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Molecules, Volume 15, Issue 12 (December 2010), Pages 8534-9495

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Open AccessArticle Antiproliferative Activity, Antioxidant Capacity and Tannin Content in Plants of Semi-Arid Northeastern Brazil  
Molecules 2010, 15(12), 8534-8542; doi:10.3390/molecules15128534
Received: 29 October 2010 / Accepted: 22 November 2010 / Published: 24 November 2010
Cited by 38 | PDF Full-text (122 KB)
Abstract
The objective of this study was to evaluate antiproliferative activity, antioxidant capacity and tannin content in plants from semi-arid northeastern Brazil (Caatinga). For this study, we selected 14 species and we assayed the methanol extracts for antiproliferative activity against the HEp-2 (laryngeal cancer)
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The objective of this study was to evaluate antiproliferative activity, antioxidant capacity and tannin content in plants from semi-arid northeastern Brazil (Caatinga). For this study, we selected 14 species and we assayed the methanol extracts for antiproliferative activity against the HEp-2 (laryngeal cancer) and NCI-H292 (lung cancer) cell lines using the (3-[4,5-dimethylthiazol-2-yl]-2,5-diphenyltetrazole) (MTT) method. In addition, the antioxidant activity was evaluated with the DPPH (2,2-diphenyl-2-picrylhydrazyl) assay, and the tannin content was determined by the radial diffusion method. Plants with better antioxidant activity (expressed in a dose able to decrease the initial DPPH concentration by 50%, or IC50) and with higher levels of tannins were: Poincianella pyramidalis (42.95 ± 1.77 µg/mL IC50 and 8.17 ± 0.64 tannin content), Jatropha mollissima (54.09 ± 4.36µg/mL IC50 and 2.35 ± 0.08 tannin content) and Anadenanthera colubrina (73.24 ± 1.47 µg/mL IC50 and 4.41 ± 0.47 tannin content). Plants with enhanced antiproliferative activity (% living cells) were Annona muricata (24.94 ± 0.74 in NCI-H292), Lantana camara (25.8 ± 0.19 in NCI-H292), Handroanthus impetiginosus (41.8 ± 0.47 in NCI-H292) and Mentzelia aspera (45.61 ± 1.94 in HEp-2). For species with better antioxidant and antiproliferative activities, we suggest future in vitro and in vivo comparative studies with other pharmacological models, and to start a process of purification and identification of the possible molecule(s) responsible for the observed pharmacological activity. We believe that the flora of Brazilian semi-arid areas can be a valuable source of plants rich in tannins, cytotoxic compounds and antioxidant agents. Full article
(This article belongs to the Special Issue Antioxidants)
Open AccessArticle Characterization and Quantification of Polyphenols in Amazon Grape (Pourouma cecropiifolia Martius)
Molecules 2010, 15(12), 8543-8552; doi:10.3390/molecules15128543
Received: 26 October 2010 / Revised: 18 November 2010 / Accepted: 23 November 2010 / Published: 26 November 2010
Cited by 11 | PDF Full-text (121 KB)
Abstract
The phenolic profile of Amazon grape fruit (Pourouma cecropiifolia Martius) was investigated by high-performance liquid chromatography-electrospray ionization mass spectrometry (HPLC-ESI-MS/MS). For this purpose, suitable extraction and liquid chromatographic methods were developed. Anthocyanins, flavonols and chlorogenic acids were found mainly in the peel.
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The phenolic profile of Amazon grape fruit (Pourouma cecropiifolia Martius) was investigated by high-performance liquid chromatography-electrospray ionization mass spectrometry (HPLC-ESI-MS/MS). For this purpose, suitable extraction and liquid chromatographic methods were developed. Anthocyanins, flavonols and chlorogenic acids were found mainly in the peel. Besides the main anthocyanins, i.e. delphinidin 3-glucoside, cyanidin 3-glucoside and cyanidin 3-(6”-malonyl)glucoside, several minor anthocyanins were identified in the peel. Among these, cyanidin 3,5-diglucoside, delphinidin 3-galactoside, cyanidin 3-rutinoside, cyanidin 3-(3”-malonyl)glucoside, malvidin 3-glucoside, pelargonidin 3-glucoside, peonidin 3-glucoside and petunidin 3-glucoside were characterized on the basis of their fragmentation patterns in MS/MS experiments. The total anthocyanin content in the peel was 420.26 ± 3.07 mg kg-1 fresh weight. The pulp contained mainly 5-O-caffeoylquinic acid (210.39 ± 3.43 mg kg-1 fresh weight). Rutin was the predominant flavonol found in Amazon grape (peel 155.45 ± 2.06 mg kg-1 fresh weight and pulp 2.64 ± 1.21 mg kg-1 fresh weight). Total polyphenols content was higher in the peel than in the pulp. Full article
(This article belongs to the Section Natural Products)
Open AccessArticle Anticariogenic Properties of ent-Pimarane Diterpenes Obtained by Microbial Transformation
Molecules 2010, 15(12), 8553-8566; doi:10.3390/molecules15128553
Received: 28 October 2010 / Revised: 12 November 2010 / Accepted: 16 November 2010 / Published: 25 November 2010
Cited by 12 | PDF Full-text (135 KB)
Abstract
In the present work, the anticariogenic activities of three pimarane-type diterpenes obtained by fungal biotransformation were investigated. Among these metabolites, ent-8(14),15-pimaradien-19-ol was the most active compound, displaying very promising MIC values (ranging from 1.5 to 4.0 μg mL-1) against the
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In the present work, the anticariogenic activities of three pimarane-type diterpenes obtained by fungal biotransformation were investigated. Among these metabolites, ent-8(14),15-pimaradien-19-ol was the most active compound, displaying very promising MIC values (ranging from 1.5 to 4.0 μg mL-1) against the main microorganisms responsible for dental caries: Streptococcus salivarius, S. sobrinus, S. mutans, S. mitis, S. sanguinis, and Lactobacillus casei. Time kill assays performed with ent-8(14),15-pimaradien-19-ol against the primary causative agent S. mutans revealed that this compound only avoids growth of the inoculum in the first 12 h (bacteriostatic effect). However, its bactericidal effect is clearly noted thereafter (between 12 and 24 h). The curve profile obtained by combining ent-8(14),15-pimaradien-19-ol and chlorhexidine revealed a significant reduction in the time necessary for killing S. mutans compared with each of these two chemicals alone. However, no synergistic effect was observed using the same combination in the checkerboard assays against this microorganism. In conclusion, our results point out that ent-8(14),15-pimaradien-19-ol is an important metabolite in the search for new effective anticariogenic agents. Full article
(This article belongs to the Section Natural Products)
Open AccessArticle Synthesis, Antimycobacterial, Antifungal and Photosynthesis-Inhibiting Activity of Chlorinated N-phenylpyrazine-2-carboxamides
Molecules 2010, 15(12), 8567-8581; doi:10.3390/molecules15128567
Received: 15 November 2010 / Revised: 22 November 2010 / Accepted: 25 November 2010 / Published: 26 November 2010
Cited by 21 | PDF Full-text (277 KB)
Abstract
A series of sixteen pyrazinamide analogues with the -CONH- linker connecting the pyrazine and benzene rings was synthesized by the condensation of chlorides of substituted pyrazinecarboxylic acids with ring-substituted (chlorine) anilines. The prepared compounds were characterized and evaluated for their antimycobacterial and antifungal
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A series of sixteen pyrazinamide analogues with the -CONH- linker connecting the pyrazine and benzene rings was synthesized by the condensation of chlorides of substituted pyrazinecarboxylic acids with ring-substituted (chlorine) anilines. The prepared compounds were characterized and evaluated for their antimycobacterial and antifungal activity, and for their ability to inhibit photosynthetic electron transport (PET). 6-Chloro-N-(4-chlorophenyl)pyrazine-2-carboxamide manifested the highest activity against Mycobacterium tuberculosis strain H37Rv (65% inhibition at 6.25 μg/mL). The highest antifungal effect against Trichophyton mentagrophytes, the most susceptible fungal strain tested, was found for 6-chloro-5-tert-butyl-N-(3,4-dichlorophenyl)pyrazine-2-carboxamide (MIC = 62.5 μmol/L). 6-Chloro-5-tert-butyl-N-(4-chlorophenyl)pyrazine-2-carboxamide showed the highest PET inhibition in spinach chloroplasts (Spinacia oleracea L.) chloroplasts (IC50 = 43.0 μmol/L). For all the compounds, the relationships between the lipophilicity and the chemical structure of the studied compounds as well as their structure-activity relationships are discussed. Full article
(This article belongs to the Special Issue ECSOC-12)
Open AccessCommunication Synthesis of New C2- Symmetric Fluoren-9-ylidene Malonate Derived Bis(oxazoline) Ligands and Their Application in Friedel-Crafts Reactions
Molecules 2010, 15(12), 8582-8592; doi:10.3390/molecules15128582
Received: 10 November 2010 / Revised: 18 November 2010 / Accepted: 23 November 2010 / Published: 26 November 2010
PDF Full-text (177 KB)
Abstract
A series of new C2-symmetric fluoren-9-ylidene malonate-derived bis(oxazoline) ligands were synthesized from fluoren-9-ylidene malonate and enantiomerically pure amino alcohols via a convenient route. Their asymmetric catalytic properties in the Friedel-Crafts reactions of indoles with arylidene malonates were evaluated, and the Cu(OTf)
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A series of new C2-symmetric fluoren-9-ylidene malonate-derived bis(oxazoline) ligands were synthesized from fluoren-9-ylidene malonate and enantiomerically pure amino alcohols via a convenient route. Their asymmetric catalytic properties in the Friedel-Crafts reactions of indoles with arylidene malonates were evaluated, and the Cu(OTf)2 complex of a fluoren-9-ylidene malonate-derived bis(oxazoline) bearing a phenyl group showed moderate to good enantioselectivity (up to 88% ee). Full article
Open AccessArticle Synthesis of Benzofuran Derivatives via Rearrangement and Their Inhibitory Activity on Acetylcholinesterase
Molecules 2010, 15(12), 8593-8601; doi:10.3390/molecules15128593
Received: 15 September 2010 / Revised: 18 November 2010 / Accepted: 24 November 2010 / Published: 29 November 2010
Cited by 2 | PDF Full-text (176 KB)
Abstract
During a synthesis of coumarins to obtain new candidates for treating Alzheimer’s Disease (AD), an unusual rearrangement of a benzopyran group to a benzofuran group occurred, offering a novel synthesis pathway of these benzofuran derivatives. The possible mechanism of the novel rearrangement was
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During a synthesis of coumarins to obtain new candidates for treating Alzheimer’s Disease (AD), an unusual rearrangement of a benzopyran group to a benzofuran group occurred, offering a novel synthesis pathway of these benzofuran derivatives. The possible mechanism of the novel rearrangement was also discussed. All of the benzofuran derivatives have weak anti-AChE activities compared with the reference compound, donepezil. Full article
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Open AccessArticle Antioxidant Capacities and Total Phenolic Contents of 56 Wild Fruits from South China
Molecules 2010, 15(12), 8602-8617; doi:10.3390/molecules15128602
Received: 8 October 2010 / Revised: 17 November 2010 / Accepted: 24 November 2010 / Published: 29 November 2010
Cited by 40 | PDF Full-text (162 KB)
Abstract
In order to identify wild fruits possessing high nutraceutical potential, the antioxidant activities of 56 wild fruits from South China were systematically evaluated. The fat-soluble components were extracted with tetrahydrofuran, and the water-soluble ones were extracted with a 50:3.7:46.3 (v/v) methanol-acetic acid-water mixture.
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In order to identify wild fruits possessing high nutraceutical potential, the antioxidant activities of 56 wild fruits from South China were systematically evaluated. The fat-soluble components were extracted with tetrahydrofuran, and the water-soluble ones were extracted with a 50:3.7:46.3 (v/v) methanol-acetic acid-water mixture. The antioxidant capacities of the extracts were evaluated using the ferric reducing antioxidant power (FRAP) and Trolox equivalent antioxidant capacity (TEAC) assays, and their total phenolic contents were measured by the Folin-Ciocalteu method. Most of these wild fruits were analyzed for the first time for their antioxidant activities. Generally, these fruits had high antioxidant capacities and total phenolic contents. A significant correlation between the FRAP value and the TEAC value suggested that antioxidant components in these wild fruits were capable of reducing oxidants and scavenging free radicals. A high correlation between antioxidant capacity and total phenolic content indicated that phenolic compounds could be the main contributors to the measured antioxidant activity. The results showed that fruits of Eucalyptus robusta, Eurya nitida, Melastoma sanguineum, Melaleuca leucadendron, Lagerstroemia indica, Caryota mitis, Lagerstroemia speciosa and Gordonia axillaris possessed the highest antioxidant capacities and total phenolic contents among those tested, and could be potential rich sources of natural antioxidants and functional foods. The results obtained are very helpful for the full utilization of these wild fruits. Full article
(This article belongs to the Special Issue Phenolics and Polyphenolics)
Open AccessArticle Fully Automated Spectrometric Protocols for Determination of Antioxidant Activity: Advantages and Disadvantages
Molecules 2010, 15(12), 8618-8640; doi:10.3390/molecules15128618
Received: 19 October 2010 / Revised: 22 November 2010 / Accepted: 26 November 2010 / Published: 29 November 2010
Cited by 47 | PDF Full-text (437 KB)
Abstract
The aim of this study was to describe behaviour, kinetics, time courses and limitations of the six different fully automated spectrometric methods - DPPH, TEAC, FRAP, DMPD, Free Radicals and Blue CrO5. Absorption curves were measured and absorbance maxima were found.
