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

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Open AccessArticle Synthesis of Oligodeoxynucleotides Using Fully Protected Deoxynucleoside 3′-Phosphoramidite Building Blocks and Base Recognition of Oligodeoxynucleotides Incorporating N3-Cyano-Ethylthymine
Molecules 2010, 15(11), 7509-7531; doi:10.3390/molecules15117509
Received: 27 August 2010 / Revised: 8 October 2010 / Accepted: 14 October 2010 / Published: 27 October 2010
Cited by 1 | PDF Full-text (473 KB)
Abstract
Oligodeoxynucleotide (ODN) synthesis, which avoids the formation of side products, is of great importance to biochemistry-based technology development. One side reaction of ODN synthesis is the cyanoethylation of the nucleobases. We suppressed this reaction by synthesizing ODNs using fully protected deoxynucleoside 3′-phosphoramidite building
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Oligodeoxynucleotide (ODN) synthesis, which avoids the formation of side products, is of great importance to biochemistry-based technology development. One side reaction of ODN synthesis is the cyanoethylation of the nucleobases. We suppressed this reaction by synthesizing ODNs using fully protected deoxynucleoside 3′-phosphoramidite building blocks, where the remaining reactive nucleobase residues were completely protected with acyl-, diacyl-, and acyl-oxyethylene-type groups. The detailed analysis of cyanoethylation at the nucleobase site showed that N3-protection of the thymine base efficiently suppressed the Michael addition of acrylonitrile. An ODN incorporating N3-cyanoethylthymine was synthesized using the phosphoramidite method, and primer extension reactions involving this ODN template were examined. As a result, the modified thymine produced has been proven to serve as a chain terminator. Full article
(This article belongs to the Special Issue Protecting Group in Organic Synthesis)
Open AccessArticle Antibacterial Effects of the Essential Oils of Commonly Consumed Medicinal Herbs Using an In Vitro Model
Molecules 2010, 15(11), 7532-7546; doi:10.3390/molecules15117532
Received: 28 September 2010 / Revised: 18 October 2010 / Accepted: 25 October 2010 / Published: 27 October 2010
Cited by 107 | PDF Full-text (159 KB)
Abstract
The chemical composition and antibacterial activity of essential oils from 10 commonly consumed herbs: Citrus aurantium, C. limon, Lavandula angustifolia, Matricaria chamomilla, Mentha piperita, M. spicata, Ocimum basilicum, Origanum vulgare, Thymus vulgaris and Salvia officinalis have
[...] Read more.
The chemical composition and antibacterial activity of essential oils from 10 commonly consumed herbs: Citrus aurantium, C. limon, Lavandula angustifolia, Matricaria chamomilla, Mentha piperita, M. spicata, Ocimum basilicum, Origanum vulgare, Thymus vulgaris and Salvia officinalis have been determined. The antibacterial activity of these oils and their main components; i.e. camphor, carvacrol, 1,8-cineole, linalool, linalyl acetate, limonene, menthol, a-pinene, b-pinene, and thymol were assayed against the human pathogenic bacteria Bacillus subtilis, Enterobacter cloacae, Escherichia coli O157:H7, Micrococcus flavus, Proteus mirabilis, Pseudomonas aeruginosa, Salmonella enteritidis, S. epidermidis, S. typhimurium, and Staphylococcus aureus. The highest and broadest activity was shown by O. vulgare oil. Carvacrol had the highest antibacterial activity among the tested components. Full article
Open AccessArticle Free Radical Scavenging Activity and Characterization of Sesquiterpenoids in Four Species of Curcuma Using a TLC Bioautography Assay and GC-MS Analysis
Molecules 2010, 15(11), 7547-7557; doi:10.3390/molecules15117547
Received: 6 October 2010 / Revised: 19 October 2010 / Accepted: 25 October 2010 / Published: 27 October 2010
Cited by 34 | PDF Full-text (318 KB)
Abstract
The sesquiterpenoids are one of major groups of antioxidants in Curcuma besides curcuminoids. However, the real substances contributing to the antioxidant activity are still unknown. In this paper, the antioxidant activity of sesquiterpenoids in four species and two essential oils from Curcuma genus
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The sesquiterpenoids are one of major groups of antioxidants in Curcuma besides curcuminoids. However, the real substances contributing to the antioxidant activity are still unknown. In this paper, the antioxidant activity of sesquiterpenoids in four species and two essential oils from Curcuma genus was determined and compared based on TLC separation and DPPH bioautography assay. Their antioxidant capacities were quantitatively evaluated using densitometry with detection at 530 nm (λreference = 800 nm) using vitamin C as reference. The results showed that Curcuma longa rhizomes had the highest antioxidant capacity while C. phaeocaulis presented the lowest one among the four species of Curcuma. Moreover, essential oil of C. wenyujin showed higher antioxidant potential than that of C. longa. The main TLC bands with antioxidant activity of the four species of Curcuma were collected and characterized using GC-MS, and thus curzerene, furanodiene, α-turmerone, β-turmerone and β-sesquiphellandrene were determined as major sesquiterpenoids with antioxidant activity in Curcuma. Full article
(This article belongs to the Special Issue Radical Chemistry)
Open AccessArticle Antifungal Activity of the Essential Oil of Illicium verum Fruit and Its Main Component trans-Anethole
Molecules 2010, 15(11), 7558-7569; doi:10.3390/molecules15117558
Received: 14 October 2010 / Revised: 20 October 2010 / Accepted: 25 October 2010 / Published: 27 October 2010
Cited by 40 | PDF Full-text (171 KB)
Abstract
In order to identify natural products for plant disease control, the essential oil of star anise (Illicium verum Hook. f.) fruit was investigated for its antifungal activity on plant pathogenic fungi. The fruit essential oil obtained by hydro-distillation was analyzed for its
[...] Read more.
In order to identify natural products for plant disease control, the essential oil of star anise (Illicium verum Hook. f.) fruit was investigated for its antifungal activity on plant pathogenic fungi. The fruit essential oil obtained by hydro-distillation was analyzed for its chemical composition by gas chromatography (GC) and gas chromatography-mass spectrometry (GC-MS). trans-Anethole (89.5%), 2-(1-cyclopentenyl)-furan (0.9%) and cis-anethole (0.7%) were found to be the main components among 22 identified compounds, which accounted for 94.6% of the total oil. The antifungal activity of the oil and its main component trans-anethole against plant pathogenic fungi were determined. Both the essential oil and trans-anethole exhibited strong inhibitory effect against all test fungi indicating that most of the observed antifungal properties was due to the presence of trans-anethole in the oil, which could be developed as natural fungicides for plant disease control in fruit and vegetable preservation. Full article
Open AccessArticle Synthesis and Characterization of a Ru(II) Complex with Functionalized Phenanthroline Ligands Having Single-Double Linked Anthracenyl and 1-Methoxy-1-buten-3-yne Moieties
Molecules 2010, 15(11), 7570-7581; doi:10.3390/molecules15117570
Received: 8 September 2010 / Accepted: 19 October 2010 / Published: 27 October 2010
Cited by 10 | PDF Full-text (226 KB) | Supplementary Files
Abstract
Two series of bidentate polypyridine ligands, made of phenanthroline chelating subunits having substituted mono-and di-anthracenyl groups, and 1-methoxy-1-buten-3-yne at the 4 and 7-positions with the corresponding heteroleptic Ru(II) complex have been synthesized and characterized. The complex is formulated as [(Ru(L1)(L2
[...] Read more.
Two series of bidentate polypyridine ligands, made of phenanthroline chelating subunits having substituted mono-and di-anthracenyl groups, and 1-methoxy-1-buten-3-yne at the 4 and 7-positions with the corresponding heteroleptic Ru(II) complex have been synthesized and characterized. The complex is formulated as [(Ru(L1)(L2)(NCS)2)], (where L1 = 4-(9-dianthracenyl-10-(2,3-dimethylacrylic acid)-7-(9-anthracenyl-10-(2,3-dimethylacrylic acid)-1,10-phenanthroline and L2 = 4,7-bis(1-methoxy-1-buten-3-yne)-1,10-phenanthroline). The Ru(II) complex shows characteristic broad and intense metal-to-ligand charge transfer (MLCT) bands absorption and appreciable photoluminescence spanning the visible region. The ligands and complex were characterized by FT-IR, 1H, 13C NMR spectroscopy, UV-Vis, photoluminescence and elemental analysis (see in supplementary materials). The anchoring groups in both ligands have allowed an extended delocalization of acceptor orbital of the metal-to-ligand charge-transfer (MLCT) excited state. Full article
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Open AccessCommunication Synthesis of a Highly Luminescent Three-Dimensional Pyrene Dye Based on the Spirobifluorene Skeleton
Molecules 2010, 15(11), 7582-7592; doi:10.3390/molecules15117582
Received: 24 August 2010 / Revised: 25 October 2010 / Accepted: 27 October 2010 / Published: 28 October 2010
Cited by 17 | PDF Full-text (325 KB)
Abstract
We have synthesized a highly luminescent (log e > 5.0, F > 0.9) pyrene dye based on a spirobifluorene skeleton [2,2′,7,7′-tetrakis(7-tert-butyl-1-pyrenyl)-9,9′-spirobi[9H-fluorene; 4-PySBF]. The use of spirobifluorene prevents fluorescence quenching by intramolecular energy transfer and/or electron transfer among the chromophores in
[...] Read more.
We have synthesized a highly luminescent (log e > 5.0, F > 0.9) pyrene dye based on a spirobifluorene skeleton [2,2′,7,7′-tetrakis(7-tert-butyl-1-pyrenyl)-9,9′-spirobi[9H-fluorene; 4-PySBF]. The use of spirobifluorene prevents fluorescence quenching by intramolecular energy transfer and/or electron transfer among the chromophores in the excited state. The emission spectra of 4-PySBF exhibited a red shift of 20 nm in comparison to a model compound [9,9′-dioctyl-2,7-bis(7-tert-butyl-1-pyrenyl)-9H-fluorene; 2-PyF], but its UV-Vis spectrum remained unchanged. Full article
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Open AccessArticle Synthesis and Application in Polypropylene of a Novel of Phosphorus-Containing Intumescent Flame Retardant
Molecules 2010, 15(11), 7593-7602; doi:10.3390/molecules15117593
Received: 17 September 2010 / Accepted: 13 October 2010 / Published: 28 October 2010
Cited by 13 | PDF Full-text (221 KB)
Abstract
A novel phosphorus-containing triazine oligomer poly(2-morpholinyl-4-penta-erythritol phosphate-1,3,5-triazine) (PMPT) was synthesized as a kind of tri-component intumescent flame retardant (IFR). The chemical structure of PMPT was characterized by FTIR, 1H-NMR and 31P-NMR, and the mechanical and flammability properties of FR-PP were measured.
[...] Read more.
A novel phosphorus-containing triazine oligomer poly(2-morpholinyl-4-penta-erythritol phosphate-1,3,5-triazine) (PMPT) was synthesized as a kind of tri-component intumescent flame retardant (IFR). The chemical structure of PMPT was characterized by FTIR, 1H-NMR and 31P-NMR, and the mechanical and flammability properties of FR-PP were measured. The FTIR results showed that the expected chemical reactions had  happened at each step. The 1H-NMR and 31P-NMR spectra also agreed with the chemical structure of PMPT. The slight effect of PMPT on the mechanical properties of FR-PP suggested that PMPT and PP are compatible. The high limited oxygen index (LOI) values of FR-PP revealed that PMPT was an efficient IFR and there was the synergistic effect between PMPT and ammonium polyphosphate/ pentaerythritol (APP/PER). Full article
Open AccessArticle Reduction of Diphenyl Diselenide and Analogs by Mammalian Thioredoxin Reductase Is Independent of Their Gluthathione Peroxidase-Like Activity: A Possible Novel Pathway for Their Antioxidant Activity
Molecules 2010, 15(11), 7699-7714; doi:10.3390/molecules15117699
Received: 23 August 2010 / Revised: 14 October 2010 / Accepted: 26 October 2010 / Published: 28 October 2010
Cited by 35 | PDF Full-text (319 KB)
Abstract
Since the successful use of the organoselenium drug ebselen in clinical trials for the treatment of neuropathological conditions associated with oxidative stress, there have been concerted efforts geared towards understanding the precise mechanism of action of ebselen and other organoselenium compounds, especially the
[...] Read more.
Since the successful use of the organoselenium drug ebselen in clinical trials for the treatment of neuropathological conditions associated with oxidative stress, there have been concerted efforts geared towards understanding the precise mechanism of action of ebselen and other organoselenium compounds, especially the diorganyl diselenides such as diphenyl diselenide, and its analogs. Although the mechanism of action of ebselen and other organoselenium compounds has been shown to be related to their ability to generally mimic native glutathione peroxidase (GPx), only ebselen however has been shown to serve as a substrate for the mammalian thioredoxin reductase (TrxR), demonstrating another component of its pharmacological mechanisms. In fact, there is a dearth of information on the ability of other organoselenium compounds, especially diphenyl diselenide and its analogs, to serve as substrates for the mammalian enzyme thioredoxin reductase. Interestingly, diphenyl diselenide shares several antioxidant and neuroprotective properties with ebselen. Hence in the present study, we tested the hypothesis that diphenyl diselenide and some of its analogs (4,4’-bistrifluoromethyldiphenyl diselenide, 4,4’-bismethoxy-diphenyl diselenide, 4.4’-biscarboxydiphenyl diselenide, 4,4’-bischlorodiphenyl diselenide, 2,4,6,2’,4’,6’-hexamethyldiphenyl diselenide) could also be substrates for rat hepatic TrxR. Here we show for the first time that diselenides are good substrates for mammalian TrxR, but not necessarily good mimetics of GPx, and vice versa. For instance, bis-methoxydiphenyl diselenide had no GPx activity, whereas it was a good substrate for reduction by TrxR. Our experimental observations indicate a possible dissociation between the two pathways for peroxide degradation (either via substrate for TrxR or as a mimic of GPx). Consequently, the antioxidant activity of diphenyl diselenide and analogs can be attributed to their capacity to be substrates for mammalian TrxR and we therefore conclude that subtle changes in the aryl moiety of diselenides can be used as tool for dissociation of GPx or TrxR pathways as mechanism triggering their antioxidant activities. Full article
(This article belongs to the Section Medicinal Chemistry)
Open AccessArticle Comparison of Microwave-Assisted and Conventional Hydrodistillation in the Extraction of Essential Oils from Mango (Mangifera indica L.) Flowers
Molecules 2010, 15(11), 7715-7723; doi:10.3390/molecules15117715
Received: 27 August 2010 / Revised: 27 September 2010 / Accepted: 11 October 2010 / Published: 29 October 2010
Cited by 29 | PDF Full-text (123 KB)
Abstract
Microwave-assisted hydrodistillation (MAHD) is an advanced hydrodistillation (HD) technique, in which a microwave oven is used in the extraction process. MAHD and HD methods have been compared and evaluated for their effectiveness in the isolation of essential oils from fresh mango (Mangifera
[...] Read more.
