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Molecules, Volume 17, Issue 1 (January 2012), Pages 1-1137

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Open AccessArticle Facile Preparation of the Tosylhydrazone Derivatives of a Series of Racemic trans-3,4-Substituted Cyclopentanones
Molecules 2012, 17(1), 1-14; doi:10.3390/molecules17010001
Received: 14 November 2011 / Revised: 19 December 2011 / Accepted: 19 December 2011 / Published: 22 December 2011
Cited by 9 | PDF Full-text (206 KB)
Abstract
We report the synthesis and characterization of a variety of trans-3,4-substituted cyclopentanones and the corresponding tosylhydrazone derivatives starting with diethyl fumarate. Protection of the keto group followed by selective monohydrolysis of esters was achieved, resulting in cyclopentanones with different substituents at [...] Read more.
We report the synthesis and characterization of a variety of trans-3,4-substituted cyclopentanones and the corresponding tosylhydrazone derivatives starting with diethyl fumarate. Protection of the keto group followed by selective monohydrolysis of esters was achieved, resulting in cyclopentanones with different substituents at positions 3 and 4. The tosylhydrazone derivative of each cyclopentanone intermediate was prepared in moderate to good yields. These compounds are potential precursors for functionalized methanofullerenes. Full article
(This article belongs to the Section Organic Synthesis)
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Open AccessArticle HPLC Analysis of Supercritical Carbon Dioxide and Compressed Propane Extracts from Piper amalago L. with Antileishmanial Activity
Molecules 2012, 17(1), 15-33; doi:10.3390/molecules17010015
Received: 2 October 2011 / Revised: 5 December 2011 / Accepted: 14 December 2011 / Published: 22 December 2011
Cited by 10 | PDF Full-text (306 KB)
Abstract
Piper amalago L. leaves were extracted with supercritical carbon dioxide and compressed propane under different conditions, and with chloroform by the conventional maceration method. These methods were compared for the pyrrolidine alkaloid content. Supercritical carbon dioxide (SFE-CO2) at 313 K [...] Read more.
Piper amalago L. leaves were extracted with supercritical carbon dioxide and compressed propane under different conditions, and with chloroform by the conventional maceration method. These methods were compared for the pyrrolidine alkaloid content. Supercritical carbon dioxide (SFE-CO2) at 313 K and 12.55 MPa showed the highest selectivity for the main compound (600.53 mg/g of extract). A gradient high-performance liquid chromatography (HPLC) method was developed and validated to quantify the alkaloid N-[7-(3′,4′-methylenedioxyphenyl)-2(Z),4(Z)-heptadienoyl]pyrrolidine (1) in the extracts. The HPLC method showed linearity, precision and accuracy, allowing the quantitative analysis of the alkaloid in all the samples. All the extracts were tested against the promastigote and intracellular amastigote forms of Leishmania amazonensis. The antileishmanial activity was evaluated in terms of inhibitory concentration for 50% of protozoa (IC50). The cytotoxicity was also evaluated against J774A1 macrophages, and the cytotoxic concentrations for 50% of macrophages were obtained (CC50). The SFE-CO2 (313 K; 12.55 MPa) extract showed the highest antileishmanial activity with the following IC50 values of 16 and 7 µg/mL against the promastigotes and intracellular amastigotes forms, respectively. The extract showed low cytotoxicity with a CC50 value of 93 µg/mL. Full article
(This article belongs to the Section Natural Products)
Open AccessArticle Hybridization vs. Bond Stretching Isomerism in Ru(II) Cyclometalated Complexes of 2-Phenylpyridine
Molecules 2012, 17(1), 34-47; doi:10.3390/molecules17010034
Received: 11 October 2011 / Revised: 10 December 2011 / Accepted: 13 December 2011 / Published: 22 December 2011
Cited by 2 | PDF Full-text (300 KB)
Abstract
The phenomenon of formation of two isomers, yellow and orange, of the cyclometalated Ru(II) complex, [Ru(o-C6H4-py)(MeCN)4]+, was investigated by EELS spectroscopy and theoretical calculations. Both forms show very similar structures and spectroscopic [...] Read more.
The phenomenon of formation of two isomers, yellow and orange, of the cyclometalated Ru(II) complex, [Ru(o-C6H4-py)(MeCN)4]+, was investigated by EELS spectroscopy and theoretical calculations. Both forms show very similar structures and spectroscopic properties, but slight differences in X-ray data and absorption between them were noted. No double minimum on the potential energy surface was found and thus these two forms cannot be considered as bond stretching isomers. However, the DFT study revealed the change in the hybridization of the carbon in trans-position of one of acetonitrile ligands. This effect can be responsible for the difference in colour. The results of the theoretical modelling coincide well with the experimental EELS data. Full article
Open AccessArticle Influence of Halogen Substituents on the Catalytic Oxidation of 2,4,6-Halogenated Phenols by Fe(III)-Tetrakis(p-hydroxyphenyl) porphyrins and Potassium Monopersulfate
Molecules 2012, 17(1), 48-60; doi:10.3390/molecules17010048
Received: 29 November 2011 / Revised: 17 December 2011 / Accepted: 19 December 2011 / Published: 22 December 2011
Cited by 13 | PDF Full-text (421 KB)
Abstract
The influence of halogen substituents on the catalytic oxidation of 2,4,6-trihalogenated phenols (TrXPs) by iron(III)-porphyrin/KHSO5 catalytic systems was investigated. Iron(III)-5,10,15,20-tetrakis(p-hydroxyphenyl)porphyrin (FeTHP) and its supported variants were employed, where the supported catalysts were synthesized by introducing FeTHP into hydroquinone-derived humic [...] Read more.
The influence of halogen substituents on the catalytic oxidation of 2,4,6-trihalogenated phenols (TrXPs) by iron(III)-porphyrin/KHSO5 catalytic systems was investigated. Iron(III)-5,10,15,20-tetrakis(p-hydroxyphenyl)porphyrin (FeTHP) and its supported variants were employed, where the supported catalysts were synthesized by introducing FeTHP into hydroquinone-derived humic acids via formaldehyde poly-condensation. F (TrFP), Cl (TrCP), Br (TrBP) and I (TrIP) were examined as halogen substituents for TrXPs. Although the supported catalysts significantly enhanced the degradation and dehalogenation of TrFP and TrCP, the oxidation of TrBP and TrIP was not enhanced, compared to the FeTHP catalytic system. These results indicate that the degree of oxidation of TrXPs is strongly dependent on the types of halogen substituent. The order of dehalogenation levels for halogen substituents in TrXPs was F > Cl > Br > I, consistent with their order of electronegativity. The electronegativity of a halogen substituent affects the nucleophilicity of the carbon to which it is attached. The levels of oxidation products in the reaction mixtures were analyzed by GC/MS after extraction with n-hexane. The most abundant dimer product from TrFP via 2,6-difluoroquinone is consistent with a scenario where TrXP, with a more electronegative halogen substituent, is readily oxidized, while less electronegative halogen substituents are oxidized less readily by iron(III)-porphyrin/KHSO5 catalytic systems. Full article
(This article belongs to the Special Issue Tetrapyrroles, Porphyrins and Phthalocyanines)
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Open AccessArticle Extract of Lillium candidum L. Can Modulate the Genotoxicity of the Antibiotic Zeocin
Molecules 2012, 17(1), 80-97; doi:10.3390/molecules17010080
Received: 31 October 2011 / Revised: 28 November 2011 / Accepted: 12 December 2011 / Published: 22 December 2011
Cited by 6 | PDF Full-text (408 KB)
Abstract
Lilium candidum L. extract (LE) is well known in folk medicine for the treatment of burns, ulcers, inflammations and for healing wounds. This work aims to clarify whether the genotoxic potential of the radiomimetic antibiotic zeocin (Zeo) could be modulated by LE. [...] Read more.
Lilium candidum L. extract (LE) is well known in folk medicine for the treatment of burns, ulcers, inflammations and for healing wounds. This work aims to clarify whether the genotoxic potential of the radiomimetic antibiotic zeocin (Zeo) could be modulated by LE. Our results indicate that LE exerts no cytotoxic, DNA-damaging and clastogenic activity in in Chlamydomonas reinhardtii, Pisum sativum L. and Hordeum vulgare L. test systems over a broad concentration range. Weak but statistically significant clastogenic effects due to the induction of micronuclei and chromosome aberrations have been observed in H. vulgare L. after treatment with 200 and 300 μg/mL LE. To discriminate protective from adverse action of LE different experimental designs have been used. Our results demonstrate that the treatment with mixtures of LE and Zeo causes an increase in the level of DNA damage, micronuclei and “metaphases with chromatid aberrations” (MwA). Clear evidence has been also obtained indicating that pretreatment with LE given 4 h before the treatment with Zeo accelerates the rejoining kinetics of Zeo-induced DNA damage in P. sativum L. and C. reinhardtii, and can decrease clastogenic effect of Zeo measured as frequencies of micronuclei and MwA in H. vulgare L. Here, we show for the first time that LE can modulate the genotoxic effects of zeocin. The molecular mode of action strongly depends on the experimental design and varies from synergistic to protective effect (adaptive response–AR). Our results also revealed that LE-induced AR to zeocin involves up-regulation of DSB rejoining in C. reinhardtii and P. sativum L. cells. Full article
Open AccessCommunication The Biological Response of Spermidine Induced by Ionization Radiation
Molecules 2012, 17(1), 145-150; doi:10.3390/molecules17010145
Received: 14 November 2011 / Revised: 20 December 2011 / Accepted: 21 December 2011 / Published: 23 December 2011
Cited by 5 | PDF Full-text (266 KB)
Abstract
Globally, there are concerns over the risks associated with radiation exposure, so it is important to understand the biological effects of radiation exposure. Driven by the need to detect the presence of radiation exposure, biomarkers to monitor potential exposure after radiological accidents [...] Read more.
