Next Issue
Previous Issue

E-Mail Alert

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

Journal Browser

Journal Browser

Table of Contents

Molecules, Volume 16, Issue 8 (August 2011), Pages 6165-7182

  • Issues are regarded as officially published after their release is announced to the table of contents alert mailing list.
  • You may sign up for e-mail alerts to receive table of contents of newly released issues.
  • PDF is the official format for papers published in both, html and pdf forms. To view the papers in pdf format, click on the "PDF Full-text" link, and use the free Adobe Readerexternal link to open them.
View options order results:
result details:
Displaying articles 1-77
Export citation of selected articles as:

Research

Jump to: Review, Other

Open AccessArticle Synthesis and Biological Evaluation of Novel 99mTc-Labelled Bisphosphonates as Superior Bone Imaging Agents
Molecules 2011, 16(8), 6165-6178; doi:10.3390/molecules16086165
Received: 10 June 2011 / Revised: 15 July 2011 / Accepted: 19 July 2011 / Published: 25 July 2011
Cited by 13 | PDF Full-text (651 KB)
Abstract
A series of novel zoledronic acid (ZL) derivatives 1-hydroxy-3-(2-methyl-1H-imidazol-1-yl)propane-1,1-diyldiphosphonic acid (MIPrDP), 1-hydroxy-4-(2-methyl-1H-imidazol-1-yl)butane-1,1-diyldiphosphonic acid (MIBDP), and 1-hydroxy-5-(2-methyl-1H-imidazol-1-yl)pentane-1,1-diyldiphosphonic acid (MIPeDP) were prepared and successfully labeled with 99mTc in high labeling yields. The in vitro stability and in [...] Read more.
A series of novel zoledronic acid (ZL) derivatives 1-hydroxy-3-(2-methyl-1H-imidazol-1-yl)propane-1,1-diyldiphosphonic acid (MIPrDP), 1-hydroxy-4-(2-methyl-1H-imidazol-1-yl)butane-1,1-diyldiphosphonic acid (MIBDP), and 1-hydroxy-5-(2-methyl-1H-imidazol-1-yl)pentane-1,1-diyldiphosphonic acid (MIPeDP) were prepared and successfully labeled with 99mTc in high labeling yields. The in vitro stability and in vivo biodistribution of 99mTc-MIPrDP, 99mTc-MIBDP and 99mTc-MIPeDP were investigated and compared. The biodistribution studies indicate that the radiotracer 99mTc-MIPrDP has highly selective uptake in the skeletal system and rapid clearance from soft tissues. The present findings indicate that 99mTc-MIPrDP holds great potential for use in bone imaging. Full article
(This article belongs to the Special Issue Radical Chemistry)
Open AccessArticle Antioxidant Activity of Papaya Seed Extracts
Molecules 2011, 16(8), 6179-6192; doi:10.3390/molecules16086179
Received: 27 June 2011 / Revised: 18 July 2011 / Accepted: 19 July 2011 / Published: 25 July 2011
Cited by 21 | PDF Full-text (417 KB)
Abstract
The antioxidant activities of the ethanol, petroleum ether, ethyl acetate, n-butanol and water extract fractions from the seeds of papaya were evaluated in this study. The ethyl acetate fraction showed the strongest DPPH and hydroxyl free radical-scavenging activities, and its activities [...] Read more.
The antioxidant activities of the ethanol, petroleum ether, ethyl acetate, n-butanol and water extract fractions from the seeds of papaya were evaluated in this study. The ethyl acetate fraction showed the strongest DPPH and hydroxyl free radical-scavenging activities, and its activities were stronger than those of ascorbic acid and sodium benzoate, respectively. The n-butanol fraction demonstrated the greatest ABTS+ radicals scavenging activity. The ethyl acetate fraction and the n-butanol fraction not only showed higher antioxidant activities than the petroleum ether fraction, water fraction and ethanol fraction, but also showed higher superoxide anion and hydrogen peroxide radicals scavenging activities than those of the other extract fractions. The high amount of total phenolics and total flavonoids in the ethyl acetate and n-butanol fractions contributed to their antioxidant activities. The ethyl acetate fraction was subjected to column chromatography, to yield two phenolic compounds, p-hydroxybenzoic acid (1) and vanillic acid (2), which possessed significant antioxidant activities. Therefore, the seeds of papaya and these compounds might be used as natural antioxidants. Full article
Open AccessArticle Preliminary Phytochemical Screening and In Vitro Anti-Helicobacter pylori Activity of Extracts of the Stem Bark of Bridelia micrantha (Hochst., Baill., Euphorbiaceae)
Molecules 2011, 16(8), 6193-6205; doi:10.3390/molecules16086193
Received: 17 June 2011 / Revised: 15 July 2011 / Accepted: 21 July 2011 / Published: 25 July 2011
Cited by 8 | PDF Full-text (480 KB)
Abstract
Helicobacter pylori is a major risk factor for gastritis, ulcers and gastric cancer. This study was aimed to determine the antimicrobial activity of the stem bark of Bridelia. micrantha on H. pylori isolated in South Africa. Extracts and clarithromycin were tested against 31 clinical strains, including a standard strain (NCTC 11638) of H. pylori, by measuring the diameters of the corresponding inhibition zones, followed by determination of the Minimum Inhibitory Concentration (MIC) (using metronidazole, and amoxicillin as control antibiotics) and the rate of kill. Preliminary phytochemical screening was also done. Inhibition zone diameters which ranged from 0–23 mm were observed for all five of the extracts and 0–35 mm for clarithromycin. Marked susceptibility of strains (100%) was noted for the acetone extract (P < 0.05), followed by ethyl acetate extract (93.5%). The MIC50 values ranged from 0.0048 to 0.156 mg/mL for the ethyl acetate extract and 0.0048 to 0.313 mg/mL for the acetone extract. The MIC90 values ranged from 0.0048 to 2.5 mg/mL for the ethyl acetate extract and 0.078 to >0.625 mg/mL for the acetone extract, respectively. Insignificant statistical difference in potency was observed when comparing the crude ethyl acetate extract to metronidazole and amoxicillin (P > 0.05). Complete killing of strain PE430C by the ethyl acetate extract was observed at 0.1 mg/mL (2 × MIC) and 0.2 mg/mL (4 × MIC) at 66 and 72 h. For strain PE369C, 100% killing was observed at 0.1 mg/mL (2 × MIC) in 66 and 72 h. The ethyl acetate extract could thus be a potential source of lead molecules for the design of new anti-Helicobacter pylori therapies as this study further confirmed the presence of phytochemicals including alkaloids, flavonoids, steroids, tannins and saponins. Full article
(This article belongs to the Section Natural Products)
Open AccessArticle New 3′,8′′-Linked Biflavonoids from Selaginella uncinata Displaying Protective Effect against Anoxia
Molecules 2011, 16(8), 6206-6214; doi:10.3390/molecules16086206
Received: 27 June 2011 / Revised: 12 July 2011 / Accepted: 21 July 2011 / Published: 25 July 2011
Cited by 18 | PDF Full-text (530 KB)
Abstract
Seven 3′,8′′-linked bioflavonoids, including one new compound, (2′′S)-2′′, 3′′-dihydroamentoflavone-4′-methyl ether (1) and six known compounds: (2S)-2,3- dihydroamentoflavone-4′-methyl ether (2), (2S,2′′S)-2,3,2′′,3′′-tetrahydroamento- flavone-4′-methyl ether (3), (2S,2′′S)-tetrahydroamentoflavone [...] Read more.
Seven 3′,8′′-linked bioflavonoids, including one new compound, (2′′S)-2′′, 3′′-dihydroamentoflavone-4′-methyl ether (1) and six known compounds: (2S)-2,3- dihydroamentoflavone-4′-methyl ether (2), (2S,2′′S)-2,3,2′′,3′′-tetrahydroamento- flavone-4′-methyl ether (3), (2S,2′′S)-tetrahydroamentoflavone (4), (2S)-2,3-dihydro- amentoflavone (5) and (2′′S)-2′′,3′′-dihydroamentoflavone (6) and amentoflavone (7), were isolated from the 60% ethanolic extract of Selaginella uncinata (Desv.) Spring. The structures of these compounds were elucidated mainly by analysis of their 1D and 2D NMR spectroscopic data, and their absolute configurations were determined by circular-dichroism (CD) spectroscopy. All the seven compounds showed protective effect against anoxia in the anoxic PC12 cells assay, in which compound 6 displayed particularly potent activity. Full article
Figures

Open AccessArticle The Suzuki Reaction in Aqueous Media Promoted by P, N Ligands
Molecules 2011, 16(8), 6215-6231; doi:10.3390/molecules16086215
Received: 8 June 2011 / Revised: 19 July 2011 / Accepted: 20 July 2011 / Published: 25 July 2011
Cited by 12 | PDF Full-text (620 KB)
Abstract
The synthesis and structure of palladium complexes of trisubstituted PTA derivatives, PTAR3, are described. Water-soluble phosphine ligands 1,3,5-triaza-7-phosphaadmantane (PTA), tris(aminomethyl)phosphine trihydrobromide, tri(aminomethyl) phosphine, 3,7-dimethyl-1,5,7-triaza-3-phosphabicyclo[3,3,1]nonane (RO-PTA), 3,7-diacetyl-1,3,7-triaza-5-phosphabicyclo[3.3.1]nonane (DAPTA), lithium 1,3,5-triaza-7-phosphaadamantane-6-carboxylate (PTA-CO2Li), 2,4,6-triphenyl-1,3,5-triaza-7-phosphatricyclo [3.3.1.1]decane, and 2,4,6-triphenyl-1,3,5-triaza-7-phosphatricyclo[3.3.1.1]decane were used as ligands for [...] Read more.
The synthesis and structure of palladium complexes of trisubstituted PTA derivatives, PTAR3, are described. Water-soluble phosphine ligands 1,3,5-triaza-7-phosphaadmantane (PTA), tris(aminomethyl)phosphine trihydrobromide, tri(aminomethyl) phosphine, 3,7-dimethyl-1,5,7-triaza-3-phosphabicyclo[3,3,1]nonane (RO-PTA), 3,7-diacetyl-1,3,7-triaza-5-phosphabicyclo[3.3.1]nonane (DAPTA), lithium 1,3,5-triaza-7-phosphaadamantane-6-carboxylate (PTA-CO2Li), 2,4,6-triphenyl-1,3,5-triaza-7-phosphatricyclo [3.3.1.1]decane, and 2,4,6-triphenyl-1,3,5-triaza-7-phosphatricyclo[3.3.1.1]decane were used as ligands for palladium catalyzed Suzuki reactions in aqueous media. RO-PTA in combination with palladium acetate or palladium chloride was the most active catalyst for Suzuki cross coupling of aryl bromides and phenylboronic acid at 80 °C in 1:1 water:acetonitrile. The activity of Pd(II) complexes of RO-PTA is comparable to PPh2(m-C6H4SO3Na) (TPPMS) and P(m-C6H4SO3Na)3 (TPPTS) and less active than tri(4,6-dimethyl-3-sulfonatophenyl)phosphine trisodium salt (TXPTS). Activated, deactivated, and sterically hindered aryl bromides were examined, with yields ranging from 50% to 90% in 6 h with 5% palladium precatalyst loading. X-ray crystal structures of (RO-PTA)PdCl2, (PTAR3)2PdCl2 (R = Ph, p-tert-butylC6H5), and PTAR3 (R = p-tert-butylC6H5) are reported. Full article
(This article belongs to the Special Issue Organometallic Chemistry)
Open AccessCommunication Antiradical, Chelating and Antioxidant Activities of Hydroxamic Acids and Hydroxyureas
Molecules 2011, 16(8), 6232-6242; doi:10.3390/molecules16086232
Received: 19 May 2011 / Revised: 13 July 2011 / Accepted: 20 July 2011 / Published: 25 July 2011
Cited by 20 | PDF Full-text (533 KB)
Abstract
Reactive oxygen species, along with reactive nitrogen species, may play an important role in the pathogenesis and progress of many diseases, including cancer, diabetes and sickle cell disease. It has been postulated that hydroxyurea, one of the main treatments in sickle cell [...] Read more.
Reactive oxygen species, along with reactive nitrogen species, may play an important role in the pathogenesis and progress of many diseases, including cancer, diabetes and sickle cell disease. It has been postulated that hydroxyurea, one of the main treatments in sickle cell disease, achieves its activity partly also through its antioxidant properties. A series of hydroxyurea derivatives of L- and D-amino acid amides and cycloalkyl-N-aryl-hydroxamic acids was synthesized and investigated for their radical scavenging activity, chelating properties and antioxidant activity. All the compounds showed exceptional antiradical activities. For example, free radical scavenging activities of investigated hydroxyureas were higher than the activity of standard antioxidant, butylated hydroxyanisole (BHA). Moreover, most of the investigated hydroxamic acids were stronger Fe2+ ion chelators than quercetin. In addition, the investigated compounds, especially hydroxamic acids, were proven to be excellent antioxidants. They were as effective as BHA in inhibiting b-carotene-linoleic acid coupled oxidation. It is reasonable to assume that the antioxidant activity of the investigated compounds could contribute to their previously proven biological properties as cytostatic and antiviral agents. Full article
Open AccessArticle Anticancer Activity of Chamaejasmine: Effect on Tubulin Protein
Molecules 2011, 16(8), 6243-6254; doi:10.3390/molecules16086243
Received: 28 June 2011 / Revised: 15 July 2011 / Accepted: 18 July 2011 / Published: 25 July 2011
Cited by 7 | PDF Full-text (807 KB)
Abstract
In this work, the anticancer activity of chamaejasmine was studied by evaluating its in vitro cytotoxicity against several human cancer cell lines (MCF-7, A549, SGC-7901, HCT-8, HO-4980, Hela, HepG2, PC-3, LNCap, Vero and MDCK) using the MTT assay. Results indicated chamaejasmine showed [...] Read more.
In this work, the anticancer activity of chamaejasmine was studied by evaluating its in vitro cytotoxicity against several human cancer cell lines (MCF-7, A549, SGC-7901, HCT-8, HO-4980, Hela, HepG2, PC-3, LNCap, Vero and MDCK) using the MTT assay. Results indicated chamaejasmine showed more notable anticancer activity than taxol against PC-3 cells, with IC50 values of 2.28 and 3.98 µM, respectively. Furthermore, Western blot analysis showed that chamaejasmine was able to increase the expression of β-tubulin, but not α-tubulin. In silico simulations indicated that chamaejasmine specifically interacts with the active site which is located at the top of β-tubulin, thanks to the presence of strong hydrophobic effects between the core templates and the hydrophobic surface of the TB active site. The binding energy (Einter) was calculated to be −164.77 kcal·mol−1. Results presented here suggest that chamaejasmine possesses anti-cancer properties relating to β-tubulin depolymerization inhibition, and therefore is a potential source of anticancer leads for the pharmaceutical industry. Full article
Open AccessArticle The Inhibitory Potential of Thai Mango Seed Kernel Extract against Methicillin-Resistant Staphylococcus Aureus
Molecules 2011, 16(8), 6255-6270; doi:10.3390/molecules16086255
Received: 28 June 2011 / Revised: 18 July 2011 / Accepted: 20 July 2011 / Published: 25 July 2011
Cited by 7 | PDF Full-text (787 KB)
Abstract
Plant extracts are a valuable source of novel antibacterial compounds to combat pathogenic isolates of methicillin-resistant Staphylococcus aureus (MRSA), a global nosocomial infection. In this study, the alcoholic extract from Thai mango (Mangifera indica L. cv. ‘Fahlun’) seed kernel extract (MSKE) [...] Read more.
Plant extracts are a valuable source of novel antibacterial compounds to combat pathogenic isolates of methicillin-resistant Staphylococcus aureus (MRSA), a global nosocomial infection. In this study, the alcoholic extract from Thai mango (Mangifera indica L. cv. ‘Fahlun’) seed kernel extract (MSKE) and its phenolic principles (gallic acid, methyl gallate and pentagalloylglucopyranose) demonstrated potent in vitro antibacterial activity against Staphylococcus aureus and 19 clinical MRSA isolates in studies of disc diffusion, broth microdilution and time-kill assays. Electron microscopy studies using scanning electron microscopy and transmission electron microscopy revealed impaired cell division and ultra-structural changes in bacterial cell morphology, including the thickening of cell walls, of microorganisms treated with MSKE; these damaging effects were increased with increasing concentrations of MSKE. MSKE and its phenolic principles enhanced and intensified the antibacterial activity of penicillin G against 19 clinical MRSA isolates by lowering the minimum inhibitory concentration by at least 5-fold. The major phenolic principle, pentagalloylglucopyranose, was demonstrated to be the major contributor to the antibacterial activity of MSKE. These results suggest that MSKE may potentially be useful as an alternative therapeutic agent or an adjunctive therapy along with penicillin G in the treatment of MRSA infections. Full article
(This article belongs to the Section Natural Products)
Open AccessArticle Design and Synthesis of Novel Antimicrobial Acyclic and Heterocyclic Dyes and Their Precursors for Dyeing and/or Textile Finishing Based on 2-N-Acylamino-4,5,6,7-tetrahydro-benzo[b]thiophene Systems
Molecules 2011, 16(8), 6271-6305; doi:10.3390/molecules16086271
Received: 22 May 2011 / Revised: 4 July 2011 / Accepted: 4 July 2011 / Published: 26 July 2011
Cited by 12 | PDF Full-text (587 KB)
Abstract
A series of novel polyfunctionalized acyclic and heterocyclic dye precursors and their respective azo (hydrazone) counterpart dyes and dye precursors based on conjugate enaminones and/or enaminonitrile moieties were synthesized. The dyes and their precursors are based on 2-cyano-N-(3-cyano-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)-acetamide, [...] Read more.
A series of novel polyfunctionalized acyclic and heterocyclic dye precursors and their respective azo (hydrazone) counterpart dyes and dye precursors based on conjugate enaminones and/or enaminonitrile moieties were synthesized. The dyes and their precursors are based on 2-cyano-N-(3-cyano-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)-acetamide, 2-ethoxycarbonyl-N-(3-cyano-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)-acetamide or 2-phenylcarbamoyl-N-(3-cyano-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)-acetamide systems as precursors. The latter compounds were used to synthesize polyfunctional thiophene-, thiazole-, pyrazole, pyridine-, pyrimidine-, oxazine-, as well as acyclic moieties. The dyes and dye precursors were characterized by elemental analysis and spectral methods. All dyes and their precursors were screened in vitro and evaluated for both their antibacterial and antifungal activities. MIC data of the novel dye systems and their respective precursors showed significant antimicrobial activity against most tested organisms. Some compounds exhibited comparable or even higher efficiency than selected standards. Dyes were applied at 5% depth for disperse dyeing of nylon, acetate and polyester fabrics. Their spectral characteristics and fastness properties were measured and evaluated. Full article
Figures

