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Molecules, Volume 23, Issue 11 (November 2018) – 322 articles

Cover Story (view full-size image): Half-sandwich rhodium complexes supported by the pentamethylcyclopentadienyl (Cp*) ligand are attracting renewed interest in studies of coordination chemistry and catalysis. These compounds have recently been shown to undergo unique and useful [Cp*]-centered protonation reactions following two-electron reduction from the RhIII state to the formally RhI state. However, the intermediate one-electron reduced compounds involved in these processes are typically unstable and cannot be directly observed during electrochemistry due to occurrence of ECE′-type electrode processes. In their Feature Article, Moore et al. show that use of the 4,4′-dinitro-2,2′-bipyridyl ligand (dnbpy) on the [Cp*Rh] framework enables generation and direct observation of such an unusual, singly-reduced species. View this paper.
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11 pages, 4276 KiB  
Article
8-Oxo-9-Dihydromakomakine Isolated from Aristotelia chilensis Induces Vasodilation in Rat Aorta: Role of the Extracellular Calcium Influx
by Fredi Cifuentes, Javier Palacios, Adrián Paredes, Chukwuemeka R. Nwokocha and Cristian Paz
Molecules 2018, 23(11), 3050; https://doi.org/10.3390/molecules23113050 - 21 Nov 2018
Cited by 10 | Viewed by 3586
Abstract
8-Oxo-9-dihydromakomakine is a tetracyclic indole alkaloid extracted from leaves of the Chilean tree Aristotelia chilensis. The present study investigated the effects of this alkaloid on vascular response in tissues isolated from aortic segments obtained from normotensive rats. Our results showed that 8-oxo-9-dihydromakomakine [...] Read more.
8-Oxo-9-dihydromakomakine is a tetracyclic indole alkaloid extracted from leaves of the Chilean tree Aristotelia chilensis. The present study investigated the effects of this alkaloid on vascular response in tissues isolated from aortic segments obtained from normotensive rats. Our results showed that 8-oxo-9-dihydromakomakine induced a dose-dependent relaxation of aortic rings pre-contracted with phenylephrine (PE; 10−6 M). The vasorelaxation induced by 8-oxo-9-dihydromakomakine in rat aortic rings is independent of endothelium. The pre-incubation of aortic rings with 8-oxo-9-dehydromakomakine (10−4 M) significantly reduced the contractile response to KCl (p < 0.001) more than PE (p < 0.05). The highest dose of 8-oxo-9-dehydromakomakine (10−4 M) drastically reduced the contraction to KCl (6·10−2 M), but after that, PE (10−6 M) caused contraction (p < 0.05) in the same aortic rings. The addition of 8-oxo-9-dihydromakomakine (10−5 M) decreased the contractile response to tetraethylammonium (a voltage-dependent potassium channels blocker; TEA; 5 × 10−3 M; p < 0.01) and BaCl2 (a non-selective inward rectifier potassium channel blocker; 5 × 10−3 M; p < 0.001) in rat aorta. 8-oxo-9-dihydromakomakine (10−5 M) decreased the contractile response to PE in rat aorta in the presence or absence of ouabain (an inhibitor of Na,K-ATPase; 10−3 M; p < 0.05). These results could indicate that 8-oxo-9-dihydromakomakine partially reduces plasma membrane depolarization-induced contraction. In aortic rings depolarized by PE, 8-oxo-9-dihydromakomakine inhibited the contraction induced by the influx of extracellular Ca2+ in a Ca2+ free solution (p < 0.01). 8-oxo-9-dihydromakomakine reduced the contractile response to agonists of voltage-dependent calcium channels type L (Bay K6844; 10−8 M; p < 0.01), likely decreasing the influx of extracellular Ca2+ through the voltage-dependent calcium channels. This study provides the first qualitative analysis indicating that traditional folk medicine Aristotelia chilensis may be protective in the treatment of cardiovascular pathologies. Full article
(This article belongs to the Special Issue Advances in Plant Alkaloid Research)
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12 pages, 2786 KiB  
Article
Characterization of Arginine Catabolism by Lactic Acid Bacteria Isolated from Kimchi
by Hyelyeon Hwang and Jong-Hee Lee
Molecules 2018, 23(11), 3049; https://doi.org/10.3390/molecules23113049 - 21 Nov 2018
Cited by 26 | Viewed by 5403
Abstract
Kimchi fermentation depends on diverse lactic acid bacteria, which convert raw materials into numerous metabolites that contribute to the taste of food. Amino acids and saccharides are important primary metabolites. Arginine is nearly exhausted during kimchi fermentation, whereas the concentrations of other amino [...] Read more.
Kimchi fermentation depends on diverse lactic acid bacteria, which convert raw materials into numerous metabolites that contribute to the taste of food. Amino acids and saccharides are important primary metabolites. Arginine is nearly exhausted during kimchi fermentation, whereas the concentrations of other amino acids are reported not to increase or decrease dramatically. These phenomena could imply that arginine is an important nutritional component among the amino acids during kimchi fermentation. In this study, we investigated the arginine-catabolism pathway of seven lactic acid bacteria isolated from kimchi and evaluated the products of arginine catabolism (citrulline and ornithine) associated with the bacteria. The arginine content dramatically decreased in cultures of Lactobacillus brevis and Weissella confusa from 300 μg/mL of arginine to 0.14 ± 0.19 and 1.3 ± 0.01 μg/mL, respectively, after 6 h of cultivation. Citrulline and ornithine production by L. brevis and W. confusa showed a pattern that was consistent with arginine catabolism. Interestingly, Pediococcus pentosaceus, Lactobacillus plantarum, Leuconostoc mesenteroides, and Leuconostoc lactis did not show increased citrulline levels after arginine was added. The ornithine contents were higher in all bacteria except for L. lactis after adding arginine to the culture. These results were consistent with the absence of the arginine deiminase gene among the lactic acid bacteria. Arginine consumption and ornithine production were monitored and compared with lactic acid bacteria by metagenomics analysis, which showed that the increment of ornithine production correlated positively with lactic acid bacteria growth. Full article
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6 pages, 971 KiB  
Communication
An Example of a Novel Efficient Plant Extraction Technique: Electromagnetic Induction Heating
by Francesco Epifano, Francesca Preziuso, Vito Alessandro Taddeo, Serena Fiorito and Salvatore Genovese
Molecules 2018, 23(11), 3048; https://doi.org/10.3390/molecules23113048 - 21 Nov 2018
Cited by 2 | Viewed by 3026
Abstract
A simple and easy to handle extraction procedure based on the use of electromagnetic induction heating is described. To assess the potential, scopes, and limitations of this novel process, extraction and subsequent HPLC quantification of emodin from an hydroalcoholic extract of rhizome of [...] Read more.
