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Molecules, Volume 18, Issue 7 (July 2013), Pages 7336-8711

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Open AccessArticle Bioactive Phenylpropanoid Glycosides from Tabebuia avellanedae
Molecules 2013, 18(7), 7336-7345; doi:10.3390/molecules18077336
Received: 22 April 2013 / Revised: 14 June 2013 / Accepted: 18 June 2013 / Published: 24 June 2013
Cited by 2 | PDF Full-text (200 KB) | HTML Full-text | XML Full-text
Abstract
Three novel phenylpropanoid glycosides 2, 5, 6 were isolated from water extract of Tabebuia avellanedae, together with three known phenylpropanoid glycosides 1, 3, 4. All compounds were identified on the basis of spectroscopic analysis and chemical [...] Read more.
Three novel phenylpropanoid glycosides 2, 5, 6 were isolated from water extract of Tabebuia avellanedae, together with three known phenylpropanoid glycosides 1, 3, 4. All compounds were identified on the basis of spectroscopic analysis and chemical methods and, for known compounds, by comparison with published data. All isolated compounds showed strong antioxidant activity in the DPPH assay, and compound 5 give the highest antioxidant activity among all compounds, with an IC50 of 0.12 µM. All compounds exhibited moderate inhibitory effect on cytochrome CYP3A4 enzyme. Full article
(This article belongs to the Section Natural Products)
Open AccessArticle Oligonucleotide Tagging for Copper-Free Click Conjugation
Molecules 2013, 18(7), 7346-7363; doi:10.3390/molecules18077346
Received: 19 April 2013 / Revised: 24 May 2013 / Accepted: 5 June 2013 / Published: 24 June 2013
Cited by 9 | PDF Full-text (704 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Copper-free click chemistry between cyclooctynes and azide is a mild, fast and selective technology for conjugation of oligonucleotides. However, technology for site-specific introduction of the requisite probes by automated protocols is scarce, while the reported cyclooctynes are large and hydrophobic. In this [...] Read more.
Copper-free click chemistry between cyclooctynes and azide is a mild, fast and selective technology for conjugation of oligonucleotides. However, technology for site-specific introduction of the requisite probes by automated protocols is scarce, while the reported cyclooctynes are large and hydrophobic. In this work, it is demonstrated that the introduction of bicyclo[6.1.0]nonyne (BCN) into synthetic oligonucleotides is feasible by standard solid-phase phosphoramidite chemistry. A range of phosphoramidite building blocks is presented for incoporation of BCN or azide, either on-support or in solution. The usefulness of the approach is demonstrated by the straightforward and high-yielding conjugation of the resulting oligonucleotides, including biotinylation, fluorescent labeling, dimerization and attachment to polymer. Full article
(This article belongs to the Section Organic Synthesis)
Open AccessCommunication TDAE Strategy for the Synthesis of 2,3-Diaryl N-Tosylaziridines
Molecules 2013, 18(7), 7364-7375; doi:10.3390/molecules18077364
Received: 27 May 2013 / Revised: 14 June 2013 / Accepted: 18 June 2013 / Published: 24 June 2013
Cited by 1 | PDF Full-text (285 KB)
Abstract We report herein an original and rapid synthesis of 2,3-diaryl N-tosylaziridines by TDAE strategy starting from ortho- or para-nitro(dichloromethyl)benzene derivatives and N-tosylimines. A mixture of cis/trans isomers was isolated from 1-(dichloromethyl)-4-nitrobenzene, whereas only trans-aziridines were obtained from ortho-nitro derivatives. Full article
(This article belongs to the Section Organic Synthesis)
Open AccessArticle Ethanol Extract of Atractylodes macrocephala Protects Bone Loss by Inhibiting Osteoclast Differentiation
Molecules 2013, 18(7), 7376-7388; doi:10.3390/molecules18077376
Received: 27 May 2013 / Revised: 19 June 2013 / Accepted: 19 June 2013 / Published: 24 June 2013
Cited by 4 | PDF Full-text (2265 KB) | HTML Full-text | XML Full-text
Abstract
The rhizome of Atractylodes macrocephala has been used mainly in Traditional Chinese Medicine for invigorating the functions of the stomach and spleen. In the present study, we investigated the inhibitory effect of the 70% ethanol extract of the rhizome of Atractylodes macrocephala [...] Read more.
The rhizome of Atractylodes macrocephala has been used mainly in Traditional Chinese Medicine for invigorating the functions of the stomach and spleen. In the present study, we investigated the inhibitory effect of the 70% ethanol extract of the rhizome of Atractylodes macrocephala (AMEE) on osteoclast differentiation. We found that AMEE inhibits osteoclast differentiation from its precursors induced by receptor activator of nuclear factor-κB ligand (RANKL), an essential cytokine required for osteoclast differentiation. AMEE attenuated RANKL-induced activation of NF-κB signaling pathway, subsequently inhibiting the induction of osteoclastogenic transcription factors, c-Fos and nuclear factor of activated T cells cytoplasmic 1. Consistent with the in vitro results, administration of AMEE protected RANKL-induced bone loss in mice. We also identified atractylenolide I and II as active constituents contributing to the anti-osteoclastogenic effect of AMEE. Taken together, our results demonstrate that AMEE has a protective effect on bone loss via inhibiting osteoclast differentiation and suggest that AMEE may be useful in preventing and treating various bone diseases associated with excessive bone resorption. Full article
(This article belongs to the Section Natural Products)
Open AccessArticle Synthesis and Evaluation of Some 17-Acetamidoandrostane and N,N-Dimethyl-7-deoxycholic Amide Derivatives as Cytotoxic Agents: Structure/Activity Studies
Molecules 2013, 18(7), 7436-7447; doi:10.3390/molecules18077436
Received: 9 May 2013 / Revised: 13 June 2013 / Accepted: 18 June 2013 / Published: 26 June 2013
Cited by 2 | PDF Full-text (240 KB) | HTML Full-text | XML Full-text
Abstract
Using pregnenolone and 7-deoxycholic acid as starting materials, some 17-acetamidoandrostane and N,N-dimethyl-7-deoxycholic amide derivatives were synthesized. The cytotoxicity of the synthesized compounds was tested in vitro against two tumor cell lines: SGC 7901 (human gastric carcinoma) and Bel 7404 (human liver [...] Read more.
Using pregnenolone and 7-deoxycholic acid as starting materials, some 17-acetamidoandrostane and N,N-dimethyl-7-deoxycholic amide derivatives were synthesized. The cytotoxicity of the synthesized compounds was tested in vitro against two tumor cell lines: SGC 7901 (human gastric carcinoma) and Bel 7404 (human liver carcinoma). The result showed that the blockage of the interaction of the amide group with outside groups might cause a decrease of the cytotoxicity, and an O-benzyloximino group at the 3-position of N,N-dimethyl-7-deoxycholic amide could enhance the cytotoxic activity of the compound. The information obtained from the studies provides the structure-activity relationship for these compounds and may be useful for the design of novel chemotherapeutic drugs. Full article
Open AccessArticle A Novel 3a-p-Nitrobenzoylmultiflora-7:9(11)-diene-29-benzoate and Two New Triterpenoids from the Seeds of Zucchini (Cucurbita pepo L)
Molecules 2013, 18(7), 7448-7459; doi:10.3390/molecules18077448
Received: 6 June 2013 / Revised: 21 June 2013 / Accepted: 21 June 2013 / Published: 26 June 2013
Cited by 2 | PDF Full-text (381 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Three novel multiflorane-type triterpenoids, 3a-p-nitrobenzoylmultiflora-7:9(11)-diene-29-benzoate (1), 3a-acetoxymultiflora-7:9(11)-diene-29-benzoate (2), and 3a-acetoxymultiflora-5(6):7:9(11)-triene-29-benzoate (3), along with two known related compounds 4 and 5 were isolated from the seeds of zucchini (Cucurbita pepo L). Their structures were [...] Read more.
Three novel multiflorane-type triterpenoids, 3a-p-nitrobenzoylmultiflora-7:9(11)-diene-29-benzoate (1), 3a-acetoxymultiflora-7:9(11)-diene-29-benzoate (2), and 3a-acetoxymultiflora-5(6):7:9(11)-triene-29-benzoate (3), along with two known related compounds 4 and 5 were isolated from the seeds of zucchini (Cucurbita pepo L). Their structures were determined on the basis of 1D and 2D NMR spectroscopy and HREIMS. Triterpenoids possessing a nitro group were not isolated previously. Full article
(This article belongs to the Section Natural Products)
Open AccessArticle Study on the Potential Toxicity of a Thymoquinone-Rich Fraction Nanoemulsion in Sprague Dawley Rats
Molecules 2013, 18(7), 7460-7472; doi:10.3390/molecules18077460
Received: 27 May 2013 / Revised: 18 June 2013 / Accepted: 19 June 2013 / Published: 26 June 2013
Cited by 6 | PDF Full-text (610 KB) | HTML Full-text | XML Full-text
Abstract
Toxicological studies constitute an essential part of the effort in developing an herbal medicine into a drug product. A newly developed thymoquinone-rich fraction nanoemulsion (TQRFNE) has been prepared using a high pressure homogenizer. The purpose of this study was to investigate the [...] Read more.
Toxicological studies constitute an essential part of the effort in developing an herbal medicine into a drug product. A newly developed thymoquinone-rich fraction nanoemulsion (TQRFNE) has been prepared using a high pressure homogenizer. The purpose of this study was to investigate the potential acute toxicity of this nanoemulsion in Sprague Dawley rats. The acute toxicity studies were conducted as per the OECD guidelines 425, allowing for the use of test dose limit of 20 mL TQRFNE (containing 44.5 mg TQ)/kg. TQRFNE and distilled water (DW) as a control were administered orally to both sexes of rats on Day 0 and observed for 14 days. All the animals appeared normal, and healthy throughout the study. There was no observed mortality or any signs of toxicity during the experimental period. The effects of the TQRFNE and DW groups on general behavior, body weight, food and water consumption, relative organ weight, hematology, histopathology, and clinical biochemistry were measured. All the parameters measured were unaffected as compared to the control (DW) group. The administration of 20 mL TQRFNE /kg was not toxic after an acute exposure. Full article
Open AccessArticle Effects of Combined Elicitors on Tanshinone Metabolic Profiling and SmCPS Expression in Salvia miltiorrhiza Hairy Root Cultures
Molecules 2013, 18(7), 7473-7485; doi:10.3390/molecules18077473
Received: 23 April 2013 / Revised: 21 June 2013 / Accepted: 24 June 2013 / Published: 27 June 2013
Cited by 11 | PDF Full-text (674 KB) | HTML Full-text | XML Full-text
Abstract
Tanshinones are abietane-type norditerpenoid quinone natural products found in a well-known traditional Chinese medicinal herb, Salvia miltiorrhiza Bunge. The copalyl diphosphate synthase of S. miltiorrhiza (SmCPS) is the key enzyme in the first step for transformation of geranylgeranyl diphosphate (GGPP) into miltiradiene, [...] Read more.
Tanshinones are abietane-type norditerpenoid quinone natural products found in a well-known traditional Chinese medicinal herb, Salvia miltiorrhiza Bunge. The copalyl diphosphate synthase of S. miltiorrhiza (SmCPS) is the key enzyme in the first step for transformation of geranylgeranyl diphosphate (GGPP) into miltiradiene, which has recently been identified as the precursor of tanshinones. Based on previous gene-to-metabolite network, this study examined the influences of various combined elicitors on the expression of SmCPS and production of tanshinones in S. miltiorrhiza hairy root cultures. Combined elicitors were composed of three classes of elicitors, a heavy metal ion (Ag+), a polysaccharide (yeast extract, YE), and a plant response-signalling compound (methyl jasmonate, MJ). YE + Ag+, Ag+ + MJ, YE + MJ, and YE + Ag+ + MJ were the combinations we tested. The effect of elicitors on the SmCPS expression level was detected by quantitative real-time PCR (qRT-PCR), and the tanshinones accumulation responses to elicitation were analysed by Ultra Performance Liquid Chromatography (UPLC) metabolite profiling. Of these combined elicitors, the expression of SmCPS was significantly enhanced by elicitation, especially at 24 h and 36 h. Of four tanshinones detected, the contents of cryptotanshinone and dihydrotanshinone I were enhanced by treatment with YE + Ag+, Ag+ + MJ, and YE + Ag+ + MJ. Our results indicate that appropriate combined elicitors can enhance tanshinones production in hairy root cultures. Full article
Open AccessCommunication A New Resveratrol Trimer from the Roots and Stems of Vitis wenchowensis
Molecules 2013, 18(7), 7486-7491; doi:10.3390/molecules18077486
Received: 8 June 2013 / Revised: 18 June 2013 / Accepted: 19 June 2013 / Published: 27 June 2013
Cited by 5 | PDF Full-text (181 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Phytochemical constituents of Vitis wenchowensis were investigated for the first time. A new resveratrol trimer, wenchowenol (1), was isolated from the roots and stems of Vitis wenchowensis along with four known stilbenoids 2–5. The structure and relative configuration of [...] Read more.
Phytochemical constituents of Vitis wenchowensis were investigated for the first time. A new resveratrol trimer, wenchowenol (1), was isolated from the roots and stems of Vitis wenchowensis along with four known stilbenoids 2–5. The structure and relative configuration of 1 were established on the basis of spectral evidence, especially HMBC and NOESY experiments. It showed potent antioxidant activity against DPPH (1,1-diphenyl-2-picrylhydrazyl) radical. Full article
(This article belongs to the Section Natural Products)
Open AccessArticle Spectroscopic and Theoretical Studies of Some 3-(4′-Substituted phenylsulfanyl)-1-methyl-2-piperidones
Molecules 2013, 18(7), 7492-7509; doi:10.3390/molecules18077492
Received: 31 May 2013 / Revised: 20 June 2013 / Accepted: 21 June 2013 / Published: 27 June 2013
Cited by 3 | PDF Full-text (644 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
The analysis of the IR carbonyl bands of some 3-(4′-substituted phenylsulfanyl)-1-methyl-2-piperidones 16 bearing substituents: NO2 (compound 1), Br (compound 2), Cl (compound 3), H (compound 4) Me (compound 5) and OMe (compound 6) [...] Read more.
The analysis of the IR carbonyl bands of some 3-(4′-substituted phenylsulfanyl)-1-methyl-2-piperidones 16 bearing substituents: NO2 (compound 1), Br (compound 2), Cl (compound 3), H (compound 4) Me (compound 5) and OMe (compound 6) supported by B3LYP/6-31+G(d,p) and PCM calculations along with NBO analysis (for compound 4) and X-ray diffraction (for 2) indicated the existence of two stable conformations, i.e., axial (ax) and equatorial (eq), the former corresponding to the most stable and the least polar one in the gas phase calculations. The sum of the energy contributions of the orbital interactions (NBO analysis) and the electrostatic interactions correlate well with the populations and the νCO frequencies of the ax and eq conformers found in the gas phase. Unusually, in solution of the non-polar solvents n-C6H14 and CCl4, the more intense higher IR carbonyl frequency can be ascribed to the ax conformer, while the less intense lower IR doublet component to the eq one. The same νCO frequency trend also holds in polar solvents, that is νCO (eq)< νCO (ax). However, a reversal of the ax/eq intensity ratio occurs going from non-polar to polar solvents, with the ax conformer component that progressively decreases with respect to the eq one in CHCl3 and CH2Cl2, and is no longer detectable in the most polar solvent CH3CN. The PCM method applied to compound 4 supports these findings. In fact, it predicts the progressive increase of the eq/ax population ratio as the relative permittivity of the solvent increases. Moreover, it indicates that the computed νCO frequencies of the ax and eq conformers do not change in the non–polar solvents n-C6H14 and CCl4, while the νCO frequencies of the eq conformer become progressively lower than that of the ax one going from CHCl3 to CH2Cl2 and to CH3CN, in agreement with the experimental IR values. The analysis of the geometries of the ax and eq conformers shows that the carbonyl oxygen atom of the eq conformer is free for solvation, while the O[CO]H[o-Ph] hydrogen bond that takes place in the ax conformer partially hinders the approach of the solvent molecules to the carbonyl oxygen atom. Therefore, the larger solvation that occurs in the carbonyl oxygen atom of the eq conformer is responsible for the observed and calculated decrease of the corresponding frequency. The X-ray single crystal analysis of 2 indicates that this compound adopts the most polar eq geometry in the solid. In fact, in order to obtain the largest energy gain, the molecules are arranged in the crystal in a helical fashion due to dipole moment coupling along with C-HO and C-HπPh hydrogen bonds. Full article
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Open AccessArticle Facile and Efficient Syntheses of a Series of N-Benzyl and N-Biphenylmethyl Substituted Imidazole Derivatives Based on (E)-Urocanic acid, as Angiotensin II AT1 Receptor Blockers
Molecules 2013, 18(7), 7510-7532; doi:10.3390/molecules18077510
Received: 24 April 2013 / Revised: 17 June 2013 / Accepted: 20 June 2013 / Published: 27 June 2013
Cited by 1 | PDF Full-text (2087 KB) | HTML Full-text | XML Full-text
Abstract
In the present work, a facile and efficient route for the synthesis of a series of N-substituted imidazole derivatives is described. Docking studies have revealed that N-substituted imidazole derivatives based on (E)-urocanic acid may be potential antihypertensive leads. [...] Read more.
In the present work, a facile and efficient route for the synthesis of a series of N-substituted imidazole derivatives is described. Docking studies have revealed that N-substituted imidazole derivatives based on (E)-urocanic acid may be potential antihypertensive leads. Therefore, new AT1 receptor blockers bearing either the benzyl or the biphenylmethyl moiety at the N-1 or N-3 position, either the (E)-acrylate or the propanoate fragment and their related acids at the C-4 position as well as a halogen atom at the C-5 position of the imidazole ring, were synthesized. The newly synthesized analogues were evaluated for binding to human AT1 receptor. The biological results showed that this class of molecules possesses moderate or no activity, thus not always confirming high docking scores. Nonetheless, important conclusions can be derived for their molecular basis of their mode of action and help medicinal chemists to design and synthesize more potent ones. An aliphatic group as in losartan seems to be important for enhancing binding affinity and activity. Full article
(This article belongs to the Section Medicinal Chemistry)
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Open AccessArticle Synthesis, Surface Modification and Characterisation of Biocompatible Magnetic Iron Oxide Nanoparticles for Biomedical Applications
Molecules 2013, 18(7), 7533-7548; doi:10.3390/molecules18077533
Received: 24 April 2013 / Revised: 10 June 2013 / Accepted: 25 June 2013 / Published: 27 June 2013
Cited by 75 | PDF Full-text (1535 KB) | HTML Full-text | XML Full-text
Abstract
Superparamagnetic iron oxide nanoparticles (MNPs) with appropriate surface chemistry exhibit many interesting properties that can be exploited in a variety of biomedical applications such as magnetic resonance imaging contrast enhancement, tissue repair, hyperthermia, drug delivery and in cell separation. These applications required [...] Read more.