Open AccessArticle Synthesis of Both Ionic Species of Ammonium Dithiocarbamate Derived Cholic Acid Moieties
Molecules 2011, 16(8), 6306-6312; doi:10.3390/molecules16086306
Received: 1 July 2011 / Revised: 18 July 2011 / Accepted: 25 July 2011 / Published: 26 July 2011
Cited by 3 | PDF Full-text (417 KB)
Abstract
The reaction of 3-aminopropylamide of cholic acid with CS2 produced a bile acid derivative of dithiocarbamic acid which further formed an ammonium salt with another molecule of 3-aminopropylamide of cholic acid. The cationic 3-ammonium propylamide of cholic acid did not react [...] Read more.
The reaction of 3-aminopropylamide of cholic acid with CS2 produced a bile acid derivative of dithiocarbamic acid which further formed an ammonium salt with another molecule of 3-aminopropylamide of cholic acid. The cationic 3-ammonium propylamide of cholic acid did not react further with CS2 and the formed salt was stable in the reaction mixture, even when excess CS2 was used. When the reaction was carried out in the presence of aqueous sodium hydroxide, only the bile acid derivative of sodium dithiocarbamate was formed. The dithiocarbamate derivatives were characterized by 1H- and 13C-NMR spectroscopy and ESI-TOF mass spectrometry. Full article
(This article belongs to the Special Issue Steroids)
Figures

Open AccessCommunication A Facile Synthesis of Highly Functionalized 4-Arylcoumarins via Kostanecki Reactions Mediated by DBU
Molecules 2011, 16(8), 6313-6321; doi:10.3390/molecules16086313
Received: 1 July 2011 / Revised: 19 July 2011 / Accepted: 22 July 2011 / Published: 26 July 2011
Cited by 6 | PDF Full-text (354 KB)
Abstract
An efficient synthesis of 4-arylcoumarins has been accomplished via Kostanecki reactions of 2-hydroxybenzophenones with acetic anhydride employing DBU at ambient temperature. Using the same strategy, several 2-acyloxybenzophenone derivatives were readily converted to 3,4-difunctionalized coumarins. This protocol offers a notable improvement in reaction [...] Read more.
An efficient synthesis of 4-arylcoumarins has been accomplished via Kostanecki reactions of 2-hydroxybenzophenones with acetic anhydride employing DBU at ambient temperature. Using the same strategy, several 2-acyloxybenzophenone derivatives were readily converted to 3,4-difunctionalized coumarins. This protocol offers a notable improvement in reaction conditions for coumarin synthesis and takes advantage of its synthetic capability, especially for highly functionalized 4-arylcoumarins with structural diversity. Full article
Figures

Open AccessArticle Rhinacanthus nasutus Protects Cultured Neuronal Cells against Hypoxia Induced Cell Death
Molecules 2011, 16(8), 6322-6338; doi:10.3390/molecules16086322
Received: 20 July 2011 / Accepted: 21 July 2011 / Published: 26 July 2011
Cited by 13 | PDF Full-text (500 KB)
Abstract
Rhinacanthus nasutus (L.) Kurz (Acanthaceae) is an herb native to Thailand and Southeast Asia, known for its antioxidant properties. Hypoxia leads to an increase in reactive oxygen species in cells and is a leading cause of neuronal damage. Cell death caused by [...] Read more.
Rhinacanthus nasutus (L.) Kurz (Acanthaceae) is an herb native to Thailand and Southeast Asia, known for its antioxidant properties. Hypoxia leads to an increase in reactive oxygen species in cells and is a leading cause of neuronal damage. Cell death caused by hypoxia has been linked with a number of neurodegenerative diseases including some forms of dementia and stroke, as well as the build up of reactive oxygen species which can lead to diseases such as Huntington’s disease, Parkinson’s disease and Alzeheimer’s disease. In this study we used an airtight culture container and the Mitsubishi Gas Company anaeropack along with the MTT assay, LDH assay and the trypan blue exlusion assay to show that 1 and 10 µg mL−1 root extract of R. nasutus is able to significantly prevent the death of HT-22 cells subjected to hypoxic conditions, and 0.1 to 10 µg mL−1 had no toxic effect on HT-22 under normal conditions, whereas 100 µg mL−1 reduced HT-22 cell proliferation. We also used H2DCFDA staining to show R. nasutus can reduce reactive oxygen species production in HT-22 cells. Full article
(This article belongs to the Section Medicinal Chemistry)
Open AccessArticle Furocoumarin Derivatives from Radix Angelicae Dahuricae and Their Effects on RXRα Transcriptional Regulation
Molecules 2011, 16(8), 6339-6348; doi:10.3390/molecules16086339
Received: 12 May 2011 / Revised: 5 July 2011 / Accepted: 14 July 2011 / Published: 26 July 2011
Cited by 10 | PDF Full-text (482 KB)
Abstract
A novel furocoumarin derivative named oxyalloimperatorin (1), together with seventeen furocoumarins 2–18 were isolated from the radix of Angelica dahurica. The chemical structure of new metabolite was characterized by analysis of IR, NMR, and HR-ESI-MS spectroscopic data. Among the [...] Read more.
A novel furocoumarin derivative named oxyalloimperatorin (1), together with seventeen furocoumarins 2–18 were isolated from the radix of Angelica dahurica. The chemical structure of new metabolite was characterized by analysis of IR, NMR, and HR-ESI-MS spectroscopic data. Among the isolated compounds, 13, 16, and 18 (each at 20 μM) could significantly promote the gene transcriptional function of nuclear receptor RXRα. While 79, 13, 14, and the new structure 1 (each at 20 μM) showed significant reduction in RXRα gene transcriptional activities induced by 9-cis-retinoid acid. The findings indicated that these furocoumarin skeleton derivatives might hold beneficial effects on many intractable diseases, such as cancer and metabolic diseases, due to their potential activities on regulating the transcriptional activation function of RXRα. Full article
(This article belongs to the Section Natural Products)
Open AccessArticle Novel Library of Selenocompounds as Kinase Modulators
Molecules 2011, 16(8), 6349-6364; doi:10.3390/molecules16086349
Received: 30 June 2011 / Revised: 20 July 2011 / Accepted: 22 July 2011 / Published: 27 July 2011
Cited by 12 | PDF Full-text (710 KB) | Supplementary Files
Abstract
Although the causes of cancer lie in mutations or epigenic changes at the genetic level, their molecular manifestation is the dysfunction of biochemical pathways at the protein level. The 518 protein kinases encoded by the human genome play a central role in [...] Read more.
Although the causes of cancer lie in mutations or epigenic changes at the genetic level, their molecular manifestation is the dysfunction of biochemical pathways at the protein level. The 518 protein kinases encoded by the human genome play a central role in various diseases, a fact that has encouraged extensive investigations on their biological function and three dimensional structures. Selenium (Se) is an important nutritional trace element involved in different physiological functions with antioxidative, antitumoral and chemopreventive properties. The mechanisms of action for selenocompounds as anticancer agents are not fully understood, but kinase modulation seems to be a possible pathway. Various organosulfur compounds have shown antitumoral and kinase inhibition effects but, in many cases, the replacement of sulfur by selenium improves the antitumoral effect of compounds. Although Se atom possesses a larger atomic volume and nucleophilic character than sulfur, Se can also formed interactions with aminoacids of the catalytic centers of proteins. So, we propose a novel chemical library that includes organoselenium compounds as kinase modulators. In this study thirteen selenocompounds have been evaluated at a concentration of 3 or 10 µM in a 24 kinase panel using a Caliper LabChip 3000 Drug Discover Platform. Several receptor (EGFR, IGFR1, FGFR1…) and non-receptor (Abl) kinases have been selected, as well as serine/threonine/lipid kinases (AurA, Akt, CDKs, MAPKs…) implicated in main cancer pathways: cell cycle regulation, signal transduction, angiogenesis regulation among them. The obtained results showed that two compounds presented inhibition values higher than 50% in at least four kinases and seven derivatives selectively inhibited one or two kinases. Furthermore, three compounds selectively activated IGF-1R kinase with values ranging from −98% to −211%. In conclusion, we propose that the replacement of sulfur by selenium seems to be a potential and useful strategy in the search of novel chemical compound libraries against cancer as kinase modulators. Full article
(This article belongs to the Special Issue Chemical Libraries)
Open AccessArticle Effects of Lipoic Acid, Caffeic Acid and a Synthesized Lipoyl-Caffeic Conjugate on Human Hepatoma Cell Lines
Molecules 2011, 16(8), 6365-6377; doi:10.3390/molecules16086365
Received: 10 June 2011 / Revised: 22 July 2011 / Accepted: 26 July 2011 / Published: 27 July 2011
Cited by 21 | PDF Full-text (2325 KB) | Supplementary Files
Abstract
Hepatocellular carcinoma (HCC) is among the most aggressive and fatal cancers. Its treatment with conventional chemotherapeutic agents is inefficient, due to several side effects linked to impaired organ function typical of liver diseases. Consequently, there exists a decisive requirement to explore possible [...] Read more.
Hepatocellular carcinoma (HCC) is among the most aggressive and fatal cancers. Its treatment with conventional chemotherapeutic agents is inefficient, due to several side effects linked to impaired organ function typical of liver diseases. Consequently, there exists a decisive requirement to explore possible alternative chemopreventive and therapeutic strategies. The use of dietary antioxidants and micronutrients has been proposed for HCC successful management. The aim of this work was to test in vitro the effects of lipoic acid, caffeic acid and a new synthesized lipoyl-caffeic conjugate on human hepatoma cell lines in order to assess their effect on tumor cell growth. The results of cytotoxicity assays at different times showed that the cell viability was directly proportional to the molecule concentrations and incubation times. Moreover, to evaluate the pro- or anti-inflammatory effects of these molecules, the cytokine concentrations were evaluated in treated and untreated cellular supernatants. The obtained cytokine pattern showed that, at the increasing of three molecules concentrations, three pro-inflammatory cytokines such as IL-1β, IL-8 and TNF-α decreased whereas the anti-inflammatory cytokine such as IL-10 increased. Full article
Open AccessArticle Antioxidant Capacities and Total Phenolic Contents Increase with Gamma Irradiation in Two Types of Malaysian Honey
Molecules 2011, 16(8), 6378-6395; doi:10.3390/molecules16086378
Received: 25 May 2011 / Revised: 21 July 2011 / Accepted: 25 July 2011 / Published: 27 July 2011
Cited by 32 | PDF Full-text (469 KB)
Abstract
Two types of monofloral Malaysian honey (Gelam and Nenas) were analyzed to determine their antioxidant activities and total phenolic and flavonoid contents, with and without gamma irradiation. Our results showed that both types of honey can scavenge free radicals and exhibit high antioxidant-reducing power; however, Gelam honey exhibited higher antioxidant activity (p < 0.05) than Nenas honey, which is in good correlation (r = 0.9899) with its phenolic contents. Interestingly, we also noted that both irradiated honeys have higher antioxidant activities and total phenolic and flavonoid contents compared to nonirradiated honeys by Folin-Ciocalteu and UV-spectrophotometry methods, respectively. However, HPLC analysis for phenolic compounds showed insignificant increase between irradiated and nonirradiated honeys. The phenolic compounds such as: caffeic acid, chlorogenic acid, ellagic acid, p- coumaric acid, quercetin and hesperetin as indicated by HPLC method were found to be higher in Gelam honey versus Nenas honey. In conclusion, irradiation of honey causes enhanced antioxidant activities and flavonoid compounds. Full article
(This article belongs to the Section Natural Products)
Open AccessArticle Substrate Promiscuity of N-Acetylhexosamine 1-Kinases
Molecules 2011, 16(8), 6396-6407; doi:10.3390/molecules16086396
Received: 1 July 2011 / Revised: 22 July 2011 / Accepted: 25 July 2011 / Published: 28 July 2011
Cited by 23 | PDF Full-text (628 KB)
Abstract
N-Acetylhexosamine 1-kinase (NahK) catalyzes the direct addition of a phosphate from adenosine 5'-triphosphate (ATP) to the anomeric position of N-acetylhexosamine and shows similar activity towards N-acetylglucosamine (GlcNAc) and N-acetylgalactosamine (GalNAc). Herein we report the cloning, characterization, and substrate [...] Read more.
N-Acetylhexosamine 1-kinase (NahK) catalyzes the direct addition of a phosphate from adenosine 5'-triphosphate (ATP) to the anomeric position of N-acetylhexosamine and shows similar activity towards N-acetylglucosamine (GlcNAc) and N-acetylgalactosamine (GalNAc). Herein we report the cloning, characterization, and substrate specificity studies of two NahKs from Bifidobacterium infantis ATCC15697 and Bifidobacterium longum ATCC55813, respectively. A new capillary electrophoresis assay method has been developed for enzyme activity assays. Both enzymes have a good expression level in E. coli (180–185 mg/L culture) and can tolerate diverse modifications at C2 of GlcNAc and GalNAc. Various GlcNAc derivatives with C6, both C2 and C6, as well as both C2 and C3 modifications are tolerable substrates for the newly cloned NahKs. Quite interestingly, despite of their low activities toward glucose and galactose, the activities of both NahKs are much higher for mannose and some of its C2, C4, and C6 derivatives. These NahKs are excellent catalysts for enzymatic and chemoenzymatic synthesis of carbohydrates. Full article
(This article belongs to the Special Issue Enzyme-Catalyzed Reactions)
Figures

