Next Issue
Previous Issue

E-Mail Alert

Add your e-mail address to receive forthcoming issues of this journal:

Journal Browser

Journal Browser

Table of Contents

Molecules, Volume 15, Issue 11 (November 2010), Pages 7509-8533

  • Issues are regarded as officially published after their release is announced to the table of contents alert mailing list.
  • You may sign up for e-mail alerts to receive table of contents of newly released issues.
  • PDF is the official format for papers published in both, html and pdf forms. To view the papers in pdf format, click on the "PDF Full-text" link, and use the free Adobe Readerexternal link to open them.
View options order results:
result details:
Displaying articles 1-71
Export citation of selected articles as:
Open AccessArticle Characterization of Phosphate Solubilizing Bacteria in Sediments from a Shallow Eutrophic Lake and a Wetland: Isolation, Molecular Identification and Phosphorus Release Ability Determination
Molecules 2010, 15(11), 8518-8533; https://doi.org/10.3390/molecules15118518
Received: 12 September 2010 / Revised: 16 November 2010 / Accepted: 17 November 2010 / Published: 22 November 2010
Cited by 20 | PDF Full-text (720 KB)
Abstract
The transformation of phosphorus (P) is a major factor of lake eutrophication, and phosphate releasing bacteria play an important role in the release process. Experiments were conducted to investigate P content and characterize phosphate solubilizing bacterial composition at the molecular level in a
[...] Read more.
The transformation of phosphorus (P) is a major factor of lake eutrophication, and phosphate releasing bacteria play an important role in the release process. Experiments were conducted to investigate P content and characterize phosphate solubilizing bacterial composition at the molecular level in a shallow eutrophic lake and a wetland. Results showed that P concentrations were relatively high and derived from agricultural runoff and domestic or industrial pollution. Enumeration and molecular identification of these strains indicated that these bacterial groups were abundant in the ecosystem and various kinds of bacteria participated in the phosphorus release process. Twelve phosphate solubilizing bacteria, including eight organic P-solubilizing bacteria (OPBs) and four inorganic P-solubilizing bacteria (IPBs), which belonged to three different families, were isolated and identified. Cupriavidus basilensis was found for the first time to have the ability to mineralize organic P (OP). Laboratory tests on P release ability revealed that IPBs were more effective at releasing P than OPBs. The most efficient IPB strain could accumulate over 170 mg·L-1 orthophosphate, while the equivalent OPB strain only liberated less than 4 mg·L-1 orthophosphate in liquid culture. The results obtained from this investigation should help clarify the roles of microorganisms in aquatic systems and the mechanisms of eutrophication. Full article
Open AccessArticle Antioxidant, Anti-Inflammatory and Anti-Influenza Properties of Components from Chaenomeles speciosa
Molecules 2010, 15(11), 8507-8517; https://doi.org/10.3390/molecules15118507
Received: 1 November 2010 / Revised: 15 November 2010 / Accepted: 17 November 2010 / Published: 22 November 2010
Cited by 40 | PDF Full-text (286 KB)
Abstract
The fruit of Chaenomeles speciosa is a traditional Chinese medicine used for the treatment of dyspepsia and various inflammatory diseases. In the present study, we evaluated the potential radical scavenging capacity, and activity against nitrous oxide, inflammatory cytokines production and neuramindase (NA) of
[...] Read more.
The fruit of Chaenomeles speciosa is a traditional Chinese medicine used for the treatment of dyspepsia and various inflammatory diseases. In the present study, we evaluated the potential radical scavenging capacity, and activity against nitrous oxide, inflammatory cytokines production and neuramindase (NA) of its isolates. The results showed that 3,4-dihydroxybenzoic acid (1) displayed higher inhibitory activities on DPPH and NA with IC50 values of 1.02 mg/mL and 1.27 mg/mL respectively, and quercetin (2) also showed significant inhibitory action on DPPH and NA, with IC50 values of 3.82 mg/mL and 1.90 mg/mL. Compounds 1, 2 and methyl 3-hydroxybutanedioic ester (3) could inhibit the production of TNF-a by 22.73%, 33.14% and 37.19% at 5 mg/mL (P < 0.05) compared with the control. In addition, compound 2 was found to be active on the release of IL-6 in RAW264.7 macrophage cells, with an inhibitory rate of 39.79% (P < 0.05). The anti-inflammatory effect of compound 3 is disclosed for the first time in this study. Avian influenza is usually accompanied by virus invasion followed by the occurrence of oxidative stress and serious inflammation, so the multiple effects of the isolates may play a cocktail-like role in the treatment of avian influenza, and C. speciosa components, especially quercetin, might be a potent source for anti-viral and anti-inflammatory agents. Full article
(This article belongs to the Special Issue Antioxidants)
Open AccessCommunication Synthesis of Seco-Chlorinated Derivatives of Phenanthroindolizidine Precursors via Friedel-Crafts Reaction
Molecules 2010, 15(11), 8501-8506; https://doi.org/10.3390/molecules15118501
Received: 9 October 2010 / Revised: 14 November 2010 / Accepted: 14 November 2010 / Published: 22 November 2010
Cited by 1 | PDF Full-text (178 KB)
Abstract
In the course of synthesizing 3-demethyltylophorine (1) by Lewis acid catalyzed intramolecular Friedel-Crafts reaction starting from N-(3-hydroxy-2,6,7-trimethoxy-phenanthr-9-ylmethyl)-2-chloromethylpyrrolidine, two chlorinated phenanthrene derivatives N-(4,10-dichloro-3-hydroxy-2,6,7-trimethoxyphenanthr-9-ylmethyl)-2-chloromethylpyrrolidine (4) and N-(4-chloro-3-hydroxy-2,6,7-trimethoxyphenanthr-9-ylmethyl)-2-chloromethylpyrrolidine (5) were obtained. The structures of these compounds were determined by spectroscopic analysis. Full article
Open AccessArticle Selective Inhibitory Effect of Epigallocatechin-3-gallate on Migration of Vascular Smooth Muscle Cells
Molecules 2010, 15(11), 8488-8500; https://doi.org/10.3390/molecules15118488
Received: 31 August 2010 / Revised: 13 November 2010 / Accepted: 17 November 2010 / Published: 19 November 2010
Cited by 9 | PDF Full-text (3374 KB)
Abstract
In order to prevent restenosis after angioplasty or stenting, one of the most popular targets is suppression of the abnormal growth and excess migration of vascular smooth muscle cells (VSMCs) with drugs. However, the drugs also adversely affect vascular endothelial cells (VECs), leading
[...] Read more.
In order to prevent restenosis after angioplasty or stenting, one of the most popular targets is suppression of the abnormal growth and excess migration of vascular smooth muscle cells (VSMCs) with drugs. However, the drugs also adversely affect vascular endothelial cells (VECs), leading to the induction of late thrombosis. We have investigated the effect of epigallocatechin-3-gallate (EGCG) on the proliferation and migration of VECs and VSMCs. Both cells showed dose-dependent decrease of viability in response to EGCG while they have different IC50 values of EGCG (VECs, 150 mM and VSMCs, 1050 mM). Incubating both cells with EGCG resulted in significant reduction in cell proliferation irrespective of cell type. The proliferation of VECs were greater affected than that of VSMCs at the same concentrations of EGCG. EGCG exerted differential migration-inhibitory activity in VECs vs. VSMCs. The migration of VECs was not attenuated by 200 mM EGCG, but that of VSMCs was significantly inhibited at the same concentration of EGCG. It is suggested that that EGCG can be effectively used as an efficient drug for vascular diseases or stents due to its selective activity, completely suppressing the proliferation and migration of VSMCs, but not adversely affecting VECs migration in blood vessels. Full article
(This article belongs to the Special Issue Antioxidants)
Figures