Globally, there are concerns over the risks associated with radiation exposure, so it is important to understand the biological effects of radiation exposure. Driven by the need to detect the presence of radiation exposure, biomarkers to monitor potential exposure after radiological accidents can be developed and would be extremely valuable for biological response. In this study, the behavior of spermidine as a biomarker was investigated in a C57BL/6 mouse model exposed to an acute whole-body sublethal dose of 6 Gy. The spermidine content values in serum increased for up to two days after 6 Gy irradiation. However, the enhanced spermidine content observed on day +3 in irradiated mice returned to normal levels on the subsequent five days. The result indicates that spermidine can be used as a biomarker of biological response to radiation exposure. Full article
(This article belongs to the Section Molecular Diversity)
Open AccessArticle Synthesis of cis- and trans-3-Aminocyclohexanols by Reduction of β-Enaminoketones
Molecules 2012, 17(1), 151-162; doi:10.3390/molecules17010151
Received: 25 October 2011 / Revised: 21 December 2011 / Accepted: 22 December 2011 / Published: 27 December 2011
Cited by 2 | PDF Full-text (337 KB)
Abstract We describe a protocol developed for the preparation of β-enaminoketones derived from 1,3-cyclohexanediones, and their subsequent reduction by sodium in THF-isopropyl alcohol to afford cis- and trans-3-aminocyclohexanols. Full article
(This article belongs to the Section Organic Synthesis)
Open AccessArticle Template Directed Reversible Photochemical Ligation of Oligodeoxynucleotides
Molecules 2012, 17(1), 163-178; doi:10.3390/molecules17010163
Received: 29 November 2011 / Revised: 21 December 2011 / Accepted: 22 December 2011 / Published: 27 December 2011
Cited by 5 | PDF Full-text (887 KB)
Abstract
We demonstrated that 5-vinyldeoxyuridine (VU) and 5-carboxyvinyldeoxyuridine (CVU) can be used to photoligate a longer oligonucleotide (ODN) from smaller ODNs on a template. By performing irradiation at 366 nm, these artificial nucleotides make photoligated ODNs with high efficiency [...] Read more.
We demonstrated that 5-vinyldeoxyuridine (VU) and 5-carboxyvinyldeoxyuridine (CVU) can be used to photoligate a longer oligonucleotide (ODN) from smaller ODNs on a template. By performing irradiation at 366 nm, these artificial nucleotides make photoligated ODNs with high efficiency without any side reactions. Moreover, by performing irradiation at 312 nm, these photoligated ODNs were reversed to the original ODN. VU needs to be irradiated 366 nm for 6 h, but CVU needs to be irradiated at 366 nm for 15 min. Finally, we made a self-assembled structure with an ODN containing CVU and observed the photoligated ODN by photoirradiation. Full article
(This article belongs to the Special Issue DNA-Templated Synthesis)
Open AccessArticle Synthesis of 1,4-Disubstituted Mono and Bis-triazolocarbo-acyclonucleoside Analogues of 9-(4-Hydroxybutyl)guanine by Cu(I)-Catalyzed Click Azide-Alkyne Cycloaddition
Molecules 2012, 17(1), 179-190; doi:10.3390/molecules17010179
Received: 16 November 2011 / Revised: 9 December 2011 / Accepted: 19 December 2011 / Published: 27 December 2011
Cited by 9 | PDF Full-text (187 KB)
Abstract
A series of novel mono-1,2,3-triazole and bis-1,2,3-triazole acyclonucleoside analogues of 9-(4-hydroxybutyl)guanine was prepared via copper(I)-catalyzed 1,3-dipolar cycloaddition of N-9 propargylpurine, N-1-propargylpyrimidines/as-triazine with the azido-pseudo-sugar 4-azidobutylacetate under solvent-free microwave conditions, followed by treatment with K2CO3/MeOH, or NH [...] Read more.
A series of novel mono-1,2,3-triazole and bis-1,2,3-triazole acyclonucleoside analogues of 9-(4-hydroxybutyl)guanine was prepared via copper(I)-catalyzed 1,3-dipolar cycloaddition of N-9 propargylpurine, N-1-propargylpyrimidines/as-triazine with the azido-pseudo-sugar 4-azidobutylacetate under solvent-free microwave conditions, followed by treatment with K2CO3/MeOH, or NH3/MeOH. All compounds studied in this work were screened for their antiviral activities [against human rhinovirus (HRV) and hepatitis C virus (HCV)] and antibacterial activities against a series of Gram positive and negative bacteria. Full article
(This article belongs to the Section Medicinal Chemistry)
Open AccessArticle Molecular Properties of Water-Unextractable Proteoglycans from Hypsizygus marmoreus and Their in Vitro Immunomodulatory Activities
Molecules 2012, 17(1), 207-226; doi:10.3390/molecules17010207
Received: 27 October 2011 / Revised: 7 December 2011 / Accepted: 22 December 2011 / Published: 27 December 2011
Cited by 2 | PDF Full-text (1153 KB)
Abstract
Four proteoglycans were sequentially extracted from Hypsizygus marmoreus using 0.1 M NaOH (alkali-soluble proteoglycans [F1] and alkali-insoluble proteoglycans [F3]) and 0.1 M HCl (acid-soluble proteoglycans [F2] and acid-insoluble proteoglycans [F4]), and their structures and immunomodulatory activities were investigated. The proteoglycans were [...] Read more.
Four proteoglycans were sequentially extracted from Hypsizygus marmoreus using 0.1 M NaOH (alkali-soluble proteoglycans [F1] and alkali-insoluble proteoglycans [F3]) and 0.1 M HCl (acid-soluble proteoglycans [F2] and acid-insoluble proteoglycans [F4]), and their structures and immunomodulatory activities were investigated. The proteoglycans were found to contain carbohydrates (19.8–82.4%) with various amounts of proteins (7.7–67.3%), and glucose was the major monosaccharide unit present, along with trace amounts of galactose. The molecular weights (Mw) and the radius of gyration (Rg) of these proteoglycans showed ranges of 16 × 104–19,545 × 104 g/mol and 35–148 nm, respectively, showing significant variations in their molecular conformations. The backbones of F1 and F2 were mainly connected through a-(1→3), (1→4) and b-(1→6)-glycosidic linkages with some branches. The F1 and F2 proteoglycans significantly stimulated Raw264.7 cells to release nitric oxide (NO), prostaglandin E2 (PGE2) and various cytokines, such as IL-1β, TNF-α and IL-6 by inducing their mRNA expressions. Full article
(This article belongs to the Section Natural Products)
Open AccessArticle Synthesis and Biological Activity of Some 3-(4-(Substituted)-piperazin-1-yl)cinnolines
Molecules 2012, 17(1), 227-239; doi:10.3390/molecules17010227
Received: 15 November 2011 / Revised: 21 December 2011 / Accepted: 22 December 2011 / Published: 28 December 2011
Cited by 5 | PDF Full-text (259 KB)
Abstract
A new series of 6-substituted-4-methyl-3-(4-arylpiperazin-1-yl)cinnolines 810 were synthesized as potential antifungal agents via intramolecular cyclization of the respective 1-(2-arylhydrazono)-1-(4-arylpiperazin-1-yl)propan-2-ones 57, mediated by polyphosphoric acid (PPA). The amidrazones themselves were synthesized via direct interaction of the appropriate hydrazonoyl [...] Read more.
A new series of 6-substituted-4-methyl-3-(4-arylpiperazin-1-yl)cinnolines 810 were synthesized as potential antifungal agents via intramolecular cyclization of the respective 1-(2-arylhydrazono)-1-(4-arylpiperazin-1-yl)propan-2-ones 57, mediated by polyphosphoric acid (PPA). The amidrazones themselves were synthesized via direct interaction of the appropriate hydrazonoyl chlorides 4ad with the corresponding N-substituted piperazine in the presence of triethylamine. The structures of the new prepared compounds were confirmed by elemental analyses, 1H-NMR, 13C-NMR, and ESI-HRMS spectral data. The antitumor, antibacterial, and antifungal activity of the newly synthesized compounds was evaluated. Full article
(This article belongs to the Special Issue Heterocycles)
Open AccessArticle Practical Synthesis of Hydroxychromenes and Evaluation of Their Biological Activity
Molecules 2012, 17(1), 240-247; doi:10.3390/molecules17010240
Received: 5 December 2011 / Revised: 24 December 2011 / Accepted: 26 December 2011 / Published: 28 December 2011
Cited by 5 | PDF Full-text (198 KB)
Abstract
A simple and efficient seven steps synthesis of brodifacoum and difethialone from phenylacetyl chloride is described. The key synthetic strategies involve Friedel-Crafts acylation, intramolecular ring cyclization and condensation reaction in the presence of Brønsted-Lowry acids. It was found that brodifacoum showed favorable [...] Read more.
A simple and efficient seven steps synthesis of brodifacoum and difethialone from phenylacetyl chloride is described. The key synthetic strategies involve Friedel-Crafts acylation, intramolecular ring cyclization and condensation reaction in the presence of Brønsted-Lowry acids. It was found that brodifacoum showed favorable inhibiting activities on LPS-stimulated nitrite production in BV-2 microglia cells. Brodifacoum exhibited superior anti-inflammatory effects than difethialone. We expect that an efficient linear synthesis of 4-hydroxycoumarin derivatives and key fragments that are useful agents for the modulation of inflammation as well as inhibition of coagulation will be of practical use. Full article
Open AccessArticle Neonaucline, a New Indole Alkaloid from the Leaves of Ochreinauclea maingayii (Hook. f.) Ridsd. (Rubiaceae)
Molecules 2012, 17(1), 267-274; doi:10.3390/molecules17010267
Received: 25 October 2011 / Revised: 19 December 2011 / Accepted: 26 December 2011 / Published: 28 December 2011
Cited by 7 | PDF Full-text (305 KB)
Abstract
A new indole alkaloid; neonaucline (1), along with six known compounds–Cadamine (2), naucledine (3), harmane, benzamide, cinnamide and blumenol A–were isolated from the leaves of Ochreinauclea maingayii (Rubiaceae). In addition to that of compound 1, [...] Read more.
A new indole alkaloid; neonaucline (1), along with six known compounds–Cadamine (2), naucledine (3), harmane, benzamide, cinnamide and blumenol A–were isolated from the leaves of Ochreinauclea maingayii (Rubiaceae). In addition to that of compound 1, 13C-NMR data of cadamine (2) and naucledine (3) were also reported. Structural elucidations of these alkaloids were performed using spectroscopic methods especially 1D- and 2D-NMR, IR, UV and LCMS-IT-TOF. The excellent vasorelaxant activity on isolated rat aorta was observed for the alkaloids 13 after injection of each sample at 1 × 10−5 M. Full article
(This article belongs to the Section Natural Products)
Open AccessArticle Estimation of Dermatological Application of Creams with St. John’s Wort Oil Extracts
Molecules 2012, 17(1), 275-294; doi:10.3390/molecules17010275
Received: 4 November 2011 / Revised: 30 November 2011 / Accepted: 16 December 2011 / Published: 28 December 2011
Cited by 10 | PDF Full-text (628 KB)
Abstract
Oleum Hyperici, the oil extract of St. John’s Wort (SJW), is one of the oldest folk remedies, traditionally used in the topical treatment of wounds, bruises, ulcers, cuts, burns, hemorrhoids and also as an antiseptic. Considering the advantageous characteristics of emulsion [...] Read more.
