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 16, Issue 3 (March 2011), Pages 1917-2742

  • 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 1-57
Export citation of selected articles as:

Research

Jump to: Review

Open AccessArticle Anti-Inflammatory and Antioxidant Components from Hygroryza aristata
Molecules 2011, 16(3), 1917-1927; doi:10.3390/molecules16031917
Received: 4 January 2011 / Revised: 21 February 2011 / Accepted: 23 February 2011 / Published: 25 February 2011
Cited by 8 | PDF Full-text (356 KB)
Abstract
Twenty-six known compounds and two new compounds, including a new lignan, (7S*,8R*,7’R*,8’S*)-icariol A2-9-O-b-xylopyranoside (1), and a new indole alkaloid, hygarine (2), were isolated from the extracts [...] Read more.
Twenty-six known compounds and two new compounds, including a new lignan, (7S*,8R*,7’R*,8’S*)-icariol A2-9-O-b-xylopyranoside (1), and a new indole alkaloid, hygarine (2), were isolated from the extracts of Hygroryza aristata (Gramineae). The structures of all compounds were elucidated on the basis of NMR spectral analysis. The compounds (-)-epigallocatechin-3-O-gallate (4) and (-)-epicatechin-3-O-gallate (5) possess free radical scavenging activities and compound 1 could inhibit superoxide anion generation and elastase release by fMLP/CB-induced human neutrophils with IC50 values of 19.33 ± 0.86 and 24.14 ± 1.59 mM, respectively. Full article
(This article belongs to the Section Natural Products)
Open AccessArticle QSAR Models for CXCR2 Receptor Antagonists Based on the Genetic Algorithm for Data Preprocessing Prior to Application of the PLS Linear Regression Method and Design of the New Compounds Using In Silico Virtual Screening
Molecules 2011, 16(3), 1928-1955; doi:10.3390/molecules16031928
Received: 4 January 2011 / Revised: 31 January 2011 / Accepted: 15 February 2011 / Published: 25 February 2011
Cited by 14 | PDF Full-text (350 KB)
Abstract
The CXCR2 receptors play a pivotal role in inflammatory disorders and CXCR2 receptor antagonists can in principle be used in the treatment of inflammatory and related diseases. In this study, quantitative relationships between the structures of 130 antagonists of the CXCR2 receptors [...] Read more.
The CXCR2 receptors play a pivotal role in inflammatory disorders and CXCR2 receptor antagonists can in principle be used in the treatment of inflammatory and related diseases. In this study, quantitative relationships between the structures of 130 antagonists of the CXCR2 receptors and their activities were investigated by the partial least squares (PLS) method. The genetic algorithm (GA) has been proposed for improvement of the performance of the PLS modeling by choosing the most relevant descriptors. The results of the factor analysis show that eight latent variables are able to describe about 86.77% of the variance in the experimental activity of the molecules in the training set. Power prediction of the QSAR models developed with SMLR, PLS and GA-PLS methods were evaluated using cross-validation, and validation through an external prediction set. The results showed satisfactory goodness-of-fit, robustness and perfect external predictive performance. A comparison between the different developed methods indicates that GA-PLS can be chosen as supreme model due to its better prediction ability than the other two methods. The applicability domain was used to define the area of reliable predictions. Furthermore, the in silico screening technique was applied to the proposed QSAR model and the structure and potency of new compounds were predicted. The developed models were found to be useful for the estimation of pIC50 of CXCR2 receptors for which no experimental data is available. Full article
(This article belongs to the Section Medicinal Chemistry)
Open AccessArticle Synthesis of New Visnagen and Khellin Furochromone Pyrimidine Derivatives and Their Anti-Inflammatory and Analgesic Activity
Molecules 2011, 16(3), 1956-1972; doi:10.3390/molecules16031956
Received: 17 January 2011 / Revised: 11 February 2011 / Accepted: 17 February 2011 / Published: 25 February 2011
Cited by 11 | PDF Full-text (211 KB)
Abstract
6-[(4-Methoxy/4,9-dimethoxy)-7-methylfurochromen-5-ylideneamino]-2-thioxo-2,3-dihydropyrimidin-4-ones 1a,b were prepared by reaction of 6-amino-2-thiouracil with visnagen or khellin, respectively. Reaction of 1a,b with methyl iodide afforded furochromenylideneaminomethylsulfanylpyrimidin-4-ones 2a,b. Compounds 2a,b were reacted with secondary aliphatic amines to give the corresponding furochromen-ylideneamino-2-substituted pyrimidin-4-ones 3a–d. Reaction of 3a–d [...] Read more.
6-[(4-Methoxy/4,9-dimethoxy)-7-methylfurochromen-5-ylideneamino]-2-thioxo-2,3-dihydropyrimidin-4-ones 1a,b were prepared by reaction of 6-amino-2-thiouracil with visnagen or khellin, respectively. Reaction of 1a,b with methyl iodide afforded furochromenylideneaminomethylsulfanylpyrimidin-4-ones 2a,b. Compounds 2a,b were reacted with secondary aliphatic amines to give the corresponding furochromen-ylideneamino-2-substituted pyrimidin-4-ones 3a–d. Reaction of 3a–d with phosphorus oxychloride yielded 6-chlorofurochromenylidenepyrimidinamines 4a–d, which were reacted with secondary amines to afford furochromenylideneamino-2,6-disubstituted pyrimidin-4-ones 5a–d. In addition, reaction of 5a–d with 3-chloropentane-2,4-dione gave 3-chloro-furochromenylpyrimidopyrimidines 6a–d. The latter were reacted with piperazine and morpholine to give 1-(furochromenyl)-pyrimidopyrimidine-3,6,8-triylpiperazines or -3,6,8-triylmorpholines 7a–d. The chemical structures of the newly synthesized compound ware characterized by IR, 1H-NMR, 13C-NMR and mass spectral analysis. These compounds were also screened for their analgesic and anti-inflammatory activities. Some of them, particularly 3–7, exhibited promising activities. Full article
(This article belongs to the Special Issue Cycloaddition Reactions in Organic Synthesis)
Open AccessArticle Effect of End Groups on the Raman Spectra of Lycopene and β-Carotene under High Pressure
Molecules 2011, 16(3), 1973-1980; doi:10.3390/molecules16031973
Received: 25 November 2010 / Revised: 8 February 2011 / Accepted: 10 February 2011 / Published: 25 February 2011
Cited by 9 | PDF Full-text (394 KB)
Abstract
The Raman spectra of all-trans-lycopene in n-hexane were measured under high pressure, and the results compared with those of β-carotene. The different pressure effects on Raman spectra are analyzed taking into account the different structures of lycopene [...] Read more.
The Raman spectra of all-trans-lycopene in n-hexane were measured under high pressure, and the results compared with those of β-carotene. The different pressure effects on Raman spectra are analyzed taking into account the different structures of lycopene and β-carotene molecules. It is concluded that: (a) the vibronic coupling between the S1 and S0 states of β-carotene is stronger than that of lycopene, (b) the diabatic frequency increment of the ν1 mode is more susceptible to pressure than that of the ν2 mode for lycopene, and (c) β-rings rotation can relieve the pressure effect on the C=C bond length in β-carotene. This work provides some insights for elucidating the structural and environmental effects on Raman spectra of carotenoids. Full article
Figures

Open AccessCommunication A Simple and Practical Solvent-Free Preparation of Polymaleimide
Molecules 2011, 16(3), 1981-1986; doi:10.3390/molecules16031981
Received: 13 January 2011 / Revised: 8 February 2011 / Accepted: 9 February 2011 / Published: 28 February 2011
Cited by 4 | PDF Full-text (187 KB)
Abstract
Polymaleimide (PMAI) was synthesized by reacting polymaleic anhydride (PMA) with urea via a solvent-free reaction at 180 °C. The conversion of PMA could reach 95%. This method is simple, practical and environmentally-friendly. The structure of the resulting PMAI was characterized by 1 [...] Read more.
Polymaleimide (PMAI) was synthesized by reacting polymaleic anhydride (PMA) with urea via a solvent-free reaction at 180 °C. The conversion of PMA could reach 95%. This method is simple, practical and environmentally-friendly. The structure of the resulting PMAI was characterized by 1H-NMR and IR. Full article
Open AccessArticle Drug Resistance Modulation in Staphylococcus Aureus, a New Biological Activity for Mesoionic Hydrochloride Compounds
Molecules 2011, 16(3), 2023-2031; doi:10.3390/molecules16032023
Received: 25 January 2011 / Revised: 19 February 2011 / Accepted: 22 February 2011 / Published: 28 February 2011
Cited by 9 | PDF Full-text (207 KB)
Abstract
Two salts of the mesoionic compounds 1,4-diphenyl-5-(5-nitro-2-furanyl)-1,3,4-thiadiazolium-2-thiol chloride (MC-1) and 4-phenyl-5-(5-nitro-2-furanyl)-1,3,4-thiadiazolium-2-phenylamine chloride (MC-2) were synthesized utilizing 1,4-diphenyl-thiosemicarbazide and 5-nitro-2-furoyl chloride as starting materials. Their structures were characterized by IR, 1H-NMR, 13C-NMR and elemental analysis. These compounds [...] Read more.
Two salts of the mesoionic compounds 1,4-diphenyl-5-(5-nitro-2-furanyl)-1,3,4-thiadiazolium-2-thiol chloride (MC-1) and 4-phenyl-5-(5-nitro-2-furanyl)-1,3,4-thiadiazolium-2-phenylamine chloride (MC-2) were synthesized utilizing 1,4-diphenyl-thiosemicarbazide and 5-nitro-2-furoyl chloride as starting materials. Their structures were characterized by IR, 1H-NMR, 13C-NMR and elemental analysis. These compounds were analyzed for their influence on the effectiveness of norfloxacin, tetracycline, and erythromycin (standard antibiotics) against resistant strains of Staphylococcus aureus. MC-1 and MC-2, at sub-inhibitory concentrations of 16 μg/mL, favourably modulated the antibiotic activity of tetracycline by 16- and 32-fold, respectively (MIC), and that of erythromycin by 4-fold. Full article
(This article belongs to the Special Issue Advances in Heterocyclic Chemistry)
Figures

Open AccessArticle Potent Anti-Platelet Constituents from Centaurea iberica
Molecules 2011, 16(3), 2053-2064; doi:10.3390/molecules16032053
Received: 3 January 2011 / Revised: 24 February 2011 / Accepted: 26 February 2011 / Published: 28 February 2011
Cited by 9 | PDF Full-text (327 KB)
Abstract
New naturally occurring nitrogenous compounds 1 and 2, along with a new dimeric lignan glucoside 3, have been isolated from the ethyl acetate soluble fraction of Centaurea iberica. Their structures have been elucidated through spectroscopic techniques. All the isolated [...] Read more.
New naturally occurring nitrogenous compounds 1 and 2, along with a new dimeric lignan glucoside 3, have been isolated from the ethyl acetate soluble fraction of Centaurea iberica. Their structures have been elucidated through spectroscopic techniques. All the isolated compounds showed significant platelet aggregation inhibition. Full article
Open AccessArticle From Symmetric Glycerol Derivatives to Dissymmetric Chlorohydrins
Molecules 2011, 16(3), 2065-2074; doi:10.3390/molecules16032065
Received: 9 December 2010 / Revised: 16 February 2011 / Accepted: 28 February 2011 / Published: 2 March 2011
Cited by 4 | PDF Full-text (146 KB)
Abstract
The anticipated worldwide increase in biodiesel production will result in an accumulation of glycerol for which there are insufficient conventional uses. The surplus of this by-product has increased rapidly during the last decade, prompting a search for new glycerol applications. We describe [...] Read more.
The anticipated worldwide increase in biodiesel production will result in an accumulation of glycerol for which there are insufficient conventional uses. The surplus of this by-product has increased rapidly during the last decade, prompting a search for new glycerol applications. We describe here the synthesis of dissymmetric chlorohydrin esters from symmetric 1,3-dichloro-2-propyl esters obtained from glycerol. We studied the influence of two solvents: 1,4-dioxane and 1-butanol and two bases: sodium carbonate and 1-butylimidazole, on the synthesis of dissymmetric chlorohydrin esters. In addition, we studied the influence of other bases (potassium and lithium carbonates) in the reaction using 1,4-dioxane as the solvent. The highest yield was obtained using 1,4-dioxane and sodium carbonate. Full article
(This article belongs to the Special Issue Asymmetric Synthesis)
Figures

