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Molecules, Volume 22, Issue 1 (January 2017) – 185 articles

Cover Story (view full-size image): Cyclodextrins are able to encapsulate water-soluble phosphanes in their cavity even when these phosphanes are coordinated to a transition metal. The supramolecular organometallic complexes resulting from this interaction can then lead to the decoordination of phosphanes from the metal center. Cyclodextrins are therefore original promotors to obtain metals with two coordination spheres or unsaturated metal complexes. View this paper.
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627 KiB  
Review
Pomegranate for Prevention and Treatment of Cancer: An Update
by Pooja Sharma, Sarah F. McClees and Farrukh Afaq
Molecules 2017, 22(1), 177; https://doi.org/10.3390/molecules22010177 - 24 Jan 2017
Cited by 190 | Viewed by 32347
Abstract
Cancer is the second leading cause of death in the United States, and those who survive cancer may experience lasting difficulties, including treatment side effects, as well as physical, cognitive, and psychosocial struggles. Naturally-occurring agents from dietary fruits and vegetables have received considerable [...] Read more.
Cancer is the second leading cause of death in the United States, and those who survive cancer may experience lasting difficulties, including treatment side effects, as well as physical, cognitive, and psychosocial struggles. Naturally-occurring agents from dietary fruits and vegetables have received considerable attention for the prevention and treatment of cancers. These natural agents are safe and cost efficient in contrast to expensive chemotherapeutic agents, which may induce significant side effects. The pomegranate (Punica granatum L.) fruit has been used for the prevention and treatment of a multitude of diseases and ailments for centuries in ancient cultures. Pomegranate exhibits strong antioxidant activity and is a rich source of anthocyanins, ellagitannins, and hydrolysable tannins. Studies have shown that the pomegranate fruit as well as its juice, extract, and oil exert anti-inflammatory, anti-proliferative, and anti-tumorigenic properties by modulating multiple signaling pathways, which suggest its use as a promising chemopreventive/chemotherapeutic agent. This review summarizes preclinical and clinical studies highlighting the role of pomegranate in prevention and treatment of skin, breast, prostate, lung, and colon cancers. Full article
(This article belongs to the Special Issue Cancer Chemoprevention)
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650 KiB  
Article
Isolation and Characterization of a Phaseolus vulgaris Trypsin Inhibitor with Antiproliferative Activity on Leukemia and Lymphoma Cells
by Miao Li, Qin Liu, Yajuan Cui, Dong Li, Hexiang Wang and Tzi Bun Ng
Molecules 2017, 22(1), 187; https://doi.org/10.3390/molecules22010187 - 23 Jan 2017
Cited by 10 | Viewed by 5874
Abstract
A 17.5-kDa trypsin inhibitor was purified from Phaseolus vulgaris cv. “gold bean” with an isolation protocol including ion exchange chromatography on DEAE-cellulose (Diethylaminoethyl-cellulose), affinity chromatography on Affi-gel blue gel, ion exchange chromatography on SP-sepharose (Sulfopropyl-sepharose), and gel filtration by FPLC (Fast protein liquid [...] Read more.
A 17.5-kDa trypsin inhibitor was purified from Phaseolus vulgaris cv. “gold bean” with an isolation protocol including ion exchange chromatography on DEAE-cellulose (Diethylaminoethyl-cellulose), affinity chromatography on Affi-gel blue gel, ion exchange chromatography on SP-sepharose (Sulfopropyl-sepharose), and gel filtration by FPLC (Fast protein liquid chromatography) on Superdex 75. It dose-dependently inhibited trypsin with an IC50 value of 0.4 μM, and this activity was reduced in the presence of dithiothreitol in a dose- and time-dependent manner, signifying the importance of the disulfide linkage to the activity. It inhibited [methyl-3H] thymidine incorporation by leukemia L1210 cells and lymphoma MBL2 cells with an IC50 value of 2.3 μM and 2.5 μM, respectively. The inhibitor had no effect on fungal growth and the activities of various viral enzymes when tested up to 100 μM. Full article
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1865 KiB  
Communication
Co-Immobilization of Enzymes and Magnetic Nanoparticles by Metal-Nucleotide Hydrogelnanofibers for Improving Stability and Recycling
by Chunfang Li, Shuhui Jiang, Xinying Zhao and Hao Liang
Molecules 2017, 22(1), 179; https://doi.org/10.3390/molecules22010179 - 23 Jan 2017
Cited by 47 | Viewed by 8764
Abstract
In this paper we report a facile method for preparing co-immobilized enzyme and magnetic nanoparticles (MNPs) using metal coordinated hydrogel nanofibers. Candida rugosa lipase (CRL) was selected as guest protein. For good aqueous dispersity, low price and other unique properties, citric acid-modified magnetic [...] Read more.
In this paper we report a facile method for preparing co-immobilized enzyme and magnetic nanoparticles (MNPs) using metal coordinated hydrogel nanofibers. Candida rugosa lipase (CRL) was selected as guest protein. For good aqueous dispersity, low price and other unique properties, citric acid-modified magnetic iron oxide nanoparticles (CA-Fe3O4 NPs) have been widely used for immobilizing enzymes. As a result, the relative activity of CA-Fe3O4@Zn/AMP nanofiber-immobilized CRL increased by 8-fold at pH 10.0 and nearly 1-fold in a 50 °C water bath after 30 min, compared to free CRL. Moreover, the immobilized CRL had excellent long-term storage stability (nearly 80% releative activity after storage for 13 days). This work indicated that metal-nucleotide nanofibers could efficiently co-immobilize enzymes and MNPs simultaneously, and improve the stability of biocatalysts. Full article
(This article belongs to the Special Issue Enzyme Immobilization 2016)
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8037 KiB  
Review
Research Advances and Detection Methodologies for Microbe-Derived Acetylcholinesterase Inhibitors: A Systemic Review
by Jingqian Su, Huiying Liu, Kai Guo, Long Chen, Minhe Yang and Qi Chen
Molecules 2017, 22(1), 176; https://doi.org/10.3390/molecules22010176 - 23 Jan 2017
Cited by 29 | Viewed by 7823
Abstract
Acetylcholinesterase inhibitors (AChEIs) are an attractive research subject owing to their potential applications in the treatment of neurodegenerative diseases. Fungi and bacteria are major producers of AChEIs. Their active ingredients of fermentation products include alkaloids, terpenoids, phenylpropanoids, and steroids. A variety of in [...] Read more.
Acetylcholinesterase inhibitors (AChEIs) are an attractive research subject owing to their potential applications in the treatment of neurodegenerative diseases. Fungi and bacteria are major producers of AChEIs. Their active ingredients of fermentation products include alkaloids, terpenoids, phenylpropanoids, and steroids. A variety of in vitro acetylcholinesterase inhibitor assays have been developed and used to measure the activity of acetylcholinesterases, including modified Ellman’s method, thin layer chromatography bioautography, and the combined liquid chromatography-mass spectrometry/modified Ellman’s method. In this review, we provide an overview of the different detection methodologies, the microbe-derived AChEIs, and their producing strains. Full article
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Article
Highly Efficient Enzymatic Preparation of Daidzein in Deep Eutectic Solvents
by Qi-Bin Cheng and Li-Wei Zhang
Molecules 2017, 22(1), 186; https://doi.org/10.3390/molecules22010186 - 22 Jan 2017
Cited by 28 | Viewed by 6814
Abstract
Daidzein, which is scarce in nature, has gained significant attention due to its superior biological activity and bioavailability compared with daidzin. So far, it has been widely used in the medicine and health care products industries. The enzymatic approach for the preparation of [...] Read more.
