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Molecules, Volume 17, Issue 7 (July 2012), Pages 7612-8734

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Open AccessArticle Terpene Glycosides from the Roots of Sanguisorba officinalis L. and Their Hemostatic Activities
Molecules 2012, 17(7), 7629-7636; doi:10.3390/molecules17077629
Received: 15 May 2012 / Revised: 13 June 2012 / Accepted: 15 June 2012 / Published: 25 June 2012
Cited by 11 | PDF Full-text (208 KB)
Abstract
Guided by a hemostasis bioassay, seven terpene glycosides were isolated from the roots of Sanguisorba officinalis L. by silica gel column chromatography and preparative HPLC. On the grounds of chemical and spectroscopic methods, their structures were identified as citronellol-1-O-α-l-arabinofuranosyl-(1→6)-β-d-glucopyranoside (1
[...] Read more.
Guided by a hemostasis bioassay, seven terpene glycosides were isolated from the roots of Sanguisorba officinalis L. by silica gel column chromatography and preparative HPLC. On the grounds of chemical and spectroscopic methods, their structures were identified as citronellol-1-O-α-l-arabinofuranosyl-(1→6)-β-d-glucopyranoside (1), geraniol-1-O-α-l-arabinofuranosyl-(1→6)-β-d-glucopyranoside (2), geraniol-1-O-α-l-arabinopyranosyl-(1→6)-β-d-glucopyranoside (3), 3β-[(α-l-arabinopyranosyl)oxy]-19α-hydroxyolean-12-en-28-oic acid 28-β-d-glucopyranoside (4), 3β-[(α-l-arabinopyranosyl)-oxy]-19α-hydroxyurs-12-en-28-oic acid 28-β-d-glucopyranoside (ziyu-glycoside I, 5), 3β,19α-hydroxyolean-12-en-28-oic acid 28-β-d-glucopyranoside (6) and 3β,19α-di-hydroxyurs-12-en-28-oic acid 28-β-d-glucopyranoside (7). Compound 1 is a new mono-terpene glycoside and compounds 2, 3 and 5 were isolated from the Sanguisorba genus for the first time. Compounds 17 were assayed for their hemostatic activities with a Goat Anti-Human α2-plasmin inhibitor ELISA kit, and ziyu-glycoside I (5) showed the strongest hemostatic activity among the seven terpene glycosides. This is the first report that ziyu-glycoside Ι has strong hemostatic activity. Full article
Open AccessArticle A New Benzofuran Derivative from Flemingia philippinensis Merr. et Rolfe
Molecules 2012, 17(7), 7637-7644; doi:10.3390/molecules17077637
Received: 16 April 2012 / Revised: 31 May 2012 / Accepted: 5 June 2012 / Published: 25 June 2012
Cited by 3 | PDF Full-text (233 KB) | Supplementary Files
Abstract
A new prenylated benzofuran derivative, named flemiphilippinone A, was isolated together with ten known flavonoids from the roots of Flemingia philippinensis. Flemiphilippinone A was identified as (2S,3aS)-5-(1-hydroxy-3-(4-methoxyphenyl)- propylidene)-2-(2-hydroxypropan-2-yl)-3a,7-bis(3-methylbut-2-en-1-yl)tetrahydrobenzo- furan-4,6(2H,5H)-dione, and its structure was established
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A new prenylated benzofuran derivative, named flemiphilippinone A, was isolated together with ten known flavonoids from the roots of Flemingia philippinensis. Flemiphilippinone A was identified as (2S,3aS)-5-(1-hydroxy-3-(4-methoxyphenyl)- propylidene)-2-(2-hydroxypropan-2-yl)-3a,7-bis(3-methylbut-2-en-1-yl)tetrahydrobenzo- furan-4,6(2H,5H)-dione, and its structure was established by a combination of HR EIMS, 1H-NMR, 13C-NMR, HMQC, HMBC and NOESY spectra data. Full article
(This article belongs to the Section Natural Products)
Open AccessArticle Butylated Hydroxytoluene Analogs: Synthesis and Evaluation of Their Multipotent Antioxidant Activities
Molecules 2012, 17(7), 7645-7665; doi:10.3390/molecules17077645
Received: 9 April 2012 / Revised: 1 June 2012 / Accepted: 12 June 2012 / Published: 25 June 2012
Cited by 14 | PDF Full-text (365 KB)
Abstract
A computer-aided predictions of antioxidant activities were performed with the Prediction Activity Spectra of Substances (PASS) program. Antioxidant activity of compounds 1, 3, 4 and 5 were studied using 1,1-diphenyl-2-picrylhydrazyl (DPPH) and lipid peroxidation assays to verify the predictions obtained by
[...] Read more.
A computer-aided predictions of antioxidant activities were performed with the Prediction Activity Spectra of Substances (PASS) program. Antioxidant activity of compounds 1, 3, 4 and 5 were studied using 1,1-diphenyl-2-picrylhydrazyl (DPPH) and lipid peroxidation assays to verify the predictions obtained by the PASS program. Compounds 3 and 5 showed more inhibition of DPPH stable free radical at 10−4 M than the well-known standard antioxidant, butylated hydroxytoluene (BHT). Compound 5 exhibited promising in vitro inhibition of Fe2+-induced lipid peroxidation of the essential egg yolk as a lipid-rich medium (83.99%, IC50 16.07 ± 3.51 µM/mL) compared to a-tocopherol (a-TOH, 84.6%, IC50 5.6 ± 1.09 µM/mL). The parameters for drug-likeness of these BHT analogues were also evaluated according to the Lipinski’s “rule-of-five” (RO5). All the BHT analogues were found to violate one of the Lipinski’s parameters (LogP > 5), even though they have been found to be soluble in protic solvents. The predictive polar surface area (PSA) and absorption percent (% ABS) data allow us to conclude that they could have a good capacity for penetrating cell membranes. Therefore, one can propose these new multipotent antioxidants (MPAOs) as potential antioxidants for tackling oxidative stress and lipid peroxidation processes. Full article
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Open AccessArticle Residue-Ligand Interaction Energy (ReLIE) on a Receptor-Dependent 3D-QSAR Analysis of S- and NH-DABOs as Non-Nucleoside Reverse Transcriptase Inhibitors
Molecules 2012, 17(7), 7666-7694; doi:10.3390/molecules17077666
Received: 7 May 2012 / Revised: 2 June 2012 / Accepted: 5 June 2012 / Published: 25 June 2012
Cited by 6 | PDF Full-text (820 KB)
Abstract
A series of 74 dihydroalkoxybenzyloxopyrimidines (DABOs), a class of highly potent non-nucleoside reverse transcriptase inhibitors (NNRTIs), was retrieved from the literature and studied by receptor-dependent (RD) three-dimensional quantitative structure-activity relationship (3D-QSAR) analysis to derive RD-3D-QSAR models. The descriptors in this new method are
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A series of 74 dihydroalkoxybenzyloxopyrimidines (DABOs), a class of highly potent non-nucleoside reverse transcriptase inhibitors (NNRTIs), was retrieved from the literature and studied by receptor-dependent (RD) three-dimensional quantitative structure-activity relationship (3D-QSAR) analysis to derive RD-3D-QSAR models. The descriptors in this new method are the steric and electrostatic interaction energies of the protein-ligand complexes (per residue) simulated by molecular dynamics, an approach named Residue-Ligand Interaction Energy (ReLIE). This study was performed using a training set of 59 compounds and the MKC-442/RT complex structure as reference. The ReLIE-3D-QSAR models were constructed and evaluated by genetic algorithm (GA) and partial least squares (PLS). In the best equations, at least one term is related to one of the amino acid residues of the p51 subunit: Asn136, Asn137, Glu138, and Thr139. This fact implies the importance of interchain interaction (p66-p51) in the equations that best describe the structure-activity relationship for this class of compounds. The best equation shows q2 = 0.660, SEcv = 0.500, r2 = 0.930, and SEE = 0.226. The external predictive ability of this best model was evaluated using a test set of 15 compounds. In order to design more potent DABO analogues as anti-HIV/AIDS agents, substituents capable of interactions with residues like Ile94, Lys101, Tyr181, and Tyr188 should be selected. Also, given the importance of the conserved Asn136, this residue could become an attractive target for the design of novel NNRTIs with improved potency and increased ability to avoid the development of drug-resistant viruses. Full article
(This article belongs to the Section Medicinal Chemistry)
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Open AccessArticle Restoration of Electric Footshock-Induced Immunosuppression in Mice by Gynostemma pentaphyllum Components
Molecules 2012, 17(7), 7695-7708; doi:10.3390/molecules17077695
Received: 17 February 2012 / Revised: 11 June 2012 / Accepted: 20 June 2012 / Published: 25 June 2012
Cited by 7 | PDF Full-text (353 KB)
Abstract
The immunomodulatory effects of the ethanol extract of Gynostemma pentaphyllum (GP-EX) were examined in electric footshock (EFS)-stressed mice. The mice were orally administered various doses of GP-EX for 7 days before exposure to EFS (duration: 3 min, interval: 10 s, intensity: 2 mA)
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The immunomodulatory effects of the ethanol extract of Gynostemma pentaphyllum (GP-EX) were examined in electric footshock (EFS)-stressed mice. The mice were orally administered various doses of GP-EX for 7 days before exposure to EFS (duration: 3 min, interval: 10 s, intensity: 2 mA) once a day from day 8 for 14 days with continuous daily feeding of GP-EX. Oral administration of GP-EX to mice prevented EFS stress-induced immunosuppression as determined by the lymphoid organ (thymus and spleen) weight and cellularity. In addition, oral administration of GP-EX restored EFS-suppressed functional properties of mature lymphocytes in terms of concanavalin A-induced proliferation of splenocytes and lipopolysaccharide-induced cytokine production (TNF-α, IL-1β). Furthermore, we found that mice that were orally administered with GP-EX generated much more potent ovalbumin-specific cytotoxic T lymphocyte responses upon intravenous ovalbumin injection compared to the untreated controls. These results demonstrate that oral administration of the ethanol extract of Gynostemma pentaphyllum could increase host defense in immunocompromised situations such as stress-induced immunosuppression. Full article
Open AccessArticle A Further Contribution to the Study of Sagittamide A: Synthesis of a Pivotal Intermediate Belonging to a Rare L-Series
Molecules 2012, 17(7), 7709-7721; doi:10.3390/molecules17077709
Received: 3 May 2012 / Revised: 13 June 2012 / Accepted: 18 June 2012 / Published: 25 June 2012
PDF Full-text (477 KB)
Abstract A key saggitamide intermediate corresponding to a rare sugar framework has been obtained. This approach should help to establish the overall configuration of more complex structures of the sagittamide family. Full article
(This article belongs to the Special Issue Stereoselective Synthesis)
Open AccessArticle In Situ Electrochemical SFG/DFG Study of CN and Nitrile Adsorption at Au from 1-Butyl-1-methyl-pyrrolidinium Bis(trifluoromethylsulfonyl) Amide Ionic Liquid ([BMP][TFSA]) Containing 4-{2-[1-(2-Cyanoethyl)-1,2,3,4-tetrahydroquinolin-6-yl]diazenyl} Benzonitrile (CTDB) and K[Au(CN)2]
Molecules 2012, 17(7), 7722-7736; doi:10.3390/molecules17077722
Received: 21 March 2012 / Revised: 22 May 2012 / Accepted: 23 May 2012 / Published: 25 June 2012
Cited by 3 | PDF Full-text (638 KB)
Abstract
In this paper we report an in situ electrochemical Sum-/Difference Frequency Generation (SFG/DFG) spectroscopy investigation of the adsorption of nitrile and CN from the ionic liquid 1-butyl-1-methyl-pyrrolidinium bis(trifluoromethylsulfonyl) amide ([BMP][TFSA]) containing 4-{2-[1-(2-cyanoethyl)-1,2,3,4-tetrahydroquinolin-6-yl]- diazenyl}benzonitrile (CTDB) at Au electrodes in the absence and in
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In this paper we report an in situ electrochemical Sum-/Difference Frequency Generation (SFG/DFG) spectroscopy investigation of the adsorption of nitrile and CN from the ionic liquid 1-butyl-1-methyl-pyrrolidinium bis(trifluoromethylsulfonyl) amide ([BMP][TFSA]) containing 4-{2-[1-(2-cyanoethyl)-1,2,3,4-tetrahydroquinolin-6-yl]- diazenyl}benzonitrile (CTDB) at Au electrodes in the absence and in the presence of the Au-electrodeposition process from K[Au(CN)2]. The adsorption of nitrile and its coadsorption with CN resulting either from the cathodic decomposition of the dye or from ligand release from the Au(I) cyanocomplex yield potential-dependent single or double SFG bands in the range 2,125–2,140 cm1, exhibiting Stark tuning values of ca. 3 and 1 cm1 V1 in the absence and presence of electrodeposition, respectively. The low Stark tuning found during electrodeposition correlates with the cathodic inhibiting effect of CTDB, giving rise to its levelling properties. The essential insensitivity of the other DFG parameters to the electrodeposition process is due to the growth of smooth Au. Full article
(This article belongs to the Special Issue Ionic Liquids)
Open AccessArticle New Quinoxaline Derivatives as Potential MT1 and MT2 Receptor Ligands
Molecules 2012, 17(7), 7737-7757; doi:10.3390/molecules17077737
Received: 17 April 2012 / Revised: 14 June 2012 / Accepted: 18 June 2012 / Published: 25 June 2012
Cited by 6 | PDF Full-text (500 KB)
Abstract
Ever since the idea arose that melatonin might promote sleep and resynchronize circadian rhythms, many research groups have centered their efforts on obtaining new melatonin receptor ligands whose pharmacophores include an aliphatic chain of variable length united to an N-alkylamide and a
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Ever since the idea arose that melatonin might promote sleep and resynchronize circadian rhythms, many research groups have centered their efforts on obtaining new melatonin receptor ligands whose pharmacophores include an aliphatic chain of variable length united to an N-alkylamide and a methoxy group (or a bioisostere), linked to a central ring. Substitution of the indole ring found in melatonin with a naphthalene or quinoline ring leads to compounds of similar affinity. The next step in this structural approximation is to introduce a quinoxaline ring (a bioisostere of the quinoline and naphthalene rings) as the central nucleus of future melatoninergic ligands. Full article
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Open AccessArticle Characterization of the Antibacterial Activity and the Chemical Components of the Volatile Oil of the Leaves of Rubus parvifolius L.
Molecules 2012, 17(7), 7758-7768; doi:10.3390/molecules17077758
Received: 9 May 2012 / Revised: 15 June 2012 / Accepted: 19 June 2012 / Published: 25 June 2012
Cited by 4 | PDF Full-text (1522 KB)
Abstract
Rubus parvifolius L. (Rp) is a medicinal herb that possesses antibacterial activity. In this study, we extracted the volatile oil from the leaves of Rp to assess its antibacterial activity and analyze its chemical composition. A uniform distribution design was used to optimize
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Rubus parvifolius L. (Rp) is a medicinal herb that possesses antibacterial activity. In this study, we extracted the volatile oil from the leaves of Rp to assess its antibacterial activity and analyze its chemical composition. A uniform distribution design was used to optimize the extraction procedure, which yielded 0.36% (w/w) of light yellowish oil from the water extract of Rp leaves. We found that the extracted oil effectively inhibited the growth of a wide range of Gram positive and negative bacteria, including Staphylococcus aureus, Staphylococcus epidermidis, Enterococcus faecalis, Escherichia coli, Pseudomonas aeruginosa, Acinetobacter baumanii, Bacillus cloacae, and Klebsiella pneumoniae. We further analyzed the components contained in the hydro-distillated Rp volatile oil by gas chromatography-mass spectroscopy. Twenty nine compounds were identified, including 4-hydroxy-3-methoxystyrene (66%), 3,7,11,15-tetramethyl-2-hexadecen-1-ol (10%) and 4-tert-butylbenzoic acid (2%). Our results suggest that one or multiple constituents contained in Rp volatile oil may account for its antibacterial activity. Full article
(This article belongs to the Section Natural Products)
Open AccessArticle B-norsteroids from Hymenoscyphus pseudoalbidus
Molecules 2012, 17(7), 7769-7781; doi:10.3390/molecules17077769
Received: 5 June 2012 / Revised: 13 June 2012 / Accepted: 15 June 2012 / Published: 25 June 2012
Cited by 10 | PDF Full-text (669 KB)
Abstract
Two viridin-related B-norsteroids, B-norviridiol lactone (1) and B-norviridin enol (2), both possessing distinct unprecedented carbon skeletons, were isolated from a liquid culture of the ash dieback-causing fungus Hymenoscyphus pseudoalbidus. Compound 2 was found to degrade to a third
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Two viridin-related B-norsteroids, B-norviridiol lactone (1) and B-norviridin enol (2), both possessing distinct unprecedented carbon skeletons, were isolated from a liquid culture of the ash dieback-causing fungus Hymenoscyphus pseudoalbidus. Compound 2 was found to degrade to a third B-norsteroidal compound, 1β-hydroxy-2α-hydro-asterogynin A (3), which was later detected in the original culture. The proposed structure of 1 is, regarding connectivity, identical to the original erroneous structure for TAEMC161, which was later reassigned as viridiol. Compound 2 showed an unprecedented 1H-13C HMBC correlation through an intramolecular hydrogen bond. The five-membered B-ring of compounds 1–3 was proposed to be formed by a benzilic acid rearrangement. The known compound asterogynin A was found to be formed from 3 by a β-elimination of water. All compounds were characterized by NMR spectroscopy, LC-HRMS and polarimetry. Full article
(This article belongs to the Section Natural Products)
Open AccessArticle Genotoxicity of Euphorbia hirta: An Allium cepa Assay
Molecules 2012, 17(7), 7782-7791; doi:10.3390/molecules17077782
Received: 23 April 2012 / Revised: 20 June 2012 / Accepted: 21 June 2012 / Published: 26 June 2012
Cited by 19 | PDF Full-text (444 KB)
Abstract
The potential genotoxic effects of methanolic extracts of Euphorbia hirta which is commonly used in traditional medicine to treat a variety of diseased conditions including asthma, coughs, diarrhea and dysentery was investigated using Allium cepa assay. The extracts of 125, 250, 500 and
[...] Read more.