Oleum Hyperici, the oil extract of St. John’s Wort (SJW), is one of the oldest folk remedies, traditionally used in the topical treatment of wounds, bruises, ulcers, cuts, burns, hemorrhoids and also as an antiseptic. Considering the advantageous characteristics of emulsion applications, in the present study we have formulated three O/W creams containing 15% (w/v) of SJW oil extract as an active ingredient. The aim was to estimate dermatological application of the prepared creams for the abovementioned indications. The extracts were prepared according to the prescriptions from traditional medicine, however with different vegetable oils used as an extractant, namely: Olive, palm and sunflower oil. The investigated O/W creams demonstrated significant antiinflammatory effects in an in vivo double-blind randomized study, using a sodium lauryl sulphate test. Both skin parameters assessed in the study (electrical capacitance and erythema index), were restored to the baseline value after a seven-day treatment with the tested creams. Almost all investigated SJW oil extracts and corresponding creams displayed the same antimicrobial activity against the most of the investigated microorganisms with obtained minimal inhibitory concentrations values of 1,280 µg/mL, 2,560 µg/mL or >2,560 µg/mL. Full article
(This article belongs to the Section Natural Products)
Open AccessArticle A New Triterpenoid Saponin from Abrus precatorius Linn
Molecules 2012, 17(1), 295-302; doi:10.3390/molecules17010295
Received: 30 November 2011 / Revised: 20 December 2011 / Accepted: 23 December 2011 / Published: 30 December 2011
Cited by 11 | PDF Full-text (241 KB)
Abstract
A new triterpenoid saponin, 3-O-β-D-glucopyranosyl-(1→2)-β-D-glucopyranosyl subprogenin D (1), together with six known triterpenoids: subprogenin D (2), abrusgenic acid (3), triptotriterpenic acid B (4), abruslactone A (5), abrusogenin ( [...] Read more.
A new triterpenoid saponin, 3-O-β-D-glucopyranosyl-(1→2)-β-D-glucopyranosyl subprogenin D (1), together with six known triterpenoids: subprogenin D (2), abrusgenic acid (3), triptotriterpenic acid B (4), abruslactone A (5), abrusogenin (6) and abrusoside C (7) were isolated from the leaves and stems of Abrus precatorius. Their structures were elucidated on the basis of physical and NMR analysis, respectively. Compounds 5 and 6 showed moderate cytotoxicity against MCF-7, SW1990, Hela, and Du-145 cell lines. Compounds 1, 2 and 4 were isolated from this plant for the first time. Full article
(This article belongs to the Section Natural Products)
Open AccessArticle Enantiomeric Separation and Determination of the Enantiomeric Impurity of Armodafinil by Capillary Electrophoresis with Sulfobutyl Ether-β-cyclodextrin as Chiral Selector
Molecules 2012, 17(1), 303-314; doi:10.3390/molecules17010303
Received: 16 December 2011 / Revised: 27 December 2011 / Accepted: 28 December 2011 / Published: 30 December 2011
Cited by 12 | PDF Full-text (243 KB)
Abstract
A selective capillary electrophoresis method using sulfobutyl ether-β-cyclodextrin as a chiral selector was developed and validated for the determination of the enantiomeric impurity of (R)-modafinil, i.e., armodafinil. Several parameters were optimized for a satisfactory enantioresolution, including the type and concentration of [...] Read more.
A selective capillary electrophoresis method using sulfobutyl ether-β-cyclodextrin as a chiral selector was developed and validated for the determination of the enantiomeric impurity of (R)-modafinil, i.e., armodafinil. Several parameters were optimized for a satisfactory enantioresolution, including the type and concentration of chiral selector and organic modifier, pH of background electrolyte (BGE), capillary temperature. The finally adopted condition was: 20 mmol/L phosphate buffer at pH 7.5, containing 20 mmol/L sulfobutyl ether-β-cyclodextrin and 20% methanol, at temperature of 25 °C. A good resolution of 3.3 for the two enantiomers of modafinil was achieved by applying the optimal conditions. The limit of detection (LOD) and limit of quantification (LOQ) of (S)-modafinil were 1.25 μg/mL and 2.50 μg/mL, respectively. The established method was also proven to display good selectivity, repeatability, linearity and accuracy. Finally, the method was used to investigate the enantiomeric purity of armodafinil in bulk samples. Full article
Open AccessArticle Neuroprotective Effects of Exogenous Activin A on Oxygen-Glucose Deprivation in PC12 Cells
Molecules 2012, 17(1), 315-327; doi:10.3390/molecules17010315
Received: 6 December 2011 / Revised: 19 December 2011 / Accepted: 22 December 2011 / Published: 30 December 2011
Cited by 14 | PDF Full-text (422 KB)
Abstract
Ischemic cerebrovascular disease is one of the most common causes of death in the World. Exogenous activin A (ActA) protects neurons against toxicity and plays a central role in regulating the brain’s response to injury. In the present study, we investigated the [...] Read more.
Ischemic cerebrovascular disease is one of the most common causes of death in the World. Exogenous activin A (ActA) protects neurons against toxicity and plays a central role in regulating the brain’s response to injury. In the present study, we investigated the mechanisms involved in the neuroprotective effects of ActA in a model of hypoxic-ischemic brain disease. We found that ActA could effectively increase the survival rate of PC12 cells and relieve oxygen-glucose deprivation (OGD) damage. To clarify the neuroprotective mechanisms of ActA, the effects of ActA on the ActA/Smad pathway and on the up-regulation of inducible nitric oxide synthase (NOS) and superoxide dismutase (SOD) were investigated using OGD in PC12 cells. The results showed that ActA could increase the expression of activin receptor IIA (ActRIIA), Smad3 and Smad4 and that 50 ng/mL and 100 ng/mL of ActA could reduce NO levels and increase SOD activity by 78.9% and 79.9%, respectively. These results suggested that the neuroprotective effects of ActA in ischemia could be related to the activation of the ActA/Smad signaling pathway and to its anti-oxidant activities. Full article
(This article belongs to the Section Medicinal Chemistry)
Open AccessArticle Enzyme Treatment-Free and Ligation-Independent Cloning Using Caged Primers in Polymerase Chain Reactions
Molecules 2012, 17(1), 328-340; doi:10.3390/molecules17010328
Received: 28 October 2011 / Revised: 26 December 2011 / Accepted: 27 December 2011 / Published: 30 December 2011
Cited by 6 | PDF Full-text (723 KB) | Supplementary Files
Abstract
A new simple scheme for constructing recombinant vectors that does not require any restriction enzyme, ligase, or any other special enzyme treatment has been developed. By using caged primers in PCR, unnatural sticky-ends of any sequence, which are sufficiently long for ligation-independent [...] Read more.
A new simple scheme for constructing recombinant vectors that does not require any restriction enzyme, ligase, or any other special enzyme treatment has been developed. By using caged primers in PCR, unnatural sticky-ends of any sequence, which are sufficiently long for ligation-independent cloning (LIC), are directly prepared on the product after a brief UVA irradiation. Target genes and vectors amplified by this light-assisted cohesive-ending (LACE) PCR join together in the desired arrangement in a simple mixture of them, tightly enough to be repaired and ligated in competent cells. Full article
(This article belongs to the Special Issue DNA-Templated Synthesis)
Open AccessArticle Inhibition of Sevoflurane Postconditioning Against Cerebral Ischemia Reperfusion-Induced Oxidative Injury in Rats
Molecules 2012, 17(1), 341-354; doi:10.3390/molecules17010341
Received: 2 December 2011 / Revised: 23 December 2011 / Accepted: 23 December 2011 / Published: 30 December 2011
Cited by 13 | PDF Full-text (213 KB)
Abstract
The volatile anesthetic sevoflurane is capable of inducing preconditioning and postconditioning effects in the brain. In this study, we investigated the effects of sevoflurane postconditioning on antioxidant and immunity indexes in cerebral ischemia reperfusion (CIR) rats. Rats were randomly assigned to five [...] Read more.
The volatile anesthetic sevoflurane is capable of inducing preconditioning and postconditioning effects in the brain. In this study, we investigated the effects of sevoflurane postconditioning on antioxidant and immunity indexes in cerebral ischemia reperfusion (CIR) rats. Rats were randomly assigned to five separate experimental groups I–V. In the sham group (I), rats were subjected to the same surgery procedures except for occlusion of the middle cerebral artery and exposed to 1.0 MAC sevoflurane 90 min after surgery for 30 min. IR control rats (group II) were subjected to middle cerebral artery occlusion (MCAO) for 90 min and exposed to O2 for 30 min at the beginning of reperfusion. Sevoflurane 0.5, 1.0 and 1.5 groups (III, IV, V) were all subjected to MCAO for 90 min, but at the beginning of reperfusion exposed to 0.5 MAC, 1.0 MAC or 1.5 MAC sevoflurane for 30 min, respectively. Results showed that sevoflurane postconditioning can decrease serum tumor necrosis factor-alpha (TNF-α), interleukin-1 beta (IL-1β), nitric oxide (NO), nitric oxide synthase (NOS) and increase serum interleukin-10 (IL-10) levels in cerebral ischemia reperfusion rats. In addition, sevoflurane postconditioning can still decrease blood lipid, malondialdehyde (MDA) levels, infarct volume and increase antioxidant enzymes activities, normal pyramidal neurons density in cerebral ischemia reperfusion rats. It can be concluded that sevoflurane postconditioning may decrease blood and brain oxidative injury and enhance immunity indexes in cerebral ischemia reperfusion rats. Full article
Open AccessArticle Synthesis and 5α-Reductase Inhibitory Activity of C21 Steroids Having 1,4-diene or 4,6-diene 20-ones and 4-Azasteroid 20-Oximes
Molecules 2012, 17(1), 355-368; doi:10.3390/molecules17010355
Received: 1 November 2011 / Revised: 14 December 2011 / Accepted: 16 December 2011 / Published: 30 December 2011
Cited by 15 | PDF Full-text (355 KB)
Abstract
The synthesis and evaluation of 5α-reductase inhibitory activity of some 4-azasteroid-20-ones and 20-oximes and 3β-hydroxy-, 3β-acetoxy-, or epoxy-substituted C21 steroidal 20-ones and 20-oximes having double bonds in the A and/or B ring are described. Inhibitory activity of synthesized compounds was assessed [...] Read more.