Open AccessArticle Synthesis and Toxicity Evaluation of Some N4-Aryl Substituted 5-Trifluoromethoxyisatin-3-thiosemicarbazones
Molecules 2011, 16(8), 6408-6421; doi:10.3390/molecules16086408
Received: 16 June 2011 / Revised: 13 July 2011 / Accepted: 22 July 2011 / Published: 29 July 2011
Cited by 3 | PDF Full-text (446 KB) | Supplementary Files
Abstract
A series of twenty one N4-aryl substituted 5-trifluoromethoxyisatin-3-thiosemicarbazones 3a-3u was synthesized by the reaction of trifluoromethoxyisatin 1 with different arylthiosemicarbazides 2 in aqueous ethanol (50%), containing a few drops of acetic acid. Their structures were established on the basis of [...] Read more.
A series of twenty one N4-aryl substituted 5-trifluoromethoxyisatin-3-thiosemicarbazones 3a-3u was synthesized by the reaction of trifluoromethoxyisatin 1 with different arylthiosemicarbazides 2 in aqueous ethanol (50%), containing a few drops of acetic acid. Their structures were established on the basis of analytical (CHN) and spectral (IR, 1H-NMR, EIMS) data. All the synthesized compounds were evaluated for their toxicity potential by a brine shrimp lethality bioassay. Ten compounds i.e., 3a, 3e, 3i-3l and 3n-3q proved to be active in this assay, displaying promising toxicity (LD50 = 1.11 × 10−5 M − 1.80 × 10−4 M). Amongst these, 3k, 3n and 3o were found to be the most active ones (LD50 = 1.11 × 10−5 M − 1.43 × 10−5 M). Compound 3k showed the highest activity with a LD50 value of 1.11 × 10−5 M and can, therefore, be used as a lead for further studies. Structure-activity relationship (SAR) studies revealed that the presence of strong inductively electron-attracting trifluoromethoxy substituent at position-5 of the isatin moiety played an important role in inducing or enhancing toxic potentiality of some of the synthesized compounds. Full article
Open AccessArticle Alkylphenol Activity against Candida spp. and Microsporum canis: A Focus on the Antifungal Activity of Thymol, Eugenol and O-Methyl Derivatives
Molecules 2011, 16(8), 6422-6431; doi:10.3390/molecules16086422
Received: 11 May 2011 / Revised: 15 July 2011 / Accepted: 26 July 2011 / Published: 29 July 2011
Cited by 9 | PDF Full-text (390 KB)
Abstract
In recent years there has been an increasing search for new antifungal compounds due to the side effects of conventional antifungal drugs and fungal resistance. The aims of this study were to test in vitro the activity of thymol, eugenol, estragole and [...] Read more.
In recent years there has been an increasing search for new antifungal compounds due to the side effects of conventional antifungal drugs and fungal resistance. The aims of this study were to test in vitro the activity of thymol, eugenol, estragole and anethole and some O-methyl-derivatives (methylthymol and methyleugenol) against Candida spp. and Microsporum canis. The broth microdilution method was used to determine the minimum inhibitory concentration (MIC). The minimum fungicidal concentrations (MFC) for both Candida spp. and M. canis were found by subculturing each fungal suspension on potato dextrose agar. Thymol, methylthymol, eugenol, methyl-eugenol, anethole, estragole and griseofulvin respectively, presented the following MIC values against M. canis: 4.8–9.7; 78–150; 39; 78–150; 78–150; 19–39 µg/mL and 0.006–2.5 mg/mL. The MFC values for all compounds ranged from 9.7 to 31 µg/mL. Concerning Candida spp, thymol, methylthymol, eugenol, methyleugenol, anethole, estragole and amphotericin, respectively, showed the following MIC values: 39; 620–1250; 150–620; 310–620; 620; 620–1250 and 0.25–2.0 mg/mL. The MFC values varied from 78 to 2500 µg/mL. All tested compounds thus showed in vitro antifungal activity against Candida spp. and M. canis. Therefore, further studies should be carried out to confirm the usefulness of these alkylphenols in vivo. Full article
Open AccessCommunication A New C-3/C-3”-Biflavanone from the Roots of Stellera chamaejasme L
Molecules 2011, 16(8), 6465-6469; doi:10.3390/molecules16086465
Received: 1 July 2011 / Revised: 9 July 2011 / Accepted: 19 July 2011 / Published: 29 July 2011
Cited by 9 | PDF Full-text (431 KB)
Abstract A new 3, 3”-biflavanone, neochamaejasmin C (1), was isolated from the roots of Stellera chamaejasme L., together with four known compounds. Their structures and configurations were elucidated by spectroscopic methods, including 2D-NMR techniques. Full article
Open AccessArticle Expeditious Entry to Novel 2-Methylene-2,3-dihydrofuro[3,2-c] chromen-2-ones from 6-Chloro-4-hydroxychromen-2-one and Propargylic Alcohols
Molecules 2011, 16(8), 6470-6480; doi:10.3390/molecules16086470
Received: 14 July 2011 / Revised: 27 July 2011 / Accepted: 28 July 2011 / Published: 2 August 2011
Cited by 5 | PDF Full-text (366 KB)
Abstract A catalytic system consisting of the ruthenium(II) complex [Ru(η3-2-C3H4Me)(CO)(dppf)][SbF6] (dppf = 1,1’-bis(diphenylphosphino)ferrocene) and trifluoroacetic acid has been used to promote the coupling of secondary propargylic alcohols with 6-chloro-4-hydroxychromen-2-one. The reactions afforded unusual 2-methylene-2,3-dihydrofuro[3,2-c]chromen-2-ones in good yields. Full article
(This article belongs to the Special Issue Heterocycles)
Figures

Open AccessArticle Phenylacetonitrile from the Giant Knotweed, Fallopia sachalinensis, Infested by the Japanese Beetle, Popillia japonica, Is Induced by Exogenous Methyl Jasmonate
Molecules 2011, 16(8), 6481-6488; doi:10.3390/molecules16086481
Received: 4 July 2011 / Revised: 28 July 2011 / Accepted: 2 August 2011 / Published: 3 August 2011
Cited by 4 | PDF Full-text (339 KB)
Abstract
Phenylacetonitrile, (E)-b-ocimene, linalool, (E)-4,8-dimethyl-1,3,7-nonatriene and (E,E)-a-farnesene were identified as Japanese beetle, Popillia japonica, feeding-induced volatiles from the leaves of the giant knotweed, Fallopia sachalinensis, but not by mechanical damage. Volatile emission was [...] Read more.
Phenylacetonitrile, (E)-b-ocimene, linalool, (E)-4,8-dimethyl-1,3,7-nonatriene and (E,E)-a-farnesene were identified as Japanese beetle, Popillia japonica, feeding-induced volatiles from the leaves of the giant knotweed, Fallopia sachalinensis, but not by mechanical damage. Volatile emission was also induced by treatment with a cellular signaling molecule, methyl jasmonate. These results suggest that volatiles will be synthesized de novo by a biotic elicitor from P. japonica oral secretion. Full article
(This article belongs to the Section Natural Products)
Figures

Open AccessArticle Inhibitory Effect and Possible Mechanism of Action of Patchouli Alcohol against Influenza A (H2N2) Virus
Molecules 2011, 16(8), 6489-6501; doi:10.3390/molecules16086489
Received: 13 May 2011 / Revised: 25 July 2011 / Accepted: 28 July 2011 / Published: 3 August 2011
Cited by 7 | PDF Full-text (535 KB)
Abstract
In the present study, the anti-influenza A (H2N2) virus activity of patchouli alcohol was studied in vitro, in vivo and in silico. The CC50 of patchouli alcohol was above 20 µM. Patchouli alcohol could inhibit influenza virus with an [...] Read more.
In the present study, the anti-influenza A (H2N2) virus activity of patchouli alcohol was studied in vitro, in vivo and in silico. The CC50 of patchouli alcohol was above 20 µM. Patchouli alcohol could inhibit influenza virus with an IC50 of 4.03 ± 0.23 µM. MTT assay showed that the inhibition by patchouli alcohol appears strongly after penetration of the virus into the cell. In the influenza mouse model, patchouli alcohol showed obvious protection against the viral infection at a dose of 5 mg/kg/day. Flexible docking and molecular dynamic simulations indicated that patchouli alcohol was bound to the neuraminidase protein of influenza virus, with an interaction energy of –40.38 kcal mol–1. The invariant key active-site residues Asp151, Arg152, Glu119, Glu276 and Tyr406 played important roles during the binding process. Based on spatial and energetic criteria, patchouli alcohol interfered with the NA functions. Results presented here suggest that patchouli alcohol possesses anti-influenza A (H2N2) virus properties, and therefore is a potential source of anti-influenza agents for the pharmaceutical industry. Full article
Open AccessArticle 1,1’-(3-Methyl-4-phenylthieno[2,3-b]thiophene-2,5-diyl)diethanone as a Building Block in Heterocyclic Synthesis. Novel Synthesis of Some Pyrazole and Pyrimidine Derivatives
Molecules 2011, 16(8), 6502-6511; doi:10.3390/molecules16086502
Received: 20 June 2011 / Revised: 25 July 2011 / Accepted: 29 July 2011 / Published: 3 August 2011
Cited by 16 | PDF Full-text (430 KB)
Abstract
A series of new bis(heterocycles) featuring thieno[2,3-b]thiophene rings was synthesized in a combinatorial manner. Intramolecular cyclization of enaminone derivatives with appropriate N-nucleophiles afforded the target compounds. All compounds were characterized by 1H-, 13C-NMR, GCMS, IR, and UV-Vis [...] Read more.
A series of new bis(heterocycles) featuring thieno[2,3-b]thiophene rings was synthesized in a combinatorial manner. Intramolecular cyclization of enaminone derivatives with appropriate N-nucleophiles afforded the target compounds. All compounds were characterized by 1H-, 13C-NMR, GCMS, IR, and UV-Vis spectrometry. These compounds represent a new class of sulfur- and nitrogen-containing heterocycles that should also be of interest as new materials. Full article
(This article belongs to the Special Issue Heterocycles)
Figures

Open AccessArticle Perfluoro Allyl Fluorosulfate (FAFS): A Versatile Building Block for New Fluoroallylic Compounds
Molecules 2011, 16(8), 6512-6540; doi:10.3390/molecules16086512
Received: 27 June 2011 / Revised: 22 July 2011 / Accepted: 29 July 2011 / Published: 4 August 2011
Cited by 5 | PDF Full-text (932 KB)
Abstract
In this study we will present and discuss both the synthesis of CF2=CFCF2OSO2F (perfluoroallyl fluorosulfate, FAFS), focusing in particular on the important role of C3F6/SO3 ratio, reaction temperature and boron catalyst/SO [...] Read more.
In this study we will present and discuss both the synthesis of CF2=CFCF2OSO2F (perfluoroallyl fluorosulfate, FAFS), focusing in particular on the important role of C3F6/SO3 ratio, reaction temperature and boron catalyst/SO3 ratio on FAFS’ yield and selectivity, as well as a wide variety of ionic and radical reactions possible with FAFS. We focused our attention on reactions of FAFS with aliphatic and aromatic alcohols, acyl halides, halides, H2O2, ketones and radicals whose synthesis and reaction mechanisms will be presented and discussed. Particular attention will be devoted to the novel diallyl-fluoroalkyl peroxide obtained. Factors such as pKa and Lowry and Pearson’s Hard/Soft Acid-Base Theory which determine the selectivity between Addition/Elimination vs. Nucleophilic Substitution reaction mechanisms on FAFS will also be presented and discussed. Full article
(This article belongs to the Special Issue Fluorine Chemistry 2016)
Figures