Graphical abstract

Open AccessArticle The Pharmacokinetics of Raloxifene and Its Interaction with Apigenin in Rat
Molecules 2010, 15(11), 8478-8487; https://doi.org/10.3390/molecules15118478
Received: 25 October 2010 / Revised: 15 November 2010 / Accepted: 16 November 2010 / Published: 18 November 2010
Cited by 10 | PDF Full-text (299 KB)
Abstract
Purpose: Raloxifene is a selective estrogen receptor modulator which is structurally similar to tamoxifen. As flavonoids can interact with raloxifene in vitro, we evaluated the in vivo pharmacokinetics of raloxifene in rats when co-administered with apigenin. Methods: The pharmacokinetics of
[...] Read more.
Purpose: Raloxifene is a selective estrogen receptor modulator which is structurally similar to tamoxifen. As flavonoids can interact with raloxifene in vitro, we evaluated the in vivo pharmacokinetics of raloxifene in rats when co-administered with apigenin. Methods: The pharmacokinetics of raloxifene in the absence or presence of apigenin was investigated in rats after different dosage regimens. The plasma concentrations before and after enzymatic hydrolysis were analyzed by HPLC, and the pharmacokinetic profiles of raloxifene administered alone and in combination with apigenin were compared. Results: Co-administration of apigenin with raloxifene in a 1:2 ratio by weight resulted in a 55% and 37% increase in the Cmax and AUC of intact raloxifene, respectively. When equal proportions of raloxifene and apigenin (1:1) were administered, the Cmax and AUC of intact raloxifene were increased by 173% and 97% respectively. This increase in intact raloxifene was not associated with an increase in total raloxifene (intact plus conjugated raloxifene) because AUC and Cmax of total raloxifene when administered alone or in combination with apigenin were found to be similar. The results indicated that apigenin inhibited the glucuronidation and sulfation of raloxifene in the intestine bringing about an increased bioavailability of the drug. Conclusions: The results showed that apigenin decreased the first-pass metabolism of raloxifene but did not increase its absorption from the gastrointestinal tract. Full article
Open AccessArticle Antiseptic Activity and Phenolic Constituents of the Aerial Parts of Vitex negundo var. cannabifolia
Molecules 2010, 15(11), 8469-8477; https://doi.org/10.3390/molecules15118469
Received: 15 October 2010 / Revised: 11 November 2010 / Accepted: 15 November 2010 / Published: 18 November 2010
Cited by 33 | PDF Full-text (277 KB)
Abstract
Four phenolics, salviaplebeiaside (1), γ-tocopherol (2), chrysosplenol-D (4), and isovitexin (5), along with α-tocoquinone (3) and β-sitosterol (6) were isolated from the aerial parts of Vitex negundo var.
[...] Read more.
Four phenolics, salviaplebeiaside (1), γ-tocopherol (2), chrysosplenol-D (4), and isovitexin (5), along with α-tocoquinone (3) and β-sitosterol (6) were isolated from the aerial parts of Vitex negundo var. cannabifolia. The isolation was performed using bio-assay tracking experiments. The structures of compounds 1-5 were established by spectroscopic means. The antibacterial activities of the compounds were assessed against Escherichia coli, Bacillus subtilis, Micrococcus tetragenus and Pseudomonas fluorescens. Chrysosplenol-D (4) exhibited activities against all the four spoilage microorganisms. Full article
(This article belongs to the Special Issue Phenolics and Polyphenolics)
Open AccessReview Sorption Speciation of Lanthanides/Actinides on Minerals by TRLFS, EXAFS and DFT Studies: A Review
Molecules 2010, 15(11), 8431-8468; https://doi.org/10.3390/molecules15118431
Received: 8 October 2010 / Revised: 9 November 2010 / Accepted: 15 November 2010 / Published: 17 November 2010
Cited by 95 | PDF Full-text (1496 KB)
Abstract
Lanthanides/actinides sorption speciation on minerals and oxides by means of time resolved laser fluorescence spectroscopy (TRLFS), extended X-ray absorption fine structure spectroscopy (EXAFS) and density functional theory (DFT) is reviewed in the field of nuclear disposal safety research. The theoretical aspects of the
[...] Read more.
Lanthanides/actinides sorption speciation on minerals and oxides by means of time resolved laser fluorescence spectroscopy (TRLFS), extended X-ray absorption fine structure spectroscopy (EXAFS) and density functional theory (DFT) is reviewed in the field of nuclear disposal safety research. The theoretical aspects of the methods are concisely presented. Examples of recent research results of lanthanide/actinide speciation and local atomic structures using TRLFS, EXAFS and DFT are discussed. The interaction of lanthanides/actinides with oxides and minerals as well as their uptake are also of common interest in radionuclide chemistry. Especially the sorption and inclusion of radionuclides into several minerals lead to an improvement in knowledge of minor components in solids. In the solid-liquid interface, the speciation and local atomic structures of Eu(III), Cm(III), U(VI), and Np(IV/VI) in several natural and synthetic minerals and oxides are also reviewed and discussed. The review is important to understand the physicochemical behavior of lanthanides/actinides at a molecular level in the natural environment. Full article
(This article belongs to the Special Issue Radiochemistry)
Open AccessArticle Microwave-Assisted Synthesis of Novel 2,3-Dihydro-4-Pyridinones
Molecules 2010, 15(11), 8425-8430; https://doi.org/10.3390/molecules15118425
Received: 22 October 2010 / Revised: 9 November 2010 / Accepted: 11 November 2010 / Published: 17 November 2010
Cited by 3 | PDF Full-text (111 KB)
Abstract
Novel 2,3-dihydro-4-pyridinones were synthesized via the reaction of curcumin and primary amines or amine acetates under microwave irradiation. Montmorillonite K-10 was used as a catalyst. Reaction times did not exceed 120 s. The structures of the compounds were established by elemental analysis and
[...] Read more.