Daidzein, which is scarce in nature, has gained significant attention due to its superior biological activity and bioavailability compared with daidzin. So far, it has been widely used in the medicine and health care products industries. The enzymatic approach for the preparation of daidzein has prevailed, benefitted by its high efficiency and eco-friendly nature. Our present research aimed at providing a preparation method of daidzein by enzymatic hydrolysis of daidzin in a new “green” reaction medium-deep eutectic solvents (DESs). Herein, the DESs were screened via evaluating enzyme activity, enzyme stability and the substrate solubility, and the DES (ChCl/EG 2:1, 30 vol %) was believed to be the most appropriate co-solvent to improve the bioconversion efficiency. Based on the yield of daidzein, response surface methodology (RSM) was employed to model and optimize the reaction parameters. Under these optimum process conditions, the maximum yield of 97.53% was achieved and the purity of daidzein crude product reached more than 70%, which is more efficient than conversions in DESs-free buffer. Importantly, it has been shown that DESs medium could be reused for six batches of the process with a final conversion of above 50%. The results indicated that this procedure could be considered a mild, environmentally friendly, highly efficient approach to the economical production of daidzein, with a simple operation process and without any harmful reagents being involved. Full article
(This article belongs to the Special Issue Ionic Liquids and Deep Eutectic Solvents for Synthesis, Materials and Energy)
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Article
Alkylglycerol Derivatives, a New Class of Skin Penetration Modulators
by Sergio Alberto Bernal-Chávez, Lilia Yazmín Pérez-Carreto, María Guadalupe Nava-Arzaluz and Adriana Ganem-Rondero
Molecules 2017, 22(1), 185; https://doi.org/10.3390/molecules22010185 - 22 Jan 2017
Cited by 6 | Viewed by 6816
Abstract
The absorption modulating activity of two alkylglycerol derivatives (batyl and chimyl alcohol) on skin barrier properties was evaluated. Biophysical tests such as transepidermal water loss (TEWL) and attenuated total reflectance–Fourier transform infrared (ATR-FTIR) spectroscopy, as well as in vitro skin permeation studies, were [...] Read more.
The absorption modulating activity of two alkylglycerol derivatives (batyl and chimyl alcohol) on skin barrier properties was evaluated. Biophysical tests such as transepidermal water loss (TEWL) and attenuated total reflectance–Fourier transform infrared (ATR-FTIR) spectroscopy, as well as in vitro skin permeation studies, were performed in order to determine the effect of these compounds as chemical absorption modulators. Four drugs were used as models: three NSAIDS (diclofenac, naproxen, and piroxicam) and glycyrrhizic acid. The results showed that treatment of the skin with alkylglycerols caused (i) a reduction on the amount of drug permeated; (ii) a reduction in TEWL; and (iii) changes in the ATR-FTIR peaks of stratum corneum lipids, indicative of a more ordered structure. All of these findings confirm that alkyl glycerols have an absorption retarding effect on the drugs tested. Such effects are expected to give rise to important applications in the pharmaceutical and cosmetic sectors, in cases where it is desirable for the drug to remain in the superficial layers of the skin to achieve a local effect. Full article
(This article belongs to the Special Issue Transdermal Delivery Systems: Current Landscape and Trends)
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3288 KiB  
Article
Synthesis and Characterization of Waterborne Fluoropolymers Prepared by the One-Step Semi-Continuous Emulsion Polymerization of Chlorotrifluoroethylene, Vinyl Acetate, Butyl Acrylate, Veova 10 and Acrylic Acid
by Hongzhu Liu, Jiming Bian, Zhonggang Wang and Chuan-Jin Hou
Molecules 2017, 22(1), 184; https://doi.org/10.3390/molecules22010184 - 22 Jan 2017
Cited by 13 | Viewed by 8790
Abstract
Waterborne fluoropolymer emulsions were synthesized using the one-step semi-continuous seed emulsion polymerization of chlorotrifluoroethylene (CTFE), vinyl acetate (VAc), n-butyl acrylate (BA), Veova 10, and acrylic acid (AA). The main physical parameters of the polymer emulsions were tested and analyzed. Characteristics of the [...] Read more.
Waterborne fluoropolymer emulsions were synthesized using the one-step semi-continuous seed emulsion polymerization of chlorotrifluoroethylene (CTFE), vinyl acetate (VAc), n-butyl acrylate (BA), Veova 10, and acrylic acid (AA). The main physical parameters of the polymer emulsions were tested and analyzed. Characteristics of the polymer films such as thermal stability, glass transition temperature, film-forming properties, and IR spectrum were studied. Meanwhile, the weatherability of fluoride coatings formulated by the waterborne fluoropolymer and other coatings were evaluated by the quick ultraviolet (QUV) accelerated weathering test, and the results showed that the fluoropolymer with more than 12% fluoride content possessed outstanding weather resistance. Moreover, scale-up and industrial-scale experiments of waterborne fluoropolymer emulsions were also performed and investigated. Full article
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3585 KiB  
Article
Phloretin Exerts Anti-Tuberculosis Activity and Suppresses Lung Inflammation
by Dasom Jeon, Min-Cheol Jeong, Hum Nath Jnawali, Chulhee Kwak, Sungwon Ryoo, In Duk Jung and Yangmee Kim
Molecules 2017, 22(1), 183; https://doi.org/10.3390/molecules22010183 - 22 Jan 2017
Cited by 27 | Viewed by 7597
Abstract
An increase in the prevalence of the drug-resistant Mycobacteria tuberculosis necessitates developing new types of anti-tuberculosis drugs. Here, we found that phloretin, a naturally-occurring flavonoid, has anti-mycobacterial effects on H37Rv, multi-drug-, and extensively drug-resistant clinical isolates, with minimum inhibitory concentrations of 182 and [...] Read more.