Microwave-assisted hydrodistillation (MAHD) is an advanced hydrodistillation (HD) technique, in which a microwave oven is used in the extraction process. MAHD and HD methods have been compared and evaluated for their effectiveness in the isolation of essential oils from fresh mango (Mangifera indica L.) flowers. MAHD offers important advantages over HD in terms of energy savings and extraction time (75 min against 4 h). The composition of the extracted essential oils was investigated by GC-FID and GC-MS. Results indicate that the use of microwave irradiation did not adversely influence the composition of the essential oils. MAHD was also found to be a green technology. Full article
Open AccessArticle The Knoevenagel-Doebner Reaction on 1,2-O-(2,2,2-Trichloroethylidene) Derivatives of D-Gluco- and D-Manno- furanose
Molecules 2010, 15(11), 7724-7731; doi:10.3390/molecules15117724
Received: 8 October 2010 / Revised: 25 October 2010 / Accepted: 28 October 2010 / Published: 29 October 2010
Cited by 4 | PDF Full-text (251 KB)
Abstract
The synthesis of new α,β-unsaturated furanuronic acid derivatives of α-gluco- (3), β-gluco- (6) and β-manno-chloraloses (9) via a convenient one pot procedure using the Knoevenagel-Doebner reaction approach
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The synthesis of new α,β-unsaturated furanuronic acid derivatives of α-gluco- (3), β-gluco- (6) and β-manno-chloraloses (9) via a convenient one pot procedure using the Knoevenagel-Doebner reaction approach are described. The dialdofuranose derivatives were reacted with malonic acid under Knoevenagel-Doebner reaction conditions and (E)-α,β-unsaturated furanuronic acid derivatives were obtained. Full article
Open AccessCommunication Application of Phosphine-Phosphite Ligands in the Iridium Catalyzed Enantioselective Hydrogenation of 2-Methylquinoline
Molecules 2010, 15(11), 7732-7741; doi:10.3390/molecules15117732
Received: 6 October 2010 / Revised: 26 October 2010 / Accepted: 28 October 2010 / Published: 29 October 2010
Cited by 14 | PDF Full-text (121 KB)
Abstract
The hydrogenation of 2-methylquinoline with Ir catalysts based on chiral phosphine-phosphites has been investigated. It has been observed that the reaction is very sensitive to the nature of the ligand. Optimization of the catalyst, allowed by the highly modular structure of these phosphine-phosphites,
[...] Read more.
The hydrogenation of 2-methylquinoline with Ir catalysts based on chiral phosphine-phosphites has been investigated. It has been observed that the reaction is very sensitive to the nature of the ligand. Optimization of the catalyst, allowed by the highly modular structure of these phosphine-phosphites, has improved the enantioselectivity of the reaction up to 73% ee. The influence of additives in this reaction has also been investigated. Contrary to the beneficial influence observed in related catalytic systems, iodine has a deleterious effect in the present case. Otherwise, aryl phosphoric acids produce a positive impact on catalyst activity without a decrease on enantioselectivity. Full article
(This article belongs to the Special Issue Bifunctional Catalysis)
Open AccessCommunication α-Lithiation and Electrophilic Substitution of 1,4,4-Trimethyl-3,4-dihydroquinolin-2-one
Molecules 2010, 15(11), 7742-7749; doi:10.3390/molecules15117742
Received: 9 September 2010 / Revised: 27 October 2010 / Accepted: 28 October 2010 / Published: 29 October 2010
PDF Full-text (111 KB)
Abstract Treatment of 1,4,4-trimethyl-3,4-dihydroquinolin-2(1H)-one (2) with lithium diisopropylamide (LDA) followed by a wide range of electrophiles give the corresponding 4,4-dimethyl-3-substituted-3,4-dihydroquinolin-2-ones 3-13, providing a very mild electrophilic substitution of the 4,4-dimethyl-1,2,3,4-tetrahydroquinoline core. Full article
(This article belongs to the Section Organic Synthesis)
Open AccessArticle Farnesol, a Potential Efflux Pump Inhibitor in Mycobacterium smegmatis
Molecules 2010, 15(11), 7750-7762; doi:10.3390/molecules15117750
Received: 1 September 2010 / Revised: 2 October 2010 / Accepted: 25 October 2010 / Published: 29 October 2010
Cited by 26 | PDF Full-text (171 KB)
Abstract
The active multidrug efflux pump (EP) has been described as one of the mechanisms involved in the natural drug resistance of bacteria, such as mycobacteria. As a result, the development of efflux pumps inhibitors (EPIs) is an important topic. In this study, a
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The active multidrug efflux pump (EP) has been described as one of the mechanisms involved in the natural drug resistance of bacteria, such as mycobacteria. As a result, the development of efflux pumps inhibitors (EPIs) is an important topic. In this study, a checkerboard synergy assay indicated that farnesol both decreased the minimum inhibitory concentration (MIC) of ethidium bromide (EtBr) 8-fold against Mycobacterium smegmatis (M. smegmatis) mc2155 ATCC 700084 when incorporated at a concentration of 32 μg/mL (FICI = 0.625) and decreased MIC 4-fold at 16 μg/mL (FICI = 0.375). Farnesol also showed synergism when combined with rifampicin. A real-time 96-well plate fluorometric method was used to assess the ability of farnesol to inhibit EPs in comparison withfour positive EPIs: chlorpromazine, reserpine, verapamil, and carbonyl cyanide m-chlorophenylhydrazone (CCCP). Farnesol significantly enhanced the accumulation of EtBr and decreased the efflux of EtBr in M. smegmatis; these results suggest that farnesol acts as an inhibitor of mycobacterial efflux pumps. Full article
Open AccessArticle Changes of Flavan-3-ols with Different Degrees of Polymerization in Seeds of ‘Shiraz’, ‘Cabernet Sauvignon’ and ‘Marselan’ Grapes after Veraison
Molecules 2010, 15(11), 7763-7774; doi:10.3390/molecules15117763
Received: 12 October 2010 / Revised: 19 October 2010 / Accepted: 1 November 2010 / Published: 2 November 2010
Cited by 7 | PDF Full-text (461 KB)
Abstract
Flavan-3-ols consist of flavan-3-ol monomers and polymers with different degrees of polymerization (DP). In this study, flavan-3-ol extracts from grape seeds were well separated into three fractions including monomers, oligomers (2 10), by means of normal-phase HPLC-MS. The different patterns of these three
[...] Read more.
Flavan-3-ols consist of flavan-3-ol monomers and polymers with different degrees of polymerization (DP). In this study, flavan-3-ol extracts from grape seeds were well separated into three fractions including monomers, oligomers (2 < DP < 10) and polymers (DP > 10), by means of normal-phase HPLC-MS. The different patterns of these three fractions were analyzed in three Vitis vinifera cultivars (‘Shiraz’, ‘Cabernet Sauvignon’ and ‘Marselan’) seeds from veraison to harvest. The results showed: (1) polymers were the main form of flavan-3-ols in grape seeds and monomers accounted for only a small proportion; (2) the contents of flavan-3-ol monomers in the seeds of three grape cultivars all exhibited a gradually decreasing trend with a little fluctuation, whereas the patterns of the change of contents of oligomers and polymers were extremely different among grape cultivars; the contents of flavan-3-ol oligomers were enhanced in the seeds of ‘Cabernet Sauvignon’, but were reduced in the other two cultivars; (3) with regard to the proportion of flavan-3-ols with a certain DP to total flavan-3-ols, both flavan-3-ol monomers and flavan-3-ols with low DP fell in proportion, while the flavan-3-ols with high DP increased correspondingly. These findings indicate that flavan-3-ol polymerization in developing seeds is variety-dependent and may be genetically regulated. Full article
Open AccessArticle Cytotoxic and Insecticidal Activities of Derivatives of Harmine, a Natural Insecticidal Component Isolated from Peganum harmala
Molecules 2010, 15(11), 7775-7791; doi:10.3390/molecules15117775
Received: 23 August 2010 / Revised: 25 October 2010 / Accepted: 27 October 2010 / Published: 2 November 2010
Cited by 14 | PDF Full-text (247 KB)
Abstract
In a continuing effort to develop novel β-carbolines endowed with better insecticidal activity, a simple high-yielding method for the synthesis of harmine compounds starting from L-tryptophan has been developed and a series of 1,3-substituted β-carboline derivatives have been synthesized and evaluated for their
[...] Read more.
In a continuing effort to develop novel β-carbolines endowed with better insecticidal activity, a simple high-yielding method for the synthesis of harmine compounds starting from L-tryptophan has been developed and a series of 1,3-substituted β-carboline derivatives have been synthesized and evaluated for their cytotoxicity against insect cultured Sf9 cell line in vitro and insecticidal activities against 4th instar larvae of mosquitos, Culex pipiens quinquefasciatus and mustard aphid, Lipaphis erysimi. The results demonstrated that 1-phenyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid (compound 2) and methyl 1-phenyl-β-carboline-3-carboxylate (compound 13) represented the best potential compounds, with Sf9 cells inhibition rates of 71.55% and 60.21% after 24 h treatment at concentrations of 50–200 mg/L, respectively. Both compounds 2 and 13 also showed strong insecticidal activity towards 4th instar larvae of mosquitos with LC50 values of 20.82 mg/L and 23.98 mg/L, and their LC90 values were 88.29 mg/L and 295.13 mg/L, respectively. Furthermore, the LC50 values of compounds 2 and 13 against mustard aphids were 53.16 mg/L and 68.05 mg/L, and their LC90 values were 240.10 mg/L and 418.63 mg/L after 48 h treatment. The in vitro cytotoxicity of these compounds was consistent with the insecticidal activity in vivo. The results indicated that the 1- and 3-positions of the β-carboline ring deserve further investigation to develop biorational insecticides based on the natural compound harmine as a lead compound. Full article
Open AccessArticle New Anti-Inflammatory and Anti-Proliferative Constituents from Fermented Red Mold Rice Monascus purpureus NTU 568
Molecules 2010, 15(11), 7815-7824; doi:10.3390/molecules15117815
Received: 14 October 2010 / Revised: 29 October 2010 / Accepted: 1 November 2010 / Published: 3 November 2010
Cited by 8 | PDF Full-text (277 KB)
Abstract
Six azaphilonoid derivatives, including two new blue fluorescent monapurfluores A (1) and B (2), two known pyridine-containing molecules, monascopyridines C (3) and D (4), and two known monasfluores A (5) and B (
[...] Read more.
Six azaphilonoid derivatives, including two new blue fluorescent monapurfluores A (1) and B (2), two known pyridine-containing molecules, monascopyridines C (3) and D (4), and two known monasfluores A (5) and B (6), were isolated and characterized from red mold rice fermented by Monascus purpureus NTU 568. Structural elucidation of new isolates was based on nuclear magnetic resonance (1H- NMR, 13C-NMR, COSY, HMQC, and HMBC) and other spectroscopic analyses. Bioactivity evaluation indicated that 1-6 possessed anti-inflammatory activities with dose-dependent relationships for lipopolysaccharide (LPS)-induced nitric oxide production. Furthermore, 1-4 also showed moderate antiproliferative effects against human laryngeal carcinoma (HEp-2) (IC50 = 14.81~20.06 μg/mL) and human colon adenocarcinoma (WiDr) (IC50 = 12.89~21.14 μg/mL). Full article
Open AccessArticle Composition and Antimicrobial Activities of Lippia multiflora Moldenke, Mentha x piperita L. and Ocimum basilicum L. Essential Oils and Their Major Monoterpene Alcohols Alone and in Combination
Molecules 2010, 15(11), 7825-7839; doi:10.3390/molecules15117825
Received: 3 September 2010 / Revised: 21 October 2010 / Accepted: 2 November 2010 / Published: 3 November 2010
Cited by 43 | PDF Full-text (145 KB)
Abstract
Essential oils from leaves of Lippia multiflora, Mentha x piperita and Ocimum basilicum from Burkina Faso were analysed by GC–FID and GC–MS. Major components were p-cymene, thymol, b-caryophyllene, carvacrol and carvone for L. multiflora, menthol and iso-menthone for M.
[...] Read more.
Essential oils from leaves of Lippia multiflora, Mentha x piperita and Ocimum basilicum from Burkina Faso were analysed by GC–FID and GC–MS. Major components were p-cymene, thymol, b-caryophyllene, carvacrol and carvone for L. multiflora, menthol and iso-menthone for M. x piperita and, linalool and eugenol for O. basilicum. The essential oils and their major monoterpene alcohols were tested against nine bacterial strains using the disc diffusion and broth microdilution methods. The essential oils with high phenolic contents were the most effective antimicrobials. The checkerboard method was used to quantify the efficacy of paired combinations of essential oils and their major components. The best synergetic effects among essential oils and major components were obtained with combinations involving O. basilicum essential oil and eugenol, respectively. As phenolic components are characterized by a strong spicy aroma, this study suggests that the selection of certain combinations of EOs could help to reduce the amount of essential oils and consequently reduce any adverse sensory impact in food. Full article
(This article belongs to the Section Natural Products)
Open AccessArticle Inhibitory Effects of Phylligenin and Quebrachitol Isolated from Mitrephora vulpina on Platelet Activating Factor Receptor Binding and Platelet Aggregation
Molecules 2010, 15(11), 7840-7848; doi:10.3390/molecules15117840
Received: 20 September 2010 / Revised: 15 October 2010 / Accepted: 25 October 2010 / Published: 3 November 2010
Cited by 12 | PDF Full-text (173 KB) | Correction | Supplementary Files
Abstract
Phylligenine, together with quebrachitol, stigmasterol and two aporphine alkaloids—oxoputerine and liriodenine—were isolated from the twigs of Mitrephora vulpina C.E.C. Fisch. They were evaluated for their ability to inhibit platelet activating factor (PAF) receptor binding to rabbit platelets using 3H-PAF as a ligand
[...] Read more.