Superparamagnetic iron oxide nanoparticles (MNPs) with appropriate surface chemistry exhibit many interesting properties that can be exploited in a variety of biomedical applications such as magnetic resonance imaging contrast enhancement, tissue repair, hyperthermia, drug delivery and in cell separation. These applications required that the MNPs such as iron oxide Fe3O4 magnetic nanoparticles (Fe3O4 MNPs) having high magnetization values and particle size smaller than 100 nm. This paper reports the experimental detail for preparation of monodisperse oleic acid (OA)-coated Fe3O4 MNPs by chemical co-precipitation method to determine the optimum pH, initial temperature and stirring speed in order to obtain the MNPs with small particle size and size distribution that is needed for biomedical applications. The obtained nanoparticles were characterized by Fourier transform infrared spectroscopy (FTIR), transmission electron microscopy (TEM), scanning electron microscopy (SEM), energy dispersive X-ray fluorescence spectrometry (EDXRF), thermogravimetric analysis (TGA), X-ray powder diffraction (XRD), and vibrating sample magnetometer (VSM). The results show that the particle size as well as the magnetization of the MNPs was very much dependent on pH, initial temperature of Fe2+ and Fe3+ solutions and steering speed. The monodisperse Fe3O4 MNPs coated with oleic acid with size of 7.8 ± 1.9 nm were successfully prepared at optimum pH 11, initial temperature of 45 °C and at stirring rate of 800 rpm. FTIR and XRD data reveal that the oleic acid molecules were adsorbed on the magnetic nanoparticles by chemisorption. Analyses of TEM show the oleic acid provided the Fe3O4 particles with better dispersibility. The synthesized Fe3O4 nanoparticles exhibited superparamagnetic behavior and the saturation magnetization of the Fe3O4 nanoparticles increased with the particle size. Full article
Open AccessArticle Characterization of Total Phenolic Constituents from the Stems of Spatholobus suberectus Using LC-DAD-MSn and Their Inhibitory Effect on Human Neutrophil Elastase Activity
Molecules 2013, 18(7), 7549-7556; doi:10.3390/molecules18077549
Received: 3 June 2013 / Revised: 25 June 2013 / Accepted: 26 June 2013 / Published: 27 June 2013
Cited by 5 | PDF Full-text (205 KB) | HTML Full-text | XML Full-text
Abstract
Spatholobus suberectus Dunn, belonging to the legume family (Fabaceae), has been used as a Traditional Chinese Medicine for the treatment of anemia, menoxenia and rheumatism. A limited number of studies report that various types of flavonoids are the main characteristic constituents [...] Read more.
Spatholobus suberectus Dunn, belonging to the legume family (Fabaceae), has been used as a Traditional Chinese Medicine for the treatment of anemia, menoxenia and rheumatism. A limited number of studies report that various types of flavonoids are the main characteristic constituents of this herb. We have now found that S. suberectus contains about 2% phenolic components and characterized the major phenolic components as homogeneous B-type procyanidin conjugates using a liquid chromatography with diode-array detection-ESI mass spectrometry (LC-DAD/ESI-MS) method. This is the first report on occurrence of most B-type procyanidins in this herb. Moreover, the total phenolics extract was assayed for inhibitory activity on human neutrophil elastase and its IC50 was found to be 1.33 μg/mL. Full article
(This article belongs to the Section Natural Products)
Open AccessArticle New 7-[4-(4-(un)Substituted)piperazine-1-carbonyl]- piperazin-1-yl] Derivatives of Fluoroquinolone: Synthesis and Antimicrobial Evaluation
Molecules 2013, 18(7), 7557-7569; doi:10.3390/molecules18077557
Received: 5 June 2013 / Revised: 26 June 2013 / Accepted: 26 June 2013 / Published: 27 June 2013
Cited by 2 | PDF Full-text (265 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Fluoroquinolones have been a class of important synthetic antimicrobial agents broadly and effectively used in clinic for infectious diseases. In this study, the synthesis of a range of fluoroquinolone derivatives with 4-(carbopiperazin-1-yl)piperazinyl moieties at the C7 position and their inhibition of bacterial [...] Read more.
Fluoroquinolones have been a class of important synthetic antimicrobial agents broadly and effectively used in clinic for infectious diseases. In this study, the synthesis of a range of fluoroquinolone derivatives with 4-(carbopiperazin-1-yl)piperazinyl moieties at the C7 position and their inhibition of bacterial pathogens commonly disseminated in hospital environment were described. The results indicated that a 7-[4-(4-(benzoyl)carbopiperazin-1-yl)]piperazinyl derivative 5h and two 7-[4-(4- (benzenesulfonyl)carbopiperazin-1-yl)]piperazinyl derivatives 5k and 5l showed more promising growth inhibition of ciprofloxacin-resistant P. aeruginosa (CRPA) with MIC values as low as 16 mg/mL which is 16-fold more potent than ciprofloxacin, while most of other derivatives maintained potency against methicillin-resistant Staphylococcus aureus (MRSA). Full article
(This article belongs to the Section Medicinal Chemistry)
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Open AccessArticle Hepatotoxicity Evaluation of Aqueous Extract from Scutia buxifolia
Molecules 2013, 18(7), 7570-7583; doi:10.3390/molecules18077570
Received: 24 May 2013 / Revised: 16 June 2013 / Accepted: 17 June 2013 / Published: 28 June 2013
Cited by 6 | PDF Full-text (765 KB) | HTML Full-text | XML Full-text
Abstract
Nowadays there is an increase in the number of people taking herbals worldwide. Scutia buxifolia is used for the treatment of hypertension, but little is known about its action on liver. Thirty-two Wistar rats were divided into four groups: control and groups [...] Read more.
Nowadays there is an increase in the number of people taking herbals worldwide. Scutia buxifolia is used for the treatment of hypertension, but little is known about its action on liver. Thirty-two Wistar rats were divided into four groups: control and groups treated during 30 days with 100, 200 and 400 mg of lyophilized aqueous extract of S. buxifolia (SBSB)/kg of body weight. This study was planned to explore hepatotoxic effect of SBSB, which was assessed by serum transaminases (ALT and AST). Thiobarbituric acid reactive substances (TBARS) levels were determined in liver, along with thiols content (NPSH), catalase (CAT) activity and, superoxide dismutase (SOD) enzymes. Histopathological studies of liver tissue were performed. Flavonoids and phenolics were quantified in SBSB by high performance liquid chromatography with diode array detection (HPLC/DAD). We did not observe alterations on redox status (TBARS, NPSH, CAT and, SOD) in the control and experimental groups. An increase on AST activity was only observed at 200 mg of SBSB, whereas ALT score was not affected by SBSB. Moreover, no morphological alterations were observed on the hepatocytes, matching the analysed biochemical parameters. This way, we conclude that SBSB was not toxic. Full article
(This article belongs to the Section Natural Products)
Open AccessArticle Anxiolytic-Like and Antinociceptive Effects of 2(S)-Neoponcirin in Mice
Molecules 2013, 18(7), 7584-7599; doi:10.3390/molecules18077584
Received: 9 May 2013 / Revised: 12 June 2013 / Accepted: 19 June 2013 / Published: 28 June 2013
Cited by 3 | PDF Full-text (300 KB) | HTML Full-text | XML Full-text
Abstract
Study aims: 2(S)-neopincirin (NEO) is a constituent from of Clinopodium mexicanum, which is used in traditional Mexican herbal medicine for its tranquilizing and analgesic properties. This study investigated the anxiolytic-like, sedative and antinociceptive effects of NEO in several [...] Read more.
Study aims: 2(S)-neopincirin (NEO) is a constituent from of Clinopodium mexicanum, which is used in traditional Mexican herbal medicine for its tranquilizing and analgesic properties. This study investigated the anxiolytic-like, sedative and antinociceptive effects of NEO in several mice models. Material and methods: The anxiolytic-like effect was evaluated in the hole-board (HBT) and Open Field Tests (OFT); sedative effect was evaluated in sleeping time induced by sodium pentobarbital, and its antinociceptive actions were measured in the hot plate test. To evaluate if the GABA receptor could be involved in the anxiolytic-like effect produced by NEO, in independent experiments, the effects produced by co-administration of NEO plus muscimol (MUS) and NEO plus Pitrotoxin (PTX) were evaluated in the HBT. Results: NEO was isolated from Clinopodium mexicanum leaves. The NMR, MS and optic rotation data helped establish its identity as (2S)-5-hydroxy-4′-methoxyflavanone-7-O-{β-glucopyranosyl-(1→6)-β-rhamnoside}. NEO showed an anxiolytic-like effect and was able to counter the nociception induced by a thermal stimulus in a dose-dependent manner. PTX blocked the anxiolytic-like effect of NEO, while MUS was able to enhance it. Conclusions: The findings of present work demonstrated that NEO possesses anxiolytic-like and antinociceptive effects in mice. Such effects are not associated with changes in the locomotor activity. These results supported the notion that anxiolytic-like effect of NEO involves the participation of GABAergic system. Full article
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Open AccessArticle Isolation and Synthesis of a Bioactive Benzenoid Derivative from the Fruiting Bodies of Antrodia camphorata
Molecules 2013, 18(7), 7600-7608; doi:10.3390/molecules18077600
Received: 15 May 2013 / Revised: 20 June 2013 / Accepted: 21 June 2013 / Published: 28 June 2013
Cited by 3 | PDF Full-text (389 KB) | HTML Full-text | XML Full-text
Abstract
A new enynyl-benzenoid, antrocamphin O (1,4,7-dimethoxy-5-methyl-6-(3′-methylbut-3-en-1-ynyl)benzo[d][1,3]dioxide), and the known benzenoids antrocamphin A and 7-dimethoxy-5-methyl-1,3-benzodioxole, were isolated from the fruiting bodies of Antrodia camphorata (Taiwanofungus camphoratus). The structure of antrocamphin O was unambiguously assigned by the analysis of spectral data (including [...] Read more.
A new enynyl-benzenoid, antrocamphin O (1,4,7-dimethoxy-5-methyl-6-(3′-methylbut-3-en-1-ynyl)benzo[d][1,3]dioxide), and the known benzenoids antrocamphin A and 7-dimethoxy-5-methyl-1,3-benzodioxole, were isolated from the fruiting bodies of Antrodia camphorata (Taiwanofungus camphoratus). The structure of antrocamphin O was unambiguously assigned by the analysis of spectral data (including 1D and 2D NMR, high-resolution MS, IR, and UV) and total synthesis. Compound 1 was prepared through the Sonogashira reaction of 5-iodo-4,7-dimethoxy-6-methylbenzene and 2-methylbut-1-en-3-yne as the key step. The benzenoids were tested for cytotoxicity against the HT29, HTC15, DLD-1, and COLO 205 colon cancer cell lines, and activities are reported herein. Full article
Open AccessArticle Synthesis and Characterization of Some New Complexes of Magnesium (II) and Zinc (II) with the Natural Flavonoid Primuletin
Molecules 2013, 18(7), 7631-7645; doi:10.3390/molecules18077631
Received: 20 May 2013 / Revised: 17 June 2013 / Accepted: 19 June 2013 / Published: 1 July 2013
Cited by 6 | PDF Full-text (799 KB) | HTML Full-text | XML Full-text
Abstract
Two new metal complexes formulated as [Mg(L)2(H2O)2]·H2O (1) and [Zn(L)2(H2O)2]·0.5H2O (2), where HL = 5-hydroxyflavone (primuletin), have been synthesized and characterized by elemental and thermal analyses, [...] Read more.
Two new metal complexes formulated as [Mg(L)2(H2O)2]·H2O (1) and [Zn(L)2(H2O)2]·0.5H2O (2), where HL = 5-hydroxyflavone (primuletin), have been synthesized and characterized by elemental and thermal analyses, molar conductance, IR, UV-Vis, 1H- and 13C-NMR, fluorescence and mass spectra. In solid state, complexes had shown higher fluorescence intensities comparing to the free ligand, and this behavior is appreciated as a consequence of the coordination process. Full article
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Open AccessArticle Eco-Friendly Chitosan Production by Syncephalastrum racemosum and Application to the Removal of Acid Orange 7 (AO7) from Wastewaters
Molecules 2013, 18(7), 7646-7660; doi:10.3390/molecules18077646
Received: 19 March 2013 / Revised: 2 May 2013 / Accepted: 25 June 2013 / Published: 1 July 2013
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Abstract
Due to the existence of new methodologies that have reduced the production costs of microbiological chitosan, this paper puts forward the use of agro-industrial residues in order to produce microbiological chitosan and to apply chitosan as an innovative resource for removing acid [...] Read more.
Due to the existence of new methodologies that have reduced the production costs of microbiological chitosan, this paper puts forward the use of agro-industrial residues in order to produce microbiological chitosan and to apply chitosan as an innovative resource for removing acid orange 7 (AO7) from wastewaters. The best culture conditions were selected by a full 24 factorial design, and the removal of the dye was optimized by a 23 central composite rotational design. The results showed that corn steep liquor (CSL) is an agro-industrial residue that can be advantageously used to produce microbiological chitosan with yields up to 7.8 g/kg of substrate. FT-IR spectra of the product showed typical peak distributions like those of standard chitosan which confirmed the extracted product was chitosan-like. The efficiency of removing low concentrations of AO7 by using microbiological chitosan in distilled water (up to 89.96%) and tap water (up to 80.60%) was significantly higher than the efficiency of the control (chitosan obtained from crustaceans), suggesting that this biopolymer is a better economic alternative for discoloring wastewater where a low concentration of the dye is considered toxic. The high percentage recovery of AO7 from the microbiological chitosan particles used favors this biopolymer as a possible bleaching agent which may be reusable. Full article
(This article belongs to the Section Natural Products)
Open AccessArticle 1,2,3-Triazole-Substituted Oleanolic Acid Derivatives: Synthesis and Antiproliferative Activity
Molecules 2013, 18(7), 7661-7674; doi:10.3390/molecules18077661
Received: 30 May 2013 / Revised: 26 June 2013 / Accepted: 27 June 2013 / Published: 1 July 2013
Cited by 16 | PDF Full-text (251 KB) | HTML Full-text | XML Full-text
Abstract
Hybrid compounds are relevant products when searching for structure-activity relationships of natural products. Starting from the naturally occurring triterpene oleanolic acid, alkyl esters were prepared and treated with different aromatic azides using click chemistry to produce hybrid compounds. Some 18 new oleanolic [...] Read more.
Hybrid compounds are relevant products when searching for structure-activity relationships of natural products. Starting from the naturally occurring triterpene oleanolic acid, alkyl esters were prepared and treated with different aromatic azides using click chemistry to produce hybrid compounds. Some 18 new oleanolic acid derivatives were synthesized and the structures were confirmed by spectroscopic and spectrometric means. The antiproliferative activity of the new derivatives was evaluated towards normal lung fibroblasts (MRC-5), gastric epithelial adenocarcinoma (AGS), promyelocytic leukemia (HL-60), lung cancer (SK-MES-1) and bladder carcinoma (J82) cells. The alkyne esters 1 and 3 showed activity on all cell lines but without selectivity (19.6–23.1 μM and 14.1–56.2 μM, respectively), their respective methyl esters were inactive. Compounds with a benzene and p-anisole attached to the triazole ring, showed no antiproliferative effect. Introduction of a chlorine atom into the benzene ring (compound 9) elicited a selective effect against AGS cells (IC50 value: 8.9 μM). The activity was lost when the COOH function at C-28 was methylated. Better antiproliferative effect was found for compounds 11 and 15 bearing a p-toluenesulphonyl group, with values in the range of 10.8–47.1 μM and 11.5–22.2 μM, respectively. The effect, however, was not associated with selectivity. Full article
(This article belongs to the Section Natural Products)
Open AccessCommunication Efficient One-Pot Synthesis of 5-Chloromethylfurfural (CMF) from Carbohydrates in Mild Biphasic Systems
Molecules 2013, 18(7), 7675-7685; doi:10.3390/molecules18077675
Received: 22 May 2013 / Revised: 24 June 2013 / Accepted: 25 June 2013 / Published: 2 July 2013
Cited by 9 | PDF Full-text (207 KB) | HTML Full-text | XML Full-text | Correction | Supplementary Files
Abstract
5-Halomethylfurfurals can be considered as platform chemicals of high reactivity making them useful for the preparation of a variety of important compounds. In this study, a one-pot route for the conversion of carbohydrates into 5-chloromethylfurfural (CMF) in a simple and efficient (HCl-H [...] Read more.
5-Halomethylfurfurals can be considered as platform chemicals of high reactivity making them useful for the preparation of a variety of important compounds. In this study, a one-pot route for the conversion of carbohydrates into 5-chloromethylfurfural (CMF) in a simple and efficient (HCl-H3PO4/CHCl3) biphasic system has been investigated. Monosaccharides such as D-fructose, D-glucose and sorbose, disaccharides such as sucrose and cellobiose and polysaccharides such as cellulose were successfully converted into CMF in satisfactory yields under mild conditions. Our data shows that when using D-fructose the optimum yield of CMF was about 47%. This understanding allowed us to extent our work to biomaterials, such as wood powder and wood pulps with yields of CMF obtained being comparable to those seen with some of the enumerated mono and disaccharides. Overall, the proposed (HCl-H3PO4/CHCl3) optimized biphasic system provides a simple, mild, and cost-effective means to prepare CMF from renewable resources. Full article
(This article belongs to the Special Issue Heterogeneous Catalysis)
Open AccessArticle Biosynthesis of Panaxynol and Panaxydol in Panax ginseng
Molecules 2013, 18(7), 7686-7698; doi:10.3390/molecules18077686
Received: 6 May 2013 / Revised: 13 June 2013 / Accepted: 28 June 2013 / Published: 2 July 2013
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Abstract
The natural formation of the bioactive C17-polyacetylenes (−)-(R)-panaxynol and panaxydol was analyzed by 13C-labeling experiments. For this purpose, plants of Panax ginseng were supplied with 13CO2 under field conditions or, alternatively, sterile root cultures of [...] Read more.