Novel 2,3-dihydro-4-pyridinones were synthesized via the reaction of curcumin and primary amines or amine acetates under microwave irradiation. Montmorillonite K-10 was used as a catalyst. Reaction times did not exceed 120 s. The structures of the compounds were established by elemental analysis and from their mass, 1H- and 13C-NMR spectra. Full article
(This article belongs to the Section Organic Chemistry)
Open AccessReview Combining the Benefits of Homogeneous and Heterogeneous Catalysis with Tunable Solvents and Nearcritical Water
Molecules 2010, 15(11), 8400-8424; https://doi.org/10.3390/molecules15118400
Received: 11 October 2010 / Accepted: 8 November 2010 / Published: 16 November 2010
Cited by 29 | PDF Full-text (456 KB)
Abstract
The greatest advantage of heterogeneous catalysis is the ease of separation, while the disadvantages are often limited activity and selectivity. We report solvents that use tunable phase behavior to achieve homogeneous catalysis with ease of separation. Tunable solvents are homogeneous mixtures of water
[...] Read more.
The greatest advantage of heterogeneous catalysis is the ease of separation, while the disadvantages are often limited activity and selectivity. We report solvents that use tunable phase behavior to achieve homogeneous catalysis with ease of separation. Tunable solvents are homogeneous mixtures of water or polyethylene glycol with organics such as acetonitrile, dioxane, and THF that can be used for homogeneously catalyzed reactions. Modest pressures of a soluble gas, generally CO2, achieve facile post-reaction heterogeneous separation of products from the catalyst. Examples shown here are rhodium-catalyzed hydroformylation of 1-octene and p-methylstyrene and palladium catalyzed C-O coupling to produce o-tolyl-3,5-xylyl ether and 3,5-di-tert-butylphenol. Both were successfully carried out in homogeneous tunable solvents followed by separation efficiencies of up to 99% with CO2 pressures of 3 MPa. Further examples in tunable solvents are enzyme catalyzed reactions such as kinetic resolution of rac-1-phenylethyl acetate and hydrolysis of 2-phenylethyl acetate (2PEA) to 2-phenylethanol (2PE). Another tunable solvent is nearcritical water (NCW), whose unique properties offer advantages for developing sustainable alternatives to traditional processes. Some examples discussed are Friedel-Crafts alkylation and acylation, hydrolysis of benzoate esters, and water-catalyzed deprotection of N-Boc-protected amine compounds. Full article
(This article belongs to the Special Issue Heterogeneous Catalysis)
Open AccessArticle Comparative Analysis of Headspace Volatiles of Chinese Rosa rugosa
Molecules 2010, 15(11), 8390-8399; https://doi.org/10.3390/molecules15118390
Received: 21 October 2010 / Revised: 9 November 2010 / Accepted: 11 November 2010 / Published: 16 November 2010
Cited by 17 | PDF Full-text (173 KB)
Abstract
The floral headspace compounds of Chinese Rosa rugosa germplasms that were isolated by an automated headspace sampler with built-in trap, and followed by gas chromatography-mass spectrometry for identification and quantification. Up to 33 volatile compounds were identified from the 23 rose germplasms, including
[...] Read more.
The floral headspace compounds of Chinese Rosa rugosa germplasms that were isolated by an automated headspace sampler with built-in trap, and followed by gas chromatography-mass spectrometry for identification and quantification. Up to 33 volatile compounds were identified from the 23 rose germplasms, including nine alcohols, five esters, three alkanes, 10 terpenes, three aldehydes, two ketones, and one ether. The main floral components identified were 2-phenylethanol, β-citronellol, ethanol, and n-hexane. ‘xizi’, ‘miaofengshan’, ‘xiangciguo’, and ‘tangbai’ contained the highest amounts of 2-phenylethanol at 84.66 μg·g-1, β-citronellol at 70.98 μg·g-1, ethanol at 83.87 μg·g-1, and n-hexane at 18.23 μg·g-1, respectively. ‘Rongchengyesheng’, ‘tanghong’, ‘xizi’, ‘miaofengshan’, and ‘baizizhi’ could be considered good materials for extracting rose oil and breeding new cultivars. Full article
Open AccessArticle Anti-Neoplastic Effects of Gallic Acid, a Major Component of Toona sinensis Leaf Extract, on Oral Squamous Carcinoma Cells
Molecules 2010, 15(11), 8377-8389; https://doi.org/10.3390/molecules15118377
Received: 2 November 2010 / Revised: 15 November 2010 / Accepted: 16 November 2010 / Published: 16 November 2010
Cited by 64 | PDF Full-text (468 KB)
Abstract
Extract of Toona sinensis (TS) has been reported to have various effects on cultured cell lines, including anti-proliferative activity in cancer cells. We have studied the effects of TS on various human oral squamous carcinoma cell lines (HOSCC), including UM1, UM2,
[...] Read more.
Extract of Toona sinensis (TS) has been reported to have various effects on cultured cell lines, including anti-proliferative activity in cancer cells. We have studied the effects of TS on various human oral squamous carcinoma cell lines (HOSCC), including UM1, UM2, SCC-4, and SCC-9. These cell lines were treated with TS leaf extract and screened for viability, apoptosis, necrosis, and apoptotic gene expression. Normal human oral keratinocytes (NHOK) served as a control for cytotoxic assays. Viability of TS-treated HOSCC was reduced, whereas that of NHOK was not affected. FACScan analysis revealed that the leaf extract induced apoptosis or a combination of apoptosis and necrosis, depending on cell type. Microarray and semi-quantitative RT-PCR analysis for apoptotic-related gene expression revealed that 3,4,5-trihydroxybenzoic acid (gallic acid, one of the major bioactive compounds purified from TS extract) up-regulated pro-apoptotic genes such TNF-α, TP53BP2, and GADD45A, and down-regulated the anti-apoptotic genes Survivin and cIAP1, resulting in cell death. This study suggests that gallic acid, the major bioactive compound present, is responsible for the anti-neoplastic effect of Toona sinensis leaf extract. Full article
(This article belongs to the Section Natural Products Chemistry)
Figures

