plant phenological stage. Full article
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Open AccessArticle Preparation of Photoirradiation Molecular Imprinting Polymer for Selective Separation of Branched Cyclodextrins
Molecules 2017, 22(2), 288; https://doi.org/10.3390/molecules22020288
Received: 28 December 2016 / Revised: 6 February 2017 / Accepted: 8 February 2017 / Published: 21 February 2017
Cited by 2 | PDF Full-text (5089 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
In the present study, photoirradiation molecularly imprinted polymer (MIP) with azobenzene was used as a functional monomer for the selective separation of the branched cyclodextrins. The functional monomer 4-methacryloyloxy azobenzene (MAA) and the molecular template 6-O-α-d-maltosyl-β-cyclodextrin (G2-β-CD) were implemented
[...] Read more.
In the present study, photoirradiation molecularly imprinted polymer (MIP) with azobenzene was used as a functional monomer for the selective separation of the branched cyclodextrins. The functional monomer 4-methacryloyloxy azobenzene (MAA) and the molecular template 6-O-α-d-maltosyl-β-cyclodextrin (G2-β-CD) were implemented for the molecular imprinting. The core-shell structure of photoirradiation MIP was visualized by the transmission electron microscopy (TEM). With Fourier transform infrared spectroscopy (FTIR) and thermogravimetric analysis (TGA), we identified that G2-β-CD was imprinted into the polymer and removed from the MIP. The binding association constant (Ka) and the maximum number of the binding site (Nmax) were 1.72 × 104 M−1 and 7.93 μmol·g−1 MIP, respectively. With alternate irradiation at 365 and 440 nm light, the prepared MIP reversibly released and rebound to the G2-β-CD, which resulted in the nearly zero amount of G2-β-CD in the solution. The HPLC results indicated that the purity of G2-β-CD could reach 90.8% after going through MIP. The main finding of our study was that the photoirradiation of MIP was an easy and effective method for the selective separation of the branched cyclodextrins. Full article
(This article belongs to the Special Issue Cyclodextrin Chemistry)
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Open AccessArticle Oxidation of 5-Chloromethylfurfural (CMF) to 2,5-Diformylfuran (DFF)
Molecules 2017, 22(2), 329; https://doi.org/10.3390/molecules22020329
Received: 15 January 2017 / Revised: 10 February 2017 / Accepted: 14 February 2017 / Published: 20 February 2017
Cited by 2 | PDF Full-text (1345 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
2,5-Diformylfuran (DFF) is an important biorenewable building block, namely for the manufacture of new polymers that may replace existing materials derived from limited fossil fuel resources. The current reported methods for the preparation of DFF are mainly derived from the oxidation of 5-hydroxymethylfurfural
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2,5-Diformylfuran (DFF) is an important biorenewable building block, namely for the manufacture of new polymers that may replace existing materials derived from limited fossil fuel resources. The current reported methods for the preparation of DFF are mainly derived from the oxidation of 5-hydroxymethylfurfural (HMF) and, to a lesser extent, directly from fructose. 5-Chloromethylfurfural (CMF) has been considered an alternative to HMF as an intermediate building block due to its advantages regarding stability, polarity, and availability from glucose and cellulose. The only reported method for the transformation of CMF to DFF is restricted to the use of DMSO as the solvent and oxidant. We envisioned that the transformation could be performed using more attractive conditions. To that end, we explored the oxidation of CMF to DFF by screening several oxidants such as H2O2, oxone, and pyridine N-oxide (PNO); different heating methods, namely thermal and microwave irradiation (MWI); and also flow conditions. The combination of PNO (4 equiv.) and Cu(OTf)2 (0.5 equiv.) in acetonitrile was identified as the best system, which lead to the formation of DFF in 54% yield under MWI for 5 min at 160 °C. Consequently, a range of different heterogeneous copper catalysts were tested, which allowed for catalyst reuse. Similar results were also observed under flow conditions using copper immobilized on silica under thermal heating at 160 °C for a residence time of 2.7 min. Finally, HMF and 5,5′-oxybis(5-methylene-2-furaldehyde) (OBMF) were the only byproducts identified under the reaction conditions studied. Full article
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Open AccessArticle Green Hydroselenation of Aryl Alkynes: Divinyl Selenides as a Precursor of Resveratrol
Molecules 2017, 22(2), 327; https://doi.org/10.3390/molecules22020327
