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Molecules, Volume 15, Issue 1 (January 2010), Pages 1-605

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Open AccessCorrection Roy et al. On Two Novel Parameters for Validation of Predictive QSAR Models. Molecules, 2009, 14, 1660-1701
Molecules 2010, 15(1), 604-605; https://doi.org/10.3390/molecules15010604
Received: 25 January 2010 / Accepted: 26 January 2010 / Published: 26 January 2010
Cited by 3 | PDF Full-text (23 KB)
Abstract
The authors wish to make the following corrections to this paper [1]: [...] Full article
Open AccessReview Photoresponsive Block Copolymers Containing Azobenzenes and Other Chromophores
Molecules 2010, 15(1), 570-603; https://doi.org/10.3390/molecules15010570
Received: 25 December 2009 / Revised: 11 January 2010 / Accepted: 25 January 2010 / Published: 26 January 2010
Cited by 50 | PDF Full-text (3063 KB)
Abstract
Photoresponsive block copolymers (PRBCs) containing azobenzenes and other chromophores can be easily prepared by controlled polymerization. Their photoresponsive behaviors are generally based on photoisomerization, photocrosslinking, photoalignment and photoinduced cooperative motions. When the photoactive block forms mesogenic phases upon microphase separation of PRBCs, supramolecular
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Photoresponsive block copolymers (PRBCs) containing azobenzenes and other chromophores can be easily prepared by controlled polymerization. Their photoresponsive behaviors are generally based on photoisomerization, photocrosslinking, photoalignment and photoinduced cooperative motions. When the photoactive block forms mesogenic phases upon microphase separation of PRBCs, supramolecular cooperative motion in liquid-crystalline PRBCs enables them to self-organize into hierarchical structures with photoresponsive features. This offers novel opportunities to photocontrol microphase-separated nanostructures of well-defined PRBCs and extends their diverse applications in holograms, nanotemplates, photodeformed devices and microporous films. Full article
(This article belongs to the Special Issue Photochemistry in Organic Synthesis)
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Open AccessArticle Structure, Morphology and Optical Properties of Chiral N-(4-X-phenyl)-N-[1(S)-1-phenylethyl]thiourea, X= Cl, Br, and NO2
Molecules 2010, 15(1), 554-569; https://doi.org/10.3390/molecules15010554
Received: 22 December 2009 / Revised: 14 January 2010 / Accepted: 21 January 2010 / Published: 26 January 2010
Cited by 5 | PDF Full-text (2091 KB)
Abstract
Three new enantiopure aryl-thioureas have been synthesized, N-(4-X-phenyl)-N-[1(S)-1-phenylethyl]thiourea, X= Cl, Br, and NO2 (compounds 1-3, respectively). Large single crystals of up to 0.5 cm3 were grown from methanol/ethanol solutions. Molecular structures were derived from X-ray
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Three new enantiopure aryl-thioureas have been synthesized, N-(4-X-phenyl)-N-[1(S)-1-phenylethyl]thiourea, X= Cl, Br, and NO2 (compounds 1-3, respectively). Large single crystals of up to 0.5 cm3 were grown from methanol/ethanol solutions. Molecular structures were derived from X-ray diffraction studies and the crystal morphology was compared to calculations employing the Bravais-Friedel, Donnay-Harker model. Molecular packing was further studied with Hirshfeld surface calculations. Semi-empirical classical model calculations of refractive indices, optical rotation and the electro-optic effect were performed with OPTACT on the basis of experimentally determined refractive indices. Compound 3 (space group P 1 (No. 1)) was estimated to possess a large electro-optic coefficient r333 of approximately 30 pm/V, whereas 1 and 2 (space Group P 21 (No. 4) exhibit much smaller effects. Full article