The potential genotoxic effects of methanolic extracts of Euphorbia hirta which is commonly used in traditional medicine to treat a variety of diseased conditions including asthma, coughs, diarrhea and dysentery was investigated using Allium cepa assay. The extracts of 125, 250, 500 and 1,000 µg/mL were tested on root meristems of A. cepa. Ethylmethanesulfonate was used as positive control and distilled water was used as negative control. The result showed that mitotic index decreased as the concentrations of E. hirta extract increased. A dose-dependent increase of chromosome aberrations was also observed. Abnormalities scored were stickiness, c-mitosis, bridges and vagrant chromosomes. Micronucleated cells were also observed at interphase. Result of this study confirmed that the methanol extracts of E. hirta exerted significant genotoxic and mitodepressive effects at 1,000 µg/mL. Full article
(This article belongs to the Section Natural Products)
Open AccessArticle Sikokianin D, A New C-3/C-3"-Biflavanone from the Roots of Wikstroemia indica
Molecules 2012, 17(7), 7792-7797; doi:10.3390/molecules17077792
Received: 28 April 2012 / Revised: 15 June 2012 / Accepted: 19 June 2012 / Published: 26 June 2012
Cited by 3 | PDF Full-text (188 KB)
Abstract A new 3,3′′-biflavanone, sikokianin D (1), was isolated from the roots of Wikstroemia indica, together with two known compounds. Their structures were elucidated by chemical evidence and spectral analyses, including HR-ESI-MS, and 1D- and 2D-NMR techniques. Full article
(This article belongs to the Section Natural Products)
Open AccessArticle Industrial-Scale Preparation of Akebia Saponin D by a Two-Step Macroporous Resin Column Separation
Molecules 2012, 17(7), 7798-7809; doi:10.3390/molecules17077798
Received: 13 April 2012 / Revised: 13 June 2012 / Accepted: 21 June 2012 / Published: 26 June 2012
Cited by 1 | PDF Full-text (249 KB)
Abstract
A simple and efficient procedure for the industrial preparation of akebia saponin D, one of the bioactive compounds commonly found in the well-known Chinese Medicinal herb Dipsaci Radix, was developed. First, HPD-722 was selected from among 10 kinds of macroporous absorption resins.
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A simple and efficient procedure for the industrial preparation of akebia saponin D, one of the bioactive compounds commonly found in the well-known Chinese Medicinal herb Dipsaci Radix, was developed. First, HPD-722 was selected from among 10 kinds of macroporous absorption resins. Following this step, the purity of akebia saponin D was increased about 10 times from 6.27% to 59.41%. In order to achieve a higher purity, ADS-7 was chosen from among five kinds of macroporous absorption resins, and the purity of akebia saponin D was increased from 59.41% to 95.05%. The result indicated HPD-722 and ADS-7 were the most suitable resins to purify akebia saponin D from Dipsaci Radix. Under these conditions, large-scale preparation of akebia saponin D was carried out successfully. The preparation method is simple, efficient, and has been demonstrated to be effective for large scale preparations of akebia saponin D from Dipsaci Radix. Full article
(This article belongs to the Section Natural Products)
Open AccessArticle Molecular Cloning, Characterization and Expression of the Phenylalanine Ammonia-Lyase Gene from Juglans regia
Molecules 2012, 17(7), 7810-7823; doi:10.3390/molecules17077810
Received: 29 May 2012 / Revised: 11 June 2012 / Accepted: 11 June 2012 / Published: 26 June 2012
Cited by 15 | PDF Full-text (629 KB)
Abstract
Phenylalanine ammonia-lyase (PAL) is the first key enzyme of the phenypropanoid pathway. A full-length cDNA of PAL gene was isolated from Juglans regia for the first time, and designated as JrPAL. The full-length cDNA of the JrPAL gene contained a 1935bp open
[...] Read more.
Phenylalanine ammonia-lyase (PAL) is the first key enzyme of the phenypropanoid pathway. A full-length cDNA of PAL gene was isolated from Juglans regia for the first time, and designated as JrPAL. The full-length cDNA of the JrPAL gene contained a 1935bp open reading frame encoding a 645-amino-acid protein with a calculated molecular weight of about 70.4 kD and isoelectric point (pI) of 6.7. The deduced JrPAL protein showed high identities with other plant PALs. Molecular modeling of JrPAL showed that the 3D model of JrPAL was similar to that of PAL protein from Petroselinum crispum (PcPAL), implying that JrPAL may have similar functions with PcPAL. Phylogenetic tree analysis revealed that JrPAL shared the same evolutionary ancestor of other PALs and had a closer relationship with other angiosperm species. Transcription analysis revealed that JrPAL was expressed in all tested tissues including roots, stems, and leaves, with the highest transcription level being found in roots. Expression profiling analyses by real-time PCR revealed that JrPAL expression was induced by a variety of abiotic and biotic stresses, including UV-B, wounding, cold, abscisic acid and salicylic acid. Full article
Open AccessArticle Self Assembled Films of Porphyrins with Amine Groups at Different Positions: Influence of Their Orientation on the Corrosion Inhibition and the Electrocatalytic Activity
Molecules 2012, 17(7), 7824-7842; doi:10.3390/molecules17077824
Received: 28 April 2012 / Revised: 8 June 2012 / Accepted: 12 June 2012 / Published: 26 June 2012
Cited by 12 | PDF Full-text (605 KB)
Abstract
Self-assembled molecular films of two cobalt porphyrins with amine groups at different positions—(5,10,15,20-tetrakis-(2-aminophenyl) porphyrin-cobalt(II), [Co(II) (T(o-NH2)PP)] and (5,10,15,20-tetrakis-(4-aminophenyl) porphyrin-cobalt(II), [Co(II)(T(p-NH2)PP)]—were formed on a gold substrate. The functionalized surfaces were characterized using Raman spectroscopy, atomic force microscopy and electrochemical methods.
[...] Read more.
Self-assembled molecular films of two cobalt porphyrins with amine groups at different positions—(5,10,15,20-tetrakis-(2-aminophenyl) porphyrin-cobalt(II), [Co(II) (T(o-NH2)PP)] and (5,10,15,20-tetrakis-(4-aminophenyl) porphyrin-cobalt(II), [Co(II)(T(p-NH2)PP)]—were formed on a gold substrate. The functionalized surfaces were characterized using Raman spectroscopy, atomic force microscopy and electrochemical methods. Both modified gold surfaces completely mask the charge transfer of a [Fe(CN)6]3−/4− redox couple in solution, indicating the layer is highly resistive in behavior. Electrochemical impedance spectroscopy analyses revealed that the porphyrin film with amine groups at ortho positions shows a higher charge-transfer resistance with a better protective behavior compared to the para position modified surface. Raman, AFM and EIS data suggests that an ortho amine positioned molecule forms a more compact layer compared to the para-positioned molecule. This can be explained in terms of their orientation on the gold surface. [Co(II)(T(o-NH2)PP)] adopted a saddle shape orientation whereas [Co(II)(T(p-NH2)PP)] adopted a flat orientation on the gold surface. The porphyrin modified gold electrode catalyzes the oxygen reduction at lower potentials compared to the bare gold electrode. The shift in the overvoltage was higher in case of molecules with flat orientation compared to the saddle shaped oriented porphyrin molecules on the surface. Full article
(This article belongs to the Special Issue Tetrapyrroles, Porphyrins and Phthalocyanines)
Open AccessArticle Nitrate, Ascorbic Acid, Mineral and Antioxidant Activities of Cosmos caudatus in Response to Organic and Mineral-Based Fertilizer Rates
Molecules 2012, 17(7), 7843-7853; doi:10.3390/molecules17077843
Received: 2 May 2012 / Revised: 29 May 2012 / Accepted: 18 June 2012 / Published: 28 June 2012
Cited by 4 | PDF Full-text (268 KB)
Abstract
The source and quantity of nutrients available to plants can affect the quality of leafy herbs. A study was conducted to compare quality of Cosmos caudatus in response to rates of organic and mineral-based fertilizers. Organic based fertilizer GOBI (8% N:8% P2
[...] Read more.
The source and quantity of nutrients available to plants can affect the quality of leafy herbs. A study was conducted to compare quality of Cosmos caudatus in response to rates of organic and mineral-based fertilizers. Organic based fertilizer GOBI (8% N:8% P2O5:8% K2O) and inorganic fertilizer (15% N, 15% P2O5, 15% K2O) were evaluated based on N element rates at 0, 30, 60, 90, 120 kg h−1. Application of organic based fertilizer reduced nitrate, improved vitamin C, antioxidant activity as well as nitrogen and calcium nutrients content. Antioxidant activity and chlorophyll content were significantly higher with increased fertilizer application. Fertilization appeared to enhance vitamin C content, however for the maximum ascorbic acid content, regardless of fertilizer sources, plants did not require high amounts of fertilizer. Full article
Open AccessArticle Biochemical Characterization of an In-House Coccidioides Antigen: Perspectives for the Immunodiagnosis of Coccidioidomycosis
Molecules 2012, 17(7), 7854-7863; doi:10.3390/molecules17077854
Received: 23 March 2012 / Revised: 18 June 2012 / Accepted: 20 June 2012 / Published: 28 June 2012
PDF Full-text (192 KB)
Abstract
The objective of this study was to evaluate the reactivity of an in-house antigen, extracted from a strain of C. posadasii isolated in northeastern Brazil, by radial immunodiffusion and Western blotting, as well as to establish its biochemical characterization. The protein antigen was
[...] Read more.
The objective of this study was to evaluate the reactivity of an in-house antigen, extracted from a strain of C. posadasii isolated in northeastern Brazil, by radial immunodiffusion and Western blotting, as well as to establish its biochemical characterization. The protein antigen was initially extracted with the use of solid ammonium sulfate and characterized by 1-D electrophoresis. Subsequently, it was tested by means of double radial immunodiffusion and Western blotting. A positive reaction was observed against the antigen by both immunodiagnostic techniques tested on sera from patients suffering from coccidioidomycosis. Besides this, two immunoreactive protein bands were observed and were revealed to be a β-glucosidase and a glutamine synthetase after sequencing of the respective N-terminal regions. Our in-house Coccidioides antigen can be promising as a quick and low-cost diagnostic tool without the risk of direct manipulation of the microorganism. Full article
(This article belongs to the Section Medicinal Chemistry)
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Open AccessArticle Tebrophen — An Old Polyphenol Drug with Anticancer Potential
Molecules 2012, 17(7), 7864-7886; doi:10.3390/molecules17077864
Received: 26 March 2012 / Revised: 8 June 2012 / Accepted: 14 June 2012 / Published: 28 June 2012
Cited by 1 | PDF Full-text (1983 KB)
Abstract
In vitro high-throughput screening was carried out in order to detect new activities for old drugs and to select compounds for the drug development process comprising new indications. Tebrophen, a known antiviral drug, was found to inhibit activities on inflammation and cancer related
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In vitro high-throughput screening was carried out in order to detect new activities for old drugs and to select compounds for the drug development process comprising new indications. Tebrophen, a known antiviral drug, was found to inhibit activities on inflammation and cancer related targets. In primary screening this semisynthetic halogenated polyphenol was identified to inhibit the activities of kinases ZAP-70 and Lck (IC50 0.34 µM and 16 µM, respectively), as well as hydrolase DPPIV (at 80 µM 41% inhibition). Next, it showed no cytotoxic effects on standard cell lines within 24 h. However, tebrophen slowed propagation of breast cancer (MDA-MB-231), osteosarcoma (U2OS) and cervical carcinoma (HeLa), through at least 35 population doublings in a dose-dependent manner. It completely stopped the division of the prostate cancer (PC3) cell line at 50 µM concentration and the cells entered massive cell death in less than 20 days. On the other hand, tebrophen did not influence the growth of normal fibroblasts. According to the measured oxidative burst and estimated in silico parameters its direct antioxidative ability is limited. The obtained results indicate that tebrophen can be considered a promising lead molecule for generating more soluble derivatives with specific anticancer efficacy. Full article
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Open AccessArticle Simultaneous Quantification of Five Bioactive Components of Acanthopanax senticosus and Its Extract by Ultra Performance Liquid Chromatography with Electrospray Ionization Time-of-Flight Mass Spectrometry
Molecules 2012, 17(7), 7903-7913; doi:10.3390/molecules17077903
Received: 24 May 2012 / Revised: 19 June 2012 / Accepted: 27 June 2012 / Published: 29 June 2012
Cited by 5 | PDF Full-text (238 KB)
Abstract
A simple and reliable ultra performance liquid chromatography coupled with electrospray ionization time-of-flight mass spectrometry method (UPLC-TOF-MS) was developed and validated for the simultaneous determination of the major bioactive constituents in Acanthopanax senticosus and its extract. The separation of five compounds was performed
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A simple and reliable ultra performance liquid chromatography coupled with electrospray ionization time-of-flight mass spectrometry method (UPLC-TOF-MS) was developed and validated for the simultaneous determination of the major bioactive constituents in Acanthopanax senticosus and its extract. The separation of five compounds was performed on a UPLCTM HSS T3 column (100 mm × 2.1 mm, 1.7 μm) with gradient elution using a mobile phase consisting of 0.1% aqueous formic acid and acetonitrile containing 0.1% formic acid. All targeted compounds (syringin, chlorogenid acid, caffeic acid, eleutheroside E and isofraxidin) were baseline separated within 5.3 min in samples, which represented an approximate six-fold reduction in the analysis time in comparison to published HPLC method. Quantitation was carried out working in the V mode using the narrow widow extracted ion chromatograms (nwXICs) of each compound (extracted using a 20 mDa window). Furthermore, all calibration curves showed good linearity (r > 0.999) within the test ranges. The precision was evaluated by intra- and inter-day tests, which revealed relative standard deviation (RSD) values of less than 3.88%. The recoveries for the quantified compounds were between 96.3% and 103.7%, with RSD values below 2.89%. According to the literature, this study represents the first investigation of the simultaneous analysis of multiple components and the method can be applied to determine the amounts of the major compounds in Acanthopanax senticosus and its extract by UPLC-TOF-MS. Full article
Open AccessArticle Variable-Temperature 1H-NMR Studies on Two C-Glycosylflavones
Molecules 2012, 17(7), 7914-7926; doi:10.3390/molecules17077914
Received: 5 April 2012 / Revised: 26 May 2012 / Accepted: 18 June 2012 / Published: 2 July 2012
Cited by 5 | PDF Full-text (297 KB)
Abstract
Two known C-glycosylflavones, swertisin and embinoidin, were isolated from the leaves of Anthurium aripoense, and characterized by room temperature 1D and 2D NMR experiments. At this temperature, the 1H- and 13C-NMR spectra of these C-glycosylflavones revealed doubling of
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Two known C-glycosylflavones, swertisin and embinoidin, were isolated from the leaves of Anthurium aripoense, and characterized by room temperature 1D and 2D NMR experiments. At this temperature, the 1H- and 13C-NMR spectra of these C-glycosylflavones revealed doubling of signals, which suggested the presence of two rotamers in solution. Variable-temperature (VT) 1H-NMR studies supported this hypothesis. The T-ROESY data, in addition to the theoretical (MM2) calculations utilizing the Chem3D Pro software, confirmed the hypothesis that the two rotamers interchange via rotation about the C-glycosidic bond. Full article
(This article belongs to the Section Natural Products)
Open AccessArticle Novel Antimicrobial Organic Thermal Stabilizer and Co-Stabilizer for Rigid PVC
Molecules 2012, 17(7), 7927-7940; doi:10.3390/molecules17077927
Received: 18 May 2012 / Revised: 15 June 2012 / Accepted: 18 June 2012 / Published: 2 July 2012
Cited by 14 | PDF Full-text (759 KB)
Abstract
Biologically active N-benzoyl-4-(N-maleimido)-phenylhydrazide (BMPH) was synthesized and its structure was confirmed by elemental analysis and various spectral tools. It was examined as a thermal stabilizer and co-stabilizer for rigid poly (vinyl chloride) at 180 °C in air. Blending BMPH with
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Biologically active N-benzoyl-4-(N-maleimido)-phenylhydrazide (BMPH) was synthesized and its structure was confirmed by elemental analysis and various spectral tools. It was examined as a thermal stabilizer and co-stabilizer for rigid poly (vinyl chloride) at 180 °C in air. Blending BMPH with reference samples in different ratios greatly lengthens the thermal stability value and improves the extent of discoloration of PVC. TGA confirmed the improved stability of PVC in presence of the investigated organic stabilizer. GPC measurements were done to investigate the changes occurred in the molecular masses of the degraded samples of blank PVC and PVC in presence of the novel stabilizer. BMPH showed good antimicrobial activity towards two kinds of bacteria and two kinds of fungi. Full article
(This article belongs to the Section Organic Synthesis)
Open AccessArticle Platinum Clusters on Vacancy-Type Defects of Nanometer-Sized Graphene Patches
Molecules 2012, 17(7), 7941-7960; doi:10.3390/molecules17077941
Received: 8 May 2012 / Revised: 11 June 2012 / Accepted: 19 June 2012 / Published: 2 July 2012
Cited by 5 | PDF Full-text (2272 KB)
Abstract
Density functional theory calculations found that spin density distributions of platinum clusters adsorbed on nanometer-size defective graphene patches with zigzag edges deviate strongly from those in the corresponding bare clusters, due to strong Pt-C interactions. In contrast, platinum clusters on the pristine patch
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Density functional theory calculations found that spin density distributions of platinum clusters adsorbed on nanometer-size defective graphene patches with zigzag edges deviate strongly from those in the corresponding bare clusters, due to strong Pt-C interactions. In contrast, platinum clusters on the pristine patch have spin density distributions similar to the bare cases. The different spin density distributions come from whether underlying carbon atoms have radical characters or not. In the pristine patch, center carbon atoms do not have spin densities, and they cannot influence radical characters of the absorbed cluster. In contrast, radical characters appear on the defective sites, and thus spin density distributions of the adsorbed clusters are modulated by the Pt-C interactions. Consequently, characters of platinum clusters adsorbed on the sp2 surface can be changed by introducing vacancy-type defects. Full article
(This article belongs to the Special Issue Fullerene Chemistry)
Open AccessArticle Effect of Ionic Liquid on the Determination of Aromatic Amines as Contaminants in Hair Dyes by Liquid Chromatography Coupled to Electrochemical Detection
Molecules 2012, 17(7), 7961-7979; doi:10.3390/molecules17077961
Received: 16 May 2012 / Revised: 24 June 2012 / Accepted: 25 June 2012 / Published: 2 July 2012
Cited by 12 | PDF Full-text (1022 KB)
Abstract
The room temperature ionic liquid (IL) 1-butyl-3-methylimidazolium bis-(trifluorometanesulfonyl)imide BMIm[NTf2] was used as a novel medium for improvement of separation and quantization of 16 aromatic amines typically present as contaminants in consumer products and detected by HPLC coupled to an electrochemical detector.