Received: 19 January 2017 / Revised: 14 February 2017 / Accepted: 16 February 2017 / Published: 20 February 2017
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Abstract
A simple and efficient protocol to prepare divinyl selenides has been developed by the regio- and stereoselective addition of sodium selenide species to aryl alkynes. The nucleophilic species was generates in situ, from the reaction of elemental selenium with NaBH4,
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A simple and efficient protocol to prepare divinyl selenides has been developed by the regio- and stereoselective addition of sodium selenide species to aryl alkynes. The nucleophilic species was generates in situ, from the reaction of elemental selenium with NaBH4, utilizing PEG-400 as the solvent. Several divinyl selenides were obtained in moderate to excellent yields with selectivity for the (Z,Z)-isomer by a one-step procedure that was carried out at 60 °C in short reaction times. The methodology was extended to tellurium, giving the desired divinyl tellurides in good yields. Furthermore, the Fe-catalyzed cross-coupling reaction of bis(3,5-dimethoxystyryl) selenide 3f with (4-methoxyphenyl)magnesium bromide 5 afforded resveratrol trimethyl ether 6 in 57% yield. Full article
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Open AccessArticle Synthesis and Structural Evaluation of Organo-Ruthenium Complexes with β-Diketonates
Molecules 2017, 22(2), 326; https://doi.org/10.3390/molecules22020326
Received: 1 February 2017 / Revised: 15 February 2017 / Accepted: 17 February 2017 / Published: 20 February 2017
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Abstract
Four novel ruthenium organometallic complexes: [(η6-p-cymene)Ru(4,4,4-trifluoro-1-(4-bromophenyl)-1,3-butanedione)Cl] (1), [(η6-p-cymene)Ru(4,4,4-trifluoro-1-(4-bromophenyl)-1,3-butanedione)pta]PF6 (2), [(η6-p-cymene)Ru(4,4,4-trifluoro-1-(4-iodophenyl)-1,3-butanedione)Cl] (3) and [(η6-p-cymene)Ru(4,4,4-trifluoro-1-(4-iodophenyl)-1,3-butanedione)pta]PF6 (4) were synthesized and
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Four novel ruthenium organometallic complexes: [(η6-p-cymene)Ru(4,4,4-trifluoro-1-(4-bromophenyl)-1,3-butanedione)Cl] (1), [(η6-p-cymene)Ru(4,4,4-trifluoro-1-(4-bromophenyl)-1,3-butanedione)pta]PF6 (2), [(η6-p-cymene)Ru(4,4,4-trifluoro-1-(4-iodophenyl)-1,3-butanedione)Cl] (3) and [(η6-p-cymene)Ru(4,4,4-trifluoro-1-(4-iodophenyl)-1,3-butanedione)pta]PF6 (4) were synthesized and characterized by elemental analysis, infrared (IR), UV-Vis, NMR and mass spectroscopy and single-crystal X-ray diffraction. The crystal structures and spectroscopic data were compared to the previously published complexes [(η6-p-cymene)Ru(4,4,4-trifluoro-1-(4-chloro-phenyl)-1,3-butanedione)Cl] (5) and [(η6-p-cymene)Ru(4,4,4-trifluoro-1-(4-chlorophenyl)-1,3-butanedione)pta]PF6 (6). The pairs of complexes 1 and 3 as well as 2 and 4 are isostructural, with the former crystallizing in triclinic P-1 and the latter in monoclinic P21/c. The ruthenium(II) ion is found in a pseudo-octahedral “piano-stool” geometry in all compounds. Bond lengths and angles are consistent with other complexes of this type. Complexes 2 and 4 exhibit some moderate dynamic disorder. The lack of hydrogen bonding and major π-π interactions means that most of intramolecular interactions are fairly weak and involve halogen atoms present. This was further confirmed by 1H-NMR spectra, where a significant difference is observed only on the ligand near the halogen atom, following an expected trend. The combined data show that the difference in any activity depends substantially on the type of the ligand′s substituted halogen atom. Full article
(This article belongs to the Section Organometallic Chemistry)
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Open AccessArticle Analysis of the Total Biflavonoids Extract from Selaginella doederleinii by HPLC-QTOF-MS and Its In Vitro and In Vivo Anticancer Effects
Molecules 2017, 22(2), 325; https://doi.org/10.3390/molecules22020325
Received: 16 January 2017 / Revised: 9 February 2017 / Accepted: 14 February 2017 / Published: 20 February 2017
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Abstract
Selaginella doederleinii Hieron has been traditionally used as a folk antitumor herbal medicine in China. In this paper, the phytochemical components of the total biflavonoids extract from S. doederleinii were studied by using high-performance liquid chromatography coupled with electrospray ionization quadrupole time-of-flight mass