The synthesis and evaluation of 5α-reductase inhibitory activity of some 4-azasteroid-20-ones and 20-oximes and 3β-hydroxy-, 3β-acetoxy-, or epoxy-substituted C21 steroidal 20-ones and 20-oximes having double bonds in the A and/or B ring are described. Inhibitory activity of synthesized compounds was assessed using 5α-reductase enzyme and [1,2,6,7-3H]testosterone as substrate. All synthesized compounds were less active than finasteride (IC50: 1.2 nM). Three 4-azasteroid-2-oximes (compounds 4, 6 and 8) showed good inhibitory activity (IC50: 26, 10 and 11 nM) and were more active than corresponding 4-azasteroid 20-ones (compounds 3, 5 and 7). 3β-Hydroxy-, 3β-acetoxy- and 1α,2α-, 5α,6α- or 6α,7α-epoxysteroid-20-one and -20-oxime derivatives having double bonds in the A and/or B ring showed no inhibition of 5α-reductase enzyme. Full article
(This article belongs to the Special Issue Steroids)
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Open AccessArticle Silaphenolates and Silaphenylthiolates: Two Unexplored Unsaturated Silicon Compound Classes Influenced by Aromaticity
Molecules 2012, 17(1), 369-389; doi:10.3390/molecules17010369
Received: 30 November 2011 / Revised: 23 December 2011 / Accepted: 23 December 2011 / Published: 2 January 2012
Cited by 2 | PDF Full-text (936 KB)
Abstract
Monosilicon analogs of phenolates and phenylthiolates are studied by quantum chemical calculations. Three different silaphenolates and three different silaphenylthiolates are possible; the ortho-, meta-, and para-isomers. For the silaphenolates, the meta-isomer is the thermodynamically most stable, regardless if [...] Read more.
Monosilicon analogs of phenolates and phenylthiolates are studied by quantum chemical calculations. Three different silaphenolates and three different silaphenylthiolates are possible; the ortho-, meta-, and para-isomers. For the silaphenolates, the meta-isomer is the thermodynamically most stable, regardless if the substituent R at Si is H, t-Bu or SiMe3. However, with R = H and SiMe3 the energy differences between the three isomers are small, whereas with R = t-Bu the meta-isomer is ~5 kcal/mol more stable than the ortho-isomer. For the silaphenylthiolates the ortho-isomer is of lowest energy, although with R = H the ortho- and meta-isomers are isoenergetic. The calculated nucleus independent chemical shifts (NICS) indicate that the silaphenolates and silaphenylthiolates are influenced by aromaticity, but they are less aromatic than the parent silabenzene. The geometries and charge distributions suggest that all silaphenolates and silaphenylthiolates to substantial degrees are described by resonance structures with an exocyclic C=O double bond and a silapentadienyl anionic segment. Indeed, they resemble the all-carbon phenolate and phenylthiolate. Silaphenylthiolates are less bond alternate and have slightly more negative NICS values than analogous silaphenolates, suggesting that this compound class is a bit more aromatic. Dimerization of the silaphenolates and silaphenylthiolates is hampered due to intramolecular Coulomb repulsion in the dimers, and silaphenolates with a moderately bulky SiMe3 group as substituent at Si should prefer the monomeric form. Full article
Open AccessArticle Variations of Antioxidant Characteristics and Mineral Contents in Pulp and Peel of Different Apple (Malus domestica Borkh.) Cultivars from Pakistan
Molecules 2012, 17(1), 390-407; doi:10.3390/molecules17010390
Received: 13 October 2011 / Revised: 20 December 2011 / Accepted: 28 December 2011 / Published: 4 January 2012
Cited by 8 | PDF Full-text (241 KB)
Abstract
Variations of phenolics, antioxidant activity, and mineral contents in peel and pulp of five apple (Malus domestica Borkh.) cultivars from Pakistan, namely Red Delicious, Golden Delicious, Kashmiri Amri, Kala Kulu and Sky Spur were appraised. The mean extract yield of antioxidant [...] Read more.
Variations of phenolics, antioxidant activity, and mineral contents in peel and pulp of five apple (Malus domestica Borkh.) cultivars from Pakistan, namely Red Delicious, Golden Delicious, Kashmiri Amri, Kala Kulu and Sky Spur were appraised. The mean extract yield of antioxidant components obtained with 80:20 methanol-water (v/v), was found to be 22.1 g/100 g for peel and 14.2 g/100 g for pulp on a dry weight basis. The amounts of total phenolics and total flavonoids in peel and pulp of different cultivars of apple ranged from 1,907.5–2,587.9 mg gallic acid equivalent/100 g DW and 1,214.3–1,816.4 mg catechin equivalent/100 g DW and 1,185.2–1,475.5 mg GAE/100 g DW and 711.8–999.3 mg CE/100 g DW, respectively. The inhibition of linoleic acid peroxidation and DPPH scavenging activity of the extracts varied from 71.7–84.9 and 66.6–80.8% in peel, and 43.9–52.8 and 42.9–51.1% in pulp, respectively. Reducing power of the tested fruit part extracts at concentration 12.5 mg/mL ranged from 2.54–2.89 and 1.37–1.73, respectively. With regard to minerals analysis, both fruit parts showed the amount of K to be the highest, followed by Mg, Ca, Fe, Na and Zn. The results revealed that peel of the tested apple cultivars in this study had superior antioxidant capacity and mineral concentration than the pulp, indicating significant variations between the parts tested. Thus, consumption of apple fruits along with peel might be recommended to gaining better nutritive benefits. Full article
(This article belongs to the Section Natural Products)
Open AccessArticle Extraction Equilibrium of Indium(III) from Nitric Acid Solutions by Di(2-ethylhexyl)phosphoric Acid Dissolved in Kerosene
Molecules 2012, 17(1), 408-419; doi:10.3390/molecules17010408
Received: 30 November 2011 / Revised: 26 December 2011 / Accepted: 30 December 2011 / Published: 4 January 2012
Cited by 6 | PDF Full-text (465 KB)
Abstract
The extraction equilibrium of indium(III) from a nitric acid solution using di(2-ethylhexyl) phosphoric acid (D2EHPA) as an acidic extractant of organophosphorus compounds dissolved in kerosene was studied. By graphical and numerical analysis, the compositions of indium-D2EHPA complexes in organic phase and stoichiometry [...] Read more.
The extraction equilibrium of indium(III) from a nitric acid solution using di(2-ethylhexyl) phosphoric acid (D2EHPA) as an acidic extractant of organophosphorus compounds dissolved in kerosene was studied. By graphical and numerical analysis, the compositions of indium-D2EHPA complexes in organic phase and stoichiometry of the extraction reaction were examined. Nitric acid solutions with various indium concentrations at 25 °C were used to obtain the equilibrium constant of InR3 in the organic phase. The experimental results showed that the extraction distribution ratios of indium(III) between the organic phase and the aqueous solution increased when either the pH value of the aqueous solution and/or the concentration of the organic phase extractant increased. Finally, the recovery efficiency of indium(III) in nitric acid was measured. Full article
Open AccessArticle Metabolite Profiling of Four Major Flavonoids of Herba Epimdii in Zebrafish
Molecules 2012, 17(1), 420-432; doi:10.3390/molecules17010420
Received: 8 October 2011 / Revised: 8 December 2011 / Accepted: 24 December 2011 / Published: 4 January 2012
Cited by 15 | PDF Full-text (681 KB)
Abstract
The zebrafish model organism was applied first in a metabolic study of icariin, baohuoside I, epimedin A and epimedin C, which are flavonoids in Herba Epimedii. Metabolites of these compounds in zebrafish after exposure for 24 h were identified by HPLC-ESI-MS, [...] Read more.
The zebrafish model organism was applied first in a metabolic study of icariin, baohuoside I, epimedin A and epimedin C, which are flavonoids in Herba Epimedii. Metabolites of these compounds in zebrafish after exposure for 24 h were identified by HPLC-ESI-MS, whereby the separation was performed with a Zorbax C-18 column using a gradient elution of 0.05% formic acid acetonitrile-0.05% formic acid water. The quasi-molecular ions of compounds were detected in simultaneous negative and positive ionization modes. Metabolic products of icariin and epimedin C via cleavage of glucose residue instead of rhamnose residues were found, which coincided with the results using regular metabolic analysis methods. In addition, the zebrafish model was used to predict the metabolism of the trace component epimedin A, whose metabolic mechanisms haven’t been clearly elucidated with the current metabolism model. The metabolic pathway of epimedin A in zebrafish was similar to those of its homologue icariin and epimedin C. Our study demonstrated that the zebrafish model can successfully imitate the current models in elucidating metabolic pathways of model flavonoids, which has advantages of lower cost, far less amount of compound needed, easy set up and high performance. This novel model can also be applied in quickly predicting the metabolism of Chinese herb components, especially trace compounds. Full article
(This article belongs to the Section Natural Products)
Open AccessArticle Synthesis of Stable and Soluble One-Handed Helical Homopoly(substituted acetylene)s without the Coexistence of Any Other Chiral Moieties via Two-Step Polymer Reactions in Membrane State: Molecular Design of the Starting Monomer
Molecules 2012, 17(1), 433-451; doi:10.3390/molecules17010433
Received: 15 December 2011 / Revised: 28 December 2011 / Accepted: 30 December 2011 / Published: 4 January 2012
Cited by 4 | PDF Full-text (1651 KB)
Abstract
A soluble and stable one-handed helical poly(substituted phenylacetylene) without the coexistence of any other chiral moieties was successfully synthesized by asymmetric-induced polymerization of a chiral monomer followed by two-step polymer reactions in membrane state: (1) removing the chiral groups (desubstitution); [...] Read more.