The natural formation of the bioactive C17-polyacetylenes (−)-(R)-panaxynol and panaxydol was analyzed by 13C-labeling experiments. For this purpose, plants of Panax ginseng were supplied with 13CO2 under field conditions or, alternatively, sterile root cultures of P. ginseng were supplemented with [U-13C6]glucose. The polyynes were isolated from the labeled roots or hairy root cultures, respectively, and analyzed by quantitative NMR spectroscopy. The same mixtures of eight doubly 13C-labeled isotopologues and one single labeled isotopologue were observed in the C17-polyacetylenes obtained from the two experiments. The polyketide-type labeling pattern is in line with the biosynthetic origin of the compounds via decarboxylation of fatty acids, probably of crepenynic acid. The 13C-study now provides experimental evidence for the biosynthesis of panaxynol and related polyacetylenes in P. ginseng under in planta conditions as well as in root cultures. The data also show that 13CO2 experiments under field conditions are useful to elucidate the biosynthetic pathways of metabolites, including those from roots. Full article
(This article belongs to the Special Issue Phytochemicals: Analytical and Medicinal Chemistry)
Open AccessArticle Protection of Astaxanthin in Astaxanthin Nanodispersions Using Additional Antioxidants
Molecules 2013, 18(7), 7699-7710; doi:10.3390/molecules18077699
Received: 2 May 2013 / Revised: 21 June 2013 / Accepted: 1 July 2013 / Published: 2 July 2013
Cited by 5 | PDF Full-text (238 KB) | HTML Full-text | XML Full-text
Abstract
The protective effects of α-tocopherol and ascorbic acid on astaxanthin in astaxanthin nanodispersions produced via a solvent-diffusion technique and stabilized by a three-component stabilizer system, were studied either individually or in combination by using response surface methodology. Generally, both α-tocopherol and ascorbic [...] Read more.
The protective effects of α-tocopherol and ascorbic acid on astaxanthin in astaxanthin nanodispersions produced via a solvent-diffusion technique and stabilized by a three-component stabilizer system, were studied either individually or in combination by using response surface methodology. Generally, both α-tocopherol and ascorbic acid could retard the astaxanthin degradation in astaxanthin nanodispersions. The results showed that the using α-tocopherol and ascorbic acid can be more efficient in increasing the chemical stability of nanodispersions in comparison to using them individually. Using a response surface methodology (RSM) response optimizer, it was seen that addition of ascorbic acid (ascorbic acid/astaxanthin w/w) and α-tocopherol (α-tocopherol/astaxanthin w/w) in proportions of 0.4 and 0.6, respectively, would give the maximum chemical stability to the studied astaxanthin nanodispersions. Full article
Open AccessArticle Analytical Study for the Charge-Transfer Complexes of Rosuvastatin Calcium with π-Acceptors
Molecules 2013, 18(7), 7711-7725; doi:10.3390/molecules18077711
Received: 31 May 2013 / Revised: 18 June 2013 / Accepted: 21 June 2013 / Published: 3 July 2013
Cited by 3 | PDF Full-text (329 KB) | HTML Full-text | XML Full-text
Abstract
Studies were carried out to investigate the charge-transfer (CT) reaction of ROS-Ca, as a n-electron donor with various p-acceptors: tetracyanoethylene, p-chloranilic acid, 2,3-dichloro-5,6-dicyano-1,4-benzoquinone, 2,3,5,6-tetrabromo-1,4-benzoquinone, 1,3,5-trinitrobenzene, 2,3,5,6-tetrachloro-1,4-benzoquinone, 7,7,8,8-tetracyano-quinodimethane, and 2,4,7-trinitro-9-fluorenone. Different colored CT complexes were obtained. The reaction mechanism and site of [...] Read more.
Studies were carried out to investigate the charge-transfer (CT) reaction of ROS-Ca, as a n-electron donor with various p-acceptors: tetracyanoethylene, p-chloranilic acid, 2,3-dichloro-5,6-dicyano-1,4-benzoquinone, 2,3,5,6-tetrabromo-1,4-benzoquinone, 1,3,5-trinitrobenzene, 2,3,5,6-tetrachloro-1,4-benzoquinone, 7,7,8,8-tetracyano-quinodimethane, and 2,4,7-trinitro-9-fluorenone. Different colored CT complexes were obtained. The reaction mechanism and site of interaction were determined by ultraviolet-visible spectrophotometric techniques and computational molecular modeling. The formation of the colored complexes was utilized in the development of simple, rapid and accurate spectrophotometric methods for the determination of ROS-Ca. Under the optimum reaction conditions, linear relationships with good correlation coefficients (0.9984–0.9995) were found between the absorbances and the concentrations of ROS-Ca in the range of 2–200 mg mL−1. The limits of detection ranged from 0.41 to 12.24 mg mL−1. No interference could be observed from the additives commonly present in the tablets or from the drugs that are co-formulated with ROS-Ca in its combined formulations. The methods were successfully applied to the analysis of tablets with good accuracy and precision; the recovery percentages ranged from 99.54–100.46 ± 1.58–1.82%. The results were compared favorably with the reported method. The proposed methods are practical and valuable for routine application in quality control laboratories for determination of ROS-Ca in its bulk form and tablets. Full article
Open AccessArticle Benchmark Study on the Smallest Bimolecular Nucleophilic Substitution Reaction: H−+CH4 →CH4+H
Molecules 2013, 18(7), 7726-7738; doi:10.3390/molecules18077726
Received: 20 May 2013 / Revised: 3 June 2013 / Accepted: 28 June 2013 / Published: 3 July 2013
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Abstract
We report here a benchmark study on the bimolecular nucleophilic substitution (SN2) reaction between hydride and methane, for which we have obtained reference energies at the coupled cluster toward full configuration-interaction limit (CC-cf/CBS). Several wavefunction (HF, MP2, coupled cluster) and [...] Read more.
We report here a benchmark study on the bimolecular nucleophilic substitution (SN2) reaction between hydride and methane, for which we have obtained reference energies at the coupled cluster toward full configuration-interaction limit (CC-cf/CBS). Several wavefunction (HF, MP2, coupled cluster) and density functional methods are compared for their reliability regarding these reference data. Full article
(This article belongs to the Special Issue Electrophilic & Nucleophilic Substitution)
Open AccessArticle Studies on the Alkaloids of the Bark of Magnolia officinalis: Isolation and On-line Analysis by HPLC-ESI-MSn
Molecules 2013, 18(7), 7739-7750; doi:10.3390/molecules18077739
Received: 31 May 2013 / Revised: 13 June 2013 / Accepted: 27 June 2013 / Published: 3 July 2013
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Abstract
The bark of Magnolia officinalis is a well-known Traditional Chinese Medicine. In the present study, two new alkaloids, named (S)-4-keto-magnoflorine (6) and (R)-3,4-dehydromagnocurarine (11), together with seven known alkaloids: (S)-magnoflorine (5 [...] Read more.
The bark of Magnolia officinalis is a well-known Traditional Chinese Medicine. In the present study, two new alkaloids, named (S)-4-keto-magnoflorine (6) and (R)-3,4-dehydromagnocurarine (11), together with seven known alkaloids: (S)-magnoflorine (5), trans/cis N-feruloylputrescine (7/8), (R)-magnocurarine (10), (S)-tembetarine (12), (R)-oblongine (14), and (R)-asimilobine (17) were isolated and their structures elucidated by spectroscopic methods, including 1D, 2D NMR, and HRESI-MS. The absolute configurations of the isoquinoline alkaloids 5, 6, 1012, 14, and 17 were determined by CD. In vitro inhibitory activities against aldose reductase, lipase, α-glucosidase, DPP–IV and three cancer cell lines (A549, Bel-7402, and HCT-8) were evaluated for all isolated compounds. However, all compounds showed weak activities in all tests at the same concentration as the positive control drugs. An HPLC-ESI-MSn method has been established for screening of alkaloids in the bark of M. officinalis. A total of 23 alkaloids were identified or tentatively characterized; including 13 aporphines, eight benzylisoquinolines and two amides. Plausible fragmentation pathways of the representative compounds 6, 7/8, 11, and 17 were proposed in the present study. Full article
(This article belongs to the Section Natural Products)
Open AccessArticle Two New Phenolic Glycosides from Gnaphalium affine D. Don and Their Anti-Complementary Activity
Molecules 2013, 18(7), 7751-7760; doi:10.3390/molecules18077751
Received: 20 May 2013 / Revised: 25 June 2013 / Accepted: 25 June 2013 / Published: 3 July 2013
Cited by 4 | PDF Full-text (369 KB) | HTML Full-text | XML Full-text
Abstract
Two new phenolic glycosides, named gnaphaffine A and B (compounds 1 and 2), were isolated from Gnaphalium affine. together with six known compounds, including caffeic acid (3), everlastoside L (4), isorhamnetin-7-O-β-D-glucopyranoside (5), [...] Read more.
Two new phenolic glycosides, named gnaphaffine A and B (compounds 1 and 2), were isolated from Gnaphalium affine. together with six known compounds, including caffeic acid (3), everlastoside L (4), isorhamnetin-7-O-β-D-glucopyranoside (5), quercetin- 3-O-β-D-glucopyranoside (6), scutellarein-7-O-β-D-glucoside (7) and api-genin-7-O-β-D- glucopyranoside (8). Their structures were elucidated by spectroscopic methods, including ESI-MS and 2D NMR spectroscopy (HMQC and HMBC). All compounds were evaluated for their anti-complementary activity on the classical pathway of the complement system in vitro. Full article
Open AccessArticle In-silico Leishmania Target Selectivity of Antiparasitic Terpenoids
Molecules 2013, 18(7), 7761-7847; doi:10.3390/molecules18077761
Received: 20 May 2013 / Revised: 23 June 2013 / Accepted: 26 June 2013 / Published: 3 July 2013
Cited by 7 | PDF Full-text (1179 KB) | HTML Full-text | XML Full-text
Abstract
Neglected Tropical Diseases (NTDs), like leishmaniasis, are major causes of mortality in resource-limited countries. The mortality associated with these diseases is largely due to fragile healthcare systems, lack of access to medicines, and resistance by the parasites to the few available drugs. [...] Read more.
Neglected Tropical Diseases (NTDs), like leishmaniasis, are major causes of mortality in resource-limited countries. The mortality associated with these diseases is largely due to fragile healthcare systems, lack of access to medicines, and resistance by the parasites to the few available drugs. Many antiparasitic plant-derived isoprenoids have been reported, and many of them have good in vitro activity against various forms of Leishmania spp. In this work, potential Leishmania biochemical targets of antiparasitic isoprenoids were studied in silico. Antiparasitic monoterpenoids selectively docked to L. infantum nicotinamidase, L. major uridine diphosphate-glucose pyrophosphorylase and methionyl t-RNA synthetase. The two protein targets selectively targeted by germacranolide sesquiterpenoids were L. major methionyl t-RNA synthetase and dihydroorotate dehydrogenase. Diterpenoids generally favored docking to L. mexicana glycerol-3-phosphate dehydrogenase. Limonoids also showed some selectivity for L. mexicana glycerol-3-phosphate dehydrogenase and L. major dihydroorotate dehydrogenase while withanolides docked more selectively with L. major uridine diphosphate-glucose pyrophosphorylase. The selectivity of the different classes of antiparasitic compounds for the protein targets considered in this work can be explored in fragment- and/or structure-based drug design towards the development of leads for new antileishmanial drugs. Full article
(This article belongs to the Special Issue Plant Natural Products against Human Parasites)
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Open AccessArticle Characterization of Protein and Peptide Binding to Nanogels Formed by Differently Charged Chitosan Derivatives
Molecules 2013, 18(7), 7848-7864; doi:10.3390/molecules18077848
Received: 25 April 2013 / Revised: 17 June 2013 / Accepted: 26 June 2013 / Published: 3 July 2013
Cited by 10 | PDF Full-text (1960 KB) | HTML Full-text | XML Full-text
Abstract
Chitosan (Chi) is a natural biodegradable cationic polymer with remarkable potency as a vehicle for drug or vaccine delivery. Chi possesses multiple groups, which can be used both for Chi derivatization and for particle formation. The aim of this work was to [...] Read more.
Chitosan (Chi) is a natural biodegradable cationic polymer with remarkable potency as a vehicle for drug or vaccine delivery. Chi possesses multiple groups, which can be used both for Chi derivatization and for particle formation. The aim of this work was to produce stable nanosized range Chi gels (nanogels, NGs) with different charge and to study the driving forces of complex formation between Chi NGs and proteins or peptides. Positively charged NGs of 150 nm in diameter were prepared from hexanoyl chitosan (HC) by the ionotropic gelation method while negatively charged NGs of 190 nm were obtained from succinoyl Chi (SC) by a Ca2+ coacervation approach. NGs were loaded with a panel of proteins or peptides with different weights and charges. We show that NGs preferentially formed complexes with oppositely charged molecules, especially peptides, as was demonstrated by gel-electrophoresis, confocal microscopy and HPLC. Complex formation was accompanied by a change in zeta-potential and decrease in size. We concluded that complex formation between Chi NGs and peptide/proteins is mediated mostly by electrostatic interactions. Full article
(This article belongs to the Special Issue Chitins and Chitosans)
Open AccessArticle In Vitro Antimicrobial Activity of Plant-Derived Diterpenes against Bovine Mastitis Bacteria
Molecules 2013, 18(7), 7865-7872; doi:10.3390/molecules18077865
Received: 27 May 2013 / Revised: 20 June 2013 / Accepted: 21 June 2013 / Published: 4 July 2013
Cited by 4 | PDF Full-text (214 KB) | HTML Full-text | XML Full-text
Abstract
We evaluated the antibacterial activity of three diterpenes isolated from natural sources against a panel of microorganisms responsible for bovine mastitis. ent-Copalic acid (CA) was the most active metabolite, with promising MIC values (from 1.56 to 6.25 µg mL−1) [...] Read more.
We evaluated the antibacterial activity of three diterpenes isolated from natural sources against a panel of microorganisms responsible for bovine mastitis. ent-Copalic acid (CA) was the most active metabolite, with promising MIC values (from 1.56 to 6.25 µg mL−1) against Staphylococcus aureus (ATCC and clinical isolate), Staphylococcus epidermidis, Streptococcus agalactiae, and Streptococcus dysgalactiae. We conducted time-kill assays of CA against S. aureus, a commensal organism considered to be a ubiquitous etiological agent of bovine mastitis in dairy farms worldwide. In the first 12 h, CA only inhibited the growth of the inoculums (bacteriostatic effect), but its bactericidal effect was clearly noted thereafter (between 12 and 24 h). In conclusion, CA should be considered for the control of several Gram-positive bacteria related to bovine mastitis. Full article
(This article belongs to the Section Natural Products)
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Open AccessArticle Comprehensive Theoretical Studies on the Reaction of 1-Bromo-3,3,3-trifluoropropene with OH Free Radicals
Molecules 2013, 18(7), 7873-7885; doi:10.3390/molecules18077873
Received: 16 May 2013 / Revised: 18 June 2013 / Accepted: 20 June 2013 / Published: 4 July 2013
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Abstract
The potential energy surfaces (PES) for the reaction of 1-bromo-3,3,3-trifluoropropene (CF3CHCBrH) with hydroxyl (OH) free radicals is probed theoretically at the CCSD/aug-cc-pVDZ//B3LYP/6-311++G(d,p) level of theory. All the possible stationary and first-order saddle points along the reaction paths were verified by [...] Read more.
The potential energy surfaces (PES) for the reaction of 1-bromo-3,3,3-trifluoropropene (CF3CHCBrH) with hydroxyl (OH) free radicals is probed theoretically at the CCSD/aug-cc-pVDZ//B3LYP/6-311++G(d,p) level of theory. All the possible stationary and first-order saddle points along the reaction paths were verified by the vibrational analysis. The calculations account for all the product channels. Based on the calculated CCSD/aug-cc-pVDZ potential energy surface, the possible reaction mechanism is discussed. Six distinct reaction pathways of 1-bromo-3,3,3-trifluoropropene (BTP) with OH are investigated. The geometries, reaction enthalpies and energy barriers are determined. Canonical transition-state theory with Wigner tunneling correction was used to predict the rate constants for the temperature range of 290–3,000 K without any artificial adjustment, and the computed rate constants for elementary channels can be accurately fitted with three-parameter Arrhenius expressions. OH addition reaction channel and the H atom abstraction channels related to the carbon-carbon double bond are found to be the main reaction channels for the reaction of 1-bromo-3,3,3-trifluoropropene (CF3CHCBrH) with hydroxyl (OH) free radicals while the products leading to CF3CHCH + BrOH and COHF2CHCBrH + F play a negligible role. Full article
(This article belongs to the Special Issue Computational Chemistry)
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Open AccessArticle Abscisic Acid Induced Changes in Production of Primary and Secondary Metabolites, Photosynthetic Capacity, Antioxidant Capability, Antioxidant Enzymes and Lipoxygenase Inhibitory Activity of Orthosiphon stamineus Benth.
Molecules 2013, 18(7), 7957-7976; doi:10.3390/molecules18077957
Received: 6 June 2013 / Revised: 3 July 2013 / Accepted: 3 July 2013 / Published: 5 July 2013
Cited by 10 | PDF Full-text (256 KB) | HTML Full-text | XML Full-text
Abstract
An experiment was conducted to investigate and distinguish the relationships in the production of total phenolics, total flavonoids, soluble sugars, H2O2, O2, phenylalanine ammonia lyase (PAL) activity, leaf gas exchange, antioxidant activity, antioxidant enzyme activity [...] Read more.