Open AccessArticle Rauniticine-allo-Oxindole B and Rauniticinic-allo Acid B, New Heteroyohimbine-Type Oxindole Alkaloids from the Stems of Malaysian Uncaria longiflora var. pteropoda
Molecules 2011, 16(8), 6541-6548; doi:10.3390/molecules16086541
Received: 20 June 2011 / Revised: 15 July 2011 / Accepted: 20 July 2011 / Published: 4 August 2011
Cited by 3 | PDF Full-text (374 KB)
Abstract Two new heteroyohimbine-type oxindole alkaloids, rauniticine-allo-oxindole B and rauniticinic-allo acid B, have been successfully isolated from the stems extract of Malaysian Uncaria longiflora var. pteropoda. The structures of the two new alkaloids were determined by spectroscopic analysis. Full article
(This article belongs to the Special Issue Alkaloids: Novel Therapeutic Perspectives)
Open AccessArticle Synthesis and Antimicrobial Activity of Some New Pyrazoles, Fused Pyrazolo[3,4-d]-pyrimidine and 1,2-Dihydroimidazo-[2,1-c][1,2,4]triazin-6-one Derivatives
Molecules 2011, 16(8), 6549-6560; doi:10.3390/molecules16086549
Received: 6 July 2011 / Revised: 25 July 2011 / Accepted: 28 July 2011 / Published: 4 August 2011
Cited by 26 | PDF Full-text (480 KB)
Abstract
A novel series of 7,7-diphenyl-1,2-dihydroimidazo[2,1-c][1,2,4]triazin-6(7H)-one 6a–h, were easily prepared via reactions of novel 2-hydrazinyl-4,4-diphenyl-1H-imidazol-5(4H)-one (2) with hydrazonoyl halides 3a–h. In addition, we also examined the reaction of compound 2 with [...] Read more.
A novel series of 7,7-diphenyl-1,2-dihydroimidazo[2,1-c][1,2,4]triazin-6(7H)-one 6a–h, were easily prepared via reactions of novel 2-hydrazinyl-4,4-diphenyl-1H-imidazol-5(4H)-one (2) with hydrazonoyl halides 3a–h. In addition, we also examined the reaction of compound 2 with commercially available active methylene compounds to afford new pyrazoles containing an imidazolone moiety, expected to be biologically active. The structures of the synthesized compounds were assigned on the basis of elemental analysis, IR, 1H-NMR and mass spectral data. The antifungal and antibacterial activities of the newly synthesized compounds were evaluated. Full article
(This article belongs to the Special Issue Heterocycles)
Open AccessArticle Synthesis of New Pentacyclo[5.4.0.02,6.03,10.05,9]undecane-8,11-dione (PCU) Cyanosilylated Derivatives Using Sulphated Zirconia and Hydrotalcite as Catalysts in Microwave-Assisted Reactions under Solvent Free Conditions
Molecules 2011, 16(8), 6561-6576; doi:10.3390/molecules16086561
Received: 10 June 2011 / Revised: 26 July 2011 / Accepted: 29 July 2011 / Published: 4 August 2011
Cited by 7 | PDF Full-text (1051 KB)
Abstract
A comparison was made of the effectiveness of the functionalization reactions of pentacyclo[5.4.0.02,6.03,10.05,9]undecane-8,11-dione (PCU) using sulphated zirconia in protection-deprotection reactions and Mg/Al hydrotalcite in a cyanosilylation reaction, under classical thermal conditions and imposing microwave radiation; improved [...] Read more.
A comparison was made of the effectiveness of the functionalization reactions of pentacyclo[5.4.0.02,6.03,10.05,9]undecane-8,11-dione (PCU) using sulphated zirconia in protection-deprotection reactions and Mg/Al hydrotalcite in a cyanosilylation reaction, under classical thermal conditions and imposing microwave radiation; improved yields and reaction times were considered. Full article
Open AccessArticle (+)-Kunstlerone, a New Antioxidant Neolignan from the Leaves of Beilschmiedia kunstleri Gamble
Molecules 2011, 16(8), 6582-6590; doi:10.3390/molecules16086582
Received: 31 May 2011 / Revised: 4 July 2011 / Accepted: 6 July 2011 / Published: 4 August 2011
Cited by 6 | PDF Full-text (683 KB)
Abstract
A new neolignan, 3,4-dimethoxy-3′,4′-methylenedioxy-2,9-epoxy-6,7-cyclo-1,8-neolign-11-en-5(5H)-one, which has been named (+)-kunstlerone (1), together with six known alkaloids: (+)-norboldine (2), (+)-N-methylisococlaurine (3), (+)-cassythicine (4), (+)-laurotetanine (5), (+)-boldine (6) and ( [...] Read more.
A new neolignan, 3,4-dimethoxy-3′,4′-methylenedioxy-2,9-epoxy-6,7-cyclo-1,8-neolign-11-en-5(5H)-one, which has been named (+)-kunstlerone (1), together with six known alkaloids: (+)-norboldine (2), (+)-N-methylisococlaurine (3), (+)-cassythicine (4), (+)-laurotetanine (5), (+)-boldine (6) and (-)-pallidine (7), were isolated from the leaves of Beilschmiedia kunstleri. The structures were established through various spectroscopic methods notably 1D- and 2D-NMR, UV, IR and LCMS-IT-TOF. (+)- Kunstlerone (1) showed a strong antioxidant activity, with an SC50 of 20.0 µg/mL. Full article
(This article belongs to the Section Natural Products)
Open AccessArticle Corydaline Inhibits Multiple Cytochrome P450 and UDP-Glucuronosyltransferase Enzyme Activities in Human Liver Microsomes
Molecules 2011, 16(8), 6591-6602; doi:10.3390/molecules16086591
Received: 22 June 2011 / Revised: 27 July 2011 / Accepted: 2 August 2011 / Published: 5 August 2011
Cited by 17 | PDF Full-text (574 KB)
Abstract
Corydaline is a bioactive alkaloid with various antiacetylcholinesterase, antiallergic, and antinociceptive activities found in the medicinal herb Corydalis Tubers. The inhibitory potential of corydaline on the activities of seven major human cytochrome P450 and four UDP-glucuronosyltransferase enzymes in human liver microsomes was [...] Read more.
Corydaline is a bioactive alkaloid with various antiacetylcholinesterase, antiallergic, and antinociceptive activities found in the medicinal herb Corydalis Tubers. The inhibitory potential of corydaline on the activities of seven major human cytochrome P450 and four UDP-glucuronosyltransferase enzymes in human liver microsomes was investigated using LC-tandem MS. Corydaline was found to inhibit CYP2C19-catalyzed S-mephenytoin-4’-hydroxylatoin and CYP2C9-catalyzed diclofenac 4-hydroxylation, with Ki values of 1.7 and 7.0 mM, respectively. Corydaline also demonstrated moderate inhibition of UGT1A1-mediated 17b-estradiol 3-glucuronidation and UGT1A9-mediated propofol glucuronidation with Ki values of 57.6 and 37.3 mM, respectively. In the presence of corydaline, CYP3A-mediated midazolam hydroxylation showed a decrease with increasing preincubation time in a dose-dependent manner with Ki values of 30.0 mM. These in vitro results suggest that corydaline should be evaluated for potential pharmacokinetic drug interactions in vivo due to potent inhibition of CYP2C19 and CYP2C9. Full article
Open AccessArticle Quantitative Structure Inter-Activity Relationship (QSInAR). Cytotoxicity Study of Some Hemisynthetic and Isolated Natural Steroids and Precursors on Human Fibrosarcoma Cells HT1080
Molecules 2011, 16(8), 6603-6620; doi:10.3390/molecules16086603
Received: 30 June 2011 / Revised: 28 July 2011 / Accepted: 29 July 2011 / Published: 5 August 2011
Cited by 7 | PDF Full-text (493 KB)
Abstract
Combined experimental and quantitative structure inter-activity relationship (QSIAR) computation methods were advanced in order to establish the structural and mechanistic influences that steroids and triterpenes, either as newly synthesized or naturally isolated products, have on human HT1080 mammalian cancer cells. The main [...] Read more.
Combined experimental and quantitative structure inter-activity relationship (QSIAR) computation methods were advanced in order to establish the structural and mechanistic influences that steroids and triterpenes, either as newly synthesized or naturally isolated products, have on human HT1080 mammalian cancer cells. The main Hansch structural indicators such as hydrophobicity (LogP), polarizability (POL) and total energy (Etot) were considered and both the structure-projected as well as globally computed correlations were reported; while the inter-activity correlation of the global activity with those projected on structural information was revealed as equal to the direct structural-activity one for the trial sets of compounds, the prediction for the testing set of molecules reported even superior performances respecting those characteristic for the calibration set, validating therefore the present QSInAR models; accordingly, it follows that the LogP carries the most part of the cytotoxic signal, while POL has little influence on inhibiting tumor growth—A complementary behavior with their earlier known influence on genotoxic carcinogenesis. Regarding the newly hemisynthetic compounds it was found that stigmasta-4,22-dien-3-one is not adapted for cell membrane diffusion; it is recommended that aminocinnamyl chlorohydrate be further modified in order to acquire better steric influence, while aminocinnamyl-2,3,4,6-O-tétraacétyl-α-D-glucopyranoside was identified as being inhibited in the tumor cell by other molecular mechanisms–here not revealed–although it has a moderate-high anti-cancer structurally predicted activity. Full article
(This article belongs to the Special Issue Steroids)
Figures

Open AccessArticle Metabolism Study of Notoginsenoside R1, Ginsenoside Rg1 and Ginsenoside Rb1 of Radix Panax Notoginseng in Zebrafish
Molecules 2011, 16(8), 6621-6633; doi:10.3390/molecules16086621
Received: 4 July 2011 / Revised: 22 July 2011 / Accepted: 29 July 2011 / Published: 5 August 2011
Cited by 10 | PDF Full-text (1017 KB)
Abstract
Zebrafish, a common model organism for studies of vertebrate development and gene function, has been used in pharmaceutical research as a new and powerful tool in recent years. In the present study, we applied zebrafish for the first time in a metabolic [...] Read more.
Zebrafish, a common model organism for studies of vertebrate development and gene function, has been used in pharmaceutical research as a new and powerful tool in recent years. In the present study, we applied zebrafish for the first time in a metabolic study of notoginsenoside (R1), ginsenoside (Rg1) and ginsenoside (Rb1), which are saponins isolated from Panax notoginseng. Metabolites of these three saponin compounds in zebrafish after exposure for 24 h were identified by high performance liquid chromatography - electrospray mass spectrometry (HPLC-ESI-MS) with a Zorbax C-18 column for separation using a binary gradient elution of 0.05% formic acid acetonitrile - 0.05% formic acid water. The quasi-molecular ions of compounds were detected in negative mode. Step-wise deglycosylation metabolites and hydroxylation metabolites of the three saponins were found, which were coincide with regular methods for metabolic analysis. Our study demonstrated that the zebrafish model can successfully imitate the current metabolic model with advantages of lower cost, far less amount of compound needed, easy set up and high performance. Our data suggests that the zebrafish metabolic model has the potential for developing a novel method for quickly predicting the metabolism of Chinese herb components, including those of trace compounds. Full article
Open AccessArticle Enzymatic Synthesis of Fatty Hydroxamic Acid Derivatives Based on Palm Kernel Oil
Molecules 2011, 16(8), 6634-6644; doi:10.3390/molecules16086634
Received: 20 June 2011 / Revised: 19 July 2011 / Accepted: 19 July 2011 / Published: 5 August 2011
Cited by 7 | PDF Full-text (438 KB)
Abstract
Fatty hydroxamic acid derivatives were synthesized using Lipozyme TL IM catalyst at biphasic medium as the palm kernel oil was dissolved in hexane and hydroxylamine derivatives were dissolved in water: (1) N-methyl fatty hydroxamic acids (MFHAs); (2) N-isopropyl fatty hydroxamic [...] Read more.
Fatty hydroxamic acid derivatives were synthesized using Lipozyme TL IM catalyst at biphasic medium as the palm kernel oil was dissolved in hexane and hydroxylamine derivatives were dissolved in water: (1) N-methyl fatty hydroxamic acids (MFHAs); (2) N-isopropyl fatty hydroxamic acids (IPFHAs) and (3) N-benzyl fatty hydroxamic acids (BFHAs) were synthesized by reaction of palm kernel oil and N-methyl hydroxylamine (N-MHA), N-isopropyl hydroxylamine (N-IPHA) and N-benzyl hydroxylamine (N-BHA), respectively. Finally, after separation the products were characterized by color testing, elemental analysis, FT-IR and 1H-NMR spectroscopy. For achieving the highest conversion percentage of product the optimum molar ratio of reactants was obtained by changing the ratio of reactants while other reaction parameters were kept constant. For synthesis of MFHAs the optimum mol ratio of N-MHA/palm kernel oil = 6/1 and the highest conversion was 77.8%, for synthesis of IPFHAs the optimum mol ratio of N-IPHA/palm kernel oil = 7/1 and the highest conversion was 65.4% and for synthesis of BFHAs the optimum mol ratio of N-BHA/palm kernel oil = 7/1 and the highest conversion was 61.7%. Full article
(This article belongs to the Special Issue Enzyme-Catalyzed Reactions)
Open AccessArticle Docking Studies and α-Substitution Effects on the Anti-Inflammatory Activity of β-Hydroxy-β-arylpropanoic Acids
Molecules 2011, 16(8), 6645-6655; doi:10.3390/molecules16086645
Received: 2 June 2011 / Revised: 26 July 2011 / Accepted: 3 August 2011 / Published: 5 August 2011
Cited by 1 | PDF Full-text (531 KB)
Abstract
Six β-hydroxy-β-aryl propanoic acids were synthesised using a modification of Reformatsky reaction which has already been reported. These acids belong to the aryl propanoic acid class of compounds, structurally similar to the NSAIDs, such as ibuprofen, and an anti-inflammatory activity is thus [...] Read more.
Six β-hydroxy-β-aryl propanoic acids were synthesised using a modification of Reformatsky reaction which has already been reported. These acids belong to the aryl propanoic acid class of compounds, structurally similar to the NSAIDs, such as ibuprofen, and an anti-inflammatory activity is thus expected. The aim of this work was to determine anti-inflammatory activity, examine gastric tolerability, and to carry out molecular docking experiments to identify potential COX-2 inhibitors among the β-hydroxy-β-aryl propanoic acids, and to elucidate the effect α-methyl substitution on the anti-inflammatory activity. Anti-inflammatory activity and gastric tolerability were determined on rats using carragenan induced paw oedema method, and docking studies were carried out using Autodock v4.0.1. The range of ED50 values is between 127 µmol/kg and 15 µmol/kg, while the result for ibuprofen is 51.7 µmol/kg. Only slight hyperaemia or few petechiae were spotted on rat’s stomach. The results indicate that all compounds possess significant anti-inflammatory activity after oral administration, and that 2-methyl-3-hydroxy-3,3-diphenyl-propanoic acid has greatest activity, surpassing that of ibuprofen, a standard NSAID. Another compound, 3-hydroxy-3,3-diphenylpropanoic acid, shows activity matching that of ibuprofen, and is non-chiral and is proven to be non-toxic. The most of investigated compounds have interactions with P3 anchor site like COX-2 selective inhibitors. No tested substances or ibuprofen produced any significant gastric lesions. Full article
Open AccessArticle In Vitro Synergy of Biochanin A and Ciprofloxacin against Clinical Isolates of Staphylococcus aureus
Molecules 2011, 16(8), 6656-6666; doi:10.3390/molecules16086656
Received: 11 July 2011 / Revised: 30 July 2011 / Accepted: 2 August 2011 / Published: 5 August 2011
Cited by 3 | PDF Full-text (364 KB)
Abstract
Many clinical isolates of Staphylococcus aureus (S. aureus) are resistant to numerous antimicrobials, including the fluoroquinolones (FQs). Flavonoids such as biochanin A (BCA) are compounds that are naturally present in fruits, vegetables, and plant-derived beverages. The goal of this investigation [...] Read more.
Many clinical isolates of Staphylococcus aureus (S. aureus) are resistant to numerous antimicrobials, including the fluoroquinolones (FQs). Flavonoids such as biochanin A (BCA) are compounds that are naturally present in fruits, vegetables, and plant-derived beverages. The goal of this investigation was to study the possible synergy between the antimicrobial agents BCA and ciprofloxacin (CPFX) when used in combination; CPFX was chosen as a representative FQ compound. We used S. aureus strain ATCC 25923 and 11 fluoroquinolone (FQ)-resistant methicillin-resistant S. aureus (MRSA) strains. Results from the drug susceptibility testing and checkerboard assays show that the minimum inhibitory concentration (MIC) of BCA ranged from 64 µg/mL to 512 µg/mL. When BCA was combined with CPFX, the fractional inhibitory concentration index (FICI) data showed that there was synergy in all 12 of the S. aureus strains tested. No antagonistic activity was observed in any of the strains tested. The results of time-kill tests and agar diffusion tests confirm that there was synergy between BCA and CPFX against S. aureus strains. These results suggest that BCA can be combined with FQs to produce a powerful antimicrobial agent. Full article
Open AccessArticle Green Synthesis and Antibacterial Effect of Silver Nanoparticles Using Vitex Negundo L.
Molecules 2011, 16(8), 6667-6676; doi:10.3390/molecules16086667
Received: 30 June 2011 / Revised: 19 July 2011 / Accepted: 19 July 2011 / Published: 8 August 2011
Cited by 64 | PDF Full-text (345 KB)
Abstract
Different biological methods are gaining recognition for the production of silver nanoparticles (Ag-NPs) due to their multiple applications. One of the most important applications of Ag-NPs is their use as an anti-bacterial agent. The use of plants in the synthesis of nanoparticles [...] Read more.
Different biological methods are gaining recognition for the production of silver nanoparticles (Ag-NPs) due to their multiple applications. One of the most important applications of Ag-NPs is their use as an anti-bacterial agent. The use of plants in the synthesis of nanoparticles emerges as a cost effective and eco-friendly approach. In this study the biosynthesis of silver nanoparticles using Vitex negundo L. extract and its antimicrobial properties has been reported. The resulting silver particles are characterized using transmission electron microscopy (TEM), X-ray diffraction (XRD) and UV–Visible (UV-Vis) spectroscopic techniques. The TEM study showed the formation of silver nanoparticles in the 10–30 nm range and average 18.2 nm in size. The XRD study showed that the particles are crystalline in nature, with a face centered cubic (fcc) structure. The silver nanoparticles showed the antimicrobial activity against Gram positive and Gram negative bacteria. Vitex negundo L. was found to display strong potential for the synthesis of silver nanoparticles as antimicrobial agents by rapid reduction of silver ions (Ag+ to Ag0). Full article
Open AccessArticle Fast Method for Synthesis of Alkyl and Aryl-N-Methylnitrones
Molecules 2011, 16(8), 6677-6683; doi:10.3390/molecules16086677
Received: 20 June 2011 / Revised: 18 July 2011 / Accepted: 19 July 2011 / Published: 8 August 2011
Cited by 3 | PDF Full-text (426 KB)
Abstract
A simple, fast, efficient and eco-friendly procedure was developed for the synthesis of alkyl and aryl-N-methylnitrones. The corresponding nitrones of aromatic aldehydes, aliphatic aldehydes and alicyclic carbonyl compounds were prepared from N-methylhydroxylamine hydrochloride and Na2CO3-Na [...] Read more.
A simple, fast, efficient and eco-friendly procedure was developed for the synthesis of alkyl and aryl-N-methylnitrones. The corresponding nitrones of aromatic aldehydes, aliphatic aldehydes and alicyclic carbonyl compounds were prepared from N-methylhydroxylamine hydrochloride and Na2CO3-Na2SO4 by simply grinding at room temperature without using solvent. Full article
Open AccessArticle 3D-QSAR Study of Combretastatin A-4 Analogs Based on Molecular Docking
Molecules 2011, 16(8), 6684-6700; doi:10.3390/molecules16086684
Received: 14 June 2011 / Revised: 26 July 2011 / Accepted: 28 July 2011 / Published: 8 August 2011
Cited by 6 | PDF Full-text (923 KB)
Abstract
Combretastatin A-4 (CA-4), its analogues and their excellent antitumoral and antivascular activities, have attracted considerable interest of medicinal chemists. In this article, a docking simulation was used to identify molecules having the same binding mode as the lead compound, and 3D-QSAR models [...] Read more.
Combretastatin A-4 (CA-4), its analogues and their excellent antitumoral and antivascular activities, have attracted considerable interest of medicinal chemists. In this article, a docking simulation was used to identify molecules having the same binding mode as the lead compound, and 3D-QSAR models had been built by using CoMFA based on docking. As a result, these studies indicated that the QSAR models were statistically significant with high predictabilities (CoMFA model, q2 = 0.786, r2 = 0.988). Our models may offer help to better comprehend the structure-activity relationships for this class of compounds and also facilitate the design of novel inhibitors with good chemical diversity. Full article
Open AccessArticle Group 11 Metal Compounds with Tripodal Bis(imidazole) Thioether Ligands. Applications as Catalysts in the Oxidation of Alkenes and as Antimicrobial Agents
Molecules 2011, 16(8), 6701-6720; doi:10.3390/molecules16086701
Received: 8 July 2011 / Revised: 22 July 2011 / Accepted: 2 August 2011 / Published: 8 August 2011
Cited by 9 | PDF Full-text (636 KB)
Abstract
New group 11 metal complexes have been prepared using the previously described tripodal bis(imidazole) thioether ligand (N-methyl-4,5-diphenyl-2-imidazolyl)2C(OMe)C(CH3)2S(tert-Bu) ({BITOMe,StBu}, 2). The pincer ligand offers a N2S donor atom [...] Read more.
New group 11 metal complexes have been prepared using the previously described tripodal bis(imidazole) thioether ligand (N-methyl-4,5-diphenyl-2-imidazolyl)2C(OMe)C(CH3)2S(tert-Bu) ({BITOMe,StBu}, 2). The pincer ligand offers a N2S donor atom set that can be used to coordinate the group 11 metals in different oxidation states [AuI, AuIII, AgI, CuI and CuII]. Thus the new compounds [Au{BITOMe,StBu}Cl][AuCl4]2 (3), [Au{BITOMe,StBu}Cl] (4), [Ag{BITOMe,StBu}X] (X = OSO2CF3- 5, PF6- 6) and [Cu{BITOMe,StBu}Cl2] (7) have been synthesized from reaction of 2 with the appropriate metal precursors, and characterized in solution. While attempting characterization in the solid state of 3, single crystals of the neutral dinuclear mixed AuIII-AuI species [Au2{BITOMe,S}Cl3] (8) were obtained and its crystal structure was determined by X-ray diffraction studies. The structure shows a AuIII center coordinated to the pincer ligand through one N and the S atom. The soft AuI center coordinates to the ligand through the same S atom that has lost the tert-butyl group, thus becoming a thiolate ligand. The short distance between the AuI-AuIII atoms (3.383 Å) may indicate a weak metal-metal interaction. Complexes 2-7 and the previously described CuI compound [Cu{BITOMe,StBu}]PF6 (9) have been evaluated in the oxidation of biphenyl ethylene with tert-butyl hydrogen peroxide (TBHP) as the oxidant. Results have shown that the AuI and AgI complexes 4 and 6 (at 10 mol % loading) are the more active catalysts in this oxidative cleavage. The antimicrobial activity of compounds 2-5, 7 and 9 against Gram-positive and Gram-negative bacteria and yeast has also been evaluated. The new gold and silver compounds display moderate to high antibacterial activity, while the copper derivatives are mostly inactive. The gold and silver complexes were also potent against fungi. Their cytotoxic properties have been analyzed in vitro utilizing HeLa human cervical carcinoma cells. The compounds displayed a very low cytotoxicity on this cell line (5 to 10 times lower than cisplatin) and on normal primary cells derived from C57B6 mouse muscle explants, which may make them promising candidates as potential antimicrobial agents and safer catalysts due to low toxicity in human and other mammalian tissues. Full article
(This article belongs to the Special Issue Pincer Compounds)
Figures