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Open AccessArticle Antiproliferative Effect and Ultrastructural Alterations Induced by Psilostachyin on Trypanosoma cruzi
Molecules 2010, 15(1), 545-553; https://doi.org/10.3390/molecules15010545
Received: 19 December 2009 / Revised: 13 January 2010 / Accepted: 18 January 2010 / Published: 25 January 2010
Cited by 17 | PDF Full-text (536 KB)
Abstract
The effect of psilostachyin, a natural sesquiterpene lactone, on the growth and viability of cultured epimastigotes of Trypanosoma cruzi (Tulahuen) is reported. The antiproliferative effect was evaluated by counting the parasites in a Neubauer chamber and measuring their viability by using the dye
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The effect of psilostachyin, a natural sesquiterpene lactone, on the growth and viability of cultured epimastigotes of Trypanosoma cruzi (Tulahuen) is reported. The antiproliferative effect was evaluated by counting the parasites in a Neubauer chamber and measuring their viability by using the dye exclusion technique. The effect on parasite growth was irreversible at concentrations higher than 1.0 µg/mL and the addition of glutathione only partially blocked the effect of the compound. Moreover, we have studied the effects of this natural compound on parasite ultrastructure by transmission electron microscopy. Interestingly, psilostachyin induced ultrastructural alterations on the parasites at a concentration of 0.5 µg/mL, with important mitochondrial swelling and deformity of the kinetoplast. Full article
Open AccessArticle Catalytic Asymmetric 1,4-Additions of β-Keto Esters to Nitroalkenes Promoted by a Bifunctional Homobimetallic Co2-Schiff Base Complex
Molecules 2010, 15(1), 532-544; https://doi.org/10.3390/molecules15010532
Received: 24 December 2009 / Revised: 18 January 2010 / Accepted: 21 January 2010 / Published: 22 January 2010
Cited by 21 | PDF Full-text (212 KB)
Abstract
Catalytic asymmetric 1,4-addition of β-keto esters to nitroalkenes is described. 2.5 mol % of a homobimetallic Lewis acid/Brønsted base bifunctional Co2-Schiff base complex smoothly promoted the reaction in excellent yield (up to 99%), diastereoselectivity, and enantioselectivity (up to >30:1 dr and
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Catalytic asymmetric 1,4-addition of β-keto esters to nitroalkenes is described. 2.5 mol % of a homobimetallic Lewis acid/Brønsted base bifunctional Co2-Schiff base complex smoothly promoted the reaction in excellent yield (up to 99%), diastereoselectivity, and enantioselectivity (up to >30:1 dr and 98% ee). Catalyst loading was successfully reduced to 0.1 mol %. Mechanistic studies suggested that intramolecular cooperative functions of the two Co-metal centers are important for high catalytic activity and stereoselectivity. Full article
(This article belongs to the Special Issue Bifunctional Catalysis)
Open AccessArticle Synthesis of Some New Mono- and Bis-Polycyclic Aromatic Spiro and Bis-Nonspiro-β-Lactams
Molecules 2010, 15(1), 515-531; https://doi.org/10.3390/molecules15010515
Received: 2 November 2009 / Revised: 3 December 2009 / Accepted: 9 December 2009 / Published: 22 January 2010
Cited by 19 | PDF Full-text (461 KB)
Abstract
