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Molecules, Volume 18, Issue 5 (May 2013), Pages 4844-6127

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Open AccessArticle The Ameliorative Effect of Sophoricoside on Mast Cell-Mediated Allergic Inflammation in Vivo and in Vitro
Molecules 2013, 18(5), 6113-6127; https://doi.org/10.3390/molecules18056113
Received: 11 March 2013 / Revised: 7 May 2013 / Accepted: 10 May 2013 / Published: 22 May 2013
Cited by 5 | PDF Full-text (1073 KB) | HTML Full-text | XML Full-text
Abstract
Sophoricoside exhibits numerous pharmacological effects, including anti- inflammatory and anti-cancer actions, yet the exact mechanism that accounts for the anti-allergic effects of sophoricoside is not completely understood. The aim of the present study was to elucidate whether and how sophoricoside modulates the mast
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Sophoricoside exhibits numerous pharmacological effects, including anti- inflammatory and anti-cancer actions, yet the exact mechanism that accounts for the anti-allergic effects of sophoricoside is not completely understood. The aim of the present study was to elucidate whether and how sophoricoside modulates the mast cell-mediated allergic inflammation in vitro and in vivo. We investigated the pharmacological effects of sophoricoside on both compound 48/80 or histamine-induced scratching behaviors and 2,4-dinitrochlorobenzene (DNCB)-induced atopic dermatitis in mice. Additionally, to find a possible explanation for the anti-inflammatory effects of sophoricoside, we evaluated the effects of sophoricoside on the production of histamine and inflammatory cytokines and activation of nuclear factor-κB (NF-κB) and caspase-1 in phorbol 12-myristate 13-acetate plus calcium ionophore A23187 (PMACI)-stimulated human mast cells (HMC-1). The finding of this study demonstrated that sophoricoside reduced compound 48/80 or histamine-induced scratching behaviors and DNCB-induced atopic dermatitis in mice. Additionally, sophoricoside inhibited the production of inflammatory cytokines as well as the activation of NF-κB and caspase-1 in stimulated HMC-1. Collectively, the findings of this study provide us with novel insights into the pharmacological actions of sophoricoside as a potential molecule for use in the treatment of allergic inflammation diseases. Full article
(This article belongs to the Special Issue Anti-Inflammatory & Anti-Allergy Agents in Medicinal Chemistry)
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Open AccessShort Note Bolaamphiphiles Derived from Alkenyl L-Rhamnosides and Alkenyl D-Xylosides: Importance of the Hydrophilic Head
Molecules 2013, 18(5), 6101-6112; https://doi.org/10.3390/molecules18056101
Received: 2 April 2013 / Revised: 22 April 2013 / Accepted: 15 May 2013 / Published: 22 May 2013
Cited by 11 | PDF Full-text (323 KB) | HTML Full-text | XML Full-text
Abstract
The two step synthesis of a new bolaamphiphile derived from alkenyl l-rhamnosides was described. The general synthetic strategy of bolaamphiphiles derived from l-rhamnose was based on a previous work describing the synthesis of bolaamphiphiles derived from d-xylose. The conformational properties of this new
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The two step synthesis of a new bolaamphiphile derived from alkenyl l-rhamnosides was described. The general synthetic strategy of bolaamphiphiles derived from l-rhamnose was based on a previous work describing the synthesis of bolaamphiphiles derived from d-xylose. The conformational properties of this new compound were investigated by FTIR spectroscopy in an aqueous film in order to obtain a reference for further studies about the membrane-interacting properties. Moreover, the surface activity of this new bolaamphiphile was analyzed by Langmuir balance technology and was compared with that of the analogous bolaamphiphile derived from alkenyl D-xylosides. The findings indicate that the rhamnoside-based bolaform has an increased surface activity and a better ability to form aggregates than xyloside-based one. Full article
(This article belongs to the Section Organic Chemistry)
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Open AccessArticle Low-Density Lipoprotein (LDL)-Antioxidant Biflavonoids from Garcinia madruno
Molecules 2013, 18(5), 6092-6100; https://doi.org/10.3390/molecules18056092
Received: 3 March 2013 / Revised: 25 April 2013 / Accepted: 10 May 2013 / Published: 22 May 2013
Cited by 15 | PDF Full-text (259 KB) | HTML Full-text | XML Full-text
Abstract
Six biflavonoids were isolated from G. madruno, one of which, 7''-O-(6''''-acetyl)-glucoside of morelloflavone, is a new compound identified on the basis of 1D, 2D NMR (HMQC and HMBC) spectroscopic methods and chemical evidence. The antioxidant activity of the biflavonoids against