A soluble and stable one-handed helical poly(substituted phenylacetylene) without the coexistence of any other chiral moieties was successfully synthesized by asymmetric-induced polymerization of a chiral monomer followed by two-step polymer reactions in membrane state: (1) removing the chiral groups (desubstitution); and (2) introduction of achiral long alkyl groups at the same position as the desubstitution to enhance the solubility of the resulting one-handed helical polymer (resubstitution). The starting chiral monomer should have four characteristic substituents: (i) a chiral group bonded to an easily hydrolyzed spacer group; (ii) two hydroxyl groups; (iii) a long rigid hydrophobic spacer between the chiral group and the polymerizing group; (iv) a long achiral group near the chiral group. As spacer group a carbonate ester was selected. The two hydroxyl groups formed intramolecular hydrogen bonds stabilizing a one-handed helical structure in solution before and after the two-step polymer reactions in membrane state. The rigid long hydrophobic spacer, a phenylethynylphenyl group, enhanced the solubility of the starting polymer, and realized effective chiral induction from the chiral side groups to the main chain in the asymmetric-induced polymerization. The long alkyl group near the chiral group avoided shrinkage of the membrane and kept the reactivity of resubstitution in membrane state after removing the chiral groups. The g value (g = ([θ]/3,300)/ε) for the CD signal assigned to the main chain in the obtained final polymer was almost the same as that of the starting polymer in spite of the absence of any other chiral moieties. Moreover, since the one-handed helical structure was maintained by the intramolecular hydrogen bonds in a solution, direct observation of the one-handed helicity of the final homopolymer has been realized in CD for the solution for the first time. Full article
(This article belongs to the Special Issue Chiroptical Techniques)
Open AccessArticle A Biosorption Isotherm Model for the Removal of Reactive Azo Dyes by Inactivated Mycelia of Cunninghamella elegans UCP542
Molecules 2012, 17(1), 452-462; doi:10.3390/molecules17010452
Received: 12 December 2011 / Revised: 20 December 2011 / Accepted: 20 December 2011 / Published: 4 January 2012
Cited by 9 | PDF Full-text (296 KB)
Abstract
The biosorption of three reactive azo dyes (red, black and orange II) found in textile effluents by inactive mycelium of Cunninghamella elegans has been investigated. It was found that after 120 hours of contact the adsorption led to 70%, 85%, 93% and [...] Read more.
The biosorption of three reactive azo dyes (red, black and orange II) found in textile effluents by inactive mycelium of Cunninghamella elegans has been investigated. It was found that after 120 hours of contact the adsorption led to 70%, 85%, 93% and 88% removal of reactive orange II, reactive black, reactive red and a mixture of them, respectively. The mycelium surface was found to be selective towards the azo dyes in the following order: reactive red > reactive black > orange II. Dye removal from a mixture solution resulted in 48.4 mg/g retention by mycelium and indicated a competition amongst the dyes for the cellular surface. A Freundlich adsorption isotherm model exhibited a better fit, thus suggesting the presence of heterogeneous binding sites. Electrondense deposits observed on the mycelium ultrastructure suggest that the dyes are mainly retained under the cellular surface of the inactive biomass of C. elegans. Full article
Open AccessArticle Quantum Mechanics Calculations, Basicity and Crystal Structure: The Route to Transition Metal Complexes of Azahelicenes
Molecules 2012, 17(1), 463-479; doi:10.3390/molecules17010463
Received: 13 December 2011 / Revised: 22 December 2011 / Accepted: 23 December 2011 / Published: 5 January 2012
Cited by 6 | PDF Full-text (684 KB) | Supplementary Files
Abstract
Quantum mechanics density functional calculations provided gas-phase electron distributions and proton affinities for several mono- and diaza[5]helicenes; computational results, together with experimental data concerning crystal structures and propensity to methylation of the nitrogen atom(s), provide a basis for designing azahelicene complexes with [...] Read more.
Quantum mechanics density functional calculations provided gas-phase electron distributions and proton affinities for several mono- and diaza[5]helicenes; computational results, together with experimental data concerning crystal structures and propensity to methylation of the nitrogen atom(s), provide a basis for designing azahelicene complexes with transition metal ions. Full article
(This article belongs to the Special Issue Heterocycles)
Open AccessArticle A PAMPA Assay as Fast Predictive Model of Passive Human Skin Permeability of New Synthesized Corticosteroid C-21 Esters
Molecules 2012, 17(1), 480-491; doi:10.3390/molecules17010480
Received: 15 December 2011 / Revised: 29 December 2011 / Accepted: 30 December 2011 / Published: 5 January 2012
Cited by 7 | PDF Full-text (323 KB)
Abstract
The permeation properties of twenty newly synthesized α-alkoxyalkanoyl and α-aryloxyalkanoyl C-21 esters of standard corticosteroids: Fluocinolone acetonide, dexamethasone, triamcinolone acetonide and hydrocortisone were established using a PAMPA assay (70% silicone oil and 30% isopropyl myristate). The data were compared with parent corticosteroids [...] Read more.
The permeation properties of twenty newly synthesized α-alkoxyalkanoyl and α-aryloxyalkanoyl C-21 esters of standard corticosteroids: Fluocinolone acetonide, dexamethasone, triamcinolone acetonide and hydrocortisone were established using a PAMPA assay (70% silicone oil and 30% isopropyl myristate). The data were compared with parent corticosteroids with addition of mometasone furoate and hydrocortisone acetate. All newly synthesized corticosteroid C-21 esters have effective permeability coefficients higher then -6, mostly followed with high values of retention factors and low permeation. The examined compounds were grouped through relationship between obtained retention factors and permeation parameters (groups I–III). The classification confirmed group I (membrane retentions as well as permeation lower then 30%) for all corticosteroid standards except mometasone furoate, a potent topical corticosteroid which, with high membrane retention (81%) and low permeation (7.7%) fits into group III. The largest number of new synthesized corticosteroids C-21 esters, among them all fluocinolone acetonide C-21 esters, have high membrane retentions (32.4%–86.5%) and low permeations (1.3%–27.1%), fitting in group III. The classification was related to previously obtained anti-inflammatory activity data for the fluocinolone acetonide C-21 esters series. According to the PAMPA results the new synthesized esters could be considered as potential new prodrugs with useful benefit/risk ratio. Full article
(This article belongs to the Section Medicinal Chemistry)
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Open AccessArticle Antimycobacterial Activity of Salicylanilide Benzenesulfonates
Molecules 2012, 17(1), 492-503; doi:10.3390/molecules17010492
Received: 28 November 2011 / Revised: 29 December 2011 / Accepted: 2 January 2012 / Published: 5 January 2012
Cited by 9 | PDF Full-text (230 KB)
Abstract
A series of eighteen novel esters of salicylanilides with benzenesulfonic acid were designed, synthesized and characterized by IR, 1H-NMR and 13C-NMR. They were evaluated in vitro as potential antimycobacterial agents towards Mycobacterium tuberculosis, Mycobacterium avium and two strains of [...] Read more.
A series of eighteen novel esters of salicylanilides with benzenesulfonic acid were designed, synthesized and characterized by IR, 1H-NMR and 13C-NMR. They were evaluated in vitro as potential antimycobacterial agents towards Mycobacterium tuberculosis, Mycobacterium avium and two strains of Mycobacterium kansasii. In general, the minimum inhibitory concentrations range from 1 to 500 µmol/L. The most active compound against M. tuberculosis was 4-chloro-2-(4-(trifluoromethyl)phenylcarbamoyl)-phenyl benzenesulfonate, with MIC of 1 µmol/L and towards M. kansasii its isomer 5-chloro-2-(4-(trifluoromethyl)phenylcarbamoyl)phenyl benzenesulfonate (MIC of 2–4 µmol/L). M. avium was the less susceptible strain. However, generally, salicylanilide benzenesulfonates did not surpass the activity of other salicylanilide esters with carboxylic acids. Full article
(This article belongs to the Section Medicinal Chemistry)
Open AccessArticle A New Triterpene from the Plant of Uncaria Macrophylla
Molecules 2012, 17(1), 504-510; doi:10.3390/molecules17010504
Received: 27 November 2011 / Revised: 29 December 2011 / Accepted: 30 December 2011 / Published: 5 January 2012
Cited by 9 | PDF Full-text (237 KB)
Abstract
Our ongoing investigations on the stem bark of Uncaria macrophylla afforded a new ursolic triterpene, 3β,6β,19α-trihydroxy-urs-12-en-28-oic acid-24-carboxylic acid methyl ester (1), named uncariursanic acid, and three known ursolic triterpenes including 3β,6β,19α-trihydroxy-23-oxo-urs-12-en-28-oic acid (2), 3β,6β,19α-trihydroxy-urs-12-en-28-oic acid ( [...] Read more.
Our ongoing investigations on the stem bark of Uncaria macrophylla afforded a new ursolic triterpene, 3β,6β,19α-trihydroxy-urs-12-en-28-oic acid-24-carboxylic acid methyl ester (1), named uncariursanic acid, and three known ursolic triterpenes including 3β,6β,19α-trihydroxy-23-oxo-urs-12-en-28-oic acid (2), 3β,6β,19α-trihydroxy-urs-12-en-28-oic acid (3) and ursolic acid (4). Their structures were elucidated by extensive spectral methods, including 1D and 2D NMR and HR-ESI-MS. The cytotoxicities of the four compounds were evaluated against two cancer cell lines (MCF-7 and HepG2) by the MTT method, and only compound 4 exhibited potent activity. Full article
(This article belongs to the Section Natural Products)
Open AccessArticle The Effect of Alkali and Ce(III) Ions on the Response Properties of Benzoxazine Supramolecules Prepared via Molecular Assembly
Molecules 2012, 17(1), 511-526; doi:10.3390/molecules17010511
Received: 8 October 2011 / Revised: 16 December 2011 / Accepted: 1 January 2012 / Published: 5 January 2012
Cited by 5 | PDF Full-text (647 KB)
Abstract
A series of benzoxazine monomer supramolecules with different substituted groups on their benzene ring was prepared with a Mannich reaction and characterized by FTIR, 1H-NMR and MS. The obtained products were 3,4-dihydro-3-(2’-hydroxyethylene)-6-methyl-2H-benzoxazine (BM1), 3,4-dihydro-3-(2’-hydroxyethylene)-6-ethyl-2H-benz-oxazine (BM2), and 3,4-dihydro-3-(2’-hydroxyethylene)-6-methoxy-2H-benzoxazine [...] Read more.
A series of benzoxazine monomer supramolecules with different substituted groups on their benzene ring was prepared with a Mannich reaction and characterized by FTIR, 1H-NMR and MS. The obtained products were 3,4-dihydro-3-(2’-hydroxyethylene)-6-methyl-2H-benzoxazine (BM1), 3,4-dihydro-3-(2’-hydroxyethylene)-6-ethyl-2H-benz-oxazine (BM2), and 3,4-dihydro-3-(2’-hydroxyethylene)-6-methoxy-2H-benzoxazine (BM3). The efficiency of alkali metal ion extraction from the products was determined with Pedersen’s technique, while the complexation of the Ce(III) ion was confirmed by the Job’s and the mole ratio methods. The evidence of complex formation between benzoxazine monomers and Ce(III) ions was obtained with FTIR and a computational simulation. Single phase ceria (CeO2) as observed with XRD was successfully prepared by calcinating the Ce(III)-benzoxazine monomer complexes at 600 °C for 2 h. In addition, the geometry of the ceria nanoparticles confirmed by TEM is spherical, with an average diameter of 10‑20 nm. Full article
(This article belongs to the Section Organic Synthesis)
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Open AccessArticle Synthesis and DPPH Radical Scavenging Activity of Prenylated Phenol Derivatives
Molecules 2012, 17(1), 556-570; doi:10.3390/molecules17010556
Received: 2 December 2011 / Revised: 27 December 2011 / Accepted: 4 January 2012 / Published: 6 January 2012
Cited by 14 | PDF Full-text (236 KB)
Abstract
The synthesis of twenty six prenylated phenols derivatives is reported. These compounds were obtained under mild conditions via Electrophilic Aromatic Substitution (EAS) coupling reactions between phenol derivatives containing electron-donor subtituents and 3-methyl-2-buten-1-ol using BF3×OEt2. Dialkylations were [...] Read more.