Phylligenine, together with quebrachitol, stigmasterol and two aporphine alkaloids—oxoputerine and liriodenine—were isolated from the twigs of Mitrephora vulpina C.E.C. Fisch. They were evaluated for their ability to inhibit platelet activating factor (PAF) receptor binding to rabbit platelets using 3H-PAF as a ligand and their antiplatelet aggregation effect in human whole blood induced by arachidonic acid (AA), collagen and adenosine diphosphate (ADP). Of all the compounds tested, phylligenin and quebrachitol exhibited potent and concentration-dependent inhibitory effects on PAF receptor binding, with IC50 values of 13.1 and 42.2 µM, respectively. The IC50 value of phylligenin was comparable to that of cedrol (10.2 µM), a potent PAF antagonist. Phylligenin also showed strong dose-dependent inhibitory activity on platelet aggregation induced by AA and ADP. Full article
(This article belongs to the Section Natural Products)
Open AccessArticle Variability of Polyphenol Compounds in Myrtus Communis L. (Myrtaceae) Berries from Corsica
Molecules 2010, 15(11), 7849-7860; doi:10.3390/molecules15117849
Received: 6 September 2010 / Revised: 12 October 2010 / Accepted: 2 November 2010 / Published: 3 November 2010
Cited by 16 | PDF Full-text (150 KB)
Abstract
Polyphenol compounds were extracted from Myrtus communis L. berries (Myrtaceae) by maceration in 70% ethanol and analysed by HPLC-DAD and electrospray mass spectrometry. The Myrtus berries were collected at maturity from seven localities on the island of Corsica (France) and the sampling was
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Polyphenol compounds were extracted from Myrtus communis L. berries (Myrtaceae) by maceration in 70% ethanol and analysed by HPLC-DAD and electrospray mass spectrometry. The Myrtus berries were collected at maturity from seven localities on the island of Corsica (France) and the sampling was carried out during three years. The polyphenol composition of Corsican Myrtus berries was characterized by two phenolic acids, four flavanols, three flavonols and five flavonol glycosides. The major compounds were myricetin-3-O-arabinoside and myricetin-3-O-galactoside. Principal components analysis (PCA) is applied to study the chemical composition and variability of myrtle berries alcoholic extracts from the seven localities. Canonical analysis and PCA data distinguishes two groups of myrtle berries characterized by different concentrations of polyphenols according to soil and years of harvest. The variations in the polyphenol concentration were due to biotic and abiotic factors. Full article
(This article belongs to the Special Issue Phenolics and Polyphenolics)
Open AccessArticle Synthesis and Tumor Cytotoxicity of Novel Amide Derivatives of β-Hederin
Molecules 2010, 15(11), 7871-7883; doi:10.3390/molecules15117871
Received: 9 October 2010 / Revised: 1 November 2010 / Accepted: 2 November 2010 / Published: 3 November 2010
Cited by 9 | PDF Full-text (319 KB)
Abstract
Thirteen novel triterpenoid saponins, designed as amide derivatives of the natural cytotoxic saponin β-hederin, were synthesized by a stepwise glycosylation strategy. The in vitro cytotoxic activity of these compounds was evaluated against five different tumor cell lines. Most of the evaluated compounds showed
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Thirteen novel triterpenoid saponins, designed as amide derivatives of the natural cytotoxic saponin β-hederin, were synthesized by a stepwise glycosylation strategy. The in vitro cytotoxic activity of these compounds was evaluated against five different tumor cell lines. Most of the evaluated compounds showed effective inhibitory activity against at least one tumor cell line at micromolar concentrations. The preliminary structure-activity relationships (SAR) indicate that mide derivatization at C-28 resulted in highly cytotoxic derivatives on specific tumor cell lines, and also resulted in an increase in the antitumor selectivity of β-hederin.  Full article
(This article belongs to the Special Issue Phenolics and Polyphenolics)
Open AccessCommunication Prooxidant/Antioxidant Ratio (ProAntidex) as a Better Index of Net Free Radical Scavenging Potential
Molecules 2010, 15(11), 7884-7892; doi:10.3390/molecules15117884
Received: 6 September 2010 / Revised: 1 October 2010 / Accepted: 19 October 2010 / Published: 3 November 2010
Cited by 10 | PDF Full-text (178 KB)
Abstract
The antioxidant activity of several Malaysian plant extracts was analyzed simultaneously with their pro-oxidant capacity. This ratio represents an index (ProAntidex) of the net free radical scavenging ability of whole plant extracts. We observed that ethanolic extracts of Nephelium lappaceum peel, Fragaria x
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The antioxidant activity of several Malaysian plant extracts was analyzed simultaneously with their pro-oxidant capacity. This ratio represents an index (ProAntidex) of the net free radical scavenging ability of whole plant extracts. We observed that ethanolic extracts of Nephelium lappaceum peel, Fragaria x ananassa leaf, Lawsonia inermis leaf, Syzygium aqueum leaf and grape seed had a lower Pro-Antidex than the commercially available Emblica™ extract which is an antioxidant agent with very low pro-oxidant activity. Among the aqueous extracts, Lawsonia inermis leaf, Nephelium mutobile leaf and grape seed had lower pro-oxidant activity compared to the Emblica™ extract. Among these extracts, aqueous extract of Nephelium mutobile leaf had a very low index of 0.05 compared to 0.69 for Emblica™. Most of the extracts had a far lower ProAntidex compared to the Vitamin C. The index enables us to identify extracts with high net free radical scavenging activity potential. The ProAntidex is beneficial as a screening parameter to the food industries and healthcare. Full article
(This article belongs to the Special Issue Phenolics and Polyphenolics)
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Open AccessArticle Combination of Active Components Enhances the Efficacy of Prunella in Prevention and Treatment of Lung Cancer
Molecules 2010, 15(11), 7893-7906; doi:10.3390/molecules15117893
Received: 19 September 2010 / Revised: 1 November 2010 / Accepted: 2 November 2010 / Published: 4 November 2010
Cited by 20 | PDF Full-text (271 KB)
Abstract
The efficacy of Prunella extracts in the prevention and treatment of lung cancer has been attributed to different components. In this study, an "active components combination model" hypothesis was proposed to explain the anti-tumor activity of Prunella. The efficacy of Prunella extracts
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The efficacy of Prunella extracts in the prevention and treatment of lung cancer has been attributed to different components. In this study, an "active components combination model" hypothesis was proposed to explain the anti-tumor activity of Prunella. The efficacy of Prunella extracts from different regions was compared in vitro and in vivo, and the TNF-α activity in serum of tumor-bearing mice was also evaluated. High performance liquid chromatography (HPLC) was used to analyze the extracts and identify 26 common peaks. Prunella samples from different regions were classified by the cluster analysis method; both P. vulgaris L. from Bozhou and P. asiatica Nakai from Nanjing, which had the highest activities, were further divided into different classes. Six peaks from the HPLC analysis were very similar, and were identified as caffeic acid, rosmarinic acid, rutin, quercetin, oleanolic acid and ursolic acid. The total ratio of these compounds in Prunella from Bozhou and Nanjing were 1.0:14.7:3.9:1.0:4.4:1.4 and 1.0:14.8:4.0:0.8:5.6:1.8, respectively. Total triterpenes and total phenols in Prunella were separated by macroporous resin purification for activity studies. The results showed that total triterpenes and total phenols had anti-lung cancer activity and their combination significantly enhanced the activity. In addition, the combination also significantly increased the TNF-α content compared to total triterpenes or total phenols. The results indicated that the efficacy of Prunella against lung cancer was attributable to multiple components acting at an optimal ratio. Full article
Open AccessArticle Elevated Carbon Dioxide Increases Contents of Flavonoids and Phenolic Compounds, and Antioxidant Activities in Malaysian Young Ginger (Zingiber officinale Roscoe.) Varieties
Molecules 2010, 15(11), 7907-7922; doi:10.3390/molecules15117907
Received: 7 September 2010 / Revised: 18 October 2010 / Accepted: 20 October 2010 / Published: 3 November 2010
Cited by 38 | PDF Full-text (270 KB)
Abstract
Zingiber officinale Roscoe. (Family Zingiberaceae) is well known in Asia. The plant is widely cultivated in village gardens in the tropics for its medicinal properties and as a marketable spice in Malaysia. Ginger varieties are rich in physiologically active phenolics and flavonoids with
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Zingiber officinale Roscoe. (Family Zingiberaceae) is well known in Asia. The plant is widely cultivated in village gardens in the tropics for its medicinal properties and as a marketable spice in Malaysia. Ginger varieties are rich in physiologically active phenolics and flavonoids with a range of pharmacological activities. Experiments were conducted to determine the feasibility of increasing levels of flavonoids (quercetin, rutin, catechin, epicatechin, kaempferol, naringenin, fisetin and morin) and phenolic acid (gallic acid, vanillic acid, ferulic acid, tannic acid, cinnamic acid and salicylic acid), and antioxidant activities in different parts of Malaysian young ginger varieties (Halia Bentong and Halia Bara) with CO2 enrichment in a controlled environment system. Both varieties showed an increase in phenolic compounds and flavonoids in response to CO2 enrichment from 400 to 800 µmol mol-1 CO2. These increases were greater in rhizomes compared to leaves. High performance liquid chromatography (HPLC) results showed that quercetin and gallic acid were the most abundant flavonoid and phenolic acid in Malaysian young ginger varieties. Under elevated CO2 conditions, kaempferol and fisetin were among the flavonoid compounds, and gallic acid and vanillic acid were among the phenolic compounds whose levels increased in both varieties. As CO2 concentration was increased from 400 to 800 µmol mol-1, free radical scavenging power (DPPH) increased about 30% in Halia Bentong and 21.4% in Halia Bara; and the rhizomes exhibited more enhanced free radical scavenging power, with 44.9% in Halia Bentong and 46.2% in Halia Bara. Leaves of both varieties also displayed good levels of flavonoid compounds and antioxidant activities. These results indicate that the yield and pharmaceutical quality of Malaysian young ginger varieties can be enhanced by controlled environment production and CO2 enrichment. Full article
Open AccessArticle Optimizing Ultrasonic Ellagic Acid Extraction Conditions from Infructescence of Platycarya strobilacea Using Response Surface Methodology
Molecules 2010, 15(11), 7923-7932; doi:10.3390/molecules15117923
Received: 30 September 2010 / Revised: 1 October 2010 / Accepted: 3 November 2010 / Published: 4 November 2010
Cited by 8 | PDF Full-text (411 KB)
Abstract
The infructescence of Platycarya strobilacea is a rich source of ellagic acid (EA) which has shown antioxidant, anticancer and antimutagen properties. Response surface methodology (RSM) was used to optimize the conditions for ultrasonic extraction of EA from infructescence of P. strobilacea. A
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The infructescence of Platycarya strobilacea is a rich source of ellagic acid (EA) which has shown antioxidant, anticancer and antimutagen properties. Response surface methodology (RSM) was used to optimize the conditions for ultrasonic extraction of EA from infructescence of P. strobilacea. A central composite design (CCD) was used for experimental design and analysis of the results to obtain the optimal processing parameters. The content of EA in the extracts was determined by HPLC with UV detection. Three independent variables such as ultrasonic extraction temperature (°C), liquid:solid ratio (mL/g), and ultrasonic extraction time (min) were investigated. The experimental data obtained were fitted to a quadratic equation using multiple regression analysis and also analyzed by appropriate statistical methods. The 3-D response surface and the contour plots derived from the mathematical models were applied to determine the optimal conditions. The optimum ultrasonic extraction conditions were as follows: ultrasonic extraction temperature 70 °C, liquid:solid ratio 22.5, and ultrasonic extraction time 40 min. Under these conditions, the experimental percentage value was 1.961%, which is in close agreement with the value predicted by the model. Full article
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Open AccessArticle Flavonoids from Halostachys caspica and Their Antimicrobial and Antioxidant Activities
Molecules 2010, 15(11), 7933-7945; doi:10.3390/molecules15117933
Received: 11 October 2010 / Revised: 2 November 2010 / Accepted: 4 November 2010 / Published: 5 November 2010
Cited by 42 | PDF Full-text (223 KB)
Abstract
Seven flavonoids have been isolated from the aerial parts of Halostachys caspica C. A. Mey. (Chenopodiaceae) for the first time. By means of physicochemical and spectrometric analysis, they were identified as luteolin (1), chrysin (2), chrysin 7-O-β-D-glucopyranoside
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Seven flavonoids have been isolated from the aerial parts of Halostachys caspica C. A. Mey. (Chenopodiaceae) for the first time. By means of physicochemical and spectrometric analysis, they were identified as luteolin (1), chrysin (2), chrysin 7-O-β-D-glucopyranoside (3), quercetin (4), quercetin 3-O-β-D-glucopyranoside (5), isorhamentin-3-O-β-D-glucopyranoside (6), and isorhamentin-3-O-β-D-rutinoside (7). All flavonoids were evaluated to show a broad antimicrobial spectrum of activity on microorganisms including seven bacterial and one fungal species as well as pronounced antioxidant activity. Among them, the aglycones with relatively low polarity had stronger bioactivity than their glycosides. The results suggested that the isolated flavonoids could be used for future development of antimicrobial and antioxidant agents, and also provided additional data for supporting the use of H. caspica as forage. Full article
(This article belongs to the Special Issue Phenolics and Polyphenolics)
Open AccessArticle Oxidative Decarboxylation of Levulinic Acid by Cupric Oxides
Molecules 2010, 15(11), 7946-7960; doi:10.3390/molecules15117946
Received: 8 October 2010 / Revised: 31 October 2010 / Accepted: 4 November 2010 / Published: 5 November 2010
Cited by 14 | PDF Full-text (361 KB)
Abstract
In this paper, cupric oxides was found to effectively oxidize levulinic acid (LA) and lead to the decarboxylation of levulinic acid to 2-butanone. The effects of cupric oxide dosage, reaction time and initial pH value were investigated in batch experiments and a plausible
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In this paper, cupric oxides was found to effectively oxidize levulinic acid (LA) and lead to the decarboxylation of levulinic acid to 2-butanone. The effects of cupric oxide dosage, reaction time and initial pH value were investigated in batch experiments and a plausible mechanism was proposed. The results showed that LA decarboxylation over cupric oxides at around 300 °C under acidic conditions produced the highest yield of butanone (67.5%). In order to elucidate the catalytic activity of cupric oxides, XRD, AFM, XPS and H2-TPR techniques was applied to examine their molecular surfaces and their effects on the reaction process. Full article