Open AccessArticle In Vitro Inhibitory Effects of Cyandin-3-rutinoside on Pancreatic α-Amylase and Its Combined Effect with Acarbose
Molecules 2011, 16(3), 2075-2083; doi:10.3390/molecules16032075
Received: 10 January 2011 / Revised: 7 February 2011 / Accepted: 28 February 2011 / Published: 2 March 2011
Cited by 17 | PDF Full-text (250 KB)
Abstract
The inhibitory activity on pancreatic α-amylase by cyanidin-3-rutinoside was examined in vitro. The IC50 value of cyanidin-3-rutinoside against pancreatic α-amylase was 24.4 ± 0.1 μM. The kinetic analysis revealed that pancreatic α-amylase was inhibited by cyanidin-3-rutinoside in a non-competitive manner. [...] Read more.
The inhibitory activity on pancreatic α-amylase by cyanidin-3-rutinoside was examined in vitro. The IC50 value of cyanidin-3-rutinoside against pancreatic α-amylase was 24.4 ± 0.1 μM. The kinetic analysis revealed that pancreatic α-amylase was inhibited by cyanidin-3-rutinoside in a non-competitive manner. The additive inhibition of a combination of cyanidin-3-rutinoside with acarbose against pancreatic α-amylase was also found. These results provide the first evidence for the effect of cyanidin-3-rutinoside in a retarded absorption of carbohydrates by inhibition of pancreatic α-amylase which may be useful as a potential inhibitor for prevention and treatment of diabetes mellitus. Full article
(This article belongs to the Section Medicinal Chemistry)
Open AccessArticle Luteolin Isolated from the Medicinal Plant Elsholtzia rugulosa (Labiatae) Prevents Copper-Mediated Toxicity in β-Amyloid Precursor Protein Swedish Mutation Overexpressing SH-SY5Y Cells
Molecules 2011, 16(3), 2084-2096; doi:10.3390/molecules16032084
Received: 14 February 2011 / Revised: 22 February 2011 / Accepted: 25 February 2011 / Published: 2 March 2011
Cited by 18 | PDF Full-text (2709 KB)
Abstract
Luteolin, a 3’,4’,5,7-tetrahydroxyflavone, is a plant flavonoid and pharmacologically active agent that has been isolated from several plant species. In the present study, the effects of luteolin obtained from the medicinal plant Elsholtzia rugulosa and the related mechanisms were examined in an [...] Read more.
Luteolin, a 3’,4’,5,7-tetrahydroxyflavone, is a plant flavonoid and pharmacologically active agent that has been isolated from several plant species. In the present study, the effects of luteolin obtained from the medicinal plant Elsholtzia rugulosa and the related mechanisms were examined in an Alzheimer's disease (AD) cell model. In this model, copper was used to exacerbate the neurotoxicity in β-amyloid precursor protein Swedish mutation stably overexpressed SH-SY5Y cells (named “APPsw cells” for short). Based on this model, we demonstrated that luteolin increased cell viability, reduced intracellular ROS generation, enhanced the activity of SOD and reversed mitochondrial membrane potential dissipation. Inhibition of caspase-related apoptosis was consistently involved in the neuroprotection afforded by luteolin. Furthermore, it down-regulated the expression of AβPP and lowered the secretion of Aβ1-42. These results indicated that luteolin from the Elsholtzia rugulosa exerted neroprotective effects through mechanisms that decrease AβPP expression, lower Aβ secretion, regulate the redox imbalance, preserve mitochondrial function, and depress the caspase family-related apoptosis. Full article
(This article belongs to the Section Natural Products)
Open AccessArticle Detection of Cytotoxic Activity of Lectin on Human Colon Adenocarcinoma (Sw480) and Epithelial Cervical Carcinoma (C33-A)
Molecules 2011, 16(3), 2107-2118; doi:10.3390/molecules16032107
Received: 16 December 2010 / Revised: 25 February 2011 / Accepted: 28 February 2011 / Published: 2 March 2011
Cited by 7 | PDF Full-text (238 KB)
Abstract
Lectins comprise a heterogeneous class of proteins that recognize the carbohydrate moieties of glycoconjugates with high specificity. Numerous studies have shown that lectins are capable of recognizing specific carbohydrate moieties displayed by malignant cells or tissues. The present work was performed to [...] Read more.
Lectins comprise a heterogeneous class of proteins that recognize the carbohydrate moieties of glycoconjugates with high specificity. Numerous studies have shown that lectins are capable of recognizing specific carbohydrate moieties displayed by malignant cells or tissues. The present work was performed to investigate the effects of tepary bean (Phaseolus acutifolius) lectins on proliferation, colony formation, and alteration of DNA synthesis of human malignant cells. Tepary bean lectin showed dose dependent  effects on the inhibition of viability as well as on colony formation in two human malignant cells lines (C33-A, Sw480); By contrast, tepary bean lectin only showed significant effects on DNA synthesis on Sw480 cells. Our results provide evidence of the anti- proliferative and cytotoxic effects of the tepary bean lectins on C33-A and Sw480 cells lines. Full article
(This article belongs to the Section Molecular Diversity)
Open AccessArticle Tamm-Horsfall Glycoprotein Enhances PMN Phagocytosis by Binding to Cell Surface-Expressed Lactoferrin and Cathepsin G That Activates MAP Kinase Pathway
Molecules 2011, 16(3), 2119-2134; doi:10.3390/molecules16032119
Received: 7 December 2010 / Revised: 15 February 2011 / Accepted: 28 February 2011 / Published: 3 March 2011
Cited by 9 | PDF Full-text (2235 KB)
Abstract
The molecular basis of polymorphonuclear neutrophil (PMN) phagocytosis-enhancing activity (PEA) by human purified urinary Tamm-Horsfall glyco- protein (THP) has not been elucidated. In this study, we found human THP bound to lactoferrin (LF) and cathepsin G (CG) expressed on the surface of [...] Read more.
The molecular basis of polymorphonuclear neutrophil (PMN) phagocytosis-enhancing activity (PEA) by human purified urinary Tamm-Horsfall glyco- protein (THP) has not been elucidated. In this study, we found human THP bound to lactoferrin (LF) and cathepsin G (CG) expressed on the surface of PMN, identified by a proteomic study with MALDI-TOF- LC/LC/mass spectrometric analysis. Pre-incubation of 10% SDS-PAGE electrophoresed PMN lysates with monoclonal anti-LF or anti-CG antibody reduced the binding with THP. To elucidate the signaling pathway of THP on PMN activation, we found THP enhanced ERK1/2 phosphorylation, reduced p38 MAP kinase phosphorylation, but had no effect on DNA binding of the five NF-kB family members in PMN. To further clarify whether the carbohydrate-side chains or protein-core structure in THP molecule is responsible for THP-PEA, THP was cleaved by different degrading enzymes with carbohydrate specificity (neuraminidase and β-galactosidase), protein specificity (V8 protease and proteinase K) or glycoconjugate specificity (carboxylpeptidase Y and O-sialoglycoprotein endopeptidase). We clearly demonstrated that the intact protein-core structure in THP molecule was more important for THP-PEA than carbohydrate-side chains. Putting these results together, we conclude that THP adheres to surface-expressed LF and CG on PMN and transduces signaling via the MAP kinase pathway to enhance PMN phagocytosis. Full article
(This article belongs to the Special Issue Glycosides)
Open AccessArticle In-Vitro Antibacterial Properties of Crude Aqueous and n-Hexane Extracts of the Husk of Cocos nucifera
Molecules 2011, 16(3), 2135-2145; doi:10.3390/molecules16032135
Received: 15 February 2011 / Revised: 24 February 2011 / Accepted: 28 February 2011 / Published: 3 March 2011
Cited by 7 | PDF Full-text (136 KB)
Abstract
The increasing numbers of cases of antibiotic resistance among pathogenic bacteria such as Vibrio species poses a major problem to the food and aquaculture industries, as most antibiotics are no longer effective in controlling pathogenic bacteria affecting these industries. Therefore, this study [...] Read more.
The increasing numbers of cases of antibiotic resistance among pathogenic bacteria such as Vibrio species poses a major problem to the food and aquaculture industries, as most antibiotics are no longer effective in controlling pathogenic bacteria affecting these industries. Therefore, this study was carried out to assess the antibacterial potentials of crude aqueous and n-hexane extracts of the husk of Cocos nucifera against some selected Vibrio species and other bacterial pathogens including those normally implicated in food and wound infections. The crude extracts were screened against forty-five strains of Vibrio pathogens and twenty-five other bacteria isolates made up of ten Gram positive and fifteen Gram negative bacteria. The aqueous extract was active against 17 of the tested bacterial and 37 of the Vibrio isolates; while the n-hexane extract showed antimicrobial activity against 21 of the test bacteria and 38 of the test Vibrio species. The minimum inhibitory concentrations (MICs) of the aqueous and n-hexane extracts against the susceptible bacteria ranged between 0.6–5.0 mg/mL and 0.3–5.0 mg/mL respectively, while the time kill study result for the aqueous extract ranged between 0.12 Log10 and 4.2 Log10 cfu/mL after 8 hours interaction in 1 × MIC and 2 × MIC. For the n-hexane extract, the log reduction ranged between 0.56 Log10 and 6.4 Log10 cfu/mL after 8 hours interaction in 1 × MIC and 2 × MIC. This study revealed the huge potential of C. nucifera extracts as alternative therapies against microbial infections. Full article
(This article belongs to the Section Natural Products)
Open AccessArticle Microwave-Assisted Extraction of Phenolic Antioxidants from Potato Peels
Molecules 2011, 16(3), 2218-2232; doi:10.3390/molecules16032218
Received: 6 January 2011 / Revised: 2 March 2011 / Accepted: 4 March 2011 / Published: 7 March 2011
Cited by 28 | PDF Full-text (904 KB)
Abstract
A response surface method was used to optimize the microwave-assisted extraction parameters such as extraction time (t) (min), solvent (methanol) concentration (S) (v/v) and microwave power level (MP) for extraction of antioxidants from potato peels. Max. [...] Read more.
A response surface method was used to optimize the microwave-assisted extraction parameters such as extraction time (t) (min), solvent (methanol) concentration (S) (v/v) and microwave power level (MP) for extraction of antioxidants from potato peels. Max. total phenolics content of 3.94 mg g−1 dry weight (dw) was obtained at S of 67.33%, t of 15 min and a MP of 14.67%. For ascorbic acid (1.44 mg g−1 dw), caffeic acid (1.33 mg g−1 dw), ferulic acid (0.50 mg g−1 dw) max contents were obtained at S of 100%, t of 15 min, and MP of 10%, while the max chlorogenic acid content (1.35 mg g−1 dw) was obtained at S of 100%, t of 5 min, and MP of 10%. The radical scavenging activity of the extract was evaluated by using the DPPH assay and optimum antioxidant activity was obtained at S of 100%, t of 5 min, and MP of 10%. Full article
Figures