Graphical abstract

Open AccessArticle Median Lethal Dose, Antimalarial Activity, Phytochemical Screening and Radical Scavenging of Methanolic Languas galanga Rhizome Extract
Molecules 2010, 15(11), 8366-8376; https://doi.org/10.3390/molecules15118366
Received: 29 September 2010 / Revised: 7 November 2010 / Accepted: 11 November 2010 / Published: 16 November 2010
Cited by 15 | PDF Full-text (152 KB) | Supplementary Files
Abstract
The methanolic extract of Languas galanga rhizomes was investigated for antimalarial activity against Plasmodium berghei (NK65) infections in mice. The median lethal dose was determined to ascertain the safety of the extract in ICR mice of both sexes. The antimalarial activities during early
[...] Read more.
The methanolic extract of Languas galanga rhizomes was investigated for antimalarial activity against Plasmodium berghei (NK65) infections in mice. The median lethal dose was determined to ascertain the safety of the extract in ICR mice of both sexes. The antimalarial activities during early and established infections, as well as the prophylactic activity were evaluated. Phytochemical screening and radical scavenging activity of the extract were also investigated to elucidate the possible mechanism of the antimalarial properties. The acute oral toxicity (LD50) of Languas galanga extract in mice was established to be 4,998 mg/kg. The extract of Languas galanga rhizomes demonstrated significant antiplasmodial activity in all the three models of the antimalarial evaluations. Phytochemical screening revealed the presence of some vital antiplasmodial constituents such as terpenoids and flavonoids. The extract also exhibited a moderate capacity to scavenge the free radicals. The rhizome extract of Languas galanga thus possesses antimalarial activity, which explains the rational usage of this plant in traditional Malaysian medicine. Full article
Open AccessArticle A Novel 18-Norclerodane Diterpenoid from the Roots of Tinospora sagittata var. yunnanensis
Molecules 2010, 15(11), 8360-8365; https://doi.org/10.3390/molecules15118360
Received: 10 September 2010 / Revised: 4 November 2010 / Accepted: 10 November 2010 / Published: 16 November 2010
Cited by 9 | PDF Full-text (195 KB)
Abstract
A novel 18-nor-clerodane diterpenoid named sagitone (1) was isolated from the 95% ethanol extract of dry roots of Tinospora sagittata var. yunnanensis together with the five known diterpenoids columbin (2), palmatoside C (3), fibleucin (4),
[...] Read more.
A novel 18-nor-clerodane diterpenoid named sagitone (1) was isolated from the 95% ethanol extract of dry roots of Tinospora sagittata var. yunnanensis together with the five known diterpenoids columbin (2), palmatoside C (3), fibleucin (4), tinophylloloside (5) and epitinophylloloside (6). The structure of the new compound 1 was determined based on MS, IR, 1D and 2D NMR spectral data. The compounds 1~6 did not show significant cytotoxic activity against cancer cell lines K562 and HL-60. Full article
(This article belongs to the Section Natural Products Chemistry)
Open AccessArticle Pancreatic Lipase Inhibition by C-Glycosidic Flavones Isolated from Eremochloa ophiuroides
Molecules 2010, 15(11), 8251-8259; https://doi.org/10.3390/molecules15118251
Received: 2 November 2010 / Revised: 11 November 2010 / Accepted: 12 November 2010 / Published: 16 November 2010
Cited by 42 | PDF Full-text (205 KB)
Abstract
Activity-guided fractionation of a methanolic extract of the leaves of Eremochloa ophiuroides (centipede grass) using a pancreatic lipase inhibitory assay led to the isolation and identification of a new C-glycosidic flavone, luteolin 6-C-b-D-boivinopyranoside (1), as well as eight
[...] Read more.
Activity-guided fractionation of a methanolic extract of the leaves of Eremochloa ophiuroides (centipede grass) using a pancreatic lipase inhibitory assay led to the isolation and identification of a new C-glycosidic flavone, luteolin 6-C-b-D-boivinopyranoside (1), as well as eight known compounds. The structures of these compounds were established on the basis of interpretation of their spectroscopic data. Among these isolates, the C-glycosidic flavones 15 showed potent inhibitory effects on pancreatic lipase, with IC50 values ranging from 18.5 ± 2.6 to 50.5 ± 3.9 mM. Full article
(This article belongs to the collection Bioactive Compounds)
Open AccessArticle Synthesis, Structures and Properties of Cu(II) and Mn(II) Complexes with 1,10-Phenanthroline-2-carboxylic acid and 2,2’-Bipyridine Ligands
Molecules 2010, 15(11), 8349-8359; https://doi.org/10.3390/molecules15118349
Received: 10 September 2010 / Revised: 18 October 2010 / Accepted: 25 October 2010 / Published: 15 November 2010
Cited by 9 | PDF Full-text (456 KB) | Supplementary Files
Abstract
Four new 2,2’-bipyridine and 1,10-phenanthroline complexes, namely [Mn(phenca)2]·(H2O)2 (1), [Cu4(phen)4(OH-)4(H2O)2](DMF)4(ClO4-)4(H2O) (2), [Cu2
[...] Read more.