An increase in the prevalence of the drug-resistant Mycobacteria tuberculosis necessitates developing new types of anti-tuberculosis drugs. Here, we found that phloretin, a naturally-occurring flavonoid, has anti-mycobacterial effects on H37Rv, multi-drug-, and extensively drug-resistant clinical isolates, with minimum inhibitory concentrations of 182 and 364 μM, respectively. Since Mycobacteria cause lung inflammation that contributes to tuberculosis pathogenesis, anti-inflammatory effects of phloretin in interferon-γ-stimulated MRC-5 human lung fibroblasts and lipopolysaccharide (LPS)-stimulated dendritic cells were investigated. The release of interleukin (IL)-1β, IL-12, and tumor necrosis factor (TNF)-α was inhibited by phloretin. The mRNA levels of IL-1β, IL-6, IL-12, TNF-α, and matrix metalloproteinase-1, as well as p38 mitogen-activated protein kinase and extracellular signal-regulated kinase phosphorylation, were suppressed. A mouse in vivo study of LPS-stimulated lung inflammation showed that phloretin effectively suppressed the levels of TNF-α, IL-1β, and IL-6 in lung tissue with low cytotoxicity. Phloretin was found to bind M. tuberculosis β-ketoacyl acyl carrier protein synthase III (mtKASIII) with high affinity (7.221 × 107 M−1); a binding model showed hydrogen bonding of A-ring 2′-hydroxy and B-ring 4-hydroxy groups of phloretin with Asn261 and Cys122 of mtKASIII, implying that mtKASIII can be a potential target protein. Therefore, phloretin can be a useful dietary natural product with anti-tuberculosis benefits. Full article
(This article belongs to the Special Issue Structure-Activity Relationship of Natural Products)
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6023 KiB  
Article
The Influence of Chitosan Cross-linking on the Properties of Alginate Microparticles with Metformin Hydrochloride—In Vitro and In Vivo Evaluation
by Marta Szekalska, Katarzyna Sosnowska, Agnieszka Zakrzeska, Irena Kasacka, Alicja Lewandowska and Katarzyna Winnicka
Molecules 2017, 22(1), 182; https://doi.org/10.3390/molecules22010182 - 22 Jan 2017
Cited by 31 | Viewed by 7555
Abstract
Sodium alginate is a polymer with unique ability to gel with different cross-linking agents in result of ionic and electrostatic interactions. Chitosan cross-linked alginate provides improvement of swelling and mucoadhesive properties and might be used to design sustained release dosage forms. Therefore, the [...] Read more.
Sodium alginate is a polymer with unique ability to gel with different cross-linking agents in result of ionic and electrostatic interactions. Chitosan cross-linked alginate provides improvement of swelling and mucoadhesive properties and might be used to design sustained release dosage forms. Therefore, the aim of this research was to develop and evaluate possibility of preparing chitosan cross-linked alginate microparticles containing metformin hydrochloride by the spray-drying method. In addition, influence of cross-linking agent on the properties of microparticles was evaluated. Formulation of microparticles prepared by the spray drying of 2% alginate solution cross-linked by 0.1% chitosan was characterized by good mucoadhesive properties, high drug loading and prolonged metformin hydrochloride release. It was shown that designed microparticles reduced rat glucose blood level, delayed absorption of metformin hydrochloride and provided stable plasma drug concentration. Additionally, histopathological studies of pancreas, liver and kidneys indicated that all prepared microparticles improved degenerative changes in organs of diabetic rats. Moreover, no toxicity effect and no changes in rats behavior after oral administration of chitosan cross-linked alginate microparticles were noted. Full article
(This article belongs to the Special Issue Natural Products and Chronic Diseases)
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1641 KiB  
Article
A Method for LC-MS/MS Profiling of Coumarins in Zanthoxylum zanthoxyloides (Lam.) B. Zepernich and Timler Extracts and Essential Oils
by Yoro Tine, Franck Renucci, Jean Costa, Alassane Wélé and Julien Paolini
Molecules 2017, 22(1), 174; https://doi.org/10.3390/molecules22010174 - 22 Jan 2017
Cited by 47 | Viewed by 10302
Abstract
The metabolites from the coumarin class, present in tissues of plants belonging mainly to the Rutaceae and Apiaceae families, included compounds with high chemical diversity such as simple coumarins and furocoumarins. These health-promoting components are recognized for their valuable biological activities in herbal [...] Read more.
The metabolites from the coumarin class, present in tissues of plants belonging mainly to the Rutaceae and Apiaceae families, included compounds with high chemical diversity such as simple coumarins and furocoumarins. These health-promoting components are recognized for their valuable biological activities in herbal preparations but also for their phototoxic effects. In this work, a targeted liquid chromatography (LC) coupled with tandem mass spectrometry (MS2) was developed for the screening of 39 reference standards of coumarins and furocoumarins in essential oils and plant extracts. Chromatographic separation was accomplished on reversed phase column using water/acetonitrile as the mobile phase and detection was performed on a hybrid QqQ/linear ion trap spectrometer fitted with an atmospheric pressure chemical ionization (APCI) source operating in positive ion mode. This analytical approach was applied to investigate the coumarin compositions of fruit essential oils and methanolic extracts obtained from separated parts (fruit, leaf, stem, trunk, and root) of Zanthoxylum zanthoxyloides. Ten coumarins and six furanocoumarins were reported in this species and data analyses were used to assess the suitability of these compounds to the metabolomics-based differentiation of plant organs. The quantification criteria of the metabolites in extract samples included linearity, limit of quantification, limit of detection, and matrix effect were validated. As reported for other species of the Rutaceae family, the concentration of coumarins was drastically higher in Z. zanthoxyloides fruits than in other plant organs. Full article
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205 KiB  
Review
Detection of Reactive Oxygen and Nitrogen Species by Electron Paramagnetic Resonance (EPR) Technique
by Sibel Suzen, Hande Gurer-Orhan and Luciano Saso
Molecules 2017, 22(1), 181; https://doi.org/10.3390/molecules22010181 - 21 Jan 2017
Cited by 102 | Viewed by 9567
Abstract
During the last decade there has been growing interest in physical-chemical oxidation processes and the behavior of free radicals in living systems. Radicals are known as intermediate species in a variety of biochemical reactions. Numerous techniques, assays and biomarkers have been used to [...] Read more.
During the last decade there has been growing interest in physical-chemical oxidation processes and the behavior of free radicals in living systems. Radicals are known as intermediate species in a variety of biochemical reactions. Numerous techniques, assays and biomarkers have been used to measure reactive oxygen and nitrogen species (ROS and RNS), and to examine oxidative stress. However, many of these assays are not entirely satisfactory or are used inappropriately. The purpose of this chapter is to review current EPR (Electron Paramagnetic Resonance) spectroscopy methods for measuring ROS, RNS, and their secondary products, and to discuss the strengths and limitations of specific methodological approaches. Full article
(This article belongs to the Special Issue Chemistry and Pharmacology of Modulators of Oxidative Stress)
977 KiB  
Article
A New Human Cancer Cell Proliferation Inhibition Sesquiterpene, Dryofraterpene A, from Medicinal Plant Dryopteris fragrans (L.) Schott
by Zheng-Chang Zhong, Dan-Dan Zhao, Zhen-Dong Liu, Shuai Jiang and Yan-Long Zhang
Molecules 2017, 22(1), 180; https://doi.org/10.3390/molecules22010180 - 21 Jan 2017
Cited by 21 | Viewed by 5200
Abstract
The global burden of cancer continues to increase largely with the aging and growth of the world population. The purpose of the present work was to find new anticancer molecules from a natural source. We utilized chromatographic methods to isolate compounds from medicinal [...] Read more.