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Selaginella doederleinii Hieron has been traditionally used as a folk antitumor herbal medicine in China. In this paper, the phytochemical components of the total biflavonoids extract from S. doederleinii were studied by using high-performance liquid chromatography coupled with electrospray ionization quadrupole time-of-flight mass spectrometry (HPLC-ESI-QTOF MS/MS) in negative ion mode, and their in vitro and in vivo anticancer effects were evaluated. Four types of biflavonoids from S. doederleinii, including IC3′–IIC8′′, IC3′–IIC6′′, IC3′–IIC3′′′, and C–O linked biflavonoids were examined originally using QTOF MS/MS. The fragmentation behavior of IC3′–IIC3′′′ linked biflavonoids was reported for the first time. A total of twenty biflavonoids were identified or tentatively characterized and eight biflavonoids were found from S. doederleinii for the first time. Furthermore, the 3-(4,5-Dimethyl-2-thizolyl)-2,5-diphenyltertazolium bromide (MTT) assay and xenograft model of mouse lewis lung cancer(LLC) in male C57BL/6 mice revealed favorable anticancer properties of the total biflavonoids extracts from S. doederleinii. The results of this work could provide useful knowledge for the identification of biflavonoids in herbal samples and further insights into the chemopreventive function of this plant. Full article
(This article belongs to the Section Natural Products Chemistry)
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Open AccessArticle Transcriptomic Analysis of Leaf in Tree Peony Reveals Differentially Expressed Pigments Genes
Molecules 2017, 22(2), 324; https://doi.org/10.3390/molecules22020324
Received: 15 January 2017 / Accepted: 13 February 2017 / Published: 20 February 2017
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Abstract
Tree peony (Paeonia suffruticosa Andrews) is an important traditional flower in China. Besides its beautiful flower, the leaf of tree peony has also good ornamental value owing to its leaf color change in spring. So far, the molecular mechanism of leaf color change
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Tree peony (Paeonia suffruticosa Andrews) is an important traditional flower in China. Besides its beautiful flower, the leaf of tree peony has also good ornamental value owing to its leaf color change in spring. So far, the molecular mechanism of leaf color change in tree peony is unclear. In this study, the pigment level and transcriptome of three different color stages of tree peony leaf were analyzed. The purplish red leaf was rich in anthocyanin, while yellowish green leaf was rich in chlorophyll and carotenoid. Transcriptome analysis revealed that 4302 differentially expressed genes (DEGs) were upregulated, and 4225 were downregulated in the purplish red leaf vs. yellowish green leaf. Among these DEGs, eight genes were predicted to participate in anthocyanin biosynthesis, eight genes were predicted involved in porphyrin and chlorophyll metabolism, and 10 genes were predicted to participate in carotenoid metabolism. In addition, 27 MYBs, 20 bHLHs, 36 WD40 genes were also identified from DEGs. Anthocyanidin synthase (ANS) is the key gene that controls the anthocyanin level in tree peony leaf. Protochlorophyllide oxido-reductase (POR) is the key gene which regulated the chlorophyll content in tree peony leaf. Full article
(This article belongs to the Section Molecular Diversity)
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Open AccessReview Design of Drug Delivery Systems Containing Artemisinin and Its Derivatives
Molecules 2017, 22(2), 323; https://doi.org/10.3390/molecules22020323
Received: 26 December 2016 / Revised: 10 February 2017 / Accepted: 15 February 2017 / Published: 20 February 2017
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Abstract
Artemisinin and its derivatives have been reported to be experimentally effective for the treatment of highly aggressive cancers without developing drug resistance, they are useful for the treatment of malaria, other protozoal infections and they exhibit antiviral activity. However, they are limited pharmacologically
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Artemisinin and its derivatives have been reported to be experimentally effective for the treatment of highly aggressive cancers without developing drug resistance, they are useful for the treatment of malaria, other protozoal infections and they exhibit antiviral activity. However, they are limited pharmacologically by their poor bioavailability, short half-life in vivo, poor water solubility and long term usage results in toxicity. They are also expensive for the treatment of malaria when compared to other antimalarials. In order to enhance their therapeutic efficacy, they are incorporated onto different drug delivery systems, thus yielding improved biological outcomes. This review article is focused on the currently synthesized derivatives of artemisinin and different delivery systems used for the incorporation of artemisinin and its derivatives. Full article