Open AccessCommunication In Vitro Cytotoxic Evaluation of a Novel Phosphinyl Derivative of Boldine
Molecules 2011, 16(3), 2253-2258; doi:10.3390/molecules16032253
Received: 10 January 2011 / Revised: 23 February 2011 / Accepted: 4 March 2011 / Published: 7 March 2011
PDF Full-text (205 KB)
Abstract
2,9-Dimethoxymethylboldine (2), 2,9-dimethoxymethyl-3-bromoboldine (3) and 2,9-dimethoxymethyl-3-diphenylphosphinylboldine (4) have been synthesized in an effort to find compounds with potential pharmacological applications. The cytotoxic activities of the natural precursor 1 and these three derivatives have been measured as [...] Read more.
2,9-Dimethoxymethylboldine (2), 2,9-dimethoxymethyl-3-bromoboldine (3) and 2,9-dimethoxymethyl-3-diphenylphosphinylboldine (4) have been synthesized in an effort to find compounds with potential pharmacological applications. The cytotoxic activities of the natural precursor 1 and these three derivatives have been measured as IC50 inhibitory growth. The diphenylphosphinyl derivative 4 showed a significant cytotoxic activity on two breast cancer cell lines, namely MCF-7 and MDA-MB-231, with IC50 values of 55.5 and 62.7 [µM], respectively. These results suggest that the kind of structural modifications introduced to synthesize compound 4 represent a promising way to enhance the cytotoxic activity of boldine derivatives. Full article
(This article belongs to the Section Natural Products)
Open AccessArticle Diterpenoid Tanshinones and Phenolic Acids from Cultured Hairy Roots of Salvia miltiorrhiza Bunge and Their Antimicrobial Activities
Molecules 2011, 16(3), 2259-2267; doi:10.3390/molecules16032259
Received: 13 January 2011 / Revised: 21 February 2011 / Accepted: 4 March 2011 / Published: 7 March 2011
Cited by 24 | PDF Full-text (214 KB)
Abstract
Four diterpenoid tanshinones and three phenolic acids were isolated from the crude ethanol extract of the cultured hairy roots of Salvia miltiorrhiza Bunge by bioassay-guided fractionation. By means of physicochemical and spectrometric analysis, they were identified as tanshinone ΙΙA (1), [...] Read more.
Four diterpenoid tanshinones and three phenolic acids were isolated from the crude ethanol extract of the cultured hairy roots of Salvia miltiorrhiza Bunge by bioassay-guided fractionation. By means of physicochemical and spectrometric analysis, they were identified as tanshinone ΙΙA (1), tanshinone Ι (2), cryptotanshinone (3), dihydrotanshinone Ι (4), rosmarinic acid (5), caffeic acid (6), and danshensu (7). These compounds were evaluated to show a broad antimicrobial spectrum of activity on test microorganisms including eight bacterial and one fungal species. Among the four tanshinones, cryptotanshinone (3) and dihydrotanshinone Ι (4) exhibited stronger antimicrobial activity than tanshinone ΙΙA (1) and tanshinone Ι (2). The results indicated that the major portion of the antimicrobial activity was due to the presence of tanshinones and phenolic acids in S. miltiorrhiza hairy roots, which could be used as the materials for producing antimicrobial agents for use in agricultural practice in the future. Full article
(This article belongs to the collection Bioactive Compounds)
Open AccessArticle Lignans and Other Constituents from Aerial Parts of Haplophyllum Villosum
Molecules 2011, 16(3), 2268-2273; doi:10.3390/molecules16032268
Received: 14 January 2011 / Revised: 28 January 2011 / Accepted: 17 February 2011 / Published: 7 March 2011
Cited by 8 | PDF Full-text (122 KB)
Abstract
During our phytochemical investigation of Haplophyllum villosum (Rutaceae), a perennial herb from Iran, a new 4,8-diaryl-3,7-dioxobicyclo-(3,3,0)-octane type lignan, eudesmin A (1), together with four known compounds–eudesmin (2), haplamine (3), umbelliferone (4) and scopoletin ( [...] Read more.
During our phytochemical investigation of Haplophyllum villosum (Rutaceae), a perennial herb from Iran, a new 4,8-diaryl-3,7-dioxobicyclo-(3,3,0)-octane type lignan, eudesmin A (1), together with four known compounds–eudesmin (2), haplamine (3), umbelliferone (4) and scopoletin (5)–were isolated from aerial parts of the plant. The structures of the compounds were elucidated using NMR spectral analysis (1H-NMR, 13C-NMR, HSQC, COSY and HMBC) as well as UV, IR and MS spectra and comparison with previously reported data. Full article
(This article belongs to the collection Bioactive Compounds)
Open AccessArticle Synthesis and Biological Evaluation of 4-Aroyl-6,7,8-Trimethoxyquinolines as a Novel Class of Anticancer Agents
Molecules 2011, 16(3), 2274-2284; doi:10.3390/molecules16032274
Received: 28 January 2011 / Revised: 2 March 2011 / Accepted: 4 March 2011 / Published: 7 March 2011
PDF Full-text (212 KB)
Abstract
A series of 2-aroyl and 2-aryl-5,6,7-trimethoxyquinoline and 4-aroyl-6,7,8-trimethoxyquinoline combretastatin analogs were synthesized and evaluated for their potential anticancer activity. The 4-aroylquinoline 11 inhibited the growth of the human cancer cells lines KB, HT-29, and MKN45, as well as the three human resistant [...] Read more.
A series of 2-aroyl and 2-aryl-5,6,7-trimethoxyquinoline and 4-aroyl-6,7,8-trimethoxyquinoline combretastatin analogs were synthesized and evaluated for their potential anticancer activity. The 4-aroylquinoline 11 inhibited the growth of the human cancer cells lines KB, HT-29, and MKN45, as well as the three human resistant cancer cell lines KB-vin10, KB-S15, and KB-7D, with IC50 values of 217, 327, 239, 246, 213, and 252 nM, respectively. Full article
Figures

Open AccessArticle Antimicrobial Properties of Some Bis(Iminoacenaphthene (BIAN)-Supported N-Heterocyclic Carbene Complexes of Silver and Gold
Molecules 2011, 16(3), 2285-2292; doi:10.3390/molecules16032285
Received: 16 February 2011 / Revised: 28 February 2011 / Accepted: 7 March 2011 / Published: 9 March 2011
Cited by 15 | PDF Full-text (212 KB)
Abstract
The AgCl, AgOAc, AuCl, and AuOAc complexes of the new bis(imino)acenaphthene(BIAN)-supported N-heterocyclic carbene ligand and the precursor imidazolium salt have been investigated with respect to their antimicrobial activities against Staphylococcus aureus, Bacillus subtilis, Escherichia coli and Psudomonas aeruginosa. [...] Read more.
The AgCl, AgOAc, AuCl, and AuOAc complexes of the new bis(imino)acenaphthene(BIAN)-supported N-heterocyclic carbene ligand and the precursor imidazolium salt have been investigated with respect to their antimicrobial activities against Staphylococcus aureus, Bacillus subtilis, Escherichia coli and Psudomonas aeruginosa. The most active antimicrobial is the precursor imidazolium salt, which has a minimum inhibitory concentration (MIC) value of Full article
Open AccessArticle Identification and Determination of Flavonoids in Astragali Radix by High Performance Liquid Chromatography Coupled with DAD and ESI-MS Detection
Molecules 2011, 16(3), 2293-2303; doi:10.3390/molecules16032293
Received: 10 January 2011 / Revised: 24 February 2011 / Accepted: 4 March 2011 / Published: 9 March 2011
Cited by 6 | PDF Full-text (199 KB)
Abstract
A method for the analysis of flavonoids in Astragali Radix by high-performance liquid chromatography (HPLC) combined with photodiode-array detection (DAD) and an electrospray ionization (ESI) - mass spectrometry (MS) was developed. After the samples were extracted with ethanol, the optimum separation conditions [...] Read more.
A method for the analysis of flavonoids in Astragali Radix by high-performance liquid chromatography (HPLC) combined with photodiode-array detection (DAD) and an electrospray ionization (ESI) - mass spectrometry (MS) was developed. After the samples were extracted with ethanol, the optimum separation conditions for these analytes were achieved using a gradient elution system and a 2.0 × 150 mm Shimadzu VP-ODS column. Eight flavonoids were identified to exist in Astragali Radix based on their characteristic UV data and mass spectra. The concentrations of three major components in this herb—ononin, calycosin and formononetin—were determined by LC/ESI-MS in positive selective ion monitoring (SIM) mode. The calibration curves were linear in the range of 0.9~180.0 μg·mL−1 for ononin, 1.8~360.0 μg·mL−1 for calycosin and 1.4~280 μg·mL−1 for formononetin, respectively. The limits of quantification (LOQ) and detection (LOD) were 0.9 μg· mL−1 and 0.2 μg mL−1 for ononin, 1.8 μg mL−1 and 0.5 μg·mL−1 for calycosin, 1.4 μg mL−1 and 0.5 μg·mL−1 for formononetin, respectively. The standard recoveries were between 95.4~104.7%. The developed method was proven to be useful for the quantitative and qualitative analysis of flavonoid constituents in various resources of Astragali Radix. Full article
(This article belongs to the Section Natural Products)
Open AccessArticle Synthesis and Antimicrobial Evaluation of Some Heterocyclic Chalcone Derivatives
Molecules 2011, 16(3), 2304-2312; doi:10.3390/molecules16032304
Received: 13 December 2010 / Revised: 12 February 2011 / Accepted: 21 February 2011 / Published: 9 March 2011
Cited by 14 | PDF Full-text (228 KB)
Abstract Some new heterocyclic compounds containing isoxazole, pyrazole and oxadiazole ring systems were prepared from various chalcones. The synthesized compounds have been characterized by elemental analysis and spectral methods. These compounds were screened for their antimicrobial activities. Full article
(This article belongs to the Special Issue Cycloaddition Reactions in Organic Synthesis)
Open AccessArticle Effect of Calcinated Oyster Shell Powder on Growth, Yield, Spawn Run, and Primordial Formation of King Oyster Mushroom (Pleurotus Eryngii)
Molecules 2011, 16(3), 2313-2322; doi:10.3390/molecules16032313
Received: 18 January 2011 / Revised: 26 February 2011 / Accepted: 9 March 2011 / Published: 10 March 2011
Cited by 5 | PDF Full-text (438 KB)
Abstract
This study was conducted to evaluate the calcium (Ca) absorption efficacy of king oyster mushroom (Pleurotus eryngii) grown on sawdust medium supplemented with Ca-sources, including oyster shell powder, and to determine the efficacy of oyster shell powder as a calcium [...] Read more.
This study was conducted to evaluate the calcium (Ca) absorption efficacy of king oyster mushroom (Pleurotus eryngii) grown on sawdust medium supplemented with Ca-sources, including oyster shell powder, and to determine the efficacy of oyster shell powder as a calcium supplement on growth, yield, spawn run and primordial formation of P. eryngii. Optimum calcination of oyster shell powder was achieved at the temperature of 620.56 °C. A 1% supplementation of oyster shell powder in sawdust medium did not suppress the mycelial growth of P. eryngii. Also the supplementation of 2% calcinated oyster shell powder to sawdust medium potentially increased the calcium content up to a level of 315.7 ± 15.7 mg/100 g in the fruiting body of P. eryngii, without extension of duration of spawn run and the retardation of the days to primordial formation. These results suggest that the shellfish by-products, including oyster shell powder, can be utilized to develop calcium enriched king oyster mushrooms. Full article
Open AccessArticle An Allelochemical from Myrica gale with Strong Phytotoxic Activity against Highly Invasive Fallopia x bohemica Taxa
Molecules 2011, 16(3), 2323-2333; doi:10.3390/molecules16032323
Received: 31 January 2011 / Revised: 2 March 2011 / Accepted: 9 March 2011 / Published: 10 March 2011
Cited by 10 | PDF Full-text (277 KB)
Abstract
We report the identification of the allelochemical 3-(1-oxo-3-phenylpropyl)-1,1,5-trimethylcyclo-hexane-2,4,6-trione, known as myrigalone A, from the fruits and leaves of Myrica gale. The structure of the compound was confirmed by high-resolution techniques (UV, MS and NMR analysis). The compound is phytotoxic towards classical [...] Read more.
We report the identification of the allelochemical 3-(1-oxo-3-phenylpropyl)-1,1,5-trimethylcyclo-hexane-2,4,6-trione, known as myrigalone A, from the fruits and leaves of Myrica gale. The structure of the compound was confirmed by high-resolution techniques (UV, MS and NMR analysis). The compound is phytotoxic towards classical plant species used for allelochemical assays and also against Fallopia x bohemica, a highly invasive plant. Application of either powdered dry leaves or dry fruits of M. gale also showed in vitro phytotoxic activity. We hypothesize that M. gale could be used as a green allelopathic shield to control Fallopia x bohemica invasion, in addition to its potential use as an environmentally friendly herbicide. Full article
(This article belongs to the Section Natural Products)
Open AccessArticle Antioxidant and Antityrosinase Activities of Various Extracts from the Fruiting Bodies of Lentinus lepideus
Molecules 2011, 16(3), 2334-2347; doi:10.3390/molecules16032334
Received: 14 January 2011 / Revised: 6 March 2011 / Accepted: 9 March 2011 / Published: 10 March 2011
Cited by 15 | PDF Full-text (230 KB)
Abstract
Lentinus lepideus is an edible mushroom currently available in Korea. The acetone, methanol and hot water extracts were prepared and assayed for their antioxidant and antityrosinase inhibitory activities. The hot water extract showed the strongest β-carotene-linoleic acid inhibition compared to the other [...] Read more.
Lentinus lepideus is an edible mushroom currently available in Korea. The acetone, methanol and hot water extracts were prepared and assayed for their antioxidant and antityrosinase inhibitory activities. The hot water extract showed the strongest β-carotene-linoleic acid inhibition compared to the other extracts. At 8 mg/mL, the methanolic extract showed a high reducing power of 1.21. The acetone and methanol extracts were more effective in scavenging DPPH radicals than the hot water extract. The strongest chelating effect was obtained from the methanolic extract. Xanthine oxidase and tyrosinase inhibitory activities of the acetonic, methanol and hot water extracts increased with increasing concentration. Gallic acid, chlorogenic acid, vanillin, naringin, naringenin, formononetin, and biochanin-A were detected in the acetonitrile and hydrochloric acid (5:1) solvent extract. This study suggests that fruiting bodies of L. lepideus can potentially be used as a readily accessible source of natural antioxidants. Full article
Figures