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The aim of this study was to describe behaviour, kinetics, time courses and limitations of the six different fully automated spectrometric methods - DPPH, TEAC, FRAP, DMPD, Free Radicals and Blue CrO5. Absorption curves were measured and absorbance maxima were found. All methods were calibrated using the standard compounds Trolox® and/or gallic acid. Calibration curves were determined (relative standard deviation was within the range from 1.5 to 2.5 %). The obtained characteristics were compared and discussed. Moreover, the data obtained were applied to optimize and to automate all mentioned protocols. Automatic analyzer allowed us to analyse simultaneously larger set of samples, to decrease the measurement time, to eliminate the errors and to provide data of higher quality in comparison to manual analysis. The total time of analysis for one sample was decreased to 10 min for all six methods. In contrary, the total time of manual spectrometric determination was approximately 120 min. The obtained data provided good correlations between studied methods (R = 0.97 – 0.99). Full article
(This article belongs to the Special Issue Antioxidants)
Open AccessArticle Concise Syntheses of Trifluoromethylated Cyclic and Acyclic Analogues of cADPR
Molecules 2010, 15(12), 8689-8701; doi:10.3390/molecules15128689
Received: 6 November 2010 / Revised: 17 November 2010 / Accepted: 22 November 2010 / Published: 30 November 2010
Cited by 9 | PDF Full-text (225 KB)
Abstract
A novel trifluoromethylated analogue of cADPR, 8-CF3-cIDPDE (5) was designed and synthesized via construction of N1,N9-disubstituted hypoxanthine, trifluoromethylation and intramolecular condensation. A series of acyclic analogues of cADPR were also designed and synthesized. These compounds
[...] Read more.
A novel trifluoromethylated analogue of cADPR, 8-CF3-cIDPDE (5) was designed and synthesized via construction of N1,N9-disubstituted hypoxanthine, trifluoromethylation and intramolecular condensation. A series of acyclic analogues of cADPR were also designed and synthesized. These compounds could be useful molecules for studying the structure-activity relationship of cADPR analogues and exploring the cADPR/RyR Ca2+ signalling system. Full article
Open AccessArticle Platycoside N: A New Oleanane-Type Triterpenoid Saponin from the Roots of Platycodon grandiflorum
Molecules 2010, 15(12), 8702-8708; doi:10.3390/molecules15128702
Received: 13 September 2010 / Revised: 22 November 2010 / Accepted: 25 November 2010 / Published: 30 November 2010
Cited by 12 | PDF Full-text (185 KB)
Abstract
A new oleanane-type triterpenoid saponin, named platycoside N (1), together with six known saponins, was isolated from the roots of Platycodon grandiflorum. On the basis of acid hydrolysis, comprehensive spectroscopic data analyses and comparison with the spectral data of the known compounds,
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A new oleanane-type triterpenoid saponin, named platycoside N (1), together with six known saponins, was isolated from the roots of Platycodon grandiflorum. On the basis of acid hydrolysis, comprehensive spectroscopic data analyses and comparison with the spectral data of the known compounds, its structure was elucidated as 3-O-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl-2β,3β,16α,23-tetrahydroxyolean-12-en-28-oic acid 28-O-β-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranoside. The six known compounds were platycodin D (2), deapioplatycodin D (3), platycodin D3 (4), deapio- platycodin D3 (5), platycoside E (6) and deapioplatycoside E (7). Full article
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Open AccessArticle Computational Aspects of Carbon and Boron Nanotubes
Molecules 2010, 15(12), 8709-8722; doi:10.3390/molecules15128709
Received: 19 September 2010 / Revised: 16 November 2010 / Accepted: 17 November 2010 / Published: 30 November 2010
Cited by 7 | PDF Full-text (574 KB)
Abstract
Carbon hexagonal nanotubes, boron triangular nanotubes and boron a-nanotubes are a few popular nano structures. Computational researchers look at these structures as graphs where each atom is a node and an atomic bond is an edge. While researchers are discussing the differences among
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Carbon hexagonal nanotubes, boron triangular nanotubes and boron a-nanotubes are a few popular nano structures. Computational researchers look at these structures as graphs where each atom is a node and an atomic bond is an edge. While researchers are discussing the differences among the three nanotubes, we identify the topological and structural similarities among them. We show that the three nanotubes have the same maximum independent set and their matching ratios are independent of the number of columns. In addition, we illustrate that they also have similar underlying broadcasting spanning tree and identical communication behavior. Full article
(This article belongs to the Special Issue From Computational Chemistry to Complex Networks)
Open AccessArticle Synthesis and Biological Evaluation of Pyrazolo[1,5-a]-pyrimidine-containing 99mTc Nitrido Radiopharmaceuticals as Imaging Agents for Tumors
Molecules 2010, 15(12), 8723-8733; doi:10.3390/molecules15128723
Received: 1 November 2010 / Revised: 15 November 2010 / Accepted: 24 November 2010 / Published: 30 November 2010
Cited by 6 | PDF Full-text (223 KB)
Abstract
The compound 5-((2-aminoethylamino)methyl)-7-(4-bromoanilino)-3-cyano-pyrazolo[1,5-a]pyrimidine (ABCPP) was synthesized and conjugated with N-mercapto-acetylglycine (MAG), N-mercaptoacetylphenylalanine (MAF) and N-mercaptoacetylvaline (MAA), respectively. These three compounds were labeled successfully with [99mTcN]2+ intermediate in high radiochemical purities. Biodistribution in tumor-bearing mice demonstrated that the
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The compound 5-((2-aminoethylamino)methyl)-7-(4-bromoanilino)-3-cyano-pyrazolo[1,5-a]pyrimidine (ABCPP) was synthesized and conjugated with N-mercapto-acetylglycine (MAG), N-mercaptoacetylphenylalanine (MAF) and N-mercaptoacetylvaline (MAA), respectively. These three compounds were labeled successfully with [99mTcN]2+ intermediate in high radiochemical purities. Biodistribution in tumor-bearing mice demonstrated that the three new complexes showed tumor accumulation, high tumor-to-muscle (T/M) ratios and fast clearance from blood and muscle. Among them, the 99mTcN-MAG-ABCPP showed the most favorable characteristics, with tumor/blood and tumor/ muscle ratios reaching 1.51 and 2.97 at 30 min post-injection, 1.84 and 2.49 at 60 min post-injection, suggesting it could be further studied as potential tumor imaging agent for single photon emission computed tomography (SPECT). Full article
(This article belongs to the Section Medicinal Chemistry)
Open AccessArticle Effects of Conventional Heating on the Stability of Major Olive Oil Phenolic Compounds by Tandem Mass Spectrometry and Isotope Dilution Assay
Molecules 2010, 15(12), 8734-8746; doi:10.3390/molecules15128734
Received: 18 October 2010 / Revised: 18 November 2010 / Accepted: 26 November 2010 / Published: 1 December 2010
Cited by 10 | PDF Full-text (248 KB)
Abstract
The quality of olive oils is sensorially tested by accurate and well established methods. It enables the classification of the pressed oils into the classes of extra virgin oil, virgin oil and lampant oil. Nonetheless, it would be convenient to have analytical methods
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The quality of olive oils is sensorially tested by accurate and well established methods. It enables the classification of the pressed oils into the classes of extra virgin oil, virgin oil and lampant oil. Nonetheless, it would be convenient to have analytical methods for screening oils or supporting sensorial analysis using a reliable independent approach based on exploitation of mass spectrometric methodologies. A number of methods have been proposed to evaluate deficiencies of extra virgin olive oils resulting from inappropriate technological treatments, such as high or low temperature deodoration, and home cooking processes. The quality and nutraceutical value of extra virgin olive oil (EVOO) can be related to the antioxidant property of its phenolic compounds. Olive oil is a source of at least 30 phenolic compounds, such as oleuropein, oleocanthal, hydroxytyrosol, and tyrosol, all acting as strong antioxidants, radical scavengers and NSAI-like drugs. We now report the efficacy of MRM tandem mass spectrometry, assisted by the isotope dilution assay, in the evaluation of the thermal stability of selected active principles of extra virgin olive oil. Full article
(This article belongs to the Special Issue Phenolics and Polyphenolics)
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Open AccessArticle A Simplified Liquid Chromatography-Mass Spectrometry Assay for Artesunate and Dihydroartemisinin, Its Metabolite, in Human Plasma
Molecules 2010, 15(12), 8747-8768; doi:10.3390/molecules15128747
Received: 18 October 2010 / Revised: 13 November 2010 / Accepted: 27 November 2010 / Published: 1 December 2010
Cited by 10 | PDF Full-text (443 KB)
Abstract
Artesunate (AS) is a potent antimalarial that is used worldwide for the treatment of malaria. A simple method with a total run time of 12 min was developed and validated for the quantification of AS and dihydroartemisinin (DHA), its active metabolite, in human
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Artesunate (AS) is a potent antimalarial that is used worldwide for the treatment of malaria. A simple method with a total run time of 12 min was developed and validated for the quantification of AS and dihydroartemisinin (DHA), its active metabolite, in human (heparinized) plasma based on one-step protein precipitation in acetonitrile using artemisinin (ARN) as an internal standard, followed by liquid chromatography with a single quadrupole mass spectrometry system connected to a C18 column. Peak area ratio responses were fitted to the 2nd-order curve type, polynomial equation with weighting (1/concentration) over a quantification range between 3.20/5.33–3,000/5,000 nM (1.23/1.52–1153/1422 ng/mL) of AS/DHA showing linearity with very good correlation (r2 > 0.999). Single ion recordings of 5 µL injections of plasma extracts allowed for limits of detection of 1.02 nM (0.39 ng/mL) for AS and 0.44 nM (0.13 ng/mL) for DHA. The inter-assay and intra-assay accuracy and precision of the method was very good with an inaccuracy of ±12.4% and coefficients of variation of ≤10.7% at all tested concentrations. The recovery of the analytes from plasma was ≥95%. Other commonly used antimalarials including mefloquine, quinine, and chloroquine, did not interfere with the analysis. Post-preparative tests over 24 h in an autosampler (10 °C) showed that the DHA response was only 2.1% of AS from auto-hydrolysis, and β-DHA was the major, stable epimer that was used for quantification of DHA. In contrast, α-DHA increased steadily up to 600%. Artesunate and DHA in plasma were stable through three freeze/thaw cycles for up to 6 h at room temperature and up to one year at -80 °C. Full article
Open AccessArticle Assessment of the Content of Phenolics and Antioxidant Action of Inflorescences and Leaves of Selected Species from the Genus Sorbus Sensu Stricto
Molecules 2010, 15(12), 8769-8783; doi:10.3390/molecules15128769
Received: 5 November 2010 / Revised: 26 November 2010 / Accepted: 30 November 2010 / Published: 2 December 2010
Cited by 11 | PDF Full-text (209 KB)
Abstract
In order to find new sources of natural antioxidants, the antioxidant potential of 70% methanolic extracts from the inflorescences and leaves of 16 species from the genus Sorbus s.s. was evaluated using two complementary in vitro test systems: the DPPH (2,2-diphenyl-1-picrylhydrazyl) radical-scavenging assay
[...] Read more.
In order to find new sources of natural antioxidants, the antioxidant potential of 70% methanolic extracts from the inflorescences and leaves of 16 species from the genus Sorbus s.s. was evaluated using two complementary in vitro test systems: the DPPH (2,2-diphenyl-1-picrylhydrazyl) radical-scavenging assay and the AAPH [2,2¢-azobis-(2-amidinopropane)dihydrochloride]-induced linoleic acid (LA) peroxidation test. The radical-scavenging capacities of the extracts towards the DPPH radical were in the range of 0.25-0.86 millimolar Trolox® equivalents/g dry weight. They were significantly correlated (r = -0.8089, p < 0.001) with the results of the LA-peroxidation test, indicating the Sorbus extracts to be universal antioxidants. Significant linear correlations were also found between the different antioxidant potentials and total phenolic contents as estimated by the Folin-Ciocalteu method and further verified by serial determinations of proanthocyanidins, chlorogenic acid isomers and flavonoids (çrêin the range of 0.71-0.95, p < 0.001). Cluster analysis of the data matrix identified the ten samples (inflorescences of S. aucuparia, S. pohuashanensis, S. decora, S. koehneana, S. commixta, S. gracilis, and S. sitchensis, and the leaves of S. wilfordii, S. pogonopetala, and S. gracilis) exhibiting the highest antioxidant activity and total phenolic levels and therefore the greatest potential as effective sources for natural health products. Full article
(This article belongs to the Section Natural Products)
Open AccessArticle Synthesis of the Marine Bromotyrosine Psammaplin F and Crystal Structure of a Psammaplin A Analogue
Molecules 2010, 15(12), 8784-8795; doi:10.3390/molecules15128784
Received: 4 November 2010 / Revised: 25 November 2010 / Accepted: 29 November 2010 / Published: 2 December 2010
Cited by 11 | PDF Full-text (203 KB)
Abstract
Psammaplin F, an unsymmetrical disulfide bromotyrosine, was isolated from the sponge Pseudoceratina purpurea in 2003. We reported here the first total synthesis of psammaplin F in 12% overall yield by employing Cleland’s reagent reduction as key step. The longest linear synthetic sequence starting
[...] Read more.