A simple and easy to handle extraction procedure based on the use of electromagnetic induction heating is described. To assess the potential, scopes, and limitations of this novel process, extraction and subsequent HPLC quantification of emodin from an hydroalcoholic extract of rhizome of Rheum palmatum (Chinese rhubarb) was selected as the reference experiment. Maceration at room temperature and by heating, ultrasound-assisted, and microwave-assisted extractions were also carried out for comparison. Results obtained with electromagnetic induction heating showed that this methodology performed largely better both in terms of time process and extraction yields. Full article
(This article belongs to the Special Issue Natural Product Isolation, Identification and Biological Activity)
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15 pages, 1754 KiB  
Article
Improvement of Quality Properties and Shelf Life Stability of New Formulated Muffins Based on Black Rice
by Constantin Croitoru, Claudia Mureșan, Mihaela Turturică, Nicoleta Stănciuc, Doina Georgeta Andronoiu, Loredana Dumitrașcu, Vasilica Barbu, Elena Enachi (Ioniță), Georgiana Horincar (Parfene) and Gabriela Râpeanu
Molecules 2018, 23(11), 3047; https://doi.org/10.3390/molecules23113047 - 21 Nov 2018
Cited by 15 | Viewed by 4715
Abstract
Effects of partial (50%) and total replacement of wheat flour with black rice flour on the phytochemical, physico-chemical, sensorial, and textural properties of muffins were studied. Partial or total replacement of wheat flour with black rice flour in muffins improved their nutritional and [...] Read more.
Effects of partial (50%) and total replacement of wheat flour with black rice flour on the phytochemical, physico-chemical, sensorial, and textural properties of muffins were studied. Partial or total replacement of wheat flour with black rice flour in muffins improved their nutritional and antioxidative properties with a positive effect on microbiological and color stability during the storage period in accelerated conditions. The low gluten muffins had an anthocyanin content of 27.54 ± 2.22 mg cyanidin-3-glucoside (C3G)/100 g dry weight (DW), whereas the gluten free muffins had 46.11 ± 3.91 mg C3G/100 g DW, with significant antioxidant values. Retention of 60% and 64% for anthocyanins and 72% and 80% for antioxidant activity after baking was found. The fracturability and hardness scores increased with the addition of black rice flour, whereas firmness and chewiness increased for gluten free muffins. The confocal analysis revealed a tendency of glucidic components to aggregate, with gathers of small bunches of black rice starch granules comprising anthocyanin. The results allowed designing two new value added bakery products, low and free gluten muffins, with significant high amounts of bioactive compounds, suggesting the functional potential of black rice flour. Full article
(This article belongs to the Special Issue Natural Additives in Food)
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15 pages, 5577 KiB  
Article
TiO2-Based Hybrid Nanocomposites Modified by Phosphonate Molecules as Selective PAH Adsorbents
by Nadine Bou Orm, Quoc An Trieu and Stephane Daniele
Molecules 2018, 23(11), 3046; https://doi.org/10.3390/molecules23113046 - 21 Nov 2018
Cited by 10 | Viewed by 3790
Abstract
A robust sol-gel process was developed for the synthesis of surface-functionalized titania nanocrystallites bearing unsaturated groups starting from molecular heteroleptic single-source precursors. Molecules and nanomaterials were thoroughly characterized by multinuclear liquid and solid-state nuclear magnetic resonance (NMR), infra-red (FT-IR, DRIFT) spectroscopies. Nitrogen adsorption-desorption [...] Read more.
A robust sol-gel process was developed for the synthesis of surface-functionalized titania nanocrystallites bearing unsaturated groups starting from molecular heteroleptic single-source precursors. Molecules and nanomaterials were thoroughly characterized by multinuclear liquid and solid-state nuclear magnetic resonance (NMR), infra-red (FT-IR, DRIFT) spectroscopies. Nitrogen adsorption-desorption (BET), thermogravimetric (TG) and elemental analyses demonstrated the reliability and the fine tuning of the surface functionalization in terms of ratio TiO2:ligand. The as-prepared materials were used as nano-adsorbents to remove mixture of 16 polycyclic aromatic hydrocarbon (PAHs) from aqueous solutions. Adsorption kinetic experiments were carried out for 24 h in solutions of one PAH [benzo(a)pyrene, 220 ppb] and of a mixture of sixteen ones [220 ppb for each PAH]. Most kinetic data best fitted the pseudo-second order model. However, in PAHs mixture, a competition process took place during the first hours leading to a remarkable high selectivity between light and heavy PAHs. This selectivity could be fine-tuned depending on the nature of the unsaturated group of the phosphonate framework and on the nanomaterial textures. Full article
(This article belongs to the Special Issue Sol-Gel Chemistry. From Molecule to Functional Materials)
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9 pages, 2194 KiB  
Article
An Efficient Synthesis of Acenaphtho[1,2-b]indole Derivatives via Domino Reaction
by Guo-Ning Zhang, Xia Yuan, Weiping Niu, Mei Zhu, Juxian Wang and Yucheng Wang
Molecules 2018, 23(11), 3045; https://doi.org/10.3390/molecules23113045 - 21 Nov 2018
Cited by 4 | Viewed by 2838
Abstract
A concise and efficient synthesis of acenaphtho[1,2-b]indole derivatives via the domino reactions of enaminones with acenaphthoquinone catalyzed by l-proline has been developed. This protocol has the advantages of good yields, operational convenience and high regioselectivity. Full article
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19 pages, 4080 KiB  
Review
A Review on Electroporation-Based Intracellular Delivery
by Junfeng Shi, Yifan Ma, Jing Zhu, Yuanxin Chen, Yating Sun, Yicheng Yao, Zhaogang Yang and Jing Xie
Molecules 2018, 23(11), 3044; https://doi.org/10.3390/molecules23113044 - 21 Nov 2018
Cited by 167 | Viewed by 16224
Abstract
Intracellular delivery is a critical step in biological discoveries and has been widely utilized in biomedical research. A variety of molecular tools have been developed for cell-based gene therapies, including FDA approved CAR-T immunotherapy, iPSC, cell reprogramming and gene editing. Despite the inspiring [...] Read more.
Intracellular delivery is a critical step in biological discoveries and has been widely utilized in biomedical research. A variety of molecular tools have been developed for cell-based gene therapies, including FDA approved CAR-T immunotherapy, iPSC, cell reprogramming and gene editing. Despite the inspiring results of these applications, intracellular delivery of foreign molecules including nucleic acids and proteins remains challenging. Efficient yet non-invasive delivery of biomolecules in a high-throughput manner has thus long fascinates the scientific community. As one of the most popular non-viral technologies for cell transfection, electroporation has gone through enormous development with the assist of nanotechnology and microfabrication. Emergence of miniatured electroporation system brought up many merits over the weakness of traditional electroporation system, including precise dose control and high cell viability. These new generation of electroporation systems are of considerable importance to expand the biological applications of intracellular delivery, bypassing the potential safety issue of viral vectors. In this review, we will go over the recent progresses in the electroporation-based intracellular delivery and several potential applications of cutting-edge research on the miniatured electroporation, including gene therapy, cellular reprogramming and intracellular probe. Full article
(This article belongs to the Special Issue Application of Novel Method in Pharmaceutical Study)
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9 pages, 613 KiB  
Article
Synthesis and Biological Evaluation of Phaeosphaeride A Derivatives as Antitumor Agents
by Victoria Abzianidze, Petr Beltyukov, Sofya Zakharenkova, Natalia Moiseeva, Jennifer Mejia, Alvin Holder, Yuri Trishin, Alexander Berestetskiy and Victor Kuznetsov
Molecules 2018, 23(11), 3043; https://doi.org/10.3390/molecules23113043 - 21 Nov 2018
Cited by 8 | Viewed by 3141
Abstract
New derivatives of phaeosphaeride A (PPA) were synthesized and characterized. Anti-tumor activity studies were carried out on the HCT-116, PC3, MCF-7, A549, К562, NCI-Н929, Jurkat, THP-1, RPMI8228 tumor cell lines, and on the HEF cell line. All of the compounds synthesized were found [...] Read more.