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Six biflavonoids were isolated from G. madruno, one of which, 7''-O-(6''''-acetyl)-glucoside of morelloflavone, is a new compound identified on the basis of 1D, 2D NMR (HMQC and HMBC) spectroscopic methods and chemical evidence. The antioxidant activity of the biflavonoids against low-density lipoprotein (LDL) peroxidation induced with Cu2+, was studied by means of a TBARS assay. The antioxidant potential of a biflavonoid fraction (BF) was also evaluated and correlated with its biflavonoid content. The flavanone-(3→8'')-flavone biflavonoids displayed antioxidant activity, particularly morelloflavone, which was significantly more potent than quercetin, with a CE50 of 12.36 μg/mL. Lipid peroxidation, was also significantly reduced in the presence of the BF (EC50 = 11.85 μg/mL). These results suggest that the BF is an excellent antioxidant. Full article
(This article belongs to the Section Natural Products Chemistry)
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Open AccessArticle Substituted 3-Benzylcoumarins as Allosteric MEK1 Inhibitors: Design, Synthesis and Biological Evaluation as Antiviral Agents
Molecules 2013, 18(5), 6057-6091; https://doi.org/10.3390/molecules18056057
Received: 25 April 2013 / Revised: 10 May 2013 / Accepted: 14 May 2013 / Published: 21 May 2013
Cited by 9 | PDF Full-text (1413 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
In order to find novel antiviral agents, a series of allosteric MEK1 inhibitors were designed and synthesized. Based on docking results, multiple optimizations were made on the coumarin scaffold. Some of the derivatives showed excellent MEK1 binding affinity in the appropriate enzymatic assays
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In order to find novel antiviral agents, a series of allosteric MEK1 inhibitors were designed and synthesized. Based on docking results, multiple optimizations were made on the coumarin scaffold. Some of the derivatives showed excellent MEK1 binding affinity in the appropriate enzymatic assays and displayed obvious inhibitory effects on the ERK pathway in a cellular assay. These compounds also significantly inhibited virus (EV71) replication in HEK293 and RD cells. Several compounds showed potential as agents for the treatment of viral infective diseases, with the most potent compound 18 showing an IC50 value of 54.57 nM in the MEK1 binding assay. Full article
(This article belongs to the Section Medicinal Chemistry)
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Open AccessArticle Impact of Fruit Piece Structure in Yogurts on the Dynamics of Aroma Release and Sensory Perception
Molecules 2013, 18(5), 6035-6056; https://doi.org/10.3390/molecules18056035
Received: 22 February 2013 / Revised: 2 May 2013 / Accepted: 15 May 2013 / Published: 21 May 2013
Cited by 10 | PDF Full-text (809 KB) | HTML Full-text | XML Full-text
Abstract
The aim of this work was to gain insight into the effect of food formulation on aroma release and perception, both of which playing an important role in food appreciation. The quality and quantity of retronasal aroma released during food consumption affect the
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The aim of this work was to gain insight into the effect of food formulation on aroma release and perception, both of which playing an important role in food appreciation. The quality and quantity of retronasal aroma released during food consumption affect the exposure time of olfactory receptors to aroma stimuli, which can influence nutritional and hedonic characteristics, as well as consumption behaviors. In yogurts, fruit preparation formulation can be a key factor to modulate aroma stimulation. In this context, the impact of size and hardness of fruit pieces in fat-free pear yogurts was studied. Proton Transfer Reaction-Mass Spectrometry (PTR-MS) was used to allow sensitive and on-line monitoring of volatile odorous compound release in the breath during consumption. In parallel, a trained panel used sensory profile and Temporal Dominance of Sensations (TDS) methods to characterize yogurt sensory properties and their dynamic changes during consumption. Results showed that the size of pear pieces had few effects on aroma release and perception of yogurts, whereas fruit hardness significantly influenced them. Despite the fact that yogurts presented short and similar residence times in the mouth, this study showed that fruit preparation could be an interesting formulation factor to enhance exposure time to stimuli and thus modify food consumption behaviors. These results could be taken into account to formulate new products that integrate both nutritional and sensory criteria. Full article