The global burden of cancer continues to increase largely with the aging and growth of the world population. The purpose of the present work was to find new anticancer molecules from a natural source. We utilized chromatographic methods to isolate compounds from medicinal plant Dryopteris fragrans (L.) Schott. The structure of the new compounds was determined by spectroscopic and spectrometric data (1D NMR, 2D NMR, and EMI-MS). Their anti-proliferation effects against five human cancer cell lines including A549, MCF7, HepG2, HeLa, and PC-3 were evaluated by CCK-8 andlactate dehydrogenase (LDH) assay. A new sesquiterpene, (7S, 10S)-2,3-dihydroxy-calamenene-15-carboxylic acid methyl ester (1), and two known compounds (2 and 3) were isolated. The new sesquiterpene was named dryofraterpene A and significantly inhibited cancer cell proliferation without any obvious necrosis below a 10 μM concentration. In conclusion, a novel anticancer sesquiterpene together with two known compounds was isolated, which might be a promising lead compound for the treatment of cancer. Full article
(This article belongs to the Section Natural Products Chemistry)
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3991 KiB  
Article
Nano-Structural Investigation on Cellulose Highly Dissolved in Ionic Liquid: A Small Angle X-ray Scattering Study
by Takatsugu Endo, Shota Hosomi, Shunsuke Fujii, Kazuaki Ninomiya and Kenji Takahashi
Molecules 2017, 22(1), 178; https://doi.org/10.3390/molecules22010178 - 21 Jan 2017
Cited by 19 | Viewed by 6603
Abstract
We investigated nano-structural changes of cellulose dissolved in 1-ethyl-3-methylimidazolium acetate—an ionic liquid (IL)—using a small angle X-ray scattering (SAXS) technique over the entire concentration range (0–100 mol %). Fibril structures of cellulose disappeared at 40 mol % of cellulose, which is a significantly [...] Read more.
We investigated nano-structural changes of cellulose dissolved in 1-ethyl-3-methylimidazolium acetate—an ionic liquid (IL)—using a small angle X-ray scattering (SAXS) technique over the entire concentration range (0–100 mol %). Fibril structures of cellulose disappeared at 40 mol % of cellulose, which is a significantly higher concentration than the maximum concentration of dissolution (24–28 mol %) previously determined in this IL. This behavior is explained by the presence of the anion bridging, whereby an anion prefers to interact with multiple OH groups of different cellulose molecules at high concentrations, discovered in our recent work. Furthermore, we observed the emergence of two aggregated nano-structures in the concentration range of 30–80 mol %. The diameter of one structure was 12–20 nm, dependent on concentration, which is ascribed to cellulose chain entanglement. In contrast, the other with 4.1 nm diameter exhibited concentration independence and is reminiscent of a cellulose microfibril, reflecting the occurrence of nanofibrillation. These results contribute to an understanding of the dissolution mechanism of cellulose in ILs. Finally, we unexpectedly proposed a novel cellulose/IL composite: the cellulose/IL mixtures of 30–50 mol % that possess liquid crystallinity are sufficiently hard to be moldable. Full article
(This article belongs to the Special Issue Ionic Liquids and Deep Eutectic Solvents for Synthesis, Materials and Energy)
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Article
New Pesticidal Diterpenoids from Vellozia gigantea (Velloziaceae), an Endemic Neotropical Plant Living in the Endangered Brazilian Biome Rupestrian Grasslands
by Mariana C. Ferreira, Charles L. Cantrell, Stephen O. Duke, Abbas Ali and Luiz H. Rosa
Molecules 2017, 22(1), 175; https://doi.org/10.3390/molecules22010175 - 21 Jan 2017
Cited by 13 | Viewed by 7461
Abstract
Vellozia gigantea is a rare, ancient, and endemic neotropical plant present in the Brazilian Rupestrian grasslands. The dichloromethane extract of V. gigantea adventitious roots was phytotoxic against Lactuca sativa, Agrostis stolonifera, and Lemna paucicostata, and showed larvicidal activity against Aedes [...] Read more.
Vellozia gigantea is a rare, ancient, and endemic neotropical plant present in the Brazilian Rupestrian grasslands. The dichloromethane extract of V. gigantea adventitious roots was phytotoxic against Lactuca sativa, Agrostis stolonifera, and Lemna paucicostata, and showed larvicidal activity against Aedes aegypti. Phytotoxicity bioassay-directed fractionation of the extract revealed one new isopimaradiene, 8(9),15-isopimaradien-1,3,7,11-tetraone, and three new cleistanthane diterpenoids, 7-oxo-8,11,13-cleistanthatrien-3-ol, 3,20-epoxy-7-oxo-8,11,13-cleistanthatrien-3-ol, and 20-nor-3,7-dioxo-1,8,11,13-cleistanthatetraen-10-ol. These new structures are proposed based on interpretation of 1H, 13C, COSY, NOESY, HSQC, and HMBC NMR data. 8(9),15-isopimaradien-1,3,7,11-tetraone was especially phytotoxic with an IC50 value (30 μM) comparable to those of commercial herbicides clomazone, EPTC, and naptalam. In addition, 7-oxo-8,11,13-cleistanthatrien-3-ol provided 100% mortality at a concentration of 125 ppm against one-day-old Ae. aegypti larvae. Our results show that ancient and unique plants, like the endangered narrowly endemic neotropical species V. gigantea present in the Rupestrian grasslands, should also be protected because they can be sources of new bioactive compounds. Full article
(This article belongs to the Special Issue Special Issue in Honor of Professor Nikolaus (Klaus) Fischer on the Occasion of His 80th Birthday)
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994 KiB  
Article
Hyperforin Exhibits Antigenotoxic Activity on Human and Bacterial Cells
by Petronela Imreova, Jana Feruszova, Stanislav Kyzek, Kristina Bodnarova, Martina Zduriencikova, Katarina Kozics, Pavel Mucaji, Eliska Galova, Andrea Sevcovicova, Eva Miadokova and Ivan Chalupa
Molecules 2017, 22(1), 167; https://doi.org/10.3390/molecules22010167 - 21 Jan 2017
Cited by 16 | Viewed by 5785
Abstract
Hyperforin (HF), a substance that accumulates in the leaves and flowers of Hypericum perforatum L. (St. John’s wort), consists of a phloroglucinol skeleton with lipophilic isoprene chains. HF exhibits several medicinal properties and is mainly used as an antidepressant. So far, the antigenotoxicity [...] Read more.
Hyperforin (HF), a substance that accumulates in the leaves and flowers of Hypericum perforatum L. (St. John’s wort), consists of a phloroglucinol skeleton with lipophilic isoprene chains. HF exhibits several medicinal properties and is mainly used as an antidepressant. So far, the antigenotoxicity of HF has not been investigated at the level of primary genetic damage, gene mutations, and chromosome aberrations, simultaneously. The present work is designed to investigate the potential antigenotoxic effects of HF using three different experimental test systems. The antigenotoxic effect of HF leading to the decrease of primary/transient promutagenic genetic changes was detected by the alkaline comet assay on human lymphocytes. The HF antimutagenic effect leading to the reduction of gene mutations was assessed using the Ames test on the standard Salmonella typhimurium (TA97, TA98, and TA100) bacterial strains, and the anticlastogenic effect of HF leading to the reduction of chromosome aberrations was evaluated by the in vitro mammalian chromosome aberration test on the human tumor cell line HepG2 and the non-carcinogenic cell line VH10. Our findings provided evidence that HF showed antigenotoxic effects towards oxidative mutagen zeocin in the comet assay and diagnostic mutagen (4-nitroquinoline-1-oxide) in the Ames test. Moreover, HF exhibited an anticlastogenic effect towards benzo(a)pyrene and cisplatin in the chromosome aberration test. Full article
(This article belongs to the Section Natural Products Chemistry)
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Article
Protective Effect of Strawberry Extract against Inflammatory Stress Induced in Human Dermal Fibroblasts
by Massimiliano Gasparrini, Tamara Y. Forbes-Hernandez, Francesca Giampieri, Sadia Afrin, Bruno Mezzetti, Josè L. Quiles, Stefano Bompadre and Maurizio Battino
Molecules 2017, 22(1), 164; https://doi.org/10.3390/molecules22010164 - 21 Jan 2017
Cited by 19 | Viewed by 9823
Abstract
A protracted pro-inflammatory state is a major contributing factor in the development, progression and complication of the most common chronic pathologies. Fruit and vegetables represent the main sources of dietary antioxidants and their consumption can be considered an efficient tool to counteract inflammatory [...] Read more.