Psammaplin F, an unsymmetrical disulfide bromotyrosine, was isolated from the sponge Pseudoceratina purpurea in 2003. We reported here the first total synthesis of psammaplin F in 12% overall yield by employing Cleland’s reagent reduction as key step. The longest linear synthetic sequence starting from 3-bromo-4-hydroxybenzaldehyde and hydantoin was seven steps. In addition, a detailed X-ray crystal structure analysis of psammaplin A analogue 8b is given for the first time. Full article
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Open AccessArticle Synthesis and Structure-Activity Relationships of Fenbufen Amide Analogs
Molecules 2010, 15(12), 8796-8803; doi:10.3390/molecules15128796
Received: 4 November 2010 / Revised: 29 November 2010 / Accepted: 1 December 2010 / Published: 2 December 2010
Cited by 3 | PDF Full-text (162 KB)
Abstract
The previous discoveries of butyl fenbufen amide analogs with antitumor effects were further examined. The amide analogs with 1, 3, 4 and 8 carbons chains were prepared in 70-80% yield. Fenbufen had no cytotoxic effects at concentrations ranging from 10 to 100 μM.
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The previous discoveries of butyl fenbufen amide analogs with antitumor effects were further examined. The amide analogs with 1, 3, 4 and 8 carbons chains were prepared in 70-80% yield. Fenbufen had no cytotoxic effects at concentrations ranging from 10 to 100 μM. Methyl fenbufen amide had significant cytotoxic effects at a concentration of 100 μM. As the length of the alkyl amide side chain increased, the cytotoxic effects increased, and the octyl fenbufen amide had the greatest cytotoxic effect. After treatment with 30 μM octyl fenbufen amide, nearly seventy percent of the cells lost their viability. At the concentration of 10 μM, fenbufen amide analogs did not show cytotoxicity according to the MTT assay results. The NO scavenging activities of the fenbufen amide analogs were not significantly different from those of fenbufen. Full article
Open AccessCommunication Synthesis and In Vitro Evaluation of N-(Bromobut-3-en-2-yl)-7-methoxy-1,2,3,4-tetrahydroacridin-9-amine as a Cholinesterase Inhibitor with Regard to Alzheimer's Disease Treatment
Molecules 2010, 15(12), 8804-8812; doi:10.3390/molecules15128804
Received: 4 November 2010 / Revised: 30 November 2010 / Accepted: 1 December 2010 / Published: 2 December 2010
Cited by 14 | PDF Full-text (240 KB)
Abstract
A new tacrine based cholinesterase inhibitor, N-(bromobut-3-en-2-yl)-7-methoxy-1,2,3,4-tetrahydroacridin-9-amine (1), was designed and synthesized to interact with specific regions of human acetylcholinesterase and human butyrylcholinesterase. Its inhibitory ability towards cholinesterases was determined and compared to tacrine (THA) and 9-amino-7-methoxy-1,2,3,4-tetrahydroacridine (7-MEOTA). The assessment
[...] Read more.
A new tacrine based cholinesterase inhibitor, N-(bromobut-3-en-2-yl)-7-methoxy-1,2,3,4-tetrahydroacridin-9-amine (1), was designed and synthesized to interact with specific regions of human acetylcholinesterase and human butyrylcholinesterase. Its inhibitory ability towards cholinesterases was determined and compared to tacrine (THA) and 9-amino-7-methoxy-1,2,3,4-tetrahydroacridine (7-MEOTA). The assessment of IC50 values revealed 1 as a weak inhibitor of both tested enzymes. Full article
(This article belongs to the Section Medicinal Chemistry)
Open AccessArticle Microwave Assisted Synthesis of Some New Heterocyclic Spiro-Derivatives with Potential Antimicrobial and Antioxidant Activity
Molecules 2010, 15(12), 8827-8840; doi:10.3390/molecules15128827
Received: 31 October 2010 / Revised: 17 November 2010 / Accepted: 30 November 2010 / Published: 3 December 2010
Cited by 19 | PDF Full-text (147 KB)
Abstract
Homophthalic anhydride reacts with different aromatic amines to produce N-substituted homophthalimides. Bromination of the latter produces 4,4-dibromo-homophthalimide derivatives that can be used as precursors for spiro-derivatives. The dibromo derivatives react with different binucleophilic reagents to produce several spiro-isoquinoline derivatives. Reaction of the
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Homophthalic anhydride reacts with different aromatic amines to produce N-substituted homophthalimides. Bromination of the latter produces 4,4-dibromo-homophthalimide derivatives that can be used as precursors for spiro-derivatives. The dibromo derivatives react with different binucleophilic reagents to produce several spiro-isoquinoline derivatives. Reaction of the dibromo derivatives with malononitrile produces dicyanomethylene derivatives which react with different binucleophiles to produce new spiro-derivatives. Structures of the newly synthesized compounds are proved using spectroscopic methods such as IR, 1H-NMR and 13C-NMR. The newly synthesized compounds were tested for their antimicrobial and antioxidant activities, showing weak or no antimicrobial activity. On the other hand select compounds showed promising antioxidant activities. Full article
Open AccessArticle Synthesis of 6-Amino-5-cyano-1,4-disubstituted-2(1H)-Pyrimidinones via Copper-(I)-catalyzed Alkyne-azide ‘Click Chemistry’ and Their Reactivity
Molecules 2010, 15(12), 8841-8855; doi:10.3390/molecules1512884
Received: 15 October 2010 / Revised: 25 November 2010 / Accepted: 30 November 2010 / Published: 3 December 2010
Cited by 3 | PDF Full-text (172 KB)
Abstract
In this paper we present the room temperature synthesis of a novel serie of 1,4-disubstituted-1,2,3-triazoles 4a-l by employing the (3 + 2) cycloaddition reaction of pyrimidinones containing alkyne functions with different model azides in the presence of copper sulphate and sodium ascorbate. To
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In this paper we present the room temperature synthesis of a novel serie of 1,4-disubstituted-1,2,3-triazoles 4a-l by employing the (3 + 2) cycloaddition reaction of pyrimidinones containing alkyne functions with different model azides in the presence of copper sulphate and sodium ascorbate. To obtain the final triazoles, we also synthesized the major precursors 6-amino-5-cyano-1,4-disubstituted-2(1H)-pyrimidinones 3a-r from ethyl 2,2-dicyanovinylcarbamate derivatives 2a-c and various primary aromatic amines containing an alkyne group. The triazoles were prepared in good to very good yields. Full article
Open AccessArticle Development of Designed Site-Directed Pseudopeptide-Peptido-Mimetic Immunogens as Novel Minimal Subunit-Vaccine Candidates for Malaria
Molecules 2010, 15(12), 8856-8889; doi:10.3390/molecules15128856
Received: 26 September 2010 / Accepted: 28 October 2010 / Published: 6 December 2010
Cited by 3 | PDF Full-text (1126 KB)
Abstract
Synthetic vaccines constitute the most promising tools for controlling and preventing infectious diseases. When synthetic immunogens are designed from the pathogen native sequences, these are normally poorly immunogenic and do not induce protection, as demonstrated in our research. After attempting many synthetic strategies
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Synthetic vaccines constitute the most promising tools for controlling and preventing infectious diseases. When synthetic immunogens are designed from the pathogen native sequences, these are normally poorly immunogenic and do not induce protection, as demonstrated in our research. After attempting many synthetic strategies for improving the immunogenicity properties of these sequences, the approach consisting of identifying high binding motifs present in those, and then performing specific changes on amino-acids belonging to such motifs, has proven to be a workable strategy. In addition, other strategies consisting of chemically introducing non-natural constraints to the backbone topology of the molecule and modifying the α-carbon asymmetry are becoming valuable tools to be considered in this pursuit. Non-natural structural constraints to the peptide backbone can be achieved by introducing peptide bond isosters such as reduced amides, partially retro or retro-inverso modifications or even including urea motifs. The second can be obtained by strategically replacing L-amino-acids with their enantiomeric forms for obtaining both structurally site-directed designed immunogens as potential vaccine candidates and their Ig structural molecular images, both having immuno-therapeutic effects for preventing and controlling malaria. Full article
(This article belongs to the Special Issue Solid Phase Synthesis)
Open AccessArticle Antioxidant Phenolic Compounds of Dracaena Cambodiana
Molecules 2010, 15(12), 8904-8914; doi:10.3390/molecules15128904
Received: 6 November 2010 / Revised: 30 November 2010 / Accepted: 2 December 2010 / Published: 6 December 2010
Cited by 13 | PDF Full-text (267 KB)
Abstract
The antioxidant activities of the petroleum ether, ethyl acetate, n-BuOH and water extract fractions from Dracaena cambodiana Pierre ex Gagnep were evaluated in this study. The ethyl acetate fraction contained the highest amount of total phenolics and total flavonoids, and showed the
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The antioxidant activities of the petroleum ether, ethyl acetate, n-BuOH and water extract fractions from Dracaena cambodiana Pierre ex Gagnep were evaluated in this study. The ethyl acetate fraction contained the highest amount of total phenolics and total flavonoids, and showed the greatest DPPH˙, ABTS+ and Superoxide anion radical-scavenging capacities. The DPPH˙, ABTS+ and Superoxide anion radical-scavenging capacities of nine compounds isolated from the ethyl acetate fraction were also evaluated. The results indicated that these compounds contributed to the antioxidant activity of D. cambodiana. Therefore, D. cambodiana and these compounds might be used as natural antioxidants. Full article
Open AccessArticle Influence of Polarity of Solvents on the Spectral Properties of Bichromophoric Coumarins
Molecules 2010, 15(12), 8915-8932; doi:10.3390/molecules15128915
Received: 12 November 2010 / Revised: 1 December 2010 / Accepted: 6 December 2010 / Published: 7 December 2010
Cited by 16 | PDF Full-text (259 KB)
Abstract
Absorption and fluorescence spectra of bichromophoric coumarins were investigated in different solvents and in polymer matrices. These bichromophoric coumarins were composed of a coumarin dimethylamino-substituted at position 7 or unsubstituted coumarin and phthalimide or a 1,8-naphthylimide linked with an iminomethyl bridge to the
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Absorption and fluorescence spectra of bichromophoric coumarins were investigated in different solvents and in polymer matrices. These bichromophoric coumarins were composed of a coumarin dimethylamino-substituted at position 7 or unsubstituted coumarin and phthalimide or a 1,8-naphthylimide linked with an iminomethyl bridge to the position 3 or 8 of the coumarin ring. Absorption spectra of 7-dimethylamino derivatives in position 3 of coumarin were quite similar, exhibiting broad bands around 430-440 nm like the parent compound 7-dimethylaminocoumarin-3-carbaldehyde. For coumarin derivatives substituted in position 8, the absorption maximum was shifted to shorter wavelength as for derivatives without position 7 dimethylamino substitution. The most intense fluorescence was observed for 7-(N,N-dimethylamino)-3-[(N-phtalimidoyl)iminomethyl]coumarin in polar solvent, while intense fluorescence was observed for 7-(N,N-dimethylamino)-3-[N-(1,3-dioxobenz[de]isoquinolinyl)iminomethyl]-coumarin in non polar solvent (chloroform), comparable with the fluorescence of 7-amino-4-methylcoumarin. Spectral measurements of bichromophoric coumarins in polymer matrices revealed that the maxima lies in between those for chloroform and methanol yielding more intense fluorescence then in solutions. Completely different solvent effects were observed for 7-(N,N-dimethylamino)-3-[N-(1,3-dioxobenz[de]isoquinolinyl)imino-methyl]coumarin and 7-(N,N-dimethylamino)-3-[(N-phtalimidoyl)iminomethyl]coumarin. With addition of polar methanol the intensity of fluorescence decreases, yielding a Stern-Volmer-like constant of 0.54 dm3 mol−1 for 7-(N,N-dimethylamino)-3-[N-(1,3-dioxo-benz[de]isoquinolinyl)iminomethyl]coumarin and an even higher one of 1.08 dm3 mol−1 for 7-dimethylaminocoumarin-3-carbaldehyde compared to the rather low one of 0.024 dm3 mol−1 for 7-amino-4-methylcoumarin. Contrary to this, addition of methanol under identical conditions brings about an increase in fluorescence intensity of 7-(N,N-dimethylamino)-3-[(N-phtalimidoyl)iminomethyl]coumarin (about 60-fold). The reasons for these different solvent effects are discussed. Full article
Open AccessArticle Apoptotic Effects of γ-Mangostin from the Fruit Hull of Garcinia mangostana on Human Malignant Glioma Cells
Molecules 2010, 15(12), 8953-8966; doi:10.3390/molecules15128953