(This article belongs to the Special Issue Flavors and Fragrances)
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Open AccessArticle An Efficient Synthesis of Aldohexose-Derived Piperidine Nitrones: Precursors of Piperidine Iminosugars
Molecules 2013, 18(5), 6021-6034; https://doi.org/10.3390/molecules18056021
Received: 7 May 2013 / Revised: 15 May 2013 / Accepted: 17 May 2013 / Published: 21 May 2013
Cited by 2 | PDF Full-text (251 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
D-Glucopyranose-derived and L-idopyranose-derived piperidine nitrones were synthesized in good overall yields through six-step reaction sequence starting from readily available 2,3,4,6-tetra-O-benzyl-D-glucopyranose. The method is efficient and could be general for the synthesis of aldohexose-derived piperidine nitrones which are precursors of piperidine iminosugars. Full article
(This article belongs to the Section Organic Chemistry)
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Open AccessArticle Different Analytical Approaches in Assessing Antibacterial Activity and the Purity of Commercial Lysozyme Preparations for Dairy Application
Molecules 2013, 18(5), 6008-6020; https://doi.org/10.3390/molecules18056008
Received: 9 April 2013 / Revised: 16 May 2013 / Accepted: 16 May 2013 / Published: 21 May 2013
Cited by 12 | PDF Full-text (418 KB) | HTML Full-text | XML Full-text
Abstract
Hen egg-white lysozyme (LSZ) is currently used in the food industry to limit the proliferation of lactic acid bacteria spoilage in the production of wine and beer, and to inhibit butyric acid fermentation in hard and extra hard cheeses (late blowing) caused by
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Hen egg-white lysozyme (LSZ) is currently used in the food industry to limit the proliferation of lactic acid bacteria spoilage in the production of wine and beer, and to inhibit butyric acid fermentation in hard and extra hard cheeses (late blowing) caused by the outgrowth of clostridial spores. The aim of this work was to evaluate how the enzyme activity in commercial preparations correlates to the enzyme concentration and can be affected by the presence of process-related impurities. Different analytical approaches, including turbidimetric assay, SDS-PAGE and HPLC were used to analyse 17 commercial preparations of LSZ marketed in different countries. The HPLC method adopted by ISO allowed the true LSZ concentration to be determined with accuracy. The turbidimetric assay was the most suitable method to evaluate LSZ activity, whereas SDS-PAGE allowed the presence of other egg proteins, which are potential allergens, to be detected. The analytical results showed that the purity of commercially available enzyme preparations can vary significantly, and evidenced the effectiveness of combining different analytical approaches in this type of control. Full article
(This article belongs to the Section Natural Products Chemistry)
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Open AccessArticle Anionic Calixarene-Capped Silver Nanoparticles Show Species-Dependent Binding to Serum Albumins
Molecules 2013, 18(5), 5993-6007; https://doi.org/10.3390/molecules18055993
Received: 28 February 2013 / Revised: 25 April 2013 / Accepted: 9 May 2013 / Published: 21 May 2013
Cited by 5 | PDF Full-text (752 KB) | HTML Full-text | XML Full-text
Abstract
The anionic calixarenes para-sulphonatocalix[4]arene and 1,3-di-Ophosphonatocalix[ 4]arene, have been used to cap silver nanoparticles. The binding of these functional particles with regard to various serum albumins (bovine serum albumin, human serum albumin, porcine serum albumin and sheep serum albumin) has been studied by
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The anionic calixarenes para-sulphonatocalix[4]arene and 1,3-di-Ophosphonatocalix[ 4]arene, have been used to cap silver nanoparticles. The binding of these functional particles with regard to various serum albumins (bovine serum albumin, human serum albumin, porcine serum albumin and sheep serum albumin) has been studied by variable temperature fluorescence spectroscopy. The quenching of the fluorescence of the proteins was shown to vary as a function of the anionic calixarene capping molecule and also as a function of the origin of the serum albumin. It is thus possible to discriminate between the different species. Full article
(This article belongs to the Special Issue Calixarenes and Resorcinarenes)
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Open AccessArticle Synthesis of Micheliolide Derivatives and Their Activities against AML Progenitor Cells