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The room temperature ionic liquid (IL) 1-butyl-3-methylimidazolium bis-(trifluorometanesulfonyl)imide BMIm[NTf2] was used as a novel medium for improvement of separation and quantization of 16 aromatic amines typically present as contaminants in consumer products and detected by HPLC coupled to an electrochemical detector. The aromatic amines, namely 4,4'-diaminodiphenylmethane, 4-chloroaniline, 2-methoxy-5-methyl-aniline, 3,3'-dimethylbenzidine, 2,4-diaminotoluidine, 2-chloro-4-nitroaniline, 4,4'-oxydianiline, aniline, 3,3'-dichlorobenzidine, benzidine, 4-aminobiphenyl, o-dianisidine, o-anisidine, o-toluidine, 4,4'-methylene-bis-2-chloroaniline and 2-naphthyl-amine are oxidized in methanol/BMIm[NTf2] at a potential around +0.68V to +0.93V vs. Ag/AgCl at a glassy carbon electrode, which is the base for their determination by HPLC/ED. Using the optimized conditions of methanol/BMIm[NTf2] 70:30 (v/v) as mobile phase, flow-rate of 0.8 mL·min−1, column CLC-ODS, Eap = +1.0 V and T = 40 °C analytical curves were constructed for each of the tested amines. Good linearity was obtained in the concentration range of 1.09 mg·L−1 to 217 mg·L−1, with excellent correlation coefficients. The limits of detection reached 0.021 mg·L−1 to 0.246 mg·L−1 and good relative standard deviations (RSD, n = 3) were obtained from the measurements. Satisfactory recovery for each aromatic amine was achieved, ranging from 95 to 103%. The developed method was successfully applied to determine six aromatic amines present as contaminants in commercial hair dye samples. Full article
(This article belongs to the Special Issue Ionic Liquids)
Open AccessCommunication Rhizonin A from Burkholderia sp. KCTC11096 and Its Growth Promoting Role in Lettuce Seed Germination
Molecules 2012, 17(7), 7980-7988; doi:10.3390/molecules17077980
Received: 19 May 2012 / Revised: 19 June 2012 / Accepted: 28 June 2012 / Published: 3 July 2012
PDF Full-text (613 KB)
Abstract
We isolated and identified a gibberellin-producing Burkholderia sp. KCTC 11096 from agricultural field soils. The culture filtrate of plant growth promoting rhizobacteria (PGPR) significantly increased the germination and growth of lettuce and Chinese cabbage seeds. The ethyl acetate extract of the PGPR culture
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We isolated and identified a gibberellin-producing Burkholderia sp. KCTC 11096 from agricultural field soils. The culture filtrate of plant growth promoting rhizobacteria (PGPR) significantly increased the germination and growth of lettuce and Chinese cabbage seeds. The ethyl acetate extract of the PGPR culture showed significantly higher rate of lettuce seed germination and growth as compared to the distilled water treated control. The ethyl acetate fraction of the Burkholderia sp. was subjected to bioassay-guided isolation and we obtained for the first time from a Burkholderia sp. the plant growth promoting compound rhizonin A (1), which was characterized through NMR and MS techniques. Application of various concentrations of 1 significantly promoted the lettuce seed germination as compared to control. Full article
(This article belongs to the Section Natural Products)
Open AccessArticle Flavonoids and Other Compounds from Ouratea ferruginea (Ochnaceae) as Anticancer and Chemopreventive Agents
Molecules 2012, 17(7), 7989-8000; doi:10.3390/molecules17077989
Received: 16 May 2012 / Revised: 20 June 2012 / Accepted: 22 June 2012 / Published: 3 July 2012
Cited by 8 | PDF Full-text (226 KB)
Abstract
The chemical study of the extracts from leaves and stems of Ouratea ferruginea allowed the identification of a new isoflavone, 5-hydroxy-7,3′4′5′-tetramethoxyisoflavone, and twenty two known compounds, including friedelin, 3β-friedelinol, lupeone, a mixture of sitosterol, stigmasterol and campesterol, sitosteryl- and stigmasteryl-3-O-b-D-glucopyranosides, 5,4′-dihydroxy-7,5′,3′-trimethoxyisoflavone,
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The chemical study of the extracts from leaves and stems of Ouratea ferruginea allowed the identification of a new isoflavone, 5-hydroxy-7,3′4′5′-tetramethoxyisoflavone, and twenty two known compounds, including friedelin, 3β-friedelinol, lupeone, a mixture of sitosterol, stigmasterol and campesterol, sitosteryl- and stigmasteryl-3-O-b-D-glucopyranosides, 5,4′-dihydroxy-7,5′,3′-trimethoxyisoflavone, 5,4′-dihydroxy-7,3′-di-methoxyisoflavone (7,3′-di-O-methylorobol), 5,7,4′-trihydroxy-3′,5′-dimethoxyisoflavone (piscigenin), 2R,3R-epicatechin, syringic acid, 2,6-dimethoxybenzoquinone, 2,6-dimethoxyhydroquinone, syringic and ferulic aldehyde, a mixture of vanillic acid, 1-hydroxy-2-methoxy-4-(1E-3-hydroxy-1-propenyl)-benzene and 3,5-dimethoxy-4-hydroxy-dihydrocinamaldehyde, besides amenthoflavone and 7-O-methylamenthoflavone (sequoiaflavone) which are considered as chemotaxonomic markers of Ouratea. The structures were identified by IR, 1H- and 13C-NMR and GC-MS, HPLC-MS, besides comparison with literature data. The inhibitory effects of 5,4′-dihydroxy-7,5′,3′-trimethoxyisoflavone, 7,3′-di-O-methylorobol, piscigenin and 7-O-methylamenthoflavone on cytochrome P450-dependent 7-ethoxycoumarin O-deethylase (ECOD) and glutathione S-transferase (GST) were evaluated in vitro. The 5,4′-dihydroxy-7,5′,3′-trimethoxy-isoflavone was the best inhibitor, inhibiting almost 75% of GST activity. Sequoiaflavone was the most potent inhibitor, inhibiting ECOD assay in 75%. These activities allow us to consider both these flavonoids as potential anticancer and chemopreventive agents. Full article
(This article belongs to the Section Natural Products)
Open AccessArticle Pharmacological Evaluation of LiuWei Zhuanggu Granules in Rats
Molecules 2012, 17(7), 8001-8009; doi:10.3390/molecules17078001
Received: 4 June 2012 / Revised: 20 June 2012 / Accepted: 20 June 2012 / Published: 3 July 2012
PDF Full-text (169 KB)
Abstract
Many commonly consumed foods, herbs and spices contain a complex array of naturally occurring bioactive molecules called phytochemicals, which may confer health benefits. In this study, the impact of LiuWei Zhuanggu Granules (LWZGG) on mineral metabolism in osteopenia development was evaluated. Results showed
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Many commonly consumed foods, herbs and spices contain a complex array of naturally occurring bioactive molecules called phytochemicals, which may confer health benefits. In this study, the impact of LiuWei Zhuanggu Granules (LWZGG) on mineral metabolism in osteopenia development was evaluated. Results showed that serum estrogen, bone gla protein (BGP), and calcitonin (CT) levels, bone Ca, Zn and Cu levels, femur, lumbar vertebrae and trabecular bone density, tibia maximum stress and maximum bending strength were increased, and serum parathyroid hormone (PTH), serum and urine Ca, Zn and Cu levels were decreased in rat bone. It can be concluded that LWZGG is useful to improve bone quality in ovariectomized (OVX) rats. Full article
Open AccessArticle Gamma-Mangostin, a Micronutrient of Mangosteen Fruit, Induces Apoptosis in Human Colon Cancer Cells
Molecules 2012, 17(7), 8010-8021; doi:10.3390/molecules17078010
Received: 18 May 2012 / Revised: 25 June 2012 / Accepted: 27 June 2012 / Published: 3 July 2012
Cited by 7 | PDF Full-text (412 KB)
Abstract
Recently colorectal cancer rates have increased rapidly in Taiwan. The treatment of colorectal cancer includes surgery, radiation therapy and chemotherapy. Mangosteen (Garcinia mangostana) is a famous Asian tropical fruit. γ-Mangostin is a xanthone derivative isolated from the fruit hull. In previous studies,
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Recently colorectal cancer rates have increased rapidly in Taiwan. The treatment of colorectal cancer includes surgery, radiation therapy and chemotherapy. Mangosteen (Garcinia mangostana) is a famous Asian tropical fruit. γ-Mangostin is a xanthone derivative isolated from the fruit hull. In previous studies, we found evidence of anti-inflammatory and anti-brain tumor activities in γ-mangostin. In this study, we performed further studies to assess the apoptotic effects of γ-mangostin on colorectal adenocarcinoma cells HT29. γ-Mangostin showed concentration and time-dependent cytotoxic effects on HT29 cells. Microscopic observation under Giemsa staining showed that γ-mangostin induced cellular swelling and the appearance of apoptotic bodies, characteristic of apoptosis in HT29 cells. In addition, flow cytometry analysis showed an increase of hypodiploid cells in γ-mangostin-treated HT29 cells, while enhancement of intracellular peroxide production was detected in the same γ-mangostin-treated cells by DCHDA assay and DiOC6(3) staining. In view of the above results, γ-mangostin has demonstrated anticancer activity and induces apoptosis in HT29 colorectal adenocarcinoma cells. The evidence suggests that γ-mangostin could serve as a micronutrient for colon cancer prevention and is a potential lead compound for the development of anti-colon cancer agents. Full article
(This article belongs to the collection Bioactive Compounds)
Open AccessArticle Metabolic Profiling of Lactococcus lactis Under Different Culture Conditions
Molecules 2012, 17(7), 8022-8036; doi:10.3390/molecules17078022
Received: 25 May 2012 / Revised: 13 June 2012 / Accepted: 14 June 2012 / Published: 3 July 2012
Cited by 6 | PDF Full-text (501 KB)
Abstract
Gas chromatography mass spectrometry (GC-MS) and headspace gas chromatography mass spectrometry (HS/GC-MS) were used to study metabolites produced by Lactococcus lactis subsp. cremoris MG1363 grown at a temperature of 30 °C with and without agitation at 150 rpm, and at 37 °C without
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Gas chromatography mass spectrometry (GC-MS) and headspace gas chromatography mass spectrometry (HS/GC-MS) were used to study metabolites produced by Lactococcus lactis subsp. cremoris MG1363 grown at a temperature of 30 °C with and without agitation at 150 rpm, and at 37 °C without agitation. It was observed that L. lactis produced more organic acids under agitation. Primary alcohols, aldehydes, ketones and polyols were identified as the corresponding trimethylsilyl (TMS) derivatives, whereas amino acids and organic acids, including fatty acids, were detected through methyl chloroformate derivatization. HS analysis indicated that branched-chain methyl aldehydes, including 2-methylbutanal, 3-methylbutanal, and 2-methylpropanal are degdradation products of isoleucine, leucine or valine. Multivariate analysis (MVA) using partial least squares discriminant analysis (PLS-DA) revealed the major differences between treatments were due to changes of amino acids and fermentation products. Full article
Open AccessArticle 6-Shogaol-Rich Extract from Ginger Up-Regulates the Antioxidant Defense Systems in Cells and Mice
Molecules 2012, 17(7), 8037-8055; doi:10.3390/molecules17078037
Received: 21 May 2012 / Revised: 23 June 2012 / Accepted: 2 July 2012 / Published: 4 July 2012
Cited by 33 | PDF Full-text (766 KB)
Abstract
The rhizome of ginger (Zingiber officinale Roscoe) is known to have several bioactive compounds including gingerols and shogaols which possess beneficial health properties such as anti-inflammatory and chemopreventive effects. Based on recent observations that 6-shogaol may have more potent bioactivity than 6-gingerol,
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The rhizome of ginger (Zingiber officinale Roscoe) is known to have several bioactive compounds including gingerols and shogaols which possess beneficial health properties such as anti-inflammatory and chemopreventive effects. Based on recent observations that 6-shogaol may have more potent bioactivity than 6-gingerol, we obtained a 6-shogaol-rich extract from ginger and examined its effects on the nuclear factor E2-related factor2 (Nrf2)/antioxidant response element (ARE) pathway in vitro and in vivo. 6-Shogaol-rich extract was produced by extracting ginger powder with 95% ethanol at 80 °C after drying at 80 °C (GEE8080). GEE8080 contained over 6-fold more 6-shogaol compared to the room temperature extract (GEE80RT). In HepG2 cells, GEE8080 displayed much stronger inductions of ARE-reporter gene activity and Nrf2 expression than GEE80RT. GEE8080 stimulated phosphorylations of mitogen-activated protein kinases (MAPKs) such as ERK, JNK, and p38. Moreover, the GEE8080-induced expressions of Nrf2 and HO-1 were attenuated by treatments of SB202190 (a p38 specific inhibitor) and LY294002 (an Akt specific inhibitor). In a mouse model, the GEE8080 decreased the diethylnitrosamine (DEN)-mediated elevations of serum aspartate transaminase and alanine transaminase as well as the DEN-induced hepatic lipid peroxidation. Inductions of Nrf2 and HO-1 by GEE8080 were also confirmed in the mice. In addition, the administration of GEE8080 to the mice also restored the DEN-reduced activity and protein expression of hepatic antioxidant enzymes such as superoxide dismutase, glutathione peroxidase and catalase. In conclusion, GEE8080, a 6-shogaol-rich ginger extract, may enhance antioxidant defense mechanism through the induction of Nrf2 and HO-1 regulated by p38 MAPK and PI3k/Akt pathway in vitro and in vivo. Full article
(This article belongs to the Special Issue Antioxidants 2012)
Open AccessArticle Thermal Hazard Evaluation of Lauroyl Peroxide Mixed with Nitric Acid
Molecules 2012, 17(7), 8056-8067; doi:10.3390/molecules17078056
Received: 19 April 2012 / Revised: 20 June 2012 / Accepted: 25 June 2012 / Published: 4 July 2012
Cited by 5 | PDF Full-text (276 KB)
Abstract
Many thermal runaway incidents have been caused by organic peroxides due to the peroxy group, –O–O–, which is essentially unstable and active. Lauroyl peroxide (LPO) is also sensitive to thermal sources and is incompatible with many materials, such as acids, bases, metals, and
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Many thermal runaway incidents have been caused by organic peroxides due to the peroxy group, –O–O–, which is essentially unstable and active. Lauroyl peroxide (LPO) is also sensitive to thermal sources and is incompatible with many materials, such as acids, bases, metals, and ions. From the thermal decomposition reaction of various concentrations of nitric acid (HNO3) (from lower to higher concentrations) with LPO, experimental data were obtained as to its exothermic onset temperature (T0), heat of decomposition (ΔHd), isothermal time to maximum rate (TMRiso), and other safety parameters exclusively for loss prevention of runaway reactions and thermal explosions. As a novel finding, LPO mixed with HNO3 can produce the detonation product of 1-nitrododecane. We used differential scanning calorimetry (DSC), thermal activity monitor III (TAM III), and gas chromatography/mass spectrometer (GC/MS) analyses of the reactivity for LPO and itself mixed with HNO3 to corroborate the decomposition reactions and reaction mechanisms in these investigations. Full article
(This article belongs to the Special Issue Dendrimers - from Synthesis to Applications)
Open AccessCommunication Application of Hydrogen Peroxide Encapsulated in Silica Xerogels to Oxidation Reactions
Molecules 2012, 17(7), 8068-8078; doi:10.3390/molecules17078068
Received: 13 May 2012 / Revised: 18 June 2012 / Accepted: 25 June 2012 / Published: 4 July 2012
Cited by 12 | PDF Full-text (269 KB)
Abstract
Hydrogen peroxide was encapsulated into a silica xerogel matrix by the sol-gel technique. The composite was tested as an oxidizing agent both under conventional and microwave conditions in a few model reactions: Noyori’s method of octanal and 2-octanol oxidation and cycloctene epoxidation in
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Hydrogen peroxide was encapsulated into a silica xerogel matrix by the sol-gel technique. The composite was tested as an oxidizing agent both under conventional and microwave conditions in a few model reactions: Noyori’s method of octanal and 2-octanol oxidation and cycloctene epoxidation in a 1,1,1-trifluoroethanol/Na2WO4 system. The results were compared with yields obtained for reactions with 30% H2O2 and urea-hydrogen peroxide (UHP) as oxidizing agents. It was found that the composite has activity similar to 30% H2O2 and has a several advantages over UHP such as the fact that silica and H2O are the only products of the composite decomposition or no contamination by urea or its derivatives occurs; the xerogel is easier to heated by microwave irradiation than UHP and could be used as both an oxidizing agent and as solid support for microwave assisted solvent-free oxidations. Full article