New derivatives of phaeosphaeride A (PPA) were synthesized and characterized. Anti-tumor activity studies were carried out on the HCT-116, PC3, MCF-7, A549, К562, NCI-Н929, Jurkat, THP-1, RPMI8228 tumor cell lines, and on the HEF cell line. All of the compounds synthesized were found to have better efficacy than PPA towards the tumor cell lines mentioned. Compound 6 was potent against six cancer cell lines, HCT-116, PC-3, K562, NCI-H929, Jurkat, and RPMI8226, showing a 47, 13.5, 16, 4, 1.5, and 7-fold increase in anticancer activity comparative to those of etoposide, respectively. Compound 1 possessed selectivity toward the NCI-H929 cell line (IC50 = 1.35 ± 0.69 μM), while product 7 was selective against three cancer cell lines, HCT-116, MCF-7, and NCI-H929, each having IC50 values of 1.65 μM, 1.80 μM and 2.00 μM, respectively. Full article
(This article belongs to the Special Issue Antitumor and Anti-HIV Agents from Natural Products)
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12 pages, 1508 KiB  
Article
Solution Conformation of Heparin Tetrasaccharide. DFT Analysis of Structure and Spin–Spin Coupling Constants
by Miloš Hricovíni and Michal Hricovíni
Molecules 2018, 23(11), 3042; https://doi.org/10.3390/molecules23113042 - 21 Nov 2018
Cited by 13 | Viewed by 3289
Abstract
Density functional theory (DFT) has provided detailed information on the molecular structure and spin–spin coupling constants of heparin tetrasaccharide (GlcNS,6S-IdoA2S-GlcNS,6S-IdoA2S-OMe) representing the predominant heparin repeating-sequence. The fully optimised molecular structures of two tetrasaccharide conformations (differing from each other in the conformational form of [...] Read more.
Density functional theory (DFT) has provided detailed information on the molecular structure and spin–spin coupling constants of heparin tetrasaccharide (GlcNS,6S-IdoA2S-GlcNS,6S-IdoA2S-OMe) representing the predominant heparin repeating-sequence. The fully optimised molecular structures of two tetrasaccharide conformations (differing from each other in the conformational form of the sulphated iduronic acid residue–one 1C4 and the other 2S0) were obtained using the B3LYP/6-311+G(d,p) level of theory and applying explicit water molecules to simulate the presence of a solvent. The theoretical data provided insight into variations of the bond lengths, bond angles and torsion angles, formations of intra- and intermolecular hydrogen bonds and ionic interactions. Optimised molecular structures indicated the formation of a complex hydrogen bond network, including interresidue and intraresidue bonds. The ionic interactions strongly influence the first hydration shell and, together with hydrogen bonds, play an important role in shaping the 3D tetrasaccharide structure. DFT-derived indirect three–bond proton–proton coupling constants (3JH-C-C-H) showed that the best agreement with experiment was obtained with a weighted average of 67:33 (1C4:2S0) of the IdoA2S forms. Detailed analysis of Fermi-contact contributions to 3JH-C-C-H showed that important contributions arise from the oxygen lone pairs of neighbouring oxygen atoms. The analysis also showed that the magnitude of diamagnetic spin–orbit contributions are sufficiently large to determine the magnitude of some proton–proton coupling constants. The data highlight the need to use appropriate quantum-chemical calculations for a detailed understanding of the solution properties of heparin oligosaccharides. Full article
(This article belongs to the Special Issue Heparan Sulfate and Heparin: Challenges and Controversies)
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12 pages, 881 KiB  
Article
Selective Inhibition of Human AKR1B10 by n-Humulone, Adhumulone and Cohumulone Isolated from Humulus lupulus Extract
by Jan Moritz Seliger, Serhat Sezai Cicek, Lydia T. Witt, Hans-Jörg Martin, Edmund Maser and Jan Hintzpeter
Molecules 2018, 23(11), 3041; https://doi.org/10.3390/molecules23113041 - 21 Nov 2018
Cited by 13 | Viewed by 4764
Abstract
Hop-derived compounds have been subjected to numerous biomedical studies investigating their impact on a wide range of pathologies. Isomerised bitter acids (isoadhumulone, isocohumulone and isohumulone) from hops, used in the brewing process of beer, are known to inhibit members of the aldo-keto-reductase superfamily. [...] Read more.
Hop-derived compounds have been subjected to numerous biomedical studies investigating their impact on a wide range of pathologies. Isomerised bitter acids (isoadhumulone, isocohumulone and isohumulone) from hops, used in the brewing process of beer, are known to inhibit members of the aldo-keto-reductase superfamily. Aldo-keto-reductase 1B10 (AKR1B10) is upregulated in various types of cancer and has been reported to promote carcinogenesis. Inhibition of AKR1B10 appears to be an attractive means to specifically treat RAS-dependent malignancies. However, the closely related reductases AKR1A1 and AKR1B1, which fulfil important roles in the detoxification of endogenous and xenobiotic carbonyl compounds oftentimes crossreact with inhibitors designed to target AKR1B10. Accordingly, there is an ongoing search for selective AKR1B10 inhibitors that do not interact with endogeneous AKR1A1 and AKR1B1-driven detoxification systems. In this study, unisomerised α-acids (adhumulone, cohumulone and n-humulone) were separated and tested for their inhibitory potential on AKR1A1, AKR1B1 and AKR1B10. Also AKR1B10-mediated farnesal reduction was effectively inhibited by α-acid congeners with Ki-values ranging from 16.79 ± 1.33 µM (adhumulone) to 3.94 ± 0.33 µM (n-humulone). Overall, α-acids showed a strong inhibition with selectivity (115–137 fold) for AKR1B10. The results presented herein characterise hop-derived α-acids as a promising basis for the development of novel and selective AKR1B10-inhibitors. Full article
(This article belongs to the Special Issue Natural Product Pharmacology and Medicinal Chemistry)
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12 pages, 2197 KiB  
Article
In Vitro Evaluation of Sulforaphane and a Natural Analog as Potent Inducers of 5-Fluorouracil Anticancer Activity
by Małgorzata Milczarek, Lidia Mielczarek, Katarzyna Lubelska, Aleksandra Dąbrowska, Zdzisław Chilmonczyk, Dariusz Matosiuk and Katarzyna Wiktorska
Molecules 2018, 23(11), 3040; https://doi.org/10.3390/molecules23113040 - 21 Nov 2018
Cited by 11 | Viewed by 4009
Abstract
Isothiocyanates (R-NCS) are sulphur-containing phytochemicals. The main source are plants of the Brassicaceae family. The best known plant-derived isothiocyanate is sulforaphane that has exhibited anticancer activity in both in vivo and in vitro studies. Recent attempts to expand their use in cancer therapy [...] Read more.