A protracted pro-inflammatory state is a major contributing factor in the development, progression and complication of the most common chronic pathologies. Fruit and vegetables represent the main sources of dietary antioxidants and their consumption can be considered an efficient tool to counteract inflammatory states. In this context an evaluation of the protective effects of strawberry extracts on inflammatory stress induced by E. coli LPS on human dermal fibroblast cells was performed in terms of viability assays, ROS and nitrite production and biomarkers of oxidative damage of the main biological macromolecules. The results demonstrated that strawberry extracts exerted an anti-inflammatory effect on LPS-treated cells, through an increase in cell viability, and the reduction of ROS and nitrite levels, and lipid, protein and DNA damage. This work showed for the first time the potential health benefits of strawberry extract against inflammatory and oxidative stress in LPS-treated human dermal fibroblast cells. Full article
(This article belongs to the Section Natural Products Chemistry)
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4198 KiB  
Article
Adsorption Properties of Nano-MnO2–Biochar Composites for Copper in Aqueous Solution
by Li Zhou, Yifan Huang, Weiwen Qiu, Zhanxiang Sun, Zhongqi Liu and Zhengguo Song
Molecules 2017, 22(1), 173; https://doi.org/10.3390/molecules22010173 - 20 Jan 2017
Cited by 102 | Viewed by 9331
Abstract
There is a continuing need to develop effective materials for the environmental remediation of copper-contaminated sites. Nano-MnO2–biochar composites (NMBCs) were successfully synthesized through the reduction of potassium permanganate by ethanol in a biochar suspension. The physicochemical properties and morphology of NMBCs [...] Read more.
There is a continuing need to develop effective materials for the environmental remediation of copper-contaminated sites. Nano-MnO2–biochar composites (NMBCs) were successfully synthesized through the reduction of potassium permanganate by ethanol in a biochar suspension. The physicochemical properties and morphology of NMBCs were examined, and the Cu(II) adsorption properties of this material were determined using various adsorption isotherms and kinetic models. The adsorption capacity of NMBCs for Cu(II), which was enhanced by increasing the pH from 3 to 6, was much larger than that of biochar or nano-MnO2. The maximum adsorption capacity of NMBCs for Cu(II) was 142.02 mg/g, which was considerably greater than the maximum adsorption capacities of biochar (26.88 mg/g) and nano-MnO2 (93.91 mg/g). The sorption process for Cu(II) on NMBCs fitted very well to a pseudo-second-order model (R2 > 0.99). Moreover, this process was endothermic, spontaneous, and hardly influenced by ionic strength. The mechanism of Cu(II) adsorption on NMBCs mainly involves the formation of complexes between Cu(II) and O-containing groups (e.g., COO–Cu and Mn–O–Cu). Thus, NMBCs may serve as effective adsorbents for various environmental applications, such as wastewater treatment or the remediation of copper-contaminated soils. Full article
(This article belongs to the Special Issue Chemicals from Biomass)
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5468 KiB  
Article
Design, Synthesis, and Biological Evaluation of a New Series of Biphenyl/Bibenzyl Derivatives Functioning as Dual Inhibitors of Acetylcholinesterase and Butyrylcholinesterase
by Dong-mei Wang, Bo Feng, Hui Fu, Ai-lin Liu, Lin Wang, Guan-hua Du and Song Wu
Molecules 2017, 22(1), 172; https://doi.org/10.3390/molecules22010172 - 20 Jan 2017
Cited by 13 | Viewed by 5357
Abstract
Alzheimer’s disease (AD), the most common form of dementia in adults, is a progressive neurodegenerative disorder of the brain characterized by loss of memory and steady deterioration of cognition. Here, a series of symmetrical molecules containing biphenyl/bibenzyl scaffolds (12–36) [...] Read more.
Alzheimer’s disease (AD), the most common form of dementia in adults, is a progressive neurodegenerative disorder of the brain characterized by loss of memory and steady deterioration of cognition. Here, a series of symmetrical molecules containing biphenyl/bibenzyl scaffolds (12–36) were designed, synthesized, and evaluated for their ability to inhibit both acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE). A biological evaluation showed that most of these biphenyl derivatives were potent AChE and BuChE inhibitors. Among them, compound 15 displayed the greatest ability to inhibit BuChE (IC50 = 0.74 µM) and was also a good AChE inhibitor (IC50 = 1.18 µM). Compound 19 was not only a potent AChE inhibitor (IC50 = 0.096 µM), but also a mild BuChE inhibitor (IC50 =1.25 µM). Overall, these results suggested that compound 19 may be a promising agent in the treatment of AD. Full article
(This article belongs to the Section Medicinal Chemistry)
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2838 KiB  
Article
In Vitro DNA-Binding, Anti-Oxidant and Anticancer Activity of Indole-2-Carboxylic Acid Dinuclear Copper(II) Complexes
by Xiangcong Wang, Maocai Yan, Qibao Wang, Huannan Wang, Zhengyang Wang, Jiayi Zhao, Jing Li and Zhen Zhang
Molecules 2017, 22(1), 171; https://doi.org/10.3390/molecules22010171 - 20 Jan 2017
Cited by 23 | Viewed by 7161
Abstract
Indole-2-carboxylic acid copper complex (ICA-Cu) was successfully prepared and characterized through elemental analysis, IR, UV-Vis, 1H-NMR, TG analysis, and molar conductance, and its molecular formula was [Cu2(C9H6O2N)4(H2O)2]·2H2 [...] Read more.