Four new 2,2’-bipyridine and 1,10-phenanthroline complexes, namely [Mn(phenca)2]·(H2O)2 (1), [Cu4(phen)4(OH-)4(H2O)2](DMF)4(ClO4-)4(H2O) (2), [Cu2(2,2-bipy)2(C2O42-)(H2O)2(NO3)2] (3) and [Cu(2,2-bipy)2(ClO4-)](ClO4-) (4) (2,2’-bpy = 2,2’-bipyridine, Hphenca = 1,10-phenanthroline-2-carboxylic acid) have been synthesized by a hydrothermal reaction. The products were characterized by elemental analysis, infrared spectroscopy and X-ray crystal diffraction. While strong hydrogen bonds play central roles in the formation of the 3D structure, the combined influence of the weak interactions such as π···π interactions is also evident in the structures. A preliminary investigation on the ion exchange properties of the complexes is presented. Full article
Open AccessArticle Synthesis and Properties of Chiral Thioureas Bearing an Additional Function at a Remote Position Tethered by a 1,5-Disubstituted Triazole
Molecules 2010, 15(11), 8327-8348; https://doi.org/10.3390/molecules15118327
Received: 20 October 2010 / Revised: 8 November 2010 / Accepted: 10 November 2010 / Published: 15 November 2010
Cited by 4 | PDF Full-text (250 KB)
Abstract
The synthesis and properties of multifunctional thioureas bearing a variety of functional groups at a position remote from the thiourea moiety are described. A 1,5-disubstituted triazole tether connected with a thiourea and another functional group was synthesized via ruthenium catalyzed Huisgen cycloaddition. We
[...] Read more.
The synthesis and properties of multifunctional thioureas bearing a variety of functional groups at a position remote from the thiourea moiety are described. A 1,5-disubstituted triazole tether connected with a thiourea and another functional group was synthesized via ruthenium catalyzed Huisgen cycloaddition. We demonstrate the utility of the synthetic thioureas as asymmetric catalysts and probes for the mechanistic elucidation of the course of the Michael reaction of an α,β-unsaturated imide Full article
(This article belongs to the Special Issue Bifunctional Catalysis)
Open AccessArticle Catalytic Asymmetric Synthesis of Both Enantiomers of 4‑Substituted 1,4-Dihydropyridines with the Use of Bifunctional Thiourea-Ammonium Salts Bearing Different Counterions
Molecules 2010, 15(11), 8305-8326; https://doi.org/10.3390/molecules15118305
Received: 13 October 2010 / Revised: 8 November 2010 / Accepted: 12 November 2010 / Published: 15 November 2010
Cited by 17 | PDF Full-text (318 KB)
Abstract
Organoammonium salts composed of a Brønsted acid and an anilinothiourea promoted the Michael addition of β-keto esters and α,β-unsaturated aldehydes in the presence of primary amines to give functionalized 1,4-dihydropyridines enantioselectively. With the use of the different Brønsted acids such as DFA and
[...] Read more.
Organoammonium salts composed of a Brønsted acid and an anilinothiourea promoted the Michael addition of β-keto esters and α,β-unsaturated aldehydes in the presence of primary amines to give functionalized 1,4-dihydropyridines enantioselectively. With the use of the different Brønsted acids such as DFA and HBF4 with the same bifunctional thiourea, both enantiomers of 4-substituted 1,4-dihydropyridine were synthesized from the same starting materials. Full article
(This article belongs to the Special Issue Bifunctional Catalysis)
Figures

Graphical abstract

Open AccessArticle Towards the Development of Synthetic Routes Using Theoretical Calculations: An Application of In Silico Screening to 2,6-Dimethylchroman-4-one
Molecules 2010, 15(11), 8289-8304; https://doi.org/10.3390/molecules15118289
Received: 17 September 2010 / Revised: 9 November 2010 / Accepted: 11 November 2010 / Published: 15 November 2010
Cited by 4 | PDF Full-text (327 KB)
Abstract
This study describes an attempt to develop a synthetic route using theoretical calculations, i.e., in silico synthesis route development. The KOSP program created four potential synthetic routes for generating 2,6-dimethylchroman-4-one. In silico screening of these four synthetic routes was then performed. In
[...] Read more.
This study describes an attempt to develop a synthetic route using theoretical calculations, i.e., in silico synthesis route development. The KOSP program created four potential synthetic routes for generating 2,6-dimethylchroman-4-one. In silico screening of these four synthetic routes was then performed. In silico screening involves theoretical analysis of synthetic routes prior to actual experimental work. A synthetic route using the Mitsunobu reaction had already been reported by Hoddgets et al. Theoretical investigations were also conducted on two SNAr reactions as well as a Michael reaction before they were examined experimentally. In silico screening using DFT calculations indicated that only the Michael reaction was likely to produce the target. Experimental work confirmed that the target was obtained in a yield of 76.4% using the Michael reaction. The other two routes, except for the Mitsunobu reaction, failed to generate the target. Our results demonstrate that theoretical calculations can be used to narrow down the number of experiments that need to be conducted when developing novel synthetic routes. Full article
(This article belongs to the Special Issue From Computational Chemistry to Complex Networks)
Figures