Isothiocyanates (R-NCS) are sulphur-containing phytochemicals. The main source are plants of the Brassicaceae family. The best known plant-derived isothiocyanate is sulforaphane that has exhibited anticancer activity in both in vivo and in vitro studies. Recent attempts to expand their use in cancer therapy involve combining them with standard chemotherapeutics in order to increase their therapeutic efficacy. The aim of this paper is to determine the impact of sulforaphane and its natural analog alyssin on the anticancer activity of the well-known anticancer drug 5-fluorouracil. The type of drug-drug interactions was determined in prostate and colon cancer cell lines. Confocal microscopy, western blot and flow cytometry methods were employed to determine the mechanism of cytotoxic and cytostatic action of the combinations. The study revealed that additive or synergistic interactions were observed between 5-fluorouracil and both isothiocyanates, which enhanced the anticancer activity of 5-fluorouracil, particularly in colon cancer cell lines. An increased cytostatic effect was observed in case of alyssin while for sulforaphane the synergistic interaction with 5-fluorouracil involved an intensification of apoptotic cell death. Full article
(This article belongs to the Special Issue Focusing on Sulfur in Medicinal Chemistry)
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11 pages, 2707 KiB  
Article
Coptisine Suppresses Mast Cell Degranulation and Ovalbumin-Induced Allergic Rhinitis
by Shuilian Fu, Saihong Ni, Danni Wang and Tie Hong
Molecules 2018, 23(11), 3039; https://doi.org/10.3390/molecules23113039 - 21 Nov 2018
Cited by 28 | Viewed by 4955
Abstract
Coptisine is one of the main components of isoquinoline alkaloids in the coptidis rhizome. The effect of coptisine on allergic rhinitis has not been investigated. In this study, we report the effects and mechanisms of coptisine using monoclonal anti-2,4,6-dinitrophenyl-immunoglobulin (Ig) E/human serum albumin [...] Read more.
Coptisine is one of the main components of isoquinoline alkaloids in the coptidis rhizome. The effect of coptisine on allergic rhinitis has not been investigated. In this study, we report the effects and mechanisms of coptisine using monoclonal anti-2,4,6-dinitrophenyl-immunoglobulin (Ig) E/human serum albumin (DNP-IgE/HSA)-stimulated rat basophilic leukemia cells (RBL-2H3 cells) in vitro and an ovalbumin (OVA)-induced allergic rhinitis (AR) in mice. The results showed that coptisine markedly decreased the levels of β-hexosaminidase, histamine, interleukin (IL)-4, and tumor necrosis factor (TNF)-α. Coptisine also prevented morphological changes, such as restoring an elongated shape, inhibiting granule release on toluidine blue staining, and reorganizing inhibited filamentous actins (F-actin). Additionally, coptisine blocked the phosphorylation of phosphoinositide3-kinase (PI3K)/Akt (as known as protein kinase B(PKB)) in RBL-2H3 cell. Furthermore, the results showed that coptisine suppressed OVA-induced allergic rhinitis symptoms, such as nasal rubbing and OVA-specific IgE, and histamine, IL-4 and TNF-α levels in the serum of AR mice. These data suggested that coptisine should have inhibitory effects on the inflammatory responses of mast cells, and may be beneficial for the development of coptisine as a potential anti-allergic drug. Full article
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14 pages, 6537 KiB  
Article
Pseudoginsengenin DQ Exhibits Therapeutic Effects in Cisplatin-Induced Acute Kidney Injury via Sirt1/NF-κB and Caspase Signaling Pathway without Compromising Its Antitumor Activity in Mice
by Zeng Qi, Zhuo Li, Wei Li, Yunhe Liu, Cuizhu Wang, Hongqiang Lin, Jinping Liu and Pingya Li
Molecules 2018, 23(11), 3038; https://doi.org/10.3390/molecules23113038 - 21 Nov 2018
Cited by 33 | Viewed by 4217
Abstract
In this study, the protective effects of pseudoginsengenin DQ (PDQ) on cisplatin (CDDP)-induced nephrotoxicity were assessed, with a primary investigation into the mechanisms involved. Our results showed that pretreatment with PDQ remarkably restored levels of blood urea nitrogen (BUN) and creatinine (CRE), malondialdehyde [...] Read more.
In this study, the protective effects of pseudoginsengenin DQ (PDQ) on cisplatin (CDDP)-induced nephrotoxicity were assessed, with a primary investigation into the mechanisms involved. Our results showed that pretreatment with PDQ remarkably restored levels of blood urea nitrogen (BUN) and creatinine (CRE), malondialdehyde (MDA), glutathione (GSH), superoxide dismutase (SOD), catalase (CAT), tumor necrosis factor-α (TNF-α), and interleukin-1β (IL-1β). Meanwhile, PDQ decreased the CDDP-induced overexpression of heme oxygenase 1 (HO-1), cytochrome P450 E1 (CYP2E1), TNF-α, nuclear factor-kappa B (NF-κB), cyclooxygenase-2 (COX-2), and inducible nitric oxide synthase (iNOS) in renal tissues. Hoechst 33258 and TdT-mediated dUTP nick-end labeling (TUNEL) staining showed that CDDP-induced renal tubular cell apoptosis was apparently inhibited by PDQ. Western blotting showed that PDQ reversed the CDDP-induced (1) downregulation of Sirtuin-1 (Sirt-1), nuclear-related factor 2 (Nrf2), and Bcl-2, and (2) upregulation of NF-κB, Nox-4, Bax, caspase-9, and caspase-3. In addition, PDQ enhanced the antitumor activity of cisplatin in Lewis lung cancer xenograft tumor model mice. In conclusion, we found that PDQ exerted a renal protective effect against CDDP-induced acute nephrotoxicity via Sirt1/NF-κB and the caspase signaling pathway without compromising the antitumor activity of CDDP, which provides a new potential strategy for the clinical treatment of cancer and presents a new medicinal application of PDQ. Full article
(This article belongs to the Section Medicinal Chemistry)
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7 pages, 1343 KiB  
Communication
Concise Synthesis of (+)-β- and γ-Apopicropodophyllins, and Dehydrodesoxypodophyllotoxin
by Jian Xiao, Guangming Nan, Ya-Wen Wang and Yu Peng
Molecules 2018, 23(11), 3037; https://doi.org/10.3390/molecules23113037 - 21 Nov 2018
Cited by 13 | Viewed by 3104
Abstract
Herein, we present an expeditous synthesis of bioactive aryldihydronaphthalene lignans (+)-β- and γ-apopicropodophyllins, and arylnaphthalene lignan dehydrodesoxypodophyllotoxin. The key reaction is regiocontrolled oxidations of stereodivergent aryltetralin lactones, which were easily accessed from a nickel-catalyzed reductive cascade approach developed in our group. Full article
(This article belongs to the Special Issue Lignans)
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20 pages, 12675 KiB  
Article
Virtual Screening, Biological Evaluation, and 3D-QSAR Studies of New HIV-1 Entry Inhibitors That Function via the CD4 Primary Receptor
by Chaozai Zhang, Huijun Zhang, Lina S. Huang, Siyu Zhu, Yan Xu, Xing-Quan Zhang, Robert T. Schooley, Xiaohong Yang, Ziwei Huang and Jing An
Molecules 2018, 23(11), 3036; https://doi.org/10.3390/molecules23113036 - 20 Nov 2018
Cited by 7 | Viewed by 4510
Abstract
Human immunodeficiency virus type 1 (HIV-1) is responsible for the majority of HIV infections worldwide, and we still lack a cure for this infection. Blocking the interaction of HIV-1 and its primary receptor CD4 is one strategy for identifying new anti-HIV-1 entry inhibitors. [...] Read more.