(This article belongs to the Special Issue Artemisinin: Against Malaria, Cancer and Viruses)
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Open AccessArticle Simultaneous Quantification of Nine New Furanocoumarins in Angelicae Dahuricae Radix Using Ultra-Fast Liquid Chromatography with Tandem Mass Spectrometry
Molecules 2017, 22(2), 322; https://doi.org/10.3390/molecules22020322
Received: 9 December 2016 / Revised: 26 January 2017 / Accepted: 13 February 2017 / Published: 20 February 2017
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Abstract
A series of new furanocoumarins with long-chain hydrophobic groups, namely andafocoumarins A–H and J, have been isolated from the dried roots of Angelica dahurica cv. Hangbaizhi (Angelicae Dahuricae radix) in our previous study, among which andafocoumarins A and B were demonstrated to have
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A series of new furanocoumarins with long-chain hydrophobic groups, namely andafocoumarins A–H and J, have been isolated from the dried roots of Angelica dahurica cv. Hangbaizhi (Angelicae Dahuricae radix) in our previous study, among which andafocoumarins A and B were demonstrated to have better anti-inflammatory activity than the positive controls. In this work, a sensitive, accurate, and efficient ultra-fast liquid chromatography coupled with triple quadrupole mass spectrometer (UFLC-MS/MS) method was developed and validated for simultaneous quantification of above-mentioned nine compounds in four cultivars of Angelicae Dahuricae Radix. Chromatographic separation was performed on a Kinetex 2.6u C18 100 Å column (100 × 2.1 mm, 2.6 µm). The mobile phases were comprised of acetonitrile and water with a flow rate of 0.5 mL/min. Using the established method, all components could be easily separated within 12 min. With the multiple reaction monitor mode, all components were detected in positive electrospray ionization. The method was validated with injection precision, linearity, lower limit of detection, lower limit of quantification, precision, recovery, and stability, respectively. The final results demonstrated that the method was accurate and efficient, which could be used to simultaneously quantify the nine andafocoumarins in Angelicae Dahuricae Radix. The results also indicated that in different batches of Angelicae Dahuricae Radix, some of the andafocoumarins were significantly different in terms of content. Full article
(This article belongs to the collection Bioactive Compounds)
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Open AccessArticle Three Chalconoids and a Pterocarpene from the Roots of Tephrosia aequilata
Molecules 2017, 22(2), 318; https://doi.org/10.3390/molecules22020318
Received: 7 January 2017 / Revised: 1 February 2017 / Accepted: 14 February 2017 / Published: 20 February 2017
Cited by 2 | PDF Full-text (423 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
In our search for new antiplasmodial agents, the CH2Cl2/CH3OH (1:1) extract of the roots of Tephrosia aequilata was investigated, and observed to cause 100% mortality of the chloroquine-sensitive (3D7) strain of Plasmodium falciparum at a 10 mg/mL
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In our search for new antiplasmodial agents, the CH2Cl2/CH3OH (1:1) extract of the roots of Tephrosia aequilata was investigated, and observed to cause 100% mortality of the chloroquine-sensitive (3D7) strain of Plasmodium falciparum at a 10 mg/mL concentration. From this extract three new chalconoids, E-2′,6′-dimethoxy-3′,4′-(2′′,2′′-dimethyl)pyranoretrochalcone (1, aequichalcone A), Z-2′,6′-dimethoxy-3′,4′-(2′′,2′′-dimethyl)pyranoretrochalcone (2, aequichalcone B), 4′′-ethoxy-3′′-hydroxypraecansone B (3, aequichalcone C) and a new pterocarpene, 3,4:8,9-dimethylenedioxy-6a,11a-pterocarpene (4), along with seven known compounds were isolated. The purified compounds were characterized by NMR spectroscopic and mass spectrometric analyses. Compound 1 slowly converts into 2 in solution, and thus the latter may have been enriched, or formed, during the extraction and separation process. The isomeric compounds 1 and 2 were both observed in the crude extract. Some of the isolated constituents showed good to moderate antiplasmodial activity against the chloroquine-sensitive (3D7) strain of Plasmodium falciparum. Full article
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Open AccessArticle Neoflavonoids as Inhibitors of HIV-1 Replication by Targeting the Tat and NF-κB Pathways
Molecules 2017, 22(2), 321; https://doi.org/10.3390/molecules22020321
Received: 12 January 2017 / Revised: 19 January 2017 / Accepted: 16 February 2017 / Published: 19 February 2017