Open AccessArticle Antimicrobial Metabolites from the Endophytic Fungus Pichia guilliermondii Isolated from Paris polyphylla var. yunnanensis
Molecules 2010, 15(11), 7961-7970; doi:10.3390/molecules15117961
Received: 11 October 2010 / Revised: 3 November 2010 / Accepted: 4 November 2010 / Published: 5 November 2010
Cited by 47 | PDF Full-text (216 KB)
Abstract
Three steroids and one nordammarane triterpenoid were isolated for the first time from the endophytic fungus Pichia guilliermondii Ppf9 derived from the medicinal plant Paris polyphylla var. yunnanensis. By means of physicochemical and spectrometric analysis, they were identified as ergosta-5,7,22-trienol (1
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Three steroids and one nordammarane triterpenoid were isolated for the first time from the endophytic fungus Pichia guilliermondii Ppf9 derived from the medicinal plant Paris polyphylla var. yunnanensis. By means of physicochemical and spectrometric analysis, they were identified as ergosta-5,7,22-trienol (1), 5α,8α-epidioxyergosta-6,22-dien-3β-ol (2), ergosta-7,22-dien-3β,5α,6β-triol (3), and helvolic acid (4). Both micro-dilution-colorimetric and spore germination assays were employed to evaluate their antimicrobial activity. Among them, helvolic acid (4) exhibited the strongest antibacterial activity against all test bacteria, with MIC values ranging from 1.56 µg/mL to 50 µg/mL, and IC50 values from 0.98 µg/mL to 33.19 µg/mL. It also showed strong inhibitory activity on the spore germination of Magnaporthe oryzae with an IC50 value of 7.20 µg/mL. Among the three steroids, 5α,8α-epidioxyergosta-6,22-dien-3β-ol (2) exhibited relatively strong antimicrobial activity. The results suggest that the endophytic fungus Pichia guillermondii Ppf9 could be a candidate for producing helvolic acid, and the metabolites from this fungus could be potentially developed as antimicrobial agents in the future. Full article
Open AccessArticle Structural Necessity of Indole C5-O-Substitution of seco-Duocarmycin Analogs for Their Cytotoxic Activity
Molecules 2010, 15(11), 7971-7984; doi:10.3390/molecules15117971
Received: 28 September 2010 / Revised: 24 October 2010 / Accepted: 28 October 2010 / Published: 8 November 2010
PDF Full-text (226 KB)
Abstract
A series of racemic indole C5-O-substituted seco-cyclopropylindole (seco-CI) compounds 1-5 were prepared by coupling in the presence of EDCI of 1-(tert-butyloxycarbonyl)-3-(chloromethyl)indoline (seg-A) with 5-hydroxy-, 5-O-methylsulfonyl, 5-O-aminosulfonyl, 5-O-(N,N
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A series of racemic indole C5-O-substituted seco-cyclopropylindole (seco-CI) compounds 1-5 were prepared by coupling in the presence of EDCI of 1-(tert-butyloxycarbonyl)-3-(chloromethyl)indoline (seg-A) with 5-hydroxy-, 5-O-methylsulfonyl, 5-O-aminosulfonyl, 5-O-(N,N-dimethylaminosulfonyl)- and 5-O-benzyl-1H-indole-2-carboxylic acid as seg-B. Compounds 1-5 were tested for cytotoxic activity against four human cancer cell lines (COLO 205, SK-MEL-2, A549, and JEG-3) using a MTT assay. Compounds 2 and 3 with small sized sulfonyl substituents like 5-O-methylsulfonyl and 5-O-aminosulfonyl exhibit a similar level of activity as doxorubicin against all cell lines tested. Full article
Open AccessCommunication Synthesis, Characterization and Pharmacological Evaluation of 1-(2-Chloro-6-Fluorophenyl)-5-Methylindolin-2-One: A New Anti-Inflammatory Compound with Reduced Gastric Ulceration Properties
Molecules 2010, 15(11), 8039-8047; doi:10.3390/molecules15118039
Received: 25 September 2010 / Revised: 3 November 2010 / Accepted: 5 November 2010 / Published: 8 November 2010
Cited by 2 | PDF Full-text (174 KB)
Abstract
The new compound 1-(2-chloro-6-fluorophenyl)-5-methylindolin-2-one (1), designed using the prodrug approach, was easily obtained in 85% yield and characterized by nuclear magnetic resonance, elemental analysis, mass spectrometry and infrared spectroscopy. The lactam 1 showed anti-inflammatory and analgesic activity comparable to that of
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The new compound 1-(2-chloro-6-fluorophenyl)-5-methylindolin-2-one (1), designed using the prodrug approach, was easily obtained in 85% yield and characterized by nuclear magnetic resonance, elemental analysis, mass spectrometry and infrared spectroscopy. The lactam 1 showed anti-inflammatory and analgesic activity comparable to that of the COX-2 inhibitor lumiracoxib, without gastro-ulceration effects. Stability studies demonstrated that the lactam function was stable and did not hydrolyze in pH 1.2 or 7.4. Furthermore, using a thioglycollate-induced peritonitis model, compound 1 was shown to inhibit cell migration by 50.4%, while lumiracoxib inhibited it by 18%. This compound represents a new non-ulcerogenic prototype for the treatment of chronic inflammatory diseases. Full article
Open AccessArticle The Apoptotic Effect of 1’S-1’-Acetoxychavicol Acetate from Alpinia Conchigera on Human Cancer Cells
Molecules 2010, 15(11), 8048-8059; doi:10.3390/molecules15118048
Received: 18 September 2010 / Revised: 8 October 2010 / Accepted: 16 October 2010 / Published: 9 November 2010
Cited by 18 | PDF Full-text (360 KB)
Abstract
1’-(S)-1’-Acetoxychavicol acetate (ACA) isolated from the Malaysian ethno-medicinal plant Alpinia conchigera Griff. was investigated for its potential as an anticancer drug. In this communication, we describe the cytotoxic and apoptotic properties of ACA on five human tumour cell lines. Data from
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1’-(S)-1’-Acetoxychavicol acetate (ACA) isolated from the Malaysian ethno-medicinal plant Alpinia conchigera Griff. was investigated for its potential as an anticancer drug. In this communication, we describe the cytotoxic and apoptotic properties of ACA on five human tumour cell lines. Data from MTT cell viability assays indicated that ACA induced both time- and dose-dependent cytotoxicity on all tumour cell lines tested and had no adverse cytotoxic effects on normal cells. Total mortality of the entire tumour cell population was achieved within 30 hrs when treated with ACA at 40.0 µM concentration. Flow cytometric analysis for annexin-V and PI dual staining demonstrated that cell death occurred via apoptosis, followed by secondary necrosis. The apoptotic effects of ACA were confirmed via the DNA fragmentation assay, in which consistent laddering of genomic DNA was observed for all tumour cell lines after a 24 hrs post-treatment period at the IC50 concentration of ACA. A cell cycle analysis using PI staining also demonstrated that ACA induced cell cycle arrest at the G0/G1 phase, corresponding to oral tumour cell lines. In conclusion, ACA exhibits enormous potential for future development as a chemotherapeutic drug against various malignancies. Full article
(This article belongs to the Section Medicinal Chemistry)
Open AccessArticle Chemopreventive Effects of Peucedanum praeruptorum DUNN and Its Major Constituents on SGC7901 Gastric Cancer Cells
Molecules 2010, 15(11), 8060-8071; doi:10.3390/molecules15118060
Received: 6 October 2010 / Revised: 1 November 2010 / Accepted: 3 November 2010 / Published: 9 November 2010
Cited by 18 | PDF Full-text (206 KB)
Abstract
In this study, the effects of Peucedanum praeruptorum DUNN methanolic extract (PPME) and its major constituents on SGC7901 human gastric cancer cells were evaluated. Two pyranocoumarins, namely, (±) praeruptorin A (PA) and (±) praeruptorin B (PB), were isolated from PPME. A high performance
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In this study, the effects of Peucedanum praeruptorum DUNN methanolic extract (PPME) and its major constituents on SGC7901 human gastric cancer cells were evaluated. Two pyranocoumarins, namely, (±) praeruptorin A (PA) and (±) praeruptorin B (PB), were isolated from PPME. A high performance liquid chromatographic (HPLC) method was developed to determine the contents of PA and PB in PPME. The antiproliferative and cytotoxic actions of PPME were observed using the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) and release of lactate dehydrogenase (LDH) assays. At 300 µg/mL, PPME inhibited cell growth by 51.2% (P < 0.01), probably linked to the high concentration of PA and PB. Both PA and PB exhibited antiproliferative and cytotoxic activities on the SGC7901 cells. Furthermore, the active principle compound, PA, also enhanced the actions of doxorubincin (DOX) on SGC7901 cells. Cell growth decreased higher with the combined treatment of PA and DOX than that with the chemotherapy agent applied alone, suggesting that PA could reduce the dose of DOX for the desired effects. Full article
Open AccessCommunication Antifouling Activity of Simple Synthetic Diterpenoids against Larvae of the Barnacle Balanus albicostatus Pilsbry
Molecules 2010, 15(11), 8072-8081; doi:10.3390/molecules15118072
Received: 14 October 2010 / Revised: 3 November 2010 / Accepted: 8 November 2010 / Published: 9 November 2010
Cited by 8 | PDF Full-text (175 KB)
Abstract
Five new pimarane diterpenoids 1-5 were synthesized using ent-8(14)-pimarene-15R,16-diol as starting material. The structures were elucidated by means of extensive NMR and MS analysis. The antifouling activity against larval settlement of the barnacle Balanus albicostatus were evaluated using capsaicin as a positive
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Five new pimarane diterpenoids 1-5 were synthesized using ent-8(14)-pimarene-15R,16-diol as starting material. The structures were elucidated by means of extensive NMR and MS analysis. The antifouling activity against larval settlement of the barnacle Balanus albicostatus were evaluated using capsaicin as a positive control. Compounds 1-3 and 5 showed more potent antifouling activity than capsaicin. Compound 5, which exhibited almost the same antifouling activity as starting material, showed better stability than starting material. These compounds all showed antifouling activity in a non-toxic way against larval settlement of the barnacle B. albicostatus. Analysis of structure-activity relationships (SAR) demonstrated that the substituents on the C-15 and C-16 position of pimarane diterpenoid were responsible for the antifouling activity. Full article
Open AccessArticle Synthesis of Non-Cytotoxic Poly(Ester-Amine) Dendrimers as Potential Solubility Enhancers for Drugs: Methotrexate as a Case Study
Molecules 2010, 15(11), 8082-8097; doi:10.3390/molecules15118082
Received: 8 October 2010 / Revised: 20 October 2010 / Accepted: 4 November 2010 / Published: 9 November 2010
Cited by 8 | PDF Full-text (500 KB) | Supplementary Files
Abstract
This study describes the synthesis of two new families of dendrimers based on the esterification of N-alkylated 3-amine-1-propanol with two different cores, adipic acid (1st and 2nd generations) and ethylenediamine (generation 1.5), both with carboxylic acid end groups, offering a
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This study describes the synthesis of two new families of dendrimers based on the esterification of N-alkylated 3-amine-1-propanol with two different cores, adipic acid (1st and 2nd generations) and ethylenediamine (generation 1.5), both with carboxylic acid end groups, offering a wide variety of further modifications at the periphery. According to the cytotoxic evaluation of the dendrimers and their possible degradation products within cell lines, these materials could be considered as innocuous. In preliminary studies, the synthesized dendrimers proved to be potential enhancers of solubility of highly hydrophobic drugs, like methotrexate, widely used in chemotherapy. Full article
(This article belongs to the Section Organic Synthesis)
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Open AccessArticle Acute Oral Toxicity and Brine Shrimp Lethality of Elaeis guineensis Jacq., (Oil Palm Leaf) Methanol Extract
Molecules 2010, 15(11), 8111-8121; doi:10.3390/molecules15118111
Received: 2 September 2010 / Revised: 19 September 2010 / Accepted: 12 October 2010 / Published: 10 November 2010
Cited by 15 | PDF Full-text (838 KB)
Abstract
Elaeis guineensis (Arecaceae) is widely used in West African traditional medicine for treating various ailments. An evaluation on the toxicity of extracts of this plant is crucial to support the therapeutic claims. The acute oral toxicity and brine shrimp lethality of a methanolic
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Elaeis guineensis (Arecaceae) is widely used in West African traditional medicine for treating various ailments. An evaluation on the toxicity of extracts of this plant is crucial to support the therapeutic claims. The acute oral toxicity and brine shrimp lethality of a methanolic extract of this plant was tested. Oral administration of crude extract at the highest dose of 5,000 mg/kg resulted in no mortalities or evidence of adverse effects, implying that E. guineensis is nontoxic. Normal behavioral pattern, clinical signs and histology of vital organs confirm this evidence. The E. guineensis extracts screened for toxicity against brine shrimp had 50% lethal concentration (LC50) values of more than 1.0 mg/mL (9.00 and 3.87 mg/mL, at 6 and 24 h, respectively), confirming that the extract was not toxic. Maximum mortalities occurred at 100 mg/mL concentration while the least mortalities happened to be at 0.195 mg/mL concentration. The results of both tests confirm that E. guineensis is nontoxic and hence safe for commercial utilization. Full article
(This article belongs to the Section Natural Products)
Open AccessArticle Investigating the Spectrum of Biological Activity of Ring-Substituted Salicylanilides and Carbamoylphenylcarbamates
Molecules 2010, 15(11), 8122-8142; doi:10.3390/molecules15118122
Received: 13 August 2010 / Revised: 5 November 2010 / Accepted: 9 November 2010 / Published: 10 November 2010
Cited by 21 | PDF Full-text (216 KB)
Abstract
In this study, a series of twelve ring-substituted salicylanilides and carbamoylphenylcarbamates were prepared and characterized. The compounds were analyzed using RP-HPLC to determine lipophilicity. They were tested for their activity related to the inhibition of photosynthetic electron transport (PET) in spinach (Spinacia
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In this study, a series of twelve ring-substituted salicylanilides and carbamoylphenylcarbamates were prepared and characterized. The compounds were analyzed using RP-HPLC to determine lipophilicity. They were tested for their activity related to the inhibition of photosynthetic electron transport (PET) in spinach (Spinacia oleracea L.) chloroplasts. Moreover, their site of action in the photosynthetic apparatus was determined. Primary in vitro screening of the synthesized compounds was also performed against mycobacterial, bacterial and fungal strains. Several compounds showed biological activity comparable with or higher than the standards 3-(3,4-dichlorophenyl)-1,1-dimethylurea, isoniazid, penicillin G, ciprofloxacin or fluconazole. The most active compounds showed minimal anti-proliferative activity against human cells in culture, indicating they would have low cytotoxicity. For all compounds, the relationships between lipophilicity and the chemical structure are discussed. Full article
Open AccessArticle 2-Chlorophenyl Zinc Bromide: A Convenient Nucleophile for the Mannich-Related Multicomponent Synthesis of Clopidogrel and Ticlopidine
Molecules 2010, 15(11), 8144-8155; doi:10.3390/molecules15118144
Received: 8 October 2010 / Revised: 2 November 2010 / Accepted: 9 November 2010 / Published: 11 November 2010
Cited by 8 | PDF Full-text (155 KB)
Abstract
A methodological study devoted to the Mannich-like multicomponent synthesis of the antiplatelet agent (±)‑clopidogrel (7) and the ethyl ester analogue 6 is described. The process involves the formation of 2-chlorophenyl zinc bromide (2) and its subsequent reaction with an alkyl glyoxylate
[...] Read more.
