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Molecules, Volume 16, Issue 11 (November 2011), Pages 8930-9774

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Open AccessArticle Hypoglycemic and Hypolipidemic Effects of Polyphenols from Burs of Castanea mollissima Blume
Molecules 2011, 16(11), 9764-9774; https://doi.org/10.3390/molecules16119764
Received: 18 October 2011 / Revised: 14 November 2011 / Accepted: 15 November 2011 / Published: 24 November 2011
Cited by 20 | Viewed by 3813 | PDF Full-text (196 KB) | HTML Full-text | XML Full-text
Abstract
Substantial evidence suggests that phenolic extracts of Castanea mollissima spiny burs (CMPE) increase pancreatic cell viability after STZ (streptozotocin) treatment as a result of their antioxidant properties. In the present study, the hypoglycemic and hypolipidemic activities of CMPE were studied in normal and
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Substantial evidence suggests that phenolic extracts of Castanea mollissima spiny burs (CMPE) increase pancreatic cell viability after STZ (streptozotocin) treatment as a result of their antioxidant properties. In the present study, the hypoglycemic and hypolipidemic activities of CMPE were studied in normal and STZ-induced diabetic rats CMPE were orally administrated at doses of 150 and 300 mg/kg twice a day for 12 consecutive days. Serum glucose, triglyceride, total cholesterol, HDL- and LDL-cholesterol levels, malondialdehyde (MDA) level and SOD activity in liver, kidney, spleen and heart tissues were measured spectrophotometrically. In normal rats, no significant changes were observed in serum glucose, lipid profiles and tissue MDA and GSH levels after orally administration of CMPE. In diabetic rats, oral administration of CMPE at a dose of 300 mg/kg caused significant decreases in serum glucose, triglyceride, total cholesterol, LDL-cholesterol levels, as well as MDA and GSH levels in spleen and liver tissues. However, the 300 mg/kg dosage caused a significant body weight loss in both normal and diabetic rats. The observed effects indicated that CMPE could be further developed as a drug to prevent abnormal changes in blood glucose and lipid profile and to attenuate lipid peroxidation in liver and spleen tissues. Full article
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Open AccessArticle Synthesis of Methacrylate Monomers with Antibacterial Effects Against S. Mutans
Molecules 2011, 16(11), 9755-9763; https://doi.org/10.3390/molecules16119755
Received: 18 October 2011 / Revised: 21 November 2011 / Accepted: 22 November 2011 / Published: 23 November 2011
Cited by 49 | Viewed by 3224 | PDF Full-text (179 KB) | HTML Full-text | XML Full-text
Abstract
A series of polymerizable quaternary ammonium compounds were synthesized with the aim of using them as immobilized antibacterial agents in methacrylate dental composites, and their structures were characterized by FT-IR, 1H-NMR, and 13C-NMR analysis. Their antibacterial activities against the oral bacterium
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A series of polymerizable quaternary ammonium compounds were synthesized with the aim of using them as immobilized antibacterial agents in methacrylate dental composites, and their structures were characterized by FT-IR, 1H-NMR, and 13C-NMR analysis. Their antibacterial activities against the oral bacterium Streptococcus mutans were evaluated in vitro by a Minimum Inhibitory Concentration test, and the results showed that 2-dimethyl-2-hexadecyl-1-methacryloxyethyl ammonium iodide (C16) had the highest antibacterial activity against S. mutans, and 2-dimethyl-2-pentyl-1-methacryloxyethyl ammonium iodide (C5) and 2-dimethyl-2-octyl-1-methacryloxyethyl ammonium iodide (C8) did not show any inhibition. Full article
(This article belongs to the Section Medicinal Chemistry)
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Open AccessArticle Diversity Oriented Design of Various Benzophenone Derivatives and Their in Vitro Antifungal and Antibacterial Activities
Molecules 2011, 16(11), 9739-9754; https://doi.org/10.3390/molecules16119739
Received: 3 October 2011 / Revised: 9 November 2011 / Accepted: 14 November 2011 / Published: 23 November 2011
Cited by 9 | Viewed by 3048 | PDF Full-text (385 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
A series of new substituted benzophenone derivatives was designed, synthesized and screened for their antifungal and antibacterial activities. The bioassays indicated that most of the synthesized compounds showed some antifungal activity against the tested phytopathogenic fungi, but lower antibacterial activities towards the five
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A series of new substituted benzophenone derivatives was designed, synthesized and screened for their antifungal and antibacterial activities. The bioassays indicated that most of the synthesized compounds showed some antifungal activity against the tested phytopathogenic fungi, but lower antibacterial activities towards the five vibrios isolated from marine sources. The preliminary structure activity relationship (SAR) of the compounds was also discussed. Full article
(This article belongs to the Section Medicinal Chemistry)
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Open AccessArticle A Curcumin Derivative, 2,6-Bis(2,5-dimethoxybenzylidene)-cyclohexanone (BDMC33) Attenuates Prostaglandin E2 Synthesis via Selective Suppression of Cyclooxygenase-2 in IFN-g/LPS-Stimulated Macrophages
Molecules 2011, 16(11), 9728-9738; https://doi.org/10.3390/molecules16119728
Received: 26 September 2011 / Revised: 27 October 2011 / Accepted: 28 October 2011 / Published: 23 November 2011
Cited by 11 | Viewed by 3873 | PDF Full-text (421 KB) | HTML Full-text | XML Full-text
Abstract
Our preliminary screening had shown that the curcumin derivative [2,6-bis(2,5-dimethoxybenzylidene)cyclohexanone] or BDMC33 exhibited improved anti-inflammatory activity by inhibiting nitric oxide synthesis in activated macrophage cells. In this study, we further investigated the anti-inflammatory properties of BDMC33 on PGE2 synthesis and cyclooxygenase (COX)
[...] Read more.