Open AccessArticle A-Type Cranberry Proanthocyanidins Inhibit the RANKL-Dependent Differentiation and Function of Human Osteoclasts
Molecules 2011, 16(3), 2365-2374; doi:10.3390/molecules16032365
Received: 7 February 2011 / Revised: 7 March 2011 / Accepted: 9 March 2011 / Published: 11 March 2011
Cited by 11 | PDF Full-text (1104 KB)
Abstract
This study investigated the effect of A-type cranberry proanthocyanidins (AC-PACs) on osteoclast formation and bone resorption activity. The differentiation of human pre-osteoclastic cells was assessed by tartrate-resistant acid phosphatase (TRAP) staining, while the secretion of interleukin-8 (IL-8) and matrix metalloproteinases (MMPs) was [...] Read more.
This study investigated the effect of A-type cranberry proanthocyanidins (AC-PACs) on osteoclast formation and bone resorption activity. The differentiation of human pre-osteoclastic cells was assessed by tartrate-resistant acid phosphatase (TRAP) staining, while the secretion of interleukin-8 (IL-8) and matrix metalloproteinases (MMPs) was measured by ELISA. Bone resorption activity was investigated by using a human bone plate coupled with an immunoassay that detected the release of collagen helical peptides. AC-PACs up to 100 µg/mL were atoxic for osteoclastic cells. TRAP staining evidenced a dose-dependent inhibition of osteoclastogenesis. More specifically, AC-PACs at 50 µg/mL caused a 95% inhibition of RANKL-dependent osteoclast differentiation. This concentration of AC-PACs also significantly increased the secretion of IL-8 (6-fold) and inhibited the secretion of both MMP-2 and MMP-9. Lastly, AC-PACs (10, 25, 50 and 100 µg/ml) affected bone degradation mediated by mature osteoclasts by significantly decreasing the release of collagen helical peptides. This study suggests that AC-PACs can interfere with osteoclastic cell maturation and physiology as well as prevent bone resorption. These compounds may be considered as therapeutic agents for the prevention and treatment of periodontitis. Full article
(This article belongs to the Special Issue Tannins)
Figures

Open AccessArticle Cranberry Proanthocyanidins Mediate Growth Arrest of Lung Cancer Cells through Modulation of Gene Expression and Rapid Induction of Apoptosis
Molecules 2011, 16(3), 2375-2390; doi:10.3390/molecules16032375
Received: 28 January 2011 / Revised: 8 March 2011 / Accepted: 10 March 2011 / Published: 11 March 2011
Cited by 20 | PDF Full-text (442 KB)
Abstract
Cranberries are rich in bioactive constituents purported to enhance immune function, improve urinary tract health, reduce cardiovascular disease and more recently, inhibit cancer in preclinical models. However, identification of the cranberry constituents with the strongest cancer inhibitory potential and the mechanism associated [...] Read more.
Cranberries are rich in bioactive constituents purported to enhance immune function, improve urinary tract health, reduce cardiovascular disease and more recently, inhibit cancer in preclinical models. However, identification of the cranberry constituents with the strongest cancer inhibitory potential and the mechanism associated with cancer inhibition by cranberries remains to be elucidated. This study investigated the ability of a proanthocyanidin rich cranberry fraction (PAC) to alter gene expression, induce apoptosis and impact the cell cycle machinery of human NCI-H460 lung cancer cells. Lung cancer is the leading cause of cancer-related deaths in the United States and five year survival rates remain poor at 16%. Thus, assessing potential inhibitors of lung cancer-linked signaling pathways is an active area of investigation. Full article
(This article belongs to the Special Issue Tannins)
Open AccessArticle Investigating Spectrum of Biological Activity of 4- and 5-Chloro-2-hydroxy-N-[2-(arylamino)-1-alkyl-2-oxoethyl]benzamides
Molecules 2011, 16(3), 2414-2430; doi:10.3390/molecules16032414
Received: 11 January 2011 / Revised: 7 March 2011 / Accepted: 11 March 2011 / Published: 14 March 2011
Cited by 18 | PDF Full-text (312 KB)
Abstract
In this study, a series of twenty-two 5-chloro-2-hydroxy-N-[2-(arylamino)-1-alkyl-2-oxoethyl]benzamides and ten 4-chloro-2-hydroxy-N-[2-(arylamino)-1-alkyl-2-oxoethyl]benzamides is described. The compounds were analyzed using RP-HPLC to determine lipophilicity. Primary in vitro screening of the synthesized compounds was performed against mycobacterial, bacterial and fungal strains. [...] Read more.
In this study, a series of twenty-two 5-chloro-2-hydroxy-N-[2-(arylamino)-1-alkyl-2-oxoethyl]benzamides and ten 4-chloro-2-hydroxy-N-[2-(arylamino)-1-alkyl-2-oxoethyl]benzamides is described. The compounds were analyzed using RP-HPLC to determine lipophilicity. Primary in vitro screening of the synthesized compounds was performed against mycobacterial, bacterial and fungal strains. They were also evaluated for their activity related to the inhibition of photosynthetic electron transport (PET) in spinach (Spinacia oleracea L.) chloroplasts. The compounds showed biological activity comparable with or higher than the standards isoniazid, fluconazole, penicillin G or ciprofloxacin. For all the compounds, the relationships between the lipophilicity and the chemical structure of the studied compounds as well as their structure-activity relationships are discussed. Full article
Open AccessArticle Bioflocculant Production by Virgibacillus sp. Rob Isolated from the Bottom Sediment of Algoa Bay in the Eastern Cape, South Africa
Molecules 2011, 16(3), 2431-2442; doi:10.3390/molecules16032431
Received: 21 December 2011 / Revised: 10 March 2011 / Accepted: 11 March 2011 / Published: 14 March 2011
Cited by 36 | PDF Full-text (161 KB)
Abstract
A bioflocculant-producing marine bacterium previously isolated from marine sediment of Algoa Bay was screened for flocculant production. Comparative analysis of 16S rDNA sequence identified the isolate to have 99% similarity to Virgibacillus sp. XQ-1 and it was deposited in the GenBank as [...] Read more.
A bioflocculant-producing marine bacterium previously isolated from marine sediment of Algoa Bay was screened for flocculant production. Comparative analysis of 16S rDNA sequence identified the isolate to have 99% similarity to Virgibacillus sp. XQ-1 and it was deposited in the GenBank as Virgibacillus sp. Rob with accession number HQ537127. The bacterium produced biflocculants optimally in glucose (70.4%) and peptone (70.4%) as sole sources of carbon and nitrogen, alkaline pH (12) (74%); and the presence of Fe2+ (74%). Chemical analysis of the bioflocculant revealed it to be a polysaccharide. Full article
Open AccessArticle Role of the Morphology and Polyphosphate in Trichoderma harzianum Related to Cadmium Removal
Molecules 2011, 16(3), 2486-2500; doi:10.3390/molecules16032486
Received: 14 January 2011 / Revised: 2 March 2011 / Accepted: 4 March 2011 / Published: 15 March 2011
Cited by 12 | PDF Full-text (2632 KB)
Abstract
This study concerns the metabolism of polyphosphate in Trichoderma harzianum, a biocontrol agent with innate resistance against most chemicals used in agriculture, including metals, when grown in the presence of different concentrations of cadmium. The biomass production was affected by the [...] Read more.
This study concerns the metabolism of polyphosphate in Trichoderma harzianum, a biocontrol agent with innate resistance against most chemicals used in agriculture, including metals, when grown in the presence of different concentrations of cadmium. The biomass production was affected by the concentration of metal used. Control cultures were able to accumulate polyphosphate under the conditions used. Moreover, the presence of cadmium induced a reduction in polyphosphate content related to the concentration used. The morphological/ultrastructural aspects were characterized by using optical and scanning electron microscopy, and were affected by the heavy metal presence and concentration. The efficiency of cadmium removal revealed the potential of the microorganism for use in remediation. The data indicate the potential for polyphosphate accumulation by the fungus, as well as its degradation related to tolerance/survival in the presence of cadmium ions. Full article
(This article belongs to the Section Natural Products)
Open AccessArticle Fungicidal Properties of the Essential Oil of Hesperozygis marifolia on Aspergillus flavus Link
Molecules 2011, 16(3), 2501-2506; doi:10.3390/molecules16032501
Received: 24 February 2011 / Revised: 5 March 2011 / Accepted: 11 March 2011 / Published: 15 March 2011
Cited by 3 | PDF Full-text (109 KB)
Abstract
The chemical composition of the essential oil from Hesperozygis marifolia was analyzed by gas chromatography-mass spectrometry (GC-MS), and fourteen compounds were identified. (R)-pulegone (40.75%), isomenthone (30.34%) and menthone (4.46%) were found to be the main components of the oil. The [...] Read more.
The chemical composition of the essential oil from Hesperozygis marifolia was analyzed by gas chromatography-mass spectrometry (GC-MS), and fourteen compounds were identified. (R)-pulegone (40.75%), isomenthone (30.34%) and menthone (4.46%) were found to be the main components of the oil. The essential oil at a concentration of 2.0 mg/mL and (R)-pulegone at concentration of 0.8 mg/mL completely inhibited the growth of Aspergillus flavus Link. The fungicidal effects of this essential oil warrant further research into its potential for commercial use. Full article
Figures