Some new mono-and bis-polycyclic aromatic spiro-β-lactams and bis-non spiro-polycyclic aromatic β-lactams have been synthesized from imines derived from anthracene-9-carbaldehyde, 2-naphtaldehyde and a ketene derived from 9H-xanthene-9-carboxylic acid and phenoxyacetic acid by a [2+2] cycloaddition reaction. The cycloadducts were characterized by spectral data, including
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Some new mono-and bis-polycyclic aromatic spiro-β-lactams and bis-non spiro-polycyclic aromatic β-lactams have been synthesized from imines derived from anthracene-9-carbaldehyde, 2-naphtaldehyde and a ketene derived from 9H-xanthene-9-carboxylic acid and phenoxyacetic acid by a [2+2] cycloaddition reaction. The cycloadducts were characterized by spectral data, including 1H-NMR, 13C-NMR, IR and elemental analyses. The configurations of some of these mono-spiro-β-lactams were established by X-ray crystal analysis. Full article
Open AccessArticle Synthesis and Antimicrobial Activity of New 5-(2-Thienyl)-1,2,4-triazoles and 5-(2-Thienyl)-1,3,4-oxadiazoles and Related Derivatives
Molecules 2010, 15(1), 502-514; https://doi.org/10.3390/molecules15010502
Received: 14 December 2009 / Revised: 5 January 2010 / Accepted: 11 January 2010 / Published: 22 January 2010
Cited by 35 | PDF Full-text (133 KB)
Abstract
New 5-(2-thienyl)-1,2,4-triazoles and 5-(2-thienyl)-1,3,4-oxadiazoles namely, N-[3-mercapto-5-(2-thienyl)-1,2,4-triazol-4-yl]-N'-arylthioureas 4a–e, 2-arylamino-5-(2-thienyl)-1,2,4-triazolo[3,4-b][1,3,4]thiadiazoles 5a–e, 3-arylaminomethyl-5-(2-thienyl)-1,3,4-oxadiazoline-2-thiones 7a–e, 3-(N-substituted anilinomethyl)-5-(2-thienyl)-1,3,4-oxadiazoline-2-thiones 8a, b and 3-(4-substituted-1-piperazinylmethyl)-5-(2-thienyl)-1,3,4-oxadiazoline-2-thiones 9a–f, were prepared. The synthesized compounds were tested for in vitro activities against certain strains
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New 5-(2-thienyl)-1,2,4-triazoles and 5-(2-thienyl)-1,3,4-oxadiazoles namely, N-[3-mercapto-5-(2-thienyl)-1,2,4-triazol-4-yl]-N'-arylthioureas 4a–e, 2-arylamino-5-(2-thienyl)-1,2,4-triazolo[3,4-b][1,3,4]thiadiazoles 5a–e, 3-arylaminomethyl-5-(2-thienyl)-1,3,4-oxadiazoline-2-thiones 7a–e, 3-(N-substituted anilinomethyl)-5-(2-thienyl)-1,3,4-oxadiazoline-2-thiones 8a, b and 3-(4-substituted-1-piperazinylmethyl)-5-(2-thienyl)-1,3,4-oxadiazoline-2-thiones 9a–f, were prepared. The synthesized compounds were tested for in vitro activities against certain strains of Gram-positive and Gram-negative bacteria and the yeast-like pathogenic fungus Candida albicans. Compound 9a displayed marked broad spectrum antibacterial activity, while compounds 4d, 5e, 7b, 7c, 7d, 9b, 9c and 9d were highly active against the tested Gram-positive bacteria. None of the synthesized compounds were proved to be significantly active against Candida albicans. Full article
Open AccessReview Total Synthesis of Annonaceous Acetogenins Belonging to the Non-Adjacent Bis-THF and Non-Adjacent THF-THP Sub-Classes
Molecules 2010, 15(1), 460-501; https://doi.org/10.3390/molecules15010460
Received: 14 December 2009 / Accepted: 23 December 2009 / Published: 21 January 2010
Cited by 24 | PDF Full-text (2057 KB)
Abstract
The synthesis of the subgroups of acetogenins containing non-adjacent bis-THF and non-adjacent THF-THP core units is reviewed. Specifically, total syntheses of gigantecin, 4-deoxygigantecin, cis-sylvaticin, squamostatin-C, squamostatin-D, sylvaticin and mucocin are discussed. Full article
(This article belongs to the Special Issue Acetogenins: Extraction, Synthesis and Biological Properties)
Open AccessReview Vitamin B6: A Molecule for Human Health?