Our preliminary screening had shown that the curcumin derivative [2,6-bis(2,5-dimethoxybenzylidene)cyclohexanone] or BDMC33 exhibited improved anti-inflammatory activity by inhibiting nitric oxide synthesis in activated macrophage cells. In this study, we further investigated the anti-inflammatory properties of BDMC33 on PGE2 synthesis and cyclooxygenase (COX) expression in IFN-g/LPS-stimulated macrophages. We found that BDMC33 significantly inhibited PGE2 synthesis in a concentration-dependent manner albeit at a low inhibition level with an IC50 value of 47.33 ± 1.00 µM. Interestingly, the PGE2 inhibitory activity of BDMC33 is not attributed to inhibition of the COX enzyme activities, but rather BDMC33 selectively down-regulated the expression of COX-2. In addition, BDMC33 modulates the COX expression by sustaining the constitutively COX-1 expression in IFN-g/LPS-treated macrophage cells. Collectively, the experimental data suggest an immunodulatory action of BDMC33 on PGE2 synthesis and COX expression, making it a possible treatment for inflammatory disorders with minimal gastrointestinal-related side effects. Full article
(This article belongs to the Section Medicinal Chemistry)
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Open AccessArticle Soulamarin, a New Coumarin from Stem Bark of Calophyllum soulattri
Molecules 2011, 16(11), 9721-9727; https://doi.org/10.3390/molecules16119721
Received: 22 September 2011 / Revised: 13 October 2011 / Accepted: 4 November 2011 / Published: 23 November 2011
Cited by 17 | Viewed by 3121 | PDF Full-text (267 KB) | HTML Full-text | XML Full-text
Abstract
The extracts of the stem bark of Calophyllum soulattri gave a new pyranocoumarin, soulamarin (1), together with five other xanthones caloxanthone B (2), caloxanthone C (3), macluraxanthone (4), trapezifolixanthone (5) and brasixanthone B
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The extracts of the stem bark of Calophyllum soulattri gave a new pyranocoumarin, soulamarin (1), together with five other xanthones caloxanthone B (2), caloxanthone C (3), macluraxanthone (4), trapezifolixanthone (5) and brasixanthone B (6) one common triterpene, friedelin (7), and the steroidal triterpene stigmasterol (8). The structures of these compounds were established based on spectral evidence (1D and 2D NMR). Full article
(This article belongs to the Special Issue Coumarins and Xanthones)
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Open AccessArticle Trypanocidal Activity of Oxoaporphine and Pyrimidine-β-Carboline Alkaloids from the Branches of Annona foetida Mart. (Annonaceae)
Molecules 2011, 16(11), 9714-9720; https://doi.org/10.3390/molecules16119714
Received: 13 October 2011 / Revised: 17 November 2011 / Accepted: 17 November 2011 / Published: 23 November 2011
Cited by 34 | Viewed by 4064 | PDF Full-text (203 KB) | HTML Full-text | XML Full-text
Abstract
Phytochemical investigation of the branches of Annona foetida Mart. led to isolation from the CH2Cl2 extract of four alkaloids: Atherospermidine (1), described for the first time in this species, liriodenine (2), O-methylmoschatoline (3),
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Phytochemical investigation of the branches of Annona foetida Mart. led to isolation from the CH2Cl2 extract of four alkaloids: Atherospermidine (1), described for the first time in this species, liriodenine (2), O-methylmoschatoline (3), and annomontine (4). Their chemical structures were established on the basis of spectroscopic data from IR, MS, NMR (1D and 2D), and comparison with the literature. Compounds 24 showed potent trypanocidal effect when evaluated against epimastigote and trypomastigote forms of Trypanosoma cruzi. Full article
(This article belongs to the Special Issue Aporphines and Oxoaporphines)
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Open AccessArticle Lipase-Catalyzed Kinetic Resolution of Aryltrimethylsilyl Chiral Alcohols
Molecules 2011, 16(11), 9697-9713; https://doi.org/10.3390/molecules16119697
Received: 27 September 2011 / Revised: 28 October 2011 / Accepted: 17 November 2011 / Published: 23 November 2011
Cited by 4 | Viewed by 4564 | PDF Full-text (243 KB) | HTML Full-text | XML Full-text
Abstract
Lipase-catalyzed kinetic resolution of aryltrimethylsilyl chiral alcohols through a transesterification reaction was studied. The optimal conditions found for the kinetic resolution of m- and p-aryltrimethylsilyl chiral alcohols, led to excellent results, high conversions (c = 50%), high enantiomeric ratios (
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Lipase-catalyzed kinetic resolution of aryltrimethylsilyl chiral alcohols through a transesterification reaction was studied. The optimal conditions found for the kinetic resolution of m- and p-aryltrimethylsilyl chiral alcohols, led to excellent results, high conversions (c = 50%), high enantiomeric ratios (E > 200) and enantiomeric excesses for the remaining (S)-alcohol and (R)-acetylated product (>99%). However, kinetic resolution of o-aryltrimethylsilyl chiral alcohols did not occur under the same conditions applied to the other isomers. Full article
(This article belongs to the Special Issue Organosilicon Chemistry)
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Open AccessReview A Journey Under the Sea: The Quest for Marine Anti-Cancer Alkaloids
Molecules 2011, 16(11), 9665-9696; https://doi.org/10.3390/molecules16119665
Received: 24 October 2011 / Accepted: 9 November 2011 / Published: 23 November 2011
Cited by 56 | Viewed by 5911 | PDF Full-text (301 KB) | HTML Full-text | XML Full-text
Abstract
The alarming increase in the global cancer death toll has fueled the quest for new effective anti-tumor drugs thorough biological screening of both terrestrial and marine organisms. Several plant-derived alkaloids are leading drugs in the treatment of different types of cancer and many
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The alarming increase in the global cancer death toll has fueled the quest for new effective anti-tumor drugs thorough biological screening of both terrestrial and marine organisms. Several plant-derived alkaloids are leading drugs in the treatment of different types of cancer and many are now being tested in various phases of clinical trials. Recently, marine-derived alkaloids, isolated from aquatic fungi, cyanobacteria, sponges, algae, and tunicates, have been found to also exhibit various anti-cancer activities including anti-angiogenic, anti-proliferative, inhibition of topoisomerase activities and tubulin polymerization, and induction of apoptosis and cytotoxicity. Two tunicate-derived alkaloids, aplidin and trabectedin, offer promising drug profiles, and are currently in phase II clinical trials against several solid and hematologic tumors. This review sheds light on the rich array of anti-cancer alkaloids in the marine ecosystem and introduces the most investigated compounds and their mechanisms of action. Full article
(This article belongs to the Special Issue Alkaloids: Novel Therapeutic Perspectives)
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Open AccessArticle Biological Activity of Carbazole Alkaloids and Essential Oil of Murraya koenigii Against Antibiotic Resistant Microbes and Cancer Cell Lines
Molecules 2011, 16(11), 9651-9664; https://doi.org/10.3390/molecules16119651
Received: 22 September 2011 / Revised: 9 November 2011 / Accepted: 11 November 2011 / Published: 21 November 2011
Cited by 58 | Viewed by 5094 | PDF Full-text (295 KB) | HTML Full-text | XML Full-text
Abstract
A total of three carbazole alkaloids and essential oil from the leaves of Murraya koenigii (Rutaceae) were obtained and examined for their effects on the growth of five antibiotic resistant pathogenic bacteria and three tumor cell lines (MCF-7, P 388 and Hela). The