Open AccessArticle Screening of Natural Organic Volatiles from Prunus mahaleb L. Honey: Coumarin and Vomifoliol as Nonspecific Biomarkers
Molecules 2011, 16(3), 2507-2518; doi:10.3390/molecules16032507
Received: 18 February 2011 / Revised: 15 March 2011 / Accepted: 15 March 2011 / Published: 16 March 2011
Cited by 16 | PDF Full-text (174 KB)
Abstract
Headspace solid-phase microextraction (HS-SPME; PDMS/DVB fibre) and ultrasonic solvent extraction (USE; solvent A: pentane and diethyl ether (1:2 v/v), solvent B: dichloromethane) followed by gas chromatography and mass spectrometry (GC, GC-MS) were used for the analysis of Prunus mahaleb L. honey samples. [...] Read more.
Headspace solid-phase microextraction (HS-SPME; PDMS/DVB fibre) and ultrasonic solvent extraction (USE; solvent A: pentane and diethyl ether (1:2 v/v), solvent B: dichloromethane) followed by gas chromatography and mass spectrometry (GC, GC-MS) were used for the analysis of Prunus mahaleb L. honey samples. Screening was focused toward chemical composition of natural organic volatiles to determine if it is useful as a method of determining honey-sourcing. A total of 34 compounds were identified in the headspace and 49 in the extracts that included terpenes, norisoprenoids and benzene derivatives, followed by minor percentages of aliphatic compounds and furan derivatives. High vomifoliol percentages (10.7%–24.2%) in both extracts (dominant in solvent B) and coumarin (0.3%–2.4%) from the extracts (more abundant in solvent A) and headspace (0.9%–1.8%) were considered characteristic for P. mahaleb honey and highlighted as potential nonspecific biomarkers of the honey’s botanical origin. In addition, comparison with P. mahaleb flowers, leaves, bark and wood volatiles from our previous research revealed common compounds among norisoprenoids and benzene derivatives. Full article
Open AccessArticle Synthesis and Biological Evaluation of Novel Acenaphthene Derivatives as Potential Antitumor Agents
Molecules 2011, 16(3), 2519-2526; doi:10.3390/molecules16032519
Received: 15 February 2011 / Revised: 2 March 2011 / Accepted: 10 March 2011 / Published: 17 March 2011
Cited by 4 | PDF Full-text (187 KB)
Abstract
Twelve novel acenaphthene derivatives have been synthesized. The structures of all compounds were confirmed by 1H-NMR, MS and elemental analysis. Their antitumor activities were evaluated in six human solid tumor cell lines, namely non-small cell lung cancer (H460), human colon adenocarcinoma [...] Read more.
Twelve novel acenaphthene derivatives have been synthesized. The structures of all compounds were confirmed by 1H-NMR, MS and elemental analysis. Their antitumor activities were evaluated in six human solid tumor cell lines, namely non-small cell lung cancer (H460), human colon adenocarcinoma (SW480), human breast cancer cell (MDA-MB-468 and SKRB-3), human melanoma cell (A375) and human pancreatic cancer (BxPC-3) . Among them, compound 3c shows the best antitumor activity against SKRB-3 cell line, as high as the positive control adriamycin. Full article
(This article belongs to the Section Medicinal Chemistry)
Open AccessArticle Antioxidant Bibenzyl Derivatives from Notholaena nivea Desv.
Molecules 2011, 16(3), 2527-2541; doi:10.3390/molecules16032527
Received: 24 January 2011 / Revised: 11 March 2011 / Accepted: 15 March 2011 / Published: 17 March 2011
Cited by 6 | PDF Full-text (157 KB)
Abstract
Four new bibenzyl derivatives were isolated, together with other known bibenzyls, by bioassay-guided fractionation of a CHCl3-MeOH extract of Notholaena nivea Desv. (Pteridaceae) aerial parts. The structures were elucidated by NMR, ESIMS and other spectral analyses. Their antioxidative effects towards [...] Read more.
Four new bibenzyl derivatives were isolated, together with other known bibenzyls, by bioassay-guided fractionation of a CHCl3-MeOH extract of Notholaena nivea Desv. (Pteridaceae) aerial parts. The structures were elucidated by NMR, ESIMS and other spectral analyses. Their antioxidative effects towards superoxide, lipidic peroxidation and the 2,2'-azino-bis-3-ethilbenzothiazoline-6-sulfonic acid (ABTS) radical were assayed. Results showed that the compound 3,12-dihydroxy-5-methoxybibenzyl (6) is the most active compound in the ABTS free-radical scavenging test, while in the coupled oxidation of β-carotene and linoleic acid assay the compound 5,12-dihydroxy-3-methoxydibenzyl-6-carboxylic acid (1) exerted the highest activity after 1h. A superoxide anion enzymatic test was also carried out and the results were confirmed by an inhibition of xanthine oxidase activity assay. The putative protective role played by compounds 1 and 6 on the injurious effects of reactive oxygen metabolites on the intestinal epithelium, using a Caco-2 human cell line, was investigated. H2O2-induced alterations were prevented by preincubating the cells with compounds 1 and 6. Full article
(This article belongs to the Section Natural Products)
Open AccessArticle The Effect of Lycium Barbarum Polysaccharide on Alcohol-Induced Oxidative Stress in Rats
Molecules 2011, 16(3), 2542-2550; doi:10.3390/molecules16032542
Received: 9 February 2011 / Revised: 10 March 2011 / Accepted: 14 March 2011 / Published: 17 March 2011
Cited by 36 | PDF Full-text (454 KB)
Abstract
The aim of this study was to investigate the effects of Lycium barbarum Polysaccharide (LBP) on alcohol-induced liver damage in rats. A total of 36 rats were divided into control, ethanol and ethanol + LBP groups. Rats in the ethanol group were [...] Read more.
The aim of this study was to investigate the effects of Lycium barbarum Polysaccharide (LBP) on alcohol-induced liver damage in rats. A total of 36 rats were divided into control, ethanol and ethanol + LBP groups. Rats in the ethanol group were fed 7 g ethanol/kg body weight by gastric infusion, three times a day, for 30 consecutive days, while rats in the control group received the same volume of physiological saline instead of ethanol, and rats in ethanol + LBP group were fed both ethanol (7 g/kg body weight) and LBP (300 mg/Kg body weight/day). Alcoholic liver injury was examined by serum ALT and AST activities, alcoholic fatty liver was assessed by lipid levels, and oxidative stress was evaluated by SOD, CAT, GSH-Px, GSH and MDA assays. In the ethanol group, a significant elevation of enzymes and lipid in serum, increased MDA level and depletion of SOD, CAT, GSH-Px and GSH in liver were observed. LBP administration significantly ameliorated liver injury, prevented the progression of alcohol-induced fatty liver, and improved the antioxidant functions when compared with the ethanol group. Histopathological examination of rat liver revealed that LBP administration protected liver cells from the damage induced by ethanol. The results suggest that LBP is a promising agent to protect the liver from hepatotoxicity and fatty liver induced by ethanol intake. Full article
Open AccessCommunication LC/MS Guided Isolation of Alkaloids from Lotus Leaves by pH-Zone-Refining Counter-Current Chromatography
Molecules 2011, 16(3), 2551-2560; doi:10.3390/molecules16032551
Received: 14 February 2011 / Revised: 10 March 2011 / Accepted: 14 March 2011 / Published: 18 March 2011
Cited by 5 | PDF Full-text (345 KB)
Abstract
The traditional methods used in natural product separation primarily target the major components and the minor components may thus be lost during the separation procedure. Consequently, it’s necessary to develop efficient methods for the preparative separation and purification of relatively minor bioactive [...] Read more.
The traditional methods used in natural product separation primarily target the major components and the minor components may thus be lost during the separation procedure. Consequently, it’s necessary to develop efficient methods for the preparative separation and purification of relatively minor bioactive components. In this paper, a LC/MS method was applied to guide the separation of crude extract of lotus (Nelumbo nucifera Gaertn.) leaves whereby a minor component was identified in the LC/MS analysis. Afterwards, an optimized pH-zone-refining CCC method was performed to isolate this product, identified as N-demethylarmepavine. The separation procedure was carried out with a biphasic solvent system composed of hexane-ethyl acetate-methyl alcohol-water (1:6:1:6, v/v) with triethylamine (10 mM) added to the upper organic phase as a retainer and hydrochloric acid (5 mM) to the aqueous mobile phase eluent. Two structurally similar compounds – nuciferine and roemerine – were also obtained from the crude lotus leaves extract. In total 500 mg of crude extract furnished 7.4 mg of N-demethylarmepavine, 45.3 mg of nuciferine and 26.6 mg of roemerine with purities of 90%, 92% and 96%, respectively. Their structures were further identified by HPLC/ESI-MSn, FTICR/MS and the comparison with reference compounds. Full article
Open AccessArticle Purification, Biochemical Characterization, and Bioactive Properties of a Lectin Purified from the Seeds of White Tepary Bean (Phaseolus Acutifolius Variety Latifolius)
Molecules 2011, 16(3), 2561-2582; doi:10.3390/molecules16032561
Received: 19 January 2011 / Revised: 17 March 2011 / Accepted: 17 March 2011 / Published: 21 March 2011
Cited by 4 | PDF Full-text (625 KB)
Abstract
The present work shows the characterization of Phaseolus acutifolius variety latifolius, on which little research has been published, and provides detailed information on the corresponding lectin. This protein was purified from a semi-domesticated line of white tepary beans from Sonora, Mexico, by [...] Read more.
The present work shows the characterization of Phaseolus acutifolius variety latifolius, on which little research has been published, and provides detailed information on the corresponding lectin. This protein was purified from a semi-domesticated line of white tepary beans from Sonora, Mexico, by precipitation of the aqueous extract with ammonium sulfate, followed by affinity chromatography on an immobilized fetuin matrix. MALDI TOF analysis of Phaseolus acutifolius agglutinin (PAA) showed that this lectin is composed of monomers with molecular weights ranging between 28 and 31 kDa. At high salt concentrations, PAA forms a dimer of 63 kDa, but at low salt concentrations, the subunits form a tetramer. Analysis of PAA on 2D-PAGE showed that there are mainly three types of subunits with isoelectric points of 4.2, 4.4, and 4.5. The partial sequence obtained by LC/MS/MS of tryptic fragments from the PAA subunits showed 90–100% identity with subunits from genus Phaseolus lectins in previous reports. The tepary bean lectin showed lower hemagglutination activity than Phaseolus vulgaris hemagglutinin (PHA-E) toward trypsinized human A and O type erythrocytes. The hemagglutination activity was inhibited by N-glycans from glycoproteins. Affinity chromatography with the immobilized PAA showed a high affinity to glycopeptides from thyroglobulin, which also has N-glycans with a high content of N-acetylglucosamine. PAA showed less mitogenic activity toward human lymphocytes than PHA-L and Con A. The cytotoxicity of PAA was determined by employing three clones of the 3T3 cell line, demonstrating variability among the clones as follows: T4 (DI50 51.5 µg/mL); J20 (DI50 275 µg/mL), and N5 (DI50 72.5 µg/mL). Full article
(This article belongs to the Section Molecular Diversity)
Open AccessArticle Panduratin A Inhibits the Growth of A549 Cells through Induction of Apoptosis and Inhibition of NF-KappaB Translocation
Molecules 2011, 16(3), 2583-2598; doi:10.3390/molecules16032583
Received: 23 February 2011 / Revised: 3 March 2011 / Accepted: 11 March 2011 / Published: 21 March 2011
Cited by 29 | PDF Full-text (1490 KB)
Abstract
In the present study we investigated the effects of panduratin A, isolated from Boesenbergia rotunda, on proliferation and apoptosis in A549 human non-small cell lung cancer cells. Cell proliferation and induction of apoptosis was determined by the real-time cellular analyzer (RTCA), [...] Read more.
In the present study we investigated the effects of panduratin A, isolated from Boesenbergia rotunda, on proliferation and apoptosis in A549 human non-small cell lung cancer cells. Cell proliferation and induction of apoptosis was determined by the real-time cellular analyzer (RTCA), MTT assay and High Content Screening (HCS). The RTCA assay indicated that panduratin A exhibited cytotoxicity, with an IC50 value of 4.4 µg/mL (10.8 µM). Panduratin A arrested cancer cells labeled with bromodeoxyuridine (BrdU) and phospho-Histone H3 in the mitotic phase. The cytotoxic effects of panduratin A were found to be accompanied by a dose-dependent induction of apoptosis, as assessed by DNA condensation, nuclear morphology and intensity, cell permeability, mitochondrial mass/ potential, F-actin and cytochrome c. In addition, treatment with an apoptosis-inducing concentration of panduratin A resulted in significant inhibition of Nuclear Factor-kappa Beta (NF-κB) translocation from cytoplasm to nuclei activated by tumor necrosis factor-alpha (TNF-α), as illustrated by the HCS assay. Our study provides evidence for cell growth inhibition and induction of apoptosis by panduratin A in the A549 cell line, suggesting its therapeutic potential as an NF-κB inhibitor. Full article
(This article belongs to the Section Natural Products)
Figures