A methodological study devoted to the Mannich-like multicomponent synthesis of the antiplatelet agent (±)‑clopidogrel (7) and the ethyl ester analogue 6 is described. The process involves the formation of 2-chlorophenyl zinc bromide (2) and its subsequent reaction with an alkyl glyoxylate and 4,5,6,7-tetrahydrothieno[3,2-c]pyridine (3). We demonstrate that the organozinc reagent 2 also constitutes a very convenient nucleophile for the multicomponent synthesis of the benzylamine core of ticlopidine (9). Full article
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Open AccessArticle Oligomerization of 3,5-Dimethyl Benzyl Alcohol Promoted by Clay: Experimental and Theoretical Study
Molecules 2010, 15(11), 8156-8168; doi:10.3390/molecules15118156
Received: 8 August 2010 / Revised: 22 October 2010 / Accepted: 27 October 2010 / Published: 11 November 2010
Cited by 7 | PDF Full-text (1156 KB)
Abstract
Linear oligomerization of 3,5-dimethyl benzyl alcohol is induced by a montmorillonite clay (Tonsil Optimum Extra), producing 1,3,5,7-tetramethyl-9,10-dihydro-anthracene, which, by loss of protons results in the product 1,3,5,7-tetramethylanthracene. It was also found that the compounds 4-(3´,5´-dimethylbenzyl)-1,3,5,7-tetramethyl-9,10-dihydroanthracece and 4-(3´,5´-dimethylbenzyl)-1,3,5,7-tetra-methylanthracene were formed from 1,3,5,7-tetramethyl-9,10-dihydroanthracene. 1,3,5,7-Tetramethylanthryl radical
[...] Read more.
Linear oligomerization of 3,5-dimethyl benzyl alcohol is induced by a montmorillonite clay (Tonsil Optimum Extra), producing 1,3,5,7-tetramethyl-9,10-dihydro-anthracene, which, by loss of protons results in the product 1,3,5,7-tetramethylanthracene. It was also found that the compounds 4-(3´,5´-dimethylbenzyl)-1,3,5,7-tetramethyl-9,10-dihydroanthracece and 4-(3´,5´-dimethylbenzyl)-1,3,5,7-tetra-methylanthracene were formed from 1,3,5,7-tetramethyl-9,10-dihydroanthracene. 1,3,5,7-Tetramethylanthryl radical cation was formed from 1,3,5,7-tetramethyl-9,10-dihydroanthracene; it was characterized by Electronic Paramagnetic Resonance (EPR). On the other hand, a theoretical analysis was performed, allowing the rationalization of the observed products and some of the key reaction steps. Full article
(This article belongs to the Section Organic Synthesis)
Open AccessArticle 5,6-Didehydroginsenosides from the Roots of Panax notoginseng
Molecules 2010, 15(11), 8169-8176; doi:10.3390/molecules15118169
Received: 3 November 2010 / Revised: 8 November 2010 / Accepted: 10 November 2010 / Published: 11 November 2010
Cited by 14 | PDF Full-text (219 KB)
Abstract Two minor novel dammarane-type saponins—5,6-didehydroginsenoside Rd (1) and 5,6-didehydroginsenoside Rb1 (2)—were isolated from the dried roots of Panax notoginseng along with sixteen known saponins. The structures of the new compounds were elucidated on the basis of spectroscopic and chemical methods. Full article
Open AccessArticle Analysis of Protein Pathway Networks Using Hybrid Properties
Molecules 2010, 15(11), 8177-8192; doi:10.3390/molecules15118177
Received: 5 August 2010 / Revised: 11 November 2010 / Accepted: 12 November 2010 / Published: 12 November 2010
Cited by 45 | PDF Full-text (188 KB) | Supplementary Files
Abstract
Given a protein-forming system, i.e., a system consisting of certain number of different proteins, can it form a biologically meaningful pathway? This is a fundamental problem in systems biology and proteomics. During the past decade, a vast amount of information on different
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Given a protein-forming system, i.e., a system consisting of certain number of different proteins, can it form a biologically meaningful pathway? This is a fundamental problem in systems biology and proteomics. During the past decade, a vast amount of information on different organisms, at both the genetic and metabolic levels, has been accumulated and systematically stored in various specific databases, such as KEGG, ENZYME, BRENDA, EcoCyc and MetaCyc. These data have made it feasible to address such an essential problem. In this paper, we have analyzed known regulatory pathways in humans by extracting different (biological and graphic) features from each of the 17,069 protein-formed systems, of which 169 are positive pathways, i.e., known regulatory pathways taken from KEGG; while 16,900 were negative, i.e., not formed as a biologically meaningful pathway. Each of these protein-forming systems was represented by 352 features, of which 88 are graph features and 264 biological features. To analyze these features, the “Minimum Redundancy Maximum Relevance” and the “Incremental Feature Selection” techniques were utilized to select a set of 22 optimal features to query whether a protein-forming system is able to form a biologically meaningful pathway or not. It was found through cross-validation that the overall success rate thus obtained in identifying the positive pathways was 79.88%. It is anticipated that, this novel approach and encouraging result, although preliminary yet, may stimulate extensive investigations into this important topic. Full article
(This article belongs to the Special Issue From Computational Chemistry to Complex Networks)
Open AccessArticle Chemical Constituents of the Bark of Dipteryx alata Vogel, an Active Species against Bothrops jararacussu Venom
Molecules 2010, 15(11), 8193-8204; doi:10.3390/molecules15118193
Received: 25 September 2010 / Revised: 4 November 2010 / Accepted: 10 November 2010 / Published: 12 November 2010
Cited by 23 | PDF Full-text (126 KB)
Abstract
The effect of four sub-extracts prepared from the lyophilized hydroalcoholic bark of Dipteryx alata (Leguminosae-Papilionoideae) dissolved in a methanol-water (80:20) mixture through a liquid-liquid partition procedure has been investigated against the neuromuscular blockade of the venom of the snake Bothrops jararacussu. The
[...] Read more.
The effect of four sub-extracts prepared from the lyophilized hydroalcoholic bark of Dipteryx alata (Leguminosae-Papilionoideae) dissolved in a methanol-water (80:20) mixture through a liquid-liquid partition procedure has been investigated against the neuromuscular blockade of the venom of the snake Bothrops jararacussu. The active CH2Cl2 sub-extract has been extensively analyzed for its chemical constituents, resulting in the isolation of four lupane-type triterpenoids: lupeol (1), lupenone (2), 28-hydroxylup-20(29)-en-3-one (3), betulin (4), nine isoflavonoids: 8-O-methylretusin (5), 7-hydroxy-5,6,4’-trimethoxyisoflavone (6), afrormosin (8), 7-hydroxy-8,3’,4’-trimethoxyisoflavone (9), 7,3’-dihydroxy-8,4’-dimethoxyisoflavone (10), odoratin (11), 7,8,3’-trihydroxy-4’-methoxyisoflavone (13), 7,8,3’-trihydroxy-6,4’-dimethoxyisoflavone (15), dipteryxin (17), one chalcone: isoliquiritigenin (7), one aurone: sulfuretin (14) and three phenolic compounds: vanillic acid (12), vanillin (16), and protocatechuic acid (18). Their chemical structures were elucidated on the basis of spectroscopic analysis, including HRMS, 1D- and 2D-NMR techniques. Full article
(This article belongs to the Section Natural Products)
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Open AccessArticle A Highly Efficient Bismuth Salts-Catalyzed Route for the Synthesis of α-Aminophosphonates
Molecules 2010, 15(11), 8205-8213; doi:10.3390/molecules15118205
Received: 24 September 2010 / Revised: 5 October 2010 / Accepted: 9 November 2010 / Published: 12 November 2010
Cited by 20 | PDF Full-text (267 KB)
Abstract A convenient synthesis of different types of α-amino phosphonates via one-pot solvent-free three component reactions of aldehydes, amines and phosphites catalyzed by bismuth salts has been investigated. Bismuth triflate is found to be the most effective catalyst for this reaction. Full article
(This article belongs to the Special Issue Organobismuth Chemistry)
Open AccessArticle Crucial Role of Selenium in the Virucidal Activity of Benzisoselenazol-3(2H)-ones and Related Diselenides
Molecules 2010, 15(11), 8214-8228; doi:10.3390/molecules15118214
Received: 29 October 2010 / Revised: 5 November 2010 / Accepted: 9 November 2010 / Published: 12 November 2010
Cited by 15 | PDF Full-text (223 KB)
Abstract
Various N-substituted benzisoselenazol-3(2H)-ones and their non-selenium-containing analogues have been synthesized and tested against selected viruses (HHV-1, EMCV and VSV) to determine the extent to which selenium plays a role in antiviral activity. The data presented here show that the presence
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Various N-substituted benzisoselenazol-3(2H)-ones and their non-selenium-containing analogues have been synthesized and tested against selected viruses (HHV-1, EMCV and VSV) to determine the extent to which selenium plays a role in antiviral activity. The data presented here show that the presence of selenium is crucial for the antiviral properties of benzisoselenazol-3(2H)-ones since their isostructural analogues having different groups but lacking selenium either did not show any antiviral activity or their activity was substantially lower. The open-chain analogues of benzisoselenazol-3(2H)-ones—diselenides also exhibited high antiviral activity while selenides and disulfides were completely inactive towards model viruses. Full article
(This article belongs to the Special Issue Antivirals)
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Open AccessCommunication Study on Suitability of KOD DNA Polymerase for Enzymatic Production of Artificial Nucleic Acids Using Base/Sugar Modified Nucleoside Triphosphates
Molecules 2010, 15(11), 8229-8240; doi:10.3390/molecules15118229
Received: 30 September 2010 / Revised: 6 November 2010 / Accepted: 10 November 2010 / Published: 12 November 2010
Cited by 14 | PDF Full-text (325 KB)
Abstract
Recently, KOD and its related DNA polymerases have been used for preparing various modified nucleic acids, including not only base-modified nucleic acids, but also sugar-modified ones, such as bridged/locked nucleic acid (BNA/LNA) which would be promising candidates for nucleic acid drugs. However, thus
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Recently, KOD and its related DNA polymerases have been used for preparing various modified nucleic acids, including not only base-modified nucleic acids, but also sugar-modified ones, such as bridged/locked nucleic acid (BNA/LNA) which would be promising candidates for nucleic acid drugs. However, thus far, reasons for the effectiveness of KOD DNA polymerase for such purposes have not been clearly elucidated. Therefore, using mutated KOD DNA polymerases, we studied here their catalytic properties upon enzymatic incorporation of nucleotide analogues with base/sugar modifications. Experimental data indicate that their characteristic kinetic properties enabled incorporation of various modified nucleotides. Among those KOD mutants, one achieved efficient successive incorporation of bridged nucleotides with a 2′-ONHCH2CH2-4′ linkage. In this study, the characteristic kinetic properties of KOD DNA polymerase for modified nucleoside triphosphates were shown, and the effectiveness of genetic engineering in improvement of the enzyme for modified nucleotide polymerization has been demonstrated. Full article
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Open AccessArticle Phenolic Compounds from Merremia umbellata subsp. orientalis and Their Allelopathic Effects on Arabidopsis Seed Germination
Molecules 2010, 15(11), 8241-8250; doi:10.3390/molecules15118241
Received: 15 September 2010 / Revised: 27 October 2010 / Accepted: 29 October 2010 / Published: 12 November 2010
Cited by 11 | PDF Full-text (297 KB)
Abstract
A bioassay-directed phytochemical study was carried out to investigate potential allelochemicals of the invasive plant Merremia umbellata subsp. orientalis (Hall. f.). Eight phenolic compounds, including a salicylic acid (SA)-derived new natural product, SA 2-O-β-D-(3',6'-dicaffeoyl)-glucopyranoside (1), and seven known ones
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A bioassay-directed phytochemical study was carried out to investigate potential allelochemicals of the invasive plant Merremia umbellata subsp. orientalis (Hall. f.). Eight phenolic compounds, including a salicylic acid (SA)-derived new natural product, SA 2-O-β-D-(3',6'-dicaffeoyl)-glucopyranoside (1), and seven known ones 2-8 were isolated and identified from two bioactive sub-fractions of the acetone extract of this plant. The structure of new compound 1 was established by spectral and chemical methods. The potential allelopathic effects of these compounds at 0.5 and 1.0 mM concentrations on the germination of Arabidopsis seeds were tested. Results showed that 2 remarkably inhibited seed germination at concentrations as low as 0.5 mM. Compound 3 only moderately inhibited seed germination at 0.5 mM, but displayed strong inhibitory bioactivity at 1.0 mM concentration. Compounds 4 and 5 showed only slight inhibitory bioactivity at 1.0 mM, while the other compounds showed no obvious inhibitory effects. Full article
(This article belongs to the Section Natural Products)
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Open AccessArticle Pancreatic Lipase Inhibition by C-Glycosidic Flavones Isolated from Eremochloa ophiuroides
Molecules 2010, 15(11), 8251-8259; doi:10.3390/molecules15118251
Received: 2 November 2010 / Revised: 11 November 2010 / Accepted: 12 November 2010 / Published: 16 November 2010
Cited by 33 | PDF Full-text (205 KB)
Abstract
Activity-guided fractionation of a methanolic extract of the leaves of Eremochloa ophiuroides (centipede grass) using a pancreatic lipase inhibitory assay led to the isolation and identification of a new C-glycosidic flavone, luteolin 6-C-b-D-boivinopyranoside (1), as well as eight
[...] Read more.