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A total of three carbazole alkaloids and essential oil from the leaves of Murraya koenigii (Rutaceae) were obtained and examined for their effects on the growth of five antibiotic resistant pathogenic bacteria and three tumor cell lines (MCF-7, P 388 and Hela). The structures of these carbazoles were elucidated based on spectroscopy data and compared with literature data, hence, were identified as mahanine (1), mahanimbicine (2) and mahanimbine (3). The chemical constituents of the essential oil were identified using Gas Chromatography-Mass Spectroscopy (GCMS). These compounds exhibited potent inhibition against antibiotic resistant bacteria such as Staphylococcus aureus (210P JTU), Psedomonas aeruginosa (ATCC 25619), Klebsiella pneumonia (SR1-TU), Escherchia coli (NI23 JTU) and Streptococcus pneumoniae (SR16677-PRSP) with significant minimum inhibition concentration (MIC) values (25.0–175.0 mg/mL) and minimum bacteriacidal concentrations (MBC) (100.0–500.0 mg/mL). The isolated compounds showed significant antitumor activity against MCF-7, Hela and P388 cell lines. Mahanimbine (3) and essential oil in particular showed potent antibacteria and cytotoxic effect with dose dependent trends (≤5.0 μg/mL). The findings from this investigation are the first report of carbazole alkaloids’ potential against antibiotic resistant clinical bacteria, MCF-7 and P388 cell lines. Full article
(This article belongs to the Section Natural Products Chemistry)
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Open AccessCommunication A Planar Conformation and the Hydroxyl Groups in the B and C Rings Play a Pivotal Role in the Antioxidant Capacity of Quercetin and Quercetin Derivatives
Molecules 2011, 16(11), 9636-9650; https://doi.org/10.3390/molecules16119636
Received: 29 September 2011 / Revised: 11 November 2011 / Accepted: 14 November 2011 / Published: 21 November 2011
Cited by 27 | Viewed by 4816 | PDF Full-text (527 KB) | HTML Full-text | XML Full-text
Abstract
The polyphenol quercetin (Q) that has a high antioxidant capacity is a lead compound in the design of antioxidants. We investigated the possibility of modifying quercetin while retaining its antioxidant capacity as much as possible. To this end, the antioxidant capacities
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The polyphenol quercetin (Q) that has a high antioxidant capacity is a lead compound in the design of antioxidants. We investigated the possibility of modifying quercetin while retaining its antioxidant capacity as much as possible. To this end, the antioxidant capacities of Q, rutin, monohydroxyethyl rutinoside (monoHER) and a series of synthesized methylated Q derivatives were determined. The results confirm that the electron donating effect of the hydroxyl groups is essential. It was also found that the relatively planar structure of Q needs to be conserved. This planar conformation enables the distribution of the electron donating effect through the large conjugated π-system over the entire molecule. This is essential for the cooperation between the electron donating groups. Based on the activity of the compounds tested, it was concluded that structural modification at the 5 or 7 position is the most optimal to retain most of the antioxidant capacity of Q. This was confirmed by synthesizing and testing Q5OMe (Q6) and Q7OMe (Q7) that indeed displayed antioxidant capacities closest to Q. Full article
(This article belongs to the Section Medicinal Chemistry)
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Open AccessArticle Eco-Friendly Methodology to Prepare N-Heterocycles Related to Dihydropyridines: Microwave-Assisted Synthesis of Alkyl 4-Arylsubstituted-6-chloro-5-formyl-2-methyl-1,4-dihydropyridine-3-carboxylate and 4-Arylsubstituted-4,7-dihydrofuro[3,4-b]pyridine-2,5(1H,3H)-dione
Molecules 2011, 16(11), 9620-9635; https://doi.org/10.3390/molecules16119620
Received: 10 October 2011 / Revised: 26 October 2011 / Accepted: 15 November 2011 / Published: 21 November 2011
Cited by 6 | Viewed by 4160 | PDF Full-text (361 KB) | HTML Full-text | XML Full-text
Abstract
Here we describe the efficient synthesis of alkyl 4-arylsubstituted-6-chloro-5-formyl-2-methyl-1,4-dihydropyridine-3-carboxylates and 4-arylsubstituted-4,7-dihydro-furo[3,4-b]pyridine-2,5(1H,3H)-diones via microwave-accelerated reaction of alkyl 4-arylsubstituted-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxylates with the appropriate reagents. This eco-friendly approach to these valuable dihydropyridine derivatives does not involve the harsh or highly contaminating
[...] Read more.
Here we describe the efficient synthesis of alkyl 4-arylsubstituted-6-chloro-5-formyl-2-methyl-1,4-dihydropyridine-3-carboxylates and 4-arylsubstituted-4,7-dihydro-furo[3,4-b]pyridine-2,5(1H,3H)-diones via microwave-accelerated reaction of alkyl 4-arylsubstituted-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxylates with the appropriate reagents. This eco-friendly approach to these valuable dihydropyridine derivatives does not involve the harsh or highly contaminating conditions common in classical heating and offers a reduction or even elimination of solvent use and recovery, simplification of the work-up procedures, facility of scale up, and low energy consumption, in addition to moderate to higher yields. Full article
(This article belongs to the Section Organic Chemistry)
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Open AccessArticle Antimicrobial Evaluation of Diterpenes from Copaifera langsdorffii Oleoresin Against Periodontal Anaerobic Bacteria
Molecules 2011, 16(11), 9611-9619; https://doi.org/10.3390/molecules16119611
Received: 11 October 2011 / Revised: 14 November 2011 / Accepted: 15 November 2011 / Published: 18 November 2011
Cited by 53 | Viewed by 5374 | PDF Full-text (216 KB) | HTML Full-text | XML Full-text
Abstract
The antimicrobial activity of four labdane-type diterpenes isolated from the oleoresin of Copaifera langsdorffii as well as of two commercially available diterpenes (sclareol and manool) was investigated against a representative panel of microorganisms responsible for periodontitis. Among all the evaluated compounds, (−)-copalic acid
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The antimicrobial activity of four labdane-type diterpenes isolated from the oleoresin of Copaifera langsdorffii as well as of two commercially available diterpenes (sclareol and manool) was investigated against a representative panel of microorganisms responsible for periodontitis. Among all the evaluated compounds, (−)-copalic acid (CA) was the most active, displaying a very promising MIC value (3.1 µg mL−1; 10.2 µM) against the key pathogen (Porphyromonas gingivalis) involved in this infectious disease. Moreover, CA did not exhibit cytotoxicity when tested in human fibroblasts. Time-kill curve assays performed with CA against P. gingivalis revealed that this compound only inhibited the growth of the inoculums in the first 12 h (bacteriostatic effect). However, its bactericidal effect was clearly noted thereafter (between 12 and 24 h). It was also possible to verify an additive effect when CA and chlorhexidine dihydrochloride (CHD, positive control) were associated at their MBC values. The time curve profile resulting from this combination showed that this association needed only six hours for the bactericidal effect to be noted. In summary, CA has shown to be an important metabolite for the control of periodontal diseases. Moreover, the use of standardized extracts based on copaiba oleoresin with high CA contents can be an important strategy in the development of novel oral care products. Full article
(This article belongs to the Section Natural Products Chemistry)
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Open AccessArticle Interaction of the Main Components from the Traditional Chinese Drug Pair Chaihu-Shaoyao Based on Rat Intestinal Absorption
Molecules 2011, 16(11), 9600-9610; https://doi.org/10.3390/molecules16119600