Open AccessArticle Studies on the Genetic Variation of the Green Unicellular Alga Haematococcus pluvialis (Chlorophyceae) Obtained from Different Geographical Locations Using ISSR and RAPD Molecular Marker
Molecules 2011, 16(3), 2599-2608; doi:10.3390/molecules16032599
Received: 24 January 2011 / Revised: 1 March 2011 / Accepted: 4 March 2011 / Published: 22 March 2011
Cited by 7 | PDF Full-text (353 KB) | Supplementary Files
Abstract
Haematococcus pluvialis (Flotow) is a unicellular green alga, which is considered to be the best astaxanthin-producing organism. Molecular markers are suitable tools for the purpose of finding out genetic variations in organisms; however there have been no studies conducted on ISSR or [...] Read more.
Haematococcus pluvialis (Flotow) is a unicellular green alga, which is considered to be the best astaxanthin-producing organism. Molecular markers are suitable tools for the purpose of finding out genetic variations in organisms; however there have been no studies conducted on ISSR or RAPD molecular markers for this organism. The DNA of 10 different strains of H. pluvialis (four strains from Iran, two strains from Finland, one strain from Switzerland and three strains from the USA) was extracted. A genetic similarity study was carried out using 14 ISSR and 12 RAPD primers. Moreover, the molecular weights of the bands produced ranged from 0.14 to 3.4 Kb. The PCA and dendrogram clustered the H. pluvialis strains into various groups according to their geographical origin. The lowest genetic similarity was between the Iran2 and USA2 strains (0.08) and the highest genetic similarity was between Finland1 and Finland2 (0.64). The maximum numbers of bands produced by the ISSR and RAPD primers were 35 and 6 bands, respectively. The results showed that ISSR and RAPD markers are useful for genetic diversity studies of Haematococcus as they showed geographical discrimination. Full article
(This article belongs to the Section Molecular Diversity)
Open AccessArticle Chemical Composition and In Vitro Activity of Plant Extracts from Ferula communis and Dittrichia viscosa against Postharvest Fungi
Molecules 2011, 16(3), 2609-2625; doi:10.3390/molecules16032609
Received: 1 March 2011 / Revised: 15 March 2011 / Accepted: 18 March 2011 / Published: 22 March 2011
Cited by 12 | PDF Full-text (913 KB) | Supplementary Files
Abstract
F. communis and D. viscosa are perennial Mediterranean weeds that have been used for different therapeutic purposes in traditional pharmacopeia. Plant extracts were obtained from air dried D. viscosa young shoots (DvA) and F. communis aerial part (FcA) and roots (FcR) with [...] Read more.
F. communis and D. viscosa are perennial Mediterranean weeds that have been used for different therapeutic purposes in traditional pharmacopeia. Plant extracts were obtained from air dried D. viscosa young shoots (DvA) and F. communis aerial part (FcA) and roots (FcR) with n-hexane. The chemical compositions of the extracts were analyzed by HPLC-DAD, LC-MS (ESI) and LC-Q-TOF techniques. Two sesquiterpene lactones (inuviscolide, tomentosin) and three sesquiterpene acids (costic acid, hydroxycostic acid, ilicic acid) were identified from the D. viscosa extract, while in F. communis extracts three daucane sesquiterpenes (acetoxyferutinin, oxojaeskeanadioyl anisate, fertidin) and one coumarin (ferulenol) derivates were found. Biological activities of plant extracts were studied in in vitro experiments on the colonies and conidia of Botryotinia fuckeliana, Penicillium digitatum, P. expansum, Monilinia laxa, M. fructigena and Aspergillus spp. Extracts showed varying degree of antifungal activities on colony growth and conidia germination. The extract from FcA showed the least effect, while DvA extract had the strongest fungitoxic effects. FcR extract presented a fungitoxic effect on the colony growth, but it was not able to inhibit the conidia germination. These distinctions can be attributed to the differences in chemical composition of plant extracts. Full article
(This article belongs to the Section Natural Products)
Open AccessArticle Synthesis and In Vitro Antibacterial Activity of 7-(3-Amino-6,7-dihydro-2-methyl-2H-pyrazolo[4,3-c] Pyridin-5(4H)-yl)fluoroquinolone Derivatives
Molecules 2011, 16(3), 2626-2635; doi:10.3390/molecules16032626
Received: 31 December 2010 / Revised: 16 March 2011 / Accepted: 18 March 2011 / Published: 22 March 2011
Cited by 4 | PDF Full-text (189 KB)
Abstract
A series of novel 7-(3-amino-6,7-dihydro-2-methyl-2H-pyrazolo[4,3-c]pyridin- 5(4H)-yl)fluoroquinolone derivatives were designed, synthesized and characterized by 1H-NMR, MS and HRMS. These fluoroquinolones were evaluated for their in vitro antibacterial activity against representative Gram-positive and Gram-negative strains. Results reveal that most [...] Read more.
A series of novel 7-(3-amino-6,7-dihydro-2-methyl-2H-pyrazolo[4,3-c]pyridin- 5(4H)-yl)fluoroquinolone derivatives were designed, synthesized and characterized by 1H-NMR, MS and HRMS. These fluoroquinolones were evaluated for their in vitro antibacterial activity against representative Gram-positive and Gram-negative strains. Results reveal that most of the target compounds exhibit good growth inhibitory potency against methicillin-resistant Staphylococcus epidermidis (MRSE) (MIC: 0.25–4 μg/mL) and Streptococcus pneumoniae (MIC: 0.25–1 μg/mL). In addition, compound 8f is 8–128 fold more potent than the reference drugs gemifloxacin (GM), moxifloxacin (MX), ciprofloxacin (CP) and levofloxacin (LV) against methicillin-resistant Staphylococcus aureus 10-05 and Streptococcus hemolyticus 1002 and 2–64 fold more active against methicillin-sensitive Staphylococcus aureus 10-03 and 10-04. Full article
Open AccessArticle Immunosuppressive Activity of 8-Gingerol on Immune Responses in Mice
Molecules 2011, 16(3), 2636-2645; doi:10.3390/molecules16032636
Received: 14 January 2011 / Revised: 12 March 2011 / Accepted: 16 March 2011 / Published: 22 March 2011
Cited by 14 | PDF Full-text (209 KB)
Abstract
8-Gingerol is one of the principal components of ginger, which is widely used in China and elsewhere as a food, spice and herb. It shows immunosuppressive activity on the immune responses to ovalbumin (OVA) in mice. In the present study, we found that 8-gingerol suppressed lipopolysaccharide (LPS) and concanavalin A (ConA)-stimulated splenocyte proliferation in vitro. In vivo, 8-gingerol not only significantly suppressed Con A-, LPS- and OVA-induced splenocyte proliferation (P < 0.05) but also decreased the percentage of CD19+ B cells and CD3+ T cell (P < 0.05) at high doses (50, 100 mg/kg). Moreover, OVA-specific IgG, IgG1 and IgG2b levels in OVA-immunized mice were reduced by 8-gingerol at doses of 50, 100 mg/kg. These results suggest that 8-gingerol could suppress humoral and cellular immune responses in mice. The mechanism might be related to direct inhibition of sensitized T and B lymphocytes. Full article
Open AccessArticle Inter-Population Variability of Terpenoid Composition in Leaves of Pistacia lentiscus L. from Algeria: A Chemoecological Approach
Molecules 2011, 16(3), 2646-2657; doi:10.3390/molecules16032646
Received: 22 February 2011 / Revised: 17 March 2011 / Accepted: 18 March 2011 / Published: 22 March 2011
Cited by 6 | PDF Full-text (178 KB)
Abstract
Three different altitudes were selected to study the variability of terpenoid composition from leaves of female plants of Pistacia lentiscus L. throughout the elevation gradient. GC-MS analyses showed that terpenoid contents change with altitude. Forty nine compounds were identified with a high [...] Read more.
Three different altitudes were selected to study the variability of terpenoid composition from leaves of female plants of Pistacia lentiscus L. throughout the elevation gradient. GC-MS analyses showed that terpenoid contents change with altitude. Forty nine compounds were identified with a high interpopulation variability for low- and midaltitude sites that also exhibited the same major components when data were expressed on dry weight basis. However, Two-Way-ANOVA followed by Tukey’s post hoc test showed that monoterpene hydrocarbons increased with elevation, giving values of 21.7, 37.5 and 221.5 µg g−1 dw for low- mid- and highlands, respectively. On the other hand, applying P.C.A. with data expressed in percentage of the chromatogram of the volatile extract led to the identification of three chemotypes associated with altitudinal levels. In highlands (Group I), the major compounds were b-caryophyllene (12%), δ-cadinene (9.3%) and a-pinene (6.3%) while in midlands (Group II), b-caryophyllene (11.5%), δ-cadinene (8.6%) and caryophyllene oxide (6.8%) were the main components. In lowlands (Group III) δ-cadinene (10.9%), cubebol (10.5%) and β-bisabolene (7.7%) were chiefly present. Hence, the involvement of genetic factors, temperature and drought in the chemical polymorphism of P. lentiscus associated with elevation is discussed in this report. Full article
Figures