Received: 22 October 2010 / Revised: 2 December 2010 / Accepted: 6 December 2010 / Published: 7 December 2010
Cited by 14 | PDF Full-text (652 KB)
Abstract
Gliomas are a common type of primary brain tumor with glioblastoma multiforme accounting for the majority of human brain tumors. In this paper, high grade human malignant glioblastomas (MGs) including U87 MG and GBM 8401 were used to evaluate the antitumor effects of
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Gliomas are a common type of primary brain tumor with glioblastoma multiforme accounting for the majority of human brain tumors. In this paper, high grade human malignant glioblastomas (MGs) including U87 MG and GBM 8401 were used to evaluate the antitumor effects of γ-mangostin, a xanthone derivative isolated and purified from the hull of the tropical fruit Garcinia mangostana. The γ-mangostin showed potent antiproliferative activity toward MGs in dose- and time-dependent manners. In addition, flow cytometric analysis of cell morphology in the apoptotic cells revealed an increase in hypodiploid cells in γ-mangostin treated U87 MG and GBM 8401 cells, while significant enhancement of intracellular peroxide production was detected in the same γ-mangostin treated cells by DCHDA assay and DiOC6(3) stain. g-Mangostin induced apoptosis, which in turn mediates cytotoxicity in human MG cells was prevented by the addition of catalase. Naturally derived medicines and herbal therapies are drawing increasing attention in regard to the treatment of many health issues, and this includes the testing of new phytochemicals or nutrients for brain tumor patients. This has led to γ-mangostin being identified as a potential leading compound for the development of an anti-brain tumor agent. Full article
(This article belongs to the collection Bioactive Compounds)
Open AccessArticle Acanmontanoside, a New Phenylethanoid Diglycoside from Acanthus montanus
Molecules 2010, 15(12), 8967-8972; doi:10.3390/molecules15128967
Received: 18 October 2010 / Revised: 26 November 2010 / Accepted: 6 December 2010 / Published: 7 December 2010
Cited by 4 | PDF Full-text (117 KB)
Abstract
A new phenylethanoid glycoside acylated with syringic acid, namely acanmontanoside, was isolated from the aerial portions of Acanthus montanus (Nees). T. Anderson, along with decaffeoylverbascoside, verbascoside, isoverbascoside, leucosceptoside A, (2R)-2-O-b-D-glucopyranosyl-2H-1,4-benzoxazin-3(4H)-one (HBOA-Glc), (2R)-2-O
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A new phenylethanoid glycoside acylated with syringic acid, namely acanmontanoside, was isolated from the aerial portions of Acanthus montanus (Nees). T. Anderson, along with decaffeoylverbascoside, verbascoside, isoverbascoside, leucosceptoside A, (2R)-2-O-b-D-glucopyranosyl-2H-1,4-benzoxazin-3(4H)-one (HBOA-Glc), (2R)-2-O-b-D-glucopyranosyl-4-hydroxy-2H-1,4-benzoxazin-3(4H)-one (DIBOA-Glc), (3R)-1-octen-3-ol-3-O-b-D-xylopyranosyl-(1→6)-O-b-D-glucopyranoside and ebracteatoside B. The structure elucidations were based on physical data and spectroscopic analyses including 1D- and 2D-NMR. Full article
(This article belongs to the Special Issue Phenolics and Polyphenolics)
Open AccessArticle Preparation and Properties of New Co-Crystals of Ibandronate with Gluco- or Galactopyranoside Derivatives
Molecules 2010, 15(12), 8973-8987; doi:10.3390/molecules15128973
Received: 22 November 2010 / Revised: 3 December 2010 / Accepted: 7 December 2010 / Published: 8 December 2010
Cited by 5 | PDF Full-text (412 KB)
Abstract
Mixtures of ibandronate monosodium salt with eleven gluco- and/or galacto-pyranoside derivatives as counterions were designed to prepare co-crystals with improved intestinal absorption. In general, gastrointestinal absorption of bisphosphonates after oral administration is approximately 1%. Co-crystals were generated by means of thermodynamically and/or kinetically
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Mixtures of ibandronate monosodium salt with eleven gluco- and/or galacto-pyranoside derivatives as counterions were designed to prepare co-crystals with improved intestinal absorption. In general, gastrointestinal absorption of bisphosphonates after oral administration is approximately 1%. Co-crystals were generated by means of thermodynamically and/or kinetically controlled crystallization processes. Seventy-seven prepared samples were analyzed by means of FT-NIR, FT-Raman spectrometry and solid state NMR spectroscopy. New entities of ibandronate monosodium salt with phenyl-β-d-galactopyranoside were found and characterized. The absorption of these potential new co-crystals was investigated by means of PAMPA experiments. In the present study the relationships between the chemical structures of the studied compounds required for co-crystal generation are discussed. Full article
(This article belongs to the Special Issue ECSOC-13)
Open AccessArticle Antidiabetic Properties and Mechanism of Action of Gynura procumbens Water Extract in Streptozotocin-Induced Diabetic Rats
Molecules 2010, 15(12), 9008-9023; doi:10.3390/molecules15129008
Received: 23 October 2010 / Accepted: 6 December 2010 / Published: 8 December 2010
Cited by 28 | PDF Full-text (402 KB)
Abstract
Gynura procumbens (Lour.) Merr (family Compositae) is cultivated in Southeast Asia, especially Indonesia, Malaysia and Thailand, for medicinal purposes. This study evaluated the in vivo hypoglycemic properties of the water extract of G. procumbens following 14 days of treatment and in vitro in
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Gynura procumbens (Lour.) Merr (family Compositae) is cultivated in Southeast Asia, especially Indonesia, Malaysia and Thailand, for medicinal purposes. This study evaluated the in vivo hypoglycemic properties of the water extract of G. procumbens following 14 days of treatment and in vitro in RIN-5F cells. Glucose absorption from the intestines and its glucose uptake in abdominal skeletal muscle were assessed. The antidiabetic effect of water extract of G. procumbens leaves was investigated in streptozotocin-induced diabetic rats. The intraperitoneal glucose tolerance test (IPGTT) was performed in diabetic rats treated with G. procumbens water extract for 14 days. In the IPGTT, blood was collected for insulin and blood glucose measurement. After the IPGTT, the pancreases were collected for immunohistochemical study of β-cells of the islets of Langerhans. The possible antidiabetic mechanisms of G. procumbens were assessed through in vitro RIN-5F cell study, intestinal glucose absorption and glucose uptake by muscle. The results showed that G. procumbens significantly decreased blood glucose levels after 14 days of treatment and improved outcome of the IPGTT. However, G. procumbens did not show a significant effect on insulin level either in the in vivo test or the in vitro RIN-5F cell culture study. G. procumbens also showed minimal effects on β-cells of the islets of Langerhans in the pancreas. However, G. procumbens only significantly increased glucose uptake by muscle tissues. From the findings we can conclude that G. procumbens water extract exerted its hypoglycemic effect by promoting glucose uptake by muscles. Full article
(This article belongs to the Section Natural Products)
Open AccessArticle Synthesis and Biological Activity of Novel Phenyltriazolinone Derivatives
Molecules 2010, 15(12), 9024-9034; doi:10.3390/molecules15129024
Received: 27 October 2010 / Revised: 18 November 2010 / Accepted: 22 November 2010 / Published: 9 December 2010
Cited by 4 | PDF Full-text (155 KB)
Abstract
Phenyltriazolinones are one of the most important classes of herbicides targeting the protoporphyrinogen oxidase enzyme. A series of triazolinone derivatives containing a strobilurin pharmacophore were designed and synthesized with the aim of discovering new phenyltriazolinone analogues with high activity. The herbicidal activity of
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Phenyltriazolinones are one of the most important classes of herbicides targeting the protoporphyrinogen oxidase enzyme. A series of triazolinone derivatives containing a strobilurin pharmacophore were designed and synthesized with the aim of discovering new phenyltriazolinone analogues with high activity. The herbicidal activity of the synthesized compounds was assayed and some of the test compounds displayed moderate herbicidal activity at 150 g ai/ha. Full article
Open AccessArticle A Mangifera indica L. Extract Could Be Used to Treat Neuropathic Pain and Implication of Mangiferin
Molecules 2010, 15(12), 9035-9045; doi:10.3390/molecules15129035
Received: 27 October 2010 / Revised: 29 November 2010 / Accepted: 1 December 2010 / Published: 9 December 2010
Cited by 24 | PDF Full-text (179 KB)
Abstract
It has been accepted that neuroinflammation, oxidative stress and glial activation are involved in the central sensitization underlying neuropathic pain. Vimang is an aqueous extract of Mangifera indica L. traditionally used in Cuba for its analgesic, anti-inflammatory, antioxidant and immunomodulatory properties. Several formulations
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It has been accepted that neuroinflammation, oxidative stress and glial activation are involved in the central sensitization underlying neuropathic pain. Vimang is an aqueous extract of Mangifera indica L. traditionally used in Cuba for its analgesic, anti-inflammatory, antioxidant and immunomodulatory properties. Several formulations are available, and also for mangiferin, its major component. Preclinical studies demonstrated that these products prevented tumor necrosis factor α -induced IκB degradation and the binding of nuclear factor κB to DNA, which induces the transcription of genes implicated in the expression of some mediators and enzymes involved in inflammation, pain, oxidative stress and synaptic plasticity. In this paper we propose its potential utility in the neuropathic pain treatment. This hypothesis is supported in the cumulus of preclinical and clinical evidence around the extract and mangiferin, its major component, and speculates about the possible mechanism of action according to recent advances in the physiopathology of neuropathic pain. Full article
Open AccessArticle Synthesis and Antiviral Activity of 5‑(4‑Chlorophenyl)-1,3,4-Thiadiazole Sulfonamides
Molecules 2010, 15(12), 9046-9056; doi:10.3390/molecules15129046
Received: 23 August 2010 / Revised: 10 November 2010 / Accepted: 30 November 2010 / Published: 9 December 2010
Cited by 45 | PDF Full-text (227 KB)
Abstract
Starting from 4-chlorobenzoic acid, 10 new 5-(4-chlorophenyl)-N-substituted-N-1,3,4-thiadiazole-2-sulfonamide derivatives were synthesized in six-steps. Esterification of 4-chlorobenzoic acid with methanol and subsequent hydrazination, salt formation and cyclization afforded 5-(4-chlorophen-yl)-1,3,4-thiadiazole-2-thiol (5). Conversion of this intermediate into sulfonyl chloride 6,
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Starting from 4-chlorobenzoic acid, 10 new 5-(4-chlorophenyl)-N-substituted-N-1,3,4-thiadiazole-2-sulfonamide derivatives were synthesized in six-steps. Esterification of 4-chlorobenzoic acid with methanol and subsequent hydrazination, salt formation and cyclization afforded 5-(4-chlorophen-yl)-1,3,4-thiadiazole-2-thiol (5). Conversion of this intermediate into sulfonyl chloride 6, followed by nucleophilic attack of the amines gave the title sulfonamides 7a-7j whose structures were confirmed by NMR, IR and elemental analysis. The bioassay tests showed that compounds 7b and 7i possessed certain anti-tobacco mosaic virus activity. Full article
Open AccessArticle Structural Relationship and Binding Mechanisms of Five Flavonoids with Bovine Serum Albumin
Molecules 2010, 15(12), 9092-9103; doi:10.3390/molecules15129092
Received: 9 October 2010 / Revised: 1 December 2010 / Accepted: 6 December 2010 / Published: 9 December 2010
Cited by 51 | PDF Full-text (386 KB)
Abstract
Flavonoids are structurally diverse and the most ubiquitous groups of dietary polyphenols distributed in various fruits and vegetables. In this study, the interaction between five flavonoids, namely formononetin-7-O-β-D-glucoside, calycosin- 7-O-β-D-glucoside, calycosin, rutin, and quercetin, and bovine serum albumin (BSA)