(This article belongs to the Section Organic Synthesis)
Open AccessArticle Purification, Characterization and Antioxidant Activities in Vitro and in Vivo of the Polysaccharides from Boletus edulis Bull
Molecules 2012, 17(7), 8079-8090; doi:10.3390/molecules17078079
Received: 22 May 2012 / Revised: 20 June 2012 / Accepted: 22 June 2012 / Published: 5 July 2012
Cited by 8 | PDF Full-text (208 KB)
Abstract
A water-soluble polysaccharide (BEBP) was extracted from Boletus edulis Bull using hot water extraction followed by ethanol precipitation. The polysaccharide BEBP was further purified by chromatography on a DEAE-cellulose column, giving three major polysaccharide fractions termed BEBP-1, BEBP-2 and BEBP-3. In the next
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A water-soluble polysaccharide (BEBP) was extracted from Boletus edulis Bull using hot water extraction followed by ethanol precipitation. The polysaccharide BEBP was further purified by chromatography on a DEAE-cellulose column, giving three major polysaccharide fractions termed BEBP-1, BEBP-2 and BEBP-3. In the next experiment, the average molecular weight (Mw), IR and monosaccharide compositional analysis of the three polysaccharide fractions were determined. The evaluation of antioxidant activities both in vitro and in vivo suggested that BEBP-3 had good potential antioxidant activity, and should be explored as a novel potential antioxidant. Full article
(This article belongs to the Section Natural Products)
Open AccessArticle Design, Synthesis, and Anti-Proliferative Evaluation of [1,1′-biphenyl]-4-ols as Inhibitor of HUVEC Migration and Tube Formation
Molecules 2012, 17(7), 8091-8104; doi:10.3390/molecules17078091
Received: 10 May 2012 / Revised: 11 June 2012 / Accepted: 20 June 2012 / Published: 5 July 2012
PDF Full-text (634 KB)
Abstract
Allylated biphenol neolignans contain a variety of chemopreventive entities that have been used as anti-tumor drug leads. Herein, 37 allylated biphenols were evaluated for anti-proliferative activity by the MTT assay and inhibitory effect on the migration and tube formation of HUVECs featuring anti-angiogenic
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Allylated biphenol neolignans contain a variety of chemopreventive entities that have been used as anti-tumor drug leads. Herein, 37 allylated biphenols were evaluated for anti-proliferative activity by the MTT assay and inhibitory effect on the migration and tube formation of HUVECs featuring anti-angiogenic properties. 3-(2-Methylbut-3-en-2-yl)-3′,5′-bis(trifluoromethyl)-[1,1′-biphenyl]-4-ol (5c) exerted an inhibitory effect on HUVECs compared to honokiol (IC50 = 47.0 vs. 52.6 μM) and showed significant blocking effects on the proliferation of C26, Hela, K562, A549, and HepG2 (IC50 = 15.0, 25.0, 21.2, 29.5, and 13.0 μM, respectively), superior to those of honokiol (IC50 = 65.1, 62.0, 42.0, 75.0, and 55.4 μM, respectively). Importantly, compound 5c inhibited the migration and capillary-like tube formation of HUVECs in vitro. Full article
(This article belongs to the Section Medicinal Chemistry)
Open AccessArticle A New Synthetic Route to Original Sulfonamide Derivatives in 2-Trichloromethylquinazoline Series: A Structure-Activity Relationship Study of Antiplasmodial Activity
Molecules 2012, 17(7), 8105-8117; doi:10.3390/molecules17078105
Received: 14 May 2012 / Revised: 25 June 2012 / Accepted: 26 June 2012 / Published: 5 July 2012
Cited by 7 | PDF Full-text (243 KB)
Abstract
We report herein a simple and efficient two-step synthetic approach to new 2-trichloromethylquinazolines possessing a variously substituted sulfonamide group at position 4 used to prepare new quinazolines with antiparasitic properties. Thus, an original series of 20 derivatives was synthesized, which proved to be
[...] Read more.
We report herein a simple and efficient two-step synthetic approach to new 2-trichloromethylquinazolines possessing a variously substituted sulfonamide group at position 4 used to prepare new quinazolines with antiparasitic properties. Thus, an original series of 20 derivatives was synthesized, which proved to be less-toxic than previously synthesized hits on the human HepG2 cell line, but did not display significant antiplasmodial activity. A brief Structure-Activity Relationship (SAR) evaluation shows that a more restricted conformational freedom is probably necessary for providing antiplasmodial activity. Full article
(This article belongs to the Section Organic Synthesis)
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Open AccessArticle Food-Related Compounds That Modulate Expression of Inducible Nitric Oxide Synthase May Act as Its Inhibitors
Molecules 2012, 17(7), 8118-8135; doi:10.3390/molecules17078118
Received: 2 May 2012 / Revised: 6 June 2012 / Accepted: 7 June 2012 / Published: 5 July 2012
Cited by 5 | PDF Full-text (1618 KB)
Abstract
Natural compounds commonly found in foods may contribute to protect cells against the deleterious effects of inflammation. These anti-inflammatory properties have been linked to the modulation of transcription factors that control expression of inflammation-related genes, including the inducible nitric oxide synthase (iNOS), rather
[...] Read more.
Natural compounds commonly found in foods may contribute to protect cells against the deleterious effects of inflammation. These anti-inflammatory properties have been linked to the modulation of transcription factors that control expression of inflammation-related genes, including the inducible nitric oxide synthase (iNOS), rather than a direct inhibitory action on these proteins. In this study, forty two natural dietary compounds, known for their ability to exert an inhibitory effect on the expression of iNOS, have been studied in silico as docking ligands on two available 3D structures for this protein (PDB ID: 3E7G and PDB ID: 1NSI). Natural compounds such as silibinin and cyanidin-3-rutinoside and other flavonoids showed the highest theoretical affinities for iNOS. Docking affinity values calculated for several known iNOS inhibitors significatively correlated with their reported half maximal inhibitory concentrations (R = 0.842, P < 0.0001), suggesting the computational reliability of the predictions made by our docking simulations. Moreover, docking affinity values for potent iNOS inhibitors are of similar magnitude to those obtained for some studied natural products. Results presented here indicate that, in addition to gene expression modulation of proteins involved in inflammation, some chemicals present in food may be acting by direct binding and possible inhibiting actions on iNOS. Full article
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Open AccessArticle Effect of Cross-Linking and Enzymatic Hydrolysis Composite Modification on the Properties of Rice Starches
Molecules 2012, 17(7), 8136-8146; doi:10.3390/molecules17078136
Received: 3 May 2012 / Revised: 22 June 2012 / Accepted: 3 July 2012 / Published: 6 July 2012
Cited by 5 | PDF Full-text (228 KB)
Abstract
Native rice starch lacks the versatility necessary to function adequately under rigorous industrial processing, so modified starches are needed to meet the functional properties required in food products. This work investigated the impact of enzymatic hydrolysis and cross-linking composite modification on the properties
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Native rice starch lacks the versatility necessary to function adequately under rigorous industrial processing, so modified starches are needed to meet the functional properties required in food products. This work investigated the impact of enzymatic hydrolysis and cross-linking composite modification on the properties of rice starches. Rice starch was cross-linked with epichlorohydrin (EPI) with different concentrations (0.5%, 0.7%, 0.9% w/w, on a dry starch basis), affording cross-linked rice starches with the three different levels of cross-linking that were named R1, R2, and R3, respectively. The cross-linked rice starches were hydrolyzed by α-amylase and native, hydrolyzed, and hydrolyzed cross-linked rice starches were comparatively studied. It was found that hydrolyzed cross-linked rice starches showed a lower the degree of amylase hydrolysis compared with hydrolyzed rice starch. The higher the degree of cross-linking, the higher the capacity to resist enzyme hydrolysis. Hydrolyzed cross-linked rice starches further increased the adsorptive capacities of starches for liquids and decreased the trend of retrogradation, and it also strengthened the capacity to resist shear compared to native and hydrolyzed rice starches. Full article
Open AccessArticle Evaluation of Black Tea Polyphenol Extract Against the Retrogradation of Starches from Various Plant Sources
Molecules 2012, 17(7), 8147-8158; doi:10.3390/molecules17078147
Received: 31 May 2012 / Revised: 29 June 2012 / Accepted: 3 July 2012 / Published: 6 July 2012
Cited by 7 | PDF Full-text (468 KB)
Abstract
The effects of black tea polyphenol extract (BTPE) on the retrogradation of starches from different plant sources were studied using differential scanning calorimetry (DSC) and X-ray diffraction (XRD). DSC analysis shows that the gelatinization temperature of maize starch and starches from different rice
[...] Read more.
The effects of black tea polyphenol extract (BTPE) on the retrogradation of starches from different plant sources were studied using differential scanning calorimetry (DSC) and X-ray diffraction (XRD). DSC analysis shows that the gelatinization temperature of maize starch and starches from different rice varieties increased with increasing BTPE level. After storage at 4 °C, BTPE at a concentration of 15% markedly retarded the retrogradation of maize starch and starches from different rice varieties. Native maize starch and starches from different rice varieties showed typical A-type X-ray diffraction patterns, while native potato starch showed a typical B-type X-ray diffraction pattern. Adding BTPE significantly affected the crystalline region and intensities of X-ray diffraction peaks of maize and rice starch granules. It is concluded that adding BTPE markedly inhibits the retrogradation of maize starch and starches from different rice varieties, but has no significant influence on the gelatinization and retrogradation characteristics of potato starch. Full article
Open AccessArticle p-Cymene Protects Mice Against Lipopolysaccharide-Induced Acute Lung Injury by Inhibiting Inflammatory Cell Activation
Molecules 2012, 17(7), 8159-8173; doi:10.3390/molecules17078159
Received: 5 May 2012 / Revised: 3 July 2012 / Accepted: 4 July 2012 / Published: 6 July 2012
Cited by 10 | PDF Full-text (1278 KB)
Abstract
The objective of this study was to test the hypothesis that p-cymene can attenuate acute lung injury induced by lipopolysaccharide (LPS) in vivo. In the mouse model of LPS-induced acute lung injury, intraperitoneal preconditioning with p-cymene resulted in a significant
[...] Read more.
The objective of this study was to test the hypothesis that p-cymene can attenuate acute lung injury induced by lipopolysaccharide (LPS) in vivo. In the mouse model of LPS-induced acute lung injury, intraperitoneal preconditioning with p-cymene resulted in a significant reduction of pro-inflammatory cytokines (TNF-α, IL-1β and IL-6), lung water gain, inflammatory cell infiltration, lung tissue myeloperoxidase activity. In addition, p-cymene blocked the phosphorylation of IκBα protein and mitogen-activated protein kinases (MAPK) signaling pathway activation. Histopathologic examination of lung tissue indicated that p-cymene treatment markedly decreased focal thickening, congestion, pulmonary edema, and inflammatory cells infiltration. The results showed that p-cymene had a protective effect on LPS-induced ALI in mice. Full article
Open AccessArticle Synthesis and Fungicidal Activity of Novel 2,3-Disubstituted-1,3-benzoxazines
Molecules 2012, 17(7), 8174-8185; doi:10.3390/molecules17078174
Received: 10 June 2012 / Revised: 25 June 2012 / Accepted: 26 June 2012 / Published: 6 July 2012
Cited by 11 | PDF Full-text (220 KB)
Abstract
A series of new 2,3-disubstituted-3,4-dihydro-2H-1,3-benzoxazines were prepared in moderate to excellent yields by aza-acetalizations of aromatic aldehydes with 2-(N-substituted aminomethyl)phenols in the presence of TMSCl. Their structures were confirmed by IR, 1H-NMR, 13C-NMR, MS and elemental analysis.
[...] Read more.
A series of new 2,3-disubstituted-3,4-dihydro-2H-1,3-benzoxazines were prepared in moderate to excellent yields by aza-acetalizations of aromatic aldehydes with 2-(N-substituted aminomethyl)phenols in the presence of TMSCl. Their structures were confirmed by IR, 1H-NMR, 13C-NMR, MS and elemental analysis. The fungicidal activities of the target compounds were preliminarily evaluated, and some compounds exhibited good activity against Rhizoctonia solani. Full article
(This article belongs to the Section Organic Synthesis)
Open AccessArticle Cytotoxic Effect of Eudesmanolides Isolated from Flowers of Tanacetum vulgare ssp. siculum
Molecules 2012, 17(7), 8186-8195; doi:10.3390/molecules17078186
Received: 24 May 2012 / Revised: 29 June 2012 / Accepted: 2 July 2012 / Published: 9 July 2012
Cited by 15 | PDF Full-text (240 KB)
Abstract
A phytochemical analysis of the dichloromethane extract from the flowers of a subspecies of Tanacetum vulgare growing in Sicily was carried out. Five known sesquiterpene lactones with the eudesmane skeleton have been isolated and the cytotoxic activity of these compounds was tested in
[...] Read more.
A phytochemical analysis of the dichloromethane extract from the flowers of a subspecies of Tanacetum vulgare growing in Sicily was carried out. Five known sesquiterpene lactones with the eudesmane skeleton have been isolated and the cytotoxic activity of these compounds was tested in vitro on A549 (human lung carcinoma epithelial-like) and V79379A (Chinese hamster lung fibroblast-like) cells using the tetrazolium salt reduction (MTT) assay. All of tested compounds induced high time- and concentration-dependent cytotoxic effects. Full article
(This article belongs to the Section Natural Products)
Open AccessArticle Terpenes as Green Solvents for Extraction of Oil from Microalgae
Molecules 2012, 17(7), 8196-8205; doi:10.3390/molecules17078196
Received: 1 June 2012 / Revised: 21 June 2012 / Accepted: 26 June 2012 / Published: 9 July 2012
Cited by 22 | PDF Full-text (1014 KB)
Abstract
Herein is described a green and original alternative procedure for the extraction of oil from microalgae. Extractions were carried out using terpenes obtained from renewable feedstocks as alternative solvents instead of hazardous petroleum solvents such as n-hexane. The described method is achieved
[...] Read more.
Herein is described a green and original alternative procedure for the extraction of oil from microalgae. Extractions were carried out using terpenes obtained from renewable feedstocks as alternative solvents instead of hazardous petroleum solvents such as n-hexane. The described method is achieved in two steps using Soxhlet extraction followed by the elimination of the solvent from the medium using Clevenger distillation in the second step. Oils extracted from microalgae were compared in terms of qualitative and quantitative determination. No significant difference was obtained between each extract, allowing us to conclude that the proposed method is green, clean and efficient. Full article
(This article belongs to the Section Natural Products)
Open AccessArticle An Alternative Synthesis of 3′,4′-Diaminoflavones to Evaluate Their Antioxidant Ability and Cell Apoptosis of Zebrafish Larvae
Molecules 2012, 17(7), 8206-8216; doi:10.3390/molecules17078206
Received: 1 June 2012 / Revised: 2 July 2012 / Accepted: 6 July 2012 / Published: 9 July 2012
Cited by 3 | PDF Full-text (1313 KB)
Abstract
We described herein a concise synthesis of 3′,4′-diaminoflavone 10. This new, three-step synthetic approach is more efficient than the conventional seven-step synthetic method. The route is shortened significantly by introducing the amino moieties early and eliminating the need for nitro group reduction.