An experiment was conducted to investigate and distinguish the relationships in the production of total phenolics, total flavonoids, soluble sugars, H2O2, O2, phenylalanine ammonia lyase (PAL) activity, leaf gas exchange, antioxidant activity, antioxidant enzyme activity [ascorbate peroxidase (APX), catalase (CAT), superoxide dismutase (SOD) and Lipoxygenase inhibitory activity (LOX)] under four levels of foliar abscisic acid (ABA) application (0, 2, 4, 6 µM) for 15 weeks in Orthosiphon stamineus Benth. It was found that the production of plant secondary metabolites, soluble sugars, antioxidant activity, PAL activity and LOX inhibitory activity was influenced by foliar application of ABA. As the concentration of ABA was increased from 0 to 6 µM the production of total phenolics, flavonoids, sucrose, H2O2, O2, PAL activity and LOX inhibitory activity was enhanced. It was also observed that the antioxidant capabilities (DPPH and ORAC) were increased. This was followed by increases in production of antioxidant enzymes APX, CAT and SOD. Under high application rates of ABA the net photosynthesis and stomatal conductance was found to be reduced. The production of primary and secondary metabolites displayed a significant positive relationship with H2O2 (total phenolics, r2 = 0.877; total flavonoids, r2 = 0.812; p ≤ 0.05) and O2 (total phenolics, r2 = 0.778; total flavonoids, r2 = 0.912; p ≤ 0.05). This indicated that increased oxidative stress at high application rates of ABA, improved the production of phytochemicals. Full article
Open AccessArticle Antibacterial and Herbicidal Activity of Ring-Substituted 3-Hydroxynaphthalene-2-carboxanilides
Molecules 2013, 18(7), 7977-7997; doi:10.3390/molecules18077977
Received: 23 May 2013 / Revised: 17 June 2013 / Accepted: 4 July 2013 / Published: 8 July 2013
Cited by 13 | PDF Full-text (314 KB) | HTML Full-text | XML Full-text
Abstract
In this study, a series of twenty-two ring-substituted 3-hydroxy-N-phenylnaphthalene-2-carboxanilides were prepared and characterized. The compounds were tested for their activity related to inhibition of photosynthetic electron transport (PET) in spinach (Spinacia oleracea L.) chloroplasts. Primary in vitro screening of [...] Read more.
In this study, a series of twenty-two ring-substituted 3-hydroxy-N-phenylnaphthalene-2-carboxanilides were prepared and characterized. The compounds were tested for their activity related to inhibition of photosynthetic electron transport (PET) in spinach (Spinacia oleracea L.) chloroplasts. Primary in vitro screening of the synthesized compounds was also performed against four Staphylococcus strains and against two mycobacterial species. 3-Hydroxy-N-(2-methoxyphenyl)naphthalene-2-carboxamide showed high biological activity (MIC = 55.0 µmol/L) against S. aureus as well as methicillin-resistant strains. N-(2-Fluorophenyl)-3-hydroxynaphthalene-2-carboxamide showed higher activity (MIC = 28.4 µmol/L) against M. marinum than the standard isoniazid and 3-hydroxy-N-(4-nitrophenyl)naphthalene-2-carboxamide expressed higher activity (MIC = 13.0 µmol/L) against M. kansasii than the standard isoniazid. Cytotoxicity assay of effective antimicrobial compounds was performed using the human monocytic leukemia THP-1 cell line. The PET-inhibiting activity expressed by IC50 value of the most active compound 3-hydroxy-N-(3-nitrophenyl)naphthalene-2-carboxamide was 16.9 μmol/L. The structure-activity relationships of all compounds are discussed. Full article
(This article belongs to the Section Medicinal Chemistry)
Open AccessCommunication Preventive Effects of Eleutherococcus senticosus Bark Extract in OVX-Induced Osteoporosis in Rats
Molecules 2013, 18(7), 7998-8008; doi:10.3390/molecules18077998
Received: 13 June 2013 / Revised: 3 July 2013 / Accepted: 3 July 2013 / Published: 8 July 2013
Cited by 3 | PDF Full-text (305 KB) | HTML Full-text | XML Full-text
Abstract
Eleutherococcus senticosus (Siberian ginseng), has been used as a powerful tonic herb with an impressive range of health benefits. This medicinal herb has been commonly used to treat bone metabolism diseases due to its traditional Korean medicine use to strengthen muscle and [...] Read more.
Eleutherococcus senticosus (Siberian ginseng), has been used as a powerful tonic herb with an impressive range of health benefits. This medicinal herb has been commonly used to treat bone metabolism diseases due to its traditional Korean medicine use to strengthen muscle and bone. This study was conducted to investigate prevention of bone loss by a standardized extract of dried E. senticosus stem bark in an ovariectomized (OVX) rat model of osteoporosis. The OVX groups were divided into five groups treated with distilled water, 17β-estradiol (E2 10 μg/kg, once daily, i.p) and dried stem bark of E. senticosus extracts (DES 10, 30, and 100 mg/kg, once daily, p.o) for eight weeks, respectively. After eight weeks of treatments, the femur bone mineral density of the 100 mg/kg DES-treated group was significantly higher than that of the OVX-control group (16.7%, p < 0.01) without affecting the body, organs, and uterus weights, and serum estradiol levels. Additionally, bone markers such as serum ALP, CTx, and OC levels were significantly decreased in the DES 100 mg/kg treated group. These results show that DES is able to prevent OVX-induced in bone loss without the influence of hormones such as estrogen. Full article
(This article belongs to the Section Natural Products)
Open AccessArticle Antiplasmodial Alkaloids from the Bark of Cryptocarya nigra (Lauraceae)
Molecules 2013, 18(7), 8009-8017; doi:10.3390/molecules18078009
Received: 29 May 2013 / Revised: 30 June 2013 / Accepted: 2 July 2013 / Published: 8 July 2013
Cited by 9 | PDF Full-text (209 KB) | HTML Full-text | XML Full-text
Abstract
A dichloromethane extract of the stem bark of Cryptocarya nigra showed strong in vitro inhibition of Plasmodium falciparum growth, with an IC50 value of 2.82 μg/mL. The phytochemical study of this extract has led to the isolation and characterization of four [...] Read more.
A dichloromethane extract of the stem bark of Cryptocarya nigra showed strong in vitro inhibition of Plasmodium falciparum growth, with an IC50 value of 2.82 μg/mL. The phytochemical study of this extract has led to the isolation and characterization of four known alkaloids: (+)-N-methylisococlaurine (1), atherosperminine (2), 2-hydroxyathersperminine (3), and noratherosperminine (4). Structural elucidation of all alkaloids was accomplished by means of high field 1D- and 2D-NMR, IR, UV and LCMS spectral data. The isolated extract constituents (+)-N-methylisococlaurine (1), atherosperminine (2) and 2-hydroxy-atherosperminine (3) showed strong antiplasmodial activity, with IC50 values of 5.40, 5.80 and 0.75 μM, respectively. In addition, (+)-N-methylisocolaurine (1) and atherosperminine (2) showed high antioxidant activity in a DPPH assay with IC50 values of 29.56 ug/mL and 54.53 ug/mL respectively. Compounds 1 and 2 also both showed high antioxidant activity in the FRAP assay, with percentages of 78.54 and 70.66 respectively and in the metal chelating assay, with IC50 values of 50.08 ug/mL and 42.87 ug/mL, respectively. Full article
(This article belongs to the Section Natural Products)
Open AccessArticle Synthesis and Preliminary Biological Evaluations of 5′-Substituted Derivatives of Uridine as Glycosyltransferase Inhibitors
Molecules 2013, 18(7), 8018-8027; doi:10.3390/molecules18078018
Received: 2 May 2013 / Accepted: 26 June 2013 / Published: 8 July 2013
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Abstract
New derivatives of uridine which contain a b-ketoenol motif were synthesized, characterized and biologically tested. Synthesized compounds 14 showed no activity against bovine milk β-1,4-galactosyltransferase I at concentrations up to 2.0 mM and were not active against Candida albicans and [...] Read more.
New derivatives of uridine which contain a b-ketoenol motif were synthesized, characterized and biologically tested. Synthesized compounds 14 showed no activity against bovine milk β-1,4-galactosyltransferase I at concentrations up to 2.0 mM and were not active against Candida albicans and Aspergilus fumigatus up to the maximum tested concentration of 1,000 µg/mL. Full article
(This article belongs to the Section Organic Synthesis)
Open AccessArticle Mechanistic Studies on Regioselective Dephosphorylation of Phosphate Prodrugs during a Facile Synthesis of Antitumor Phosphorylated 2-Phenyl-6,7-methylenedioxy-1H-quinolin-4-one
Molecules 2013, 18(7), 8028-8045; doi:10.3390/molecules18078028
Received: 13 May 2013 / Revised: 5 June 2013 / Accepted: 1 July 2013 / Published: 8 July 2013
PDF Full-text (607 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Phosphorylation of 2-(3-hydroxy-5-methoxyphenyl)-6,7-methylenedioxy-1H-quinolin-4-one (1) afforded diphosphate 2. We found that, upon treatment with methanol under mild conditions, 2 can undergo facile and highly regioselective dephosphorylation to give the monophosphate 3, with a phosphate group remaining on [...] Read more.
Phosphorylation of 2-(3-hydroxy-5-methoxyphenyl)-6,7-methylenedioxy-1H-quinolin-4-one (1) afforded diphosphate 2. We found that, upon treatment with methanol under mild conditions, 2 can undergo facile and highly regioselective dephosphorylation to give the monophosphate 3, with a phosphate group remaining on the phenyl ring. The details of the dephosphorylation process were postulated and then probed by LC-MS and HPLC analyses. Furthermore, as a preliminary study, the water soluble monophosphate prodrug 4 was tested for antitumor activity against a MCF-7 xenograft nude mice model. Full article
(This article belongs to the Section Medicinal Chemistry)
Open AccessArticle Synthesis of New Cytotoxic Aminoanthraquinone Derivatives via Nucleophilic Substitution Reactions
Molecules 2013, 18(7), 8046-8062; doi:10.3390/molecules18078046
Received: 14 May 2013 / Revised: 21 June 2013 / Accepted: 25 June 2013 / Published: 8 July 2013
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Abstract
Aminoanthraquinones were successfully synthesized via two reaction steps. 1,4-Dihydroxyanthraquinone (1) was first subjected to methylation, reduction and acylation to give an excellent yield of anthracene-1,4-dione (3), 1,4-dimethoxyanthracene-9,10-dione (5) and 9,10-dioxo-9,10-dihydroanthracene-1,4-diyl diacetate (7). Treatment of [...] Read more.
Aminoanthraquinones were successfully synthesized via two reaction steps. 1,4-Dihydroxyanthraquinone (1) was first subjected to methylation, reduction and acylation to give an excellent yield of anthracene-1,4-dione (3), 1,4-dimethoxyanthracene-9,10-dione (5) and 9,10-dioxo-9,10-dihydroanthracene-1,4-diyl diacetate (7). Treatment of 1, 3, 5 and 7 with BuNH2 in the presence of PhI(OAc)2 as catalyst produced seven aminoanthraquinone derivatives 1a, b, 3a, and 5ad. Amination of 3 and 5 afforded three new aminoanthraquinones, namely 2-(butylamino)anthracene-1,4-dione (3a), 2-(butylamino)anthracene-9,10-dione (5a) and 2,3-(dibutylamino)anthracene-9,10-dione (5b). All newly synthesised aminoanthraquinones were examined for their cytotoxic activity against MCF-7 (estrogen receptor positive human breast) and Hep-G2 (human hepatocellular liver carcinoma) cancer cells using MTT assay. Aminoanthraquinones 3a, 5a and 5b exhibited strong cytotoxicity towards both cancer cell lines (IC50 1.1–13.0 µg/mL). Full article
(This article belongs to the Section Organic Synthesis)
Open AccessArticle In-Solution Conformational Analysis of the XCYCH3 Moiety for Small Esters and Ethers with all Combinations of X, Y = O, S
Molecules 2013, 18(7), 8063-8082; doi:10.3390/molecules18078063
Received: 16 March 2013 / Revised: 1 July 2013 / Accepted: 3 July 2013 / Published: 8 July 2013
Cited by 3 | PDF Full-text (253 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Favorable steric and electrostatic fit of a ligand to a receptor is of central interest in theoretical drug design. This paper considers the effects of non-protic solvents, in comparison with the gas phase, on the preferred conformation of the XCYCH3 moiety [...] Read more.
Favorable steric and electrostatic fit of a ligand to a receptor is of central interest in theoretical drug design. This paper considers the effects of non-protic solvents, in comparison with the gas phase, on the preferred conformation of the XCYCH3 moiety of simple aliphatic esters and heterocyclic methyl ethers with all combinations of the X and Y atoms as oxygen and sulfur. An IEF-PCM/B97D/aug-cc-pv(t+d)z continuum dielectric solvent study in chloroform and acetonitrile explores the through-space polarization effect of the environment on the conformational preference, not affected by possible solute-solvent hydrogen bond formation. The inherently favored structure for the present molecules is important, since the hypothetical oxygen and sulfur lone-pairs point approximately in opposite directions in the cis conformation of esters, whereas the trans and gauche conformations for the methyl group in ethers define nearly parallel or perpendicular directionality for the lone pairs of the ring heteroatoms and the O or S atoms connecting to the ring. These different preferences for the studied two families of compounds allow for designing formation of hydrogen bonds with a protein in fairly different regions of the latter still within the ligand-binding cavity. For a fine-tuning of these hydrogen bonds, a replacement of an oxygen atom of the ligand by a sulfur atom could be a straightforward possibility. Full article
(This article belongs to the Special Issue Computational Chemistry)
Open AccessArticle Luteolin Inhibits Inflammatory Responses via p38/MK2/TTP-mediated mRNA Stability
Molecules 2013, 18(7), 8083-8094; doi:10.3390/molecules18078083
Received: 2 May 2013 / Revised: 3 July 2013 / Accepted: 4 July 2013 / Published: 9 July 2013
Cited by 8 | PDF Full-text (1372 KB) | HTML Full-text | XML Full-text
Abstract
Luteolin (Lut) is a common dietary flavonoid present in Chinese herbal medicines that has been reported to have important anti-inflammatory properties. The purposes of this study were to observe the inhibition of lipopolysaccharide (LPS)-induced inflammatory responses in bone marrow macrophages (BMM) by [...] Read more.
Luteolin (Lut) is a common dietary flavonoid present in Chinese herbal medicines that has been reported to have important anti-inflammatory properties. The purposes of this study were to observe the inhibition of lipopolysaccharide (LPS)-induced inflammatory responses in bone marrow macrophages (BMM) by Lut, and to examine whether this inhibition involves p38/MK2/TTP-mediated mRNA stability. Lut suppressed the production of tumor necrosis factor-α (TNF-α) and interleukin-6 (IL-6) in a dose-dependent manner according to enzyme-linked immunosorbent assay (ELISA) analysis. Lut also shortened the half-lives of the TNF-α and IL-6 mRNAs according to real-time PCR analysis. Western blots were performed to assess the activation of p38 and MK2 as well as the expression of TTP. The results indicated that Lut inhibited p38 and MK2 phosphorylation while promoting TTP expression. These results suggest that the anti-inflammatory effects of Lut are partially mediated through p38/MK2/TTP-regulated mRNA stability. Full article
(This article belongs to the Special Issue Anti-Inflammatory & Anti-Allergy Agents in Medicinal Chemistry)
Open AccessArticle Anti-Candida Targets and Cytotoxicity of Casuarinin Isolated from Plinia cauliflora Leaves in a Bioactivity-Guided Study
Molecules 2013, 18(7), 8095-8108; doi:10.3390/molecules18078095
Received: 27 May 2013 / Revised: 5 July 2013 / Accepted: 5 July 2013 / Published: 9 July 2013
Cited by 2 | PDF Full-text (328 KB) | HTML Full-text | XML Full-text
Abstract
In addition to the bio-guided investigation of the antifungal activity of Plinia cauliflora leaves against different Candida species, the major aim of the present study was the search for targets on the fungal cell. The most active antifungal fraction was purified by [...] Read more.
In addition to the bio-guided investigation of the antifungal activity of Plinia cauliflora leaves against different Candida species, the major aim of the present study was the search for targets on the fungal cell. The most active antifungal fraction was purified by chromatography and characterized by NMR and mass spectrometry. The antifungal activity was evaluated against five Candida strains according to referenced guidelines. Cytotoxicity against fibroblast cells was determined. The likely targets of Candida albicans cells were assessed through interactions with ergosterol and cell wall composition, porosity and architecture. The chemical major component within the most active antifungal fraction of P. cauliflora leaves identified was the hydrolysable tannin casuarinin. The cytotoxic concentration was higher than the antifungal one. The first indication of plant target on cellular integrity was suggested by the antifungal activity ameliorated when using an osmotic support. The most important target for the tannin fraction studied was suggested by ultrastructural analysis of yeast cell walls revealing a denser mannan outer layer and wall porosity reduced. It is possible to imply that P. cauliflora targeted the C. albicans cell wall inducing some changes in the architecture, notably the outer glycoprotein layer, affecting the cell wall porosity without alteration of the polysaccharide or protein level. Full article
(This article belongs to the Section Natural Products)
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Open AccessCommunication Apoptosis-Inducing Effect of Ginsenoside Rg6 on Human Lymphocytoma JK Cells
Molecules 2013, 18(7), 8109-8119; doi:10.3390/molecules18078109
Received: 13 May 2013 / Revised: 26 June 2013 / Accepted: 4 July 2013 / Published: 9 July 2013
Cited by 4 | PDF Full-text (644 KB) | HTML Full-text | XML Full-text
Abstract
In this communication our aim was to study the JK cell growth inhibitory and apoptosis-inducing effects of ginsenoside Rg6 (GRg6) from steamed notoginseng on human lymphocytoma. The CCK-8 method was used to observe the anti-proliferative effect of GRg6 on human lymphocytoma JK [...] Read more.
In this communication our aim was to study the JK cell growth inhibitory and apoptosis-inducing effects of ginsenoside Rg6 (GRg6) from steamed notoginseng on human lymphocytoma. The CCK-8 method was used to observe the anti-proliferative effect of GRg6 on human lymphocytoma JK cells. Flow cytometry was performed to analyze the influence of GRg6 on cell cycle. The Annexin-V FITC/PI double-staining method was used to detect the ratio of apoptotic cells. JC-1 staining was undertaken to observe the influence of GRg6 on intracellular mitochondrial membrane potential. Finally, western blots were conducted to detect the expression level of apoptosis-related Bax and the Bcl-2 proteins. The results suggested that GRg6 can inhibit the proliferation of human lymphocytoma JK cells. GRg6 blocks an S arrest in the cell cycle. With the increase in GRg6 concentration, the potential in the cell decreased in a dose dependent manner, and Bax protein expression gradually increased, whereas Bcl-2 protein expression gradually decreased. In conclusion, GRg6 can inhibit JK cell proliferation in human lymphocytoma and induce its apoptosis. The mechanism of action may be related to mitochondrial dysfunction and an increase of Bax expression and decrease of Bcl-2 expression caused by GRg6. Full article
(This article belongs to the Section Natural Products)
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Open AccessArticle Protective Mechanisms of Guanosine from Solanum lycopersicum on Agonist-Induced Platelet Activation: Role of sCD40L
Molecules 2013, 18(7), 8120-8135; doi:10.3390/molecules18078120
Received: 9 May 2013 / Revised: 8 June 2013 / Accepted: 3 July 2013 / Published: 10 July 2013
Cited by 11 | PDF Full-text (1595 KB) | HTML Full-text | XML Full-text
Abstract
In the past 30 years, only three natural products have been sources of new drugs with antiplatelet activity. In this study, we have demonstrated for the first time that guanosine from Solanum lycopersicum possesses antiplatelet (secretion, spreading, adhesion and aggregation) activity in [...] Read more.