Indole-2-carboxylic acid copper complex (ICA-Cu) was successfully prepared and characterized through elemental analysis, IR, UV-Vis, 1H-NMR, TG analysis, and molar conductance, and its molecular formula was [Cu2(C9H6O2N)4(H2O)2]·2H2O. The binding ability of ICA-Cu to calf thymus DNA (CT-DNA) was examined by fluorescence spectrometry and the viscosity method. The results indicated that, upon the addition of increasing amounts of CT-DNA, the excitation and emission intensity of ICA-Cu decreased obviously and the excitation spectra shifted towards a long wavelength. ICA-Cu could displace ethidium bromide (EB) from the EB-DNA system, making the fluorescence intensity of the EB-DNA system decrease sharply; the quenching constant KSV value was 3.99 × 104 M−1. The emission intensity of the ICA-Cu-DNA system was nearly constant, along with the addition of Na+ in a series of concentrations. The fluorescence of the complex could be protected after the complex interacted with DNA. A viscosity measurement further supported the result that the ICA-Cu complex may interact with DNA in an intercalative binding mode. The antioxidant activities of ICA-Cu were evaluated by a 2,2-diphenyl-1-picrylhydrazyl (DPPH) assay, a hydroxyl radical (OH) scavenging assay, and a 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulphonic acid (ABTS) assay. The ICA-Cu exhibited the highest inhibitory effects on the ABTS radical (94% inhibition at 60 µM), followed by OH and DPPH radicals (the degrees of inhibition being 71% and 56%, respectively). The in vitro cytotoxicity activity of ICA-Cu against two human breast cancer cell lines, MDA-MB-231 and MCF-7, was investigated by 3-[4,5-dimethyltiazol2-yl]-2.5-diphenyl-tetrazolium bromide (MTT) assay and cellular morphological analysis. The results showed that, upon increasing the concentration of ICA-Cu, an increase was observed in growth-inhibitory activity and the inhibition percentage were greater than 90% at 20 µM in both cell lines. Also, cellular morphological changes in the two cell lines agreed with the cytotoxicity results. Full article
(This article belongs to the Special Issue Metal Based Drugs: Opportunities and Challenges)
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926 KiB  
Article
Synthesis and Anticancer Activity of New 1-Thia-4-azaspiro[4.5]decane, Their Derived Thiazolopyrimidine and 1,3,4-Thiadiazole Thioglycosides
by Eman M. Flefel, Wael A. El-Sayed, Ashraf M. Mohamed, Walaa I. El-Sofany and Hanem M. Awad
Molecules 2017, 22(1), 170; https://doi.org/10.3390/molecules22010170 - 20 Jan 2017
Cited by 68 | Viewed by 6814
Abstract
New 1-thia-azaspiro[4.5]decane derivatives, their derived thiazolopyrimidine and 1,3,4-thiadiazole compounds were synthesized. The thioglycoside derivatives of the synthesized (1,3,4-thiadiazolyl)thiaazaspiro[4.5]decane and thiazolopyrimidinethione compounds were synthesized by glycosylation reactions using acetylated glycosyl bromides. The anticancer activity of synthesized compounds was studied against the cell culture of [...] Read more.
New 1-thia-azaspiro[4.5]decane derivatives, their derived thiazolopyrimidine and 1,3,4-thiadiazole compounds were synthesized. The thioglycoside derivatives of the synthesized (1,3,4-thiadiazolyl)thiaazaspiro[4.5]decane and thiazolopyrimidinethione compounds were synthesized by glycosylation reactions using acetylated glycosyl bromides. The anticancer activity of synthesized compounds was studied against the cell culture of HepG-2 (human liver hepatocellular carcinoma), PC-3 (human prostate adenocarcinoma) and HCT116 (human colorectal carcinoma) cell lines and a number of compounds showed moderate to high inhibition activities. Full article
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Article
Toxicity of Plant Secondary Metabolites Modulating Detoxification Genes Expression for Natural Red Palm Weevil Pesticide Development
by Ahmed Mohammed AlJabr, Abid Hussain, Muhammad Rizwan-ul-Haq and Hassan Al-Ayedh
Molecules 2017, 22(1), 169; https://doi.org/10.3390/molecules22010169 - 20 Jan 2017
Cited by 55 | Viewed by 7591
Abstract
This study aimed to explore the larvicidal and growth-inhibiting activities, and underlying detoxification mechanism of red palm weevil against phenylpropanoids, an important class of plant secondary metabolites. Toxicity of α-asarone, eugenol, isoeugenol, methyl eugenol, methyl isoeugenol, coumarin, coumarin 6, coniferyl aldehyde, diniconazole, ethyl [...] Read more.
This study aimed to explore the larvicidal and growth-inhibiting activities, and underlying detoxification mechanism of red palm weevil against phenylpropanoids, an important class of plant secondary metabolites. Toxicity of α-asarone, eugenol, isoeugenol, methyl eugenol, methyl isoeugenol, coumarin, coumarin 6, coniferyl aldehyde, diniconazole, ethyl cinnamate, and rosmarinic acid was evaluated by incorporation into the artificial diet. All of the phenylpropanoids exhibited dose- and time-dependent insecticidal activity. Among all the tested phenylpropanoids, coumarin exhibited the highest toxicity by revealing the least LD50 value (0.672 g/L). In addition, the most toxic compound (coumarin) observed in the current study, deteriorated the growth resulting tremendous reduction (78.39%) in efficacy of conversion of digested food (ECD), and (ECI) efficacy of conversion of ingested food (70.04%) of tenth-instar red palm weevil larvae. The energy-deficient red palm weevil larvae through their intrinsic abilities showed enhanced response to their digestibility resulting 27.78% increase in approximate digestibility (AD) compared to control larvae. The detoxification response of Rhynchophorus ferrugineus larvae determined by the quantitative expression of cytochrome P450, esterases, and glutathione S-transferase revealed enhanced expression among moderately toxic and ineffective compounds. These genes especially cytochrome P450 and GST detoxify the target compounds by enhancing their solubility that leads rapid excretion and degradation resulting low toxicity towards red palm weevil larvae. On the other hand, the most toxic (coumarin) silenced the genes involved in the red palm weevil detoxification mechanism. Based on the toxicity, growth retarding, and masking detoxification activities, coumarin could be a useful future natural red palm weevil-controlling agent. Full article
(This article belongs to the Collection Phytochemicals: Biosynthesis, Metabolism and Biological Activities)
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1490 KiB  
Review
A Review of Mid-Infrared and Near-Infrared Imaging: Principles, Concepts and Applications in Plant Tissue Analysis
by Sevgi Türker-Kaya and Christian W. Huck
Molecules 2017, 22(1), 168; https://doi.org/10.3390/molecules22010168 - 20 Jan 2017
Cited by 294 | Viewed by 17750
Abstract
Plant cells, tissues and organs are composed of various biomolecules arranged as structurally diverse units, which represent heterogeneity at microscopic levels. Molecular knowledge about those constituents with their localization in such complexity is very crucial for both basic and applied plant sciences. In [...] Read more.
Plant cells, tissues and organs are composed of various biomolecules arranged as structurally diverse units, which represent heterogeneity at microscopic levels. Molecular knowledge about those constituents with their localization in such complexity is very crucial for both basic and applied plant sciences. In this context, infrared imaging techniques have advantages over conventional methods to investigate heterogeneous plant structures in providing quantitative and qualitative analyses with spatial distribution of the components. Thus, particularly, with the use of proper analytical approaches and sampling methods, these technologies offer significant information for the studies on plant classification, physiology, ecology, genetics, pathology and other related disciplines. This review aims to present a general perspective about near-infrared and mid-infrared imaging/microspectroscopy in plant research. It is addressed to compare potentialities of these methodologies with their advantages and limitations. With regard to the organization of the document, the first section will introduce the respective underlying principles followed by instrumentation, sampling techniques, sample preparations, measurement, and an overview of spectral pre-processing and multivariate analysis. The last section will review selected applications in the literature. Full article
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6847 KiB  
Communication
Characterization of Collagen Peptides in Elaphuri Davidiani Cornu Aqueous Extract with Proliferative Activity on Osteoblasts Using Nano-Liquid Chromatography in Tandem with Orbitrap Mass Spectrometry
by Yanjuan Zhai, Zhenhua Zhu, Yue Zhu, Dawei Qian, Rui Liu, Yunru Peng, Yuhua Ding, Zhen Ouyang and Jin-ao Duan
Molecules 2017, 22(1), 166; https://doi.org/10.3390/molecules22010166 - 20 Jan 2017
Cited by 6 | Viewed by 5918
Abstract
First documented in Shennong Bencao Jing (about 200 B.C.–200 A.D.), Elaphuri Davidiani Cornu (EDC) has been recorded for its effects in strengthening bones and balancing other aspects of overall health for approximately 2000 years. In the present study, our aim was to investigate [...] Read more.