Molecules 2010, 15(1), 442-459; https://doi.org/10.3390/molecules15010442
Received: 5 November 2009 / Revised: 16 January 2010 / Accepted: 20 January 2010 / Published: 20 January 2010
Cited by 60 | PDF Full-text (634 KB)
Abstract
Vitamin B6 is an intriguing molecule that is involved in a wide range of metabolic, physiological and developmental processes. Based on its water solubility and high reactivity when phosphorylated, it is a suitable co-factor for many biochemical processes. Furthermore the vitamin is
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Vitamin B6 is an intriguing molecule that is involved in a wide range of metabolic, physiological and developmental processes. Based on its water solubility and high reactivity when phosphorylated, it is a suitable co-factor for many biochemical processes. Furthermore the vitamin is a potent antioxidant, rivaling carotenoids or tocopherols in its ability to quench reactive oxygen species. It is therefore not surprising that the vitamin is essential and unquestionably important for the cellular metabolism and well-being of all living organisms. The review briefly summarizes the biosynthetic pathways of vitamin B6 in pro- and eukaryotes and its diverse roles in enzymatic reactions. Finally, because in recent years the vitamin has often been considered beneficial for human health, the review will also sum up and critically reflect on current knowledge how human health can profit from vitamin B6. Full article
(This article belongs to the Special Issue Vitamins)
Open AccessArticle In Vitro and in Vivo Effects of Three Different Mitragyna speciosa Korth Leaf Extracts on Phase II Drug Metabolizing Enzymes—Glutathione Transferases (GSTs)
Molecules 2010, 15(1), 432-441; https://doi.org/10.3390/molecules15010432
Received: 30 November 2009 / Revised: 2 January 2010 / Accepted: 7 January 2010 / Published: 20 January 2010
Cited by 26 | PDF Full-text (125 KB)
Abstract
In the present study, we investigate the effects of three different Mitragyna speciosa extracts, namely methanolic, aqueous and total alkaloid extracts, on glutathione transferase-specific activity in male Sprague Dawley rat liver cytosol in vitro and in vivo. In the in vitro study,
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In the present study, we investigate the effects of three different Mitragyna speciosa extracts, namely methanolic, aqueous and total alkaloid extracts, on glutathione transferase-specific activity in male Sprague Dawley rat liver cytosol in vitro and in vivo. In the in vitro study, the effect of Mitragyna speciosa extracts (0.01 to 750 µg/mL) against the specific activity of glutathione transferases was examined in rat liver cytosolic fraction from untreated rats. Our data show concentration dependent inhibition of cytosolic GSTs when Mitragyna speciosa extract was added into the reaction mixture. At the highest concentration used, the methanolic extract showed the highest GSTs specific activity inhibition (61%), followed by aqueous (50%) and total alkaloid extract (43%), respectively. In in vivo study, three different dosages; 50, 100 and 200 mg/kg for methanolic and aqueous extracts and 5, 10 and 20 mg/kg for total alkaloid extract were given orally for 14 days. An increase in GST specific activity was generally observed. However, only Mitragyna speciosa aqueous extract with a dosage of 100 mg/kg showed significant results: 129% compared to control. Full article
Open AccessArticle Condensed Tannins from Mangrove Species Kandelia candel and Rhizophora mangle and Their Antioxidant Activity
Molecules 2010, 15(1), 420-431; https://doi.org/10.3390/molecules15010420
Received: 12 December 2009 / Revised: 12 January 2010 / Accepted: 17 January 2010 / Published: 20 January 2010
Cited by 56 | PDF Full-text (305 KB)