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Flavonoids are structurally diverse and the most ubiquitous groups of dietary polyphenols distributed in various fruits and vegetables. In this study, the interaction between five flavonoids, namely formononetin-7-O-β-D-glucoside, calycosin- 7-O-β-D-glucoside, calycosin, rutin, and quercetin, and bovine serum albumin (BSA) was investigated by fluorescence and UV-vis absorbance spectroscopy. In the discussion, it was proved that the fluorescence quenching of BSA by flavonoids was a result of the formation of a flavonoid-BSA complex. Fluorescence quenching constants were determined using the Stern-Volmer and Lineweaver-Burk equations to provide a measure of the binding affinity between the flavonoids and BSA. The binding constants ranked in the order quercetin > rutin > calycosin > calycosin-7-O-β-D-glucoside ≈ formononetin-7-O-β-D-glucoside. The results of thermodynamic parameters ΔG, ΔH, and ΔS at different temperatures indicated that the hydrophobic interaction played a major role in flavonoid-BSA association. The distance r between BSA and acceptor flavonoids was also obtained according to Förster’s theory of non-radiative energy transfer. Full article
Open AccessArticle Unexplored Nucleophilic Ring Opening of Aziridines
Molecules 2010, 15(12), 9135-9144; doi:10.3390/molecules15129135
Received: 24 November 2010 / Revised: 1 December 2010 / Accepted: 6 December 2010 / Published: 10 December 2010
PDF Full-text (279 KB)
Abstract
The reactivity of dianions of carboxylic acids towards aziridines has been studied. Although, a similar reactivity to that of enolates from ketones, esters or amides has been observed, the method directly yields g-aminoacids in one step. The method is complementary of previous results
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The reactivity of dianions of carboxylic acids towards aziridines has been studied. Although, a similar reactivity to that of enolates from ketones, esters or amides has been observed, the method directly yields g-aminoacids in one step. The method is complementary of previous results of enenediolate reactivity with other electrophiles. A comparative study with the reactivity of this enediolates with epoxides is included. Full article
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Open AccessArticle Antioxidant Activities of Total Phenols of Prunella vulgaris L. in Vitro and in Tumor-bearing Mice
Molecules 2010, 15(12), 9145-9156; doi:10.3390/molecules15129145
Received: 19 September 2010 / Revised: 22 November 2010 / Accepted: 8 December 2010 / Published: 10 December 2010
Cited by 18 | PDF Full-text (229 KB)
Abstract
Prunella vulgaris L. (PV, Labiatae) is known as a self-heal herb. The different extracts of dried spikes were studied for the best antioxidant active compounds. The 60% ethanol extract (P-60) showed strong antioxidant activity based on the results of 2,2’-azino-di(3-ethylbenzthiazoline-6-sulfonic acid (ABTS˙+), 2,2-diphenyl-1-picrylhydrazyl
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Prunella vulgaris L. (PV, Labiatae) is known as a self-heal herb. The different extracts of dried spikes were studied for the best antioxidant active compounds. The 60% ethanol extract (P-60) showed strong antioxidant activity based on the results of 2,2’-azino-di(3-ethylbenzthiazoline-6-sulfonic acid (ABTS˙+), 2,2-diphenyl-1-picrylhydrazyl (DPPH) and ferric reducing antioxidant power (FRAP) assay methods. High performance liquid chromatography (HPLC) and LC/MS analysis showed that the main active compounds in P-60 were phenols, such as caffeic acid, rosmarinic acid, rutin and quercetin. Total phenols were highly correlated with the antioxidant activity (R2 = 0.9988 in ABTS˙+; 0.6284 in DPPH and 0.9673 FRAP tests). P-60 could inhibit significantly the tumor growth in C57BL/6 mice. It can also been showed that increased superoxide dismutase (SOD) activity and decreased malondialdehyde (MDA) content in serum of tumor-bearing mice. These results suggested that P-60 extract had high antioxidant activity in vitro and in vivo and total phenols played an important role in antioxidant activity for inhibition of tumor growth. Full article
Open AccessArticle Sonogashira Reaction of Aryl and Heteroaryl Halides with Terminal Alkynes Catalyzed by a Highly Efficient and Recyclable Nanosized MCM-41 Anchored Palladium Bipyridyl Complex
Molecules 2010, 15(12), 9157-9173; doi:10.3390/molecules15129157
Received: 11 November 2010 / Revised: 6 December 2010 / Accepted: 9 December 2010 / Published: 10 December 2010
Cited by 33 | PDF Full-text (171 KB)
Abstract
A heterogeneous catalyst, nanosized MCM-41-Pd, was used to catalyze the Sonogashira coupling of aryl and heteroaryl halides with terminal alkynes in the presence of CuI and triphenylphosphine. The coupling products were obtained in high yields using low Pd loadings to 0.01 mol%, and
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A heterogeneous catalyst, nanosized MCM-41-Pd, was used to catalyze the Sonogashira coupling of aryl and heteroaryl halides with terminal alkynes in the presence of CuI and triphenylphosphine. The coupling products were obtained in high yields using low Pd loadings to 0.01 mol%, and the nanosized MCM-41-Pd catalyst was recovered by centrifugation of the reaction solution and re-used in further runs without significant loss of reactivity. Full article
(This article belongs to the Special Issue Cross-Coupling Reactions in Organic Synthesis)
Open AccessArticle Synthesis and Biological Activity of trans-Tiliroside Derivatives as Potent Anti-Diabetic Agents
Molecules 2010, 15(12), 9174-9183; doi:10.3390/molecules15129174
Received: 29 October 2010 / Revised: 7 December 2010 / Accepted: 8 December 2010 / Published: 10 December 2010
Cited by 12 | PDF Full-text (181 KB)
Abstract
A set of novel trans-tiliroside derivatives were synthesized. The structures of the derivatives were identified by their IR, 1H-NMR, and MS spectra analysis. Their anti-diabetic activities were evaluated on the insulin resistant (IR) HepG2 cell model. As a result, compounds 7a
[...] Read more.
A set of novel trans-tiliroside derivatives were synthesized. The structures of the derivatives were identified by their IR, 1H-NMR, and MS spectra analysis. Their anti-diabetic activities were evaluated on the insulin resistant (IR) HepG2 cell model. As a result, compounds 7a, 7c, 7h, and trans-tiliroside exhibited significant glucose consumption-enhancing effects in IR-HepG2 cells compared with the positive control (metformin). This research provides useful clues for further design and discovery of anti-diabetic agents. Full article
(This article belongs to the Special Issue Structure-Based Drug Design)
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Open AccessArticle Volatile Compounds of Young Wines from Cabernet Sauvignon, Cabernet Gernischet and Chardonnay Varieties Grown in the Loess Plateau Region of China
Molecules 2010, 15(12), 9184-9196; doi:10.3390/molecules15129184
Received: 6 October 2010 / Revised: 6 December 2010 / Accepted: 8 December 2010 / Published: 10 December 2010
Cited by 34 | PDF Full-text (221 KB)
Abstract
In order to elucidate the aroma components of wine produced in the Loess Plateau region of China, volatile compounds of young wines from Cabernet Sauvignon, Cabernet Gernischet and Chardonnay varieties grown in the new ecological region were investigated for the first time in
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In order to elucidate the aroma components of wine produced in the Loess Plateau region of China, volatile compounds of young wines from Cabernet Sauvignon, Cabernet Gernischet and Chardonnay varieties grown in the new ecological region were investigated for the first time in this research. Among the volatile compounds analyzed by HS-SPME with GC-MS, a total of 45, 44 and 42 volatile compounds were identified and quantified in Cabernet Sauvignon, Cabernet Gernischet and Chardonnay wines, respectively. In the volatiles detected, alcohols formed the most abundant group in the aroma compounds of the three wines, followed by esters and fatty acids. According to their odor active values (OAVs), 18 volatile compounds were always present in the three wines at concentrations higher than their threshold values, but ethyl octanoate, ethyl hexanoate, and isoamyl acetate were found to jointly contribute to 92.9%, 93.3%, and 98.7%, of the global aroma of Cabernet Sauvignon, Cabernet Gernischet and Chardonnay wines, respectively. These odorants are associated with “fruity’’ and ‘‘ripe fruit’’ odor descriptors. Full article
Open AccessArticle An Efficient Synthesis of 1-Aryl-3-(indole-3-yl)-3-(2-aryl-1,2,3-triazol-4-yl)propan-1-one Catalyzed by a Brønsted Acid Ionic Liquid
Molecules 2010, 15(12), 9197-9204; doi:10.3390/molecules15129197
Received: 11 October 2010 / Revised: 3 December 2010 / Accepted: 7 December 2010 / Published: 10 December 2010
PDF Full-text (193 KB)
Abstract
An efficient synthesis of novel 1-aryl-3-(indole-3-yl)-3-(2-aryl-1,2,3-triazol-4-yl)propan-1-ones from indoles and 1-aryl-3-(2-aryl-1,2,3-triazol-4-yl)propan-1-one using a Brønsted acid ionic liquid [Sbmim][HSO4] as catalyst is described. Satisfactory results with excellent yields and short reaction time were obtained in the experiments. The catalyst could be recovered conveniently
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An efficient synthesis of novel 1-aryl-3-(indole-3-yl)-3-(2-aryl-1,2,3-triazol-4-yl)propan-1-ones from indoles and 1-aryl-3-(2-aryl-1,2,3-triazol-4-yl)propan-1-one using a Brønsted acid ionic liquid [Sbmim][HSO4] as catalyst is described. Satisfactory results with excellent yields and short reaction time were obtained in the experiments. The catalyst could be recovered conveniently and reused efficiently. Full article
Open AccessArticle Alkaloids from Stems of Esenbeckia leiocarpa Engl. (Rutaceae) as Potential Treatment for Alzheimer Disease
Molecules 2010, 15(12), 9205-9213; doi:10.3390/molecules15129205
Received: 15 November 2010 / Revised: 2 December 2010 / Accepted: 6 December 2010 / Published: 13 December 2010
Cited by 21 | PDF Full-text (77 KB)
Abstract
Esenbeckia leiocarpa Engl. (Rutaceae), popularly known as guarantã, goiabeira, is a native tree from Brazil. Bioactivity-guided fractionation of the ethanol stems extract afforded the isolation of six alkaloids: leiokinine A, leptomerine, kokusaginine, skimmianine, maculine and flindersiamine. All isolated compounds were tested for
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Esenbeckia leiocarpa Engl. (Rutaceae), popularly known as guarantã, goiabeira, is a native tree from Brazil. Bioactivity-guided fractionation of the ethanol stems extract afforded the isolation of six alkaloids: leiokinine A, leptomerine, kokusaginine, skimmianine, maculine and flindersiamine. All isolated compounds were tested for acetyl cholinesterase inhibition, in vitro and displayed anticholinesterasic activity. The alkaloid leptomerine showed the highest activity (IC50 = 2.5 mM), similar to that of the reference compound galanthamine (IC50 = 1.7 mM). The results showed for the first time the presence of alkaloids leptomerine and skimmianine in E. leiocarpa (Engl.) with potent anticholinesterasic activity. Full article
(This article belongs to the Section Natural Products)
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Open AccessArticle An Improved in Vivo Deuterium Labeling Method for Measuring the Biosynthetic Rate of Cytokinins
Molecules 2010, 15(12), 9214-9229; doi:10.3390/molecules15129214
Received: 10 October 2010 / Accepted: 14 December 2010 / Published: 15 December 2010
Cited by 2 | PDF Full-text (253 KB)
Abstract
An improved method for determining the relative biosynthetic rate of isoprenoid cytokinins has been developed. A set of 11 relevant isoprenoid cytokinins, including zeatin isomers, was separated by ultra performance liquid chromatography in less than 6 min. The iP-type cytokinins were observed to
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An improved method for determining the relative biosynthetic rate of isoprenoid cytokinins has been developed. A set of 11 relevant isoprenoid cytokinins, including zeatin isomers, was separated by ultra performance liquid chromatography in less than 6 min. The iP-type cytokinins were observed to give rise to a previously-unknown fragment at m/z 69; we suggest that the diagnostic (204-69) transition can be used to monitor the biosynthetic rate of isopentenyladenine. Furthermore, we found that by treating the cytokinin nucleotides with alkaline phosphatase prior to analysis, the sensitivity of the detection process could be increased. In addition, derivatization (propionylation) improved the ESI-MS response by increasing the analytes' hydrophobicity. Indeed, the ESI-MS response of propionylated isopentenyladenosine was about 34% higher than that of its underivatized counterpart. Moreover, the response of the derivatized zeatin ribosides was about 75% higher than that of underivatized zeatin ribosides. Finally, we created a web-based calculator (IZOTOP) that facilitates MS/MS data processing and offer it freely to the research community. Full article
(This article belongs to the Special Issue Phytochemicals with Signaling, Medicinal and Therapeutic Properties)
Open AccessArticle Antimicrobial Activity of Sphingolipids Isolated from the Stems of Cucumber (Cucumis sativus L.)