Activity-guided fractionation of a methanolic extract of the leaves of Eremochloa ophiuroides (centipede grass) using a pancreatic lipase inhibitory assay led to the isolation and identification of a new C-glycosidic flavone, luteolin 6-C-b-D-boivinopyranoside (1), as well as eight known compounds. The structures of these compounds were established on the basis of interpretation of their spectroscopic data. Among these isolates, the C-glycosidic flavones 15 showed potent inhibitory effects on pancreatic lipase, with IC50 values ranging from 18.5 ± 2.6 to 50.5 ± 3.9 mM. Full article
(This article belongs to the collection Bioactive Compounds)
Open AccessArticle MimoDB: a New Repository for Mimotope Data Derived from Phage Display Technology
Molecules 2010, 15(11), 8279-8288; doi:10.3390/molecules15118279
Received: 21 October 2010 / Revised: 4 November 2010 / Accepted: 12 November 2010 / Published: 15 November 2010
Cited by 32 | PDF Full-text (656 KB)
Abstract
Peptides selected from phage-displayed random peptide libraries are valuable in two aspects. On one hand, these peptides are candidates for new diagnostics, therapeutics and vaccines. On the other hand, they can be used to predict the networks or sites of protein-protein interactions. MimoDB,
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Peptides selected from phage-displayed random peptide libraries are valuable in two aspects. On one hand, these peptides are candidates for new diagnostics, therapeutics and vaccines. On the other hand, they can be used to predict the networks or sites of protein-protein interactions. MimoDB, a new repository for these peptides, was developed, in which 10,716 peptides collected from 571 publications were grouped into 1,229 sets. Besides peptide sequences, other important information, such as the target, template, library and complex structure, was also included. MimoDB can be browsed and searched through a user-friendly web interface. For computational biologists, MimoDB can be used to derive customized data sets and benchmarks, which are useful for new algorithm development and tool evaluation. For experimental biologists, their results can be searched against the MimoDB database to exclude possible target-unrelated peptides. The MimoDB database is freely accessible at http://immunet.cn/mimodb/. Full article
(This article belongs to the Special Issue Phage Display of Combinatorial Libraries)
Open AccessArticle Towards the Development of Synthetic Routes Using Theoretical Calculations: An Application of In Silico Screening to 2,6-Dimethylchroman-4-one
Molecules 2010, 15(11), 8289-8304; doi:10.3390/molecules15118289
Received: 17 September 2010 / Revised: 9 November 2010 / Accepted: 11 November 2010 / Published: 15 November 2010
Cited by 4 | PDF Full-text (327 KB)
Abstract
This study describes an attempt to develop a synthetic route using theoretical calculations, i.e., in silico synthesis route development. The KOSP program created four potential synthetic routes for generating 2,6-dimethylchroman-4-one. In silico screening of these four synthetic routes was then performed. In
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This study describes an attempt to develop a synthetic route using theoretical calculations, i.e., in silico synthesis route development. The KOSP program created four potential synthetic routes for generating 2,6-dimethylchroman-4-one. In silico screening of these four synthetic routes was then performed. In silico screening involves theoretical analysis of synthetic routes prior to actual experimental work. A synthetic route using the Mitsunobu reaction had already been reported by Hoddgets et al. Theoretical investigations were also conducted on two SNAr reactions as well as a Michael reaction before they were examined experimentally. In silico screening using DFT calculations indicated that only the Michael reaction was likely to produce the target. Experimental work confirmed that the target was obtained in a yield of 76.4% using the Michael reaction. The other two routes, except for the Mitsunobu reaction, failed to generate the target. Our results demonstrate that theoretical calculations can be used to narrow down the number of experiments that need to be conducted when developing novel synthetic routes. Full article
(This article belongs to the Special Issue From Computational Chemistry to Complex Networks)
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Open AccessArticle Catalytic Asymmetric Synthesis of Both Enantiomers of 4‑Substituted 1,4-Dihydropyridines with the Use of Bifunctional Thiourea-Ammonium Salts Bearing Different Counterions
Molecules 2010, 15(11), 8305-8326; doi:10.3390/molecules15118305
Received: 13 October 2010 / Revised: 8 November 2010 / Accepted: 12 November 2010 / Published: 15 November 2010
Cited by 12 | PDF Full-text (318 KB)
Abstract
Organoammonium salts composed of a Brønsted acid and an anilinothiourea promoted the Michael addition of β-keto esters and α,β-unsaturated aldehydes in the presence of primary amines to give functionalized 1,4-dihydropyridines enantioselectively. With the use of the different Brønsted acids such as DFA and
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Organoammonium salts composed of a Brønsted acid and an anilinothiourea promoted the Michael addition of β-keto esters and α,β-unsaturated aldehydes in the presence of primary amines to give functionalized 1,4-dihydropyridines enantioselectively. With the use of the different Brønsted acids such as DFA and HBF4 with the same bifunctional thiourea, both enantiomers of 4-substituted 1,4-dihydropyridine were synthesized from the same starting materials. Full article
(This article belongs to the Special Issue Bifunctional Catalysis)
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Open AccessArticle Synthesis and Properties of Chiral Thioureas Bearing an Additional Function at a Remote Position Tethered by a 1,5-Disubstituted Triazole
Molecules 2010, 15(11), 8327-8348; doi:10.3390/molecules15118327
Received: 20 October 2010 / Revised: 8 November 2010 / Accepted: 10 November 2010 / Published: 15 November 2010
Cited by 4 | PDF Full-text (250 KB)
Abstract
The synthesis and properties of multifunctional thioureas bearing a variety of functional groups at a position remote from the thiourea moiety are described. A 1,5-disubstituted triazole tether connected with a thiourea and another functional group was synthesized via ruthenium catalyzed Huisgen cycloaddition. We
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The synthesis and properties of multifunctional thioureas bearing a variety of functional groups at a position remote from the thiourea moiety are described. A 1,5-disubstituted triazole tether connected with a thiourea and another functional group was synthesized via ruthenium catalyzed Huisgen cycloaddition. We demonstrate the utility of the synthetic thioureas as asymmetric catalysts and probes for the mechanistic elucidation of the course of the Michael reaction of an α,β-unsaturated imide Full article
(This article belongs to the Special Issue Bifunctional Catalysis)
Open AccessArticle Synthesis, Structures and Properties of Cu(II) and Mn(II) Complexes with 1,10-Phenanthroline-2-carboxylic acid and 2,2’-Bipyridine Ligands
Molecules 2010, 15(11), 8349-8359; doi:10.3390/molecules15118349
Received: 10 September 2010 / Revised: 18 October 2010 / Accepted: 25 October 2010 / Published: 15 November 2010
Cited by 3 | PDF Full-text (456 KB) | Supplementary Files
Abstract
Four new 2,2’-bipyridine and 1,10-phenanthroline complexes, namely [Mn(phenca)2]·(H2O)2 (1), [Cu4(phen)4(OH-)4(H2O)2](DMF)4(ClO4-)4(H2O) (2), [Cu2
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Four new 2,2’-bipyridine and 1,10-phenanthroline complexes, namely [Mn(phenca)2]·(H2O)2 (1), [Cu4(phen)4(OH-)4(H2O)2](DMF)4(ClO4-)4(H2O) (2), [Cu2(2,2-bipy)2(C2O42-)(H2O)2(NO3)2] (3) and [Cu(2,2-bipy)2(ClO4-)](ClO4-) (4) (2,2’-bpy = 2,2’-bipyridine, Hphenca = 1,10-phenanthroline-2-carboxylic acid) have been synthesized by a hydrothermal reaction. The products were characterized by elemental analysis, infrared spectroscopy and X-ray crystal diffraction. While strong hydrogen bonds play central roles in the formation of the 3D structure, the combined influence of the weak interactions such as π···π interactions is also evident in the structures. A preliminary investigation on the ion exchange properties of the complexes is presented. Full article
Open AccessArticle A Novel 18-Norclerodane Diterpenoid from the Roots of Tinospora sagittata var. yunnanensis
Molecules 2010, 15(11), 8360-8365; doi:10.3390/molecules15118360
Received: 10 September 2010 / Revised: 4 November 2010 / Accepted: 10 November 2010 / Published: 16 November 2010
Cited by 7 | PDF Full-text (195 KB)
Abstract
A novel 18-nor-clerodane diterpenoid named sagitone (1) was isolated from the 95% ethanol extract of dry roots of Tinospora sagittata var. yunnanensis together with the five known diterpenoids columbin (2), palmatoside C (3), fibleucin (4),
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A novel 18-nor-clerodane diterpenoid named sagitone (1) was isolated from the 95% ethanol extract of dry roots of Tinospora sagittata var. yunnanensis together with the five known diterpenoids columbin (2), palmatoside C (3), fibleucin (4), tinophylloloside (5) and epitinophylloloside (6). The structure of the new compound 1 was determined based on MS, IR, 1D and 2D NMR spectral data. The compounds 1~6 did not show significant cytotoxic activity against cancer cell lines K562 and HL-60. Full article
(This article belongs to the Section Natural Products)
Open AccessArticle Median Lethal Dose, Antimalarial Activity, Phytochemical Screening and Radical Scavenging of Methanolic Languas galanga Rhizome Extract
Molecules 2010, 15(11), 8366-8376; doi:10.3390/molecules15118366
Received: 29 September 2010 / Revised: 7 November 2010 / Accepted: 11 November 2010 / Published: 16 November 2010
Cited by 11 | PDF Full-text (152 KB) | Supplementary Files
Abstract
The methanolic extract of Languas galanga rhizomes was investigated for antimalarial activity against Plasmodium berghei (NK65) infections in mice. The median lethal dose was determined to ascertain the safety of the extract in ICR mice of both sexes. The antimalarial activities during early
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The methanolic extract of Languas galanga rhizomes was investigated for antimalarial activity against Plasmodium berghei (NK65) infections in mice. The median lethal dose was determined to ascertain the safety of the extract in ICR mice of both sexes. The antimalarial activities during early and established infections, as well as the prophylactic activity were evaluated. Phytochemical screening and radical scavenging activity of the extract were also investigated to elucidate the possible mechanism of the antimalarial properties. The acute oral toxicity (LD50) of Languas galanga extract in mice was established to be 4,998 mg/kg. The extract of Languas galanga rhizomes demonstrated significant antiplasmodial activity in all the three models of the antimalarial evaluations. Phytochemical screening revealed the presence of some vital antiplasmodial constituents such as terpenoids and flavonoids. The extract also exhibited a moderate capacity to scavenge the free radicals. The rhizome extract of Languas galanga thus possesses antimalarial activity, which explains the rational usage of this plant in traditional Malaysian medicine. Full article
Open AccessArticle Anti-Neoplastic Effects of Gallic Acid, a Major Component of Toona sinensis Leaf Extract, on Oral Squamous Carcinoma Cells
Molecules 2010, 15(11), 8377-8389; doi:10.3390/molecules15118377
Received: 2 November 2010 / Revised: 15 November 2010 / Accepted: 16 November 2010 / Published: 16 November 2010
Cited by 45 | PDF Full-text (468 KB)
Abstract
Extract of Toona sinensis (TS) has been reported to have various effects on cultured cell lines, including anti-proliferative activity in cancer cells. We have studied the effects of TS on various human oral squamous carcinoma cell lines (HOSCC), including UM1, UM2,
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Extract of Toona sinensis (TS) has been reported to have various effects on cultured cell lines, including anti-proliferative activity in cancer cells. We have studied the effects of TS on various human oral squamous carcinoma cell lines (HOSCC), including UM1, UM2, SCC-4, and SCC-9. These cell lines were treated with TS leaf extract and screened for viability, apoptosis, necrosis, and apoptotic gene expression. Normal human oral keratinocytes (NHOK) served as a control for cytotoxic assays. Viability of TS-treated HOSCC was reduced, whereas that of NHOK was not affected. FACScan analysis revealed that the leaf extract induced apoptosis or a combination of apoptosis and necrosis, depending on cell type. Microarray and semi-quantitative RT-PCR analysis for apoptotic-related gene expression revealed that 3,4,5-trihydroxybenzoic acid (gallic acid, one of the major bioactive compounds purified from TS extract) up-regulated pro-apoptotic genes such TNF-α, TP53BP2, and GADD45A, and down-regulated the anti-apoptotic genes Survivin and cIAP1, resulting in cell death. This study suggests that gallic acid, the major bioactive compound present, is responsible for the anti-neoplastic effect of Toona sinensis leaf extract. Full article
(This article belongs to the Section Natural Products)
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Open AccessArticle Comparative Analysis of Headspace Volatiles of Chinese Rosa rugosa
Molecules 2010, 15(11), 8390-8399; doi:10.3390/molecules15118390
Received: 21 October 2010 / Revised: 9 November 2010 / Accepted: 11 November 2010 / Published: 16 November 2010
Cited by 13 | PDF Full-text (173 KB)
Abstract
The floral headspace compounds of Chinese Rosa rugosa germplasms that were isolated by an automated headspace sampler with built-in trap, and followed by gas chromatography-mass spectrometry for identification and quantification. Up to 33 volatile compounds were identified from the 23 rose germplasms, including
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The floral headspace compounds of Chinese Rosa rugosa germplasms that were isolated by an automated headspace sampler with built-in trap, and followed by gas chromatography-mass spectrometry for identification and quantification. Up to 33 volatile compounds were identified from the 23 rose germplasms, including nine alcohols, five esters, three alkanes, 10 terpenes, three aldehydes, two ketones, and one ether. The main floral components identified were 2-phenylethanol, β-citronellol, ethanol, and n-hexane. ‘xizi’, ‘miaofengshan’, ‘xiangciguo’, and ‘tangbai’ contained the highest amounts of 2-phenylethanol  at 84.66 μg·g-1, β-citronellol at 70.98 μg·g-1, ethanol at 83.87 μg·g-1, and n-hexane at 18.23 μg·g-1, respectively. ‘Rongchengyesheng’, ‘tanghong’, ‘xizi’, ‘miaofengshan’, and ‘baizizhi’ could be considered good materials for extracting rose oil and breeding new cultivars. Full article
Open AccessArticle Microwave-Assisted Synthesis of Novel 2,3-Dihydro-4-Pyridinones
Molecules 2010, 15(11), 8425-8430; doi:10.3390/molecules15118425
Received: 22 October 2010 / Revised: 9 November 2010 / Accepted: 11 November 2010 / Published: 17 November 2010
Cited by 2 | PDF Full-text (111 KB)
Abstract
Novel 2,3-dihydro-4-pyridinones were synthesized via the reaction of curcumin and primary amines or amine acetates under microwave irradiation. Montmorillonite K-10 was used as a catalyst. Reaction times did not exceed 120 s. The structures of the compounds were established by elemental analysis and
[...] Read more.