Received: 18 October 2011 / Revised: 8 November 2011 / Accepted: 10 November 2011 / Published: 17 November 2011
Cited by 19 | Viewed by 3926 | PDF Full-text (221 KB) | HTML Full-text | XML Full-text
Abstract
The Chaihu-Shaoyao drug pair (Bupleuri Radix and Paeoniae Radix Alba) which is a traditional Chinese drug pair, has been widely used for anti-inflammatory purposes. Saikosaponin a (SSA), saikosaponin d (SSD) and paeoniflorin are identified as the main components in the pair. The present
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The Chaihu-Shaoyao drug pair (Bupleuri Radix and Paeoniae Radix Alba) which is a traditional Chinese drug pair, has been widely used for anti-inflammatory purposes. Saikosaponin a (SSA), saikosaponin d (SSD) and paeoniflorin are identified as the main components in the pair. The present study focused on the interaction of the main components based on investigating their intestinal absorption using a four-site perfused rat intestinal model in order to clarify the mechanism of the compatibility of Chaihu-Shaoyao. The concentrations of SSA, SSD and paeoniflorin in the intestinal perfusate were determined by LC/MS or UPLC (Ultra Performance Liquid Chromatography) methods, followed by P*eff (effective permeability) and 10% ABS (the percent absorption of 10 cm of intestine) calculations. The results showed that all of the three main components displayed very low permeabilities(P*eff < 0.4), which implied their poor absorption in the rat intestine. The absorption levels of SSA and SSD were similar in intestine and higher in ileum than those in other intestinal regions in the decreasing order: colon, jejunum and duodenum. However, there is no significant difference in the absorption of paeoniflorin in the four segments (P < 0.05). The P*eff values of paeoniflorin exhibited an almost 2.11-fold or 1.90-fold increase in ileum when it was co-administrated with SSA and SSD, as well as 2.42-, 2.18-fold increase in colon, respectively, whereas the absorptions of SSA and SSD were not influenced by paeoniflorin. In conclusion, SSA and SSD could promote the absorption of paeoniflorin. To some extent this might explain the nature of the compatibility mechanisms of composite formulae in TCMs. Full article
(This article belongs to the Section Molecular Diversity)
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Open AccessArticle The Beneficial Effect of Hydrogen on CO Oxidation over Au Catalysts. A Computational Study
Molecules 2011, 16(11), 9582-9599; https://doi.org/10.3390/molecules16119582
Received: 15 September 2011 / Revised: 30 October 2011 / Accepted: 3 November 2011 / Published: 16 November 2011
Cited by 11 | Viewed by 4334 | PDF Full-text (1289 KB) | HTML Full-text | XML Full-text
Abstract
Density functional theory calculations have been carried out to explore the effect of hydrogen on the oxidation of CO in relation to the preferential oxidation of CO in the presence of excess hydrogen (PROX). A range of gold surfaces have been selected including
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Density functional theory calculations have been carried out to explore the effect of hydrogen on the oxidation of CO in relation to the preferential oxidation of CO in the presence of excess hydrogen (PROX). A range of gold surfaces have been selected including the (100), stepped (310) surfaces and diatomic rows on the (100) surface. These diatomic rows on Au(100) are very efficient in H-H bond scission. O2 hydrogenation strongly enhances the surface-oxygen interaction and assists in scission of the O–O bond. The activation energy required to make the reaction intermediate hydroperoxy (OOH) from O2 and H is small. However, we postulate its presence on our Au models as the result of diffusion from oxide supports to the gold surfaces. The OOH on Au in turn opens many low energy cost channels to produce H2O and CO2. CO is selectively oxidized in a H2 atmosphere due to the more favorable reaction barriers while the formation of adsorbed hydroperoxy enhances the reaction rate. Full article
(This article belongs to the Special Issue Gold Catalysts)
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Open AccessArticle Mn(III)-Initiated Facile Oxygenation of Heterocyclic 1,3-Dicarbonyl Compounds
Molecules 2011, 16(11), 9562-9581; https://doi.org/10.3390/molecules16119562
Received: 27 September 2011 / Revised: 7 November 2011 / Accepted: 9 November 2011 / Published: 16 November 2011
Cited by 11 | Viewed by 3582 | PDF Full-text (434 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
The Mn(III)-initiated aerobic oxidation of heterocyclic 1,3-dicarbonyl compounds, such as 4-alkyl-1,2-diphenylpyrazolidine-3,5-diones, 1,3-dialkylpyrrolidine-2,4-diones, 3-alkyl-1,5-dimethylbarbituric acids, and 3-butyl-4-hydroxy-2-quinolinone gave excellent to good yields of the corresponding hydroperoxides, which were gradually degraded by exposure to the metal initiator after the reaction to afford the corresponding alcohols.
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The Mn(III)-initiated aerobic oxidation of heterocyclic 1,3-dicarbonyl compounds, such as 4-alkyl-1,2-diphenylpyrazolidine-3,5-diones, 1,3-dialkylpyrrolidine-2,4-diones, 3-alkyl-1,5-dimethylbarbituric acids, and 3-butyl-4-hydroxy-2-quinolinone gave excellent to good yields of the corresponding hydroperoxides, which were gradually degraded by exposure to the metal initiator after the reaction to afford the corresponding alcohols. The synthesis of 30 heterocyclic 1,3-dicarbonyl compounds, the corresponding hydroperoxides and the 10 alcohols, their characterization, and the limitations of the procedure are described. In addition, the mechanism of the hydroperoxidation and the redox decomposition of the hydroperoxides are discussed. Full article
(This article belongs to the Special Issue Radical Chemistry)
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Open AccessArticle One-Pot Synthesis of Novel 2,3-Dihydro-1H-indazoles
Molecules 2011, 16(11), 9553-9561; https://doi.org/10.3390/molecules16119553
Received: 8 October 2011 / Revised: 8 November 2011 / Accepted: 10 November 2011 / Published: 16 November 2011
Cited by 5 | Viewed by 2958 | PDF Full-text (237 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
A copper(I)-mediated one-pot synthesis of 2,3-dihydro-1H-indazole heterocycles has been developed. This synthetic route provides the desired indazoles in moderate to good yields (55%–72%) which are substantially better than those achievable with an alternative two-step reaction sequence. The reaction is tolerant of
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A copper(I)-mediated one-pot synthesis of 2,3-dihydro-1H-indazole heterocycles has been developed. This synthetic route provides the desired indazoles in moderate to good yields (55%–72%) which are substantially better than those achievable with an alternative two-step reaction sequence. The reaction is tolerant of functionality on the aromatic ring. Full article
(This article belongs to the Special Issue Heterocycles)
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Open AccessArticle The Effects of Combined Adiponectin-Metformin on Glucose and Lipids Levels in Mice and Acute Toxicity and Anti-Ulcerogenic Activity of Adiponectin Against Ethanol-Induced Gastric Mucosal Injuries in Rat
Molecules 2011, 16(11), 9534-9552; https://doi.org/10.3390/molecules16119534
Received: 13 September 2011 / Revised: 22 October 2011 / Accepted: 28 October 2011 / Published: 15 November 2011
Cited by 3 | Viewed by 4050 | PDF Full-text (691 KB) | HTML Full-text | XML Full-text
Abstract
Adiponectin is a protein hormone secreted entirely by abdominal fat tissue. It exhibits various biological activities. The present study was performed to evaluate the effects of metformin alone or in combination with adiponectin on blood glucose, TG (triglyceride), CHOL (Total cholesterol), LDL (Low
[...] Read more.