Cited by 2 | PDF Full-text (794 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Twenty-eight neoflavonoids have been prepared and evaluated in vitro against HIV-1. Antiviral activity was assessed on MT-2 cells infected with viral clones carrying the luciferase reporter gene. Inhibition of HIV transcription and Tat function were tested on cells stably transfected with the HIV-LTR
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Twenty-eight neoflavonoids have been prepared and evaluated in vitro against HIV-1. Antiviral activity was assessed on MT-2 cells infected with viral clones carrying the luciferase reporter gene. Inhibition of HIV transcription and Tat function were tested on cells stably transfected with the HIV-LTR and Tat protein. Seven 4-phenylchromen-2-one derivatives showed HIV transcriptional inhibitory activity but only the phenylchrome-2-one 10 inhibited NF-κB and displayed anti-Tat activity simultaneously. Compounds 10, 14, and 25, inhibited HIV replication in both targets at concentrations <25 μM. The assays of these synthetic 4-phenylchromen-2-ones may aid in the investigation of some aspects of the anti-HIV activity of such compounds and could serve as a scaffold for designing better anti-HIV compounds, which may lead to a potential anti-HIV therapeutic drug. Full article
(This article belongs to the Section Bioorganic Chemistry)
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Open AccessArticle Hydrophilic Dogwood Extracts as Materials for Reducing the Skin Irritation Potential of Body Wash Cosmetics
Molecules 2017, 22(2), 320; https://doi.org/10.3390/molecules22020320
Received: 3 December 2016 / Revised: 5 February 2017 / Accepted: 15 February 2017 / Published: 19 February 2017
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Abstract
A significant problem related to the use of surfactants in body wash cosmetics is their propensity to trigger skin irritations. Only scarce literature exists on the effect of plant extracts on the skin irritation potential. The present study is an attempt to determine
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A significant problem related to the use of surfactants in body wash cosmetics is their propensity to trigger skin irritations. Only scarce literature exists on the effect of plant extracts on the skin irritation potential. The present study is an attempt to determine the effect of hydrophilic dogwood extracts on the irritant potential of body wash gels. Extractants used in the study were water and mixtures of water with glycerine, water with trimethylglycine (betaine), and water with plant-derived glycol (propanediol). The basic biochemical properties, i.e., the ability to neutralize free radicals, and the content of polyphenols, anthocyanins and flavonoids, were determined. An attempt was undertaken to analyze the impact of the extract added to natural body wash gel formulations on product properties. The skin irritation potential was assessed by determining the zein number and the increase in the pH level of the bovine serum albumin (BSA) solution. The viscosity and foaming ability of the resulting products were evaluated. The studies revealed that an addition of dogwood extract contributes to an improvement in the properties of body wash gels and significantly increases the safety of product use through reducing the skin irritation effect. Full article
(This article belongs to the Special Issue Green Production of Bioactive Natural Products)
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Open AccessArticle An Efficient Synthesis of Novel Bioactive Thiazolyl-Phthalazinediones under Ultrasound Irradiation
Molecules 2017, 22(2), 319; https://doi.org/10.3390/molecules22020319
Received: 15 November 2016 / Revised: 16 January 2017 / Accepted: 14 February 2017 / Published: 18 February 2017
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Abstract
Novel 2-thiazolylphthalazine derivatives were efficiently synthesized under ultrasound irradiation, resulting in high yields and short reaction times after optimization of the reaction conditions. All prepared compounds were fully characterized using spectroscopic methods. They were screened for their antimicrobial activity against Gram-positive and Gram-negative
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Novel 2-thiazolylphthalazine derivatives were efficiently synthesized under ultrasound irradiation, resulting in high yields and short reaction times after optimization of the reaction conditions. All prepared compounds were fully characterized using spectroscopic methods. They were screened for their antimicrobial activity against Gram-positive and Gram-negative bacteria as well as for antifungal activity. The antimicrobial activity profile of the tested compounds showed some promising results. The potent activity of compounds 4d, 7b (117% zone inhibition) and 7c (105% zone inhibition) against Salmonella sp., exceeding that of the reference drug Gentamycin is particularly noteworthy. In general, the newly synthesized thiazolylphthalazine derivatives showed higher antimicrobial activity against the tested Gram-negative bacteria than against Gram-positive bacteria and fungi. Full article