Graphical abstract

Open AccessArticle MimoDB: a New Repository for Mimotope Data Derived from Phage Display Technology
Molecules 2010, 15(11), 8279-8288; https://doi.org/10.3390/molecules15118279
Received: 21 October 2010 / Revised: 4 November 2010 / Accepted: 12 November 2010 / Published: 15 November 2010
Cited by 36 | PDF Full-text (656 KB)
Abstract
Peptides selected from phage-displayed random peptide libraries are valuable in two aspects. On one hand, these peptides are candidates for new diagnostics, therapeutics and vaccines. On the other hand, they can be used to predict the networks or sites of protein-protein interactions. MimoDB,
[...] Read more.
Peptides selected from phage-displayed random peptide libraries are valuable in two aspects. On one hand, these peptides are candidates for new diagnostics, therapeutics and vaccines. On the other hand, they can be used to predict the networks or sites of protein-protein interactions. MimoDB, a new repository for these peptides, was developed, in which 10,716 peptides collected from 571 publications were grouped into 1,229 sets. Besides peptide sequences, other important information, such as the target, template, library and complex structure, was also included. MimoDB can be browsed and searched through a user-friendly web interface. For computational biologists, MimoDB can be used to derive customized data sets and benchmarks, which are useful for new algorithm development and tool evaluation. For experimental biologists, their results can be searched against the MimoDB database to exclude possible target-unrelated peptides. The MimoDB database is freely accessible at http://immunet.cn/mimodb/. Full article
(This article belongs to the Special Issue Phage Display of Combinatorial Libraries)
Open AccessReview Radiolabeled Small Molecule Protein Kinase Inhibitors for Imaging with PET or SPECT
Molecules 2010, 15(11), 8260-8278; https://doi.org/10.3390/molecules15118260
Received: 2 November 2010 / Revised: 10 November 2010 / Accepted: 11 November 2010 / Published: 15 November 2010
Cited by 40 | PDF Full-text (364 KB)
Abstract
Imaging protein kinase expression with radiolabeled small molecule inhibitors has been actively pursued to monitor the clinical potential of targeted therapeutics and treatments as well as to determine kinase receptor density changes related to disease progression. The goal of the present review is
[...] Read more.
Imaging protein kinase expression with radiolabeled small molecule inhibitors has been actively pursued to monitor the clinical potential of targeted therapeutics and treatments as well as to determine kinase receptor density changes related to disease progression. The goal of the present review is to provide an overview of the breadth of radiolabeled small molecules that have been synthesized to target intracellular protein kinases, not only for imaging in oncology, but also for other areas of interest, particularly the central nervous system. Considerable radiotracer development has focused on imaging receptor tyrosine kinases of growth factors, protein kinases A, B and C, and glycogen synthase kinase–3β. Design considerations, structural attributes and relevant biological results are summarized. Full article
(This article belongs to the Special Issue Radiochemistry)
Open AccessArticle Phenolic Compounds from Merremia umbellata subsp. orientalis and Their Allelopathic Effects on Arabidopsis Seed Germination
Molecules 2010, 15(11), 8241-8250; https://doi.org/10.3390/molecules15118241
Received: 15 September 2010 / Revised: 27 October 2010 / Accepted: 29 October 2010 / Published: 12 November 2010
Cited by 15 | PDF Full-text (297 KB)
Abstract
A bioassay-directed phytochemical study was carried out to investigate potential allelochemicals of the invasive plant Merremia umbellata subsp. orientalis (Hall. f.). Eight phenolic compounds, including a salicylic acid (SA)-derived new natural product, SA 2-O-β-D-(3',6'-dicaffeoyl)-glucopyranoside (1), and seven known ones
[...] Read more.
A bioassay-directed phytochemical study was carried out to investigate potential allelochemicals of the invasive plant Merremia umbellata subsp. orientalis (Hall. f.). Eight phenolic compounds, including a salicylic acid (SA)-derived new natural product, SA 2-O-β-D-(3',6'-dicaffeoyl)-glucopyranoside (1), and seven known ones 2-8 were isolated and identified from two bioactive sub-fractions of the acetone extract of this plant. The structure of new compound 1 was established by spectral and chemical methods. The potential allelopathic effects of these compounds at 0.5 and 1.0 mM concentrations on the germination of Arabidopsis seeds were tested. Results showed that 2 remarkably inhibited seed germination at concentrations as low as 0.5 mM. Compound 3 only moderately inhibited seed germination at 0.5 mM, but displayed strong inhibitory bioactivity at 1.0 mM concentration. Compounds 4 and 5 showed only slight inhibitory bioactivity at 1.0 mM, while the other compounds showed no obvious inhibitory effects. Full article
(This article belongs to the Section Natural Products Chemistry)
Figures

Graphical abstract

Open AccessCommunication Study on Suitability of KOD DNA Polymerase for Enzymatic Production of Artificial Nucleic Acids Using Base/Sugar Modified Nucleoside Triphosphates
Molecules 2010, 15(11), 8229-8240; https://doi.org/10.3390/molecules15118229
Received: 30 September 2010 / Revised: 6 November 2010 / Accepted: 10 November 2010 / Published: 12 November 2010
Cited by 19 | PDF Full-text (325 KB)
Abstract
Recently, KOD and its related DNA polymerases have been used for preparing various modified nucleic acids, including not only base-modified nucleic acids, but also sugar-modified ones, such as bridged/locked nucleic acid (BNA/LNA) which would be promising candidates for nucleic acid drugs. However, thus
[...] Read more.
Recently, KOD and its related DNA polymerases have been used for preparing various modified nucleic acids, including not only base-modified nucleic acids, but also sugar-modified ones, such as bridged/locked nucleic acid (BNA/LNA) which would be promising candidates for nucleic acid drugs. However, thus far, reasons for the effectiveness of KOD DNA polymerase for such purposes have not been clearly elucidated. Therefore, using mutated KOD DNA polymerases, we studied here their catalytic properties upon enzymatic incorporation of nucleotide analogues with base/sugar modifications. Experimental data indicate that their characteristic kinetic properties enabled incorporation of various modified nucleotides. Among those KOD mutants, one achieved efficient successive incorporation of bridged nucleotides with a 2′-ONHCH2CH2-4′ linkage. In this study, the characteristic kinetic properties of KOD DNA polymerase for modified nucleoside triphosphates were shown, and the effectiveness of genetic engineering in improvement of the enzyme for modified nucleotide polymerization has been demonstrated. Full article
Figures