Open AccessArticle Investigation of Solvolysis Kinetics of New Synthesized Fluocinolone Acetonide C-21 Esters—An In Vitro Model for Prodrug Activation
Molecules 2011, 16(3), 2658-2671; doi:10.3390/molecules16032658
Received: 18 January 2011 / Revised: 16 March 2011 / Accepted: 21 March 2011 / Published: 23 March 2011
Cited by 6 | PDF Full-text (370 KB)
Abstract
In this study the solvolysis of newly synthesized fluocinolone acetonide C-21 esters was analysed in comparison with fluocinonide during a 24-hour period of time. The solvolysis was performed in an ethanol-water (90:10 v/v) mixture using the excess of NaHCO3. The [...] Read more.
In this study the solvolysis of newly synthesized fluocinolone acetonide C-21 esters was analysed in comparison with fluocinonide during a 24-hour period of time. The solvolysis was performed in an ethanol-water (90:10 v/v) mixture using the excess of NaHCO3. The solvolytic mixtures of each investigated ester have been assayed by a RP-HPLC method using isocratic elution with methanol-water (75:25 v/v); flow rate 1 mL/min; detection at 238 nm; temperature 25 °C. Solvolytic rate constants were calculated from the obtained data. Geometry optimizations and charges calculations were carried out by Gaussian W03 software. A good correlation (R = 0.9924) was obtained between solvolytic rate constants and the polarity of the C-O2 bond of those esters. The established relation between solvolytic rate constant (K) and lipophilicity (cLogP) with experimental anti-inflammatory activity could be indicative for topical corticosteroid prodrug activation. Full article
(This article belongs to the Special Issue Prodrugs)
Figures

Open AccessArticle Oxidative Decarboxylation of Levulinic Acid by Silver(I)/Persulfate
Molecules 2011, 16(3), 2714-2725; doi:10.3390/molecules16032714
Received: 3 December 2010 / Revised: 11 March 2011 / Accepted: 22 March 2011 / Published: 23 March 2011
Cited by 13 | PDF Full-text (294 KB)
Abstract
The oxidative decarboxylation of levulinic acid (LA) by silver(I)/persulfate [Ag(I)/S2O82−] has been investigated in this paper. The effects of buffer solution, initial pH value, time and temperature and dosages of Ag(I)/S2O82− on the [...] Read more.
The oxidative decarboxylation of levulinic acid (LA) by silver(I)/persulfate [Ag(I)/S2O82−] has been investigated in this paper. The effects of buffer solution, initial pH value, time and temperature and dosages of Ag(I)/S2O82− on the decarboxylation of LA were examined in batch experiments and a reaction scheme was proposed on basis of the reaction process. The experimental results showed that a solution of NaOH-KH2PO4 was comparatively suitable for the LA decarboxylation reaction by silver(I)/persulfate. Under optimum conditions (temperature 160 °C, pH 5.0, and time 0.5 h), the rate of LA conversion in NaOH-KH2PO4 solutions with an initial concentration of 0.01 mol LA reached 70.2%, 2-butanone (methyl ethyl ketone) was the single product in the gas phase and the resulted molar yield reached 44.2%. Full article

Review

Jump to: Research

Open AccessReview Chemical Arsenal for the Study of O-GlcNAc
Molecules 2011, 16(3), 1987-2022; doi:10.3390/molecules16031987
Received: 27 December 2010 / Revised: 3 February 2011 / Accepted: 15 February 2011 / Published: 28 February 2011
Cited by 13 | PDF Full-text (897 KB)
Abstract
The concepts of both protein glycosylation and cellular signaling have been influenced by O-linked-β-N-acetylglucosamine (O-GlcNAc) modification (O-GlcNAcylation) on the hydroxyl group of serine or threonine residues. Unlike conventional protein glycosylation, O-GlcNAcylation is localized in the nucleocytoplasm [...] Read more.
The concepts of both protein glycosylation and cellular signaling have been influenced by O-linked-β-N-acetylglucosamine (O-GlcNAc) modification (O-GlcNAcylation) on the hydroxyl group of serine or threonine residues. Unlike conventional protein glycosylation, O-GlcNAcylation is localized in the nucleocytoplasm and its cycling is a dynamic process that operates in a highly regulated manner in response to various cellular stimuli. These characteristics render O-GlcNAcylation similar to phosphorylation, which has long been considered a major regulatory mechanism in cellular processes. Various efficient chemical approaches and novel mass spectrometric (MS) techniques have uncovered numerous O-GlcNAcylated proteins that are involved in the regulation of many important cellular events. These discoveries imply that O-GlcNAcylation is another major regulator of cellular signaling. However, in contrast to phosphorylation, which is regulated by hundreds of kinases and phosphatases, dynamic O-GlcNAc cycling is catalyzed by only two enzymes: uridine diphospho-N-acetyl-glucosamine:polypeptide β-N-acetylglucosaminyl transferase (OGT) and β-D-N-acetylglucosaminidase (OGA). Many useful chemical tools have recently been used to greatly expand our understanding of the extensive crosstalk between O-GlcNAcylation and phosphorylation and hence of cellular signaling. This review article describes the various useful chemical tools that have been developed and discusses the considerable advances made in the O-GlcNAc field. Full article
(This article belongs to the Special Issue Glycosides)
Open AccessReview Antioxidant Therapy as a Potential Approach to Severe Influenza-Associated Complications
Molecules 2011, 16(3), 2032-2052; doi:10.3390/molecules16032032
Received: 10 February 2011 / Revised: 23 February 2011 / Accepted: 25 February 2011 / Published: 28 February 2011
Cited by 23 | PDF Full-text (275 KB)
Abstract
With the appearance of the novel influenza A (H1N1) virus 2009 strain we have experienced a new influenza pandemic and many patients have died from severe complications associated with this pandemic despite receiving intensive care. This suggests that a definitive medical treatment [...] Read more.
With the appearance of the novel influenza A (H1N1) virus 2009 strain we have experienced a new influenza pandemic and many patients have died from severe complications associated with this pandemic despite receiving intensive care. This suggests that a definitive medical treatment for severe influenza-associated complications has not yet been established. Many studies have shown that superoxide anion produced by macrophages infiltrated into the virus-infected organs is implicated in the development of severe influenza-associated complications. Selected antioxidants, such as pyrrolidine dithiocabamate, N-acetyl-L-cysteine, glutathione, nordihydroguaiaretic acid, thujaplicin, resveratrol, (+)-vitisin A, ambroxol, ascorbic acid, 5,7,4-trihydroxy-8-methoxyflavone, catechins, quercetin 3-rhamnoside, iso- quercetin and oligonol, inhibit the proliferation of influenza virus and scavenge superoxide anion. The combination of antioxidants with antiviral drugs synergistically reduces the lethal effects of influenza virus infections. These results suggest that an agent with antiviral and antioxidant activities could be a drug of choice for the treatment of patients with severe influenza-associated complications. This review article updates knowledge of antioxidant therapy as a potential approach to severe influenza-associated complications. Full article
(This article belongs to the Special Issue Antioxidants)
Open AccessReview Positive Allosteric Modulators of Type 5 Metabotropic Glutamate Receptors (mGluR5) and Their Therapeutic Potential for the Treatment of CNS Disorders
Molecules 2011, 16(3), 2097-2106; doi:10.3390/molecules16032097
Received: 6 January 2011 / Revised: 8 February 2011 / Accepted: 28 February 2011 / Published: 2 March 2011
Cited by 40 | PDF Full-text (122 KB)
Abstract
Studies utilizing selective pharmacological antagonists or targeted gene deletion have demonstrated thattype 5 metabotropic glutamate receptors (mGluR5) are critical mediators and potential therapeutic targets for the treatment of numerous disorders of the central nervous system (CNS), including depression, anxiety, drug addiction, chronic [...] Read more.
Studies utilizing selective pharmacological antagonists or targeted gene deletion have demonstrated thattype 5 metabotropic glutamate receptors (mGluR5) are critical mediators and potential therapeutic targets for the treatment of numerous disorders of the central nervous system (CNS), including depression, anxiety, drug addiction, chronic pain, Fragile X syndrome, Parkinson’s disease, and gastroesophageal reflux disease. However, in recent years, the development of positive allosteric modulators (PAMs) of the mGluR5 receptor have revealed that allosteric activation of this receptor may also be of potential therapeutic benefit for the treatment of other CNS disorders, including schizophrenia, cognitive deficits associated with chronic drug use, and deficits in extinction learning. Here we summarize the discovery and characterization of various mGluR5 PAMs, with an emphasis on those that are systemically active. We will also review animal studies showing that these molecules have potential efficacy as novel antipsychotic agents. Finally, we will summarize findings that suggest that mGluR5 PAMs have pro-cognitive effects such as the ability toenhance synaptic plasticity, improve performance in various learning and memory tasks, including extinction of drug-seeking behavior, and reverse cognitive deficits produced by chronic drug use. Full article
(This article belongs to the Special Issue Neuroactive Compounds)
Open AccessReview Antiplasmodial Natural Products
Molecules 2011, 16(3), 2146-2190; doi:10.3390/molecules16032146
Received: 25 January 2011 / Revised: 15 February 2011 / Accepted: 2 March 2011 / Published: 4 March 2011
Cited by 39 | PDF Full-text (390 KB)
Abstract
Malaria is a human infectious disease that is caused by four species of Plasmodium. It is responsible for more than 1 million deaths per year. Natural products contain a great variety of chemical structures and have been screened for antiplasmodial activity as [...] Read more.
Malaria is a human infectious disease that is caused by four species of Plasmodium. It is responsible for more than 1 million deaths per year. Natural products contain a great variety of chemical structures and have been screened for antiplasmodial activity as potential sources of new antimalarial drugs. This review highlights studies on natural products with antimalarial and antiplasmodial activity reported in the literature from January 2009 to November 2010. A total of 360 antiplasmodial natural products comprised of terpenes, including iridoids, sesquiterpenes, diterpenes, terpenoid benzoquinones, steroids, quassinoids, limonoids, curcubitacins, and lanostanes; flavonoids; alkaloids; peptides; phenylalkanoids; xanthones; naphthopyrones; polyketides, including halenaquinones, peroxides, polyacetylenes, and resorcylic acids; depsidones; benzophenones; macrolides; and miscellaneous compounds, including halogenated compounds and chromenes are listed in this review. Full article
(This article belongs to the Section Natural Products)
Open AccessReview Tannins of Constant Structure in Medicinal and Food Plants—Hydrolyzable Tannins and Polyphenols Related to Tannins
Molecules 2011, 16(3), 2191-2217; doi:10.3390/molecules16032191
Received: 19 January 2011 / Revised: 24 February 2011 / Accepted: 28 February 2011 / Published: 4 March 2011
Cited by 37 | PDF Full-text (583 KB)
Abstract
In addition to the commonly used classification as hydrolyzable tannins and condensed tannins, tannins can also be categorized into two other types: polyphenols of constant chemical structure (Type A) and polyphenols of variable composition (Type B). Both types of tannins and related [...] Read more.
In addition to the commonly used classification as hydrolyzable tannins and condensed tannins, tannins can also be categorized into two other types: polyphenols of constant chemical structure (Type A) and polyphenols of variable composition (Type B). Both types of tannins and related polyphenols account for a large part of plant polyphenols, but accurate structure-activity correlations on a molecular basis can be determined mainly for type A compounds, among which are hydrolysable tannins such as the ellagitannins and their oxidized congeners, some gallotannins, epigallocatechin gallate, caffetannins, etc. Among the activities determined on a molecular basis are the chemical, biological and pharmacological actions such as superoxide anion scavenging, apoptosis, antitumor, anti-EVB, anti-MRSA and anti-plasmin inhibitory activities, etc., in addition to their fundamental activities, i.e., binding to proteins, large molecular compounds and metallic ions, and antioxidant activities. Some structure-specific activities were found for the condensation of dehydroellagitannins with co-existing compounds under mild conditions, and the host-mediated antitumor actions of ellagitannin oligomers. Structures and activities of metabolites of geraniin, a dehydroellagitannin, were revealed. Some stilbenoids and phlorotannins of firm structures have been known to have many activities similar to those of the type A tannins. Full article
(This article belongs to the Special Issue Tannins)
Open AccessReview Analgesic-like Activity of Essential Oils Constituents
Molecules 2011, 16(3), 2233-2252; doi:10.3390/molecules16032233
Received: 4 January 2011 / Revised: 10 February 2011 / Accepted: 4 March 2011 / Published: 7 March 2011
Cited by 44 | PDF Full-text (280 KB)
Abstract
Research on neuroactive drugs is a pharmaceutical sector of high interest and growth. The discovery of efficient drugs that can relieve pain is a subject of research in the pharmaceutical industry and academic field because pain is a symptom of many diseases. [...] Read more.
Research on neuroactive drugs is a pharmaceutical sector of high interest and growth. The discovery of efficient drugs that can relieve pain is a subject of research in the pharmaceutical industry and academic field because pain is a symptom of many diseases. This review will summarize results on the discovery of essential oil constituents with analgesic-like activity from the chemical and pharmacological perspectives. Overall, 43 bioactive compounds were selected in nociception models. Among them, 62.8% were monoterpenes, 18.6% sesquiterpenes and other constituents represented 18.6%. The data show the potential of this group of natural product chemicals as analgesic drugs that may be useful for therapeutic purposes. Full article
(This article belongs to the Special Issue Neuroactive Compounds)
Figures