Adiponectin is a protein hormone secreted entirely by abdominal fat tissue. It exhibits various biological activities. The present study was performed to evaluate the effects of metformin alone or in combination with adiponectin on blood glucose, TG (triglyceride), CHOL (Total cholesterol), LDL (Low density lipoprotein) and HDL (High density lipoprotein) levels in mice and also to evaluate the anti-ulcerogenic activity of adiponectin against ethanol induced gastric mucosal injury in rats. Three groups of mice were gavaged with 1% volume/body weight high fat-sucrose. Metformin at a dosage of 250 mg/kg was added to the feed and a dosage of 2.5 mg/kg adiponectin was injected intraperitoneally (i.p). Blood glucose was measured at one hour intervals for five hours. Blood concentrations of TG, CHOL, LDL and HDL were also measured at the end of the fifth hour of the experiment. On the other hand, four groups of adult healthy rats were i.p. injected with distilled water, omeprazole 20 mg/kg, 2.5 mg/kg and 5 mg/kg adiponectin one hour before oral administration of absolute ethanol to generate gastric mucosal injury. After an additional hour the rats were sacrificed and the ulcer areas of the gastric walls were determined. Furthermore, an acute toxicity study has indicated no mortality with 5 mg/kg dose of adiponectin injected i.p in rats and no major clinical signs of toxicity were observed. The results indicate that the effect of a combination of metformin and adiponectin on blood glucose and HDL is quite effective. Histology of the gastric wall of negative control rats revealed severe damage of gastric mucosa, along with edema and leucocyte infiltration of the submucosal layer compared to rats pre-treated with either omeprazole or adiponectin extract where there was marked gastric protection along with reduction or inhibition of edema and leucocytes infiltration. The results suggest that combination of metfomin and adiponectin give a promising antidiabetic effect and also, adiponectin promotes ulcer protection as ascertained by the comparative decrease of ulcer areas, reduction of edema and leucocytes infiltration of the submucosal layer. Full article
(This article belongs to the Section Molecular Diversity)
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Open AccessArticle Acetylcholinesterase-inhibiting Alkaloids from Zephyranthes concolor
Molecules 2011, 16(11), 9520-9533; https://doi.org/10.3390/molecules16119520
Received: 17 October 2011 / Revised: 27 October 2011 / Accepted: 7 November 2011 / Published: 15 November 2011
Cited by 15 | Viewed by 4869 | PDF Full-text (250 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
The bulbs and aerial parts of Zephyranthes concolor (Lindl.) Benth. & Hook. f. (Amaryllidaceae), an endemic species to Mexico, were found to contain the alkaloids chlidanthine, galanthamine, galanthamine N-oxide, lycorine, galwesine, and epinorgalanthamine. Since currently only partial and low resolution 1H-NMR data
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The bulbs and aerial parts of Zephyranthes concolor (Lindl.) Benth. & Hook. f. (Amaryllidaceae), an endemic species to Mexico, were found to contain the alkaloids chlidanthine, galanthamine, galanthamine N-oxide, lycorine, galwesine, and epinorgalanthamine. Since currently only partial and low resolution 1H-NMR data for chlidanthine acetate are available, and none for chlidanthine, its 1D and 2D high resolution 1H- and 13C-NMR spectra were recorded. Unambiguous assignations were achieved with HMBC, and HSQC experiments, and its structure was corroborated by X-ray diffraction. Minimum energy conformation for structures of chlidanthine, and its positional isomer galanthamine, were calculated by molecular modelling. Galanthamine is a well known acetylcholinesterase inhibitor; therefore, the isolated alkaloids were tested for this activity. Chlidanthine and galanthamine N-oxide inhibited electric eel acetylcholinesterase (2.4 and 2.6 × 10−5 M, respectively), indicating they are about five times less potent than galanthamine, while galwesine was inactive at 10−3 M. Inhibitory activity of HIV-1 replication, and cytotoxicity of the isolated alkaloids were evaluated in human MT-4 cells; however, the alkaloids showed poor activity as compared with standard anti-HIV drugs, but most of them were not cytotoxic. Full article
(This article belongs to the Special Issue Alkaloids: Novel Therapeutic Perspectives)
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Open AccessArticle A Triterpenoid from Thalictrum fortunei Induces Apoptosis in BEL-7402 Cells Through the P53-Induced Apoptosis Pathway
Molecules 2011, 16(11), 9505-9519; https://doi.org/10.3390/molecules16119505
Received: 26 September 2011 / Revised: 4 November 2011 / Accepted: 8 November 2011 / Published: 15 November 2011
Cited by 10 | Viewed by 3411 | PDF Full-text (551 KB) | HTML Full-text | XML Full-text
Abstract
Thalictrum fortunei S. Moore, a perennial plant distributed in the southeastern part of China, has been used in Traditional Chinese Medicine for thousands of years for its antitumor, antibacterial and immunoregulatory effects. In order to investigate the active components and the mechanism of
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Thalictrum fortunei S. Moore, a perennial plant distributed in the southeastern part of China, has been used in Traditional Chinese Medicine for thousands of years for its antitumor, antibacterial and immunoregulatory effects. In order to investigate the active components and the mechanism of the anti-tumor effects of Thalictrum fortunei, the growth inhibitory effects of eight triterpenoids isolated from the aerial parts of the plant on tumor cell lines were examined by 3-(4,5)-dimethylthiazoy1-3,5-diphenyltetrazolium bromide (MTT) assay. The MTT-assay results showed that the inhibitory activity of 3-O-β-D-glucopyranosyl-(1→4)-β-D-fucopyranosyl(22S,24Z)-cycloart-24-en-3β,22,26-triol 26-O-β-D-glucopyranoside (1) was stronger than that of the other seven tested triterpenoids on human hepatoma Bel-7402 cell line (Bel-7402), human colon lovo cells (LoVo), human non-small cells lung cancer NCIH-460 cells (NCIH-460) and human gastric carcinoma SGC-7901 cells (SGC-7901) after 48 h treatment in vitro, with the IC50 values of 66.4, 84.8, 73.5, 89.6 μM, respectively. Moreover, the antitumor mechanism of compound 1 on Bel-7402 cell was explored through nucleus dyeing, fluorescence assay, flow cytometry and western blot. The flow cytometric analysis results revealed that compound 1 caused apoptosis and mitochondrial membrane potential (MMP) loss in Bel-7402 cells. A fluorescence assay indicated that intracellular reactive oxygen species (ROS) were markedly provoked by compound 1 treatment compared to control cells. Immunoblot results showed that compound 1 significantly increased the expression levels of cleaved caspase-3, P53 and Bax protein, and decreased the expression level of Bcl-2 protein. These findings indicate that compound 1 inhibits the growth activity of tumor cells, probably through the P53 protein-induced apoptosis pathway. Full article