Human immunodeficiency virus type 1 (HIV-1) is responsible for the majority of HIV infections worldwide, and we still lack a cure for this infection. Blocking the interaction of HIV-1 and its primary receptor CD4 is one strategy for identifying new anti-HIV-1 entry inhibitors. Here we report the discovery of a novel ligand that can inhibit HIV-1 entry and infection via CD4. Biological and computational analyses of this inhibitor and its analogs, using bioactivity evaluation, Rule of Five (RO5), comparative molecular field analysis (CoMFA)/comparative molecular similarity index analysis (CoMSIA) models, and three-dimensional quantitative structure-activity relationship (3D-QSAR), singled out compound 3 as a promising lead molecule for the further development of therapeutics targeting HIV-1 entry. Our study demonstrates an effective approach for employing structure-based, rational drug design techniques to identify novel antiviral compounds with interesting biological activities. Full article
(This article belongs to the Special Issue Computational Approaches for Drug Discovery)
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16 pages, 3054 KiB  
Article
Preparation of Enantiomeric β-(2′,5′-Dimethylphenyl)Bromolactones, Their Antiproliferative Activity and Effect on Biological Membranes
by Witold Gładkowski, Aleksandra Włoch, Aleksandra Pawlak, Angelika Sysak, Agata Białońska, Marcelina Mazur, Paweł Mituła, Gabriela Maciejewska, Bożena Obmińska-Mrukowicz and Halina Kleszczyńska
Molecules 2018, 23(11), 3035; https://doi.org/10.3390/molecules23113035 - 20 Nov 2018
Cited by 9 | Viewed by 3229
Abstract
Three novel enantiomeric pairs of bromolactones possesing a 2,5-dimethylphenyl substituent at the β-position of the lactone ring have been synthesized from corresponding enantiomeric (E)-3-(2′,5′-dimethylphenyl)hex-4-enoic acids (4) by kinetically controlled bromolactonization with N-bromosuccinimide (NBS). γ-Bromo-δ-lactones (5) were [...] Read more.
Three novel enantiomeric pairs of bromolactones possesing a 2,5-dimethylphenyl substituent at the β-position of the lactone ring have been synthesized from corresponding enantiomeric (E)-3-(2′,5′-dimethylphenyl)hex-4-enoic acids (4) by kinetically controlled bromolactonization with N-bromosuccinimide (NBS). γ-Bromo-δ-lactones (5) were isolated as the major products. Absolute configurations of stereogenic centers of γ-bromo-δ-lactones (5) were assigned based on X-ray analysis; configurations of cis δ-bromo-γ-lactones (6) and trans δ-bromo-γ-lactones (7) were determined based on mechanism of bromolactonization. Synthesized compounds exhibited significant antiproliferative activity towards the four canine cancer cell lines (D17, CLBL-1, CLB70, and GL-1) and one human cancer line (Jurkat). Classifying the compounds in terms of activity, the most active were enantiomers of trans δ-bromo-γ-lactones (7) followed by enantiomers of cis isomer (6) and enantiomeric γ-bromo-δ-lactones (5). Higher activity was observed for all stereoisomers with S configuration at C-4 in comparison with their enantiomers with 4R configuration. Synthesized compounds did not induce hemolysis of erythrocytes. The results of the interaction of bromolactones with red blood cell membranes suggest that these compounds incorporate into biological membranes, concentrating mainly in the hydrophilic part of the bilayer but have practically no influence on fluidity in the hydrophobic region. The differences in interactions with the membrane between particular enantiomers were observed only for γ-lactones: stronger interactions were found for enantiomer 4R,5R,6S of cis γ-lactone (6) and for enantiomer 4S,5R,6S of trans γ-lactone (7). Full article
(This article belongs to the Special Issue Design and Synthesis of Bioactive Compounds)
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18 pages, 533 KiB  
Article
The Utility of Supertype Clustering in Prediction for Class II MHC-Peptide Binding
by Wen-Jun Shen, Xun Zhang, Shaohong Zhang, Cheng Liu and Wenjuan Cui
Molecules 2018, 23(11), 3034; https://doi.org/10.3390/molecules23113034 - 20 Nov 2018
Cited by 8 | Viewed by 3765
Abstract
Motivation: Extensive efforts have been devoted to understanding the antigenic peptides binding to MHC class I and II molecules since they play a fundamental role in controlling immune responses and due their involvement in vaccination, transplantation, and autoimmunity. The genes coding for the [...] Read more.
Motivation: Extensive efforts have been devoted to understanding the antigenic peptides binding to MHC class I and II molecules since they play a fundamental role in controlling immune responses and due their involvement in vaccination, transplantation, and autoimmunity. The genes coding for the MHC molecules are highly polymorphic, and it is difficult to build computational models for MHC molecules with few know binders. On the other hand, previous studies demonstrated that some MHC molecules share overlapping peptide binding repertoires and attempted to group them into supertypes. Herein, we present a framework of the utility of supertype clustering to gain more information about the data to improve the prediction accuracy of class II MHC-peptide binding. Results: We developed a new method, called superMHC, for class II MHC-peptide binding prediction, including three MHC isotypes of HLA-DR, HLA-DP, and HLA-DQ, by using supertype clustering in conjunction with RLS regression. The supertypes were identified by using a novel repertoire dissimilarity index to quantify the difference in MHC binding specificities. The superMHC method achieves the state-of-the-art performance and is demonstrated to predict binding affinities to a series of MHC molecules with few binders accurately. These results have implications for understanding receptor-ligand interactions involved in MHC-peptide binding. Full article
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12 pages, 21145 KiB  
Article
Ionic Liquid-Promoted Three-Component Domino Reaction of Propargyl Alcohols, Carbon Dioxide and 2-Aminoethanols: A Thermodynamically Favorable Synthesis of 2-Oxazolidinones
by Shumei Xia, Yu Song, Xuedong Li, Hongru Li and Liang-Nian He
Molecules 2018, 23(11), 3033; https://doi.org/10.3390/molecules23113033 - 20 Nov 2018
Cited by 15 | Viewed by 4224
Abstract
To circumvent the thermodynamic limitation of the synthesis of oxazolidinones starting from 2-aminoethanols and CO2 and realize incorporation CO2 under atmospheric pressure, a protic ionic liquid-facilitated three-component reaction of propargyl alcohols, CO2 and 2-aminoethanols was developed to produce 2-oxazolidinones along [...] Read more.
To circumvent the thermodynamic limitation of the synthesis of oxazolidinones starting from 2-aminoethanols and CO2 and realize incorporation CO2 under atmospheric pressure, a protic ionic liquid-facilitated three-component reaction of propargyl alcohols, CO2 and 2-aminoethanols was developed to produce 2-oxazolidinones along with equal amount of α-hydroxyl ketones. The ionic liquid structure, reaction temperature and reaction time were in detail investigated. And 15 mol% 1,5,7-triazabicylo[4.4.0]dec-5-ene ([TBDH][TFE]) trifluoroethanol was found to be able to synergistically activate the substrate and CO2, thus catalyzing this cascade reaction under atmospheric CO2 pressure. By employing this task-specific ionic liquid as sustainable catalyst, 2-aminoethanols with different substituents were successfully transformed to 2-oxazolidinones with moderate to excellent yield after 12 h at 80 °C. Full article
(This article belongs to the Special Issue Sustainable Synthesis)
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14 pages, 1410 KiB  
Article
Antifungal Efficacy of Marine Macroalgae against Fungal Isolates from Bronchial Asthmatic Cases
by Suresh Mickymaray and Wael Alturaiki
Molecules 2018, 23(11), 3032; https://doi.org/10.3390/molecules23113032 - 20 Nov 2018
Cited by 42 | Viewed by 4733
Abstract
Fungal sensitization is very common in bronchial asthmatic cases, and the connection with airway colonization by fungi remains uncertain. Antifungal therapy failure is a significant fraction of the cost and morbidity and mortality in the majority of the asthmatic cases. Hence, the present [...] Read more.