Graphical abstract

Open AccessArticle Crucial Role of Selenium in the Virucidal Activity of Benzisoselenazol-3(2H)-ones and Related Diselenides
Molecules 2010, 15(11), 8214-8228; https://doi.org/10.3390/molecules15118214
Received: 29 October 2010 / Revised: 5 November 2010 / Accepted: 9 November 2010 / Published: 12 November 2010
Cited by 25 | PDF Full-text (223 KB)
Abstract
Various N-substituted benzisoselenazol-3(2H)-ones and their non-selenium-containing analogues have been synthesized and tested against selected viruses (HHV-1, EMCV and VSV) to determine the extent to which selenium plays a role in antiviral activity. The data presented here show that the presence
[...] Read more.
Various N-substituted benzisoselenazol-3(2H)-ones and their non-selenium-containing analogues have been synthesized and tested against selected viruses (HHV-1, EMCV and VSV) to determine the extent to which selenium plays a role in antiviral activity. The data presented here show that the presence of selenium is crucial for the antiviral properties of benzisoselenazol-3(2H)-ones since their isostructural analogues having different groups but lacking selenium either did not show any antiviral activity or their activity was substantially lower. The open-chain analogues of benzisoselenazol-3(2H)-ones—diselenides also exhibited high antiviral activity while selenides and disulfides were completely inactive towards model viruses. Full article
(This article belongs to the Special Issue Antivirals)
Figures

Graphical abstract

Open AccessArticle A Highly Efficient Bismuth Salts-Catalyzed Route for the Synthesis of α-Aminophosphonates
Molecules 2010, 15(11), 8205-8213; https://doi.org/10.3390/molecules15118205
Received: 24 September 2010 / Revised: 5 October 2010 / Accepted: 9 November 2010 / Published: 12 November 2010
Cited by 29 | PDF Full-text (267 KB)
Abstract
A convenient synthesis of different types of α-amino phosphonates via one-pot solvent-free three component reactions of aldehydes, amines and phosphites catalyzed by bismuth salts has been investigated. Bismuth triflate is found to be the most effective catalyst for this reaction. Full article
(This article belongs to the Special Issue Organobismuth Chemistry)
Open AccessArticle Chemical Constituents of the Bark of Dipteryx alata Vogel, an Active Species against Bothrops jararacussu Venom
Molecules 2010, 15(11), 8193-8204; https://doi.org/10.3390/molecules15118193
Received: 25 September 2010 / Revised: 4 November 2010 / Accepted: 10 November 2010 / Published: 12 November 2010
Cited by 31 | PDF Full-text (126 KB)
Abstract
The effect of four sub-extracts prepared from the lyophilized hydroalcoholic bark of Dipteryx alata (Leguminosae-Papilionoideae) dissolved in a methanol-water (80:20) mixture through a liquid-liquid partition procedure has been investigated against the neuromuscular blockade of the venom of the snake Bothrops jararacussu. The
[...] Read more.
The effect of four sub-extracts prepared from the lyophilized hydroalcoholic bark of Dipteryx alata (Leguminosae-Papilionoideae) dissolved in a methanol-water (80:20) mixture through a liquid-liquid partition procedure has been investigated against the neuromuscular blockade of the venom of the snake Bothrops jararacussu. The active CH2Cl2 sub-extract has been extensively analyzed for its chemical constituents, resulting in the isolation of four lupane-type triterpenoids: lupeol (1), lupenone (2), 28-hydroxylup-20(29)-en-3-one (3), betulin (4), nine isoflavonoids: 8-O-methylretusin (5), 7-hydroxy-5,6,4’-trimethoxyisoflavone (6), afrormosin (8), 7-hydroxy-8,3’,4’-trimethoxyisoflavone (9), 7,3’-dihydroxy-8,4’-dimethoxyisoflavone (10), odoratin (11), 7,8,3’-trihydroxy-4’-methoxyisoflavone (13), 7,8,3’-trihydroxy-6,4’-dimethoxyisoflavone (15), dipteryxin (17), one chalcone: isoliquiritigenin (7), one aurone: sulfuretin (14) and three phenolic compounds: vanillic acid (12), vanillin (16), and protocatechuic acid (18). Their chemical structures were elucidated on the basis of spectroscopic analysis, including HRMS, 1D- and 2D-NMR techniques. Full article
(This article belongs to the Section Natural Products Chemistry)
Figures