(This article belongs to the Section Natural Products Chemistry)
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Open AccessArticle Synthesis of Endohedral Metallofullerene Glycoconjugates by Carbene Addition
Molecules 2011, 16(11), 9495-9504; https://doi.org/10.3390/molecules16119495
Received: 18 October 2011 / Revised: 3 November 2011 / Accepted: 10 November 2011 / Published: 14 November 2011
Cited by 11 | Viewed by 3873 | PDF Full-text (450 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Endohedral metallofullerene glycoconjugates were synthesized under mild conditions by carbene addition using appropriate glycosylidene-derived diazirine with La2@Ih-C80. NMR spectroscopic studies revealed that the glycoconjugate consists of two diastereomers of [6,6]-open mono-adducts. The electronic properties were characterized
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Endohedral metallofullerene glycoconjugates were synthesized under mild conditions by carbene addition using appropriate glycosylidene-derived diazirine with La2@Ih-C80. NMR spectroscopic studies revealed that the glycoconjugate consists of two diastereomers of [6,6]-open mono-adducts. The electronic properties were characterized using Vis/NIR absorption spectroscopy and electrochemical measurements. This study demonstrates that glycosylidene carbene is useful to incorporate carbohydrate moieties onto endohedral metallofullerene surfaces. Full article
(This article belongs to the Special Issue Fullerene Chemistry)
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Open AccessArticle Purification of a Lectin from Arisaema erubescens (Wall.) Schott and Its Pro-Inflammatory Effects
Molecules 2011, 16(11), 9480-9494; https://doi.org/10.3390/molecules16119480
Received: 24 October 2011 / Revised: 7 November 2011 / Accepted: 8 November 2011 / Published: 14 November 2011
Cited by 10 | Viewed by 3419 | PDF Full-text (605 KB) | HTML Full-text | XML Full-text
Abstract
The monocot lectin from the tubers of Arisaema erubescens (Wall.) Schott has been purified by consecutive hydrophobic chromatography and ion exchange chromatography methods. The molecular weight of this A. erubescens lectin (AEL) was determined to be about 12 kDa by high performance liquid
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The monocot lectin from the tubers of Arisaema erubescens (Wall.) Schott has been purified by consecutive hydrophobic chromatography and ion exchange chromatography methods. The molecular weight of this A. erubescens lectin (AEL) was determined to be about 12 kDa by high performance liquid chromatography (HPLC) and sodium dodecyl sulphate polyacrylamide gel electrophoresis (SDS-PAGE) methods. AEL could agglutinate rabbit erythrocytes. The haemagglutination activity of AEL was only inhibited by asialofetuin, while monosaccharide did not react. Rat paw edema and neutrophil migration models were used to investigate the pro-inflammatory activity of AEL. AEL (100 and 200 μg/paw) could induce significant rat paw edema. In addition, AEL (100, 200 and 300 μg/mL/cavity) could induce significant and dose-dependent neutrophil migration in the rat peritoneal cavities. Besides, AEL at doses ranging from 100 to 300 μg/mL/cavity could significantly increase the concentration of nitric oxide (NO), prostaglandin E2 (PGE2) and tumor necrosis factor alpha (TNF-α) in peritoneal fluid. As compared with control animals, 75% depletion in the number of resident cells following peritoneal lavage did not reduce the AEL-induced neutrophil migration. However, pre-treatment with 3% thioglycollate which increased the peritoneal macrophage population by 201%, enhanced the neutrophil migration induced by AEL (200 μg/mL/cavity) (p < 0.05). Reduction of peritoneal mast cell population by chronic treatment of rat peritoneal cavities with compound 48/80 (N-methyl-p-methoxyphenethylamine with formaldehyde) did not modify AEL-induced neutrophil migration. The results provided the basis for identifying the toxic components of A. erubescens and AEL could be a new useful tool for pro-inflammatory research. Full article
(This article belongs to the Section Natural Products Chemistry)
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Open AccessArticle Study of the Reaction 2-(p-Nitrophenyl)ethyl Bromide + OH in Dimeric Micellar Solutions
Molecules 2011, 16(11), 9467-9479; https://doi.org/10.3390/molecules16119467
Received: 13 October 2011 / Revised: 31 October 2011 / Accepted: 8 November 2011 / Published: 11 November 2011
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Abstract
The dehydrobromination reaction 2-(p-nitrophenyl)ethyl bromide + OH was investigated in several alkanediyl-a-w-bis(dodecyldimethylammonium) bromide, 12-s-12,2Br (with s = 2, 3, 4, 5, 6, 8, 10, 12) micellar solutions, in the presence of NaOH 5 × 10−3 M. The kinetic
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The dehydrobromination reaction 2-(p-nitrophenyl)ethyl bromide + OH was investigated in several alkanediyl-a-w-bis(dodecyldimethylammonium) bromide, 12-s-12,2Br (with s = 2, 3, 4, 5, 6, 8, 10, 12) micellar solutions, in the presence of NaOH 5 × 10−3 M. The kinetic data were quantitatively rationalized within the whole surfactant concentration range by using an equation based on the pseudophase ion-exchange model and taking the variations in the micellar ionization degree caused by the morphological transitions into account. The agreement between the theoretical and the experimental data was good in all the dimeric micellar media studied, except for the 12-2-12,2Br micellar solutions. In this case, the strong tendency to micellar growth shown by the 12-2-12,2Br micelles could be responsible for the lack of accordance. Results showed that the dimeric micelles accelerate the reaction more than two orders of magnitude as compared to water. Full article
(This article belongs to the Special Issue Reactions in Water)
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Open AccessArticle Anti-Inflammatory and Free Radial Scavenging Activities of the Constituents Isolated from Machilus zuihoensis
Molecules 2011, 16(11), 9451-9466; https://doi.org/10.3390/molecules16119451
Received: 19 September 2011 / Revised: 1 November 2011 / Accepted: 2 November 2011 / Published: 10 November 2011
Cited by 15 | Viewed by 4537 | PDF Full-text (521 KB) | HTML Full-text | XML Full-text
Abstract
A new biflavonol glycoside, quercetin-3-O-β-D-glucopyranoside-(3¢→O-3¢¢¢)- quercetin-3-O-β-D-galactopyranoside (9), together with eight known compounds was isolated for the first time from the leaves of Machilus zuihoensis Hayata (Lauraceae). The structure of compound 9 was elucidated by various