Open AccessArticle Proanthocyanidins from Grape Seeds Modulate the NF-κB Signal Transduction Pathways in Rats with TNBS-Induced Ulcerative Colitis
Molecules 2011, 16(8), 6721-6731; doi:10.3390/molecules16086721
Received: 5 July 2011 / Revised: 29 July 2011 / Accepted: 3 August 2011 / Published: 8 August 2011
Cited by 6 | PDF Full-text (502 KB)
Abstract
To elucidate the molecular mechanisms involved in the therapeutic effects of proanthocyanidins from grape seeds (GSPE), we explore whether GSPE regulates the inflammatory response of TNBS-induced colitis in rats at the levels of NF-κB signal transduction pathway. Rats were intragastrically [...] Read more.
To elucidate the molecular mechanisms involved in the therapeutic effects of proanthocyanidins from grape seeds (GSPE), we explore whether GSPE regulates the inflammatory response of TNBS-induced colitis in rats at the levels of NF-κB signal transduction pathway. Rats were intragastrically administered of different doses of GSPE (100, 200 and 400 mg·kg−1) per day for seven days after ulcerative colitis (UC) was induced by intracolonic injection of 2,4,6-trinitrobenzenesulfonic acid (TNBS) dissolved in 50% ethanol. Sulfasalazine (SASP) at 400 mg/kg was used as a positive control drug. The expression of nuclear factor-kappa B (NF-κB), phospho-I kappaB-alpha (pIκBα), inhibitor kappa B kinase (IκK) in the colon tissues were all measured by enzyme-linked immunosorbent assay (ELISA) methods. Treatment with GSPE reduced the expression of NF-κB, pIκBα and IκK in the colon. The results of this study show that GSPE exerts beneficial effects in inflammatory bowel disease by inhibition of NF-κB signal transduction pathways. Full article
Open AccessArticle Computational and Spectral Investigation of 5,12-Dihydro-5,12-ethanonaphthacene-13-carbaldehyde
Molecules 2011, 16(8), 6741-6746; doi:10.3390/molecules16086741
Received: 15 May 2011 / Revised: 2 August 2011 / Accepted: 2 August 2011 / Published: 9 August 2011
Cited by 1 | PDF Full-text (379 KB)
Abstract
A conformational search of 5,12-dihydro-5,12-ethanonaphthacene-13-carbaldehyde predicted the presence of twelve conformations. The geometry of the twelve conformations established at the B3LYP/6-31G* level showed only six unique ones. Vibrational frequencies were calculated at the B3LYP/6-31G* level. The calculated vibrational frequencies enabled us to [...] Read more.
A conformational search of 5,12-dihydro-5,12-ethanonaphthacene-13-carbaldehyde predicted the presence of twelve conformations. The geometry of the twelve conformations established at the B3LYP/6-31G* level showed only six unique ones. Vibrational frequencies were calculated at the B3LYP/6-31G* level. The calculated vibrational frequencies enabled us to interpret the appearance of two bands corresponding to the C=O stretching mode of 5,12-dihydro-5,12-ethanonaphthacene-13-carbaldehyde. The first band corresponded to the 5,12-dihydro-5,12-ethanonaphthacene-13-carbaldehyde structure where the aldehyde group O atom was above the benzene or naphthalene ring. The other band was due to the O atom of the aldehyde group pointing out of the benzene or naphthalene ring. Full article
(This article belongs to the Special Issue Protecting Group in Organic Synthesis)
Open AccessArticle Chemo-Enzymatic Synthesis of a Multi-Useful Chiral Building Block Molecule for the Synthesis of Medicinal Compounds
Molecules 2011, 16(8), 6747-6757; doi:10.3390/molecules16086747
Received: 4 July 2011 / Revised: 2 August 2011 / Accepted: 4 August 2011 / Published: 9 August 2011
Cited by 5 | PDF Full-text (255 KB)
Abstract Optical resolution of 2-methyl-2-nitrobut-3-en-1-ol has been accomplished using a “low-temperature lipase-catalyzed transesterification” carried out at −40 °C. Full article
(This article belongs to the Special Issue Enzyme-Catalyzed Reactions)
Open AccessArticle Parthenolide Induces Apoptosis and Cell Cycle Arrest of Human 5637 Bladder Cancer Cells In Vitro
Molecules 2011, 16(8), 6758-6768; doi:10.3390/molecules16086758
Received: 20 June 2011 / Revised: 30 July 2011 / Accepted: 2 August 2011 / Published: 9 August 2011
Cited by 14 | PDF Full-text (2674 KB)
Abstract
Parthenolide, the principal component of sesquiterpene lactones present in medical plants such as feverfew (Tanacetum parthenium), has been reported to have anti-tumor activity. In this study, we evaluated the therapeutic potential of parthenolide against bladder cancer and its mechanism of [...] Read more.
Parthenolide, the principal component of sesquiterpene lactones present in medical plants such as feverfew (Tanacetum parthenium), has been reported to have anti-tumor activity. In this study, we evaluated the therapeutic potential of parthenolide against bladder cancer and its mechanism of action. Treatment of bladder cancer cells with parthenolide resulted in a significant decrease in cell viability. Parthenolide induced apoptosis through the modulation of Bcl-2 family proteins and poly (ADP-ribose) polymerase degradation. Treatment with parthenolide led to G1 phase cell cycle arrest in 5637 cells by modulation of cyclin D1 and phosphorylated cyclin-dependent kinase 2. Parthenolide also inhibited the invasive ability of bladder cancer cells. These findings suggest that parthenolide could be a novel therapeutic agent for treatment of bladder cancer. Full article
Open AccessArticle Chemo-Enzymatic Synthesis of Ester-Linked Docetaxel-Monosaccharide Conjugates as Water-Soluble Prodrugs
Molecules 2011, 16(8), 6769-6777; doi:10.3390/molecules16086769
Received: 24 June 2011 / Revised: 28 July 2011 / Accepted: 3 August 2011 / Published: 9 August 2011
Cited by 4 | PDF Full-text (115 KB)
Abstract
Three new docetaxel prodrugs, i.e., 7-propionyldocetaxel 3''-O-b-D-glycopyranosides, which contain ester-linked monosaccharides, were synthesized by a chemo-enzymatic procedure involving enzymatic transglycosylations with lactase, b-galactosidase, or b-xylosidase. The water-solubility of 7-propionyldocetaxel 3''-O-b-D-glucopyranoside was 52-fold higher than that of docetaxel. [...] Read more.
Three new docetaxel prodrugs, i.e., 7-propionyldocetaxel 3''-O-b-D-glycopyranosides, which contain ester-linked monosaccharides, were synthesized by a chemo-enzymatic procedure involving enzymatic transglycosylations with lactase, b-galactosidase, or b-xylosidase. The water-solubility of 7-propionyldocetaxel 3''-O-b-D-glucopyranoside was 52-fold higher than that of docetaxel. 7-Propionyldocetaxel 3''-O-b-D-glucopyranoside and 7-propionyldocetaxel 3''-O-b-D-xylopyranoside were effectively hydrolyzed by the relevant enzyme(s) of human cancer cells to release docetaxel, whereas 7-propionyldocetaxel 3''-O-b-D-galactopyranoside was relatively resistant under similar conditions. 7-Propionyldocetaxel 3''-O-b-D-glucopyranoside and 7-propionyldocetaxel 3''-O-b-D-xylopyranoside showed in vitro cytotoxic activity against human cancer cells, whereas 7-propionyldocetaxel 3''-O-b-D-galactopyranoside exerted low cytotoxicity. Full article
(This article belongs to the Special Issue Enzyme-Catalyzed Reactions)
Open AccessArticle A Biomimetic Chitosan Derivates: Preparation, Characterization and Transdermal Enhancement Studies of N-Arginine Chitosan
Molecules 2011, 16(8), 6778-6790; doi:10.3390/molecules16086778
Received: 11 July 2011 / Revised: 25 July 2011 / Accepted: 1 August 2011 / Published: 9 August 2011
Cited by 18 | PDF Full-text (573 KB)
Abstract
A novel arginine-rich chitosan (CS) derivates mimicked cell penetration peptides; N-Arginine chitosan (N-Arg-CS) was prepared by two reaction methods involving activated L-arginine and the amine group on the chitosan. FTIR spectra showed that arginine was chemically coupled with CS. [...] Read more.
A novel arginine-rich chitosan (CS) derivates mimicked cell penetration peptides; N-Arginine chitosan (N-Arg-CS) was prepared by two reaction methods involving activated L-arginine and the amine group on the chitosan. FTIR spectra showed that arginine was chemically coupled with CS. Elemental analysis estimated that the degrees of substitution (DS) of arginine in CS were 6%, 31.3% and 61.5%, respectively. The drug adefovir was chosen as model and its permeation flux across excised mice skin was investigated using a Franz diffusion cell. The results showed that the most effective enhancer was 2% (w/v) concentration of 10 kDa N-Arg-CS with 6% DS. At neutral pH, the cumulative amount of adefovir permeated after 12 hours was 2.63 ± 0.19 mg cm−2 which was 5.83-fold more than adefovir aqueous solution. Meanwhile N-Arg-CS was 1.83, 2.22, and 2.45 times more effective than Azone, eucalyptus and peppermint, respectively. The obtained results suggest that N-Arg-CS could be a promising transdermal enhancer. Full article
(This article belongs to the Section Medicinal Chemistry)
Open AccessArticle HPLC and GC-MS Determination of Bioactive Compounds in Microwave Obtained Extracts of Three Varieties of Labisia pumila Benth.
Molecules 2011, 16(8), 6791-6805; doi:10.3390/molecules16086791
Received: 2 May 2011 / Revised: 28 July 2011 / Accepted: 1 August 2011 / Published: 9 August 2011
Cited by 30 | PDF Full-text (151 KB)
Abstract
Microwave extraction of phytochemicals from medicinal plant materials has generated tremendous research interest and shown great potential. This research highlights the importance of microwave extraction in the analysis of flavonoids, isoflavonoid and phenolics and the antioxidant properties of extracts from three varieties [...] Read more.
Microwave extraction of phytochemicals from medicinal plant materials has generated tremendous research interest and shown great potential. This research highlights the importance of microwave extraction in the analysis of flavonoids, isoflavonoid and phenolics and the antioxidant properties of extracts from three varieties of the Malaysian medicinal herb, Labisia pumila Benth. High and fast extraction performance ability, equal or higher extraction efficiencies than other methods, and the need for small samples and reagent volumes are some of the attractive features of this new promising microwave assisted extraction (MAE) technique. The aims of the present research were to determine the foliar phenolics and flavonoids contents of extracts of three varieties of L. pumila obtained by a microwave extraction method while flavonoid, isoflavonoid and phenolic compounds were analyzed using RP-HPLC. Furthermore, the antioxidant activities were measured by the DPPH and FRAP methods and finally, the chemical composition of the crude methanolic extracts of the leaves of all three varieties were analyzed by GS-MS. Full article
(This article belongs to the Section Natural Products)
Open AccessArticle Synthesis and Biological Activity of New 1,3-Dioxolanes as Potential Antibacterial and Antifungal Compounds
Molecules 2011, 16(8), 6806-6815; doi:10.3390/molecules16086806
Received: 20 July 2011 / Revised: 2 August 2011 / Accepted: 3 August 2011 / Published: 10 August 2011
Cited by 9 | PDF Full-text (135 KB)
Abstract
A series of new enantiomerically pure and racemic 1,3-dioxolanes 1-8 was synthesized in good yields and short reaction times by the reaction of salicylaldehyde with commercially available diols using a catalytic amount of Mont K10. Elemental analysis and spectroscopic characterization [...] Read more.
A series of new enantiomerically pure and racemic 1,3-dioxolanes 1-8 was synthesized in good yields and short reaction times by the reaction of salicylaldehyde with commercially available diols using a catalytic amount of Mont K10. Elemental analysis and spectroscopic characterization established the structure of all the newly synthesized compounds. These compounds were tested for their possible antibacterial and antifungal activity. Biological screening showed that all the tested compounds, except 1, show excellent antifungal activity against C. albicans, while most of the compounds have also shown significant antibacterial activity against S. aureus, S. epidermidis, E. faecalis and P. aeruginosa. Full article
Figures