In the past 30 years, only three natural products have been sources of new drugs with antiplatelet activity. In this study, we have demonstrated for the first time that guanosine from Solanum lycopersicum possesses antiplatelet (secretion, spreading, adhesion and aggregation) activity in vitro and inhibition of platelet inflammatory mediator of atherosclerosis (sCD40L). According to ADP-induced platelet aggregation inhibiting, the total extract residue was fractionated by liquid chromatography/phase separation, affording an aqueous fraction. This fraction was subjected to repeated permeation over Sephadex LH-20 and semi-preparative TLC. The isolated compound finally obtained was identified as guanosine on the basis of its UV-spectra, HPLC and 1H-NMR data. Guanosine concentration dose-dependently (1 to 4 mmol/L) inhibited platelet secretion and aggregation induced by ADP and collagen. Spread of human platelets on collagen in the presence of guanosine was fully inhibited. After incubation of whole blood with guanosine, the platelet adhesion and aggregation under flow conditions was inhibited concentration dependently (0.2 to 2 mmol/L). At the same concentrations that guanosine inhibits platelet aggregation, levels of sCD40L were significantly decreased. Guanosine is thus likely to exert significant protective effects in thromboembolic-related disorders by inhibiting platelet aggregation. Full article
(This article belongs to the Section Natural Products)
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Open AccessArticle Anti-Inflammatory Activity of Different Agave Plants and the Compound Cantalasaponin-1
Molecules 2013, 18(7), 8136-8146; doi:10.3390/molecules18078136
Received: 22 April 2013 / Revised: 29 May 2013 / Accepted: 6 June 2013 / Published: 10 July 2013
Cited by 6 | PDF Full-text (151 KB) | HTML Full-text | XML Full-text
Abstract
Species of the agave genus, such as Agave tequilana, Agave angustifolia and Agave americana are used in Mexican traditional medicine to treat inflammation-associated conditions. These plants’ leaves contain saponin compounds which show anti-inflammatory properties in different models. The goal of this [...] Read more.
Species of the agave genus, such as Agave tequilana, Agave angustifolia and Agave americana are used in Mexican traditional medicine to treat inflammation-associated conditions. These plants’ leaves contain saponin compounds which show anti-inflammatory properties in different models. The goal of this investigation was to evaluate the anti-inflammatory capacity of these plants, identify which is the most active, and isolate the active compound by a bio-directed fractionation using the ear edema induced in mice with 12-O-tetradecanoylphorbol-13-acetate (TPA) technique. A dose of 6 mg/ear of acetone extract from the three agave species induced anti-inflammatory effects, however, the one from A. americana proved to be the most active. Different fractions of this species showed biological activity. Finally the F5 fraction at 2.0 mg/ear induced an inhibition of 85.6%. We identified one compound in this fraction as (25R)-5α-spirostan-3β,6α,23α-triol-3,6-di-O-β-D-glucopyranoside (cantalasaponin-1) through 1H- and 13C-NMR spectral analysis and two dimensional experiments like DEPT NMR, COSY, HSQC and HMBC. This steroidal glycoside showed a dose dependent effect of up to 90% of ear edema inhibition at the highest dose of 1.5 mg/ear. Full article
(This article belongs to the Section Natural Products)
Open AccessArticle Synthesis of Tricyclic Condensed Rings Incorporating the Pyrazole or Isoxazole Moieties Bonded to a 4-Piperidinyl Substituent
Molecules 2013, 18(7), 8147-8159; doi:10.3390/molecules18078147
Received: 3 June 2013 / Revised: 1 July 2013 / Accepted: 2 July 2013 / Published: 10 July 2013
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Abstract
In this paper we report the synthesis of new compounds based on the pyrazole and isoxazole framework fused to a cycloalkene unit, and bearing as a substituent the 1-piperidinyl group as new examples of potential antipsychotic molecules. The general synthesis involves the [...] Read more.
In this paper we report the synthesis of new compounds based on the pyrazole and isoxazole framework fused to a cycloalkene unit, and bearing as a substituent the 1-piperidinyl group as new examples of potential antipsychotic molecules. The general synthesis involves the acylation of a chloro-substituted cyclic ketone with a 1-substituted piperidine-4-carboxylate derivative, followed by heterocyclization of the formed 1,3-dioxo compound with a hydrazine or hydroxylamine. Full article
(This article belongs to the Section Organic Synthesis)
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Open AccessArticle Flexibilisquinone, a New Anti-Inflammatory Quinone from the Cultured Soft Coral Sinularia flexibilis
Molecules 2013, 18(7), 8160-8167; doi:10.3390/molecules18078160
Received: 27 May 2013 / Revised: 4 July 2013 / Accepted: 8 July 2013 / Published: 10 July 2013
Cited by 10 | PDF Full-text (514 KB) | HTML Full-text | XML Full-text
Abstract
A new quinone derivative, flexibilisquinone (1), was isolated from the cultured soft coral Sinularia flexibilis, originally distributed in the waters of Taiwan. The structure of quinone 1 was established by extensive spectroscopic methods, particularly 1D and 2D NMR experiments. [...] Read more.
A new quinone derivative, flexibilisquinone (1), was isolated from the cultured soft coral Sinularia flexibilis, originally distributed in the waters of Taiwan. The structure of quinone 1 was established by extensive spectroscopic methods, particularly 1D and 2D NMR experiments. In the in vitro anti-inflammatory effects test, quinone 1 was found to significantly inhibit the accumulation of the pro-inflammatory iNOS and COX-2 proteins of the LPS-stimulated RAW264.7 macrophage cells. Full article
Open AccessArticle Preparation of a Sulfonated Carbonaceous Material from Lignosulfonate and Its Usefulness as an Esterification Catalyst
Molecules 2013, 18(7), 8168-8180; doi:10.3390/molecules18078168
Received: 3 May 2013 / Revised: 26 June 2013 / Accepted: 8 July 2013 / Published: 10 July 2013
Cited by 23 | PDF Full-text (314 KB) | HTML Full-text | XML Full-text
Abstract
Sulfonated carbonaceous material useful as a solid acid catalyst was prepared from lignosulfonate, a waste of the paper-making industry sulfite pulping process, and characterized by 13C-NMR, FT-IR, TGA, SEM and elemental analysis, etc. The sulfonic acid group density and total [...] Read more.
Sulfonated carbonaceous material useful as a solid acid catalyst was prepared from lignosulfonate, a waste of the paper-making industry sulfite pulping process, and characterized by 13C-NMR, FT-IR, TGA, SEM and elemental analysis, etc. The sulfonic acid group density and total density of all acid groups in the sulfonated carbonaceous material was determined by titration to be 1.24 mmol/g and 5.90 mmol/g, respectively. Its catalytic activity in the esterification of cyclohexanecarboxylic acid with anhydrous ethanol was shown to be comparable to that of the ionic exchange resin Amberlyst-15, when they were used in the same amount. In the meantime, the sulfonic acid group was found to be leached out by 26%–29% after it was exposed to hot water (95 °C) for 5 h. The catalytic usefulness of the prepared carbonaceous material was investigated by performing esterifications. Full article
(This article belongs to the Section Organic Synthesis)
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Open AccessArticle Purification of Ustiloxins A and B from Rice False Smut Balls by Macroporous Resins
Molecules 2013, 18(7), 8181-8199; doi:10.3390/molecules18078181
Received: 3 June 2013 / Revised: 26 June 2013 / Accepted: 8 July 2013 / Published: 11 July 2013
Cited by 5 | PDF Full-text (286 KB) | HTML Full-text | XML Full-text
Abstract
Ustiloxins are cyclopeptide mycotoxins produced by Villosiclava virens, the pathogenic fungus of rice false smut disease. Both resins SP207 and SP700 were screened to show the best adsorption and desorption properties for ustiloxins A and B among 20 commercial macroporous resins. [...] Read more.
Ustiloxins are cyclopeptide mycotoxins produced by Villosiclava virens, the pathogenic fungus of rice false smut disease. Both resins SP207 and SP700 were screened to show the best adsorption and desorption properties for ustiloxins A and B among 20 commercial macroporous resins. Dynamic adsorption and desorption tests were carried out to optimize the process parameters. The optimal conditions for adsorption of resin SP207 were a processing volume as 32 bed volumes (BV), pH value of 4, and flow rate of 2 BV/h; and those for desorption of resin SP207 were a 40:60 (v/v) ratio of ethanol to water, an eluent volume of 4 BV, pH value of 4 and a flow rate of 3 BV/h. The optimal conditions for adsorption of resin SP700 were a processing volume of 26 BV, pH value as 4, flow rate of 2 BV/h; and those for desorption of resin SP700 were a 30:70 (v/v) ratio of ethanol to water solution as eluent, volume of 4 BV, pH value as 4 and flow rate of 2 BV/h. Under the optimal conditions; the purities of ustiloxins A and B obtained with resin SP207 increased 23.06-fold and 19.78-fold, respectively; and their recoveries were 96.67% and 81.25%; respectively. Similarly; the purities of ustiloxins A and B obtained with resin SP700 increased 14.75-fold and 15.33-fold and their recoveries were 93.65% and 88.64%; respectively. The results show that adsorption and desorption on SP207 and SP700 resins are effective strategies for purifying ustiloxins A and B. The developed methods are beneficial for large-scale preparation and purification of ustiloxins A and B from rice false smut balls. Full article
(This article belongs to the Section Natural Products)
Open AccessArticle Studies toward the First Stereoselective Total Synthesis of (±)-Quinolizidine 195C and Other Transformations
Molecules 2013, 18(7), 8243-8256; doi:10.3390/molecules18078243
Received: 16 May 2013 / Revised: 2 July 2013 / Accepted: 3 July 2013 / Published: 12 July 2013
Cited by 5 | PDF Full-text (251 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Starting from a thio-substituted 4-quinolizidinone, a series of C-6 alkylated derivatives with a trans C-6, C-9a relationship was synthesized. Further transformations led to the first stereoselective total synthesis of the structure proposed for (±)-quinolizidine 195C, the major alkaloid isolated from the skin [...] Read more.
Starting from a thio-substituted 4-quinolizidinone, a series of C-6 alkylated derivatives with a trans C-6, C-9a relationship was synthesized. Further transformations led to the first stereoselective total synthesis of the structure proposed for (±)-quinolizidine 195C, the major alkaloid isolated from the skin extracts of the Madagascan frog Mantella betsileo. Since the spectral data of the synthetic and natural products differed significantly, the true structure of (±)-quinolizidine 195C remains uncertain. Full article
(This article belongs to the Section Organic Synthesis)
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Open AccessArticle Morphology and Metal Binding Characteristics of a Natural Polymer—Kondagogu (Cochlospermum gossypium) Gum
Molecules 2013, 18(7), 8264-8274; doi:10.3390/molecules18078264
Received: 15 April 2013 / Revised: 26 June 2013 / Accepted: 27 June 2013 / Published: 15 July 2013
Cited by 4 | PDF Full-text (5189 KB) | HTML Full-text | XML Full-text
Abstract
Kondagogu (Cochlospermum gossypium) gum (KG), a natural tree exudate, was investigated for its morphological, adsorption and metal interaction behavior with various toxic heavy metals (Pb, Cd, Ni, Cr and Fe). SEM, AFM and TEM techniques were used to study the [...] Read more.
Kondagogu (Cochlospermum gossypium) gum (KG), a natural tree exudate, was investigated for its morphological, adsorption and metal interaction behavior with various toxic heavy metals (Pb, Cd, Ni, Cr and Fe). SEM, AFM and TEM techniques were used to study the morphological changes occurring after metal adsorption onto the biopolymer structure. The degree of biosorption of metals on KG biopolymer surfaces was assessed by small-angle X-ray scattering analysis. EDXA spectrum revealed that the ion-exchange mechanism plays a major role in the binding process between KG and metal ions. The higher electron density observed in the KG-Cd complex suggests that Cd is strongly bound to KG compared to the other metals. This work provides a potential platform for developing a hydrocolloid-based nanogel for bioremediation of environmental contaminants. Full article
(This article belongs to the Section Natural Products)
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Open AccessArticle Differential Growth Inhibitory Effects of Highly Oxygenated Guaianolides Isolated from the Middle Eastern Indigenous Plant Achillea falcata in HCT-116 Colorectal Cancer Cells
Molecules 2013, 18(7), 8275-8288; doi:10.3390/molecules18078275
Received: 21 May 2013 / Revised: 20 June 2013 / Accepted: 8 July 2013 / Published: 15 July 2013
Cited by 4 | PDF Full-text (297 KB) | HTML Full-text | XML Full-text
Abstract
Medicinal plants play a crucial role in traditional medicine and in the maintenance of human health worldwide. Sesquiterpene lactones represent an interesting group of plant-derived compounds that are currently being tested as lead drugs in cancer clinical trials. Achillea falcata is a [...] Read more.
Medicinal plants play a crucial role in traditional medicine and in the maintenance of human health worldwide. Sesquiterpene lactones represent an interesting group of plant-derived compounds that are currently being tested as lead drugs in cancer clinical trials. Achillea falcata is a medicinal plant indigenous to the Middle Eastern region and belongs to the Asteraceae family, which is known to be rich in sesquiterpene lactones. We subjected Achillea falcata extracts to bioassay-guided fractionation against the growth of HCT-116 colorectal cancer cells and identified four secotanapartholides, namely 3-β-methoxy- isosecotanapartholide (1), isosecotanapartholide (2), tanaphallin (3), and 8-hydroxy-3-methoxyisosecotanapartholide (4). Three highly oxygenated guaianolides were isolated for the first time from Achillea falcata, namely rupin A (5), chrysartemin B (6), and 1β, 2β-epoxy- 3β,4α,10α-trihydroxyguaian- 6α,12-olide (7). These sesquiterpene lactones showed no or minor cytotoxicity while exhibiting promising anticancer effects against HCT-116 cells. Further structure-activity relationship studies related the bioactivity of the tested compounds to their skeleton, their lipophilicity, and to the type of functional groups neighboring the main alkylating center of the molecule. Full article
(This article belongs to the Special Issue Bioassay-Guided Isolation of Natural Products)
Open AccessArticle Enhanced Stability of CaO and/or La2O3 Promoted Pd/Al2O3 Egg-Shell Catalysts in Partial Oxidation of Methane to Syngas
Molecules 2013, 18(7), 8289-8297; doi:10.3390/molecules18078289
Received: 17 June 2013 / Revised: 5 July 2013 / Accepted: 9 July 2013 / Published: 15 July 2013
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Abstract
An egg-shell Pd/Al2O3 catalyst showed higher activity than a regular Pd/Al2O3 catalyst in the partial oxidation of methane to syngas, but a common problem of this reaction is the catalyst deactivation on stream. We attempted to [...] Read more.
An egg-shell Pd/Al2O3 catalyst showed higher activity than a regular Pd/Al2O3 catalyst in the partial oxidation of methane to syngas, but a common problem of this reaction is the catalyst deactivation on stream. We attempted to modify the egg-shell catalyst via impregnation with some metal oxide additives. Although the addition of MgO did not show any beneficial effect, the addition of CaO and/or La2O3 significantly improved the stability due to the suppression of carbon deposition and phase transformation of the Al2O3 support. The catalysts were characterized by X-ray diffraction (XRD), N2 adsorption-desorption, and thermogravimetric analysis (TGA). Full article
(This article belongs to the Special Issue Palladium Catalysts)
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Open AccessArticle Factors Influencing the Antifolate Activity of Synthetic Tea-Derived Catechins
Molecules 2013, 18(7), 8319-8341; doi:10.3390/molecules18078319
Received: 7 June 2013 / Revised: 5 July 2013 / Accepted: 12 July 2013 / Published: 16 July 2013
Cited by 2 | PDF Full-text (802 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Novel tea catechin derivatives have been synthesized, and a structure-activity study, related to the capacity of these and other polyphenols to bind dihydrofolate reductase (DHFR), has been performed. The data showed an effective binding between all molecules and the free enzyme, and [...] Read more.
Novel tea catechin derivatives have been synthesized, and a structure-activity study, related to the capacity of these and other polyphenols to bind dihydrofolate reductase (DHFR), has been performed. The data showed an effective binding between all molecules and the free enzyme, and the dissociation constants of the synthetic compounds and of the natural analogues were on the same order. Polyphenols with a catechin configuration were better DHFR inhibitors than those with an epicatechin configuration. Antiproliferative activity was also studied in cultured tumour cells, and the data showed that the activity of the novel derivatives was higher in catechin isomers. Derivatives with a hydroxyl group para on the ester-bonded gallate moiety presented a high in vitro binding to DHFR, but exhibited transport problems in cell culture due to ionization at physiologic pHs. The impact of the binding of catechins to serum albumin on their biological activity was also evaluated. The information provided in this study could be important for the design of novel medicinal active compounds derived from tea catechins. The data suggest that changes in their structure to avoid serum albumin interactions and to facilitate plasmatic membrane transport are essential for the intracellular functions of catechins. Full article
(This article belongs to the Special Issue Structure-Activity Relationship of Flavonoids)
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Open AccessArticle HPLC Analysis of Phenolics Compounds and Antioxidant Capacity of Leaves of Vitex megapotamica (Sprengel) Moldenke
Molecules 2013, 18(7), 8342-8357; doi:10.3390/molecules18078342
Received: 13 June 2013 / Revised: 10 July 2013 / Accepted: 10 July 2013 / Published: 16 July 2013
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Abstract
Vitex megapotamica (Sprengel) Moldenke belongs to the Verbenaceae family and is popularly known as “tarumã”. The antioxidant capacity of fractions and crude extract from the leaves of V. megapotamica were determined in this study through the capacity to remove reactive species and [...] Read more.