First documented in Shennong Bencao Jing (about 200 B.C.–200 A.D.), Elaphuri Davidiani Cornu (EDC) has been recorded for its effects in strengthening bones and balancing other aspects of overall health for approximately 2000 years. In the present study, our aim was to investigate which are the components of the active EDC fraction by a peptidomic strategy. We explored the extent to which EDC increases the proliferation of osteoblasts by measuring the elevations in osteonectin and type I collagen mRNA levels and characterized it using nano-flow liquid chromatography in tandem with orbitrap mass spectrometry. In total, 272 peptide sequences from collagens were determined. “Hot regions” in parent proteins determined by peptide heat maps which indicated that amino acid sequences in the regions might undergo proteolysis easily and generate peptides. Among the identified peptides, 90.2% were hydrophilic, and the molecular weight of 97.1% of identified peptides was lower than 2000 Da. According to these results, EDC collagen-derived peptides were easily analyzed and identified. Moreover, this methodology is feasible to characterize the active peptides matrices originated from collagen hydrolysates or some other animal horn- derived TCMs. Full article
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4292 KiB  
Article
Green Synthesis and Characterization of Palladium Nanoparticles Using Origanum vulgare L. Extract and Their Catalytic Activity
by Mohammed Rafi Shaik, Zuhur Jameel Qandeel Ali, Mujeeb Khan, Mufsir Kuniyil, Mohamed E. Assal, Hamad Z. Alkhathlan, Abdulrahman Al-Warthan, Mohammed Rafiq H. Siddiqui, Merajuddin Khan and Syed Farooq Adil
Molecules 2017, 22(1), 165; https://doi.org/10.3390/molecules22010165 - 19 Jan 2017
Cited by 111 | Viewed by 12214
Abstract
The synthesis of Palladium (Pd) nanoparticles by green methods has attracted remarkable attention in recent years because of its superiority above chemical approaches, owing to its low cost and ecological compatibility. In this present work, we describe a facile and environmentally friendly synthesis [...] Read more.
The synthesis of Palladium (Pd) nanoparticles by green methods has attracted remarkable attention in recent years because of its superiority above chemical approaches, owing to its low cost and ecological compatibility. In this present work, we describe a facile and environmentally friendly synthesis of Pd nanoparticles (Pd NPs) using an aqueous extract of aerial parts of Origanum vulgare L. (OV) as a bioreductant. This plant is available in many parts of the world as well as in Saudi Arabia and is known to be a rich source of phenolic components, a feature we fruitfully utilized in the synthesis of Pd NPs, using various concentrations of plant extracts. Moreover, the OV extract phytomolecules are not only accountable for the reduction and progression of nanoparticles, but they also act as stabilizing agents, which was confirmed by several characterization methods. The as-synthesized Pd nanoparticles (Pd NPs) were analyzed using ultraviolet-visible spectroscopy (UV-Vis), Fourier-transform infrared spectroscopy (FT-IR), X-ray diffraction (XRD), transmission electron microscopy (TEM), energy-dispersive X-ray spectroscopy (EDX), and thermal gravimetric analysis (TGA). Further, FT-IR study has proven that the OV not merely represents a bioreductant but also functionalizes the nanoparticles. Furthermore, the green synthesized metallic Pd NPs were successfully applied as catalysts for selective oxidation of alcohols. Full article
(This article belongs to the Section Green Chemistry)
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2381 KiB  
Article
Combination of Morroniside and Diosgenin Prevents High Glucose-Induced Cardiomyocytes Apoptosis
by Wen-Xia Pi, Xiao-Peng Feng, Li-Hong Ye and Bao-Chang Cai
Molecules 2017, 22(1), 163; https://doi.org/10.3390/molecules22010163 - 19 Jan 2017
Cited by 45 | Viewed by 6093
Abstract
Cornus officinalis and Dioscorea opposita are two traditional Chinese medicines widely used in China for treating diabetes mellitus and its complications, such as diabetic cardiomyopathy. Morroniside (Mor) of Cornus officinalis and diosgenin (Dio) of Dioscorea opposita formed an innovative formula named M + [...] Read more.
Cornus officinalis and Dioscorea opposita are two traditional Chinese medicines widely used in China for treating diabetes mellitus and its complications, such as diabetic cardiomyopathy. Morroniside (Mor) of Cornus officinalis and diosgenin (Dio) of Dioscorea opposita formed an innovative formula named M + D. The aims of the present study were to investigate myocardial protective effect of M + D on diabetic cardiomyopathy (DCM) through the inhibition of expression levels of caspase-3 protein, and identify the advantage of M + D compared with Mor, Dio, and the positive drug metformin (Met). We detected cell viability, cell apoptosis, intracellular reactive oxygen species (ROS) levels, and the expression levels of Bcl-2, Bax, and caspase-3 protein in rat cardiomyocytes. In result, Mor, Dio, and M + D increased cell viability, inhibited cell apoptosis and decreased ROS levels. Additionally, the expression of Bax and Bcl-2 protein was modulated and the expression levels of caspase-3 protein were markedly decreased. Among the treatment groups, M + D produced the most prominent effects. In conclusion, our data showed for the first time that Mor, Dio, and M + D prevented high glucose (HG)-induced myocardial injury by reducing oxidative stress and apoptosis in rat cardiomyocytes. Among all the groups, M + D produced the strongest effect, while Mor and Dio produced weaker effects. Full article
(This article belongs to the Special Issue Isoprenoid Biosynthesis)
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1058 KiB  
Article
Phenolic Compounds from the Leaves of Castanopsis fargesii
by Yong-Lin Huang, Ya-Feng Wang, Jin-Lei Liu, Lei Wang, Takashi Tanaka, Yue-Yuan Chen, Feng-Lai Lu and Dian-Peng Li
Molecules 2017, 22(1), 162; https://doi.org/10.3390/molecules22010162 - 19 Jan 2017
Cited by 13 | Viewed by 5083
Abstract
In the course of a phytochemical and chemotaxonomical investigation of Castanopsis species (Fagaceae), three new phenolic compounds, (3R,1′S)-[1′-(6″-O-galloyl-β-d-gluco-pyranosyl)oxyethyl]-3-hydroxy-dihydrofuran-2(3H)-one (1), (2R,3S)-2-[2′-(galloyl)oxyethyl]-dihydroxybutanoic acid (2), and (3S [...] Read more.