Graphical abstract

Open AccessArticle Analysis of Protein Pathway Networks Using Hybrid Properties
Molecules 2010, 15(11), 8177-8192; https://doi.org/10.3390/molecules15118177
Received: 5 August 2010 / Revised: 11 November 2010 / Accepted: 12 November 2010 / Published: 12 November 2010
Cited by 48 | PDF Full-text (188 KB) | Supplementary Files
Abstract
Given a protein-forming system, i.e., a system consisting of certain number of different proteins, can it form a biologically meaningful pathway? This is a fundamental problem in systems biology and proteomics. During the past decade, a vast amount of information on different
[...] Read more.
Given a protein-forming system, i.e., a system consisting of certain number of different proteins, can it form a biologically meaningful pathway? This is a fundamental problem in systems biology and proteomics. During the past decade, a vast amount of information on different organisms, at both the genetic and metabolic levels, has been accumulated and systematically stored in various specific databases, such as KEGG, ENZYME, BRENDA, EcoCyc and MetaCyc. These data have made it feasible to address such an essential problem. In this paper, we have analyzed known regulatory pathways in humans by extracting different (biological and graphic) features from each of the 17,069 protein-formed systems, of which 169 are positive pathways, i.e., known regulatory pathways taken from KEGG; while 16,900 were negative, i.e., not formed as a biologically meaningful pathway. Each of these protein-forming systems was represented by 352 features, of which 88 are graph features and 264 biological features. To analyze these features, the “Minimum Redundancy Maximum Relevance” and the “Incremental Feature Selection” techniques were utilized to select a set of 22 optimal features to query whether a protein-forming system is able to form a biologically meaningful pathway or not. It was found through cross-validation that the overall success rate thus obtained in identifying the positive pathways was 79.88%. It is anticipated that, this novel approach and encouraging result, although preliminary yet, may stimulate extensive investigations into this important topic. Full article
(This article belongs to the Special Issue From Computational Chemistry to Complex Networks)
Open AccessArticle 5,6-Didehydroginsenosides from the Roots of Panax notoginseng
Molecules 2010, 15(11), 8169-8176; https://doi.org/10.3390/molecules15118169
Received: 3 November 2010 / Revised: 8 November 2010 / Accepted: 10 November 2010 / Published: 11 November 2010
Cited by 17 | PDF Full-text (219 KB)
Abstract
Two minor novel dammarane-type saponins—5,6-didehydroginsenoside Rd (1) and 5,6-didehydroginsenoside Rb1 (2)—were isolated from the dried roots of Panax notoginseng along with sixteen known saponins. The structures of the new compounds were elucidated on the basis of spectroscopic and chemical methods. Full article
Open AccessArticle Oligomerization of 3,5-Dimethyl Benzyl Alcohol Promoted by Clay: Experimental and Theoretical Study
Molecules 2010, 15(11), 8156-8168; https://doi.org/10.3390/molecules15118156
Received: 8 August 2010 / Revised: 22 October 2010 / Accepted: 27 October 2010 / Published: 11 November 2010
Cited by 8 | PDF Full-text (1156 KB)
Abstract
Linear oligomerization of 3,5-dimethyl benzyl alcohol is induced by a montmorillonite clay (Tonsil Optimum Extra), producing 1,3,5,7-tetramethyl-9,10-dihydro-anthracene, which, by loss of protons results in the product 1,3,5,7-tetramethylanthracene. It was also found that the compounds 4-(3´,5´-dimethylbenzyl)-1,3,5,7-tetramethyl-9,10-dihydroanthracece and 4-(3´,5´-dimethylbenzyl)-1,3,5,7-tetra-methylanthracene were formed from 1,3,5,7-tetramethyl-9,10-dihydroanthracene. 1,3,5,7-Tetramethylanthryl radical
[...] Read more.
Linear oligomerization of 3,5-dimethyl benzyl alcohol is induced by a montmorillonite clay (Tonsil Optimum Extra), producing 1,3,5,7-tetramethyl-9,10-dihydro-anthracene, which, by loss of protons results in the product 1,3,5,7-tetramethylanthracene. It was also found that the compounds 4-(3´,5´-dimethylbenzyl)-1,3,5,7-tetramethyl-9,10-dihydroanthracece and 4-(3´,5´-dimethylbenzyl)-1,3,5,7-tetra-methylanthracene were formed from 1,3,5,7-tetramethyl-9,10-dihydroanthracene. 1,3,5,7-Tetramethylanthryl radical cation was formed from 1,3,5,7-tetramethyl-9,10-dihydroanthracene; it was characterized by Electronic Paramagnetic Resonance (EPR). On the other hand, a theoretical analysis was performed, allowing the rationalization of the observed products and some of the key reaction steps. Full article
(This article belongs to the Section Organic Chemistry)
Open AccessArticle 2-Chlorophenyl Zinc Bromide: A Convenient Nucleophile for the Mannich-Related Multicomponent Synthesis of Clopidogrel and Ticlopidine
Molecules 2010, 15(11), 8144-8155; https://doi.org/10.3390/molecules15118144
Received: 8 October 2010 / Revised: 2 November 2010 / Accepted: 9 November 2010 / Published: 11 November 2010
Cited by 10 | PDF Full-text (155 KB)
Abstract
A methodological study devoted to the Mannich-like multicomponent synthesis of the antiplatelet agent (±)‑clopidogrel (7) and the ethyl ester analogue 6 is described. The process involves the formation of 2-chlorophenyl zinc bromide (2) and its subsequent reaction with an
[...] Read more.
A methodological study devoted to the Mannich-like multicomponent synthesis of the antiplatelet agent (±)‑clopidogrel (7) and the ethyl ester analogue 6 is described. The process involves the formation of 2-chlorophenyl zinc bromide (2) and its subsequent reaction with an alkyl glyoxylate and 4,5,6,7-tetrahydrothieno[3,2-c]pyridine (3). We demonstrate that the organozinc reagent 2 also constitutes a very convenient nucleophile for the multicomponent synthesis of the benzylamine core of ticlopidine (9). Full article
Open AccessCorrection Al-Salahi, R. Synthesis and Reactivity of [1,2,4]Triazolo-annelated Quinazolines. Molecules 2010, 15, 7016-7034
Molecules 2010, 15(11), 8143; https://doi.org/10.3390/molecules15118143
Received: 9 November 2010 / Accepted: 10 November 2010 / Published: 10 November 2010
PDF Full-text (17 KB)
Abstract
The authors wish to make the following corrections to the paper published in Molecules [1]: The authorship of the paper is changed to Rashad A. Al-Salahi and Detlef Geffken. [...] Full article
Back to Top