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A new biflavonol glycoside, quercetin-3-O-β-D-glucopyranoside-(3¢→O-3¢¢¢)- quercetin-3-O-β-D-galactopyranoside (9), together with eight known compounds was isolated for the first time from the leaves of Machilus zuihoensis Hayata (Lauraceae). The structure of compound 9 was elucidated by various types of spectroscopic data analysis. Analysis of the biological activity assay found that compound 9 showed significant superoxide anion scavenging activity (IC50 is 30.4 μM) and markedly suppressed LPS-induced high mobility group box 1 (HMGB-1) protein secretion in RAW264.7 cells. In addition, the HMGB-1 protein secretion was also inhibited by quercitrin (3), ethyl caffeate (6), and ethyl 3-O-caffeoylquinate (7) treatment. In the LPS-stimulated inducible nitric oxide synthase (iNOS) activation analysis, two known compounds, quercetin (1) and ethyl caffeate (6), were found to markedly suppress nitric oxide (NO) production (IC50 value, 27.6 and 42.9 μM, respectively) in RAW264.7 cells. Additionally, it was determined that ethyl caffeate (6) down-regulated mRNA expressions of iNOS, IL-1β, and IL-10 in the LPS-treatment of RAW264.7 cells via a suppressed NF-kB pathway. These results suggested for the first time that the new compound 9 and other constituents isolated from M. zuihoensis have potential anti-inflammatory and superoxide anion scavenging effects. These constituents may be useful for treating various inflammatory diseases. Full article
(This article belongs to the Section Natural Products Chemistry)
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Open AccessArticle Antioxidant Activity and Total Phenols from the Methanolic Extract of Miconia albicans (Sw.) Triana Leaves
Molecules 2011, 16(11), 9439-9450; https://doi.org/10.3390/molecules16119439
Received: 19 August 2011 / Revised: 20 October 2011 / Accepted: 2 November 2011 / Published: 10 November 2011
Cited by 10 | Viewed by 5050 | PDF Full-text (252 KB) | HTML Full-text | XML Full-text
Abstract
Miconia is one of the largest genus of the Melastomataceae, with approximately 1,000 species. Studies aiming to describe the diverse biological activities of the Miconia species have shown promising results, such as analgesic, antimicrobial and trypanocidal properties. M. albicans leaves were dried, powdered
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Miconia is one of the largest genus of the Melastomataceae, with approximately 1,000 species. Studies aiming to describe the diverse biological activities of the Miconia species have shown promising results, such as analgesic, antimicrobial and trypanocidal properties. M. albicans leaves were dried, powdered and extracted to afford chloroformic and methanolic extracts. Total phenolic contents in the methanolic extract were determined according to modified Folin-Ciocalteu method. The antioxidant activity was measured using AAPH and DPPH radical assays. Chemical analysis was performed with the n-butanol fraction of the methanolic extract and the chloroformic extract, using different chromatographic techniques (CC, HPLC). The structural elucidation of compounds was performed using 500 MHz NMR and HPLC methods. The methanolic extract showed a high level of total phenolic contents; the results with antioxidant assays showed that the methanolic extract, the n-butanolic fraction and the isolated flavonoids from M. albicans had a significant scavenging capacity against AAPH and DPPH. Quercetin, quercetin-3-O-glucoside, rutin, 3-(E)-p-coumaroyl-α-amyrin was isolated from the n-butanolic fraction and α-amyrin, epi-betulinic acid, ursolic acid, epi-ursolic acid from the chloroformic extract. The results presented in this study demonstrate that M. albicans is a promising species in the search for biologically active compounds. Full article
(This article belongs to the Section Natural Products Chemistry)
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Open AccessArticle Indatraline: Synthesis and Effect on the Motor Activity of Wistar Rats
Molecules 2011, 16(11), 9421-9438; https://doi.org/10.3390/molecules16119421
Received: 17 October 2011 / Revised: 3 November 2011 / Accepted: 7 November 2011 / Published: 10 November 2011
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Abstract
A new approach for the synthesis of indatraline was developed using as the key step an iodine(III)-mediated ring contraction of a 1,2-dihydronaphthalene derivative. Behavioral tests were conducted to evaluate the effect of indatraline and of its precursor indanamide on the motor activity of
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A new approach for the synthesis of indatraline was developed using as the key step an iodine(III)-mediated ring contraction of a 1,2-dihydronaphthalene derivative. Behavioral tests were conducted to evaluate the effect of indatraline and of its precursor indanamide on the motor activity of Wistar rats. Specific indexes for ambulation, raising and stereotypy were computed one, two and three hours after i.p. drug administration. Indatraline effects on motor activity lasted for at least three hours. On the other hand, no significant differences in motor activity were observed using indanamide. The results suggest that indatraline has a long lasting effect on motor activity and add evidence in favor of the potential use of that compound as a substitute in cocaine addiction. Full article
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Open AccessArticle Succinobucol’s New Coat — Conjugation with Steroids to Alter Its Drug Effect and Bioavailability
Molecules 2011, 16(11), 9404-9420; https://doi.org/10.3390/molecules16119404
Received: 29 September 2011 / Revised: 2 November 2011 / Accepted: 7 November 2011 / Published: 10 November 2011
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Abstract
Synthesis, detailed structural characterization (X-ray, NMR, MS, IR, elemental analysis), and studies of toxicity, antioxidant activity and bioavailability of unique potent anti-atherosclerotic succinobucol-steroid conjugates are reported. The conjugates consist of, on one side, the therapeutically important drug succinobucol ([4-{2,6-di-tert-butyl-4-[(1-{[3-tert-butyl-4-hydroxy-5-(propan-2-yl)phenyl]sulfanyl}ethyl)sulfanyl]phenoxy}-4-oxo-butanoic
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Synthesis, detailed structural characterization (X-ray, NMR, MS, IR, elemental analysis), and studies of toxicity, antioxidant activity and bioavailability of unique potent anti-atherosclerotic succinobucol-steroid conjugates are reported. The conjugates consist of, on one side, the therapeutically important drug succinobucol ([4-{2,6-di-tert-butyl-4-[(1-{[3-tert-butyl-4-hydroxy-5-(propan-2-yl)phenyl]sulfanyl}ethyl)sulfanyl]phenoxy}-4-oxo-butanoic acid]) possessing an antioxidant and anti-inflammatory activity, and on the other side, plant stanol/sterols (stigmastanol, β-sitosterol and stigmasterol) possessing an ability to lower the blood cholesterol level. A cholesterol-succinobucol prodrug was also prepared in order to enhance the absorption of succinobucol through the intestinal membrane into the organism and to target the drug into the place of lipid metabolism—The enterohepatic circulation system. Their low toxicity towards mice fibroblasts at maximal concentrations, their antioxidant activity, comparable or even higher than that of ascorbic acid as determined by direct quenching of the DPPH radical, and their potential for significantly altering total and LDL cholesterol levels, suggest that these conjugates merit further studies in the treatment of cardiovascular or other related diseases. A brief discussion of succinobucol’s ability to quench the radicals, supported with a computational model of the electrostatic potential mapped on the electron density surface of the drug, is also presented. Full article