Fungal sensitization is very common in bronchial asthmatic cases, and the connection with airway colonization by fungi remains uncertain. Antifungal therapy failure is a significant fraction of the cost and morbidity and mortality in the majority of the asthmatic cases. Hence, the present study aimed to investigate the antifungal activity of five marine macroalgae—Acanthaophora specifera, Cladophoropsis sp., Laurencia paniculata, Tydemania sp., and Ulva prolifera—which were tested on selected fungal pathogens isolated from 15 sputum of 45 bronchial asthmatic patients. The highest antifungal activity was observed in ethanol fractions of L. paniculata followed by U. prolifera, Cladophoropsis sp., A. specifera, and Tydemania sp. The minimum fungicidal concentration and minimum inhibitory concentration values of the ethanolic fractions of algal species were found to be 125–1000 µg/mL and 125–500 µg/mL, respectively. The algal extracts contained terpene alcohol, diterpene, steroids, sesquiterpene, and sesquiterpene alcohol, as determined by GC–MS/MS analyses. The present study shows that the marine macroalgae containing bioactive compounds had excellent inhibitory activity against a variety of fungal pathogens, which may be useful for combating fungal infections and recovering from chronic asthmatic states. Full article
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10 pages, 8430 KiB  
Article
A Simple and Efficient Synthesis of Highly Substituted Indeno[1,2-b]pyrrole and Acenaphtho[1,2-b]pyrrole Derivatives by Tandem Three-Component Reactions
by Xiaodong Tang, Songlei Zhu, Ying Ma, Ren Wen, Lanqi Cen, Panwei Gong and Jing Wang
Molecules 2018, 23(11), 3031; https://doi.org/10.3390/molecules23113031 - 20 Nov 2018
Cited by 9 | Viewed by 3014
Abstract
A green, convenient and tandem procedure for the efficient synthesis of highly substituted indeno[1,2-b]pyrrole and acenaphtho[1,2-b]pyrrole derivatives by domino three-component reaction of tryptamine/benzylamine, 1,3-dicarbonyl compounds and ninhydrin/ acenaphthenequinone is described. The significant features of this procedure were characterized by [...] Read more.
A green, convenient and tandem procedure for the efficient synthesis of highly substituted indeno[1,2-b]pyrrole and acenaphtho[1,2-b]pyrrole derivatives by domino three-component reaction of tryptamine/benzylamine, 1,3-dicarbonyl compounds and ninhydrin/ acenaphthenequinone is described. The significant features of this procedure were characterized by mild reaction conditions, high yields, operational simplicity and it being environmentally benign. Full article
(This article belongs to the Special Issue Multicomponent Reactions)
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13 pages, 2322 KiB  
Article
Maritoclax Enhances TRAIL-Induced Apoptosis via CHOP-Mediated Upregulation of DR5 and miR-708-Mediated Downregulation of cFLIP
by Mi-Yeon Jeon, Kyoung-jin Min, Seon Min Woo, Seung Un Seo, Yung Hyun Choi, Sang Hyun Kim, Dong Eun Kim, Tae-Jin Lee, Shin Kim, Jong-Wook Park and Taeg Kyu Kwon
Molecules 2018, 23(11), 3030; https://doi.org/10.3390/molecules23113030 - 20 Nov 2018
Cited by 16 | Viewed by 3692
Abstract
Maritoclax, an active constituent isolated from marine bacteria, has been known to induce Mcl-1 downregulation through proteasomal degradation. In this study, we investigated the sensitizing effect of maritoclax on tumor necrosis factor-related apoptosis-inducing ligand (TRAIL)-induced apoptosis in human renal carcinoma cells. We found [...] Read more.
Maritoclax, an active constituent isolated from marine bacteria, has been known to induce Mcl-1 downregulation through proteasomal degradation. In this study, we investigated the sensitizing effect of maritoclax on tumor necrosis factor-related apoptosis-inducing ligand (TRAIL)-induced apoptosis in human renal carcinoma cells. We found that combined treatment with maritoclax and TRAIL markedly induced apoptosis in renal carcinoma (Caki, ACHN and A498), lung cancer (A549) and hepatocellular carcinoma (SK-Hep1) cells. The upregulation of death receptor 5 (DR5) and downregulation of cellular FLICE-inhibitory protein (cFLIP) were involved in maritoclax plus TRAIL-induced apoptosis. Maritoclax-induced DR5 upregulation was regulated by induction of C/EBP homologous protein (CHOP) expression. Interestingly, maritoclax induced cFLIP downregulation through the increased expression of miR-708. Ectopic expression of cFLIP prevented combined maritoclax and TRAIL-induced apoptosis. Taken together, maritoclax sensitized TRAIL-induced apoptosis through CHOP-mediated DR5 upregulation and miR-708-mediated cFLIP downregulation. Full article
(This article belongs to the Section Chemical Biology)
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21 pages, 3152 KiB  
Article
Hydrogen Production from Energy Poplar Preceded by MEA Pre-Treatment and Enzymatic Hydrolysis
by Karolina Kucharska, Rafał Łukajtis, Edyta Słupek, Hubert Cieśliński, Piotr Rybarczyk and Marian Kamiński
Molecules 2018, 23(11), 3029; https://doi.org/10.3390/molecules23113029 - 20 Nov 2018
Cited by 24 | Viewed by 3392
Abstract
The need to pre-treat lignocellulosic biomass prior to dark fermentation results primarily from the composition of lignocellulose because lignin hinders the processing of hard wood towards useful products. Hence, in this work a two-step approach for the pre-treatment of energy poplar, including alkaline [...] Read more.
The need to pre-treat lignocellulosic biomass prior to dark fermentation results primarily from the composition of lignocellulose because lignin hinders the processing of hard wood towards useful products. Hence, in this work a two-step approach for the pre-treatment of energy poplar, including alkaline pre-treatment and enzymatic saccharification followed by fermentation has been studied. Monoethanolamine (MEA) was used as the alkaline catalyst and diatomite immobilized bed enzymes were used during saccharification. The response surface methodology (RSM) method was used to determine the optimal alkaline pre-treatment conditions resulting in the highest values of both total released sugars (TRS) yield and degree of lignin removal. Three variable parameters (temperature, MEA concentration, time) were selected to optimize the alkaline pre-treatment conditions. The research was carried out using the Box-Behnken design. Additionally, the possibility of the re-use of both alkaline as well as enzymatic reagents was investigated. Obtained hydrolysates were subjected to dark fermentation in batch reactors performed by Enterobacter aerogenes ATCC 13048 with a final result of 22.99 mL H2/g energy poplar (0.6 mol H2/mol TRS). Full article
(This article belongs to the Section Natural Products Chemistry)
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13 pages, 2083 KiB  
Article
Chemometric Assessment and Best-Fit Function Modelling of the Toxic Potential of Selected Food Packaging Extracts
by Błażej Kudłak, Natalia Szczepańska, Miroslava Nedyalkova, Vasil Simeonov and Jacek Namieśnik
Molecules 2018, 23(11), 3028; https://doi.org/10.3390/molecules23113028 - 20 Nov 2018
Cited by 3 | Viewed by 2479
Abstract
Food packaging materials constitute an ever more threatening environmental pollutant. This study examined options to specifically assess the ecotoxicity of packaged wastes, such as cans, subjected to various experimental treatments (in terms of extraction media, time of exposure, and temperature) that imitate several [...] Read more.