Novel 2,3-dihydro-4-pyridinones were synthesized via the reaction of curcumin and primary amines or amine acetates under microwave irradiation. Montmorillonite K-10 was used as a catalyst. Reaction times did not exceed 120 s. The structures of the compounds were established by elemental analysis and from their mass, 1H- and 13C-NMR spectra. Full article
(This article belongs to the Section Organic Synthesis)
Open AccessArticle Antiseptic Activity and Phenolic Constituents of the Aerial Parts of Vitex negundo var. cannabifolia
Molecules 2010, 15(11), 8469-8477; doi:10.3390/molecules15118469
Received: 15 October 2010 / Revised: 11 November 2010 / Accepted: 15 November 2010 / Published: 18 November 2010
Cited by 22 | PDF Full-text (277 KB)
Abstract
Four phenolics, salviaplebeiaside (1), γ-tocopherol (2), chrysosplenol-D (4), and isovitexin (5), along with α-tocoquinone (3) and β-sitosterol (6) were isolated from the aerial parts of Vitex negundo var.
[...] Read more.
Four phenolics, salviaplebeiaside (1), γ-tocopherol (2), chrysosplenol-D (4), and isovitexin (5), along with α-tocoquinone (3) and β-sitosterol (6) were isolated from the aerial parts of Vitex negundo var. cannabifolia. The isolation was performed using bio-assay tracking experiments. The structures of compounds 1-5 were established by spectroscopic means. The antibacterial activities of the compounds were assessed against Escherichia coli, Bacillus subtilis, Micrococcus tetragenus and Pseudomonas fluorescens. Chrysosplenol-D (4) exhibited activities against all the four spoilage microorganisms. Full article
(This article belongs to the Special Issue Phenolics and Polyphenolics)
Open AccessArticle The Pharmacokinetics of Raloxifene and Its Interaction with Apigenin in Rat
Molecules 2010, 15(11), 8478-8487; doi:10.3390/molecules15118478
Received: 25 October 2010 / Revised: 15 November 2010 / Accepted: 16 November 2010 / Published: 18 November 2010
Cited by 7 | PDF Full-text (299 KB)
Abstract
Purpose: Raloxifene is a selective estrogen receptor modulator which is structurally similar to tamoxifen. As flavonoids can interact with raloxifene in vitro, we evaluated the in vivo pharmacokinetics of raloxifene in rats when co-administered with apigenin. Methods: The pharmacokinetics of
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Purpose: Raloxifene is a selective estrogen receptor modulator which is structurally similar to tamoxifen. As flavonoids can interact with raloxifene in vitro, we evaluated the in vivo pharmacokinetics of raloxifene in rats when co-administered with apigenin. Methods: The pharmacokinetics of raloxifene in the absence or presence of apigenin was investigated in rats after different dosage regimens. The plasma concentrations before and after enzymatic hydrolysis were analyzed by HPLC, and the pharmacokinetic profiles of raloxifene administered alone and in combination with apigenin were compared. Results: Co-administration of apigenin with raloxifene in a 1:2 ratio by weight resulted in a 55% and 37% increase in the Cmax and AUC of intact raloxifene, respectively. When equal proportions of raloxifene and apigenin (1:1) were administered, the Cmax and AUC of intact raloxifene were increased by 173% and 97% respectively. This increase in intact raloxifene was not associated with an increase in total raloxifene (intact plus conjugated raloxifene) because AUC and Cmax of total raloxifene when administered alone or in combination with apigenin were found to be similar. The results indicated that apigenin inhibited the glucuronidation and sulfation of raloxifene in the intestine bringing about an increased bioavailability of the drug. Conclusions: The results showed that apigenin decreased the first-pass metabolism of raloxifene but did not increase its absorption from the gastrointestinal tract. Full article
Open AccessArticle Selective Inhibitory Effect of Epigallocatechin-3-gallate on Migration of Vascular Smooth Muscle Cells
Molecules 2010, 15(11), 8488-8500; doi:10.3390/molecules15118488
Received: 31 August 2010 / Revised: 13 November 2010 / Accepted: 17 November 2010 / Published: 19 November 2010
Cited by 6 | PDF Full-text (3374 KB)
Abstract
In order to prevent restenosis after angioplasty or stenting, one of the most popular targets is suppression of the abnormal growth and excess migration of vascular smooth muscle cells (VSMCs) with drugs. However, the drugs also adversely affect vascular endothelial cells (VECs), leading
[...] Read more.
In order to prevent restenosis after angioplasty or stenting, one of the most popular targets is suppression of the abnormal growth and excess migration of vascular smooth muscle cells (VSMCs) with drugs. However, the drugs also adversely affect vascular endothelial cells (VECs), leading to the induction of late thrombosis. We have investigated the effect of epigallocatechin-3-gallate (EGCG) on the proliferation and migration of VECs and VSMCs. Both cells showed dose-dependent decrease of viability in response to EGCG while they have different IC50 values of EGCG (VECs, 150 mM and VSMCs, 1050 mM). Incubating both cells with EGCG resulted in significant reduction in cell proliferation irrespective of cell type. The proliferation of VECs were greater affected than that of VSMCs at the same concentrations of EGCG. EGCG exerted differential migration-inhibitory activity in VECs vs. VSMCs. The migration of VECs was not attenuated by 200 mM EGCG, but that of VSMCs was significantly inhibited at the same concentration of EGCG. It is suggested that that EGCG can be effectively used as an efficient drug for vascular diseases or stents due to its selective activity, completely suppressing the proliferation and migration of VSMCs, but not adversely affecting VECs migration in blood vessels. Full article
(This article belongs to the Special Issue Antioxidants)
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Open AccessCommunication Synthesis of Seco-Chlorinated Derivatives of Phenanthroindolizidine Precursors via Friedel-Crafts Reaction
Molecules 2010, 15(11), 8501-8506; doi:10.3390/molecules15118501
Received: 9 October 2010 / Revised: 14 November 2010 / Accepted: 14 November 2010 / Published: 22 November 2010
PDF Full-text (178 KB)
Abstract In the course of synthesizing 3-demethyltylophorine (1) by Lewis acid catalyzed intramolecular Friedel-Crafts reaction starting from N-(3-hydroxy-2,6,7-trimethoxy-phenanthr-9-ylmethyl)-2-chloromethylpyrrolidine, two chlorinated phenanthrene derivatives N-(4,10-dichloro-3-hydroxy-2,6,7-trimethoxyphenanthr-9-ylmethyl)-2-chloromethylpyrrolidine (4) and N-(4-chloro-3-hydroxy-2,6,7-trimethoxyphenanthr-9-ylmethyl)-2-chloromethylpyrrolidine (5) were obtained. The structures of these compounds were determined by spectroscopic analysis. Full article
Open AccessArticle Antioxidant, Anti-Inflammatory and Anti-Influenza Properties of Components from Chaenomeles speciosa
Molecules 2010, 15(11), 8507-8517; doi:10.3390/molecules15118507
Received: 1 November 2010 / Revised: 15 November 2010 / Accepted: 17 November 2010 / Published: 22 November 2010
Cited by 27 | PDF Full-text (286 KB)
Abstract
The fruit of Chaenomeles speciosa is a traditional Chinese medicine used for the treatment of dyspepsia and various inflammatory diseases. In the present study, we evaluated the potential radical scavenging capacity, and activity against nitrous oxide, inflammatory cytokines production and neuramindase (NA) of
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The fruit of Chaenomeles speciosa is a traditional Chinese medicine used for the treatment of dyspepsia and various inflammatory diseases. In the present study, we evaluated the potential radical scavenging capacity, and activity against nitrous oxide, inflammatory cytokines production and neuramindase (NA) of its isolates. The results showed that 3,4-dihydroxybenzoic acid (1) displayed higher inhibitory activities on DPPH and NA with IC50 values of 1.02 mg/mL and 1.27 mg/mL respectively, and quercetin (2) also showed significant inhibitory action on DPPH and NA, with IC50 values of 3.82 mg/mL and 1.90 mg/mL. Compounds 1, 2 and methyl 3-hydroxybutanedioic ester (3) could inhibit the production of TNF-a by 22.73%, 33.14% and 37.19% at 5 mg/mL (P < 0.05) compared with the control. In addition, compound 2 was found to be active on the release of IL-6 in RAW264.7 macrophage cells, with an inhibitory rate of 39.79% (P < 0.05). The anti-inflammatory effect of compound 3 is disclosed for the first time in this study. Avian influenza is usually accompanied by virus invasion followed by the occurrence of oxidative stress and serious inflammation, so the multiple effects of the isolates may play a cocktail-like role in the treatment of avian influenza, and C. speciosa components, especially quercetin, might be a potent source for anti-viral and anti-inflammatory agents. Full article
(This article belongs to the Special Issue Antioxidants)
Open AccessArticle Characterization of Phosphate Solubilizing Bacteria in Sediments from a Shallow Eutrophic Lake and a Wetland: Isolation, Molecular Identification and Phosphorus Release Ability Determination
Molecules 2010, 15(11), 8518-8533; doi:10.3390/molecules15118518
Received: 12 September 2010 / Revised: 16 November 2010 / Accepted: 17 November 2010 / Published: 22 November 2010
Cited by 16 | PDF Full-text (720 KB)
Abstract
The transformation of phosphorus (P) is a major factor of lake eutrophication, and phosphate releasing bacteria play an important role in the release process. Experiments were conducted to investigate P content and characterize phosphate solubilizing bacterial composition at the molecular level in a
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The transformation of phosphorus (P) is a major factor of lake eutrophication, and phosphate releasing bacteria play an important role in the release process. Experiments were conducted to investigate P content and characterize phosphate solubilizing bacterial composition at the molecular level in a shallow eutrophic lake and a wetland. Results showed that P concentrations were relatively high and derived from agricultural runoff and domestic or industrial pollution. Enumeration and molecular identification of these strains indicated that these bacterial groups were abundant in the ecosystem and various kinds of bacteria participated in the phosphorus release process. Twelve phosphate solubilizing bacteria, including eight organic P-solubilizing bacteria (OPBs) and four inorganic P-solubilizing bacteria (IPBs), which belonged to three different families, were isolated and identified. Cupriavidus basilensis was found for the first time to have the ability to mineralize organic P (OP). Laboratory tests on P release ability revealed that IPBs were more effective at releasing P than OPBs. The most efficient IPB strain could accumulate over 170 mg·L-1 orthophosphate, while the equivalent OPB strain only liberated less than 4 mg·L-1 orthophosphate in liquid culture. The results obtained from this investigation should help clarify the roles of microorganisms in aquatic systems and the mechanisms of eutrophication. Full article

Review

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Open AccessReview The Biosynthesis of Artemisinin (Qinghaosu) and the Phytochemistry of Artemisia annua L. (Qinghao)
Molecules 2010, 15(11), 7603-7698; doi:10.3390/molecules15117603
Received: 13 September 2010 / Accepted: 17 October 2010 / Published: 28 October 2010
Cited by 106 | PDF Full-text (1398 KB)
Abstract
The Chinese medicinal plant Artemisia annua L. (Qinghao) is the only known source of the sesquiterpene artemisinin (Qinghaosu), which is used in the treatment of malaria. Artemisinin is a highly oxygenated sesquiterpene, containing a unique 1,2,4-trioxane ring structure, which is responsible for the
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The Chinese medicinal plant Artemisia annua L. (Qinghao) is the only known source of the sesquiterpene artemisinin (Qinghaosu), which is used in the treatment of malaria. Artemisinin is a highly oxygenated sesquiterpene, containing a unique 1,2,4-trioxane ring structure, which is responsible for the antimalarial activity of this natural product. The phytochemistry of A. annua is dominated by both sesquiterpenoids and flavonoids, as is the case for many other plants in the Asteraceae family. However, A. annua is distinguished from the other members of the family both by the very large number of natural products which have been characterised to date (almost six hundred in total, including around fifty amorphane and cadinane sesquiterpenes), and by the highly oxygenated nature of many of the terpenoidal secondary metabolites. In addition, this species also contains an unusually large number of terpene allylic hydroperoxides and endoperoxides. This observation forms the basis of a proposal that the biogenesis of many of the highly oxygenated terpene metabolites from A. annua – including artemisinin itself – may proceed by spontaneous oxidation reactions of terpene precursors, which involve these highly reactive allyllic hydroperoxides as intermediates. Although several studies of the biosynthesis of artemisinin have been reported in the literature from the 1980s and early 1990s, the collective results from these studies were rather confusing because they implied that an unfeasibly large number of different sesquiterpenes could all function as direct precursors to artemisinin (and some of the experiments also appeared to contradict one another). As a result, the complete biosynthetic pathway to artemisinin could not be stated conclusively at the time. Fortunately, studies which have been published in the last decade are now providing a clearer picture of the biosynthetic pathways in A. annua. By synthesising some of the sesquiterpene natural products which have been proposed as biogenetic precursors to artemisinin in such a way that they incorporate a stable isotopic label, and then feeding these precursors to intact A. annua plants, it has now been possible to demonstrate that dihydroartemisinic acid is a late-stage precursor to artemisinin and that the closely related secondary metabolite, artemisinic acid, is not (this approach differs from all the previous studies, which used radio-isotopically labelled precursors that were fed to a plant homogenate or a cell-free preparation). Quite remarkably, feeding experiments with labeled dihydroartemisinic acid and artemisinic acid have resulted in incorporation of label into roughly half of all the amorphane and cadinane sesquiterpenes which were already known from phytochemical studies of A. annua. These findings strongly support the hypothesis that many of the highly oxygenated sesquiterpenoids from this species arise by oxidation reactions involving allylic hydroperoxides, which seem to be such a defining feature of the chemistry of A. annua. In the particular case of artemisinin, these in vivo results are also supported by in vitro studies, demonstrating explicitly that the biosynthesis of artemisinin proceeds via the tertiary allylic hydroperoxide, which is derived from oxidation of dihydroartemisinic acid. There is some evidence that the autoxidation of dihydroartemisinic acid to this tertiary allylic hydroperoxide is a non-enzymatic process within the plant, requiring only the presence of light; and, furthermore, that the series of spontaneous rearrangement reactions which then convert this allylic hydroperoxide to the 1,2,4-trioxane ring of artemisinin are  also non-enzymatic in nature. Full article