[...] Read more.
We described herein a concise synthesis of 3′,4′-diaminoflavone 10. This new, three-step synthetic approach is more efficient than the conventional seven-step synthetic method. The route is shortened significantly by introducing the amino moieties early and eliminating the need for nitro group reduction. The other two analogues, 5,7-dihydroxy-3′,4′-diaminoflavone 11 and 5,7-dimethoxy-3′,4′-diaminoflavone 12, were also synthesized similarly. The above three compounds, along with flavone, were evaluated for their antioxidant and UVB-protection abilities on zebrafish larvae. The data showed that compound 10 exhibited the best result, with −102.3% of ROS-scavenging rate. Full article
(This article belongs to the Section Medicinal Chemistry)
Open AccessArticle Synthesis and Antibacterial Evaluation of a New Series of N-Alkyl-2-alkynyl/(E)-alkenyl-4-(1H)-quinolones
Molecules 2012, 17(7), 8217-8240; doi:10.3390/molecules17078217
Received: 10 April 2012 / Revised: 12 June 2012 / Accepted: 15 June 2012 / Published: 9 July 2012
Cited by 6 | PDF Full-text (358 KB)
Abstract
To gain further insight into the structural requirements of the aliphatic group at position 2 for their antimycobacterial activity, some N-alkyl-4-(1H)-quinolones bearing position 2 alkynyls with various chain length and triple bond positions were prepared and tested for in vitro
[...] Read more.
To gain further insight into the structural requirements of the aliphatic group at position 2 for their antimycobacterial activity, some N-alkyl-4-(1H)-quinolones bearing position 2 alkynyls with various chain length and triple bond positions were prepared and tested for in vitro antibacterial activity against rapidly-growing strains of mycobacteria, the vaccine strain Mycobacterium bovis BCG, and methicillin-resistant Staphylococcus aureus strains, EMRSA-15 and -16. The compounds were also evaluated for inhibition of ATP-dependent MurE ligase of Mycobacterium tuberculosis. The lowest MIC value of 0.5 mg/L (1.2–1.5 µM) was found against M. fortuitum and M. smegmatis. These compounds displayed no or only weak toxicity to the human lung fibroblast cell line MRC-5 at 100 µM concentration. The quinolone derivatives exhibited pronounced activity against the epidemic MRSA strains (EMRSA-15 and -16) with MIC values of 2–128 mg/L (5.3–364.7 µM), and M. bovis BCG with an MIC value of 25 mg/L (66.0–77.4 µM). In addition, the compounds inhibited the MurE ligase of M. tuberculosis with moderate to weak activity showing IC50 values of 200–774 µM. The increased selectivity towards mycobacterial bacilli with reference to MRC-5 cells observed for 2-alkynyl quinolones compared to their corresponding 2-alkenyl analogues serves to highlight the mycobacterial specific effect of the triple bond. Exploration of a terminal bromine atom at the side chain of N-alkyl-2-(E)-alkenyl-4-(1H)-quinolones showed improved antimycobacterial activity whereas a cyclopropyl residue at N-1 was suggested to be detrimental to antibacterial activity. Full article
(This article belongs to the Section Medicinal Chemistry)
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Open AccessArticle The “Funny” Current (If) Inhibition by Ivabradine at Membrane Potentials Encompassing Spontaneous Depolarization in Pacemaker Cells
Molecules 2012, 17(7), 8241-8254; doi:10.3390/molecules17078241
Received: 21 May 2012 / Revised: 3 July 2012 / Accepted: 4 July 2012 / Published: 9 July 2012
Cited by 9 | PDF Full-text (927 KB)
Abstract
Recent clinical trials have shown that ivabradine (IVA), a drug that inhibits the funny current (If) in isolated sinoatrial nodal cells (SANC), decreases heart rate and reduces morbidity and mortality in patients with cardiovascular diseases. While IVA inhibits If
[...] Read more.
Recent clinical trials have shown that ivabradine (IVA), a drug that inhibits the funny current (If) in isolated sinoatrial nodal cells (SANC), decreases heart rate and reduces morbidity and mortality in patients with cardiovascular diseases. While IVA inhibits If, this effect has been reported at essentially unphysiological voltages, i.e., those more negative than the spontaneous diastolic depolarization (DD) between action potentials (APs). We tested the relative potency of IVA to block If over a wide range of membrane potentials, including those that encompass DD governing to the SANC spontaneous firing rate. A clinically relevant IVA concentration of 3 μM to single, isolated rabbit SANC slowed the spontaneous AP firing rate by 15%. During voltage clamp the maximal If was 18 ± 3 pA/pF (at −120 mV) and the maximal If reduction by IVA was 60 ± 8% observed at −92 ± 4 mV. At the maximal diastolic depolarization (~−60 mV) If amplitude was only −2.9 ± 0.4 pA/pF, and was reduced by only 41 ± 6% by IVA. Thus, If amplitude and its inhibition by IVA at physiologically relevant membrane potentials are substantially less than that at unphysiological (hyperpolarized) membrane potentials. This novel finding more accurately describes how IVA affects SANC function and is of direct relevance to numerical modeling of SANC automaticity. Full article
(This article belongs to the Special Issue Ivabradine)
Open AccessArticle Antioxidant Activity of New Aramide Nanoparticles Containing Redox-Active N-phthaloyl Valine Moieties in the Hepatic Cytochrome P450 System in Male Rats
Molecules 2012, 17(7), 8255-8275; doi:10.3390/molecules17078255
Received: 23 April 2012 / Revised: 7 June 2012 / Accepted: 12 June 2012 / Published: 10 July 2012
Cited by 6 | PDF Full-text (451 KB)
Abstract
We report the synthesis of aramide nanoparticles containing a chiral N-phthaloyl valine moiety and their antioxidant activities on hepatic contents of cytochrome P450, amidopyrene N-demethylase, aniline-4-hyroxylase and induced the hepatic content of cytochrome b5 and nicotinamide adenine dinucleotide phosphate
[...] Read more.
We report the synthesis of aramide nanoparticles containing a chiral N-phthaloyl valine moiety and their antioxidant activities on hepatic contents of cytochrome P450, amidopyrene N-demethylase, aniline-4-hyroxylase and induced the hepatic content of cytochrome b5 and nicotinamide adenine dinucleotide phosphate (NADPH) cytochrome C-reductase. Polymers were obtained as well-separated spherical nanoparticles while highly aggregated particles via H-bonding organization of the aramide-containing pyridine led to a thin layer formation. The effects of the nanoparticles and CCl4 on enzyme activities and thiobarbituric acid reactive substances (TBARS) levels of male rat liver were studied. Pretreatments of rats with the polyamides prior to the administration of CCl4 decreased the hepatic content of the tested enzymes. Doses reduced the toxic effects exerted by (•CCl3) upon the liver through inhibition of the cytochrome P450 system. Inhibition of such metabolizing enzymes could reduce the carcinogenic effects of chemical carcinogens. Full article
(This article belongs to the Section Medicinal Chemistry)
Open AccessArticle Preparative Isolation and Purification of Four Compounds from Cistanches deserticola Y.C. Ma by High-Speed Counter-Current Chromatography
Molecules 2012, 17(7), 8276-8284; doi:10.3390/molecules17078276
Received: 23 May 2012 / Revised: 28 June 2012 / Accepted: 3 July 2012 / Published: 10 July 2012
Cited by 14 | PDF Full-text (263 KB)
Abstract
Following a constituent enrichment step on a silica gel column, four phenyl-ethanoid glycosides were successfully isolated from Cistanches deserticola and purified by preparative high-speed counter-current chromatography (HSCCC) with a two-phase solvent system composed of ethyl acetate-n-butanol-ethanol-water (40:6:6:50, v/v/v/v). A total
[...] Read more.
Following a constituent enrichment step on a silica gel column, four phenyl-ethanoid glycosides were successfully isolated from Cistanches deserticola and purified by preparative high-speed counter-current chromatography (HSCCC) with a two-phase solvent system composed of ethyl acetate-n-butanol-ethanol-water (40:6:6:50, v/v/v/v). A total of 30.9 mg acteoside, 13.0 mg isoacteoside, 12.5 mg syringalide A 3'-α-L-rhamnopyranoside and 7.2 mg 2'-acetylacteoside with purity of higher than 95%, as determined by HPLC-ELSD, were obtained in one-step separation from 297 mg of Cistanche deserticola extract, respectively. Their structures were identified by HR-MS, 1H-NMR and 13C-NMR. Full article
(This article belongs to the Section Natural Products)
Open AccessArticle New Trifluoromethyl Triazolopyrimidines as Anti-Plasmodium falciparum Agents
Molecules 2012, 17(7), 8285-8302; doi:10.3390/molecules17078285
Received: 31 May 2012 / Revised: 27 June 2012 / Accepted: 29 June 2012 / Published: 10 July 2012
Cited by 19 | PDF Full-text (373 KB)
Abstract
According to the World Health Organization, half of the World’s population, approximately 3.3 billion people, is at risk for developing malaria. Nearly 700,000 deaths each year are associated with the disease. Control of the disease in humans still relies on chemotherapy. Drug resistance
[...] Read more.
According to the World Health Organization, half of the World’s population, approximately 3.3 billion people, is at risk for developing malaria. Nearly 700,000 deaths each year are associated with the disease. Control of the disease in humans still relies on chemotherapy. Drug resistance is a limiting factor, and the search for new drugs is important. We have designed and synthesized new 2-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyrimidine derivatives based on bioisosteric replacement of functional groups on the anti-malarial compounds mefloquine and amodiaquine. This approach enabled us to investigate the impact of: (i) ring bioisosteric replacement; (ii) a CF3 group substituted at the 2-position of the [1,2,4]triazolo[1,5-a]pyrimidine scaffold and (iii) a range of amines as substituents at the 7-position of the of heterocyclic ring; on in vitro activity against Plasmodium falciparum. According to docking simulations, the synthesized compounds are able to interact with P. falciparum dihydroorotate dehydrogenase (PfDHODH) through strong hydrogen bonds. The presence of a trifluoromethyl group at the 2-position of the [1,2,4]triazolo[1,5-a]pyrimidine ring led to increased drug activity. Thirteen compounds were found to be active, with IC50 values ranging from 0.023 to 20 µM in the anti-HRP2 and hypoxanthine assays. The selectivity index (SI) of the most active derivatives 5, 8, 11 and 16 was found to vary from 1,003 to 18,478. Full article
(This article belongs to the Section Medicinal Chemistry)
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Open AccessArticle Phylattrin, a New Cytotoxic Xanthone from Calophyllum soulattri
Molecules 2012, 17(7), 8303-8311; doi:10.3390/molecules17078303
Received: 30 May 2012 / Revised: 27 June 2012 / Accepted: 28 June 2012 / Published: 10 July 2012
Cited by 5 | PDF Full-text (258 KB)
Abstract
Our continuing studies on secondary metabolites from the stem bark of Calophyllum soulattri has led to the isolation of another new diprenylated xanthone, phylattrin (1), in addition to five other xanthones and two common sterols. The xanthones are soulattrin (2
[...] Read more.
Our continuing studies on secondary metabolites from the stem bark of Calophyllum soulattri has led to the isolation of another new diprenylated xanthone, phylattrin (1), in addition to five other xanthones and two common sterols. The xanthones are soulattrin (2), caloxanthone C (3), macluraxanthone (4), brasixanthone B (5) and trapezifolixanthone (6) while the sterols are stigmasterol (7) and β-sitosterol (8). The structures of these compounds were determined on the basis of spectroscopic analyses such as 1D and 2D-NMR, HRESIMS, IR and UV. Compounds 17 exhibited moderate cytotoxic activities against SNU-1, HeLa, Hep G2, NCI-H23, K562, Raji, LS174T, IMR-32 and SK-MEL-28 cells. Full article
(This article belongs to the Section Natural Products)
Open AccessArticle From BACE1 Inhibitor to Multifunctionality of Tryptoline and Tryptamine Triazole Derivatives for Alzheimer’s Disease
Molecules 2012, 17(7), 8312-8333; doi:10.3390/molecules17078312
Received: 7 May 2012 / Revised: 25 June 2012 / Accepted: 5 July 2012 / Published: 10 July 2012
Cited by 17 | PDF Full-text (2496 KB)
Abstract
Efforts to discover new drugs for Alzheimer’s disease emphasizing multiple targets was conducted seeking to inhibit amyloid oligomer formation and to prevent radical formation. The tryptoline and tryptamine cores of BACE1 inhibitors previously identified by virtual screening were modified in silico for additional
[...] Read more.
Efforts to discover new drugs for Alzheimer’s disease emphasizing multiple targets was conducted seeking to inhibit amyloid oligomer formation and to prevent radical formation. The tryptoline and tryptamine cores of BACE1 inhibitors previously identified by virtual screening were modified in silico for additional modes of action. These core structures were readily linked to different side chains using 1,2,3-triazole rings as bridges by copper catalyzed azide-alkyne cycloaddition reactions. Three compounds among the sixteen designed compounds exerted multifunctional activities including β-secretase inhibitory action, anti-amyloid aggregation, metal chelating and antioxidant effects at micromolar levels. the neuroprotective effects of the multifunctional compounds 6h, 12c and 12h on Aβ1-42 induced neuronal cell death at 1 μM were significantly greater than those of the potent single target compound, BACE1 inhibitor IV and were comparable to curcumin. The observed synergistic effect resulting from the reduction of the Aβ1-42 neurotoxicity cascade substantiates the validity of our multifunctional strategy in drug discovery for Alzheimer’s disease. Full article
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Open AccessArticle Moringa oleifera Hydroethanolic Extracts Effectively Alleviate Acetaminophen-Induced Hepatotoxicity in Experimental Rats through Their Antioxidant Nature
Molecules 2012, 17(7), 8334-8350; doi:10.3390/molecules17078334
Received: 12 June 2012 / Revised: 25 June 2012 / Accepted: 26 June 2012 / Published: 10 July 2012
Cited by 27 | PDF Full-text (320 KB)
Abstract
The aim of the study was to investigate the in vitro antioxidant properties Moringa oleifera Lam. (MO) extracts and its curative role in acetaminophen (APAP)- induced toxic liver injury in rats caused by oxidative damage. The total phenolic content and antioxidant properties of
[...] Read more.
The aim of the study was to investigate the in vitro antioxidant properties Moringa oleifera Lam. (MO) extracts and its curative role in acetaminophen (APAP)- induced toxic liver injury in rats caused by oxidative damage. The total phenolic content and antioxidant properties of hydroethanolic extracts of different MO edible parts were investigated by employing an established in vitro biological assay. In the antihepatotoxic study, either flowers or leaves extract (200 mg/kg or 400 mg/kg, i.p) were administered an hour after APAP administration, respectively. N-Acetylcysteine was used as the positive control against APAP-induced hepatotoxicity. The levels of liver markers such as alanine aminotransferase (ALT) and the levels of oxidative damage markers including malondialdehyde (MDA), 4-hydroxynonenal (4-HNE) protein adduct, reduced glutathione (GSH), superoxide dismutase (SOD) and catalase (CAT) were analysed and compared between experimental groups. Among MO edible parts the flower extracts contain the highest total phenolic content and antioxidant capacity, followed by leaves extract. The oxidative marker MDA, as well as 4-HNE protein adduct levels were elevated and GSH, SOD and CAT were significantly decreased in groups treated with hepatotoxin. The biochemical liver tissue oxidative markers measured in the rats treated with MO flowers and leaves hydroethanolic extracts showed a significant (p < 0.05) reduction in the severity of the liver damage. The results of this study strongly indicate the therapeutic properties of MO hydroethanolic extracts against acute liver injury and thereby scientifically support its traditional use. Full article
Open AccessCommunication Electrospray Ionization Mass Spectrometric Analysis of Highly Reactive Glycosyl Halides
Molecules 2012, 17(7), 8351-8358; doi:10.3390/molecules17078351
Received: 18 May 2012 / Revised: 21 June 2012 / Accepted: 25 June 2012 / Published: 10 July 2012
PDF Full-text (304 KB) | Supplementary Files
Abstract
Highly reactive glycosyl chlorides and bromides have been analysed by a routine mass spectrometric method using electrospray ionization and lithium salt adduct-forming agents in anhydrous acetonitrile solution, providing salient lithiated molecular ions [M+Li]+, [2M+Li]+etc. The role of other adduct-forming
[...] Read more.