Vitex megapotamica (Sprengel) Moldenke belongs to the Verbenaceae family and is popularly known as “tarumã”. The antioxidant capacity of fractions and crude extract from the leaves of V. megapotamica were determined in this study through the capacity to remove reactive species and phenolic compounds were quantified in the various fractions. The IC50 (DPPH) ranged from 14.17 ± 0.76 to 37.63 ± 0.98 µg/mL. The ethyl acetate fraction might contain the strongest lipid peroxidation inhibitory compounds with an IC50 of 16.36 ± 5.09 µg/mL, being also the one with the highest content of polyphenols (522.4 ± 1.12 mg/g), flavonoids (220.48 ± 0.30 mg/g) and condensed tannins (3.86 ± 0.53 mg/g). Compounds quantified by HPLC/DAD in the crude extract and fractions were chlorogenic and rosmarinic acids. Higher dosages of the extracts were more effective in reducing levels of plasma protein carbonyls and were also shown to be able to remove reactive species by a 2',7'-dichlorofluorescein diacetate assay, reducing oxidative stress in all tested fractions. Results obtained indicated that V. megapotamica exhibits good potential to prevent diseases caused by the overproduction of free radicals and it might also be used as a potential source of natural antioxidant agents. Full article
(This article belongs to the Section Natural Products)
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Open AccessArticle Thermal Behavior of Pinan-2-ol and Linalool
Molecules 2013, 18(7), 8358-8375; doi:10.3390/molecules18078358
Received: 29 May 2013 / Revised: 26 June 2013 / Accepted: 11 July 2013 / Published: 16 July 2013
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Abstract
Linalool is an important intermediate for syntheses of isoprenoid fragrance compounds and vitamins A and E. One process option for its production is the thermal gas-phase isomerization of cis- and trans-pinan-2-ol. Investigations of this reaction were performed in a flow-type [...] Read more.
Linalool is an important intermediate for syntheses of isoprenoid fragrance compounds and vitamins A and E. One process option for its production is the thermal gas-phase isomerization of cis- and trans-pinan-2-ol. Investigations of this reaction were performed in a flow-type apparatus in a temperature range from 350–600 °C and a residence time range of 0.6–0.8 s. Rearrangement of the bicyclic alcohol led to linalool, plinols arising from consecutive reactions of linalool and other side products. Effects of residence time, temperature, surface-to-volume-ratio, carrier gas, and the presence of additives on yield and selectivity were studied. Furthermore, the effects of such parameters on ene-cyclization of linalool affording plinols were investigated. Results indicate that manipulation of the reaction in order to affect selectivity is difficult due to the large free path length to other molecules in the gas phase. However, conditions have been identified allowing one to increase the selectivity and the yield of linalool throughout pyrolysis of pinan-2-ol. Full article
(This article belongs to the Special Issue Gas Phase Reactions)
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Open AccessArticle Development of 65 Novel Polymorphic cDNA-SSR Markers in Common Vetch (Vicia sativa subsp. sativa) Using Next Generation Sequencing
Molecules 2013, 18(7), 8376-8392; doi:10.3390/molecules18078376
Received: 2 May 2013 / Revised: 5 July 2013 / Accepted: 12 July 2013 / Published: 16 July 2013
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Abstract
Vetch (Vicia sativa L.) is one of the most important annual forage legumes in the World due to its multiple uses (i.e., hay, grain, silage and green manure) and high nutritional value. However, detrimental cyanoalanine toxins in its plant [...] Read more.
Vetch (Vicia sativa L.) is one of the most important annual forage legumes in the World due to its multiple uses (i.e., hay, grain, silage and green manure) and high nutritional value. However, detrimental cyanoalanine toxins in its plant parts including seeds and its vulnerability to hard winter conditions are currently reducing the agronomic values of vetch varieties. Moreover, the existence in the public domain of very few genomic resources, especially molecular markers, has further hampered breeding efforts. Polymorphic simple sequence repeat markers from transcript sequences (cDNA; simple sequence repeat [SSR]) were developed for Vicia sativa subsp. sativa. We found 3,811 SSR loci from 31,504 individual sequence reads, and 300 primer pairs were designed and synthesized. In total, 65 primer pairs were found to be consistently scorable when 32 accessions were tested. The numbers of alleles ranged from 2 to 19, frequency of major alleles per locus were 0.27–0.87, the genotype number was 2–19, the overall polymorphism information content (PIC) values were 0.20–0.86, and the observed and expected heterozygosity values were 0.00–0.41 and 0.264–0.852, respectively. These markers provide a useful tool for assessing genetic diversity, population structure, and positional cloning, facilitating vetch breeding programs. Full article
(This article belongs to the Section Molecular Diversity)
Open AccessArticle Distinct Metabolites for Photoreactive l-Phenylalanine Derivatives in Klebsiella sp. CK6 Isolated from Rhizosphere of a Wild Dipterocarp Sapling
Molecules 2013, 18(7), 8393-8401; doi:10.3390/molecules18078393
Received: 14 June 2013 / Revised: 2 July 2013 / Accepted: 11 July 2013 / Published: 16 July 2013
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Abstract
Photoaffinity labeling is a reliable analytical method for biological functional analysis. Three major photophores—aryl azide, benzophenone and trifluoromethyldiazirine—are utilized in analysis. Photophore-bearing l-phenylalanine derivatives, which are used for biological functional analysis, were inoculated into a Klebsiella sp. isolated from the rhizosphere of [...] Read more.
Photoaffinity labeling is a reliable analytical method for biological functional analysis. Three major photophores—aryl azide, benzophenone and trifluoromethyldiazirine—are utilized in analysis. Photophore-bearing l-phenylalanine derivatives, which are used for biological functional analysis, were inoculated into a Klebsiella sp. isolated from the rhizosphere of a wild dipterocarp sapling in Central Kalimantan, Indonesia, under nitrogen-limiting conditions. The proportions of metabolites were quite distinct for each photophore. These results indicated that photophores affected substrate recognition in rhizobacterial metabolic pathways, and differential photoaffinity labeling could be achieved using different photophore-containing l-phenylalanine derivatives. Full article
(This article belongs to the Special Issue Reagents and Methods for Protein Target Identification)
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Open AccessArticle Characterization of Flavonoids and Phenolic Acids in Myrcia bella Cambess. Using FIA-ESI-IT-MSn and HPLC-PAD-ESI-IT-MS Combined with NMR
Molecules 2013, 18(7), 8402-8416; doi:10.3390/molecules18078402
Received: 7 June 2013 / Revised: 5 July 2013 / Accepted: 8 July 2013 / Published: 16 July 2013
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Abstract
The leaves of Myrcia DC. ex Guill species are used in traditional medicine and are also exploited commercially as herbal drugs for the treatment of diabetes mellitus. The present work aimed to assess the qualitative and quantitative profiles of M. bella hydroalcoholic [...] Read more.
The leaves of Myrcia DC. ex Guill species are used in traditional medicine and are also exploited commercially as herbal drugs for the treatment of diabetes mellitus. The present work aimed to assess the qualitative and quantitative profiles of M. bella hydroalcoholic extract, due to these uses, since the existing legislation in Brazil determines that a standard method must be developed in order to be used for quality control of raw plant materials. The current study identified eleven known flavonoid-O-glycosides and six acylated flavonoid derivatives of myricetin and quercetin, together with two kaempferol glycosides and phenolic acids such as caffeic acid, ethil galate, gallic acid and quinic acid. In total, 24 constituents were characterized, by means of extensive preparative chromatographic analyses, along with MS and NMR techniques. An HPLC-PAD-ESI-IT-MS and FIA-ESI-IT-MSn method were developed for rapid identification of acylated flavonoids, flavonoid-O-glycosides derivatives of myricetin and quercetin and phenolic acids in the hydroalcoholic M. bella leaves extract. The FIA-ESI-IT-MS techinique is a powerful tool for direct and rapid identification of the constituents after isolation and NMR characterization. Thus, it could be used as an initial method for identification of authentic samples concerning quality control of Myrcia spp extracts. Full article
(This article belongs to the Section Natural Products)
Open AccessCommunication Characterization of Water Extractable Arabinoxylans from a Spring Wheat Flour: Rheological Properties and Microstructure
Molecules 2013, 18(7), 8417-8428; doi:10.3390/molecules18078417
Received: 24 May 2013 / Revised: 10 July 2013 / Accepted: 10 July 2013 / Published: 16 July 2013
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Abstract
In the present study water extractable arabinoxylans (WEAX) from a Mexican spring wheat flour (cv. Tacupeto F2001) were isolated, characterized and gelled and the gel rheological properties and microstructure were investigated. These WEAX presented an arabinose to xylose ratio of 0.66, a [...] Read more.
In the present study water extractable arabinoxylans (WEAX) from a Mexican spring wheat flour (cv. Tacupeto F2001) were isolated, characterized and gelled and the gel rheological properties and microstructure were investigated. These WEAX presented an arabinose to xylose ratio of 0.66, a ferulic acid and diferulic acid content of 0.526 and 0.036 µg/mg WEAX, respectively and a Fourier Transform Infra-Red (FT-IR) spectrum typical of arabinoxylans. The intrinsic viscosity and viscosimetric molecular weight values for WEAX were 3.5 dL/g and 504 kDa, respectively. WEAX solution at 2% (w/v) formed gels induced by a laccase as cross-linking agent. Cured WEAX gels registered storage (G’) and loss (G’’) modulus values of 31 and 5 Pa, respectively and a diferulic acid content of 0.12 µg/mg WEAX, only traces of triferulic acid were detected. Scanning electron microscopy analysis of the lyophilized WEAX gels showed that this material resembles that of an imperfect honeycomb. Full article
(This article belongs to the Section Natural Products)
Open AccessArticle Separation and Identification of 1,2,4-Trihydroxynaphthalene-1-O-glucoside in Impatiens glandulifera Royle
Molecules 2013, 18(7), 8429-8439; doi:10.3390/molecules18078429
Received: 24 May 2013 / Revised: 10 July 2013 / Accepted: 10 July 2013 / Published: 17 July 2013
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Abstract
Methanolic extract from lyophilized roots of Impatiens glandulifera Royle was analyzed by high performance liquid chromatography using DAD and FLD detection and this revealed one dominant highly fluorescent very unstable substance. The stability of this derivative is strongly dependent on the plant [...] Read more.
Methanolic extract from lyophilized roots of Impatiens glandulifera Royle was analyzed by high performance liquid chromatography using DAD and FLD detection and this revealed one dominant highly fluorescent very unstable substance. The stability of this derivative is strongly dependent on the plant material drying procedure and extraction procedure used. The structure of the substance was established as 1,2,4-trihydroxynaphthalene-1-O-glucoside (THNG) according LC-MS and NMR measurements. When lyophilized plant material was extracted with methanol an almost four times higher amount of THNG was found in the extract, compared to the amount of 2-hydroxy-1,4-naphthoquinone obtained, while in the case of the same lyophilized plant material extracted with water there was no THNG in the extract. The main compounds in this case was 2-hydroxy-1,4-naphthoquinone. In the plant material dried at the laboratory temperature and extracted by methanol there are only traces of THNG. Full article
(This article belongs to the Section Natural Products)
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Open AccessArticle Preparation and Characterization of Poly(ethyl hydrazide)-Grafted Oil Palm Empty Fruit Bunch Fibre for the Removal of Cu(II) Ions from an Aqueous Environment
Molecules 2013, 18(7), 8461-8472; doi:10.3390/molecules18078461
Received: 1 March 2013 / Revised: 26 June 2013 / Accepted: 27 June 2013 / Published: 18 July 2013
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Abstract
Poly(ethyl hydrazide)-grafted oil palm empty fruit bunch fibre (peh-g-opefb) was successfully prepared by heating poly(methyl acrylate)-grafted opefb (pma-g-opefb) at 60 °C for 4 h with a solution of hydrazine hydrate (15% v/v) in ethanol. The Fourier transform infrared spectrum of the product [...] Read more.
Poly(ethyl hydrazide)-grafted oil palm empty fruit bunch fibre (peh-g-opefb) was successfully prepared by heating poly(methyl acrylate)-grafted opefb (pma-g-opefb) at 60 °C for 4 h with a solution of hydrazine hydrate (15% v/v) in ethanol. The Fourier transform infrared spectrum of the product shows a secondary amine peak at 3267 cm−1, with amide carbonyl peaks at 1729 cm−1 and 1643 cm−1. The chelating ability of peh-g-opefb was tested with copper ion in aqueous solution. A batch adsorption study revealed that maximum adsorption of copper ion was achieved at pH 5. An isotherm study showed the adsorption follows a Langmuir model, with a maximum adsorption capacity of 43.48 mg g−1 at 25 °C. A kinetic study showed that the adsorption of copper ion rapidly reaches equilibrium and follows a pseudo–second-order kinetic model, with a constant rate of 7.02 × 10−4 g mg−1 min−1 at 25 °C. The Gibbs free energy, ∆G⁰, value is negative, indicating a spontaneous sorption process. Entropy, ∆S⁰, gives a positive value, indicating that the system is becoming increasingly disordered after the adsorption of copper ion. A positive enthalpy value, ∆H⁰, shows that the endothermic process takes place during the adsorption and is more favourable at high temperatures. Full article
Open AccessArticle Hydrophosphonylation of Nanoparticle Schiff Bases as a Mean for Preparation of Aminophosphonate-Functionalized Nanoparticles
Molecules 2013, 18(7), 8473-8484; doi:10.3390/molecules18078473
Received: 9 June 2013 / Revised: 9 July 2013 / Accepted: 15 July 2013 / Published: 18 July 2013
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Abstract
The development of nanotechnology is responsible for an increase in the achievements in medical diagnostics and in the preparation of new therapeutic vehicles. In particular, magnetic nanoparticles with a modified surface are a very attractive alternative to deliver therapeutic agents. We describe [...] Read more.
The development of nanotechnology is responsible for an increase in the achievements in medical diagnostics and in the preparation of new therapeutic vehicles. In particular, magnetic nanoparticles with a modified surface are a very attractive alternative to deliver therapeutic agents. We describe the modification of the surface of the iron oxide nanoparticles with aminophosphonic acids by applying the classic hydrophosphonylation approach. Full article
(This article belongs to the Special Issue Organophosphorus Chemistry)
Open AccessArticle Preliminary Phytochemical Screening and Antibacterial Properties of Crude Stem Bark Extracts and Fractions of Parkia biglobosa (Jacq.)
Molecules 2013, 18(7), 8485-8499; doi:10.3390/molecules18078485
Received: 18 April 2013 / Revised: 19 June 2013 / Accepted: 25 June 2013 / Published: 18 July 2013
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Abstract
A methanolic crude extract of Parkia biglobosa was prepared and later partitioned in succession with different solvents of increasing polarity ranging from n-hexane, chloroform and ethyl acetate to butanol. Phytochemical screening of the extract revealed the presence of alkaloids, tannins, saponins, [...] Read more.
A methanolic crude extract of Parkia biglobosa was prepared and later partitioned in succession with different solvents of increasing polarity ranging from n-hexane, chloroform and ethyl acetate to butanol. Phytochemical screening of the extract revealed the presence of alkaloids, tannins, saponins, flavonoids, steroids, glycoside and sugars. The inhibition zones exhibited by the extract against the tested bacteria ranged between 14 ± 0.00 mm (against Escherichia coli) and 28 ± 0.71 mm (against Pseudomonas aeruginosa). The MIC of the methanolic extract of P. biglobosa against isolates ranged between 0.63 mg/mL and 5 mg/mL, while the MIC values exhibited by the n-hexane and aqueous fractions ranged between 0.63 mg/mL and 10 mg/mL. Overall the extract and fractions of P. biglobosa used in this work were found to possess antimicrobial properties which compared favourably with those of streptomycin. These observations make this plant a potential source of bioactive compounds that can be used in management of bacterial infections. The use of this plant as herbal medicaments in African countries and the reports on the toxicity of the plant further show that the plant is non-toxic to humans. Full article
(This article belongs to the Section Natural Products)
Open AccessArticle Decomposition Mechanisms and Kinetics of Novel Energetic Molecules BNFF-1 and ANFF-1: Quantum-Chemical Modeling
Molecules 2013, 18(7), 8500-8517; doi:10.3390/molecules18078500
Received: 27 May 2013 / Revised: 13 July 2013 / Accepted: 16 July 2013 / Published: 18 July 2013
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Abstract
Decomposition mechanisms, activation barriers, Arrhenius parameters, and reaction kinetics of the novel explosive compounds, 3,4-bis(4-nitro-1,2,5-oxadiazol-3-yl)-1,2,5-oxadiazole (BNFF-1), and 3-(4-amino-1,2,5-oxadiazol-3-yl)-4-(4-nitro-1,2,5-oxadiazol-3-yl)-1,2,5-oxadiazole (ANFF-1) were explored by means of density functional theory with a range of functionals combined with variational transition state theory. BNFF-1 and ANFF-1 were [...] Read more.
Decomposition mechanisms, activation barriers, Arrhenius parameters, and reaction kinetics of the novel explosive compounds, 3,4-bis(4-nitro-1,2,5-oxadiazol-3-yl)-1,2,5-oxadiazole (BNFF-1), and 3-(4-amino-1,2,5-oxadiazol-3-yl)-4-(4-nitro-1,2,5-oxadiazol-3-yl)-1,2,5-oxadiazole (ANFF-1) were explored by means of density functional theory with a range of functionals combined with variational transition state theory. BNFF-1 and ANFF-1 were recently suggested to be good candidates for insensitive high energy density materials. Our modeling reveals that the decomposition initiation in both BNFF-1 and ANFF-1 molecules is triggered by ring cleavage reactions while the further process is defined by a competition between two major pathways, the fast C-NO2 homolysis and slow nitro-nitrite isomerization releasing NO. We discuss insights on design of new energetic materials with targeted properties gained from our modeling. Full article
(This article belongs to the Special Issue Computational Chemistry)
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Open AccessArticle Two New Chiratane-Type Triterpenoids from Swertia kouitchensis
Molecules 2013, 18(7), 8518-8523; doi:10.3390/molecules18078518
Received: 5 June 2013 / Revised: 2 July 2013 / Accepted: 10 July 2013 / Published: 18 July 2013
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Abstract
Two rare new chiratane-type triterpenoids, kouitchenoids A and B (1, 2), together with oleanolic acid (3) and ursolic acid (4), were isolated from ethanol extract of Swertia kouitchensis. The new structures were determined by [...] Read more.