Abstract
The structures of condensed tannins isolated from two mangrove species, Kandelia candel and Rhizophora mangle, were characterized by 13C nuclear magnetic resonance (NMR) spectroscopy and matrix assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOF MS) analyses. Results demonstrate that large heterogeneity occurs in
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The structures of condensed tannins isolated from two mangrove species, Kandelia candel and Rhizophora mangle, were characterized by 13C nuclear magnetic resonance (NMR) spectroscopy and matrix assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOF MS) analyses. Results demonstrate that large heterogeneity occurs in degree of polymerization, pattern of hydroxylation, and substitution with monosaccharides in the structures of the condensed tannins. Condensed tannin oligomers from K. candel and R. mangle were shown to be heterogeneous mixtures consisting of procyanidin and prodelphinidin structural units with the former dominating. The MALDI-TOF mass spectra contained masses corresponding to a distinct oligomeric series of glycosylated heteropolyflavan units. In addition, condensed tannins from two mangrove plants were screened for their potential antioxidant activities using 1,1-diphenyl-2-picrylhydrazyl (DPPH) and ferric reducing antioxidant power (FRAP) model systems. Full article
Open AccessArticle Gas-Phase Pyrolytic Reaction of 4-Aryl-3-buten-2-ols and Allyl Benzyl Ethers: Kinetic and Mechanistic Study
Molecules 2010, 15(1), 407-419; https://doi.org/10.3390/molecules15010407
Received: 22 November 2009 / Revised: 28 December 2009 / Accepted: 8 January 2010 / Published: 20 January 2010
Cited by 2 | PDF Full-text (174 KB)
Abstract
Flash vacuum pyrolysis (FVP) of 4-aryl-3-buten-2-ols [ArCH=CH-CH(CH3)OH, where Ar is phenyl, p-MeO, p-Me, p-Cl, p-NO2] gave the corresponding buta-1,3-dien-1-ylbenzene (ArCH=CH-CH=CH2, where Ar is Ph, p-MeO, p-Me, p-Cl, p-NO2
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Flash vacuum pyrolysis (FVP) of 4-aryl-3-buten-2-ols [ArCH=CH-CH(CH3)OH, where Ar is phenyl, p-MeO, p-Me, p-Cl, p-NO2] gave the corresponding buta-1,3-dien-1-ylbenzene (ArCH=CH-CH=CH2, where Ar is Ph, p-MeO, p-Me, p-Cl, p-NO2) and 7-X-1,2-dihydronaphthalene derivatives (where X is H, MeO); FVP of 1-aryl-3-benzyloxy1-1-butenes and benzyl cinnamyl ethers [ArCH=CHCH(X)OCH2Ph, where Ar is phenyl, p-MeO, p-Me, p-Cl, X is H, Me, Ph] gave the corresponding but-2-en-1-ylbenzene derivatives (ArCH2CH=CH-X, where X is H, Me, Ph) together with benzaldehyde. The proposed mechanism of these pyrolytic transformations was supported by kinetic and product analysis. Full article
Open AccessArticle Isolation, Synthesis and Structures of Ginsenoside Derivatives and Their Anti-Tumor Bioactivity
Molecules 2010, 15(1), 399-406; https://doi.org/10.3390/molecules15010399
Received: 4 December 2009 / Revised: 8 January 2010 / Accepted: 11 January 2010 / Published: 19 January 2010
Cited by 13 | PDF Full-text (422 KB)
Abstract
Protopanaxatriol saponins obtained with AB-8 macroporous resin mainly consisted of ginsenosides Rg1 and Re. A novel mono-ester of ginsenoside-Rh1 (ginsenoside-ORh1) was synthesized through further enzymatic hydrolysis and octanoyl chloride modifications. A 53% yield was obtained by a facile synthetic
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Protopanaxatriol saponins obtained with AB-8 macroporous resin mainly consisted of ginsenosides Rg1 and Re. A novel mono-ester of ginsenoside-Rh1 (ginsenoside-ORh1) was synthesized through further enzymatic hydrolysis and octanoyl chloride modifications. A 53% yield was obtained by a facile synthetic method. The structures were identified on the basis of 1D-NMR and 2D-NMR, as well as ESI-TOF-MS mass spectroscopic analyses. The isolated and synthetic compounds were applied in an anti-tumor bioassay, in which ginsenoside ORh1 showed moderate effects on Murine H22 Hepatoma Cells. Full article