The synthesis of twenty six prenylated phenols derivatives is reported. These compounds were obtained under mild conditions via Electrophilic Aromatic Substitution (EAS) coupling reactions between phenol derivatives containing electron-donor subtituents and 3-methyl-2-buten-1-ol using BF3×OEt2. Dialkylations were also produced with this method. The formation of a chroman ring by intramolecular cyclization between a sp2 carbon from the prenyl group with the hydroxyl substituent in the ortho position occurred with some phenols. All the synthesized compounds were evaluated as antioxidants according to a DPPH radical scavenging activity assay. IC50 values of five synthesized compounds indicated they were as good antioxidants as Trolox™. Full article
(This article belongs to the Section Organic Synthesis)
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Open AccessArticle A Facile Solvent Free Claisen-Schmidt Reaction: Synthesis of α,α′-bis-(Substituted-benzylidene)cycloalkanones and α,α′-bis-(Substituted-alkylidene)cycloalkanones
Molecules 2012, 17(1), 571-583; doi:10.3390/molecules17010571
Received: 14 November 2011 / Revised: 30 December 2011 / Accepted: 4 January 2012 / Published: 9 January 2012
Cited by 17 | PDF Full-text (262 KB)
Abstract
Solvent-free Claisen-Schmidt reactions of cycloalkanones with various substituted benzaldehydes (aryl aldehydes) using solid NaOH (20 mol%) and applying a grinding technique were studied. Quantitative yields (96–98%) of α,α-bis-(substituted-benzylidene)cycloalkanones were obtained. Aliphatic aldehydes also provided α,α-bis-(substituted-alkylidene)cycloalkanones in very good [...] Read more.
Solvent-free Claisen-Schmidt reactions of cycloalkanones with various substituted benzaldehydes (aryl aldehydes) using solid NaOH (20 mol%) and applying a grinding technique were studied. Quantitative yields (96–98%) of α,α-bis-(substituted-benzylidene)cycloalkanones were obtained. Aliphatic aldehydes also provided α,α-bis-(substituted-alkylidene)cycloalkanones in very good yields with minor amounts of a-(substituted-alkylidene)cycloalkanones. The catalytic performance of solid NaOH was examined. The molar ratio of NaOH was optimized. The catalytic effect of solid NaOH was also evaluated by comparing it with KOH, NaOAc, and NH4OAc and it turns out that 20 mol% of solid NaOH was good enough to catalyze the Claisen-Schmidt reactions of cycloalkanones with various substituted benzaldehydes. Additionally, the regioselectivity of the Claisen-Schmidt reaction of acetone with benzaldehyde was examined. Using the same method, we could synthesize the corresponding bis-benzylidene- and mono-benzylideneacetone separately in 98% and 96% yields, respectively. Full article
(This article belongs to the Section Organic Synthesis)
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Open AccessArticle Daphnoretin Induces Cell Cycle Arrest and Apoptosis in Human Osteosarcoma (HOS) Cells
Molecules 2012, 17(1), 598-612; doi:10.3390/molecules17010598
Received: 23 November 2011 / Revised: 29 December 2011 / Accepted: 30 December 2011 / Published: 9 January 2012
Cited by 7 | PDF Full-text (373 KB)
Abstract
In this study antiproliferation, cell cycle arrest and apoptosis induced by daphnoretin in human osteosarcoma (HOS) cells were investigated. Antiproliferative activity was measured with the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay. The IC50 value of daphnoretin was 3.89 μM after 72 h treatment. [...] Read more.
In this study antiproliferation, cell cycle arrest and apoptosis induced by daphnoretin in human osteosarcoma (HOS) cells were investigated. Antiproliferative activity was measured with the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay. The IC50 value of daphnoretin was 3.89 μM after 72 h treatment. Induction of apoptosis was evidenced by apoptotic body appearance and Annexin V-FITC/PI apoptosis detection kit. Flow cytometric analysis indicated daphnoretin arrested the cell cycle in the G2/M phase. Western-blot assay showed that the G2/M phase arrest was accompanied by down-regulation of cdc2, cyclin A and cyclin B1. Moreover, daphnoretin inhibited Bcl-2 expression and induced Bax expression to desintegrate the outer mitochondrial membrane and causing cytochrome c release. Mitochondrial cytochrome c release was associated with the activation of caspase-9 and caspase-3 cascade. Our results demonstrated that daphnoretin caused death of HOS cells by blocking cells successively in G2/M phases and activating the caspase-3 pathway. Full article
(This article belongs to the Section Natural Products)
Open AccessArticle Investigating the Spectrum of Biological Activity of Substituted Quinoline-2-Carboxamides and Their Isosteres
Molecules 2012, 17(1), 613-644; doi:10.3390/molecules17010613
Received: 28 November 2011 / Revised: 27 December 2011 / Accepted: 4 January 2012 / Published: 10 January 2012
Cited by 20 | PDF Full-text (326 KB)
Abstract
In this study, a series of thirty-five substituted quinoline-2-carboxamides and thirty-three substituted naphthalene-2-carboxamides were prepared and characterized. They were tested for their activity related to the inhibition of photosynthetic electron transport (PET) in spinach (Spinacia oleracea L.) chloroplasts. Primary in vitro [...] Read more.
In this study, a series of thirty-five substituted quinoline-2-carboxamides and thirty-three substituted naphthalene-2-carboxamides were prepared and characterized. They were tested for their activity related to the 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 mycobacterial species. N-Cycloheptylquinoline-2-carboxamide, N-cyclohexylquinoline-2-carboxamide and N-(2-phenylethyl)quinoline-2-carboxamide showed higher activity against M. tuberculosis than the standards isoniazid or pyrazinamide and 2-(pyrrolidin-1-ylcarbonyl)quinoline and 1-(2-naphthoyl)pyrrolidine expressed higher activity against M. kansasii and M. avium paratuberculosis than the standards isoniazid or pyrazinamide. The most effective antimycobacterial compounds demonstrated insignificant toxicity against the human monocytic leukemia THP-1 cell line. The PET-inhibiting activity expressed by IC50 value of the most active compound N-benzyl-2-naphthamide was 7.5 μmol/L. For all compounds, the structure-activity relationships are discussed. Full article
(This article belongs to the Section Medicinal Chemistry)
Open AccessArticle Synthesis of New Liquid Crystalline Diglycidyl Ethers
Molecules 2012, 17(1), 645-656; doi:10.3390/molecules17010645
Received: 3 November 2011 / Revised: 13 December 2011 / Accepted: 17 December 2011 / Published: 10 January 2012
Cited by 8 | PDF Full-text (456 KB)
Abstract
The phenolic Schiff bases IVI were synthesized by condensation reactions between various diamines, namely o-dianisidine, o-tolidine and ethylenediamine with vanillin or p-hydroxybenzaldehyde and subsequent reactions between these phenolic Schiff bases and epichlorohydrin to produce new diglycidyl ethers [...] Read more.
The phenolic Schiff bases IVI were synthesized by condensation reactions between various diamines, namely o-dianisidine, o-tolidine and ethylenediamine with vanillin or p-hydroxybenzaldehyde and subsequent reactions between these phenolic Schiff bases and epichlorohydrin to produce new diglycidyl ethers IaVIa. The structures of these compounds were confirmed by CHN, FT-IR, 1H-NMR, and 13C-NMR spectroscopy. Their thermotropic liquid crystalline behavior was studied using differential scanning calorimetry (DSC) and polarizing optical microscopy (POM). All the diglycidyl ethers prepared exhibit nematic mesophases, except for Va and VIa, which did not show any transition mesophases, but simply flow to liquids. Full article
(This article belongs to the Section Organic Synthesis)
Open AccessArticle A New Prenylated Flavanone from Derris trifoliata Lour.
Molecules 2012, 17(1), 657-663; doi:10.3390/molecules17010657
Received: 30 October 2011 / Revised: 26 December 2011 / Accepted: 27 December 2011 / Published: 11 January 2012
Cited by 3 | PDF Full-text (189 KB) | Supplementary Files
Abstract
A new flavanone, 4′,5,7-trihydroxy-6,8-di-(2-hydroxy-3-methylbut-3-enyl)- flavanone, was isolated from the aerial parts of Derris trifoliate, together with eleven known compounds: rotenone, tephrosin, 12a-hydroxyrotenone, deguelin, 6a,12a-dehydro-rotenone, dehydrodeguelin, 7a-O-methyldeguelol, 7a-O-methylelliptonol, 5,7,3',4'-tetra-hydroxy-6,8-diprenylisoflavone, daidzein and 4'-hydroxy-7-methoxyflavanone. 7a-O-Methylelliptonol was isolated for [...] Read more.
A new flavanone, 4′,5,7-trihydroxy-6,8-di-(2-hydroxy-3-methylbut-3-enyl)- flavanone, was isolated from the aerial parts of Derris trifoliate, together with eleven known compounds: rotenone, tephrosin, 12a-hydroxyrotenone, deguelin, 6a,12a-dehydro-rotenone, dehydrodeguelin, 7a-O-methyldeguelol, 7a-O-methylelliptonol, 5,7,3',4'-tetra-hydroxy-6,8-diprenylisoflavone, daidzein and 4'-hydroxy-7-methoxyflavanone. 7a-O-Methylelliptonol was isolated for the first time from the genus Derris. Their structures were characterized on the basis of spectral data. Eight of the isolated compounds were found to be significantly toxic to brine shrimp (LC50 range 0.06–9.95 μg/mL). The new compound showed weak toxicity (LC50 = 211.31 μg/mL). Full article
(This article belongs to the Section Natural Products)
Open AccessArticle Induction of Apoptosis in Human Breast Adenocarcinoma Cells MCF-7 by Monapurpyridine A, a New Azaphilone Derivative from Monascus purpureus NTU 568
Molecules 2012, 17(1), 664-673; doi:10.3390/molecules17010664
Received: 21 November 2011 / Revised: 6 January 2012 / Accepted: 6 January 2012 / Published: 11 January 2012
Cited by 6 | PDF Full-text (414 KB) | Supplementary Files
Abstract
A new azaphilonidal derivative, monapurpyridine A (MPA), has recently been isolated from the fermented products of Monascus purpureus NTU 568. The structure of MPA was elucidated by nuclear magnetic resonance (1H-NMR, 13C-NMR, COSY, HMQC, and HMBC) and [...] Read more.