Highly reactive glycosyl chlorides and bromides have been analysed by a routine mass spectrometric method using electrospray ionization and lithium salt adduct-forming agents in anhydrous acetonitrile solution, providing salient lithiated molecular ions [M+Li]+, [2M+Li]+ etc. The role of other adduct-forming salts has also been evaluated. The lithium salt method is useful for accurate mass determination of these highly sensitive compounds. Full article
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Open AccessArticle Organic Bee Pollen: Botanical Origin, Nutritional Value, Bioactive Compounds, Antioxidant Activity and Microbiological Quality
Molecules 2012, 17(7), 8359-8377; doi:10.3390/molecules17078359
Received: 17 May 2012 / Revised: 29 June 2012 / Accepted: 2 July 2012 / Published: 11 July 2012
Cited by 27 | PDF Full-text (492 KB)
Abstract
Organic bee pollen (BP, n = 22) harvested from the Douro International Natural Park (DINP, Portugal) was studied. Nine botanical families were found in the mixture of the samples. The water activity and pH ranged 0.21–0.37 and 4.3–5.2, respectively. The BP analyses averaged
[...] Read more.
Organic bee pollen (BP, n = 22) harvested from the Douro International Natural Park (DINP, Portugal) was studied. Nine botanical families were found in the mixture of the samples. The water activity and pH ranged 0.21–0.37 and 4.3–5.2, respectively. The BP analyses averaged 67.7% carbohydrates, 21.8% crude protein, 5.2% crude fat and 2.9% ash. The energy ranged from 396.4 to 411.1 kcal/100 g. The principal fatty acid found was linolenic, followed by linoleic acid, palmitic acid and oleic acid. The phenolic and flavonoid contents varied from 12.9 to 19.8 mg of gallic acid equivalents/g of extract and from 4.5 to 7.1 mg of catechin equivalents/g of extract, respectively. The scavenger activity and β-carotene bleaching assays values (EC50) were 3.0 ± 0.7 mg/mL and 4.6 mg/mL ± 0.9 mg/mL, respectively. E. coli, sulphite-reducing Clostridia, Salmonella and S. aureus were not found. Since there are studies indicating appreciable differences among BPs from different regions, the full characterization of BP from diverse origins still appears to be a sound research priority in order to obtain reliable data about this beehive product. Full article
(This article belongs to the Section Natural Products)
Open AccessArticle Synthesis of New 1,3,4-Thiadiazole and 1,2,3,4-Oxathiadiazole Derivatives from Carbohydrate Precursors and Study of Their Effect on Tyrosinase Enzyme
Molecules 2012, 17(7), 8378-8396; doi:10.3390/molecules17078378
Received: 1 May 2012 / Revised: 10 July 2012 / Accepted: 10 July 2012 / Published: 11 July 2012
Cited by 5 | PDF Full-text (721 KB)
Abstract
5-(1,2,3,4-Tetrahydroxybutyl)-2-methylfuran-3-carbohydrazide (2) was condensed with a variety of ketones to afford carbohydrazide derivatives 36. Acetylation of 35 afforded the acetyl derivatives 79, while periodate oxidation of 36 afforded the formyl derivatives
[...] Read more.
5-(1,2,3,4-Tetrahydroxybutyl)-2-methylfuran-3-carbohydrazide (2) was condensed with a variety of ketones to afford carbohydrazide derivatives 36. Acetylation of 35 afforded the acetyl derivatives 79, while periodate oxidation of 36 afforded the formyl derivatives 1013. Acid catalyzed condensation of thiosemicarbazide or o-tolylthiosemicarbazide with the prepared aldehydes 1012 gave thiosemicarbazone derivatives 1419. Cyclization of the latter with acetic anhydride afforded 4,5-dihydro-1,3,4-thiadiazolyl derivatives 2025. On the other hand, condensation of p-tosylhydrazine with the prepared aldehydes 1012 afforded p-tosylhydrazone derivatives 2628. Cyclization of 2628 with acetic anhydride afforded 1,2,3,4-oxathiadiazole derivatives 2931 respectively. Moreover, the obtained results regarding to the effect of some of the prepared compounds on tyrosinase enzyme showed that the majority of these compounds having an inhibitory effect; especially compounds 12, 16, 17, and 28. Full article
Open AccessArticle Supercritical Extraction of Lycopene from Tomato Industrial Wastes with Ethane
Molecules 2012, 17(7), 8397-8407; doi:10.3390/molecules17078397
Received: 1 May 2012 / Revised: 3 July 2012 / Accepted: 5 July 2012 / Published: 11 July 2012
Cited by 9 | PDF Full-text (330 KB)
Abstract
Supercritical fluid extraction of all-E-lycopene from tomato industrial wastes (mixture of skins and seeds) was carried out in a semi-continuous flow apparatus using ethane as supercritical solvent. The effect of pressure, temperature, feed particle size, solvent superficial velocity and matrix initial
[...] Read more.
Supercritical fluid extraction of all-E-lycopene from tomato industrial wastes (mixture of skins and seeds) was carried out in a semi-continuous flow apparatus using ethane as supercritical solvent. The effect of pressure, temperature, feed particle size, solvent superficial velocity and matrix initial composition was evaluated. Moreover, the yield of the extraction was compared with that obtained with other supercritical solvents (supercritical CO2 and a near critical mixture of ethane and propane). The recovery of all-E-lycopene increased with pressure, decreased with the increase of the particle size in the initial stages of the extraction and was not practically affected by the solvent superficial velocity. The effect of the temperature was more complex. When the temperature increased from 40 to 60 °C the recovery of all-E-lycopene increased from 80 to 90%. However, for a further increase to 80 °C, the recovery remained almost the same, indicating that some E-Z isomerization could have occurred, as well as some degradation of lycopene. The recovery of all-E-lycopene was almost the same for feed samples with different all-E-lycopene content. Furthermore, when a batch with a higher all-E-lycopene content was used, supercritical ethane and a near critical mixture of ethane and propane showed to be better solvents than supercritical CO2 leading to a faster extraction with a higher recovery of the carotenoid. Full article
(This article belongs to the Special Issue Synthesis and Extraction in Supercritical Fluids)
Open AccessArticle Effect of Gender, Season, and Vitamin D Status on Bone Biochemical Markers in Saudi Diabetes Patients
Molecules 2012, 17(7), 8408-8418; doi:10.3390/molecules17078408
Received: 15 May 2012 / Revised: 4 July 2012 / Accepted: 5 July 2012 / Published: 11 July 2012
Cited by 4 | PDF Full-text (199 KB)
Abstract
Biochemical bone turnover markers (BTMs) provide important information on the diagnosis, therapy and monitoring of metabolic bone diseases. They are evident before measurable changes in bone mineral density (BMD) take place. A total of 35 adult Saudi patients (23 males; 12 females) with
[...] Read more.
Biochemical bone turnover markers (BTMs) provide important information on the diagnosis, therapy and monitoring of metabolic bone diseases. They are evident before measurable changes in bone mineral density (BMD) take place. A total of 35 adult Saudi patients (23 males; 12 females) with type 2 diabetes and diagnosed to be vitamin D deficient were recruited in this prospective study. Here we investigated the effects of gender, season, and vitamin D status on bone biochemical markers of bone remodeling. Anthropometry and blood samples were collected at different intervals. Metabolic parameters and bone biomarkers were measured routinely and by ELISA. Both males and females had a significant increase in their vitamin D status over time, but no significant changes in the bone biomarkers were observed in females. In males there was a significant increase in circulating levels of corrected calcium and OPN (p = 0.004 and 0.01 respectively) and a significant decrease in crosslaps (p = 0.005). In all subjects there was a modest but significant positive relationship between vitamin D status and OC (R = 0.34; p = 0.04). In conclusion, our study demonstrates that changes in bone remodeling markers are affected by season, gender, and possibly vitamin D status. This gender difference may well reflect the physiologic pathway responsible for the higher peak bone mass achieved in males compared to females. Full article
Open AccessArticle Evaluation of Antioxidant and Immunity-Enhancing Activities of Sargassum pallidum Aqueous Extract in Gastric Cancer Rats
Molecules 2012, 17(7), 8419-8429; doi:10.3390/molecules17078419
Received: 23 May 2012 / Revised: 28 June 2012 / Accepted: 29 June 2012 / Published: 11 July 2012
Cited by 17 | PDF Full-text (202 KB)
Abstract
The effect of Sargassum pallidum (brown seaweed) aqueous extract on the immunity function and antioxidant activities in was studied gastric cancer rats. Treatment with Sargassum pallidum aqueous extract at oral doses 400, 600 or 800 mg/kg body weight was found to provide a
[...] Read more.
The effect of Sargassum pallidum (brown seaweed) aqueous extract on the immunity function and antioxidant activities in was studied gastric cancer rats. Treatment with Sargassum pallidum aqueous extract at oral doses 400, 600 or 800 mg/kg body weight was found to provide a dose-dependent protection against N-methyl-N′-nitro-N-nitrosoguanidine (MNNG)-induced immunity damage and oxidative injury by enhancing serum interleukin-2 (IL-2), interleukin-4 (IL-4), interleukin-10 (IL-10) levels, decreasing interleukin-6 (IL-6), interleukin-1β (IL-1β), tumor necrosis factor-alpha (TNF-α) levels, preserving normal antioxidant enzymes activities, and by inhibiting lipid peroxidation in gastric mucosa. It can be concluded that Sargassum pallidum aqueous extract may enhance the immunity and antioxidant activities in gastric cancer rats. Full article
Open AccessArticle Aqueous Synthesis and Characterization of TGA-capped CdSe Quantum Dots at Freezing Temperature
Molecules 2012, 17(7), 8430-8438; doi:10.3390/molecules17078430
Received: 9 May 2012 / Revised: 30 June 2012 / Accepted: 2 July 2012 / Published: 11 July 2012
Cited by 13 | PDF Full-text (615 KB)
Abstract
CdSe quantum dots (QDs) have traditionally been synthesized in organic phase and then transferred to aqueous solution by functionalizing their surface with silica, polymers, short-chain thiol ligands, or phospholipid micelles. However, a drastic increase in the hydrodynamic size and biotoxicity of QDs may
[...] Read more.
CdSe quantum dots (QDs) have traditionally been synthesized in organic phase and then transferred to aqueous solution by functionalizing their surface with silica, polymers, short-chain thiol ligands, or phospholipid micelles. However, a drastic increase in the hydrodynamic size and biotoxicity of QDs may hinder their biomedical applications. In this paper, the TGA-capped CdSe QDs are directly synthesized in aqueous phase at freezing temperature, and they prove to possess high QY (up to 14%). Full article
Open AccessArticle Antifungal Activity, Toxicity and Chemical Composition of the Essential Oil of Coriandrum sativum L. Fruits
Molecules 2012, 17(7), 8439-8448; doi:10.3390/molecules17078439
Received: 15 April 2012 / Revised: 22 June 2012 / Accepted: 30 June 2012 / Published: 11 July 2012
Cited by 13 | PDF Full-text (184 KB)
Abstract
The aims of this study were to test the antifungal activity, toxicity and chemical composition of essential oil from C. sativum L. fruits. The essential oil, obtained by hydro-distillation, was analyzed by gas chromatography/mass spectroscopy. Linalool was the main constituent (58.22%). The oil
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The aims of this study were to test the antifungal activity, toxicity and chemical composition of essential oil from C. sativum L. fruits. The essential oil, obtained by hydro-distillation, was analyzed by gas chromatography/mass spectroscopy. Linalool was the main constituent (58.22%). The oil was considered bioactive, showing an LC50 value of 23 µg/mL in the Artemia salina lethality test. The antifungal activity was evaluated against Microsporum canis and Candida spp. by the agar-well diffusion method and the minimum inhibitory concentration (MIC) and the minimum fungicidal concentration (MFC) were established by the broth microdilution method. The essential oil induced growth inhibition zones of 28 ± 5.42 and 9.25 ± 0.5 for M. canis and Candida spp. respectively. The MICs and MFCs for M. canis strains ranged from 78 to 620 and 150 to 1,250 µg/mL, and the MICs and MFCs for Candida spp strains ranged from 310 to 620 and 620 to 1,250 µg/mL, respectively. C. sativum essential oil is active in vitro against M. canis and Candida spp. demonstrating good antifungal activity. Full article
(This article belongs to the collection Bioactive Compounds)
Open AccessArticle Uses of Cyanoacetylhydrazine in Heterocyclic Synthesis: Novel Synthesis of Pyrazole Derivatives with Anti-tumor Activities
Molecules 2012, 17(7), 8449-8463; doi:10.3390/molecules17078449
Received: 29 May 2012 / Revised: 22 June 2012 / Accepted: 26 June 2012 / Published: 12 July 2012
Cited by 13 | PDF Full-text (227 KB)
Abstract
The reaction of cyanoacetylhydrazine with chloroacetyl chloride gave N'-(2-chloroacetyl)-2-cyanoacetohydrazide. The latter underwent cyclization to afford 1-(5 amino-3-hydroxy-1H-pyrazol-1-yl)-2-chloroethanone, which underwent nucleophilic substitution to give 3-(5-amino-3-hydroxy-1H-pyrazol-1-yl)-3-oxopropanenitrile. The latter two compounds were used as key synthons to synthesize new thiophene, pyran, thiazole and
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The reaction of cyanoacetylhydrazine with chloroacetyl chloride gave N'-(2-chloroacetyl)-2-cyanoacetohydrazide. The latter underwent cyclization to afford 1-(5 amino-3-hydroxy-1H-pyrazol-1-yl)-2-chloroethanone, which underwent nucleophilic substitution to give 3-(5-amino-3-hydroxy-1H-pyrazol-1-yl)-3-oxopropanenitrile. The latter two compounds were used as key synthons to synthesize new thiophene, pyran, thiazole and some fused heterocyclic derivatives. The antitumor activity of the newly synthesized compounds was evaluated against three human tumor cells lines, namely breast adenocarcinoma (MCF-7), non-small cell lung cancer (NCI-H460) and CNS cancer (SF-268) and some of these compounds were found to exhibit much higher inhibitory effects towards the three tumor cell lines than the Gram positive control doxorubicin. Full article
(This article belongs to the Section Medicinal Chemistry)
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Open AccessArticle Enzymatic Reduction of 9-Methoxytariacuripyrone by Saccharomyces cerevisiae and Its Antimycobacterial Activity
Molecules 2012, 17(7), 8464-8470; doi:10.3390/molecules17078464
Received: 11 May 2012 / Revised: 5 July 2012 / Accepted: 5 July 2012 / Published: 12 July 2012
Cited by 4 | PDF Full-text (185 KB)
Abstract
Biotransformation processes have been successfully utilized to obtain products of pharmaceutical, chemical, food, and agricultural interest, which are difficult to obtain by classic chemical methods. The compound with antituberculous activity, 9-methoxy-tariacuripyrone (1), isolated from Aristolochia brevipes, was submitted to biotransformation
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Biotransformation processes have been successfully utilized to obtain products of pharmaceutical, chemical, food, and agricultural interest, which are difficult to obtain by classic chemical methods. The compound with antituberculous activity, 9-methoxy-tariacuripyrone (1), isolated from Aristolochia brevipes, was submitted to biotransformation with the yeast Saccharomyces cerevisiae under culture, yielding 5-amino-9-methoxy-3,4-dihydro-2H-benzo[h]chromen-2-one (2). The structure of 2 was elucidated on the basis of spectroscopic analyses. The results mainly show the reduction of the double bond and the nitro group of compound 1. Metabolite 2 demonstrated an increase in anti-tuberculous activity (MIC = 3.12 µg/mL) against the drug-sensitive Mycobacterium tuberculosis (H37Rv) strain, with respect to that shown by 1. Full article
(This article belongs to the Section Natural Products)
Open AccessArticle Antimycobacterial Activity of Constituents from Foeniculum vulgare Var. Dulce Grown in Mexico
Molecules 2012, 17(7), 8471-8482; doi:10.3390/molecules17078471
Received: 21 May 2012 / Revised: 19 June 2012 / Accepted: 19 June 2012 / Published: 13 July 2012
Cited by 10 | PDF Full-text (185 KB)
Abstract
Bioassay guided fractionation of an antimycobacterial extract of Foeniculum vulgare var dulce (Apiaceae) led to the isolation and characterization of 5-hydroxyfurano-coumarin. The chemical structure of this compound was elucidated by 1H and 13C (1D and 2D) Nuclear Magnetic Resonance (NMR) spectroscopy.
[...] Read more.
Bioassay guided fractionation of an antimycobacterial extract of Foeniculum vulgare var dulce (Apiaceae) led to the isolation and characterization of 5-hydroxyfurano-coumarin. The chemical structure of this compound was elucidated by 1H and 13C (1D and 2D) Nuclear Magnetic Resonance (NMR) spectroscopy. In addition, the active fractions were analyzed by GC-MS and seventy eight compounds were identified; the major compounds were 1,3-benzenediol, 1-methoxycyclohexene, o-cymene, sorbic acid, 2-hydroxy-3-methyl-2-cyclopenten-1-one, estragole, limonene-10-ol and 3-methyl-2-cyclopenten-1-one. Twenty compounds identified in the active fractions were tested against one sensitive and three MDR strains of Mycobacterium tuberculosis using the Alamar Blue microassay. Compounds that showed some degree of antimycobacterial activity against all strains tested were the following: linoleic acid (MIC 100 µg/mL), oleic acid (MIC 100 µg/mL), 1,3-benzenediol (MIC 100–200 µg/mL), undecanal (MIC 50–200 µg/mL), and 2,4-undecadienal (MIC 25–50 µg/mL), the last being the most active compound. To our knowledge, this is the first report of the presence of 5-hydroxy-furanocoumarin in F. vulgare. Full article
Open AccessArticle Synthesis, Tautomeric Structure and Antimicrobial Activity of 3-Arylhydrazono-4-phenyl-[1,2,4]-triazepino[2,3-a]quinazoline-2,7(1H)-diones
Molecules 2012, 17(7), 8483-8493; doi:10.3390/molecules17078483
Received: 24 May 2012 / Revised: 25 June 2012 / Accepted: 3 July 2012 / Published: 13 July 2012
Cited by 6 | PDF Full-text (213 KB)
Abstract
A simple strategy for the synthesis of the hitherto unreported 3-arylazo-4-phenyl- [1,2,4]triazepino[2,3-a]quinazoline-2,7(1H)-diones is described. Spectral data indicated that the studied compounds exist predominantly in the hydrazone tautomeric form. The antimicrobial activity of the newly synthesized compounds was also evaluated.