Open AccessReview Wine and Grape Tannin Interactions with Salivary Proteins and Their Impact on Astringency: A Review of Current Research
Molecules 2011, 16(3), 2348-2364; doi:10.3390/molecules16032348
Received: 9 February 2011 / Revised: 2 March 2011 / Accepted: 9 March 2011 / Published: 11 March 2011
Cited by 50 | PDF Full-text (225 KB)
Abstract
Astringency is an important characteristic of red wine quality. The sensation is generally thought to be produced by the interaction of wine tannins with salivary proteins and the subsequent aggregation and precipitation of protein-tannin complexes. The importance of wine astringency for marketability [...] Read more.
Astringency is an important characteristic of red wine quality. The sensation is generally thought to be produced by the interaction of wine tannins with salivary proteins and the subsequent aggregation and precipitation of protein-tannin complexes. The importance of wine astringency for marketability has led to a wealth of research on the causes of astringency and how tannins impact the quality of the sensation, particularly with respect to tannin structure. Ultimately, the understanding of how tannin structure impacts astringency will allow the controlled manipulation of tannins via such methods as micro-oxygenation or fining to improve the quality of wines. Full article
(This article belongs to the Special Issue Tannins)
Open AccessReview Quantitative Mass Spectrometry for Bacterial Protein Toxins — A Sensitive, Specific, High-Throughput Tool for Detection and Diagnosis
Molecules 2011, 16(3), 2391-2413; doi:10.3390/molecules16032391
Received: 14 February 2011 / Revised: 1 March 2011 / Accepted: 9 March 2011 / Published: 14 March 2011
Cited by 26 | PDF Full-text (1625 KB)
Abstract
Matrix-assisted laser-desorption time-of-flight (MALDI-TOF) mass spectrometry (MS) is a valuable high-throughput tool for peptide analysis. Liquid chromatography electrospray ionization (LC-ESI) tandem-MS provides sensitive and specific quantification of small molecules and peptides. The high analytic power of MS coupled with high-specificity substrates is [...] Read more.
Matrix-assisted laser-desorption time-of-flight (MALDI-TOF) mass spectrometry (MS) is a valuable high-throughput tool for peptide analysis. Liquid chromatography electrospray ionization (LC-ESI) tandem-MS provides sensitive and specific quantification of small molecules and peptides. The high analytic power of MS coupled with high-specificity substrates is ideally suited for detection and quantification of bacterial enzymatic activities. As specific examples of the MS applications in disease diagnosis and select agent detection, we describe recent advances in the analyses of two high profile protein toxin groups, the Bacillus anthracis toxins and the Clostridium botulinum neurotoxins. The two binary toxins produced by B. anthracis consist of protective antigen (PA) which combines with lethal factor (LF) and edema factor (EF), forming lethal toxin and edema toxin respectively. LF is a zinc-dependent endoprotease which hydrolyzes specific proteins involved in inflammation and immunity. EF is an adenylyl cyclase which converts ATP to cyclic-AMP. Toxin-specific enzyme activity for a strategically designed substrate, amplifies reaction products which are detected by MALDI-TOF-MS and LC-ESI-MS/MS. Pre-concentration/purification with toxin specific monoclonal antibodies provides additional specificity. These combined technologies have achieved high specificity, ultrasensitive detection and quantification of the anthrax toxins. We also describe potential applications to diseases of high public health impact, including Clostridium difficile glucosylating toxins and the Bordetella pertussis adenylyl cyclase. Full article
(This article belongs to the Special Issue Toxins - Organic and Analytical Chemistry)
Open AccessReview Allobetulin and Its Derivatives: Synthesis and Biological Activity
Molecules 2011, 16(3), 2443-2466; doi:10.3390/molecules16032443
Received: 22 February 2011 / Revised: 9 March 2011 / Accepted: 11 March 2011 / Published: 14 March 2011
Cited by 30 | PDF Full-text (233 KB)
Abstract
This review covers the chemistry of allobetulin analogs, including their formation by rearrangement from betulin derivatives, their further derivatisation, their fusion with heterocyclic rings, and any further rearrangements of allobetulin compounds including ring opening, ring contraction and ring expansion reactions. In the [...] Read more.
This review covers the chemistry of allobetulin analogs, including their formation by rearrangement from betulin derivatives, their further derivatisation, their fusion with heterocyclic rings, and any further rearrangements of allobetulin compounds including ring opening, ring contraction and ring expansion reactions. In the last part, the most important biological activities of allobetulin derivatives are listed. One hundred and fifteen references are cited and the relevant literature is covered, starting in 1922 up to the end of 2010. Full article
Open AccessReview Miniproteins as Phage Display-Scaffolds for Clinical Applications
Molecules 2011, 16(3), 2467-2485; doi:10.3390/molecules16032467
Received: 23 December 2010 / Revised: 4 March 2011 / Accepted: 7 March 2011 / Published: 14 March 2011
Cited by 13 | PDF Full-text (1214 KB)
Abstract
Miniproteins are currently developed as alternative, non-immunoglobin proteins for the generation of novel binding motifs. Miniproteins are rigid scaffolds that are stabilised by alpha-helices, beta-sheets and disulfide-constrained secondary structural elements. They are tolerant to multiple amino acid substitutions, which allow for the [...] Read more.
Miniproteins are currently developed as alternative, non-immunoglobin proteins for the generation of novel binding motifs. Miniproteins are rigid scaffolds that are stabilised by alpha-helices, beta-sheets and disulfide-constrained secondary structural elements. They are tolerant to multiple amino acid substitutions, which allow for the integration of a randomised affinity function into the stably folded framework. These properties classify miniprotein scaffolds as promising tools for lead structure generation using phage display technologies. Owing to their high enzymatic resistance and structural stability, miniproteins are ideal templates to display binding epitopes for medical applications in vivo. This review summarises the characteristics and the engineering of miniproteins as a novel class of scaffolds to generate of alternative binding agents using phage display screening. Moreover, recent developments for therapeutic and especially diagnostic applications of miniproteins are reviewed. Full article
(This article belongs to the Special Issue Phage Display of Combinatorial Libraries)
Open AccessReview Challenges and Perspectives of Chemical Biology, a Successful Multidisciplinary Field of Natural Sciences
Molecules 2011, 16(3), 2672-2687; doi:10.3390/molecules16032672
Received: 9 February 2011 / Revised: 9 March 2011 / Accepted: 15 March 2011 / Published: 23 March 2011
Cited by 2 | PDF Full-text (701 KB)
Abstract Objects, goals, and main methods as well as perspectives of chemical biology are discussed. This review is focused on the fundamental aspects of this emerging field of life sciences: chemical space, the small molecule library and chemical sensibilization (small molecule microassays). Full article
(This article belongs to the Special Issue Diversity Oriented Synthesis)
Open AccessReview Glycosides, Depression and Suicidal Behaviour: The Role of Glycoside-Linked Proteins
Molecules 2011, 16(3), 2688-2713; doi:10.3390/molecules16032688
Received: 17 December 2010 / Revised: 17 March 2011 / Accepted: 18 March 2011 / Published: 23 March 2011
Cited by 4 | PDF Full-text (487 KB)
Abstract
Nowadays depression and suicide are two of the most important worldwide public health problems. Although their specific molecular mechanisms are still largely unknown, glycosides can play a fundamental role in their pathogenesis. These molecules act presumably through the up-regulation of plasticity-related proteins: [...] Read more.
Nowadays depression and suicide are two of the most important worldwide public health problems. Although their specific molecular mechanisms are still largely unknown, glycosides can play a fundamental role in their pathogenesis. These molecules act presumably through the up-regulation of plasticity-related proteins: probably they can have a presynaptic facilitatory effect, through the activation of several intracellular signaling pathways that include molecules like protein kinase A, Rap-1, cAMP, cADPR and G proteins. These proteins take part in a myriad of brain functions such as cell survival and synaptic plasticity. In depressed suicide victims, it has been found that their activity is strongly decreased, primarily in hippocampus and prefrontal cortex. These studies suggest that glycosides can regulate neuroprotection through Rap-1 and other molecules, and may play a crucial role in the pathophysiology of depression and suicide. Full article
(This article belongs to the Special Issue Glycosides)
Open AccessReview Essential Oils and Their Constituents: Anticonvulsant Activity
Molecules 2011, 16(3), 2726-2742; doi:10.3390/molecules16032726
Received: 13 December 2010 / Revised: 18 March 2011 / Accepted: 22 March 2011 / Published: 23 March 2011
Cited by 28 | PDF Full-text (216 KB)
Abstract
A literature-based survey of plants species and their essential oils with anticonvulsant activity was carried out. As results, 30 species belonging to 13 families and 23 genera were identified for their activities in the experimental models used for anticonvulsant drug screening. Thirty [...] Read more.
A literature-based survey of plants species and their essential oils with anticonvulsant activity was carried out. As results, 30 species belonging to 13 families and 23 genera were identified for their activities in the experimental models used for anticonvulsant drug screening. Thirty chemical constituents of essential oils with anticonvulsant properties were described. Information on these 30 species is presented together with isolated bioactive compound studies. Full article
(This article belongs to the Special Issue Neuroactive Compounds)

Journal Contact

MDPI AG
Molecules Editorial Office
St. Alban-Anlage 66, 4052 Basel, Switzerland
molecules@mdpi.com
Tel. +41 61 683 77 34
Fax: +41 61 302 89 18
Editorial Board
Contact Details Submit to Molecules
Back to Top