Molecules 2010, 15(12), 9288-9297; doi:10.3390/molecules15129288
Received: 2 December 2010 / Revised: 10 December 2010 / Accepted: 13 December 2010 / Published: 15 December 2010
Cited by 20 | PDF Full-text (222 KB)
Abstract
Three antimicrobial sphingolipids were separated by bioassay-guided isolation from the chloroform fraction of the crude methanol extract of cucumber (Cucumis sativus L.) stems and identified as (2S,3S,4R,10E)-2-[(2'R)-2-hydroxytetra-cosanoylamino]-1,3,4-octadecanetriol-10-ene (1), 1-O-β-D-glucopyranosyl(2S,3S,4R,10E
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Three antimicrobial sphingolipids were separated by bioassay-guided isolation from the chloroform fraction of the crude methanol extract of cucumber (Cucumis sativus L.) stems and identified as (2S,3S,4R,10E)-2-[(2'R)-2-hydroxytetra-cosanoylamino]-1,3,4-octadecanetriol-10-ene (1), 1-O-β-D-glucopyranosyl(2S,3S,4R,10E)-2-[(2'R)-2-hydroxy-tetracosanoylamino]-1,3,4-octadecanetriol-10-ene (2) and soya-cerebroside I (3) by their physicochemical properties and spectroscopic analysis. They were evaluated to show antifungal and antibacterial activity on test microorganisms including four fungal and three bacterial species. Among them, compound 1, a relatively low polarity aglycone,  exhibited stronger antimicrobial activity than its corresponding glycoside 2. The results indicated that sphingolipids could be the main antimicrobial compounds in the crude methanol extract of cucumber stems. Full article
(This article belongs to the collection Bioactive Compounds)
Open AccessArticle A Novel Benzo[f][1,7]Naphthyridine Produced by Streptomyces Albogriseolus from Mangrove Sediments
Molecules 2010, 15(12), 9298-9307; doi:10.3390/molecules15129298
Received: 24 October 2010 / Revised: 30 November 2010 / Accepted: 7 December 2010 / Published: 15 December 2010
Cited by 12 | PDF Full-text (244 KB)
Abstract
Mangrove Streptomyces represent a rich source of novel bioactive compounds in medicinal research. A novel alkaloid, named 1-N-methyl-3-methylamino-[N-butanoic acid-3¢-(9¢-methyl-8¢-propen-7¢-one)-amide]-benzo[f][1,7]naphthyridine-2-one (1) was isolated from Streptomyces albogriseolus originating from mangrove sediments. The structure of compound 1 was elucidated by
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Mangrove Streptomyces represent a rich source of novel bioactive compounds in medicinal research. A novel alkaloid, named 1-N-methyl-3-methylamino-[N-butanoic acid-3¢-(9¢-methyl-8¢-propen-7¢-one)-amide]-benzo[f][1,7]naphthyridine-2-one (1) was isolated from Streptomyces albogriseolus originating from mangrove sediments. The structure of compound 1 was elucidated by extensive spectroscopic data analyses and verified by the 13C-NMR calculation at the B3LYP/6-311+G(2d,p) level of theory. Full article
(This article belongs to the Section Natural Products)
Open AccessArticle Antioxidant Activity of Lignin Phenolic Compounds Extracted from Kraft and Sulphite Black Liquors
Molecules 2010, 15(12), 9308-9322; doi:10.3390/molecules15129308
Received: 19 October 2010 / Revised: 13 December 2010 / Accepted: 14 December 2010 / Published: 16 December 2010
Cited by 38 | PDF Full-text (276 KB)
Abstract
The antioxidant activity of the phenolic compounds present in industrial black liquors obtained from the two cooking processes (kraft and sulphite) used in Portugal to produce Eucalyptus globulus pulp was evaluated. The black liquors treated at several pH values were extracted with ethyl
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The antioxidant activity of the phenolic compounds present in industrial black liquors obtained from the two cooking processes (kraft and sulphite) used in Portugal to produce Eucalyptus globulus pulp was evaluated. The black liquors treated at several pH values were extracted with ethyl acetate. Phenolic fractions were further separated by liquid chromatography of the crude extracts of kraft liquor at pH = 6 and sulphite liquor at the original pH. Total phenolic content was determined in terms of gallic acid equivalents (Folin-Ciocalteu colorimetric method), and the antioxidant activity in the crude extracts at several pH values and in the separated fractions was measured using the DPPH test for radical scavenging capacity. The total phenolic content of crude extracts and separated fractions ranged from 92.7 to 181.6 and from 91.6 to 1,099.6 mg GAE/g, respectively, while the antioxidant activity index (AAI) ranged from 2.20 to 3.41 and from 2.21 to 11.47 respectively, showing very strong antioxidant activity in all studied cases. The fractions separated by column chromatography were submitted to mass spectrometry analysis and the results were compared to others in the literature of natural products, mainly from Eucalyptus, and the characteristic bands of functional groups were identified by 1H-NMR and FTIR. These methods allowed the identification of 17 phenolic compounds. Full article
(This article belongs to the Special Issue Phenolics and Polyphenolics)
Open AccessArticle The Influence of Mixed Activators on Ethylene Polymerization and Ethylene/1-Hexene Copolymerization with Silica-Supported Ziegler-Natta Catalyst
Molecules 2010, 15(12), 9323-9339; doi:10.3390/molecules15129323
Received: 15 November 2010 / Revised: 10 December 2010 / Accepted: 14 December 2010 / Published: 16 December 2010
Cited by 9 | PDF Full-text (1017 KB)
Abstract
This article reveals the effects of mixed activators on ethylene polymerization and ethylene/1-hexene copolymerization over MgCl2/SiO2-supported Ziegler-Natta (ZN) catalysts. First, the conventional ZN catalyst was prepared with SiO2 addition. Then, the catalyst was tested for ethylene polymerization and
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This article reveals the effects of mixed activators on ethylene polymerization and ethylene/1-hexene copolymerization over MgCl2/SiO2-supported Ziegler-Natta (ZN) catalysts. First, the conventional ZN catalyst was prepared with SiO2 addition. Then, the catalyst was tested for ethylene polymerization and ethylene/1-hexene (E/H) co-polymerization using different activators. Triethylaluminum (TEA), tri-n-hexyl aluminum (TnHA) and diethyl aluminum chloride (DEAC), TEA+DEAC, TEA+TnHA, TnHA+ DEAC, TEA+DEAC+TnHA mixtures, were used as activators in this study. It was found that in the case of ethylene polymerization with a sole activator, TnHA exhibited the highest activity among other activators due to increased size of the alkyl group. Further investigation was focused on the use of mixed activators. The activity can be enhanced by a factor of three when the mixed activators were employed and the activity of ethylene polymerization apparently increased in the order of TEA+ DEAC+TnHA > TEA+DEAC > TEA+TnHA. Both the copolymerization activity and crystallinity of the synthesized copolymers were strongly changed when the activators were changed from TEA to TEA+DEAC+TnHA mixtures or pure TnHA and pure DEAC.  As for ethylene/1-hexene copolymerization the activity apparently increased in the order of TEA+DEAC+TnHA > TEA+TnHA > TEA+DEAC > TnHA+DEAC > TEA > TnHA > DEAC. Considering the properties of the copolymer obtained with the mixed TEA+DEAC+TnHA, its crystallinity decreased due to the presence of TnHA in the mixed activator. The activators thus exerted a strong influence on copolymer structure. An increased molecular weight distribution (MWD) was observed, without significant change in polymer morphology. Full article
Open AccessArticle Evaluation of the Bioactivity of Novel Spiroisoxazoline TypeCompounds against Normal and Cancer Cell Lines
Molecules 2010, 15(12), 9340-9353; doi:10.3390/molecules15129340
Received: 5 October 2010 / Revised: 3 November 2010 / Accepted: 2 December 2010 / Published: 17 December 2010
Cited by 14 | PDF Full-text (163 KB)
Abstract
The aim of this study was to investigate the in vitro cellular activity of novel spiroisoxazoline type compounds against normal and cancer cell lines from lung tissue (Hs888Lu), neuron-phenotypic cells (SH-SY5Y), neuroblastoma (SH-SY5Y), human histiocytic lymphoma (U937), lung cancer (A549), and leukaemia (HL-60).
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The aim of this study was to investigate the in vitro cellular activity of novel spiroisoxazoline type compounds against normal and cancer cell lines from lung tissue (Hs888Lu), neuron-phenotypic cells (SH-SY5Y), neuroblastoma (SH-SY5Y), human histiocytic lymphoma (U937), lung cancer (A549), and leukaemia (HL-60). Our bioassay program revealed that the spiroisoxazoline type compounds show cytotoxicity only in lymphoma cell lines, which is in contrast with the pyrrolidine precursor of these spiroisoxazoline compounds, where significant cytotoxicity is seen in all normal and cancer cell lines. These data suggest a tumour-specific mechanism of action. In addition these data also show that spiroisoxazoline compounds are non-toxic in the human neuronphenotypic neuroblastoma SH-SY5Y cell line, and furthermore that they might protect cells from neurodegenerative disease. Full article
(This article belongs to the collection Bioactive Compounds)
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Open AccessArticle Synthesis of New Racemic α,α-Diaminocarboxylic Ester Derivatives
Molecules 2010, 15(12), 9354-9363; doi:10.3390/molecules15129354
Received: 26 October 2010 / Revised: 19 November 2010 / Accepted: 25 November 2010 / Published: 17 November 2010
PDF Full-text (182 KB)
Abstract New racemic methyl or ethyl α-aminoglycinate derivatives were synthesized by N-alkylation of amines (aniline, 4-methylaniline, 2-methylaniline, 2,4-dimethoxyaniline, 2-nitroaniline, 4-chloro-2-fluoroaniline, 2-naphthylamine, benzylamine, N,N-dibenzylamine, and cyclohexylamine) with methyl or ethyl α-azidoglycinate. Full article
Open AccessArticle Molecular Modeling Studies on 11H-Dibenz[b,e]azepine and Dibenz[b,f][1,4]oxazepine Derivatives as Potent Agonists of the Human TRPA1 Receptor
Molecules 2010, 15(12), 9364-9379; doi:10.3390/molecules15129364
Received: 22 November 2010 / Revised: 8 December 2010 / Accepted: 15 December 2010 / Published: 17 December 2010
Cited by 6 | PDF Full-text (271 KB)
Abstract
A computational strategy based on comparative molecular fields analysis (CoMFA) and comparative molecular similarity indices analysis (CoMSIA) was performed on a series of the 11H-dibenz[b,e]azepine and dibenz[b,f][1,4]oxazepine derivatives as potent agonists of the
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A computational strategy based on comparative molecular fields analysis (CoMFA) and comparative molecular similarity indices analysis (CoMSIA) was performed on a series of the 11H-dibenz[b,e]azepine and dibenz[b,f][1,4]oxazepine derivatives as potent agonists of the human TRPA1 receptor. The CoMFA and CoMSIA models resulting from a 21 molecule training set gave r2cv values of 0.631 and 0.542 and r2 values of 0.986 and 0.981, respectively. The statistically significant models were validated by a test set of five compounds with predictive r2pred. values of 0.967 and 0.981 for CoMFA and CoMSIA, respectively. A systemic external validation was also performed on the established models. The information obtained from 3D counter maps could facilitate the design of more potent human TRPA1 receptor agonists. Full article
Open AccessCommunication Frameshifting in the P6 cDNA Phage Display System
Molecules 2010, 15(12), 9380-9390; doi:10.3390/molecules15129380
Received: 9 November 2010 / Revised: 3 December 2010 / Accepted: 16 December 2010 / Published: 20 December 2010
Cited by 4 | PDF Full-text (427 KB)
Abstract
Phage display is a powerful technique that enables easy identification of targets for any type of ligand. Targets are displayed at the phage surface as a fusion protein to one of the phage coat proteins. By means of a repeated process of affinity
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Phage display is a powerful technique that enables easy identification of targets for any type of ligand. Targets are displayed at the phage surface as a fusion protein to one of the phage coat proteins. By means of a repeated process of affinity selection on a ligand, specific enrichment of displayed targets will occur. In our studies using C-terminal display of cDNA fragments to phage coat protein p6, we noticed the occasional enrichment of targets that do not contain an open reading frame. This event has previously been described in other phage display studies using N-terminal display of targets to phage coat proteins and was due to uncommon translational events like frameshifting. The aim of this study was to examine if C-terminal display of targets to p6 is also subjected to frameshifting. To this end, an enriched target not containing an open reading frame was selected and an E-tag was coupled at the C-terminus in order to measure target display at the surface of the phage. The tagged construct was subsequently expressed in 3 different reading frames and display of both target and E-tag measured to detect the occurrence of frameshifting. As a result, we were able to demonstrate display of the target both in the 0 and in the +1 reading frame indicating that frameshifting can also take place when C-terminal fusion to minor coat protein p6 is applied. Full article
(This article belongs to the Special Issue Phage Display of Combinatorial Libraries)
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Open AccessArticle Insecticidal Activity of Essential Oil of Carum Carvi Fruits from China and Its Main Components against Two Grain Storage Insects
Molecules 2010, 15(12), 9391-9402; doi:10.3390/molecules15129391
Received: 23 November 2010 / Revised: 10 December 2010 / Accepted: 17 December 2010 / Published: 20 December 2010
Cited by 42 | PDF Full-text (161 KB)
Abstract
During our screening program for agrochemicals from Chinese medicinal herbs and wild plants, the essential oil of Carum carvi fruits was found to possess strong contact toxicity against Sitophilus zeamais and Tribolium castaneum adults, with LD50 values of 3.07 and 3.29 mg/adult,