In the course of a phytochemical and chemotaxonomical investigation of Castanopsis species (Fagaceae), three new phenolic compounds, (3R,1′S)-[1′-(6″-O-galloyl-β-d-gluco-pyranosyl)oxyethyl]-3-hydroxy-dihydrofuran-2(3H)-one (1), (2R,3S)-2-[2′-(galloyl)oxyethyl]-dihydroxybutanoic acid (2), and (3S,4S)-3-hydroxymethyl-3,4-dihydro-5,6,7-trihydroxy-4-(4′-hydroxy-3′-methoxyphenyl)-1H-[2]-benzopyran-1-one (3) were isolated from the fresh leaves of Castanopsis fargesii. In addition, a known phenolic glycoside, gentisic acid 5-O-α-l-rhamnopyranosyl-(1→2)-β-d-glucopyranoside (4) was also isolated and identified. Their structures were elucidated by means of spectroscopic methods including one- and two-dimensional NMR techniques. Full article
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10947 KiB  
Article
Pharmacomodulation of the Antimalarial Plasmodione: Synthesis of Biaryl- and N-Arylalkylamine Analogues, Antimalarial Activities and Physicochemical Properties
by Karène Urgin, Mouhamad Jida, Katharina Ehrhardt, Tobias Müller, Michael Lanzer, Louis Maes, Mourad Elhabiri and Elisabeth Davioud-Charvet
Molecules 2017, 22(1), 161; https://doi.org/10.3390/molecules22010161 - 19 Jan 2017
Cited by 9 | Viewed by 9632
Abstract
With the aim of increasing the structural diversity on the early antimalarial drug plasmodione, an efficient and versatile procedure to prepare a series of biaryl- and N-arylalkylamines as plasmodione analogues is described. Using the naturally occurring and commercially available menadione as starting [...] Read more.
With the aim of increasing the structural diversity on the early antimalarial drug plasmodione, an efficient and versatile procedure to prepare a series of biaryl- and N-arylalkylamines as plasmodione analogues is described. Using the naturally occurring and commercially available menadione as starting material, a 2-step sequence using a Kochi-Anderson reaction and subsequent Pd-catalyzed Suzuki-Miyaura coupling was developed to prepare three representative biphenyl derivatives in good yields for antimalarial evaluation. In addition, synthetic methodologies to afford 3-benzylmenadione derivatives bearing a terminal -N(Me)2 or -N(Et)2 in different positions (ortho, meta and para) on the aryl ring of the benzylic chain of plasmodione were investigated through reductive amination was used as the optimal route to prepare these protonable N-arylalkylamine privileged scaffolds. The antimalarial activities were evaluated and discussed in light of their physicochemical properties. Among the newly synthesized compounds, the para-position of the substituent remains the most favourable position on the benzyl chain and the carbamate -NHBoc was found active both in vitro (42 nM versus 29 nM for plasmodione) and in vivo in Plasmodium berghei-infected mice. The measured acido-basic features of these new molecules support the cytosol-food vacuole shuttling properties of non-protonable plasmodione derivatives essential for redox-cycling. These findings may be useful in antimalarial drug optimization. Full article
(This article belongs to the Special Issue COST CM1307: Targeted Chemotherapy towards Diseases Caused by Endoparasites—Proceedings in Medicinal and Natural Product Chemistry)
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865 KiB  
Review
The Effect of Polyphenols on Protein Degradation Pathways: Implications for Neuroprotection
by Parvana Hajieva
Molecules 2017, 22(1), 159; https://doi.org/10.3390/molecules22010159 - 19 Jan 2017
Cited by 36 | Viewed by 9335
Abstract
Human neurodegenerative diseases are accompanied by accumulation of heavily oxidized and aggregated proteins. However, the exact molecular reason is not fully elucidated yet. Insufficient cellular protein quality control is thought to play an important role in accumulating covalently oxidized misfolded proteins. Pharmacologically active [...] Read more.
Human neurodegenerative diseases are accompanied by accumulation of heavily oxidized and aggregated proteins. However, the exact molecular reason is not fully elucidated yet. Insufficient cellular protein quality control is thought to play an important role in accumulating covalently oxidized misfolded proteins. Pharmacologically active polyphenols and their derivatives exhibit potential for preventive and therapeutic purposes against protein aggregation during neurodegeneration. Although these compounds act on various biochemical pathways, their role in stabilizing the protein degradation machinery at different stages may be an attractive therapeutical strategy to halt the accumulation of misfolded proteins. This review evaluates and discusses the existing scientific literature on the effect of polyphenols on three major protein degradation pathways: chaperone-mediated autophagy, the proteasome and macroautophagy. The results of these studies demonstrate that phenolic compounds are able to influence the major protein degradation pathways at different levels. Full article
(This article belongs to the Collection Neuroprotection Mediated by Natural Products and Their Chemical Derivatives)
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2181 KiB  
Article
Ultrafast Electronic Deactivation Dynamics of Xanthosine Monophosphate
by Katharina Röttger, Rebecca Stellmacher, Mayra C. Stuhldreier and Friedrich Temps
Molecules 2017, 22(1), 160; https://doi.org/10.3390/molecules22010160 - 18 Jan 2017
Cited by 3 | Viewed by 6734
Abstract
Ultrafast energy dissipation is a crucial factor for the photostability of DNA and RNA, but even some of the key electronic deactivation pathways in monomeric nucleic acid building stones are still controversial. Here, we report on the excited-state dynamics of the rare nucleotide [...] Read more.
Ultrafast energy dissipation is a crucial factor for the photostability of DNA and RNA, but even some of the key electronic deactivation pathways in monomeric nucleic acid building stones are still controversial. Here, we report on the excited-state dynamics of the rare nucleotide xanthosine monophosphate as a function of deprotonation state (XMP vs. XMP − ) and excitation wavelength ( λ pump = 278–243 nm) by femtosecond time-resolved fluorescence and absorption spectroscopy. We show that the predominating relaxation channel leads to a return of the photo-excited molecules to the electronic ground state in τ∼1 ps. The mechanism likely involves an out-of-plane deformation of the five-membered ring, different from the main electronic deactivation pathways in the canonical purine bases adenine and guanine. The results are discussed in terms of the structural and electronic differences of XMP compared to the canonical nucleotides. Full article
(This article belongs to the Special Issue Experimental and Computational Photochemistry of Bioorganic Molecules)
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Article
Preparative Scale Resolution of Enantiomers Enables Accelerated Drug Discovery and Development
by Hanna Leek and Shalini Andersson
Molecules 2017, 22(1), 158; https://doi.org/10.3390/molecules22010158 - 18 Jan 2017
Cited by 49 | Viewed by 7291
Abstract
The provision of pure enantiomers is of increasing importance not only for the pharmaceutical industry but also for agro-chemistry and biotechnology. In drug discovery and development, the enantiomers of a chiral drug depict unique chemical and pharmacological behaviors in a chiral environment, such [...] Read more.
The provision of pure enantiomers is of increasing importance not only for the pharmaceutical industry but also for agro-chemistry and biotechnology. In drug discovery and development, the enantiomers of a chiral drug depict unique chemical and pharmacological behaviors in a chiral environment, such as the human body, in which the stereochemistry of the chiral drugs determines their pharmacokinetic, pharmacodynamic and toxicological properties. We present a number of challenging case studies of up-to-kilogram separations of racemic or enriched isomer mixtures using preparative liquid chromatography and super critical fluid chromatography to generate individual enantiomers that have enabled the development of new candidate drugs within AstraZeneca. The combination of chromatography and racemization as well as strategies on when to apply preparative chiral chromatography of enantiomers in a multi-step synthesis of a drug compound can further facilitate accelerated drug discovery and the early clinical evaluation of the drug candidates. Full article
(This article belongs to the Special Issue Chromatographic Separation of Enantiomers: Commemorative Issue in Honor of Professor Stig Allenmark on the Occasion of His 80th Birthday)
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