(This article belongs to the Special Issue Steroids)
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Open AccessArticle Chemical Constituents of the Mexican Mistletoe (Psittacanthus calyculatus)
Molecules 2011, 16(11), 9397-9403; https://doi.org/10.3390/molecules16119397
Received: 11 October 2011 / Revised: 4 November 2011 / Accepted: 7 November 2011 / Published: 9 November 2011
Cited by 15 | Viewed by 3584 | PDF Full-text (242 KB) | HTML Full-text | XML Full-text
Abstract
A phytochemical study of the methanol-soluble fraction of an aqueous extract of a sample of Psittacanthus calyculatus collected from the host plant Prosopsis laevigata (Smooth Mesquite) using several techniques, including co-chromatography coupled with UV detection, chromatographic purifications and IR, NMR and MS studies,
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A phytochemical study of the methanol-soluble fraction of an aqueous extract of a sample of Psittacanthus calyculatus collected from the host plant Prosopsis laevigata (Smooth Mesquite) using several techniques, including co-chromatography coupled with UV detection, chromatographic purifications and IR, NMR and MS studies, resulted in the identification of gallic acid, two flavonol-3-biosides and the nonprotein amino acid N-methyl-trans-4-hydroxy-L-proline. Full article
(This article belongs to the Section Natural Products Chemistry)
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Open AccessArticle Antimicrobial Prospect of Newly Synthesized 1,3-Thiazole Derivatives
Molecules 2011, 16(11), 9386-9396; https://doi.org/10.3390/molecules16119386
Received: 8 October 2011 / Revised: 31 October 2011 / Accepted: 7 November 2011 / Published: 9 November 2011
Cited by 19 | Viewed by 4013 | PDF Full-text (228 KB) | HTML Full-text | XML Full-text
Abstract
A new series of 1,3-thiazole and benzo[d]thiazole derivatives 10–15 has been developed, characterized, and evaluated for in vitro antimicrobial activity at concentrations of 25–200 μg/mL against Gram+ve organisms such as methicillin-resistant Staphylococcus aureus (MRSA), Gram–ve organisms such as Escherichia
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A new series of 1,3-thiazole and benzo[d]thiazole derivatives 10–15 has been developed, characterized, and evaluated for in vitro antimicrobial activity at concentrations of 25–200 μg/mL against Gram+ve organisms such as methicillin-resistant Staphylococcus aureus (MRSA), Gram–ve organisms such as Escherichia coli (E. coli), and the fungal strain Aspergillus niger (A. niger) by the cup plate method. Ofloxacin and ketoconazole (10 μg/mL) were used as reference standards for antibacterial and antifungal activity, respectively. Compounds 11 and 12 showed notable antibacterial and antifungal activities at higher concentrations (125–200 μg/mL), whereas benzo[d]thiazole derivatives 13 and 14 were found to display significant antibacterial or antifungal activity (50–75 μg/mL) against the Gram+ve, Gram–ve bacteria, or fungal cells used in the present study. In addition, a correlation between calculated and determined partition coefficient (log P) was established which allows future development of compounds within this series to be carried out based on calculated log P values. Moreover, compounds 13 and 14 show that the optimum logarithm of partition coefficient (log P) should be around 4. Full article
(This article belongs to the Section Medicinal Chemistry)
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Open AccessArticle Synthesis and Biological Evaluation of 3-Substituted-indolin-2-one Derivatives Containing Chloropyrrole Moieties
Molecules 2011, 16(11), 9368-9385; https://doi.org/10.3390/molecules16119368
Received: 10 October 2011 / Revised: 3 November 2011 / Accepted: 3 November 2011 / Published: 8 November 2011
Cited by 6 | Viewed by 3606 | PDF Full-text (215 KB) | HTML Full-text | XML Full-text
Abstract
Eighteen novel 3-substituted-indolin-2-ones containing chloropyrroles were synthesized and their biological activities were evaluated. The presence of a chlorine atom on the pyrrole ring was crucial to reduce cardiotoxicity. The presence of a 2-(ethyl-amino)ethylcarbamoyl group as a substituent at the C-4′ position of the
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Eighteen novel 3-substituted-indolin-2-ones containing chloropyrroles were synthesized and their biological activities were evaluated. The presence of a chlorine atom on the pyrrole ring was crucial to reduce cardiotoxicity. The presence of a 2-(ethyl-amino)ethylcarbamoyl group as a substituent at the C-4′ position of the pyrrole enhanced the antitumor activities notably. IC50 values as low as 0.32, 0.67, 1.19 and 1.22 μM were achieved against non-small cell lung cancer (A549), oral epithelial (KB), melanoma (K111) and large cell lung cancer cell lines (NCI-H460), respectively. Full article
(This article belongs to the Section Medicinal Chemistry)
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Open AccessArticle Stigmasterol-Based Novel Low Molecular Weight/Mass Organic Gelators
Molecules 2011, 16(11), 9357-9367; https://doi.org/10.3390/molecules16119357
Received: 25 October 2011 / Revised: 31 October 2011 / Accepted: 2 November 2011 / Published: 8 November 2011
Cited by 5 | Viewed by 3512 | PDF Full-text (318 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Conjugates consisting of stigmasterol and L-phenylalanine, interconnected through short-chained dicarboxylic acyls by ester and amide bonds, respectively, were synthesized as potential low molecular weight/mass organic gelators (LMWGs/LMMGs). Their physico-chemical properties were subjected to investigation, especially their ability to form gels reversibly based on
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Conjugates consisting of stigmasterol and L-phenylalanine, interconnected through short-chained dicarboxylic acyls by ester and amide bonds, respectively, were synthesized as potential low molecular weight/mass organic gelators (LMWGs/LMMGs). Their physico-chemical properties were subjected to investigation, especially their ability to form gels reversibly based on changes of the environmental conditions. Other self-assembly properties detectable by UV-VIS traces were measured in systems consisting of two miscible solvents (water/acetonitrile) with varying solvent ratios and using constant concentrations of the studied compounds. Partition and diffusion coefficients and solubility in water were calculated for the target conjugates. The conjugate 3a was the only compound from this series capable of forming a gel in 1-octanol. All three conjugates 3a–3c displayed supramolecular characteristics in the UV-VIS spectra. Full article
(This article belongs to the Special Issue Steroids)
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