Open AccessArticle Seasonal Effects on Bioactive Compounds and Antioxidant Capacity of Six Economically Important Brassica Vegetables
Molecules 2011, 16(8), 6816-6832; doi:10.3390/molecules16086816
Received: 14 June 2011 / Revised: 29 July 2011 / Accepted: 8 August 2011 / Published: 10 August 2011
Cited by 26 | PDF Full-text (222 KB)
Abstract
Research on natural and bioactive compounds is increasingly focused on their effects on human health, but there are unexpectedly few studies evaluating the relationship between climate and natural antioxidants. The aim of this study was analyze the biological role of six different [...] Read more.
Research on natural and bioactive compounds is increasingly focused on their effects on human health, but there are unexpectedly few studies evaluating the relationship between climate and natural antioxidants. The aim of this study was analyze the biological role of six different Brassica vegetables (Brassica oleracea L. and Brassica rapa L.) as a natural source of antioxidant compounds. The antioxidant activity may be assigned to high levels of L-ascorbic acid, total phenolics and total flavonoids of each sample. The climate seasons affected directly the concentration of bioactive components and the antioxidant activity. Broccoli inflorescences and Portuguese kale showed high antioxidant activity in Spring-Summer whilst turnip leaves did so in Summer-Winter. The Brassica vegetables can provide considerable amounts of bioactive compounds and thus may constitute an important natural source of dietary antioxidants. Full article
Open AccessArticle The Use of Umbelliferone in the Synthesis of New Heterocyclic Compounds
Molecules 2011, 16(8), 6833-6843; doi:10.3390/molecules16086833
Received: 11 July 2011 / Revised: 22 July 2011 / Accepted: 1 August 2011 / Published: 10 August 2011
Cited by 30 | PDF Full-text (522 KB)
Abstract New coumarin derivatives, namely 7-[(5-amino-1,3,4-thiadiazol-2-yl)methoxy]-2H-chromen-2-one (4), 5-[(2-oxo-2H-chromen-7-yloxy)methyl]-1,3,4-thiadiazol-2(3H)-one (5), 2-[2-(2-oxo-2H-chromen-7-yloxy)acetyl]-N-phenylhydrazinecarbothioamide (7), 7-[(5-(phenylamino)-1,3,4-thiadiazol-2-yl)methoxy]-2H-chromen-2-one (8) and 7-[(5-mercapto-4-phenyl-4H-1,2,4-triazol-3-yl)methoxy]-2H-chromen-2-one (9) were prepared starting from the natural compound umbelliferone (1). The newly synthesized compounds were characterized by elemental analysis and spectral studies (IR, 1H-NMR and 13C-NMR). Full article
(This article belongs to the Section Organic Synthesis)
Open AccessArticle Li+ Selective Podand-Type Fluoroionophore Based on a Diphenyl Sulfoxide Derivative Bearing Two Pyrene Groups
Molecules 2011, 16(8), 6844-6857; doi:10.3390/molecules16086844
Received: 11 July 2011 / Revised: 28 July 2011 / Accepted: 8 August 2011 / Published: 10 August 2011
Cited by 3 | PDF Full-text (402 KB)
Abstract
New podand-type fluoroionophores having two pyrene moieties: 2,2´-bis(1-pyrenylacetyloxy)diphenyl sulfide (3), 2,2´-bis(1-pyrenylacetyloxy)diphenyl sulfoxide (4), and 2,2´-bis(1-pyrenylacetyloxy)diphenyl sulfone (5), have been synthesized by connecting two 1-pyrenecarbonylmethyl groups with the two hydroxy groups of 2,2´-dihydroxydiphenyl sulfide, sulfoxide, and sulfone, [...] Read more.
New podand-type fluoroionophores having two pyrene moieties: 2,2´-bis(1-pyrenylacetyloxy)diphenyl sulfide (3), 2,2´-bis(1-pyrenylacetyloxy)diphenyl sulfoxide (4), and 2,2´-bis(1-pyrenylacetyloxy)diphenyl sulfone (5), have been synthesized by connecting two 1-pyrenecarbonylmethyl groups with the two hydroxy groups of 2,2´-dihydroxydiphenyl sulfide, sulfoxide, and sulfone, respectively. Their complexation behavior toward alkali metal ions was examined by fluorescence spectroscopy. Among these fluoroionophores, compound 4, having a sulfinyl group, showed high selectivity toward Li+. Full article
Figures

Open AccessArticle Microwave Assisted Organic Synthesis (MAOS) of Small Molecules as Potential HIV-1 Integrase Inhibitors
Molecules 2011, 16(8), 6858-6870; doi:10.3390/molecules16086858
Received: 18 July 2011 / Revised: 4 August 2011 / Accepted: 8 August 2011 / Published: 11 August 2011
Cited by 4 | PDF Full-text (511 KB)
Abstract
Integrase (IN) represents a clinically validated target for the development of antivirals against human immunodeficiency virus (HIV). In recent years our research group has been engaged in the stucture-function study of this enzyme and in the development of some three-dimensional pharmacophore models [...] Read more.
Integrase (IN) represents a clinically validated target for the development of antivirals against human immunodeficiency virus (HIV). In recent years our research group has been engaged in the stucture-function study of this enzyme and in the development of some three-dimensional pharmacophore models which have led to the identification of a large series of potent HIV-1 integrase strand-transfer inhibitors (INSTIs) bearing an indole core. To gain a better understanding of the structure-activity relationships (SARs), herein we report the design and microwave-assisted synthesis of a novel series of 1-H-benzylindole derivatives. Full article
(This article belongs to the Special Issue Microwave Assisted Synthesis)
Open AccessCommunication High Functionalization of 5-Nitro-1H-imidazole Derivatives: The TDAE Approach
Molecules 2011, 16(8), 6883-6893; doi:10.3390/molecules16086883
Received: 20 July 2011 / Revised: 5 August 2011 / Accepted: 8 August 2011 / Published: 12 August 2011
Cited by 7 | PDF Full-text (472 KB)
Abstract We report herein the synthesis of substituted 2-[4-(1,2-dimethyl-5-nitro-1H-imidazol-4-yl)phenyl]-1-arylethanols, ethyl 3-[4-(1,2-dimethyl-5-nitro-1H-imidazol-4-yl)-phenyl]-2-hydroxypropanoate and 2-[4-(1,2-dimethyl-5-nitro-1H-imidazol-4-yl)benzyl]-2-hydroxy-acenaphthylen-1(2H)-one from the reactions of 4-[4-(chloromethyl)phenyl]-1,2-dimethyl-5-nitro-1H-imidazole with various aromatic carbonyl and a-carbonyl ester derivatives using tetrakis(dimethylamino)ethylene (TDAE) methodology. Full article
Figures

Open AccessArticle Synthesis of Quinoxaline 1,4-di-N-Oxide Analogues and Crystal Structure of 2-Carbomethoxy-3-hydroxyquinoxaline-di-N-oxide
Molecules 2011, 16(8), 6894-6901; doi:10.3390/molecules16086894
Received: 28 June 2011 / Revised: 3 August 2011 / Accepted: 8 August 2011 / Published: 12 August 2011
Cited by 3 | PDF Full-text (423 KB)
Abstract
A series of quinoxaline 1,4-di-N-oxide analogues were prepared from benzofurazan N-oxide derivatives and β-diketone ester compounds by the improved Beirut reaction. The structures of the target products were characterized by NMR, MS, IR and elemental analysis measurements, and that [...] Read more.
A series of quinoxaline 1,4-di-N-oxide analogues were prepared from benzofurazan N-oxide derivatives and β-diketone ester compounds by the improved Beirut reaction. The structures of the target products were characterized by NMR, MS, IR and elemental analysis measurements, and that of 2-carbomethoxy-3-hydroxyquinoxaline- di-N-oxide was further confirmed by single-crystal X-ray diffraction. Its crystal structure belongs to the monoclinic system, space group C2/c with a = 14.4320 (12) Å, b = 10.7514 (9) Å, c = 13.2728 (11) Å, V = 1958.5 (3) Å 3, Z = 8. The X-ray crystallographic analysis reveals that quinoxaline 1,4-di-N-oxide displays acyloin-endiol tautomerism. Full article
Figures

Open AccessArticle Analgesic and Anti-Inflammatory Activities of Salicylaldehyde 2-Chlorobenzoyl Hydrazone (H2LASSBio-466), Salicylaldehyde 4-Chlorobenzoyl Hydrazone (H2LASSBio-1064) and Their Zinc(II) Complexes
Molecules 2011, 16(8), 6902-6915; doi:10.3390/molecules16086902
Received: 27 June 2011 / Revised: 2 August 2011 / Accepted: 11 August 2011 / Published: 15 August 2011
Cited by 19 | PDF Full-text (396 KB)
Abstract
Salicylaldehyde 2-chlorobenzoyl hydrazone (H2LASSBio-466), salicylaldehyde 4-chlorobenzoyl hydrazone (H2LASSBio-1064) and their complexes [Zn(LASSBio-466)H2O]2 (1) and [Zn(HLASSBio-1064)Cl]2 (2) were evaluated in animal models of peripheral and central nociception, and acute inflammation. All [...] Read more.
Salicylaldehyde 2-chlorobenzoyl hydrazone (H2LASSBio-466), salicylaldehyde 4-chlorobenzoyl hydrazone (H2LASSBio-1064) and their complexes [Zn(LASSBio-466)H2O]2 (1) and [Zn(HLASSBio-1064)Cl]2 (2) were evaluated in animal models of peripheral and central nociception, and acute inflammation. All studied compounds significantly inhibited acetic acid-induced writhing response. Upon coordination the anti-nociceptive activity was favored in the complex 1. H2LASSBio-466 inhibited only the first phase of the formalin test, while 1 was active in the second phase, like indomethacin, indicating its ability to inhibit nociception associated with the inflammatory response. Hence coordination to zinc(II) altered the pharmacological profile of H2LASSBio-466. H2LASSBio-1064 inhibited both phases but this effect was not improved by coordination. The studied compounds did not increase the latency of response in the hot plate model, indicating their lack of central anti-nociceptive activity. All compounds showed levels of inhibition of zymosan-induced peritonitis comparable or superior to indomethacin, indicating an expressive anti-inflammatory profile. Full article
(This article belongs to the Section Medicinal Chemistry)
Figures

Open AccessArticle Selective Covalent Conjugation of Phosphorothioate DNA Oligonucleotides with Streptavidin
Molecules 2011, 16(8), 6916-6926; doi:10.3390/molecules16086916
Received: 26 June 2011 / Revised: 8 August 2011 / Accepted: 11 August 2011 / Published: 15 August 2011
Cited by 3 | PDF Full-text (752 KB) | Supplementary Files
Abstract
Protein-DNA conjugates have found numerous applications in the field of diagnostics and nanobiotechnology, however, their intrinsic susceptibility to DNA degradation by nucleases represents a major obstacle for many applications. We here report the selective covalent conjugation of the protein streptavidin (STV) with [...] Read more.
Protein-DNA conjugates have found numerous applications in the field of diagnostics and nanobiotechnology, however, their intrinsic susceptibility to DNA degradation by nucleases represents a major obstacle for many applications. We here report the selective covalent conjugation of the protein streptavidin (STV) with phosphorothioate oligonucleotides (psDNA) containing a terminal alkylthiolgroup as the chemically addressable linking unit, using a heterobifunctional NHS-/maleimide crosslinker. The psDNA-STV conjugates were synthesized in about 10% isolated yields. We demonstrate that the terminal alkylthiol group selectively reacts with the maleimide while the backbone sulfur atoms are not engaged in chemical conjugation. The novel psDNA-STV conjugates retain their binding capabilities for both biotinylated macromolecules and the complementary nucleic acid. Moreover, the psDNA-STV conjugate retained its binding capacity for complementary oligomers even after a nuclease digestion step, which effectively degrades deoxyribonucleotide oligomers and thus the binding capability of regular DNA-STV conjugates. The psDNA-STV therefore hold particular promise for applications e.g. in proteome research and novel biosensing devices, where interfering endogenous nucleic acids need to be removed from analytes by nuclease digestion. Full article
Open AccessArticle A Comparative Study of Physical and Chemical Processes for Removal of Biomass in Biofilters
Molecules 2011, 16(8), 6927-6949; doi:10.3390/molecules16086927
Received: 11 July 2011 / Revised: 2 August 2011 / Accepted: 5 August 2011 / Published: 15 August 2011
Cited by 2 | PDF Full-text (687 KB)
Abstract
After 6 months of operation a long-term biofilter was stopped for two weeks and then it was started up again for a second experimental period of almost 1.3 years, with high toluene loads and submitted to several physical and chemical treatments in [...] Read more.
After 6 months of operation a long-term biofilter was stopped for two weeks and then it was started up again for a second experimental period of almost 1.3 years, with high toluene loads and submitted to several physical and chemical treatments in order to remove excess biomass that could affect the reactor’s performance due to clogging, whose main effect is a high pressure drop. Elimination capacity and removal efficiency were determined after each treatment. The methods applied were: filling with water and draining, backwashing, and air sparging. Different flows and temperatures (20, 30, 45 and 60 °C) were applied, either with distilled water or with different chemicals in aqueous solutions. Treatments with chemicals caused a decrease of the biofilter performance, requiring periods of 1 to 2 weeks to recover previous values. The results indicate that air sparging with pure distilled water as well as with solutions of NaOH (0.01% w/v) and NaOCl (0.01% w/v) were the treatments that removed more biomass, working either at 20, 30 or 45 °C and at relatively low flow rates (below 320 L h−1), but with a high biodegradation inhibition after the treatments. Dry biomass (g VS) content was determined at three different heights of the biofilter in order to carry out each experiment under the same conditions. The same amount of dry biomass when applying a treatment was established so it could be considered that the biofilm conditions were identical. Wet biomass was used as a control of the biofilter’s water content during treatments. Several batch assays were performed to support and quantify the observed inhibitory effects of the different chemicals and temperatures applied. Full article
Open AccessArticle Synthesis of Porphyrin-Dendrimers with a Pyrene in the Periphery and Their Cubic Nonlinear Optical Properties
Molecules 2011, 16(8), 6950-6968; doi:10.3390/molecules16086950
Received: 9 June 2011 / Revised: 3 August 2011 / Accepted: 5 August 2011 / Published: 15 August 2011
Cited by 7 | PDF Full-text (1114 KB)
Abstract
Dendrons of pyrene derivatives were attached to a porphyrin core. A marked effect in solution for the dendrimers was observed in the absorption spectra. All the compounds obtained were characterized by 1H-, 13C-NMR, FTIR, UV-vis, MALDI-TOF or FAB+ mass spectrometry [...] Read more.
Dendrons of pyrene derivatives were attached to a porphyrin core. A marked effect in solution for the dendrimers was observed in the absorption spectra. All the compounds obtained were characterized by 1H-, 13C-NMR, FTIR, UV-vis, MALDI-TOF or FAB+ mass spectrometry and elemental analysis. The cubic nonlinear optical behavior of some the synthesized compounds was tested via Z-Scan measurements in spin-coated film samples. Full article
(This article belongs to the Special Issue Tetrapyrroles, Porphyrins and Phthalocyanines)
Figures