Molecules 2013, 18(5), 5980-5992; https://doi.org/10.3390/molecules18055980
Received: 27 April 2013 / Revised: 15 May 2013 / Accepted: 16 May 2013 / Published: 21 May 2013
Cited by 7 | PDF Full-text (268 KB) | HTML Full-text | XML Full-text
Abstract
Micheliolide (MCL) derivatives with etherification or esterification of the hydroxyl group at the C4 position were synthesized and evaluated for their activities against different acute myelogenous leukemia (AML) cell lines. These derivatives demonstrated comparable activities against AML cell lines HL-60 and doxorubicin resistant
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Micheliolide (MCL) derivatives with etherification or esterification of the hydroxyl group at the C4 position were synthesized and evaluated for their activities against different acute myelogenous leukemia (AML) cell lines. These derivatives demonstrated comparable activities against AML cell lines HL-60 and doxorubicin resistant cell line HL-60/A. As to multi-drug resistant AML progenitor cells KG-1a, MCL and some of its derivatives maintained significant activities, and only 1.1–2.7 fold activity reductions were observed when compared with the activities against HL-60, while doxorubicin showed 20-fold activity reduction. Our study demonstrated that the C4 hydroxyl group of MCL might not only be a suitable position for structural modifications, but also be a starting point for the design of appropriate molecular probes to explore the specific targets in the progenitor cell line KG-1a. Full article
(This article belongs to the Section Medicinal Chemistry)
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Open AccessArticle Interactive Effect of Salicylic Acid on Some Physiological Features and Antioxidant Enzymes Activity in Ginger (Zingiber officinale Roscoe)
Molecules 2013, 18(5), 5965-5979; https://doi.org/10.3390/molecules18055965
Received: 3 April 2013 / Revised: 13 May 2013 / Accepted: 13 May 2013 / Published: 21 May 2013
Cited by 16 | PDF Full-text (421 KB) | HTML Full-text | XML Full-text
Abstract
The effect of foliar salicylic acid (SA) applications (10−3 and 10−5 M) on activities of nitrate reductase, guaiacol peroxidase (POD), superoxide dismutases (SOD), catalase (CAT) and proline enzymes and physiological parameters was evaluated in two ginger varieties (Halia Bentong and Halia
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The effect of foliar salicylic acid (SA) applications (10−3 and 10−5 M) on activities of nitrate reductase, guaiacol peroxidase (POD), superoxide dismutases (SOD), catalase (CAT) and proline enzymes and physiological parameters was evaluated in two ginger varieties (Halia Bentong and Halia Bara) under greenhouse conditions. In both varieties, tested treatments generally enhanced photosynthetic rate and total dry weight. Photosynthetic rate increases were generally accompanied by increased or unchanged stomatal conductance levels, although intercellular CO2 concentrations of treated plants were typically lower than in controls. Lower SA concentrations were generally more effective in enhancing photosynthetic rate and plant growth. Exogenous application of SA increased antioxidant enzyme activities and proline content; the greatest responses were obtained in plants sprayed with 10–5 M SA, with significant increases observed in CAT (20.1%), POD (45.2%), SOD (44.1%) and proline (43.1%) activities. Increased CAT activity in leaves is naturally expected to increase photosynthetic efficiency and thus net photosynthesis by maintaining a constant CO2 supply. Our results support the idea that low SA concentrations (10–5 M) may induce nitrite reductase synthesis by mobilizing intracellular NO3 and can provide protection to nitrite reductase degradation in vivo in the absence of NO3–. Observed positive correlations among proline, SOD, CAT and POD activities in the studied varieties suggest that increased SOD activity was accompanied by increases in CAT and POD activities because of the high demands of H2O2 quenching. Full article
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Open AccessArticle Green Biosynthesis and Characterization of Magnetic Iron Oxide (Fe3O4) Nanoparticles Using Seaweed (Sargassum muticum) Aqueous Extract
Molecules 2013, 18(5), 5954-5964; https://doi.org/10.3390/molecules18055954
Received: 8 April 2013 / Revised: 14 May 2013 / Accepted: 15 May 2013 / Published: 21 May 2013
Cited by 107 | PDF Full-text (576 KB) | HTML Full-text | XML Full-text
Abstract
The synthesis of nanoparticles has become a matter of great interest in recent times due to their various advantageous properties and applications in a variety of fields. The exploitation of different plant materials for the biosynthesis of nanoparticles is considered a green technology