A new azaphilonidal derivative, monapurpyridine A (MPA), has recently been isolated from the fermented products of Monascus purpureus NTU 568. The structure of MPA was elucidated by nuclear magnetic resonance (1H-NMR, 13C-NMR, COSY, HMQC, and HMBC) and other spectroscopic analyses. Biological evaluation revealed that MPA could induce cell death in human breast adenocarcinoma cells MCF-7, and it has no significant toxicity to normal mammary epithelial cells M10. The MTT assay and flow cytometric analysis were employed to investigate cell viability and cell cycle influenced by MPA. Moreover, we used Western blot and caspase activity assay to demonstrate the activation of caspase-3, -8 and -9 resulted from MPA. All evidence supported that MPA was suitable for developing into a chemotherapeutic or chemopreventive agent against breast cancer. Full article
(This article belongs to the Section Natural Products)
Open AccessArticle Gamma Irradiation Increases the Antioxidant Properties of Tualang Honey Stored Under Different Conditions
Molecules 2012, 17(1), 674-687; doi:10.3390/molecules17010674
Received: 2 December 2011 / Revised: 5 January 2012 / Accepted: 8 January 2012 / Published: 11 January 2012
Cited by 5 | PDF Full-text (221 KB)
Abstract
This study was conducted to evaluate the effects of evaporation, gamma irradiation and temperature on the total polyphenols, flavonoids and 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical-scavenging activities of Tualang honey samples (n = 14) following storage over three, six or twelve months. The mean polyphenol [...] Read more.
This study was conducted to evaluate the effects of evaporation, gamma irradiation and temperature on the total polyphenols, flavonoids and 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical-scavenging activities of Tualang honey samples (n = 14) following storage over three, six or twelve months. The mean polyphenol concentrations of the six gamma irradiated honey samples at three, six and twelve months, respectively, were 96.13%, 98.01% and 102.03% higher than the corresponding values of the eight non-gamma irradiated samples. Similarly, the mean values for flavonoids at three, six and twelve months were 111.52%, 114.81% and 110.04% higher, respectively, for the gamma irradiated samples. The mean values for DPPH radical-scavenging activities at three, six and twelve months were also 67.09%, 65.26% and 44.65% higher, respectively, for the gamma irradiated samples. These data indicate that all gamma irradiated honey samples had higher antioxidant potential following gamma irradiation, while evaporation and temperature had minor effects on antioxidant potential. Full article
Open AccessArticle The Effect of β-Carotene Supplementation on the Pharmacokinetics of Nelfinavir and Its Active Metabolite M8 in HIV-1-infected Patients
Molecules 2012, 17(1), 688-702; doi:10.3390/molecules17010688
Received: 9 December 2011 / Revised: 5 January 2012 / Accepted: 6 January 2012 / Published: 12 January 2012
Cited by 5 | PDF Full-text (285 KB)
Abstract
β-Carotene supplements are often taken by individuals living with HIV-1. Contradictory results from in vitro studies suggest that β-carotene may inhibit or induce cytochrome P450 enzymes and transporters. The study objective was to investigate the effect of β-carotene on the steady-state pharmacokinetics of nelfinavir and its active metabolite M8 in HIV-1 infected individuals. Twelve hour nelfinavir pharmacokinetic analysis was conducted at baseline and after 28 days of β-carotene supplementation (25,000 IU twice daily). Nelfinavir and M8 concentrations were measured with validated assays. Non-compartmental methods were used to calculate the pharmacokinetic parameters. Geometric mean ratios comparing day 28 to day 1 area under the plasma concentration-time curve (AUC0–12 h), maximum (Cmax) and minimum (Cmin) concentrations of nelfinavir and M8 are presented with 90% confidence intervals. Eleven subjects completed the study and were included in the analysis. There were no significant differences in nelfinavir AUC0–12 h and Cmin (−10%, +4%) after β-carotene supplementation. The M8 Cmin was increased by 31% while the M8 AUC0–12 h and Cmax were unchanged. During the 28 day period, mean CD4+ % and CD4+:CD8+ ratio increased significantly (p < 0.01). β-carotene supplementation increased serum carotene levels but did not cause any clinically significant difference in the nelfinavir and M8 exposure. Full article
(This article belongs to the Special Issue Carotenoids)
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Open AccessArticle Controlled Fabrication of Flower-like Nickel Oxide Hierarchical Structures and Their Application in Water Treatment
Molecules 2012, 17(1), 703-715; doi:10.3390/molecules17010703
Received: 22 December 2011 / Revised: 4 January 2012 / Accepted: 9 January 2012 / Published: 12 January 2012
Cited by 8 | PDF Full-text (1558 KB)
Abstract
Flower-like NiO hierarchical structures with 2–5 μm diameter assembled from nanosheet building blocks have been successfully fabricated via a wet-chemical method combined with thermodecomposition technology. The template-free method is facile and effective in preparing flower-like NiO superstructures in high yield. The intermediate [...] Read more.
Flower-like NiO hierarchical structures with 2–5 μm diameter assembled from nanosheet building blocks have been successfully fabricated via a wet-chemical method combined with thermodecomposition technology. The template-free method is facile and effective in preparing flower-like NiO superstructures in high yield. The intermediate product and final hierarchical structures are characterized by transmission electron microscopy (TEM), scanning electron microscopy (SEM), X-ray diffraction (XRD), Fourier transform IR (FTIR), and thermogravimetric analysis (TGA). The effects of growth temperature and reaction time on the morphologies of the as-prepared structures were investigated by SEM characterization and a possible mechanism for the formation of flower-like NiO is proposed. Based on the nitrogen adsorption and desorption measurements, the BET surface area of the as-obtained sample is 55.7 m2/g and the pore-size distribution plot indicates a bimodal mesopore distribution, with pore sizes of ca. 2.6 nm and 7.4 nm, respectively. In comparison with sphere-like and rod-like structures, the flower-like NiO hierarchical structures show an excellent ability to rapidly remove various pollutants when used as adsorbent and photocatalyst in waste-water treatment, which may be attributed to its unique hierarchical and porous surface structures. Full article
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Open AccessArticle Evaluation of the Immunity Activity of Glycyrrhizin in AR Mice
Molecules 2012, 17(1), 716-727; doi:10.3390/molecules17010716
Received: 12 December 2011 / Revised: 29 December 2011 / Accepted: 29 December 2011 / Published: 12 January 2012
Cited by 13 | PDF Full-text (195 KB)
Abstract
In this study, we evaluated effect of glycyrrhizin on immunity function in allergic rhinitis (AR) mice. The AR mice model were induced by dripping ovalbumin in physiological saline (2 mg mL−1, 10 μL) into the bilateral nasal cavities using a [...] Read more.
In this study, we evaluated effect of glycyrrhizin on immunity function in allergic rhinitis (AR) mice. The AR mice model were induced by dripping ovalbumin in physiological saline (2 mg mL−1, 10 μL) into the bilateral nasal cavities using a micropipette. After the AR model was induced, mice were randomly divided into six groups: the normal control, model, lycopene 20 mg kg−1 (as positive control drug) group, and glycyrrhizin 10, 20, 30 mg kg−1 groups. After the sensitization day 14, lycopene (20 mg/kg BW) and glycyrrhizin (10, 20 and 30 mg/kg BW) were given orally for 20 days once a day. Mice in the normal control and model groups were given saline orally once a day for 20 days. Results showed that glycyrrhizin treatment could dose-dependently significantly reduce blood immunoglobulin E (IgE), interleukin-4 (IL-4), interleukin-5 (IL-5), interleukin-6 (IL-6), nitrous oxide (NO), tumor necrosis factor-alpha (TNF-α) levels and nitrous oxide synthase (NOS) activity and enhance blood immunoglobulin A (IgA), immunoglobulin G (IgG), immunoglobulin M (IgM), interleukin-2 (IL-2) and interleukin-12 (IL-12) levels in AR mice. Furthermore, glycyrrhizin treatment could dose-dependently significantly enhance acetylcholinesterase (AchE) activity and reduce substance P (SP) level in peripheral blood and nasal mucosa of AR mice. We conclude that glycyrrhizin can improve immunity function in AR mice, suggesting a potential drug for the prevention and therapy of AR. Full article
Open AccessArticle Reaction Characteristics of Andrographolide and its Analogue AL-1 with GSH, as a Simple Chemical Simulation of NF-κB Inhibition
Molecules 2012, 17(1), 728-739; doi:10.3390/molecules17010728
Received: 10 October 2011 / Revised: 4 January 2012 / Accepted: 12 January 2012 / Published: 12 January 2012
Cited by 6 | PDF Full-text (377 KB)
Abstract
14-α-Lipoic acid-3,19-dihydroxyandrographolide (AL-1, 2) is an analogue of andrographolide (Andro, 1) coupled to α-lipoic acid (LA, 4). AL-1 was at least 10-fold more potent than the natural parent compound Andro in inhibiting nuclear factor (NF)-κB activation in RIN-m cells. [...] Read more.
14-α-Lipoic acid-3,19-dihydroxyandrographolide (AL-1, 2) is an analogue of andrographolide (Andro, 1) coupled to α-lipoic acid (LA, 4). AL-1 was at least 10-fold more potent than the natural parent compound Andro in inhibiting nuclear factor (NF)-κB activation in RIN-m cells. In the present study, glutathione (GSH, 3) was used as a simple chemical model molecule of NF-κB with cysteine 62. The characteristics of the reaction between AL-1 or Andro and GSH were investigated to trace some possible elucidation for the inhibitive mechanism and stronger inhibition of AL-1 to NF-κB activation. The results showed that the main reaction products of AL-1 and Andro were identical, sulfhydryl adduct and amino adduct. AL-1 reacted much faster than Andro with GSH. The product yield of AL-1 was much higher than that of Andro. It was speculated that AL-1 might inhibit NF-κB by the same mechanism as Andro. And the faster reaction rate and higher yield may account for the stronger NF-κB inhibition of AL-1 when compared with Andro. Full article
Open AccessArticle Comparison of Polysaccharides from Two Species of Ganoderma
Molecules 2012, 17(1), 740-752; doi:10.3390/molecules17010740
Received: 20 December 2011 / Revised: 9 January 2012 / Accepted: 10 January 2012 / Published: 13 January 2012
Cited by 20 | PDF Full-text (1126 KB)
Abstract
Ganoderma lucidum and Ganoderma sinense, known as Lingzhi in Chinese, are commonly used Chinese medicines with excellent beneficial health effects. Triterpenes and polysaccharides are usually considered as their main active components. However, the content of triterpenes differs significantly between the two [...] Read more.