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Open AccessArticle Luteolin Isolated from the Flowers of Lonicera japonica Suppresses Inflammatory Mediator Release by Blocking NF-κB and MAPKs Activation Pathways in HMC-1 Cells
Molecules 2010, 15(1), 385-398; https://doi.org/10.3390/molecules15010385
Received: 30 November 2009 / Revised: 7 January 2010 / Accepted: 12 January 2010 / Published: 18 January 2010
Cited by 55 | PDF Full-text (1214 KB)
Abstract
Luteolin (3′,4′,5,7-tetrahydroxylflavone) is a plant flavonoid and pharmacologically active agent that has been isolated from several plant species. In the present study, the effect of luteolin from the flowers of Lonicera japonica on phorbol 12-myristate 13-acetate (PMA) plus A23187-induced mast cell activation was
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Luteolin (3′,4′,5,7-tetrahydroxylflavone) is a plant flavonoid and pharmacologically active agent that has been isolated from several plant species. In the present study, the effect of luteolin from the flowers of Lonicera japonica on phorbol 12-myristate 13-acetate (PMA) plus A23187-induced mast cell activation was examined. Luteolin significantly inhibited the induction of inflammatory cytokines such as tumor necrosis factor (TNF)-α, interleukin (IL)-8, IL-6 and granulocyte-macrophage colony-stimulating factor (GM-CSF) by PMA plus A23187. Moreover, luteolin attenuated cyclooxygenase (COX)-2 expression and intracellular Ca2+ levels. In activated HMC-1 cells, the phosphorylation of extra-signal response kinase (ERK 1/2) and c-jun N-terminal Kinase (JNK 1/2), but not p38 mitogen-activated protein kinase (p38 MAPK) were decreased by treatment of the cells with luteolin. Luteolin inhibited PMA plus A23187-induced nuclear factor (NF)-κB activation, IκB degradation, and luciferase activity. Furthermore, luteolin suppressed the expression of TNF-α, IL-8, IL-6, GM-CSF, and COX-2 through a decrease in the intracellular Ca2+ levels, and also showed a suppression of the ERK 1/2, JNK 1/2, and NF-κB activation. These results indicated that luteolin from the flowers of Lonicera japonica exerted a regulatory effect on mast cell-mediated inflammatory diseases, such as RA, allergy disease and IBD. Full article
Open AccessArticle A Simple Preparation of 2,3,4,6-Tetra-O-acyl-Gluco-, Galacto- and Mannopyranoses and Relevant Theoretical Study
Molecules 2010, 15(1), 374-384; https://doi.org/10.3390/molecules15010374
Received: 12 November 2009 / Revised: 16 December 2009 / Accepted: 22 December 2009 / Published: 18 January 2010
Cited by 5 | PDF Full-text (138 KB) | Supplementary Files
Abstract
The deacylation of glucose, galactose and mannose pentaacetates, galactose and mannose penta(3-bromo)benzoates, as well as the dealkylation of 2,3,4,6-tetra-O-acetyl and 2,3,4,6-tetra-O-(3-bromo)benzoyl methyl α-D-glucopyranosides have been studied. In addition, a computational study on the deacylation of β-D
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The deacylation of glucose, galactose and mannose pentaacetates, galactose and mannose penta(3-bromo)benzoates, as well as the dealkylation of 2,3,4,6-tetra-O-acetyl and 2,3,4,6-tetra-O-(3-bromo)benzoyl methyl α-D-glucopyranosides have been studied. In addition, a computational study on the deacylation of β-D-glucose pentaacetate has been carried out with density functional theory (B3LYP/6-31G*). The anomeric effect during deacetylation and dealkylation has been clearly demonstrated in both experimental and computational results. Full article
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