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The synthesis of nanoparticles has become a matter of great interest in recent times due to their various advantageous properties and applications in a variety of fields. The exploitation of different plant materials for the biosynthesis of nanoparticles is considered a green technology because it does not involve any harmful chemicals. In this study, iron oxide nanoparticles (Fe3O4-NPs) were synthesized using a rapid, single step and completely green biosynthetic method by reduction of ferric chloride solution with brown seaweed (BS, Sargassum muticum) water extract containing sulphated polysaccharides as a main factor which acts as reducing agent and efficient stabilizer. The structural and properties of the Fe3O4-NPs were investigated by X-ray diffraction, Fourier transform infrared spectroscopy, field emission scanning electron microscopy (FESEM), energy dispersive X-ray fluorescence spectrometry (EDXRF), vibrating sample magnetometry (VSM) and transmission electron microscopy. The average particle diameter as determined by TEM was found to be 18 ± 4 nm. X-ray diffraction showed that the nanoparticles are crystalline in nature, with a cubic shape. The nanoparticles synthesized through this biosynthesis method can potentially useful in various applications. Full article
(This article belongs to the Special Issue Nano-catalysts and Nano-technologies for Green Organic Synthesis)
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Open AccessArticle Dimeric Labdane Diterpenes: Synthesis and Antiproliferative Effects
Molecules 2013, 18(5), 5936-5953; https://doi.org/10.3390/molecules18055936
Received: 15 April 2013 / Revised: 29 April 2013 / Accepted: 13 May 2013 / Published: 21 May 2013
Cited by 14 | PDF Full-text (241 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Several diterpenes with the labdane skeleton show biological activity, including antiproliferative effects. Most of the research work on bioactive labdanes has been carried out on naturally occurring diterpenes and semisynthetic derivatives, but much less is known on the effects of diterpene dimers. The
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Several diterpenes with the labdane skeleton show biological activity, including antiproliferative effects. Most of the research work on bioactive labdanes has been carried out on naturally occurring diterpenes and semisynthetic derivatives, but much less is known on the effects of diterpene dimers. The aim of the present work was to synthesize dimeric diterpenes from the labdane imbricatolic acid using esters, ethers and the triazole ring as linkers. Some 18 new derivatives were prepared and the compounds were evaluated for antiproliferative activity on human normal fibroblasts (MRC-5) and the following human tumor cell lines: AGS, SK-MES-1, J82 and HL-60. The diethers 8–10, differing in the number of CH2 units in the linker, presented better antiproliferative activity with a maximum effect for the derivative 9. The best antiproliferative effect against HL-60 cells was found for compounds 3 and 17, with IC50 values of 22.3 and 23.2 μM, lower than that found for the reference compound etoposide (2.23 μM). The compounds 9, 17 and 11 were the most active derivatives towards AGS cells with IC50 values of 17.8, 23.4 and 26.1 μM. A free carboxylic acid function seems relevant for the effect as several of the compounds showed less antiproliferative effect after methylation. Full article
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Open AccessReview Metabolites from Alternaria Fungi and Their Bioactivities
Molecules 2013, 18(5), 5891-5935; https://doi.org/10.3390/molecules18055891
Received: 18 March 2013 / Revised: 6 May 2013 / Accepted: 16 May 2013 / Published: 21 May 2013
Cited by 56 | PDF Full-text (362 KB) | HTML Full-text | XML Full-text
Abstract
Alternaria is a cosmopolitan fungal genus widely distributing in soil and organic matter. It includes saprophytic, endophytic and pathogenic species. At least 268 metabolites from Alternaria fungi have been reported in the past few decades. They mainly include nitrogen-containing metabolites, steroids, terpenoids, pyranones,
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Alternaria is a cosmopolitan fungal genus widely distributing in soil and organic matter. It includes saprophytic, endophytic and pathogenic species. At least 268 metabolites from Alternaria fungi have been reported in the past few decades. They mainly include nitrogen-containing metabolites, steroids, terpenoids, pyranones, quinones, and phenolics. This review aims to briefly summarize the structurally different metabolites produced by Alternaria fungi, as well as their occurrences, biological activities and functions. Some considerations related to synthesis, biosynthesis, production and applications of the metabolites from Alternaria fungi are also discussed. Full article