[...] Read more.
A simple strategy for the synthesis of the hitherto unreported 3-arylazo-4-phenyl- [1,2,4]triazepino[2,3-a]quinazoline-2,7(1H)-diones is described. Spectral data indicated that the studied compounds exist predominantly in the hydrazone tautomeric form. The antimicrobial activity of the newly synthesized compounds was also evaluated. The results indicated that some of these compounds have moderate activity towards bacteria. Full article
(This article belongs to the Section Organic Synthesis)
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Open AccessArticle Influence of ShuJinHuoXue Tablets on Ischemia Reperfusion Injury of Animals’ Skeletal Muscle
Molecules 2012, 17(7), 8494-8505; doi:10.3390/molecules17078494
Received: 21 May 2012 / Revised: 27 June 2012 / Accepted: 6 July 2012 / Published: 16 July 2012
Cited by 3 | PDF Full-text (315 KB)
Abstract
Ischemia-reperfusion (IR) can lead to serious tissue oxidative injury in animals. ShuJinHuoXue tablet (SJHXT) is a Chinese Traditional Medicine which can relax the muscles and stimulate the blood circulation and has been used as a clinical medicine. In the present study, we investigated
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Ischemia-reperfusion (IR) can lead to serious tissue oxidative injury in animals. ShuJinHuoXue tablet (SJHXT) is a Chinese Traditional Medicine which can relax the muscles and stimulate the blood circulation and has been used as a clinical medicine. In the present study, we investigated the effects of SJHXT pretreatment on oxidative injury using an animal model of acute limb IR. Results showed that SJHXT pre-treatment (200, 300 and 400 mg/kg/day) markedly reduced serum endothelin-1 (ET-1), thromboxane B2 (TXB2) levels and thromboxane B2/6-keto- prostaglandin F1α (TXB2/6-Keto-PGF), wet weight/dried weight (W/D) ratio, myeloperoxidase (MPO), creatine kinase (CK), lactate dehydrogenase (LDH) activities, and increased serum nitric oxide (NO), 6-Keto-PGF levels and NO/ET-1 ratio in the IR+SJHXT groups. In addition, the SJHXT pre-treatment (200, 300 and 400 mg/kg/day) markedly reduced skeletal muscle Ca2+, malondialdehyde (MDA) levels, increased Na+-K+-ATPase, Ca2+-Mg2+-ATPase, superoxide dismutase (SOD), catalase (CAT), and glutathione peroxidase (GSH-Px) activities. Our results suggest that SJHXT pre-treatment may improve skeletal muscle blood vessel microcirculation, decrease skeletal muscle oxidative injury and enhance antioxidant enzymes activities in IR animals. Full article
Open AccessArticle Green Biosynthesis of Silver Nanoparticles Using Callicarpa maingayi Stem Bark Extraction
Molecules 2012, 17(7), 8506-8517; doi:10.3390/molecules17078506
Received: 8 June 2012 / Revised: 20 June 2012 / Accepted: 21 June 2012 / Published: 16 July 2012
Cited by 59 | PDF Full-text (586 KB)
Abstract
Different biological methods are gaining recognition for the production of silver nanoparticles (Ag-NPs) due to their multiple applications. The use of plants in the green synthesis of nanoparticles emerges as a cost effective and eco-friendly approach. In this study the green biosynthesis of
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Different biological methods are gaining recognition for the production of silver nanoparticles (Ag-NPs) due to their multiple applications. The use of plants in the green synthesis of nanoparticles emerges as a cost effective and eco-friendly approach. In this study the green biosynthesis of silver nanoparticles using Callicarpa maingayi stem bark extract has been reported. Characterizations of nanoparticles were done using different methods, which include; ultraviolet-visible spectroscopy (UV-Vis), powder X-ray diffraction (XRD), transmission electron microscopy (TEM), scanning electron microscopy (SEM), energy dispersive X-ray fluorescence (EDXF) spectrometry, zeta potential measurements and Fourier transform infrared (FT-IR) spectroscopy. UV-visible spectrum of the aqueous medium containing silver nanoparticles showed absorption peak at around 456 nm. The TEM study showed that mean diameter and standard deviation for the formation of silver nanoparticles were 12.40 ± 3.27 nm. The XRD study showed that the particles are crystalline in nature, with a face centered cubic (fcc) structure. The most needed outcome of this work will be the development of value added products from Callicarpa maingayi for biomedical and nanotechnology based industries. Full article
Open AccessArticle Preparation and Preliminary Biological Evaluation of Novel 99mTc-Labelled Thymidine Analogs as Tumor Imaging Agents
Molecules 2012, 17(7), 8518-8532; doi:10.3390/molecules17078518
Received: 18 May 2012 / Revised: 27 June 2012 / Accepted: 5 July 2012 / Published: 16 July 2012
Cited by 3 | PDF Full-text (283 KB)
Abstract
Two kinds of novel thymidine derivatives, N-thymidine-yl-N′-methyl-N′-{N′′-[2-sulfanyl-(ethylamino)acetyl]-2-aminoethylsulfanyl-1-hexanamide}-ethanediamine (TMHEA) and N-thymidine-yl-N′-methyl-N′-{N′′-[2-sulfanyl-(ethylamino)acetyl]-2-aminoethylsulfanyl-1-hexanamide}-hexanediamine (TMHHA) were prepared and successfully labeled with 99mTc in high labeling yields. The in vitro stability and in
[...] Read more.
Two kinds of novel thymidine derivatives, N-thymidine-yl-N′-methyl-N′-{N′′-[2-sulfanyl-(ethylamino)acetyl]-2-aminoethylsulfanyl-1-hexanamide}-ethanediamine (TMHEA) and N-thymidine-yl-N′-methyl-N′-{N′′-[2-sulfanyl-(ethylamino)acetyl]-2-aminoethylsulfanyl-1-hexanamide}-hexanediamine (TMHHA) were prepared and successfully labeled with 99mTc in high labeling yields. The in vitro stability and in vivo biodistribution of 99mTc-TMHEA and 99mTc-TMHHA were investigated and compared. The biodistribution studies indicate that the radiotracer 99mTc-TMHEA displays selective tumor uptake, suggesting it is a potential tumor imaging agent. Full article
Open AccessArticle Reactivity of Ruthenium Vinylidene Complexes Containing Indenyl/dppe Ligands and Unsaturated Bonds at Cd with Trimethylsilyl Azide
Molecules 2012, 17(7), 8533-8553; doi:10.3390/molecules17078533
Received: 13 June 2012 / Revised: 5 July 2012 / Accepted: 6 July 2012 / Published: 17 July 2012
Cited by 1 | PDF Full-text (442 KB)
Abstract
This study presents a new reaction of cationic vinylidene complexes with Me3SiN3 (TMSN3), which yields N-coordinated nitrile complexes 3. Treatment of a ruthenium acetylide precursor containing indenyl and dppe ligands with a series of organic halides
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This study presents a new reaction of cationic vinylidene complexes with Me3SiN3 (TMSN3), which yields N-coordinated nitrile complexes 3. Treatment of a ruthenium acetylide precursor containing indenyl and dppe ligands with a series of organic halides produced the corresponding vinylidene complexes 2 in good yield. Further reaction of 2 with TMSN3 at room temperature produced N-coordinated ruthenium nitrile complexes 3. Unlike the reaction of cyclopropenylruthenium complexes with TMSN3, which yielded different products depending on the substituent at Cγ, the vinylidene complexes containing unsaturated bonds at Cd yielded similar N-coordinated nitrile complexes. This transformation did not seemingly occur in the reaction of ruthenium vinylidene complexes containing Cp and PPh3 ligands with TMSN3. Deprotonation of these vinylidene complexes yielded cyclopropenyl or thermodynamic furylruthenium complexes, depending on the substitute at Cγ. Subsequent reactions of the cyclopropenyl or furylruthenium complexes with TMSN3 afforded different products. Full article
Open AccessArticle Two New Oxysporone Derivatives from the Fermentation Broth of the Endophytic Plant Fungus Pestalotiopsis karstenii Isolated from Stems of Camellia sasanqua
Molecules 2012, 17(7), 8554-8560; doi:10.3390/molecules17078554
Received: 5 June 2012 / Revised: 30 June 2012 / Accepted: 5 July 2012 / Published: 17 July 2012
Cited by 5 | PDF Full-text (198 KB) | Supplementary Files
Abstract
Two new oxysporone derivatives, pestalrone A (1) and pestalrone B (2), along with two known structurally related compounds 3,4, were from the fermentation broth of the endophytic plant fungus Pestalotiopsis karstenii isolated from stems of Camellia
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Two new oxysporone derivatives, pestalrone A (1) and pestalrone B (2), along with two known structurally related compounds 3,4, were from the fermentation broth of the endophytic plant fungus Pestalotiopsis karstenii isolated from stems of Camellia sasanqua. Their structures and relative configurations were elucidated by extensive spectroscopic analysis and comparison of chemical shifts with related known compounds. Compound 2 exhibited significant activities agains HeLa, HepG2 and U-251 with IC50 values of 12.6, 31.7 and 5.4 µg/mL, respectively. Full article
Open AccessArticle Comprehensive Study of Honey with Protected Denomination of Origin and Contribution to the Enhancement of Legal Specifications
Molecules 2012, 17(7), 8561-8577; doi:10.3390/molecules17078561
Received: 29 May 2012 / Revised: 28 June 2012 / Accepted: 5 July 2012 / Published: 17 July 2012
Cited by 8 | PDF Full-text (325 KB)
Abstract
In this study the characterization of a total of 60 honey samples with Protected Denomination of Origin (PDO) collected over three harvests (2009–2011, inclusive), from the Northeast of Portugal was carried out based on the presence of pollen, physicochemical and microbiological characteristics. All
[...] Read more.
In this study the characterization of a total of 60 honey samples with Protected Denomination of Origin (PDO) collected over three harvests (2009–2011, inclusive), from the Northeast of Portugal was carried out based on the presence of pollen, physicochemical and microbiological characteristics. All samples were found to meet the European Legislation, but some didn’t meet the requirements of the PDO specifications. Concerning the floral origin of honey, our results showed the prevalence of rosemary (Lavandula pedunculata) pollen. The microbiological quality of all the analyzed samples was satisfactory, since fecal coliforms, sulfite-reducing clostridia and Salmonella were absent, and molds and yeasts were detected in low counts. Significant differences between the results were studied using one-way analysis of variance (ANOVA), followed by Tukey’s HSD test. The samples were submitted to discriminant function analysis, in order to determine which variables differentiate between two or more naturally occurring groups (Forward Stepwise Analysis). The variables selected were in this order: diastase activity, pH, reducing sugars, free acidity and HMF. The pollen spectrum has perfect discriminatory power. This is the first study in which a honey with PDO was tested, in order to assess its compliance with the PDO book of specifications. Full article
(This article belongs to the Section Natural Products)
Open AccessArticle A Facile and Efficient Procedure for the Synthesis of New Benzimidazole-2-thione Derivatives
Molecules 2012, 17(7), 8578-8586; doi:10.3390/molecules17078578
Received: 4 May 2012 / Revised: 27 June 2012 / Accepted: 9 July 2012 / Published: 17 July 2012
PDF Full-text (170 KB)
Abstract
A series of benzimidazole-2-thione derivatives was synthesized using a reaction between the macrocyclic aminal 16H,13H-5:12,7:14-dimethanedibenzo[d,i]-[1,3,6,8] tetraazecine (DMDBTA, 5) and various nucleophiles in the presence of carbon disulfide. A full chemical characterization using IR, 1H-, 13
[...] Read more.
A series of benzimidazole-2-thione derivatives was synthesized using a reaction between the macrocyclic aminal 16H,13H-5:12,7:14-dimethanedibenzo[d,i]-[1,3,6,8] tetraazecine (DMDBTA, 5) and various nucleophiles in the presence of carbon disulfide. A full chemical characterization using IR, 1H-, 13C-NMR and GC-MS analyses of the new compounds is provided. These compounds were separated from the reaction mixture by column chromatography (CC) in highly pure form in 15%–51.4% yield. Full article
(This article belongs to the Section Organic Synthesis)
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Open AccessArticle Effect of Curing Agent and Temperature on the Rheological Behavior of Epoxy Resin Systems
Molecules 2012, 17(7), 8587-8594; doi:10.3390/molecules17078587
Received: 15 May 2012 / Revised: 7 July 2012 / Accepted: 10 July 2012 / Published: 17 July 2012
Cited by 5 | PDF Full-text (205 KB)
Abstract
The effect of curing agent (6610) content and temperature on the rheological behavior of the epoxy resin CYD-128 was studied by DSC analysis and viscosity experiments. The results show that the resin system meets the requirements of processing technology. A complete reaction occurs
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The effect of curing agent (6610) content and temperature on the rheological behavior of the epoxy resin CYD-128 was studied by DSC analysis and viscosity experiments. The results show that the resin system meets the requirements of processing technology. A complete reaction occurs when the curing agent content (40 parts per hundred resin, phr) is a little higher than the theoretical value (33.33 phr), while the degree of reaction of the resin system is reduced when the curing agent content is lower (25.00 phr) than theoretical value. However, excessive curing agent (50.00 phr) results in a lower reaction rate. Curing agent content has little influence on gel time when curing agent content exceeded 33.33 phr and the temperature was less than 70 °C. The isothermal viscosity-time curves shift towards the –x axis when the temperature rises from 50 °C to 80 °C. Meanwhile, higher temperature results in higher reaction rates. Full article
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Open AccessArticle Effect of β-Carotene on Immunity Function and Tumour Growth in Hepatocellular Carcinoma Rats
Molecules 2012, 17(7), 8595-8603; doi:10.3390/molecules17078595
Received: 15 May 2012 / Revised: 26 June 2012 / Accepted: 5 July 2012 / Published: 18 July 2012
Cited by 2 | PDF Full-text (392 KB)
Abstract
The aim of the present study was to investigate the anticancer and immunity activity of β-carotene in hepatocellular carcinoma (HCC) rats. Three days after transplantation, forty Wistar rats were randomly divided into four groups, each group consisting of 10 animals. These groups were
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The aim of the present study was to investigate the anticancer and immunity activity of β-carotene in hepatocellular carcinoma (HCC) rats. Three days after transplantation, forty Wistar rats were randomly divided into four groups, each group consisting of 10 animals. These groups were control group (untreated), low-dose β-carotene-treated group (20 mg/kg), middle-dose group (40 mg/kg) and high-dose (60 mg/kg) group. β-Carotene-treated groups were fed with β-carotene (20, 40, 60 mg/kg b.w.) orally for 30 days. Control group was treated with the same volume of physiological saline. Another ten rats were served as the normal group. Results showed that 30 days of β-carotene treatment could significantly inhibit tumour growth, enhance blood NK, IL-2, TNF-α, WBC, TP, ALB and A/G levels, and decrease blood ALT, AST and ALP activities in HCC rats. Pathological analysis of liver tissue showed that β-carotene treatment may decrease damage of liver tissue in HCC rats. It can be concluded that β-carotene may improve the immunity function and inhibit tumour growth in HCC rats. Full article
Open AccessCommunication IBS-Catalyzed Regioselective Oxidation of Phenols to 1,2-Quinones with Oxone®
Molecules 2012, 17(7), 8604-8616; doi:10.3390/molecules17078604
Received: 25 June 2012 / Revised: 6 July 2012 / Accepted: 12 July 2012 / Published: 18 July 2012
Cited by 23 | PDF Full-text (318 KB)
Abstract
We have developed the first example of hypervalent iodine(V)-catalyzed regioselective oxidation of phenols to o-quinones. Various phenols could be oxidized to the corresponding o-quinones in good to excellent yields using catalytic amounts of sodium salts of 2-iodobenzenesulfonic acids (pre-IBSes)
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We have developed the first example of hypervalent iodine(V)-catalyzed regioselective oxidation of phenols to o-quinones. Various phenols could be oxidized to the corresponding o-quinones in good to excellent yields using catalytic amounts of sodium salts of 2-iodobenzenesulfonic acids (pre-IBSes) and stoichiometric amounts of Oxone® as a co-oxidant under mild conditions. The reaction rate of IBS-catalyzed oxidation under nonaqueous conditions was further accelerated in the presence of an inorganic base such as potassium carbonate (K2CO3), a phase transfer catalyst such as tetrabutylammonium hydrogen sulfate (nBu4NHSO4), and a dehydrating agent such as anhydrous sodium sulfate (Na2SO4). Full article
(This article belongs to the Special Issue Hypervalent Compounds)
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Open AccessArticle Metabolism of Tanshinone IIA, Cryptotanshinone and Tanshinone I from Radix Salvia Miltiorrhiza in Zebrafish
Molecules 2012, 17(7), 8617-8632; doi:10.3390/molecules17078617
Received: 25 June 2012 / Revised: 9 July 2012 / Accepted: 10 July 2012 / Published: 18 July 2012
Cited by 8 | PDF Full-text (768 KB)
Abstract
The study aimed to investigate the potential of zebrafish in imitating mammal phase I metabolism of natural compounds. Three diterpenoid quinones from Radix Salvia miltiorrhiza, namely tanshinone IIA (TIIA), cryptotanshinone (Cry) and tanshinone I (TI) were selected as model compounds, and their metabolites
[...] Read more.