Open AccessArticle Antimicrobial and Antioxidant Activities of New Metal Complexes Derived from 3-Aminocoumarin
Molecules 2011, 16(8), 6969-6984; doi:10.3390/molecules16086969
Received: 20 June 2011 / Revised: 14 July 2011 / Accepted: 15 July 2011 / Published: 15 August 2011
Cited by 30 | PDF Full-text (440 KB)
Abstract
3-Aminocoumarin (L) has been synthesized and used as a ligand for the formation of Cr(III), Ni(II), and Cu(II) complexes. The chemical structures were characterized using different spectroscopic methods. The elemental analyses revealed that the complexes where M=Ni(II) and Cu(II) have [...] Read more.
3-Aminocoumarin (L) has been synthesized and used as a ligand for the formation of Cr(III), Ni(II), and Cu(II) complexes. The chemical structures were characterized using different spectroscopic methods. The elemental analyses revealed that the complexes where M=Ni(II) and Cu(II) have the general formulae [ML2Cl2], while the Cr(III) complex has the formula [CrL2Cl2]Cl. The molar conductance data reveal that all the metal chelates, except the Cr(III) one, are non-electrolytes. From the magnetic and UV-Visible spectra, it is found that these complexes have octahedral structures. The stability for the prepared complexes was studied theoretically using Density Function Theory. The total energy for the complexes was calculated and it was shown that the copper complex is the most stable one. Complexes were tested against selected types of microbial organisms and showed significant activities. The free radical scavenging activity of metal complexes have been determined by measuring their interaction with the stable free radical DPPH and all the compounds have shown encouraging antioxidant activities. Full article
Open AccessArticle Synthesis of New Riminophenazines with Pyrimidine and Pyrazine Substitution at the 2-N Position
Molecules 2011, 16(8), 6985-6991; doi:10.3390/molecules16086985
Received: 11 July 2011 / Revised: 6 August 2011 / Accepted: 9 August 2011 / Published: 16 August 2011
Cited by 3 | PDF Full-text (477 KB)
Abstract New riminophenazines with pyrimidine and pyrazine substituents at the 2-position were successfully synthesized. The key step is the 2-N-arylation of riminophenazines with pyrimidine and pyrazine. The optimized reaction conditions involve the use of a Pd2(dba)3/DPPF/Cs2CO3/toluene combination. Full article
Open AccessArticle Antiviral Properties of Lactoferrin—A Natural Immunity Molecule
Molecules 2011, 16(8), 6992-7018; doi:10.3390/molecules16086992
Received: 23 July 2011 / Revised: 5 August 2011 / Accepted: 10 August 2011 / Published: 16 August 2011
Cited by 39 | PDF Full-text (453 KB)
Abstract
Lactoferrin, a multifunctional iron binding glycoprotein, plays an important role in immune regulation and defence mechanisms against bacteria, fungi and viruses. Lactoferrin’s iron withholding ability is related to inhibition of microbial growth as well as to modulation of motility, aggregation and biofilm [...] Read more.
Lactoferrin, a multifunctional iron binding glycoprotein, plays an important role in immune regulation and defence mechanisms against bacteria, fungi and viruses. Lactoferrin’s iron withholding ability is related to inhibition of microbial growth as well as to modulation of motility, aggregation and biofilm formation of pathogenic bacteria. Independently of iron binding capability, lactoferrin interacts with microbial, viral and cell surfaces thus inhibiting microbial and viral adhesion and entry into host cells. Lactoferrin can be considered not only a primary defense factor against mucosal infections, but also a polyvalent regulator which interacts in viral infectious processes. Its antiviral activity, demonstrated against both enveloped and naked viruses, lies in the early phase of infection, thus preventing entry of virus in the host cell. This activity is exerted by binding to heparan sulphate glycosaminoglycan cell receptors, or viral particles or both. Despite the antiviral effect of lactoferrin, widely demonstrated in vitro studies, few clinical trials have been carried out and the related mechanism of action is still under debate. The nuclear localization of lactoferrin in different epithelial human cells suggests that lactoferrin exerts its antiviral effect not only in the early phase of surface interaction virus-cell, but also intracellularly. The capability of lactoferrin to exert a potent antiviral activity, through its binding to host cells and/or viral particles, and its nuclear localization strengthens the idea that lactoferrin is an important brick in the mucosal wall, effective against viral attacks and it could be usefully applied as novel strategy for treatment of viral infections. Full article
(This article belongs to the Special Issue Antivirals)
Open AccessArticle Synthesis and Contractile Activity of Substituted 1,2,3,4-Tetrahydroisoquinolines
Molecules 2011, 16(8), 7019-7042; doi:10.3390/molecules16087019
Received: 22 July 2011 / Revised: 10 August 2011 / Accepted: 11 August 2011 / Published: 16 August 2011
Cited by 8 | PDF Full-text (510 KB)
Abstract
A series of different 1-monosubstituted and 1,1-disubstituted 1,2,3,4-tetrahydro-isoquinolines was synthesized in high yields from different ketoamides. We have developed a convenient method for the synthesis of disubstituted derivatives by interaction of ketoamides with organomagnesium compounds, followed by cyclization in the presence of [...] Read more.
A series of different 1-monosubstituted and 1,1-disubstituted 1,2,3,4-tetrahydro-isoquinolines was synthesized in high yields from different ketoamides. We have developed a convenient method for the synthesis of disubstituted derivatives by interaction of ketoamides with organomagnesium compounds, followed by cyclization in the presence of catalytic amounts of p-toluenesulfonic acid (PTSA). A number of substituents at the C-1 in the isoquinoline skeleton were introduced varying either carboxylic acid or organomagnesium compound. Some of the obtained 1,1-dialkyl-1,2,3,4-tetrahydro-isoquinolines possess contractile activity against guinea pig’s gastric smooth muscle preparations. Full article
(This article belongs to the Special Issue Heterocycles)
Figures

Open AccessArticle Development of a Highly Sensitive and Specific Immunoassay for Determining Chrysoidine, A Banned Dye, in Soybean Milk Film
Molecules 2011, 16(8), 7043-7057; doi:10.3390/molecules16087043
Received: 18 July 2011 / Revised: 7 August 2011 / Accepted: 11 August 2011 / Published: 17 August 2011
Cited by 9 | PDF Full-text (765 KB)
Abstract
A highly specific and sensitive indirect competitive enzyme-linked immunosorbent assay (icELISA)was developed for the first time for the detection of chrysoidine, a dye banned in soybean milk film. Two haptens with different spacer arms were synthesized to produce antibodies. Both homologous and [...] Read more.
A highly specific and sensitive indirect competitive enzyme-linked immunosorbent assay (icELISA)was developed for the first time for the detection of chrysoidine, a dye banned in soybean milk film. Two haptens with different spacer arms were synthesized to produce antibodies. Both homologous and heterologous immunoassay formats were compared to enhance the icELISA sensitivity. The heterologous icELISA exhibited better performance, with an IC50 (50% inhibitory concentration) of 0.33 ng/mL, a limit of detection (LOD, 10% inhibitory concentration) of 0.04 ng/mL, and a limit of quantitation (LOQ, 20%–80% inhibitory concentration) from 0.09 to 4.9 ng/mL. The developed icELISA was high sensitive and specific, and was applied to determine chrysoidine in fortified soybean milk film samples. The results were in good agreement with that obtained by high-performance liquid chromatography (HPLC) analyses. Full article
(This article belongs to the Section Organic Synthesis)
Open AccessCommunication Simple and Rapid Method for the Determination of Uric Acid-Independent Antioxidant Capacity
Molecules 2011, 16(8), 7058-7067; doi:10.3390/molecules16087058
Received: 22 July 2011 / Revised: 11 August 2011 / Accepted: 15 August 2011 / Published: 17 August 2011
Cited by 13 | PDF Full-text (460 KB)
Abstract
Determination of the relative contribution of uric acid level increases to the total measured antioxidative activity could be very useful for testing antioxidative products and their effect on human health. The aim of this report is to present a simple spectrophotometric method [...] Read more.
Determination of the relative contribution of uric acid level increases to the total measured antioxidative activity could be very useful for testing antioxidative products and their effect on human health. The aim of this report is to present a simple spectrophotometric method that combines the measurement of total antioxidative capacity of a sample by ferric reducing/antioxidative power (FRAP) assay, with the uricase-reaction (specific elimination of uric acid), in order to establish and correct for the contribution of uric acid in FRAP values. We measured FRAP values, with (uric acid-independent antioxidant capacity, TAC-UA) and without (total antioxidant capacity, TAC) uricase treatment, and expressed it as μmol/L of uric acid equivalents. In such way, it was possible to determine both total and uric acid-independent antioxidant capacity, plasma uric acid (UA, as the difference between TAC and TAC-UA), and the ratio of the uric acid in total antioxidant capacity (UA/TAC). Full article
(This article belongs to the Section Medicinal Chemistry)
Open AccessArticle Activity and Stability Studies of Verbascoside, a Novel Antioxidant, in Dermo-Cosmetic and Pharmaceutical Topical Formulations
Molecules 2011, 16(8), 7068-7080; doi:10.3390/molecules16087068
Received: 27 June 2011 / Revised: 10 August 2011 / Accepted: 11 August 2011 / Published: 18 August 2011
Cited by 29 | PDF Full-text (451 KB)
Abstract
We here report the results of our investigations carried out on verbascoside, a phenylpropanoid glycoside known for its antioxidant, anti-inflammatory and photoprotective actions. Verbascoside was obtained from Buddleia davidii meristematic cells, obtained in turn using a sustainable biotechnology platform which employs an [...] Read more.
We here report the results of our investigations carried out on verbascoside, a phenylpropanoid glycoside known for its antioxidant, anti-inflammatory and photoprotective actions. Verbascoside was obtained from Buddleia davidii meristematic cells, obtained in turn using a sustainable biotechnology platform which employs an in vitro plant cell culture technology. Verbascoside was first investigated to assess the behaviour of the active ingredient in solution or in finished preparations, in view of its potential topical use, especially in skin protection. Stability studies were performed by HPLC, and a PCL assay was adopted to determine the radical scavenging activity toward superoxide anion. The high hydrophilic character of verbascoside, suggested in a somewhat limited range of possible applications, leading us to explore its derivatization to obtain the semi-synthetic derivative VPP, an acyl derivative of verbascoside, with an improved range of applications due to its lower hydrophilic profile. Alone, VPP revealed increased antioxidant activity, both as an active ingredient and in dermocosmetic preparations. Stability studies showed a greater stability of VPP in lipophilic vehicles, whereas the parent verbascoside proved more stable in an O/W emulsions. Verbascoside was also stable in suppositories, an interesting pharmaceutical form for possible applications in treatment of inflammation of the intestinal mucosa. Full article
(This article belongs to the Section Medicinal Chemistry)
Open AccessArticle Synthesis and Electrophilic Substitutions of Novel Pyrazolo[1,5-c]-1,2,4-triazolo[4,3-a]pyrimidines
Molecules 2011, 16(8), 7081-7096; doi:10.3390/molecules16087081
Received: 30 June 2011 / Revised: 1 August 2011 / Accepted: 4 August 2011 / Published: 18 August 2011
Cited by 4 | PDF Full-text (454 KB)
Abstract
5-Aryl-7-hydrazino-2-phenylpyrazolo[1,5-c]pyrimidines 1 were used as precursors for the preparation of a new series of 5-aryl-8-phenylpyrazolo[1,5-c]-1,2,4- triazolo[4,3-a]pyrimidines 2. The reactions of 2 with certain electrophilic reagents gave the respective 6-substituted derivatives 3-5 rather than [...] Read more.
5-Aryl-7-hydrazino-2-phenylpyrazolo[1,5-c]pyrimidines 1 were used as precursors for the preparation of a new series of 5-aryl-8-phenylpyrazolo[1,5-c]-1,2,4- triazolo[4,3-a]pyrimidines 2. The reactions of 2 with certain electrophilic reagents gave the respective 6-substituted derivatives 3-5 rather than the 7-isomeric products. Formylation of the key compounds 1 with ethyl formate yielded the formyl derivatives 6. Furthermore, boiling of compounds 1 with acetic acid afforded 7-acetylhydrazino-5-aryl-2-phenylpyrazolo[1,5-c]pyrimidines 7. Bromination of 7 yielded the dibromo- derivatives 8, while their iodination and nitration gave the monosubstituted derivatives 9 and 10, respectively. Also, treatment of 1 with boiling acetic anhydride yielded the triacetyl derivatives 11. The structure of synthesized products was confirmed by elemental analyses, IR, 1H NMR and MS spectra. Full article
(This article belongs to the Special Issue Heterocycles)
Figures