Two rare new chiratane-type triterpenoids, kouitchenoids A and B (1, 2), together with oleanolic acid (3) and ursolic acid (4), were isolated from ethanol extract of Swertia kouitchensis. The new structures were determined by the analysis of MS and NMR data. In addition, compounds 14 showed moderate inhibitory activity against the α-glucosidase (with IC50 values ranging from 1,812 to 2,027 μM). Full article
(This article belongs to the Section Natural Products)
Open AccessArticle A Straightforward Diphenylmethyl Protection Method and Deprotection of Some Pyrimidine Nucleosides
Molecules 2013, 18(7), 8524-8534; doi:10.3390/molecules18078524
Received: 31 May 2013 / Revised: 10 July 2013 / Accepted: 16 July 2013 / Published: 18 July 2013
Cited by 4 | PDF Full-text (237 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Benzhydryl protection of primary and secondary alcohols has been reported previously via reaction with metal alcoholates. Our aim was to find generally useful and very mild conditions for the alcoholic protection and deprotection of nucleosides with the diphenylmethyl group. This was accomplished [...] Read more.
Benzhydryl protection of primary and secondary alcohols has been reported previously via reaction with metal alcoholates. Our aim was to find generally useful and very mild conditions for the alcoholic protection and deprotection of nucleosides with the diphenylmethyl group. This was accomplished for some pyrimidine nucleosides using PdCl2 as the transition metal catalyst, and with optimization yields of 70–90% have been achieved. A lack of solubility of other nucleosides hampers its more general use. Full article
(This article belongs to the Special Issue Synthesis of Nucleosides, Nucleotides and Their Derivatives)
Open AccessArticle Synthesis and Biological Evaluation of a New Acyclic Pyrimidine Derivative as a Probe for Imaging Herpes Simplex Virus Type 1 Thymidine Kinase Gene Expression
Molecules 2013, 18(7), 8535-8549; doi:10.3390/molecules18078535
Received: 27 May 2013 / Revised: 12 July 2013 / Accepted: 16 July 2013 / Published: 19 July 2013
Cited by 1 | PDF Full-text (494 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
With the idea of finding a more selective radiotracer for imaging herpes simplex virus type 1 thymidine kinase (HSV1-tk) gene expression by means of positron emission tomography (PET), a novel [18F]fluorine radiolabeled pyrimidine with 4-hydroxy-3-(hydroxymethyl)butyl side chain at N-1 [...] Read more.
With the idea of finding a more selective radiotracer for imaging herpes simplex virus type 1 thymidine kinase (HSV1-tk) gene expression by means of positron emission tomography (PET), a novel [18F]fluorine radiolabeled pyrimidine with 4-hydroxy-3-(hydroxymethyl)butyl side chain at N-1 (HHB-5-[18F]FEP) was prepared and evaluated as a potential PET probe. Unlabeled reference compound, HHB-5-FEP, was synthesized via a five-step reaction sequence starting from 5-(2-acetoxyethyl)-4-methoxypyrimidin-2-one. The radiosynthesis of HHB-[18F]-FEP was accomplished by nucleophilic radiofluorination of a tosylate precursor using [18F]fluoride-cryptate complex in 45% ± 4 (n = 4) radiochemical yields and high purity (>99%). The biological evaluation indicated the feasibility of using HHB-5-[18F]FEP as a PET radiotracer for monitoring HSV1-tk expression in vivo. Full article
(This article belongs to the Special Issue Synthesis of Nucleosides, Nucleotides and Their Derivatives)
Open AccessArticle Synthesis and Bioassay of a New Class of Furanyl-1,3,4-Oxadiazole Derivatives
Molecules 2013, 18(7), 8550-8562; doi:10.3390/molecules18078550
Received: 22 May 2013 / Revised: 19 June 2013 / Accepted: 20 June 2013 / Published: 19 July 2013
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Abstract
Tyrosinase enzyme is a monophenol monoxygenase enzyme, which plays an important role in human as a rate limiting step enzyme for different specific metabolic pathways, as well as its useful application in industry and agriculture. So this study was carried out to [...] Read more.
Tyrosinase enzyme is a monophenol monoxygenase enzyme, which plays an important role in human as a rate limiting step enzyme for different specific metabolic pathways, as well as its useful application in industry and agriculture. So this study was carried out to test the effect of newly prepared compounds containing 1,3,4-oxadiazoles with different substituted groups on tyrosinase enzyme activity, hoping to use them in the treatment of some diseases arising from tyrosinase activity disorders such as Parkinson’s disease, schizophrenia, autism, attention deficit, hyperactivity disorder, and cancer. Full article
(This article belongs to the Section Organic Synthesis)
Open AccessArticle Elaboration of Stable and Antibody Functionalized Positively Charged Colloids by Polyelectrolyte Complexation between Chitosan and Hyaluronic Acid
Molecules 2013, 18(7), 8563-8578; doi:10.3390/molecules18078563
Received: 23 May 2013 / Revised: 11 July 2013 / Accepted: 15 July 2013 / Published: 19 July 2013
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Abstract
In this study, we describe the elaboration of multifunctional positively charged polyelectrolyte complex (PEC) nanoparticles, designed to be stable at physiological salt concentration and pH, for effective targeted delivery. These nanoparticles were obtained by charge neutralization between chitosan (CS) as polycation and [...] Read more.
In this study, we describe the elaboration of multifunctional positively charged polyelectrolyte complex (PEC) nanoparticles, designed to be stable at physiological salt concentration and pH, for effective targeted delivery. These nanoparticles were obtained by charge neutralization between chitosan (CS) as polycation and hyaluronic acid (HA) as polyanion. We showed that the course of the complexation process and the physico-chemical properties of the resulting colloids were impacted by (i) internal parameters such as the Degree of Acetylation (DA, i.e., the molar ration of acetyl glucosamine residues) and molar mass of CS, the HA molar mass and (ii) external parameters like the charge mixing ratio and the polymer concentrations. As a result, nonstoichiometric colloidal PECs were obtained in water or PBS (pH 7.4) and remained stable over one month. The polymer interactions were characterized by thermal analysis (DSC and TGA) and the morphology was studied by scanning electron microscopy. A model antibody, anti-ovalbumine (OVA) immunoglobulin A (IgA) was sorbed on the particle surface in water and PBS quantitatively in 4 h. The CS-HA/IgA nanoparticles average size was between 425–665 nm with a positive zeta potential. These results pointed out that CS-HA can be effective carriers for use in targeted drug delivery. Full article
(This article belongs to the Special Issue Chitins and Chitosans)
Open AccessArticle Structure of the C-terminal Region of the Frizzled Receptor 1 in Detergent Micelles
Molecules 2013, 18(7), 8579-8590; doi:10.3390/molecules18078579
Received: 24 June 2013 / Revised: 18 July 2013 / Accepted: 18 July 2013 / Published: 22 July 2013
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Abstract
The C-terminal domains of the Frizzleds (FZDs) contain a short conserved motif (KTXXXW). It has been demonstrated that FZDs interacted with the PDZ domain of the cytoplasmic proteins such as Dishevelled through this motif and mutations in this motif disrupted Wnt/β-catenin signaling. [...] Read more.
The C-terminal domains of the Frizzleds (FZDs) contain a short conserved motif (KTXXXW). It has been demonstrated that FZDs interacted with the PDZ domain of the cytoplasmic proteins such as Dishevelled through this motif and mutations in this motif disrupted Wnt/β-catenin signaling. We carried out structural studies for a peptide derived from the C-terminal domain of the FZD1 in different solvents using circular dichroism and solution NMR spectroscopy. Our results showed that this domain was unstructured in an aqueous solution and formed a helical structure in detergent micelles. Fluorescence studies suggested that the tryptophan residue (W630) in the motif interacted with micelles. The solution structure of the peptide in sodium dodecyl sulfate micelles was determined and an amphipathic helix was identified. This helix may have similar function to the helix 8 of other G protein-coupled receptors. Full article
(This article belongs to the Special Issue NMR of Proteins and Small Biomolecules)
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Open AccessArticle Searching for Stable SinCn Clusters: Combination of Stochastic Potential Surface Search and Pseudopotential Plane-Wave Car-Parinello Simulated Annealing Simulations
Molecules 2013, 18(7), 8591-8606; doi:10.3390/molecules18078591
Received: 22 April 2013 / Revised: 11 July 2013 / Accepted: 16 July 2013 / Published: 22 July 2013
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Abstract
To find low energy SinCn structures out of hundreds to thousands of isomers we have developed a general method to search for stable isomeric structures that combines Stochastic Potential Surface Search and Pseudopotential Plane-Wave Density Functional Theory Car-Parinello Molecular [...] Read more.
To find low energy SinCn structures out of hundreds to thousands of isomers we have developed a general method to search for stable isomeric structures that combines Stochastic Potential Surface Search and Pseudopotential Plane-Wave Density Functional Theory Car-Parinello Molecular Dynamics simulated annealing (PSPW-CPMD-SA). We enhanced the Sunders stochastic search method to generate random cluster structures used as seed structures for PSPW-CPMD-SA simulations. This method ensures that each SA simulation samples a different potential surface region to find the regional minimum structure. By iterations of this automated, parallel process on a high performance computer we located hundreds to more than a thousand stable isomers for each SinCn cluster. Among these, five to 10 of the lowest energy isomers were further optimized using B3LYP/cc-pVTZ method. We applied this method to SinCn (n = 4–12) clusters and found the lowest energy structures, most not previously reported. By analyzing the bonding patterns of low energy structures of each SinCn cluster, we observed that carbon segregations tend to form condensed conjugated rings while Si connects to unsaturated bonds at the periphery of the carbon segregation as single atoms or clusters when n is small and when n is large a silicon network spans over the carbon segregation region. Full article
Open AccessArticle The Effect of PAMAM Dendrimers on the Antibacterial Activity of Antibiotics with Different Water Solubility
Molecules 2013, 18(7), 8607-8617; doi:10.3390/molecules18078607
Received: 20 June 2013 / Revised: 12 July 2013 / Accepted: 16 July 2013 / Published: 22 July 2013
Cited by 10 | PDF Full-text (226 KB) | HTML Full-text | XML Full-text
Abstract
Erythromycin (EM) and tobramycin (TOB) are well-known and widely used antibiotics, belonging to different therapeutic groups: macrolide and aminoglycoside, respectively. Moreover, they possess different solubility: EM is slightly soluble and TOB is freely soluble in water. It was previously demonstrated that PAMAM [...] Read more.
Erythromycin (EM) and tobramycin (TOB) are well-known and widely used antibiotics, belonging to different therapeutic groups: macrolide and aminoglycoside, respectively. Moreover, they possess different solubility: EM is slightly soluble and TOB is freely soluble in water. It was previously demonstrated that PAMAM dendrimers enhanced the pharmacological activity of antifungal drugs by increasing their solubility. Therefore, it appears interesting to investigate the effect of PAMAM-NH2 and PAMAM-OH dendrimers generation 2 (G2) and generation 3 (G3) on the antibacterial activity of antibiotics with different water solubility. In this study it was shown that the aqueous solubility of EM was significantly increased by PAMAM dendrimers (PAMAM-NH2 and PAMAM-OH caused about 8- and 7- fold solubility increases, respectively). However, it was indicated that despite the increase in the solubility, there was only slight influence on the antibacterial activity of EM (2- and 4- fold decreases in the MBC values of EM in the presence of PAMAM-OH G3 and PAMAM-NH2 G2 or G3 for strains of Staphylococcus aureus were noted, respectively). It was also found that there was no influence of PAMAM on the antibacterial activity of hydrophilic TOB. Full article
(This article belongs to the Special Issue Dendrimers in Medicine and Biotechnology)
Open AccessArticle Phenolic Content and Antioxidant Activities of Burr Parsley (Caucalis platycarpos L.)
Molecules 2013, 18(7), 8666-8681; doi:10.3390/molecules18078666
Received: 4 July 2013 / Revised: 17 July 2013 / Accepted: 17 July 2013 / Published: 22 July 2013
Cited by 1 | PDF Full-text (704 KB) | HTML Full-text | XML Full-text
Abstract
Since C. platycarpos contains a wide variety of antioxidants, in the present study total flavonoid and phenolic acid content as well as antioxidative activity of various C. platycarpos extracts were investigated. The results obtained show a significant polyphenol content and antioxidant activity [...] Read more.
Since C. platycarpos contains a wide variety of antioxidants, in the present study total flavonoid and phenolic acid content as well as antioxidative activity of various C. platycarpos extracts were investigated. The results obtained show a significant polyphenol content and antioxidant activity of the investigated plant. Moreover, a positive correlation between antioxidant activity and content of flavonoids and phenolic acids was found, indicating the responsibility of these compounds for the antioxidant effectiveness of C. platycarpos extracts and making C. platycarpos a good potential source of natural antioxidants. Full article
(This article belongs to the Section Natural Products)
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Open AccessArticle MYB Transcription Factors Regulate Glucosinolate Biosynthesis in Different Organs of Chinese Cabbage (Brassica rapa ssp. pekinensis)
Molecules 2013, 18(7), 8682-8695; doi:10.3390/molecules18078682
Received: 23 May 2013 / Revised: 11 July 2013 / Accepted: 18 July 2013 / Published: 22 July 2013
Cited by 10 | PDF Full-text (1110 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
In this study, we investigated the expression of seven MYB transcription factors (a total of 17 genes that included Dof1.1, IQD1-1, MYB28, MYB29, MYB34, MYB51, and MYB122 and their isoforms) involved in aliphatic and indolic glucosinolate (GSL) biosynthesis and analyzed the aliphatic [...] Read more.
In this study, we investigated the expression of seven MYB transcription factors (a total of 17 genes that included Dof1.1, IQD1-1, MYB28, MYB29, MYB34, MYB51, and MYB122 and their isoforms) involved in aliphatic and indolic glucosinolate (GSL) biosynthesis and analyzed the aliphatic and indolic GSL content in different organs of Chinese cabbage (Brassica rapassp. Pekinensis). MYB28 and MYB29 expression in the stem was dramatically different when compared with the levels in the other organs. MYB34, MYB122, MYB51, Dof1.1, and IQD1-1 showed very low transcript levels among different organs. HPLC analysis showed that the glucosinolates (GSLs) consisted of five aliphatic GSLs (progoitrin, sinigrin, glucoalyssin, gluconapin, and glucobrassicanapin) and four indolic GSLs (4-hydroxyglucobrassicin, glucobrassicin, 4-methoxygluco-brassicin, and neoglucobrassicin). Aliphatic GSLs exhibited 63.3% of the total GSLs content, followed by aromatic GSL (19.0%), indolic GSLs (10%), and unknown GSLs (7.7%) in different organs of Chinese cabbage. The total GSL content of different parts (ranked in descending order) was as follows: seed > flower > young leaves > stem > root > old leaves. The relationship between GSLs accumulation and expression of GSLs biosynthesis MYB TFs genes in different organs may be helpful to understand the mechanism of MYB TFs regulating GSL biosynthesis in Chinese cabbage. Full article
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Open AccessArticle Diorganotin(IV) Derivatives of N-Methyl p-Fluorobenzo-Hydroxamic Acid: Preparation, Spectral Characterization, X-ray Diffraction Studies and Antitumor Activity
Molecules 2013, 18(7), 8696-8711; doi:10.3390/molecules18078696
Received: 23 May 2013 / Revised: 15 July 2013 / Accepted: 16 July 2013 / Published: 22 July 2013
Cited by 5 | PDF Full-text (590 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Three diorganotin(IV) complexes of the general formula R2Sn[RcC(O)N(RN)O] (Rc = aryl, RN = Alkyl) have been synthesized by refluxing in toluene the corresponding diorganotin(IV) oxides with the free ligand N-methyl p-fluorobenzohydroxamic [...] Read more.
Three diorganotin(IV) complexes of the general formula R2Sn[RcC(O)N(RN)O] (Rc = aryl, RN = Alkyl) have been synthesized by refluxing in toluene the corresponding diorganotin(IV) oxides with the free ligand N-methyl p-fluorobenzohydroxamic acid, using a Dean and Stark water separator. The ligand was derived from the reaction of the corresponding p-fluorobenzoyl chloride and N-methylhydroxylamine hydrochloride in the presence of sodium hydrogen carbonate. The isolated free ligand and its respective diorganotin compounds have been characterized by elemental analysis, IR and 1H-, 13C-, 119Sn-NMR spectroscopies. The crystal structures of the diorganotin complexes have been confirmed by single crystal X-ray diffraction methods. The investigations carried out on the diorganotin(IV) complexes of N-methyl p-fluorobenzohydroxamic acid confirmed a 1:2 stoichiometry. The complex formation took place through the O,O-coordination via the carbonyl oxygen and subsequent deprotonated hydroxyl group to the tin atom. The crystal structures of three diorganotin complexes were determined and were found to adopt six coordination geometries at the tin centre with coordination to two ligand moieties. Full article

Review

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Open AccessReview Modulation of Xenobiotic Receptors by Steroids
Molecules 2013, 18(7), 7389-7406; doi:10.3390/molecules18077389
Received: 24 May 2013 / Revised: 13 June 2013 / Accepted: 19 June 2013 / Published: 24 June 2013
Cited by 8 | PDF Full-text (1081 KB) | HTML Full-text | XML Full-text
Abstract
Nuclear receptors (NRs) are ligand-activated transcription factors that regulate the expression of their target genes. NRs play important roles in many human diseases, including metabolic diseases and cancer, and are therefore a key class of therapeutic targets. Steroids play important roles in [...] Read more.
Nuclear receptors (NRs) are ligand-activated transcription factors that regulate the expression of their target genes. NRs play important roles in many human diseases, including metabolic diseases and cancer, and are therefore a key class of therapeutic targets. Steroids play important roles in regulating nuclear receptors; in addition to being ligands of steroid receptors, steroids (and their metabolites) also regulate other NRs, such as the pregnane X receptor and constitutive androstane receptor (termed xenobiotic receptors), which participate in steroid metabolism. Xenobiotic receptors have promiscuous ligand-binding properties, and their structurally diverse ligands include steroids and their metabolites. Therefore, steroids, their metabolism and metabolites, xenobiotic receptors, steroid receptors, and the respective signaling pathways they regulate have functional interactions. This review discusses these functional interactions and their implications for activities mediated by steroid receptors and xenobiotic receptors, focusing on steroids that modulate pathways involving the pregnane X receptor and constitutive androstane receptor. The emphasis of the review is on structure-function studies of xenobiotic receptors bound to steroid ligands. Full article
(This article belongs to the Special Issue Steroids)
Open AccessReview Solution NMR Studies on the Orientation of Membrane-Bound Peptides and Proteins by Paramagnetic Probes
Molecules 2013, 18(7), 7407-7435; doi:10.3390/molecules18077407
Received: 26 April 2013 / Revised: 13 June 2013 / Accepted: 20 June 2013 / Published: 25 June 2013
Cited by 6 | PDF Full-text (1186 KB) | HTML Full-text | XML Full-text
Abstract
Many peptides and proteins are attached to or immersed in a biological membrane. In order to understand their function not only the structure but also their topology in the membrane is important. Solution NMR spectroscopy is one of the most often used [...] Read more.