Food packaging materials constitute an ever more threatening environmental pollutant. This study examined options to specifically assess the ecotoxicity of packaged wastes, such as cans, subjected to various experimental treatments (in terms of extraction media, time of exposure, and temperature) that imitate several basic conditions of the process of food production. The extracts were studied for their ecotoxicity with bioluminescent Vibrio fischeri bacteria. The first objective of this study was to find patterns of similarity between different experimental conditions; we used multivariate statistical methods, such as hierarchical cluster analysis, to interpret the impact of experimental conditions on the ecotoxicity signals of the package extracts. Our second objective was to apply best-fit function modelling for additional data interpretation, taking into account, that ecotoxicity for various temperature conditions is time- and temperature dependent. We mathematically confirmed that chemometric data treatment allows for better understanding how different experimental conditions imitating the real use of food packaging. We also demonstrate that the level of ecotoxicity depends on different extraction media, time of exposure, and temperature regime. Full article
(This article belongs to the Section Analytical Chemistry)
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12 pages, 1767 KiB  
Article
Screening, Synthesis, and QSAR Research on Cinnamaldehyde-Amino Acid Schiff Base Compounds as Antibacterial Agents
by Hui Wang, Mingyue Jiang, Fangli Sun, Shujun Li, Chung-Yun Hse and Chunde Jin
Molecules 2018, 23(11), 3027; https://doi.org/10.3390/molecules23113027 - 20 Nov 2018
Cited by 15 | Viewed by 5226
Abstract
Development of new drugs is one of the solutions to fight against the existing antimicrobial resistance threat. Cinnamaldehyde-amino acid Schiff base compounds, are newly discovered compounds that exhibit good antibacterial activity against gram-positive and gram-negative bacteria. Quantitative structure–activity relationship (QSAR) methodology was applied [...] Read more.
Development of new drugs is one of the solutions to fight against the existing antimicrobial resistance threat. Cinnamaldehyde-amino acid Schiff base compounds, are newly discovered compounds that exhibit good antibacterial activity against gram-positive and gram-negative bacteria. Quantitative structure–activity relationship (QSAR) methodology was applied to explore the correlation between antibacterial activity and compound structures. The two best QSAR models showed R2 = 0.9354, F = 57.96, and s2 = 0.0020 against Escherichia coli, and R2 = 0.8946, F = 33.94, and s2 = 0.0043 against Staphylococcus aureus. The model analysis showed that the antibacterial activity of cinnamaldehyde compounds was significantly affected by the polarity parameter/square distance and the minimum atomic state energy for an H atom. According to the best QSAR model, the screening, synthesis, and antibacterial activity of three cinnamaldehyde-amino acid Schiff compounds were reported. The experiment value of antibacterial activity demonstrated that the new compounds possessed excellent antibacterial activity that was comparable to that of ciprofloxacin. Full article
(This article belongs to the Special Issue QSAR and QSPR: Recent Developments and Applications)
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17 pages, 35226 KiB  
Article
Lactobacillus plantarum CQPC11 Isolated from Sichuan Pickled Cabbages Antagonizes d-galactose-Induced Oxidation and Aging in Mice
by Yu Qian, Jing Zhang, Xianrong Zhou, Ruokun Yi, Jianfei Mu, Xingyao Long, Yanni Pan, Xin Zhao and Weiwei Liu
Molecules 2018, 23(11), 3026; https://doi.org/10.3390/molecules23113026 - 20 Nov 2018
Cited by 46 | Viewed by 10161
Abstract
Chinese pickled cabbage is a traditional fermented food that contains abundant microbes produced during the process of fermentation. In this work, an in vivo animal study was conducted to investigate the effects of a newly isolated lactic acid bacterium (Lactobacillus plantarum CQPC11, [...] Read more.
Chinese pickled cabbage is a traditional fermented food that contains abundant microbes produced during the process of fermentation. In this work, an in vivo animal study was conducted to investigate the effects of a newly isolated lactic acid bacterium (Lactobacillus plantarum CQPC11, LP-CQPC11) on d-galactose-induced oxidation and aging in mice. Analysis of the serum and tissue samples of these mice using molecular biology approaches showed that LP-CQPC11 suppressed the decrease in thymus, brain, heart, liver, spleen, and kidney indices caused by oxidation and aging. Furthermore, LP-CQPC11 increased the levels of SOD (superoxide dismutase), GSH-Px (glutathione peroxidase), and GSH (glutathione), whereas it reduced the levels of NO (nitric oxide) and MDA (malondialdehyde) in the serum, liver, and spleen of oxidation and aging mouse models. Pathological observation indicated that LP-CQPC11 alleviated the damage caused by oxidation and aging on the liver and spleen of mice. qPCR analysis indicated that LP-CQPC11 effectively upregulated the expression of nNOS (neuronal nitric oxide synthase), eNOS (endothelial nitric oxide synthase), Cu/Zn-SOD (cuprozinc-superoxide dismutase), Mn-SOD (manganese superoxide dismutase), CAT (catalase), HO-1 (heme oxygenase-1), Nrf2 (nuclear factor-erythroid 2 related factor 2), γ-GCS (γ-glutamylcysteine synthetase), and NQO1 (NAD(P)H dehydrogenase [quinone] 1), but downregulated the expression of iNOS (inducible nitric oxide synthase) in the mouse liver and spleen. Western blot analysis showed that LP-CQPC11 effectively upregulated SOD1 (Cu/Zn-SOD), SOD2 (Mn-SOD), CAT, GSH1 (c-glutamylcysteine synthetase), and GSH2 (glutathione synthetase) protein expression in mouse liver and spleen tissues. These findings suggest that LP-CQPC11 can effectively prevent d-galactose-induced oxidation and aging in mice, and the effect is even better than that of the commonly used Lactobacillus delbruechii subsp. bulgaricus (LDSB) and vitamin C in the industry. Thus, LP-CQPC11 may be potentially employed as a probiotic strain. Full article
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16 pages, 3678 KiB  
Article
Gelation of Poly(Vinylidene Fluoride) Solutions in Native and Organically Modified Silica Nanopores
by Alejandra Espinosa-Dzib and Sergey Vyazovkin
Molecules 2018, 23(11), 3025; https://doi.org/10.3390/molecules23113025 - 20 Nov 2018
Cited by 4 | Viewed by 2576
Abstract
The purpose of this study is to highlight the surface and size effects of the nanopores on the thermodynamics and kinetics of gelation. The effects have been probed by applying differential scanning calorimetry to poly(vinylidene fluoride) solutions in tetraethylene glycol dimethyl ether (tetraglyme) [...] Read more.