(This article belongs to the Special Issue Sulfur-Nitrogen Heteroaromatics)
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Open AccessEditorial Special Issue: Ribosome-Inactivating Proteins—Commemorative Issue in Honor of Professor Fiorenzo Stirpe
Molecules 2017, 22(2), 316; https://doi.org/10.3390/molecules22020316
Received: 15 February 2017 / Revised: 16 February 2017 / Accepted: 16 February 2017 / Published: 18 February 2017
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Abstract
The family of ribosome-inactivating proteins (RIPs) groups all enzymes (EC.3.2.2.22) with a so-called RIP domain which comprises N-glycosidase activity and enables these proteins to catalytically inactivate ribosomes.[...] Full article
Open AccessCommunication An Easy Approach to Control β-Phase Formation in PFO Films for Optimized Emission Properties
Molecules 2017, 22(2), 315; https://doi.org/10.3390/molecules22020315
Received: 11 January 2017 / Revised: 7 February 2017 / Accepted: 14 February 2017 / Published: 18 February 2017
Cited by 5 | PDF Full-text (1486 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
We demonstrate a novel approach to control β-phase content generated in poly(9,9-dioctylfluorene) (PFO) films. A very small amount of paraffin oil was used as the additive to the PFO solution in toluene. The β-phase fraction in the spin-coated PFO films can be modified
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We demonstrate a novel approach to control β-phase content generated in poly(9,9-dioctylfluorene) (PFO) films. A very small amount of paraffin oil was used as the additive to the PFO solution in toluene. The β-phase fraction in the spin-coated PFO films can be modified from 0% to 20% simply by changing the volume percentage of paraffin oil in the mixed solution. Organic light emitting diodes (OLEDs) and amplified spontaneous emission (ASE) study confirmed low β-phase fraction promise better OLEDs device, while high β-phase fraction benefits ASE performance. Full article
(This article belongs to the Special Issue Advances in Organic Nanophotonics)
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Open AccessArticle Substitution at the C-3 Position of Catechins Has an Influence on the Binding Affinities against Serum Albumin
Molecules 2017, 22(2), 314; https://doi.org/10.3390/molecules22020314
Received: 29 December 2016 / Revised: 15 February 2017 / Accepted: 16 February 2017 / Published: 18 February 2017
Cited by 4 | PDF Full-text (1326 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
It is known that catechins interact with the tryptophan (Trp) residue at the drug-binding site of serum albumin. In this study, we used catechin derivatives to investigate which position of the catechin structure strongly influences the binding affinity against bovine serum albumin (BSA)
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It is known that catechins interact with the tryptophan (Trp) residue at the drug-binding site of serum albumin. In this study, we used catechin derivatives to investigate which position of the catechin structure strongly influences the binding affinity against bovine serum albumin (BSA) and human serum albumin (HSA). A docking simulation showed that (−)-epigallocatechin gallate (EGCg) interacted with both Trp residues of BSA (one at drug-binding site I and the other on the molecular surface), mainly by π–π stacking. Fluorescence analysis showed that EGCg and substituted EGCg caused a red shift of the peak wavelength of Trp similarly to warfarin (a drug-binding site I-specific compound), while 3-O-acyl-catechins caused a blue shift. To evaluate the binding affinities, the quenching constants were determined by the Stern–Volmer equation. A gallate ester at the C-3 position increased the quenching constants of the catechins. Against BSA, acyl substitution increased the quenching constant proportionally to the carbon chain lengths of the acyl group, whereas methyl substitution decreased the quenching constant. Against HSA, neither acyl nor methyl substitution affected the quenching constant. In conclusion, substitution at the C-3 position of catechins has an important influence on the binding affinity against serum albumin. Full article
(This article belongs to the Section Natural Products Chemistry)
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