Many peptides and proteins are attached to or immersed in a biological membrane. In order to understand their function not only the structure but also their topology in the membrane is important. Solution NMR spectroscopy is one of the most often used approaches to determine the orientation and localization of membrane-bound peptides and proteins. Here we give an application-oriented overview on the use of paramagnetic probes for the investigation of membrane-bound peptides and proteins. The examples discussed range from the large pool of antimicrobial peptides, bacterial toxins, cell penetrating peptides to domains of larger proteins or the calcium regulating protein phospholamban. Topological information is obtained in all these examples by the use of either attached or freely mobile paramagnetic tags. For some examples information obtained from the paramagnetic probes was included in the structure determination. Full article
(This article belongs to the Special Issue NMR of Proteins and Small Biomolecules)
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Open AccessReview Hepatoprotective Effects of Mushrooms
Molecules 2013, 18(7), 7609-7630; doi:10.3390/molecules18077609
Received: 27 May 2013 / Revised: 26 June 2013 / Accepted: 27 June 2013 / Published: 1 July 2013
Cited by 17 | PDF Full-text (1027 KB) | HTML Full-text | XML Full-text
Abstract
The particular characteristics of growth and development of mushrooms in nature result in the accumulation of a variety of secondary metabolites such as phenolic compounds, terpenes and steroids and essential cell wall components such as polysaccharides, b-glucans and proteins, several of them [...] Read more.
The particular characteristics of growth and development of mushrooms in nature result in the accumulation of a variety of secondary metabolites such as phenolic compounds, terpenes and steroids and essential cell wall components such as polysaccharides, b-glucans and proteins, several of them with biological activities. The present article outlines and discusses the available information about the protective effects of mushroom extracts against liver damage induced by exogenous compounds. Among mushrooms, Ganoderma lucidum is indubitably the most widely studied species. In this review, however, emphasis was given to studies using other mushrooms, especially those presenting efforts of attributing hepatoprotective activities to specific chemical components usually present in the mushroom extracts. Full article
(This article belongs to the Section Medicinal Chemistry)
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Open AccessReview Triterpenoids of Marine Origin as Anti-Cancer Agents
Molecules 2013, 18(7), 7886-7909; doi:10.3390/molecules18077886
Received: 16 February 2013 / Revised: 10 June 2013 / Accepted: 27 June 2013 / Published: 4 July 2013
Cited by 12 | PDF Full-text (1645 KB) | HTML Full-text | XML Full-text
Abstract
Triterpenoids are the most abundant secondary metabolites present in marine organisms, such as marine sponges, sea cucumbers, marine algae and marine-derived fungi. A large number of triterpenoids are known to exhibit cytotoxicity against a variety of tumor cells, as well as anticancer [...] Read more.
Triterpenoids are the most abundant secondary metabolites present in marine organisms, such as marine sponges, sea cucumbers, marine algae and marine-derived fungi. A large number of triterpenoids are known to exhibit cytotoxicity against a variety of tumor cells, as well as anticancer efficacy in preclinical animal models. In this review efforts have been taken to review the structural features and the potential use of triterpenoids of marine origin to be used in the pharmaceutical industry as potential anti-cancer drug leads. Full article
(This article belongs to the Special Issue Triterpenes and Triterpenoids)
Open AccessReview Dendrimers as Potential Therapeutic Tools in HIV Inhibition
Molecules 2013, 18(7), 7912-7929; doi:10.3390/molecules18077912
Received: 18 June 2013 / Revised: 25 June 2013 / Accepted: 26 June 2013 / Published: 5 July 2013
Cited by 6 | PDF Full-text (458 KB) | HTML Full-text | XML Full-text
Abstract
The present treatments for HIV transfection include chemical agents and gene therapies. Although many chemical drugs, peptides and genes have been developed for HIV inhibition, a variety of non-ignorable drawbacks limited the efficiency of these materials. In this review, we discuss the [...] Read more.
The present treatments for HIV transfection include chemical agents and gene therapies. Although many chemical drugs, peptides and genes have been developed for HIV inhibition, a variety of non-ignorable drawbacks limited the efficiency of these materials. In this review, we discuss the application of dendrimers as both therapeutic agents and non-viral vectors of chemical agents and genes for HIV treatment. On the one hand, dendrimers with functional end groups combine with the gp120 of HIV and CD4 molecule of host cell to suppress the attachment of HIV to the host cell. Some of the dendrimers are capable of intruding into the cell and interfere with the later stages of HIV replication as well. On the other hand, dendrimers are also able to transfer chemical drugs and genes into the host cells, which conspicuously increase the anti-HIV activity of these materials. Dendrimers as therapeutic tools provide a potential treatment for HIV infection. Full article
(This article belongs to the Special Issue Dendrimers in Medicine and Biotechnology)
Open AccessReview Microfluidics: A Groundbreaking Technology for PET Tracer Production?
Molecules 2013, 18(7), 7930-7956; doi:10.3390/molecules18077930
Received: 3 June 2013 / Revised: 21 June 2013 / Accepted: 3 July 2013 / Published: 5 July 2013
Cited by 18 | PDF Full-text (583 KB) | HTML Full-text | XML Full-text
Abstract
Application of microfluidics to Positron Emission Tomography (PET) tracer synthesis has attracted increasing interest within the last decade. The technical advantages of microfluidics, in particular the high surface to volume ratio and resulting fast thermal heating and cooling rates of reagents can [...] Read more.
Application of microfluidics to Positron Emission Tomography (PET) tracer synthesis has attracted increasing interest within the last decade. The technical advantages of microfluidics, in particular the high surface to volume ratio and resulting fast thermal heating and cooling rates of reagents can lead to reduced reaction times, increased synthesis yields and reduced by-products. In addition automated reaction optimization, reduced consumption of expensive reagents and a path towards a reduced system footprint have been successfully demonstrated. The processing of radioactivity levels required for routine production, use of microfluidic-produced PET tracer doses in preclinical and clinical imaging as well as feasibility studies on autoradiolytic decomposition have all given promising results. However, the number of microfluidic synthesizers utilized for commercial routine production of PET tracers is very limited. This study reviews the state of the art in microfluidic PET tracer synthesis, highlighting critical design aspects, strengths, weaknesses and presenting several characteristics of the diverse PET market space which are thought to have a significant impact on research, development and engineering of microfluidic devices in this field. Furthermore, the topics of batch- and single-dose production, cyclotron to quality control integration as well as centralized versus de-centralized market distribution models are addressed. Full article
(This article belongs to the Special Issue PET Chemistry in Molecular Imaging)
Open AccessReview Advances in Fruit Aroma Volatile Research
Molecules 2013, 18(7), 8200-8229; doi:10.3390/molecules18078200
Received: 17 May 2013 / Revised: 2 July 2013 / Accepted: 3 July 2013 / Published: 11 July 2013
Cited by 35 | PDF Full-text (710 KB) | HTML Full-text | XML Full-text
Abstract
Fruits produce a range of volatile compounds that make up their characteristic aromas and contribute to their flavor. Fruit volatile compounds are mainly comprised of esters, alcohols, aldehydes, ketones, lactones, terpenoids and apocarotenoids. Many factors affect volatile composition, including the genetic makeup, [...] Read more.
Fruits produce a range of volatile compounds that make up their characteristic aromas and contribute to their flavor. Fruit volatile compounds are mainly comprised of esters, alcohols, aldehydes, ketones, lactones, terpenoids and apocarotenoids. Many factors affect volatile composition, including the genetic makeup, degree of maturity, environmental conditions, postharvest handling and storage. There are several pathways involved in volatile biosynthesis starting from lipids, amino acids, terpenoids and carotenoids. Once the basic skeletons are produced via these pathways, the diversity of volatiles is achieved via additional modification reactions such as acylation, methylation, oxidation/reduction and cyclic ring closure. In this paper, we review the composition of fruit aroma, the characteristic aroma compounds of several representative fruits, the factors affecting aroma volatile, and the biosynthetic pathways of volatile aroma compounds. We anticipate that this review would provide some critical information for profound research on fruit aroma components and their manipulation during development and storage. Full article
(This article belongs to the Special Issue Flavors and Fragrances)
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Open AccessReview The Application of Transient-State Kinetic Isotope Effects to the Resolution of Mechanisms of Enzyme-Catalyzed Reactions
Molecules 2013, 18(7), 8230-8242; doi:10.3390/molecules18078230
Received: 12 May 2013 / Revised: 19 June 2013 / Accepted: 1 July 2013 / Published: 12 July 2013
Cited by 2 | PDF Full-text (1113 KB) | HTML Full-text | XML Full-text
Abstract
Much of our understanding of the mechanisms of enzyme-catalyzed reactions is based on steady-state kinetic studies. Experimentally, this approach depends solely on the measurement of rates of free product appearance (d[P]/dt), a mechanistically and mathematically complex entity. Despite the ambiguity [...] Read more.
Much of our understanding of the mechanisms of enzyme-catalyzed reactions is based on steady-state kinetic studies. Experimentally, this approach depends solely on the measurement of rates of free product appearance (d[P]/dt), a mechanistically and mathematically complex entity. Despite the ambiguity of this observed parameter, the method’s success is due in part to the elaborate rigorously derived algebraic theory on which it is based. Transient-state kinetics, on the other hand, despite its ability to observe the formation of intermediate steps in real time, has contributed relatively little to the subject due in, some measure, to the lack of such a solid mathematical basis. Here we discuss the current state of existing transient-state theory and the difficulties in its realistic application to experimental data. We describe a basic analytic theory of transient-state kinetic isotope effects in the form of three novel fundamental rules. These rules are adequate to define an extended mechanism, locating the isotope-sensitive step and identifying missing steps from experimental data. We demonstrate the application of these rules to resolved component time courses of the phenylalanine dehydrogenase reaction, extending the previously known reaction by one new prehydride transfer step and two new post hydride transfer steps. We conclude with an assessment of future directions in this area. Full article
(This article belongs to the Special Issue Isotope Effects)
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Open AccessReview The Pharmacological Activities of (−)-Anonaine
Molecules 2013, 18(7), 8257-8263; doi:10.3390/molecules18078257
Received: 13 May 2013 / Revised: 28 June 2013 / Accepted: 3 July 2013 / Published: 12 July 2013
Cited by 4 | PDF Full-text (193 KB)
Abstract
Several species of Magnoliaceae and Annonaceae are used in Traditional Chinese Medicine. (−)-Anonaine, isolated from several species of Magnoliaceae and Annonaceae, presents antiplasmodial, antibacterial, antifungal, antioxidation, anticancer, antidepression, and vasorelaxant activity. This article provides an overview of the pharmacological functions of (−)-anonaine. [...] Read more.
Several species of Magnoliaceae and Annonaceae are used in Traditional Chinese Medicine. (−)-Anonaine, isolated from several species of Magnoliaceae and Annonaceae, presents antiplasmodial, antibacterial, antifungal, antioxidation, anticancer, antidepression, and vasorelaxant activity. This article provides an overview of the pharmacological functions of (−)-anonaine. Full article
(This article belongs to the Special Issue Alkaloids: Novel Therapeutic Perspectives)
Open AccessReview The Genus Gnaphalium L. (Compositae): Phytochemical and Pharmacological Characteristics
Molecules 2013, 18(7), 8298-8318; doi:10.3390/molecules18078298
Received: 18 June 2013 / Revised: 8 July 2013 / Accepted: 12 July 2013 / Published: 15 July 2013
Cited by 3 | PDF Full-text (319 KB) | HTML Full-text | XML Full-text
Abstract
The genus Gnaphalium, a herb distributed worldwide, comprises approximately 200 species of the Compositae (Asteraceae) family that belongs to the tribe Gnaphalieae. Some species are traditionally used as wild vegetables and in folk medicine. This review focuses on the phytochemical investigations [...] Read more.
The genus Gnaphalium, a herb distributed worldwide, comprises approximately 200 species of the Compositae (Asteraceae) family that belongs to the tribe Gnaphalieae. Some species are traditionally used as wild vegetables and in folk medicine. This review focuses on the phytochemical investigations and biological studies of plants from the genus Gnaphalium over the past few decades. More than 125 chemical constituents have been isolated from the genus Gnaphalium, including flavonoids, sesquiterpenes, diterpenes, triterpenes, phytosterols, anthraquinones, caffeoylquinic acid derivatives, and other compounds. The extracts of this genus, as well as compounds isolated from it, have been demonstrated to possess multiple pharmacological activities such as antioxidant, antibacterial and antifungal, anti-complement, antitussive and expectorant, insect antifeedant, cytotoxic, anti-inflammatory, antidiabetic and antihypouricemic properties. The present review compiles the information available on this genus because of its relevance to food and ethnopharmacology and the potential therapeutic uses of these species. Full article
Open AccessReview Dendrimers in Layer-by-Layer Assemblies: Synthesis and Applications
Molecules 2013, 18(7), 8440-8460; doi:10.3390/molecules18078440
Received: 27 June 2013 / Revised: 8 July 2013 / Accepted: 15 July 2013 / Published: 17 July 2013
Cited by 23 | PDF Full-text (587 KB) | HTML Full-text | XML Full-text
Abstract
We review the synthesis of dendrimer-containing layer-by-layer (LbL) assemblies and their applications, including biosensing, controlled drug release, and bio-imaging. Dendrimers can be built into LbL films and microcapsules by alternating deposition of dendrimers and counter polymers on the surface of flat substrates [...] Read more.
We review the synthesis of dendrimer-containing layer-by-layer (LbL) assemblies and their applications, including biosensing, controlled drug release, and bio-imaging. Dendrimers can be built into LbL films and microcapsules by alternating deposition of dendrimers and counter polymers on the surface of flat substrates and colloidal microparticles through electrostatic bonding, hydrogen bonding, covalent bonding, and biological affinity. Dendrimer-containing LbL assemblies have been used to construct biosensors, in which electron transfer mediators and metal nanoparticles are often coupled with dendrimers. Enzymes have been successfully immobilized on the surface of electrochemical and optical transducers by forming enzyme/dendrimer LbL multilayers. In this way, high-performance enzyme sensors are fabricated. In addition, dendrimer LbL films and microcapsules are useful for constructing drug delivery systems because dendrimers bind drugs to form inclusion complexes or the dendrimer surface is covalently modified with drugs. Magnetic resonance imaging of cancer cells by iron oxide nanoparticles coated with dendrimer LbL film is also discussed. Full article
(This article belongs to the Special Issue Dendrimers in Medicine and Biotechnology)
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Open AccessReview Recent Trends in Bioorthogonal Click-Radiolabeling Reactions Using Fluorine-18
Molecules 2013, 18(7), 8618-8665; doi:10.3390/molecules18078618
Received: 13 June 2013 / Revised: 11 July 2013 / Accepted: 15 July 2013 / Published: 22 July 2013
Cited by 23 | PDF Full-text (866 KB) | HTML Full-text | XML Full-text
Abstract
The increasing application of positron emission tomography (PET) in nuclear medicine has stimulated the extensive development of a multitude of novel and versatile bioorthogonal conjugation techniques especially for the radiolabeling of biologically active high molecular weight compounds like peptides, proteins or antibodies. [...] Read more.
The increasing application of positron emission tomography (PET) in nuclear medicine has stimulated the extensive development of a multitude of novel and versatile bioorthogonal conjugation techniques especially for the radiolabeling of biologically active high molecular weight compounds like peptides, proteins or antibodies. Taking into consideration that the introduction of fluorine-18 (t1/2 = 109.8 min) proceeds under harsh conditions, radiolabeling of these biologically active molecules represents an outstanding challenge and is of enormous interest. Special attention has to be paid to the method of 18F-introduction. It should proceed in a regioselective manner under mild physiological conditions, in an acceptable time span, with high yields and high specific activities. For these reasons and due to the high number of functional groups found in these compounds, a specific labeling procedure has to be developed for every bioactive macromolecule. Bioorthogonal strategies including the Cu-assisted Huisgen cycloaddition and its copper-free click variant, both Staudinger Ligations or the tetrazine-click reaction have been successfully applied and represent valuable alternatives for the selective introduction of fluorine-18 to overcome the afore mentioned obstacles. This comprehensive review deals with the progress and illustrates the latest developments in the field of bioorthogonal labeling with the focus on the preparation of radiofluorinated building blocks and tracers for molecular imaging. Full article
(This article belongs to the Special Issue Advances in Click Chemistry)

Other

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Open AccessRetraction Retraction: Hashim, H. et al., Cytoprotective Effect of Benzyl N'-(5-Chloro-indol-3-yl-methylidene)hydrazinecarbodithioate against Ethanol-induced Gastric Mucosal Injury in Rats. Molecules 2012, 17, 9306-9320
Molecules 2013, 18(7), 7910-7911; doi:10.3390/molecules18077910
Received: 26 June 2013 / Revised: 28 June 2013 / Accepted: 28 June 2013 / Published: 5 July 2013
PDF Full-text (108 KB) | HTML Full-text | XML Full-text
Abstract
I have been made aware of that fact that substantial parts of our paper published in Molecules [1] duplicate the contents of another paper previously published under our names in African Journal of Pure and Applied Chemistry [2] of which existence I [...] Read more.
I have been made aware of that fact that substantial parts of our paper published in Molecules [1] duplicate the contents of another paper previously published under our names in African Journal of Pure and Applied Chemistry [2] of which existence I was unaware. Although the compounds reported in both papers are different, I was not aware of the same biological data being used in the earlier publication. The article in Molecules was submitted in good faith based on the collective work that was presented to me by our co-author Dr Mughrabi, listed as the corresponding author of the article published in African Journal of Pure and Applied Chemistry [2]. Full article

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