Open AccessReview Nutraceutical Antioxidants as Novel Neuroprotective Agents
Molecules 2010, 15(11), 7792-7814; doi:10.3390/molecules15117792
Received: 15 October 2010 / Accepted: 20 October 2010 / Published: 3 November 2010
Cited by 181 | PDF Full-text (1781 KB)
Abstract
A variety of antioxidant compounds derived from natural products (nutraceuticals) have demonstrated neuroprotective activity in either in vitro or in vivo models of neuronal cell death or neurodegeneration, respectively. These natural antioxidants fall into several distinct groups based on their chemical structures: (1)
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A variety of antioxidant compounds derived from natural products (nutraceuticals) have demonstrated neuroprotective activity in either in vitro or in vivo models of neuronal cell death or neurodegeneration, respectively. These natural antioxidants fall into several distinct groups based on their chemical structures: (1) flavonoid polyphenols like epigallocatechin 3-gallate (EGCG) from green tea and quercetin from apples; (2) non-flavonoid polyphenols such as curcumin from tumeric and resveratrol from grapes; (3) phenolic acids or phenolic diterpenes such as rosmarinic acid or carnosic acid, respectively, both from rosemary; and (4) organosulfur compounds including the isothiocyanate, L-sulforaphane, from broccoli and the thiosulfonate allicin, from garlic. All of these compounds are generally considered to be antioxidants. They may be classified this way either because they directly scavenge free radicals or they indirectly increase endogenous cellular antioxidant defenses, for example, via activation of the nuclear factor erythroid-derived 2-related factor 2 (Nrf2) transcription factor pathway. Alternative mechanisms of action have also been suggested for the neuroprotective effects of these compounds such as modulation of signal transduction cascades or effects on gene expression. Here, we review the literature pertaining to these various classes of nutraceutical antioxidants and discuss their potential therapeutic value in neurodegenerative diseases. Full article
(This article belongs to the Special Issue Neuroprotective Strategies)
Open AccessReview Herba Epimedii: Anti-Oxidative Properties and Its Medical Implications
Molecules 2010, 15(11), 7861-7870; doi:10.3390/molecules15117861
Received: 11 August 2010 / Accepted: 2 November 2010 / Published: 3 November 2010
Cited by 30 | PDF Full-text (614 KB)
Abstract
Herba Epimedii is a Chinese herbal medicine with proven efficacy in treating cardiovascular diseases and osteoporosis, and in improving sexual and neurological functions. This efficacy is found to be related to the potent anti-oxidative ability of Herba Epimedii and its flavonoid components, with
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Herba Epimedii is a Chinese herbal medicine with proven efficacy in treating cardiovascular diseases and osteoporosis, and in improving sexual and neurological functions. This efficacy is found to be related to the potent anti-oxidative ability of Herba Epimedii and its flavonoid components, with icarrin as the main effective constituent, along with polysaccharides and vitamin C. These ingredients have been proven to be effective against oxidative-stress related pathologies (cardiovascular diseases, Alzheimer’s disease and inflammation) in animal rodent models and in vitro studies. Their anti-oxidative properties are found to be related to an inductive effect on endogenous free-radical scavenging enzymes such as catalase and glutathione peroxidase and the inherent electron-donating ability of flavonoids. Full article
Open AccessReview Monocyclic Phenolic Acids; Hydroxy- and Polyhydroxybenzoic Acids: Occurrence and Recent Bioactivity Studies
Molecules 2010, 15(11), 7985-8005; doi:10.3390/molecules15117985
Received: 19 October 2010 / Revised: 3 November 2010 / Accepted: 4 November 2010 / Published: 8 November 2010
Cited by 92 | PDF Full-text (242 KB)
Abstract
Among the wide diversity of naturally occurring phenolic acids, at least 30 hydroxy- and polyhydroxybenzoic acids have been reported in the last 10 years to have biological activities. The chemical structures, natural occurrence throughout the plant, algal, bacterial, fungal and animal kingdoms, and
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Among the wide diversity of naturally occurring phenolic acids, at least 30 hydroxy- and polyhydroxybenzoic acids have been reported in the last 10 years to have biological activities. The chemical structures, natural occurrence throughout the plant, algal, bacterial, fungal and animal kingdoms, and recently described bioactivities of these phenolic and polyphenolic acids are reviewed to illustrate their wide distribution, biological and ecological importance, and potential as new leads for the development of pharmaceutical and agricultural products to improve human health and nutrition. Full article
(This article belongs to the Special Issue Phenolics and Polyphenolics)
Open AccessReview Recent Advance in Heterocyclic Organozinc and Organomanganese Compounds; Direct Synthetic Routes and Application in Organic Synthesis
Molecules 2010, 15(11), 8006-8038; doi:10.3390/molecules15118006
Received: 17 September 2010 / Revised: 1 November 2010 / Accepted: 4 November 2010 / Published: 8 November 2010
Cited by 8 | PDF Full-text (406 KB)
Abstract
A practical synthetic route for the preparation of 2-pyridyl and 3-pyridyl derivatives has been accomplished by utilizing a simple coupling reaction of stable 2-pyridylzinc bromides and 3-pyridylzinc bromides. The organozincs used in this study were easily prepared via the direct insertion of active
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A practical synthetic route for the preparation of 2-pyridyl and 3-pyridyl derivatives has been accomplished by utilizing a simple coupling reaction of stable 2-pyridylzinc bromides and 3-pyridylzinc bromides. The organozincs used in this study were easily prepared via the direct insertion of active zinc into the corresponding bromopyridines. The subsequent coupling reactions with a variety of different electrophiles have afforded the corresponding coupling products. Using highly active manganese, a variety of Grignard-type organomanganese reagents have been obtained. The subsequent coupling reactions of the resulting organomanganese reagents with several electrophiles have also been accomplished under mild conditions. Full article
(This article belongs to the Special Issue Advances in Heterocyclic Chemistry)
Open AccessReview Antioxidant Vitamins and Their Use in Preventing Cardiovascular Disease
Molecules 2010, 15(11), 8098-8110; doi:10.3390/molecules15118098
Received: 11 September 2010 / Revised: 21 October 2010 / Accepted: 27 October 2010 / Published: 9 November 2010
Cited by 42 | PDF Full-text (108 KB)
Abstract
Atherosclerosis remains one of the leading causes of death in Western populations. Subsequent to the discovery that oxidative stress plays a pivotal role in the development and progression of atherosclerosis, vitamins C and E, along with other antioxidants, were studied as potential therapies
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Atherosclerosis remains one of the leading causes of death in Western populations. Subsequent to the discovery that oxidative stress plays a pivotal role in the development and progression of atherosclerosis, vitamins C and E, along with other antioxidants, were studied as potential therapies for the disease. However, while in vitro and in vivo studies showed promising antiatherogenic effects for vitamins C and E, clinical trials in which patients were given high doses of vitamin E or C showed no benefit and even possible harm. This review will attempt to summarize the known mechanistic data regarding the biochemical effects of vitamins C and E and their relevance to atherosclerosis, and offer an explanation for the failure of clinical trials to show that supplementation with these vitamins provides any benefit when given indiscriminately. We provide one example of how pharmacogenomics may be used to identify a sub-population which may indeed benefit from antioxidant supplementation. Full article
(This article belongs to the Special Issue Antioxidants)
Open AccessReview Radiolabeled Small Molecule Protein Kinase Inhibitors for Imaging with PET or SPECT
Molecules 2010, 15(11), 8260-8278; doi:10.3390/molecules15118260
Received: 2 November 2010 / Revised: 10 November 2010 / Accepted: 11 November 2010 / Published: 15 November 2010
Cited by 32 | PDF Full-text (364 KB)
Abstract
Imaging protein kinase expression with radiolabeled small molecule inhibitors has been actively pursued to monitor the clinical potential of targeted therapeutics and treatments as well as to determine kinase receptor density changes related to disease progression. The goal of the present review is
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Imaging protein kinase expression with radiolabeled small molecule inhibitors has been actively pursued to monitor the clinical potential of targeted therapeutics and treatments as well as to determine kinase receptor density changes related to disease progression. The goal of the present review is to provide an overview of the breadth of radiolabeled small molecules that have been synthesized to target intracellular protein kinases, not only for imaging in oncology, but also for other areas of interest, particularly the central nervous system.  Considerable radiotracer development has focused on imaging receptor tyrosine kinases of growth factors, protein kinases A, B and C, and glycogen synthase kinase–3β. Design considerations, structural attributes and relevant biological results are summarized. Full article
(This article belongs to the Special Issue Radiochemistry)
Open AccessReview Combining the Benefits of Homogeneous and Heterogeneous Catalysis with Tunable Solvents and Nearcritical Water
Molecules 2010, 15(11), 8400-8424; doi:10.3390/molecules15118400
Received: 11 October 2010 / Accepted: 8 November 2010 / Published: 16 November 2010
Cited by 21 | PDF Full-text (456 KB)
Abstract
The greatest advantage of heterogeneous catalysis is the ease of separation, while the disadvantages are often limited activity and selectivity.  We report solvents that use tunable phase behavior to achieve homogeneous catalysis with ease of separation.  Tunable solvents are homogeneous mixtures of water
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The greatest advantage of heterogeneous catalysis is the ease of separation, while the disadvantages are often limited activity and selectivity.  We report solvents that use tunable phase behavior to achieve homogeneous catalysis with ease of separation.  Tunable solvents are homogeneous mixtures of water or polyethylene glycol with organics such as acetonitrile, dioxane, and THF that can be used for homogeneously catalyzed reactions. Modest pressures of a soluble gas, generally CO2, achieve facile post-reaction heterogeneous separation of products from the catalyst. Examples shown here are rhodium-catalyzed hydroformylation of 1-octene and p-methylstyrene and palladium catalyzed C-O coupling to produce o-tolyl-3,5-xylyl ether and 3,5-di-tert-butylphenol. Both were successfully carried out in homogeneous tunable solvents followed by separation efficiencies of up to 99% with CO2 pressures of 3 MPa. Further examples in tunable solvents are enzyme catalyzed reactions such as kinetic resolution of rac-1-phenylethyl acetate and hydrolysis of 2-phenylethyl acetate (2PEA) to 2-phenylethanol (2PE). Another tunable solvent is nearcritical water (NCW), whose unique properties offer advantages for developing sustainable alternatives to traditional processes. Some examples discussed are Friedel-Crafts alkylation and acylation, hydrolysis of benzoate esters, and water-catalyzed deprotection of N-Boc-protected amine compounds. Full article
(This article belongs to the Special Issue Heterogeneous Catalysis)
Open AccessReview Sorption Speciation of Lanthanides/Actinides on Minerals by TRLFS, EXAFS and DFT Studies: A Review
Molecules 2010, 15(11), 8431-8468; doi:10.3390/molecules15118431
Received: 8 October 2010 / Revised: 9 November 2010 / Accepted: 15 November 2010 / Published: 17 November 2010
Cited by 82 | PDF Full-text (1496 KB)
Abstract
Lanthanides/actinides sorption speciation on minerals and oxides by means of time resolved laser fluorescence spectroscopy (TRLFS), extended X-ray absorption fine structure spectroscopy (EXAFS) and density functional theory (DFT) is reviewed in the field of nuclear disposal safety research. The theoretical aspects of the
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Lanthanides/actinides sorption speciation on minerals and oxides by means of time resolved laser fluorescence spectroscopy (TRLFS), extended X-ray absorption fine structure spectroscopy (EXAFS) and density functional theory (DFT) is reviewed in the field of nuclear disposal safety research. The theoretical aspects of the methods are concisely presented. Examples of recent research results of lanthanide/actinide speciation and local atomic structures using TRLFS, EXAFS and DFT are discussed. The interaction of lanthanides/actinides with oxides and minerals as well as their uptake are also of common interest in radionuclide chemistry. Especially the sorption and inclusion of radionuclides into several minerals lead to an improvement in knowledge of minor components in solids. In the solid-liquid interface, the speciation and local atomic structures of Eu(III), Cm(III), U(VI), and Np(IV/VI) in several natural and synthetic minerals and oxides are also reviewed and discussed. The review is important to understand the physicochemical behavior of lanthanides/actinides at a molecular level in the natural environment. Full article
(This article belongs to the Special Issue Radiochemistry)

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Open AccessCorrection Al-Salahi, R. Synthesis and Reactivity of [1,2,4]Triazolo-annelated Quinazolines. Molecules 2010, 15, 7016-7034
Molecules 2010, 15(11), 8143; doi:10.3390/molecules15118143
Received: 9 November 2010 / Accepted: 10 November 2010 / Published: 10 November 2010
PDF Full-text (17 KB)
Abstract The authors wish to make the following corrections to the paper published in Molecules [1]: The authorship of the paper is changed to Rashad A. Al-Salahi and Detlef Geffken. [...] Full article

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