(This article belongs to the Section Natural Products Chemistry)
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Open AccessReview Gold Nanoparticle Contrast Agents in Advanced X-ray Imaging Technologies
Molecules 2013, 18(5), 5858-5890; https://doi.org/10.3390/molecules18055858
Received: 12 March 2013 / Revised: 30 April 2013 / Accepted: 14 May 2013 / Published: 17 May 2013
Cited by 34 | PDF Full-text (6320 KB) | HTML Full-text | XML Full-text
Abstract
Recently, there has been significant progress in the field of soft- and hard-X-ray imaging for a wide range of applications, both technically and scientifically, via developments in sources, optics and imaging methodologies. While one community is pursuing extensive applications of available X-ray tools,
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Recently, there has been significant progress in the field of soft- and hard-X-ray imaging for a wide range of applications, both technically and scientifically, via developments in sources, optics and imaging methodologies. While one community is pursuing extensive applications of available X-ray tools, others are investigating improvements in techniques, including new optics, higher spatial resolutions and brighter compact sources. For increased image quality and more exquisite investigation on characteristic biological phenomena, contrast agents have been employed extensively in imaging technologies. Heavy metal nanoparticles are excellent absorbers of X-rays and can offer excellent improvements in medical diagnosis and X-ray imaging. In this context, the role of gold (Au) is important for advanced X-ray imaging applications. Au has a long-history in a wide range of medical applications and exhibits characteristic interactions with X-rays. Therefore, Au can offer a particular advantage as a tracer and a contrast enhancer in X-ray imaging technologies by sensing the variation in X-ray attenuation in a given sample volume. This review summarizes basic understanding on X-ray imaging from device set-up to technologies. Then this review covers recent studies in the development of X-ray imaging techniques utilizing gold nanoparticles (AuNPs) and their relevant applications, including two- and three-dimensional biological imaging, dynamical processes in a living system, single cell-based imaging and quantitative analysis of circulatory systems and so on. In addition to conventional medical applications, various novel research areas have been developed and are expected to be further developed through AuNP-based X-ray imaging technologies. Full article
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Open AccessReview Vasodilator Compounds Derived from Plants and Their Mechanisms of Action
Molecules 2013, 18(5), 5814-5857; https://doi.org/10.3390/molecules18055814
Received: 19 April 2013 / Revised: 24 April 2013 / Accepted: 7 May 2013 / Published: 17 May 2013
Cited by 15 | PDF Full-text (373 KB) | HTML Full-text | XML Full-text
Abstract
The present paper reviews vasodilator compounds isolated from plants that were reported in the past 22 years (1990 to 2012) and the different mechanisms of action involved in their vasodilator effects. The search for reports was conducted in a comprehensive manner, intending to
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The present paper reviews vasodilator compounds isolated from plants that were reported in the past 22 years (1990 to 2012) and the different mechanisms of action involved in their vasodilator effects. The search for reports was conducted in a comprehensive manner, intending to encompass those metabolites with a vasodilator effect whose mechanism of action involved both vascular endothelium and arterial smooth muscle. The results obtained from our bibliographic search showed that over half of the isolated compounds have a mechanism of action involving the endothelium. Most of these bioactive metabolites cause vasodilation either by activating the nitric oxide/cGMP pathway or by blocking voltage-dependent calcium channels. Moreover, it was found that many compounds induced vasodilation by more than one mechanism. This review confirms that secondary metabolites, which include a significant group of compounds with extensive chemical diversity, are a valuable source of new pharmaceuticals useful for the treatment and prevention of cardiovascular diseases. Full article
(This article belongs to the Special Issue Bioassay-Guided Isolation of Natural Products)
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