The purpose of this study is to highlight the surface and size effects of the nanopores on the thermodynamics and kinetics of gelation. The effects have been probed by applying differential scanning calorimetry to poly(vinylidene fluoride) solutions in tetraethylene glycol dimethyl ether (tetraglyme) and γ-butyrolactone. Nanoconfinement has been accomplished by introducing gels into native and organically modified silica nanopores (4–30 nm). Nanoconfinement has produced two major effects. First, the heat of gelation has decreased three to four times compared to that for the bulk systems. Second, the temperature of gelation has increased by ~40 °C (tetraglyme based systems) and ~70 °C (γ-butyrolactone based systems), the increase being stronger in native nanopores. The effects are discussed in terms of acceleration of gelation due to heterogeneous nucleation at the confining surface, and retardation of gelation due to constricted polymer chain mobility in the middle of the pore volume. Calorimetric data have been subjected to isoconversional kinetics analysis. The obtained temperature dependencies of the activation energies of gelation have been interpreted in the frameworks of the nucleation model of Turnbull and Fisher. The results suggest that nanoconfinement leads to a lowering of both the free energy of nucleation and activation energy of diffusion. Full article
(This article belongs to the Section Physical Chemistry)
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10 pages, 898 KiB  
Article
Six New Phragmalin Limonoids from the Stems of Chukrasia tabularis A. Juss
by Yan-Cui Wang, Fan-Dong Kong, Hao Wang, Wen-Li Mei, Shou-Bai Liu, You-Xing Zhao and Hao-Fu Dai
Molecules 2018, 23(11), 3024; https://doi.org/10.3390/molecules23113024 - 20 Nov 2018
Cited by 8 | Viewed by 3156
Abstract
Six new phragmalin limonoids, named moluccensin Z1 (1), moluccensin Z2 (2), carapanolide Y (3), tabulalin N (4), chukvelutilide A1 (5), and velutinasin J (6), as well as two known compounds, chukvelutilide [...] Read more.
Six new phragmalin limonoids, named moluccensin Z1 (1), moluccensin Z2 (2), carapanolide Y (3), tabulalin N (4), chukvelutilide A1 (5), and velutinasin J (6), as well as two known compounds, chukvelutilide A (7) and velutinasin D (8) were isolated from the stems of Chukrasia tabularis A. Juss. The structures of the new compounds 16 were confirmed by spectroscopic methods, including IR and HRESIMS, as well as 1D and 2D NMR, and by comparisons with the data of known analogues. All compounds were tested for α-glucosidase and acetylcholinesterase inhibitory activities. However, none of the compounds was active against α-glucosidase and acetylcholinesterase in vitro. Full article
(This article belongs to the Special Issue Natural Product Isolation, Identification and Biological Activity)
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9 pages, 770 KiB  
Article
Conversion of Medium-Sized Lactams to α-Vinyl or α-Acetylenyl Azacycles via N,O-Acetal TMS Ethers
by Minjun Kim, Jaebong Jang, Goyoung Choi, Sungkyun Chung, Changjin Lim, Joonseong Hur, Hyun Su Kim, Younghwa Na, Woo Sung Son, Young-Ger Suh, Jong-Wha Jung and Seok-Ho Kim
Molecules 2018, 23(11), 3023; https://doi.org/10.3390/molecules23113023 - 19 Nov 2018
Cited by 5 | Viewed by 3470
Abstract
α-Vinyl or α-acetylenyl azacycles were easily synthesized from 7- to 9-membered lactams and 6- to 9-membered lactams via N,O-acetal trimethylsilyl (TMS) ethers. Organocopper and organostannane reagents afforded reasonable yields for the respective N-acyliminium ion vinylation and acetylenylation intermediates generated [...] Read more.
α-Vinyl or α-acetylenyl azacycles were easily synthesized from 7- to 9-membered lactams and 6- to 9-membered lactams via N,O-acetal trimethylsilyl (TMS) ethers. Organocopper and organostannane reagents afforded reasonable yields for the respective N-acyliminium ion vinylation and acetylenylation intermediates generated from N,O-acetal TMS ethers in the presence of a Lewis acid. Full article
(This article belongs to the Collection Heterocyclic Compounds)
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32 pages, 19004 KiB  
Review
Organophosphine-Catalyzed [4C+X] Annulations
by Yangyan Li, Xiang Chen, Xiaoming Chen and Xiao Shen
Molecules 2018, 23(11), 3022; https://doi.org/10.3390/molecules23113022 - 19 Nov 2018
Cited by 8 | Viewed by 4217
Abstract
In recent years, there have been extraordinary developments of organophosphine-catalyzed reactions. This includes progress in the area of [4C+X] annulations, which are of particular interest due to their potential for the rapid construction of 5–8-membered cyclic products. In this short overview, we summarize [...] Read more.
In recent years, there have been extraordinary developments of organophosphine-catalyzed reactions. This includes progress in the area of [4C+X] annulations, which are of particular interest due to their potential for the rapid construction of 5–8-membered cyclic products. In this short overview, we summarize the remarkable progress, emphasizing reaction mechanisms and key intermediates involved in the processes. The discussion is classified according to the type of electrophilic reactants that acted as C4 synthons in the annulation process, in the order of α-alkyl allenoates, γ-alkyl allenoates, α-methyl allene ketones, β′-OAc allenoate, δ-OAc allenoate, activated dienes and cyclobutenones. Full article
(This article belongs to the Special Issue Sustainable Synthesis)
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15 pages, 8241 KiB  
Article
Synthesis and Anticancer Activity Evaluation of Hydrolyzed Derivatives of Panaxnotoginseng Saponins
by Lei Xu, Shengnan Xiao, Weihui Yuan, Jiongmo Cui, Guangyue Su and Yuqing Zhao
Molecules 2018, 23(11), 3021; https://doi.org/10.3390/molecules23113021 - 19 Nov 2018
Cited by 12 | Viewed by 3517
Abstract
To increase the antitumor activity of ginsenosides and acetylsalicylic acid, acid hydrolysis products of Panaxnotoginseng saponin were used as raw materials to be combined with salicylic acid to obtain ginsenoside salicylic acid derivatives. All derivatives were assessed for anti-cancer activity. A total of [...] Read more.
To increase the antitumor activity of ginsenosides and acetylsalicylic acid, acid hydrolysis products of Panaxnotoginseng saponin were used as raw materials to be combined with salicylic acid to obtain ginsenoside salicylic acid derivatives. All derivatives were assessed for anti-cancer activity. A total of 20 target compounds were designed and synthesized. The cytotoxic activity on five cancer cell lines, including human colon cancer (HT-29), gastric cancer (BGC-823), cervical cancer (Hela), human breast cancer (MCF-7), human lung cancer cells (A549), and two normal cancer cell lines (human gastric epithelial cells (GES-1), and human ovarian epithelial cells (IOSE144)) was evaluated following treatment with the compounds. The results showed that all compounds inhibited the growth of cancer cells. Compounds 1a, 3a, 7a, 1b, 2b, 3b and 8b showed strong anticancer activity. For MCF-7 cells, compound 3b showed the strongest inhibitory activity, IC50 = 2.56 ± 0.09 μM. In the cytotoxicity test, all compounds showed low toxicity or no toxicity (IC50 > 100 μM). In addition, a cell cycle distribution assay and wound healing assay demonstrated that compound 3b specifically inhibited MCF-7 proliferation and migration ability. Our results indicate that compound 3b represents a promising compound for further cancer studies. Full article
(This article belongs to the Section Natural Products Chemistry)
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