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During our screening program for agrochemicals from Chinese medicinal herbs and wild plants, the essential oil of Carum carvi fruits was found to possess strong contact toxicity against Sitophilus zeamais and Tribolium castaneum adults, with LD50 values of 3.07 and 3.29 mg/adult, respectively, and also showed strong fumigant toxicity against the two grain storage insects with LC50 values of 3.37 and 2.53 mg/L, respectively. The essential oil obtained by hydrodistillation was investigated by GC and GC-MS. The main components of the essential oil were identified to be (R)-carvone (37.98%) and D-limonene (26.55%) followed by α-pinene (5.21), cis-carveol (5.01%) and b-myrcene (4.67%). (R)-Carvone and D-limonene were separated and purified by silica gel column chromatography and preparative thin layer chromatography, and further identified by means of physicochemical and spectrometric analysis. (R)-Carvone and D-limonene showed strong contact toxicity against S. zeamais (LD50 = 2.79 and 29.86 mg/adult) and T. castaneum (LD50 = 2.64 and 20.14 mg/adult). (R)-Carvone and D-limonene also possessed strong fumigant toxicity against S. zeamais (LC50 = 2.76 and 48.18 mg/L) and T. castaneum adults (LC50 = 1.96 and 19.10 mg/L). Full article
Open AccessArticle Synthesis of 2-(4,6-Dimethoxy-1,3,5-triazin-2-yloxyimino) Derivatives: Application in Solution Peptide Synthesis
Molecules 2010, 15(12), 9403-9417; doi:10.3390/molecules15129403
Received: 29 November 2010 / Revised: 14 December 2010 / Accepted: 15 December 2010 / Published: 20 December 2010
Cited by 5 | PDF Full-text (158 KB)
Abstract
A new class of 1,3,5-triazinyloxyimino derivatives were prepared, characterized and tested for reactivity in solution peptide synthesis. The new triazinyloxyimino derivatives failed to activate the carboxyl group during formation of peptide bonds, but gave the corresponding N-triazinyl amino acid derivatives as a
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A new class of 1,3,5-triazinyloxyimino derivatives were prepared, characterized and tested for reactivity in solution peptide synthesis. The new triazinyloxyimino derivatives failed to activate the carboxyl group during formation of peptide bonds, but gave the corresponding N-triazinyl amino acid derivatives as a major product. The oxyma (ethyl 2-cyano-2-(hydroxyimino)acetate) uronium salt was superior to other uronium salts in terms of racemization, while 2-chloro-4,6-dimethoxy-1,3,5-triazine (CDMT, 9) gave the best results. Full article
Open AccessArticle Facile and Convenient Synthesis of New Thieno[2,3-b]-Thiophene Derivatives
Molecules 2010, 15(12), 9418-9426; doi:10.3390/molecules15129418
Received: 12 October 2010 / Revised: 15 December 2010 / Accepted: 16 December 2010 / Published: 20 December 2010
Cited by 23 | PDF Full-text (114 KB)
Abstract A facile and convenient synthesis of bis(2-(1H-benzo[d]imidazol-2(3H)-ylidene)-3-oxopropanenitrile), bis((3-amino-5-(methylthio)-1H-pyrazol-4-yl)methanone) and bis(2-thioxo-1,2-dihydropyrimidine-5-carbonitrile) derivatives incorporating a thieno- [2,3-b]thiophene moiety via versatile, readily accessible diethyl 3,4-dimethylthieno-[2,3-b]thiophene-2,5-dicarboxylate (1) is described. Full article
Open AccessArticle Synthesis and Antitumor Activity of 3-Methyl-4-oxo-3,4-dihydroimidazo [5,1-d][1,2,3,5]tetrazine-8-carboxylates and -carboxamides
Molecules 2010, 15(12), 9427-9436; doi:10.3390/molecules15129427
Received: 4 November 2010 / Revised: 10 December 2010 / Accepted: 14 December 2010 / Published: 20 December 2010
Cited by 2 | PDF Full-text (174 KB)
Abstract
Seventeen novel 3-methyl-4-oxo-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carboxylate and -carboxamide derivatives were synthesized and evaluated for their growth inhibition in seven human solid tumor and a human leukemia HL-60 cell lines. Compound IVa showed more activity than the other compounds and the positive control temozolomide. In
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Seventeen novel 3-methyl-4-oxo-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carboxylate and -carboxamide derivatives were synthesized and evaluated for their growth inhibition in seven human solid tumor and a human leukemia HL-60 cell lines. Compound IVa showed more activity than the other compounds and the positive control temozolomide. In the presence of 40 mg/mL of IVa, the survival rate of all tested tumor cells was less than 10%. Esters displayed more potent antitumour activity than amides and temozolomide against HL-60 cells. These compounds also exhibited considerably enhanced water-solubility. Full article
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Open AccessArticle Seasonal Variation in Total Phenolic and Flavonoid Contents and DPPH Scavenging Activity of Bellis perennis L. Flowers
Molecules 2010, 15(12), 9450-9461; doi:10.3390/molecules15129450
Received: 13 October 2010 / Revised: 14 December 2010 / Accepted: 20 December 2010 / Published: 21 December 2010
Cited by 27 | PDF Full-text (180 KB)
Abstract
Variations in total phenolic and flavonoid contents as well as antioxidant activity of Bellis perennis (common daisy) flowers were investigated. The flowers were collected monthly (from March to October, i.e., during the usual flowering season of the plant) at three localities in
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Variations in total phenolic and flavonoid contents as well as antioxidant activity of Bellis perennis (common daisy) flowers were investigated. The flowers were collected monthly (from March to October, i.e., during the usual flowering season of the plant) at three localities in three different years. Total flavonoids were determined spectrophotometrically by two methods: by formation of a complex with aluminium chloride after acidic hydrolysis of flower extracts (method 1) and by reaction with boric and oxalic acids in extracts without their modification (method 2). Total phenolics were determined spectrophotometrically using the Folin-Ciocalteu reagent. The antioxidant activity was determined spectrophotometrically by a 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging assay. The contents of flavonoids varied from 0.31 to 0.44 mg quercetin equivalent/100 mg dry weight (method 1) and from 1.37 to 2.20 mg pigenin-7-glucoside equivalent/100 mg dry weight (method 2). Total phenolics ranged from 2.81 to 3.57 mg gallic acid equivalent/100 mg dry weight. The antioxidant activity expressed as IC50 values varied from 66.03 to 89.27 µg/mL; it is about 50, 30, 20, and 10 times lower as compared with quercetin, ascorbic acid, Trolox®, and butylhydroxytoluene, respectively, and about five times higher in comparison with apigenin-7-glucoside. There is a significant correlation between antioxidant activity and total phenolics. No correlation between total flavonoid contents and antioxidant activity was observed. Contents of phenolics and flavonoids as well as antioxidant activity of daisy flowers vary to a relatively small extent during the year and are not dependant on the time of collection. Thus, the flowers possess comparable quality as to these characteristics over the whole flowering season of Bellis perennis. Effects of environmental factors on the amounts of secondary metabolites in plants are also discussed. Full article
(This article belongs to the Special Issue Phenolics and Polyphenolics)
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Open AccessArticle Aristolactams and Alkamides of Aristolochia gigantea
Molecules 2010, 15(12), 9462-9472; doi:10.3390/molecules15129462
Received: 24 November 2010 / Revised: 16 December 2010 / Accepted: 17 December 2010 / Published: 21 December 2010
Cited by 11 | PDF Full-text (159 KB)
Abstract
A new aristolactam, aristolactam 9-O-β-D-glucopyranosyl-(1→2)-β-D-glucoside, and two alkamides, N-cis- and N-trans-p-coumaroyl-3-O-methyldopamine, were isolated from stems of Aristolochia gigantea, together with the known compounds allantoin, E-nerolidol, β-sitosterol, (+)-kobusin, (+)-eudesmin, trans-N-feruloyltyramine, trans-
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A new aristolactam, aristolactam 9-O-β-D-glucopyranosyl-(1→2)-β-D-glucoside, and two alkamides, N-cis- and N-trans-p-coumaroyl-3-O-methyldopamine, were isolated from stems of Aristolochia gigantea, together with the known compounds allantoin, E-nerolidol, β-sitosterol, (+)-kobusin, (+)-eudesmin, trans-N-feruloyltyramine, trans-N-coumaroyltyramine, trans-N-feruloyl-3-O-methyldopamine, aristolactam Ia-N-β-D-glucoside, aristolactam Ia 8-β-D-glucoside, aristolactam IIIa, and magnoflorine. Their structures were determined by spectroscopic analyses. Full article
(This article belongs to the Section Natural Products)
Open AccessArticle A General Synthetic Procedure for 2-chloromethyl-4(3H)-quinazolinone Derivatives and Their Utilization in the Preparation of Novel Anticancer Agents with 4-Anilinoquinazoline Scaffolds
Molecules 2010, 15(12), 9473-9485; doi:10.3390/molecules15129473
Received: 27 October 2010 / Revised: 9 December 2010 / Accepted: 13 December 2010 / Published: 22 December 2010
Cited by 6 | PDF Full-text (507 KB)
Abstract
In our ongoing research on novel anticancer agents with 4-anilinoquinazoline scaffolds, a series of novel 2-chloromethyl-4(3H)-quinazolinones were needed as key intermediates. An improved one-step synthesis of 2-chloromethyl-4(3H)-quinazolinones utilizing o-anthranilic acids as starting materials was described. Based on it,
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In our ongoing research on novel anticancer agents with 4-anilinoquinazoline scaffolds, a series of novel 2-chloromethyl-4(3H)-quinazolinones were needed as key intermediates. An improved one-step synthesis of 2-chloromethyl-4(3H)-quinazolinones utilizing o-anthranilic acids as starting materials was described. Based on it, 2-hydroxy-methyl-4(3H)-quinazolinones were conveniently prepared in one pot. Moreover, two novel 4-anilinoquinazoline derivatives substituted with chloromethyl groups at the 2-position were synthesized and showed promising anticancer activity in vitro. Full article
Open AccessArticle Efficient Lewis Acid Ionic Liquid-Catalyzed Synthesis of the Key Intermediate of Coenzyme Q10 under Microwave Irradiation
Molecules 2010, 15(12), 9486-9495; doi:10.3390/molecules15129486
Received: 15 November 2010 / Revised: 13 December 2010 / Accepted: 20 December 2010 / Published: 22 December 2010
Cited by 10 | PDF Full-text (236 KB)
Abstract
An efficient synthesis of a valuable intermediate of coenzyme Q10 by microwave-assisted Lewis acidic ionic liquid (IL)-catalyzed Friedel-Crafts alkylation is reported. The acidity of six [Etpy]BF4-based ionic liquids was characterized by means of the FT-IR technique using acetonitrile as a
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An efficient synthesis of a valuable intermediate of coenzyme Q10 by microwave-assisted Lewis acidic ionic liquid (IL)-catalyzed Friedel-Crafts alkylation is reported. The acidity of six [Etpy]BF4-based ionic liquids was characterized by means of the FT-IR technique using acetonitrile as a molecular probe. The catalytic activities of these ionic liquids were correlated with their Lewis acidity. With increasing Lewis acid strength of the ionic liquids, their catalytic activity in the Friedel-Crafts reaction increased, except for [Etpy]BF4-AlCl3. The effects of the reaction system, the molar fraction of Lewis acid in the Lewis acid ILs and heating techniques were also investigated. Among the six Lewis acid ionic liquids tested [Etpy]BF4-ZnCl2 showed the best catalytic activity, with a yield of 89% after a very short reaction time (150 seconds). This procedure has the advantages of higher efficiency, better reusability of ILs, energy conservation and eco-friendliness. The method has practical value for preparation of CoQ10 on an industrial scale. Full article

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Open AccessReview Supramolecular Self-Assembled Chaos: Polyphenolic Lignin’s Barrier to Cost-Effective Lignocellulosic Biofuels
Molecules 2010, 15(12), 8641-8688; doi:10.3390/molecules15118641
Received: 15 October 2010 / Revised: 22 November 2010 / Accepted: 25 November 2010 / Published: 29 November 2010
Cited by 45 | PDF Full-text (552 KB)
Abstract
Phenylpropanoid metabolism yields a mixture of monolignols that undergo chaotic, non-enzymatic reactions such as free radical polymerization and spontaneous self-assembly in order to form the polyphenolic lignin which is a barrier to cost-effective lignocellulosic biofuels. Post-synthesis lignin integration into the plant cell wall
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Phenylpropanoid metabolism yields a mixture of monolignols that undergo chaotic, non-enzymatic reactions such as free radical polymerization and spontaneous self-assembly in order to form the polyphenolic lignin which is a barrier to cost-effective lignocellulosic biofuels. Post-synthesis lignin integration into the plant cell wall is unclear, including how the hydrophobic lignin incorporates into the wall in an initially hydrophilic milieu. Self-assembly, self-organization and aggregation give rise to a complex, 3D network of lignin that displays randomly branched topology and fractal properties. Attempts at isolating lignin, analogous to archaeology, are instantly destructive and non-representative of in planta. Lack of plant ligninases or enzymes that hydrolyze specific bonds in lignin-carbohydrate complexes (LCCs) also frustrate a better grasp of lignin. Supramolecular self-assembly, nano-mechanical properties of lignin-lignin, lignin-polysaccharide interactions and association-dissociation kinetics affect biomass deconstruction and thereby cost-effective biofuels production. Full article
(This article belongs to the Special Issue Phenolics and Polyphenolics)
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Open AccessReview Phenolic-Compound-Extraction Systems for Fruit and Vegetable Samples
Molecules 2010, 15(12), 8813-8826; doi:10.3390/molecules15128813
Received: 25 September 2010 / Revised: 22 November 2010 / Accepted: 29 November 2010 / Published: 3 December 2010
Cited by 102 | PDF Full-text (159 KB)
Abstract