Open AccessArticle Alkaloids from Hippeastrum papilio
Molecules 2011, 16(8), 7097-7104; doi:10.3390/molecules16087097
Received: 9 June 2011 / Revised: 20 July 2011 / Accepted: 26 July 2011 / Published: 18 August 2011
Cited by 17 | PDF Full-text (438 KB)
Abstract
Galanthamine, an acetylcholinesterase inhibitor marketed as a hydrobromide salt (Razadyne®, Reminyl®) for the treatment of Alzheimer’s disease (AD), is obtained from Amaryllidaceae plants, especially those belonging to the genera Leucojum, Narcissus, Lycoris and Ungernia. The growing demand for galanthamine [...] Read more.
Galanthamine, an acetylcholinesterase inhibitor marketed as a hydrobromide salt (Razadyne®, Reminyl®) for the treatment of Alzheimer’s disease (AD), is obtained from Amaryllidaceae plants, especially those belonging to the genera Leucojum, Narcissus, Lycoris and Ungernia. The growing demand for galanthamine has prompted searches for new sources of this compound, as well as other bioactive alkaloids for the treatment of AD. In this paper we report the isolation of the new alkaloid 11β-hydroxygalanthamine, an epimer of the previously isolated alkaloid habranthine, which was identified using NMR techniques. It has been shown that 11β-hydroxygalanthamine has an important in vitro acetylcholinesterase inhibitory activity. Additionally, Hippeastrum papilio yielded substantial quantities of galanthamine. Full article
(This article belongs to the Special Issue Alkaloids: Novel Therapeutic Perspectives)
Open AccessArticle Chemical Profile and Biological Potential of Non-Polar Fractions from Centroceras clavulatum (C. Agardh) Montagne (Ceramiales, Rhodophyta)
Molecules 2011, 16(8), 7105-7114; doi:10.3390/molecules16087105
Received: 18 June 2011 / Revised: 3 August 2011 / Accepted: 8 August 2011 / Published: 19 August 2011
Cited by 5 | PDF Full-text (369 KB)
Abstract
The present study reports the Gas Chromatography-Mass Spectrometry (GC-MS) evaluation of the hexanes and dichloromethane fractions from extracts of the red alga Centroceras clavulatum (C. Agardh) Montagne. Twenty three compounds were identified, totaling ca. 42% of both fractions (0.18 g mass extract). [...] Read more.
The present study reports the Gas Chromatography-Mass Spectrometry (GC-MS) evaluation of the hexanes and dichloromethane fractions from extracts of the red alga Centroceras clavulatum (C. Agardh) Montagne. Twenty three compounds were identified, totaling ca. 42% of both fractions (0.18 g mass extract). The main constituents of the fractions were hexadecanoic acid (17.6%) and pentadecanoic acid (15.9%). Several secondary metabolites with interesting biological activity, such as (-)-loliolide, neophytadiene, phytol were identified. In addition, several classes of secondary metabolites, including phenolic compounds (e.g., phenylacetic acid), terpene derivatives, fatty acids, halogenated compound (e.g., 2-chlorocyclohexenol), lignoids, steroids, esters, amides (e.g., hexadecanamide), ketones, carboxylic acids, aldehydes and alcohols were observed. The occurrence of several of these structural classes is described for the first time in this species. The same fractions analyzed by GC-MS, and a separate set of polar fractions, were evaluated against two life cycle stages (epimastigote and trypomastigote forms) of the protozoan Trypanosoma cruzi and against phytopatogenic fungi Cladosporium cladosporiodes and C. sphaerospermum. The dichloromethane fraction was active against both T. cruzi forms (epimastigote IC50 = 19.1 μg.mL−1 and trypomastigote IC50 = 76.2 μg.mL−1). The hexanes and ethyl acetate fractions also displayed activity against both fungi species (200 μg) by TLC-bioautography. Full article
(This article belongs to the collection Bioactive Compounds)
Open AccessArticle Essential Oil Composition of the Different Parts and In Vitro Shoot Culture of Eryngium planum L.
Molecules 2011, 16(8), 7115-7124; doi:10.3390/molecules16087115
Received: 22 June 2011 / Revised: 8 August 2011 / Accepted: 8 August 2011 / Published: 19 August 2011
Cited by 12 | PDF Full-text (436 KB)
Abstract
The essential oils obtained by hydrodistillation from the different parts (inflorescence, stalk leaves, rosette leaves and root) as well as from in vitro shoot culture of Eryngium planum L. were analyzed by GC-FID-MS in respect to their chemical composition. The different parts [...] Read more.
The essential oils obtained by hydrodistillation from the different parts (inflorescence, stalk leaves, rosette leaves and root) as well as from in vitro shoot culture of Eryngium planum L. were analyzed by GC-FID-MS in respect to their chemical composition. The different parts of E. planum and in vitro shoots showed different yields. The part with higher amount was the inflorescences, followed by the stalk leaves and in vitro shoots, rosette leaves and finally roots. The essential oils obtained from rosette leaves and in vitro-derived rosettes had totally different composition. Quantitative differences were also found between compounds of intact plant organs. The main components of stalk leaf oil and rosette leaf oil were monoterpene (limonene, α- and β-pinene) and sesquiterpene hydrocarbons. In inflorescence oil cis-chrysanthenyl acetate (43.2%) was accompanied by other esters (propionate, butanoate, hexanoate and octanoate) and numerous oxygenated sesquiterpenes. Root oil and in vitro shoot oil contained mainly (Z)-falcarinol and 2,3,4-trimethylbenzaldehyde. This is the first report on the chemical composition of this species. Full article
(This article belongs to the Section Natural Products)
Open AccessCommunication Azaphenanthrene Alkaloids with Antitumoral Activity from Anaxagorea dolichocarpa Sprague & Sandwith (Annonaceae)
Molecules 2011, 16(8), 7125-7131; doi:10.3390/molecules16087125
Received: 27 June 2011 / Revised: 26 July 2011 / Accepted: 4 August 2011 / Published: 22 August 2011
Cited by 6 | PDF Full-text (432 KB)
Abstract
Phytochemical investigation of Anaxagorea dolichocarpa Sprague & Sandwith led to isolation of three azaphenanthrene alkaloids: eupolauramine, sampangine and imbiline 1. Their chemical structures were established on the basis of spectroscopic data from IR, HR-ESI-MS, NMR (including 2D experiments) and comparison with the literature. Sampangine and imbiline 1 are being described in the Anaxagorea genus for the first time. Eupolauramine and sampangine show concentration-dependent antitumoral activity in leukemic cells K562 with IC50 of 18.97 and 10.95 µg/mL, respectively. Full article
(This article belongs to the Special Issue Alkaloids: Novel Therapeutic Perspectives)
Open AccessArticle Anti-Inflammatory Effect of Myristicin on RAW 264.7 Macrophages Stimulated with Polyinosinic-Polycytidylic Acid
Molecules 2011, 16(8), 7132-7142; doi:10.3390/molecules16087132
Received: 15 July 2011 / Revised: 8 August 2011 / Accepted: 18 August 2011 / Published: 22 August 2011
Cited by 22 | PDF Full-text (1056 KB)
Abstract
Myristicin (1-allyl-5-methoxy-3,4-methylenedioxybenzene) is an active aromatic compound found in nutmeg (the seed of Myristica fragrans), carrot, basil, cinnamon, and parsley. Myristicin has been known to have anti-cholinergic, antibacterial, and hepatoprotective effects, however, the effects of myristicin on virus-stimulated macrophages are not fully reported. In this study, the anti-inflammatory effect of myristicin on double-stranded RNA (dsRNA)-stimulated macrophages was examined. Myristicin did not reduce the cell viability of RAW 264.7 mouse macrophages at concentrations of up to 50 µM. Myristicin significantly inhibited the production of calcium, nitric oxide (NO), interleukin (IL)-6, IL-10, interferon inducible protein-10, monocyte chemotactic protein (MCP)-1, MCP-3, granulocyte-macrophage colony-stimulating factor, macrophage inflammatory protein (MIP)-1α, MIP-1β, and leukemia inhibitory factor in dsRNA [polyinosinic-polycytidylic acid]-induced RAW 264.7 cells (P < 0.05). In conclusion, myristicin has anti-inflammatory properties related with its inhibition of NO, cytokines, chemokines, and growth factors in dsRNA-stimulated macrophages via the calcium pathway. Full article
(This article belongs to the Special Issue Antivirals)
Figures

Open AccessArticle Physico-Chemical Characteristics and Functional Properties of Chitin and Chitosan Produced by Mucor circinelloides Using Yam Bean as Substrate
Molecules 2011, 16(8), 7143-7154; doi:10.3390/molecules16087143
Received: 28 July 2011 / Accepted: 8 August 2011 / Published: 23 August 2011
Cited by 13 | PDF Full-text (426 KB)
Abstract
Microbiological processes were used for chitin and chitosan production by Mucor circinelloides (UCP 050) grown in yam bean (Pachyrhizus erosus L. Urban) medium. The polysaccharides were extracted by alkali–acid treatment and structural investigations by X-ray diffraction, Fourier transform IR analysis, viscosity [...] Read more.
Microbiological processes were used for chitin and chitosan production by Mucor circinelloides (UCP 050) grown in yam bean (Pachyrhizus erosus L. Urban) medium. The polysaccharides were extracted by alkali–acid treatment and structural investigations by X-ray diffraction, Fourier transform IR analysis, viscosity and thermal analysis by TG, DTG, and DTA were done. The highest biomass yield (20.7 g/L) was obtained at 96 hours. The highest levels of chitosan (64 mg/g) and chitin (500 mg/g) were produced at 48 and 72 hours, respectively. It was demonstrated that yam bean shows great potential as an economic medium and it is possible to achieve a good yield of chitosan with chemical properties that enable its use in biotechnological applications. Full article
(This article belongs to the Section Natural Products)
Open AccessArticle The Growth Suppressing Effects of Girinimbine on Hepg2 Involve Induction of Apoptosis and Cell Cycle Arrest
Molecules 2011, 16(8), 7155-7170; doi:10.3390/molecules16087155
Received: 18 May 2011 / Revised: 6 July 2011 / Accepted: 3 August 2011 / Published: 23 August 2011
Cited by 19 | PDF Full-text (2020 KB)
Abstract
Murraya koenigii is an edible herb widely used in folk medicine. Here we report that girinimbine, a carbazole alkaloid isolated from this plant, inhibited the growth and induced apoptosis in human hepatocellular carcinoma, HepG2 cells. The MTT and LDH assay results showed [...] Read more.
Murraya koenigii is an edible herb widely used in folk medicine. Here we report that girinimbine, a carbazole alkaloid isolated from this plant, inhibited the growth and induced apoptosis in human hepatocellular carcinoma, HepG2 cells. The MTT and LDH assay results showed that girinimbine decreased cell viability and increased cytotoxicity in a dose-and time-dependent manner selectively. Girinimbine-treated HepG2 cells showed typical morphological features of apoptosis, as observed from normal inverted microscopy and Hoechst 33342 assay. Furthermore, girinimbine treatment resulted in DNA fragmentation and elevated levels of caspase-3 in HepG2 cells. Girinimbine treatment also displayed a time-dependent accumulation of the Sub-G0/G1 peak (hypodiploid) and caused G0/G1-phase arrest. Together, these results demonstrated for the first time that girinimbine could effectively induce programmed cell death in HepG2 cells and suggests the importance of conducting further investigations in preclinical human hepatocellular carcinoma models, especially on in vivo efficacy, to promote girinimbine for use as an anticancer agent against hepatocellular carcinoma. Full article
(This article belongs to the Special Issue Alkaloids: Novel Therapeutic Perspectives)
Open AccessArticle Optimized Enzymatic Synthesis of Hesperidin Fatty Acid Esters in a Two-Phase System Containing Ionic Liquid
Molecules 2011, 16(8), 7171-7182; doi:10.3390/molecules16087171
Received: 29 June 2011 / Revised: 16 August 2011 / Accepted: 17 August 2011 / Published: 23 August 2011
Cited by 7 | PDF Full-text (545 KB)
Abstract
Response surface methodology (RSM) based on a five-level, three-variable central composite design (CCD) was employed for modeling and optimizing the conversion yield of the enzymatic acylation of hesperidin with decanoic acid using immobilized Candida antarctica lipase B (CALB) in a two-phase system [...] Read more.
Response surface methodology (RSM) based on a five-level, three-variable central composite design (CCD) was employed for modeling and optimizing the conversion yield of the enzymatic acylation of hesperidin with decanoic acid using immobilized Candida antarctica lipase B (CALB) in a two-phase system containing [bmim]BF4. The three variables studied (molar ratio of hesperidin to decanoic acid, [bmim]BF4/acetone ratio and lipase concentration) significantly affected the conversion yield of acylated hesperidin derivative. Verification experiments confirmed the validity of the predicted model. The lipase showed higher conversion degree in a two-phase system using [bmim]BF4 and acetone compared to that in pure acetone. Under the optimal reaction conditions carried out in a single-step biocatalytic process when the water content was kept lower than 200 ppm, the maximum acylation yield was 53.6%. Full article
(This article belongs to the Special Issue Enzyme-Catalyzed Reactions)

Review

Jump to: Research, Other

Open AccessReview Recent Advances in the Application of SelectfluorTMF-TEDA-BF4 as a Versatile Mediator or Catalyst in Organic Synthesis
Molecules 2011, 16(8), 6432-6464; doi:10.3390/molecules16086432
Received: 14 June 2011 / Revised: 5 July 2011 / Accepted: 19 July 2011 / Published: 29 July 2011
Cited by 27 | PDF Full-text (1157 KB)
Abstract
SelectfluorTM F-TEDA-BF4 (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo [2.2.2]octane bis(tetrafluoroborate) is not only one of the most efficient and popular reagents for electrophilic fluorination, but as a strong oxidant is also a convenient mediator or catalyst of several “fluorine-free” functionalizations of organic compounds. Its applications [...] Read more.
SelectfluorTM F-TEDA-BF4 (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo [2.2.2]octane bis(tetrafluoroborate) is not only one of the most efficient and popular reagents for electrophilic fluorination, but as a strong oxidant is also a convenient mediator or catalyst of several “fluorine-free” functionalizations of organic compounds. Its applications as a mediator in transformations of oxidizable functional groups or gold-catalyzed C-C and C-heteroatom oxidative coupling reactions, a catalyst in formation of various heterocyclic rings, a reagent or catalyst of various functionalizations of electron-rich organic compounds (iodination, bromination, chlorination, nitration, thiocyanation, sulfenylation, alkylation, alkoxylation), a catalyst of one-pot-multi-component coupling reactions, a catalyst of regioselective ring opening of epoxides, a deprotection reagent for various protecting groups, and a mediator for stereoselective rearrangement processes of bicyclic compounds are reviewed and discussed. Full article
(This article belongs to the Special Issue Fluorine Chemistry 2016)
Figures

Open AccessReview Berberine: A Potential Multipotent Natural Product to Combat Alzheimer’s Disease
Molecules 2011, 16(8), 6732-6740; doi:10.3390/molecules16086732
Received: 11 July 2011 / Revised: 23 July 2011 / Accepted: 2 August 2011 / Published: 9 August 2011
Cited by 48 | PDF Full-text (150 KB)
Abstract
With the accelerated aging of human society Alzheimer’s disease (AD) has become one of the most threatening diseases in the elderly. However, there is no efficient therapeutic agent to combat AD. Berberine is a natural isoquinoline alkaloid that possesses a wide range [...] Read more.
With the accelerated aging of human society Alzheimer’s disease (AD) has become one of the most threatening diseases in the elderly. However, there is no efficient therapeutic agent to combat AD. Berberine is a natural isoquinoline alkaloid that possesses a wide range of pharmacological effects. In the present paper, we review the multiple activities of berberine, including antioxidant, acetylcholinesterase and butyrylcholinesterase inhibitory, monoamine oxidase inhibitory, amyloid-b peptide level-reducing and cholesterol-lowering activities, which suggest that berberine may act as a promising multipotent agent to combat AD. Full article
(This article belongs to the Section Natural Products)
Open AccessReview Cardanol-Based Materials as Natural Precursors for Olefin Metathesis
Molecules 2011, 16(8), 6871-6882; doi:10.3390/molecules16086871
Received: 4 May 2011 / Revised: 8 July 2011 / Accepted: 12 July 2011 / Published: 11 August 2011
Cited by 24 | PDF Full-text (443 KB)
Abstract
Cardanol is a renewable, low cost natural material, widely available as a by-product of the cashew industry. It is a mixture of 3-n-pentadecylphenol, 3-(pentadeca-8-enyl)phenol, 3-(pentadeca-8,11-dienyl)phenol and 3-(pentadeca-8,11,14-trienyl)phenol. Olefin metathesis (OM) reaction on cardanol is an important class of reactions that [...] Read more.
Cardanol is a renewable, low cost natural material, widely available as a by-product of the cashew industry. It is a mixture of 3-n-pentadecylphenol, 3-(pentadeca-8-enyl)phenol, 3-(pentadeca-8,11-dienyl)phenol and 3-(pentadeca-8,11,14-trienyl)phenol. Olefin metathesis (OM) reaction on cardanol is an important class of reactions that allows for the synthesis of new olefins that are sometime impossible to prepare via other methods. The application of this natural and renewable material to both academic and industrial research will be discussed. Full article
(This article belongs to the Special Issue Olefin Metathesis and Its Application)

Other

Jump to: Research, Review

Open AccessShort Note Isoconiferoside, a New Phenolic Glucoside from Seeds of Panax ginseng
Molecules 2011, 16(8), 6577-6581; doi:10.3390/molecules16086577
Received: 27 June 2011 / Revised: 29 July 2011 / Accepted: 2 August 2011 / Published: 4 August 2011
Cited by 1 | PDF Full-text (327 KB)
Abstract A new phenolic glucoside, isoconiferoside (1), was isolated from the seeds of Panax ginseng (Araliaceae). The structure was determined to be 9-O-[b-D-glucopyranosyl-(1®6)-b-D-glucopyranosyl]-trans-coniferyl alcohol based on spectroscopic analyses (1H- and 13C-NMR, DEPT, COSY, HMQC, and HMBC) and acid hydrolysis. Full article
(This article belongs to the Section Natural Products)

Journal Contact

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