The study aimed to investigate the potential of zebrafish in imitating mammal phase I metabolism of natural compounds. Three diterpenoid quinones from Radix Salvia miltiorrhiza, namely tanshinone IIA (TIIA), cryptotanshinone (Cry) and tanshinone I (TI) were selected as model compounds, and their metabolites mediated by zebrafish were characterized using a high-performance liquid chromatography coupled ion-trap mass spectrometry (HPLC/IT-MSn) method with electrospray ionization in positive mode. The separation was performed with a Zorbax C-18 column using a binary gradient elution of 0.05% formic acid acetonitrile/0.05% formic acid water. According to the MS spectra and after comparison with reference standards and literature reports, hydroxylation, dehydrogenation or D-ring hydrolysis metabolites of TIIA and Cry but not of TI were characterized, which coincided with those reported using regular in vivo or in vitro metabolic analysis methods, thus verifying that zebrafish can successfully imitate mammalian phase I metabolism which instills further confidence in using zebrafish as a novel and prospective metabolism model. Full article
(This article belongs to the Section Medicinal Chemistry)
Open AccessArticle Anti-Hepatitis B Virus Activity of Chickweed [Stellaria media (L.) Vill.] Extracts in HepG2.2.15 Cells
Molecules 2012, 17(7), 8633-8646; doi:10.3390/molecules17078633
Received: 22 May 2012 / Revised: 29 June 2012 / Accepted: 9 July 2012 / Published: 18 July 2012
Cited by 7 | PDF Full-text (827 KB)
Abstract
Stellaria media (Linn.) Villars is a traditional Chinese medicine that has been used for over 200 years, mainly for the treatment of dermatitis and other skin diseases. It has also been used as an anti-viral agent. All the fresh chickweed juice samples used
[...] Read more.
Stellaria media (Linn.) Villars is a traditional Chinese medicine that has been used for over 200 years, mainly for the treatment of dermatitis and other skin diseases. It has also been used as an anti-viral agent. All the fresh chickweed juice samples used in this study were prepared using macroporous resin and ultrafiltration technology. The anti-hepatitis B virus (HBV) activity of S. media was evaluated in vitro using the human HBV-transfected liver cell line HepG2.2.15. The concentrations of hepatitis B surface antigen (HBsAg) and hepatitis B e antigen (HBeAg) in HepG2.2.15 cell culture medium were determined by enzyme-linked immunosorbent assay (ELISA) after S. media-n (SM-n) treatment for 6 or 9 days. HBV DNA was quantified using transcription-mediated amplification and real-time polymerase chain reaction. In HepG2.2.15 cells, 30 μg/mL SM-3 effectively suppressed the secretion of HBsAg and HBeAg with inhibition rates of 27.92% and 25.35% after 6 days of treatment, respectively. Consistent with the reduction in HBV antigens, SM-3 also reduced the level of HBV DNA in a dose-dependent manner. The characterization and quantitation of the chemical composition of SM-3 showed the presence of flavonoid C-glycosides, polysaccharides, and protein, which exhibited diverse antiviral activities. In conclusion, our results demonstrate that SM-3 possesses potential anti-HBV activity in vitro. This is the first report demonstrating the anti-HBV effects of S. media, which is currently under early development as a potential anti-HBV drug candidate. Full article
(This article belongs to the Section Natural Products)
Open AccessArticle Solid-State Synthesis of Poly(3',4'-dimethoxy-2,2':5',2"- terthiophene): Comparison With Poly(terthiophene) and Poly(3',4'-ethylenedioxy-2,2':5',2"- terthiophene)
Molecules 2012, 17(7), 8647-8660; doi:10.3390/molecules17078647
Received: 18 May 2012 / Revised: 27 June 2012 / Accepted: 13 July 2012 / Published: 23 July 2012
Cited by 5 | PDF Full-text (532 KB)
Abstract
A new terthiophene monomer: 3',4'-dimethoxy-2,2':5',2"-terthiophene (TMT) was synthesized and characterized by 1H-NMR, 13C-NMR and FTIR. The solid-state oxidative polymerizations of TMT were performed in various ratios of oxidant (FeCl3) to monomer (TMT). The resulting polymers were characterized by 1
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A new terthiophene monomer: 3',4'-dimethoxy-2,2':5',2"-terthiophene (TMT) was synthesized and characterized by 1H-NMR, 13C-NMR and FTIR. The solid-state oxidative polymerizations of TMT were performed in various ratios of oxidant (FeCl3) to monomer (TMT). The resulting polymers were characterized by 1H-NMR, FTIR, UV-vis-NIR, GPC, X-ray diffraction, CV, as well as TGA and conductivity measurements. The structure and properties of poly (TMT) were compared with those of polyterthiophene [poly(TT)] and poly (3',4'-ethylenedioxy-2,2':5',2"-terthiophene) [poly(TET)] prepared under the same polymerization conditions. After comparative analysis with poly(TT) and poly(TET), the effects of the dimethoxy substituent and FeCl3 on the structural and physicochemical properties of the poly(TMT)s were discussed in depth. The comparison suggested that the dimethoxy-substituted polymer did not display higher crystallinity, thermal stability, conductivity and electrochemical activity than ethylenedioxy substituted one. The results also showed that the effect of FeCl3 on poly(TMT) was similar that seen with the poly(TT), in which the oxidation degree, electrochemical activity and conductivity increased steadily with increasing [FeCl3]/[TT] ratio. Furthermore, the poly(TMT) and poly(TT) are mostly made up of dimers with a small amount of higher molecular weight components. Full article
(This article belongs to the Section Organic Synthesis)
Open AccessArticle Synthesis, Characterization, Antibacterial and Antifungal Evaluation of Novel Monosaccharide Esters
Molecules 2012, 17(7), 8661-8673; doi:10.3390/molecules17078661
Received: 13 April 2012 / Revised: 5 July 2012 / Accepted: 16 July 2012 / Published: 23 July 2012
Cited by 5 | PDF Full-text (248 KB)
Abstract
A novel series of 3-(2-furyl)acrylate monosaccharide esters Iaf and menthyloxycarbonyl monosaccharide esters IIaf were designed and synthesized. The chemical structures of the target compounds were confirmed by IR, 1H- and 13C-NMR and ESI-MS, and the target compounds
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A novel series of 3-(2-furyl)acrylate monosaccharide esters Iaf and menthyloxycarbonyl monosaccharide esters IIaf were designed and synthesized. The chemical structures of the target compounds were confirmed by IR, 1H- and 13C-NMR and ESI-MS, and the target compounds were investigated for their in vitro antibacterial and antifungal activities. The antibacterial screening results showed that the 3-(2-furyl)acrylate monosaccharide ester derivatives Iaf were either inactive or only weakly active against the three Gram-positive bacterial strains tested, whereas the menthyloxycarbonyl monosaccharide ester derivatives IIaf exhibited higher levels of activity, with compound IIe being especially potent. The results of the antifungal screening revealed that compounds Ib, Ie, IIb and IIc displayed potent in vitro activities, whereas If and IIf showed promising activities against all of the microorganisms tested, with If exhibiting levels of activity deserving of further investigation. Full article
Open AccessArticle Ultrasound-Promoted One-Pot, Three-Component Synthesis of Spiro[indoline-3,1'-pyrazolo[1,2-b]phthalazine] Derivatives
Molecules 2012, 17(7), 8674-8686; doi:10.3390/molecules17078674
Received: 8 June 2012 / Revised: 28 June 2012 / Accepted: 13 July 2012 / Published: 23 July 2012
Cited by 11 | PDF Full-text (252 KB)
Abstract
A series of 3'-aminospiro[indoline-3,1'-pyrazolo[1,2-b]phthalazine]-2,5',10'-trione derivatives have been synthesized by a one-pot three-component reaction of isatin, malononitrile or ethyl cyanoacetate and phthalhydrazide catalyzed by piperidine under ultrasound irradiation. For comparison the reactions were carried out under both conventional and ultrasonic conditions. In
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A series of 3'-aminospiro[indoline-3,1'-pyrazolo[1,2-b]phthalazine]-2,5',10'-trione derivatives have been synthesized by a one-pot three-component reaction of isatin, malononitrile or ethyl cyanoacetate and phthalhydrazide catalyzed by piperidine under ultrasound irradiation. For comparison the reactions were carried out under both conventional and ultrasonic conditions. In general, improvement in rates and yields were observed when the reactions were carried out under sonication compared with classical conditions. Full article
(This article belongs to the Special Issue Heterocycles)
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Open AccessCommunication Buddleja officinalis Maximowicz Extract Inhibits Lipid Accumulation on Adipocyte Differentiation in 3T3-L1 Cells and High-Fat Mice
Molecules 2012, 17(7), 8687-8695; doi:10.3390/molecules17078687
Received: 4 July 2012 / Revised: 16 July 2012 / Accepted: 17 July 2012 / Published: 23 July 2012
Cited by 3 | PDF Full-text (617 KB)
Abstract
Obesity is a global health problem. It is also known to be a risk factor for the development of metabolic disorders, type 2 diabetes, systemic hypertension, cardiovascular disease, dyslipidemia, and atherosclerosis. In this study, we elucidated that Buddleja officinalis Maximowicz extract significantly inhibited
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Obesity is a global health problem. It is also known to be a risk factor for the development of metabolic disorders, type 2 diabetes, systemic hypertension, cardiovascular disease, dyslipidemia, and atherosclerosis. In this study, we elucidated that Buddleja officinalis Maximowicz extract significantly inhibited lipid accumulation during 3T3-L1 adipocyte differentiation. Furthermore, Buddleja officinalis Maximowicz extract reduced the body weight gain induced through feeding a high-fat diet to C57BL/6 mice. The treatment of Buddleja officinalis Maximowicz extract significantly reduced the adipose tissue weight to 2.7/100 g of body weight in high-fat mice. When their adipose tissue morphology was investigated for histochemical staining, the distribution of cell size in the high-fat diet groups was hypertrophied compared with those from Buddleja officinalis Maximowicz extract-treated mice. In addition, in Buddleja officinalis Maximowicz extract-treated mice, a significant reduction of serum triglyceride and T-cholesterol was observed at to 21% and 17%, respectively. The discovery of bioactive compounds from diet or dietary supplementation is one of possible ways to control obesity and to prevent or reduce the risks of various obesity-related diseases. These results support that Buddleja officinalis Maximowicz extract is expected to create the therapeutic interest with respect to the treatment of obesity. Full article
(This article belongs to the Section Natural Products)
Open AccessArticle Bioactivity-Guided Isolation of Ethyl-p-methoxycinnamate, an Anti-inflammatory Constituent, from Kaempferia galanga L. Extracts
Molecules 2012, 17(7), 8720-8734; doi:10.3390/molecules17078720
Received: 18 May 2012 / Revised: 24 June 2012 / Accepted: 11 July 2012 / Published: 23 July 2012
Cited by 10 | PDF Full-text (590 KB)
Abstract
This study evaluated the anti-inflammatory effect of Kaempferia galanga (KG) using an activity-guided approach. KG rhizomes were serially extracted with petroleum ether, chloroform, methanol and water. These extracts (2 g/kg each) were tested for their ability to inhibit carrageenan-induced rat paw edema. The
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This study evaluated the anti-inflammatory effect of Kaempferia galanga (KG) using an activity-guided approach. KG rhizomes were serially extracted with petroleum ether, chloroform, methanol and water. These extracts (2 g/kg each) were tested for their ability to inhibit carrageenan-induced rat paw edema. The chloroform extract was found to exert the highest inhibition (42.9%) compared to control (p < 0.001), hence it was further fractionated by washing serially with hexane, hexane-chloroform (1:1) and chloroform. The chloroform fraction (1 g/kg) showed the highest inhibitory effect (51.9%, p < 0.001) on carrageenan-induced edema. This chloroform fraction was further fractionated with hexane-chloroform (1:3) and chloroform, and of the two fractions, the hexane-chloroform sub-fraction was the most effective in inhibiting edema (53.7%, p < 0.001). GC-MS analysis of the active sub-fraction identified ethyl-p-methoxycinnamate (EPMC) as the major component, which was re-crystallized. EPMC dose-dependently inhibited carrageenan-induced edema with an MIC of 100 mg/kg. Moreover, in an in vitro study, EPMC non-selectively inhibited the activities of cyclooxygenases 1 and 2, with IC50 values of 1.12 µM and 0.83 µM respectively. These results validate the anti-inflammatory activity of KG which may be exerted by the inhibition of cyclooxygenases 1 and 2. EPMC isolated from this plant may be the active anti-inflammatory agent. Full article

Review

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Open AccessReview Thiadiazines, N,N-Heterocycles of Biological Relevance
Molecules 2012, 17(7), 7612-7628; doi:10.3390/molecules17077612
Received: 7 May 2012 / Revised: 16 June 2012 / Accepted: 19 June 2012 / Published: 25 June 2012
Cited by 4 | PDF Full-text (412 KB)
Abstract
The 3,5-disubstituted tetrahydro-2H-1,3,5-thiadiazine-2-thione scaffold has found many applications in recent years. This review is aimed at highlighting the most important aspects of these compounds: Synthesis, spectroscopic characterization and biological activities. How the chemical nature of N-substituents influences the overall activity and
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The 3,5-disubstituted tetrahydro-2H-1,3,5-thiadiazine-2-thione scaffold has found many applications in recent years. This review is aimed at highlighting the most important aspects of these compounds: Synthesis, spectroscopic characterization and biological activities. How the chemical nature of N-substituents influences the overall activity and cytotoxicity profile will also be discussed. Full article
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Open AccessReview The Genus Caesalpinia L. (Caesalpiniaceae): Phytochemical and Pharmacological Characteristics
Molecules 2012, 17(7), 7887-7902; doi:10.3390/molecules17077887
Received: 20 April 2012 / Revised: 14 June 2012 / Accepted: 14 June 2012 / Published: 29 June 2012
Cited by 20 | PDF Full-text (274 KB)
Abstract
The genus Caesalpinia (Caesalpiniaceae) has more than 500 species, many of which have not yet been investigated for potential pharmacological activity. Several classes of chemical compounds, such as flavonoids, diterpenes, and steroids, have been isolated from various species of the genus Caesalpinia.
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The genus Caesalpinia (Caesalpiniaceae) has more than 500 species, many of which have not yet been investigated for potential pharmacological activity. Several classes of chemical compounds, such as flavonoids, diterpenes, and steroids, have been isolated from various species of the genus Caesalpinia. It has been reported in the literature that these species exhibit a wide range of pharmacological properties, including antiulcer, anticancer, antidiabetic, anti-inflammatory, antimicrobial, and antirheumatic activities that have proven to be efficacious in ethnomedicinal practices. In this review we present chemical and pharmacological data from recent phytochemical studies on various plants of the genus Caesalpinia. Full article
(This article belongs to the collection Bioactive Compounds)
Open AccessReview Supercritical Synthesis of Biodiesel
Molecules 2012, 17(7), 8696-8719; doi:10.3390/molecules17078696
Received: 18 May 2012 / Revised: 12 July 2012 / Accepted: 16 July 2012 / Published: 23 July 2012
Cited by 17 | PDF Full-text (320 KB)
Abstract
The synthesis of biodiesel fuel from lipids (vegetable oils and animal fats) has gained in importance as a possible source of renewable non-fossil energy in an attempt to reduce our dependence on petroleum-based fuels. The catalytic processes commonly used for the production of
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The synthesis of biodiesel fuel from lipids (vegetable oils and animal fats) has gained in importance as a possible source of renewable non-fossil energy in an attempt to reduce our dependence on petroleum-based fuels. The catalytic processes commonly used for the production of biodiesel fuel present a series of limitations and drawbacks, among them the high energy consumption required for complex purification operations and undesirable side reactions. Supercritical fluid (SCF) technologies offer an interesting alternative to conventional processes for preparing biodiesel. This review highlights the advances, advantages, drawbacks and new tendencies involved in the use of supercritical fluids (SCFs) for biodiesel synthesis. Full article
(This article belongs to the Special Issue Synthesis and Extraction in Supercritical Fluids)

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