This paper reviews the phenolic-compound-extraction systems used to analyse fruit and vegetable samples over the last 10 years. Phenolic compounds are naturally occurring antioxidants, usually found in fruits and vegetables. Sample preparation for analytical studies is necessary to determine the polyphenolic composition in
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This paper reviews the phenolic-compound-extraction systems used to analyse fruit and vegetable samples over the last 10 years. Phenolic compounds are naturally occurring antioxidants, usually found in fruits and vegetables. Sample preparation for analytical studies is necessary to determine the polyphenolic composition in these matrices. The most widely used extraction system is liquid-liquid extraction (LLE), which is an inexpensive method since it involves the use of organic solvents, but it requires long extraction times, giving rise to possible extract degradation. Likewise, solid-phase extraction (SPE) can be used in liquid samples. Modern techniques, which have been replacing conventional ones, include: supercritical fluid extraction (SFE), pressurized liquid extraction (PLE), microwave-assisted extraction (MAE) and ultrasound-assisted extraction (UAE). These alternative techniques reduce considerably the use of solvents and accelerate the extraction process. Full article
(This article belongs to the Special Issue Antioxidants)
Open AccessReview Thiol Signalling Network with an Eye to Diabetes
Molecules 2010, 15(12), 8890-8903; doi:10.3390/molecules15128890
Received: 24 October 2010 / Revised: 29 November 2010 / Accepted: 6 December 2010 / Published: 6 December 2010
Cited by 17 | PDF Full-text (139 KB)
Abstract
Redox regulatory system controls normal cellular functions. Controlled changes in redox couples potential serve as components for signal transduction, similarly to the phosphorylation cascade. Cellular redox biology requires both compartimentalisation and communication of redox systems: the thermodynamic disequilibrium of the major redox switches
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Redox regulatory system controls normal cellular functions. Controlled changes in redox couples potential serve as components for signal transduction, similarly to the phosphorylation cascade. Cellular redox biology requires both compartimentalisation and communication of redox systems: the thermodynamic disequilibrium of the major redox switches allows rapid and sensitive responses to perturbations in redox environments. The many oxidation states of sulphur are found in numerous sulphur species with distinct functional groups (thiols, disulphides, polysulphides, sulphenic, sulphinic and sulphonic acids, etc.), which participate in a complicated network of sulphur-based redox events. Human diseases such as diabetes mellitus and its cardiovascular complications have been associated with increased production of reactive oxygen species and perturbations of thiol redox homeostasis. The review surveys literature related to some etiopathogenic aspects and therapeutic perspectives. The dual toxic-protective property of sulphydryl-donor molecules in experimental settings proposes the general problem of designing antioxidants for therapeutic use. Full article
(This article belongs to the Special Issue Antioxidants)
Open AccessReview Phenolics and Plant Allelopathy
Molecules 2010, 15(12), 8933-8952; doi:10.3390/molecules15128933
Received: 19 September 2010 / Revised: 21 November 2010 / Accepted: 25 November 2010 / Published: 7 December 2010
Cited by 118 | PDF Full-text (318 KB)
Abstract
Phenolic compounds arise from the shikimic and acetic acid (polyketide) metabolic pathways in plants. They are but one category of the many secondary metabolites implicated in plant allelopathy. Phenolic allelochemicals have been observed in both natural and managed ecosystems, where they cause a
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Phenolic compounds arise from the shikimic and acetic acid (polyketide) metabolic pathways in plants. They are but one category of the many secondary metabolites implicated in plant allelopathy. Phenolic allelochemicals have been observed in both natural and managed ecosystems, where they cause a number of ecological and economic problems, such as declines in crop yield due to soil sickness, regeneration failure of natural forests, and replanting problems in orchards. Phenolic allelochemical structures and modes of action are diverse and may offer potential lead compounds for the development of future herbicides or pesticides. This article reviews allelopathic effects, analysis methods, and allelopathic mechanisms underlying the activity of plant phenolic compounds. Additionally, the currently debated topic in plant allelopathy of whether catechin and 8-hydroxyquinoline play an important role in Centaurea maculata and Centaurea diffusa invasion success is discussed. Overall, the main purpose of this review is to highlight the allelopacthic potential of phenolic compounds to provide us with methods to solve various ecology problems, especially in regard to the sustainable development of agriculture, forestry, nature resources and environment conservation. Full article
(This article belongs to the Section Natural Products)
Open AccessReview Development of Heterogeneous Olympic Medal Metal Nanoparticle Catalysts for Environmentally Benign Molecular Transformations Based on the Surface Properties of Hydrotalcite
Molecules 2010, 15(12), 8988-9007; doi:10.3390/molecules15128988
Received: 15 November 2010 / Revised: 29 November 2010 / Accepted: 7 December 2010 / Published: 8 December 2010
Cited by 27 | PDF Full-text (447 KB)
Abstract
In this review, we describe the development by our research group of highly functionalized heterogeneous Olympic medal metal (gold, silver, and copper) nanoparticle catalysts using hydrotalcite as a support, aimed towards Green and Sustainable Chemistry. Olympic medal metal nanoparticles can cooperate with the
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In this review, we describe the development by our research group of highly functionalized heterogeneous Olympic medal metal (gold, silver, and copper) nanoparticle catalysts using hydrotalcite as a support, aimed towards Green and Sustainable Chemistry. Olympic medal metal nanoparticles can cooperate with the basic sites on the hydrotalcite surface, providing unique and high performance catalysis in environmentally-benign organic transformations such as aerobic oxidation of alcohols, lactonization of diols and selective deoxygenation of epoxides and nitro aromatic compounds. Full article
(This article belongs to the Special Issue Bifunctional Catalysis)
Open AccessReview Biosynthesis of Anthocyanins and Their Regulation in Colored Grapes
Molecules 2010, 15(12), 9057-9091; doi:10.3390/molecules15129057
Received: 19 October 2010 / Accepted: 7 December 2010 / Published: 9 December 2010
Cited by 126 | PDF Full-text (504 KB)
Abstract
Anthocyanins, synthesized via the flavonoid pathway, are a class of crucial phenolic compounds which are fundamentally responsible for the red color of grapes and wines. As the most important natural colorants in grapes and their products, anthocyanins are also widely studied for their
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Anthocyanins, synthesized via the flavonoid pathway, are a class of crucial phenolic compounds which are fundamentally responsible for the red color of grapes and wines. As the most important natural colorants in grapes and their products, anthocyanins are also widely studied for their numerous beneficial effects on human health. In recent years, the biosynthetic pathway of anthocyanins in grapes has been thoroughly investigated. Their intracellular transportation and accumulation have also been further clarified. Additionally, the genetic mechanism regulating their biosynthesis and the phytohormone influences on them are better understood. Furthermore, due to their importance in the quality of wine grapes, the effects of the environmental factors and viticulture practices on anthocyanin accumulation are being investigated increasingly. The present paper summarizes both the basic information and the most recent advances in the study of the anthocyanin biosynthesis in red grapes, emphasizing their gene structure, the transcriptional factors and the diverse exterior regulation factors. Full article
(This article belongs to the Special Issue Phenolics and Polyphenolics)
Open AccessReview Experimental Models for Assaying Microvascular Endothelial Cell Pathophysiology in Stroke
Molecules 2010, 15(12), 9104-9134; doi:10.3390/molecules15129104
Received: 29 October 2010 / Revised: 29 November 2010 / Accepted: 8 December 2010 / Published: 10 December 2010
Cited by 11 | PDF Full-text (207 KB)
Abstract
It is important to understand the molecular mechanisms underlying neuron death following stroke in order to develop effective neuroprotective strategies. Since studies on human stroke are extremely limited due to the difficulty in collecting post-mortem tissue at different time points after the onset
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It is important to understand the molecular mechanisms underlying neuron death following stroke in order to develop effective neuroprotective strategies. Since studies on human stroke are extremely limited due to the difficulty in collecting post-mortem tissue at different time points after the onset of stroke, brain ischaemia research focuses on information derived from in-vitro models of neuronal death through ischaemic injury [1]. This review aims to provide an update on the different in-vitro stroke models with brain microvascular endothelial cells that are currently being used. These models provide a physiologically relevant tool to screen potential neuroprotective drugs in stroke and to study the molecular mechanisms involved in brain ischaemia. Full article
(This article belongs to the Special Issue Neuroprotective Strategies)
Open AccessReview [2+2+2] Cycloaddition Reactions of Macrocyclic Systems Catalyzed by Transition Metals. A Review
Molecules 2010, 15(12), 9230-9251; doi:10.3390/molecules15129230
Received: 24 November 2010 / Revised: 10 December 2010 / Accepted: 14 December 2010 / Published: 15 December 2010
Cited by 29 | PDF Full-text (224 KB)
Abstract
Polyalkyne and enediyne azamacrocycles are prepared from arenesulfonamides and various alkyne and alkene derivatives either under basic or neutral conditions. The new family of macrocyclic substrates is tested in the [2+2+2] cycloaddition reaction. Several catalysts are used for the cycloisomerization reaction, and their
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Polyalkyne and enediyne azamacrocycles are prepared from arenesulfonamides and various alkyne and alkene derivatives either under basic or neutral conditions. The new family of macrocyclic substrates is tested in the [2+2+2] cycloaddition reaction. Several catalysts are used for the cycloisomerization reaction, and their enantioinduction is evaluated as appropriate. The effect of the structural features of the macrocycles, namely the ring size, substituents in precise positions and the number and type of unsaturations, on the [2+2+2] cycloaddition reaction has also been studied. Full article
(This article belongs to the Special Issue Cycloaddition Reactions in Organic Synthesis)
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Open AccessReview Antioxidant and Anti-Inflammatory Activities of Essential Oils: A Short Review
Molecules 2010, 15(12), 9252-9287; doi:10.3390/molecules15129252
Received: 2 December 2010 / Revised: 9 December 2010 / Accepted: 13 December 2010 / Published: 15 December 2010
Cited by 147 | PDF Full-text (311 KB)
Abstract
Essential oils are complex mixtures isolated from aromatic plants which may possess antioxidant and anti-inflammatory activities of interest in thye food and cosmetic industries as well as in the human health field. In this work, a review was done on the most recent
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Essential oils are complex mixtures isolated from aromatic plants which may possess antioxidant and anti-inflammatory activities of interest in thye food and cosmetic industries as well as in the human health field. In this work, a review was done on the most recent publications concerning their antioxidant and anti-inflammatory activities. At the same time a survey of the methods generally used for the evaluation of antioxidant activity and some of the mechanisms involved in the anti-inflammatory activities of essential oils are also reported. Full article
Open AccessReview Application of Cycloaddition Reactions to the Syntheses of Novel Boron Compounds
Molecules 2010, 15(12), 9437-9449; doi:10.3390/molecules15129437
Received: 11 October 2010 / Revised: 16 December 2010 / Accepted: 20 December 2010 / Published: 21 December 2010
Cited by 3 | PDF Full-text (708 KB)
Abstract
This review covers the application of cycloaddition reactions in forming the boron-containing compounds such as symmetric star-shaped boron-enriched dendritic molecules, nano-structured boron materials and aromatic boronic esters. The resulting boron compounds are potentially important reagents for both materials science and medical applications such
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This review covers the application of cycloaddition reactions in forming the boron-containing compounds such as symmetric star-shaped boron-enriched dendritic molecules, nano-structured boron materials and aromatic boronic esters. The resulting boron compounds are potentially important reagents for both materials science and medical applications such as in boron neutron capture therapy (BNCT) in cancer treatment and as drug delivery agents and synthetic intermediates for carbon-carbon cross-coupling reactions. In addition, the use of boron cage compounds in a number of cycloaddition reactions to synthesize unique aromatic species will be reviewed briefly. Full article
(This article belongs to the Special Issue Cycloaddition Reactions in Organic Synthesis)
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