Ganoderma lucidum and Ganoderma sinense, known as Lingzhi in Chinese, are commonly used Chinese medicines with excellent beneficial health effects. Triterpenes and polysaccharides are usually considered as their main active components. However, the content of triterpenes differs significantly between the two species of Ganoderma. To date, a careful comparison of polysaccharides from the two species of Ganoderma has not been performed. In this study, polysaccharides from fruiting bodies of two species of Lingzhi collected from different regions of China were analyzed and compared based on HPSEC-ELSD and HPSEC-MALLS-RI analyses, as well as enzymatic digestion and HPTLC of acid hydrolysates. The results indicated that both the HPSEC-ELSD profiles and the molecular weights of the polysaccharides were similar. Enzymatic digestion showed that polyshaccharides from all samples of Lingzhi could be hydrolyzed by pectinase and dextranase. HPTLC profiles of their TFA hydrolysates colored with different reagents and their monosaccharides composition were also similar. Full article
(This article belongs to the Special Issue Natural Polysaccharides: Chemistry, Bioactivity and Analysis)
Open AccessArticle Isolation and Structural Characterisation of Okara Polysaccharides
Molecules 2012, 17(1), 753-761; doi:10.3390/molecules17010753
Received: 14 November 2011 / Revised: 18 December 2011 / Accepted: 5 January 2012 / Published: 13 January 2012
Cited by 5 | PDF Full-text (242 KB)
Abstract
Okara is a byproduct generated during tofu or soymilk production processes. Crude polysaccharide (yield 56.8%) was isolated by removing fat, protein and low molecular weight carbohydrates from initial okara. Crude okara polysaccharide was further divided into four soluble fractions and an insoluble [...] Read more.
Okara is a byproduct generated during tofu or soymilk production processes. Crude polysaccharide (yield 56.8%) was isolated by removing fat, protein and low molecular weight carbohydrates from initial okara. Crude okara polysaccharide was further divided into four soluble fractions and an insoluble residue fraction by extracting with 0.05 M EDTA + NH4 oxalate, 0.05 M NaOH, 1 M NaOH and 4 M NaOH, with yields of 7.7%, 3.6%, 20.7%, 16.0% and 27.9%, respectively. Arabinose, galactose, galacturonic acid, xylose and glucose (only for the insoluble fraction) were the major constituent sugars. The primary sugar residues of okara polysaccharides were 1,4-linked β-galactopyranose, 1,5- and 1,3-linked α-arabinofuranose, 1,5-linked α-xylofuranose, 1,2-linked, 1,2,4-linked and terminal α-rhamnopyranose (or fucopyranose), and 1,4-linked β-glucopyranose (only for the insoluble fraction), indicating okara polysaccharides might contain galactan, arabinan, arabinogalactan, xylogalacturonan, rhamnogalacturonan, xylan, xyloglucan and cellulose. Full article
(This article belongs to the Special Issue Natural Polysaccharides: Chemistry, Bioactivity and Analysis)
Open AccessArticle Anti-bacterial Treatment of Polyethylene by Cold Plasma for Medical Purposes
Molecules 2012, 17(1), 762-785; doi:10.3390/molecules17010762
Received: 16 November 2011 / Revised: 9 January 2012 / Accepted: 10 January 2012 / Published: 13 January 2012
Cited by 28 | PDF Full-text (1323 KB)
Abstract
Polyethylene (PE) is one of the most widely used polymers in many industrial applications. Biomedical uses seem to be attractive, with increasing interest. However, PE it prone to infections and its additional surface treatment is indispensable. An increase in resistance to infections [...] Read more.
Polyethylene (PE) is one of the most widely used polymers in many industrial applications. Biomedical uses seem to be attractive, with increasing interest. However, PE it prone to infections and its additional surface treatment is indispensable. An increase in resistance to infections can be achieved by treating PE surfaces with substances containing antibacterial groups such as triclosan (5-Chloro-2-(2,4-dichlorophenoxy)phenol) and chlorhexidine (1,1'-Hexamethylenebis[5-(4-chlorophenyl)biguanide]). This work has examined the impact of selected antibacterial substances immobilized on low-density polyethylene (LDPE) via polyacrylic acid (PAA) grafted on LDPE by low-temperature barrier discharge plasma. This LDPE surface treatment led to inhibition of Escherichia coli and Staphylococcus aureus adhesion; the first causes intestinal disease, peritonitis, mastitis, pneumonia, septicemia, the latter is the reason for wound and urinary tract infections. Full article
Open AccessArticle Preparation of Novel meta- and para-Substituted N-Benzyl Protected Quinuclidine Esters and Their Resolution with Butyrylcholinesterase
Molecules 2012, 17(1), 786-795; doi:10.3390/molecules17010786
Received: 8 December 2011 / Revised: 5 January 2012 / Accepted: 11 January 2012 / Published: 16 January 2012
PDF Full-text (424 KB)
Abstract
Since the optically active quinuclidin-3-ol is an important intermediate in the preparation of physiologically or pharmacologically active compounds, a new biocatalytic method for the production of chiral quinuclidin-3-ols was examined. Butyrylcholinesterase (BChE; EC 3.1.1.8) was chosen as a biocatalyst in a preparative [...] Read more.
Since the optically active quinuclidin-3-ol is an important intermediate in the preparation of physiologically or pharmacologically active compounds, a new biocatalytic method for the production of chiral quinuclidin-3-ols was examined. Butyrylcholinesterase (BChE; EC 3.1.1.8) was chosen as a biocatalyst in a preparative kinetic resolution of enantiomers. A series of racemic, (R)- and (S)-esters of quinuclidin-3-ol and acetic, benzoic, phthalic and isonicotinic acids were synthesized, as well as their racemic quaternary N-benzyl, meta- and para-N-bromo and N-methylbenzyl derivatives. After the resolution, all N-benzyl protected groups were successfully removed by catalytic transfer hydrogenation with ammonium formate (10% Pd-C). Hydrolyses studies with BChE confirmed that (R)-enantiomers of the prepared esters are much better substrates for the enzyme than (S)-enantiomers. Introduction of bromine atom or methyl group in the meta or para position of the benzyl moiety resulted in a considerable improvement of the stereoselectivity compared to the non-substituted compounds. Optically pure quinuclidin-3-ols were prepared in high yields and enantiopurity by the usage of various N-benzyl protected groups and BChE as a biocatalyst. Full article
(This article belongs to the Special Issue ECSOC-15)
Open AccessArticle Quantum Dot- Conjugated Anti-GRP78 scFv Inhibits Cancer Growth in Mice
Molecules 2012, 17(1), 796-808; doi:10.3390/molecules17010796
Received: 13 December 2011 / Revised: 10 January 2012 / Accepted: 12 January 2012 / Published: 16 January 2012
Cited by 12 | PDF Full-text (2660 KB) | Supplementary Files
Abstract
Semiconductor quantum dots (Qdots) have recently been shown to offer significant advantages over conventional fluorescent probes to image and study biological processes. The stability and low toxicity of QDs are well suited for biological applications. Despite this, the potential of Qdots remains [...] Read more.
Semiconductor quantum dots (Qdots) have recently been shown to offer significant advantages over conventional fluorescent probes to image and study biological processes. The stability and low toxicity of QDs are well suited for biological applications. Despite this, the potential of Qdots remains limited owing to the inefficiency of existing delivery methods. By conjugating Qdots with small antibody fragments targeting membrane-bound proteins, such as GRP78, we demonstrate here that the Quantum dot- Anti-GRP78 scFv (Qdot-GRP78) retains its immunospecificity and its distribution can be monitored by visualization of multi-color fluorescence imaging both in vitro and in vivo. Moreover we demonstrate here for the first time that Qdot-GRP78 scFv bioconjugates can be efficiently internalized by cancer cells, thus upregulate phophosphate-AKT-ser473 and possess biological anti-tumour activity as shown by inhibition of breast cancer growth in a xenograft model. This suggests that nanocarrier-conjugated scFvs can be used as a therapeutic antibody for cancer treatment. Full article
(This article belongs to the Section Molecular Diversity)
Open AccessArticle Comparative Computational Studies of 3,4-Dihydro-2,6-diaryl-4-oxo-pyrimidine-5-carbonitrile Derivatives as Potential Antinociceptive Agents
Molecules 2012, 17(1), 809-819; doi:10.3390/molecules17010809
Received: 27 October 2011 / Revised: 8 January 2012 / Accepted: 10 January 2012 / Published: 16 January 2012
Cited by 5 | PDF Full-text (266 KB)
Abstract
In this study, the antinociceptive properties of 3,4-dihydro-2,6-diaryl-4-oxo-pyrimidine-5-carbonitrile derivatives 5ai at doses of 25 and 50 mg/kg were evaluated in mice, using the abdominal constriction test. Molecular modeling studies were also performed using density functional theory calculations. These data provided [...] Read more.
In this study, the antinociceptive properties of 3,4-dihydro-2,6-diaryl-4-oxo-pyrimidine-5-carbonitrile derivatives 5ai at doses of 25 and 50 mg/kg were evaluated in mice, using the abdominal constriction test. Molecular modeling studies were also performed using density functional theory calculations. These data provided information about the electrostatic and ionization potentials and were used to compare the antinociceptive activity of the title compounds. The most active compounds were 3,4-dihydro-2-(4-chlorophenyl)-6-(4-methoxyphenyl)-4-oxo-pyrimidine-5-carbonitrile (5b) and 3,4-dihydro-2,6-diphenyl-4-oxo-pyrimidine-5-carbonitrile (5i), which inhibited the number of abdominal constrictions, at 50 mg/kg dose, in 88.6% and 88% of the sample, respectively. A preliminary SAR study demonstrated that halogen replacement in the phenyl rings of the compounds under study reduces the antinociceptive activity. DFT calculations showed that there is a high correlation between the ionization potentials and the analgesic properties of the compounds. It was found that compounds with a positive ionization potential (compounds 5b and 5i) were found to be the best analgesic drugs in this series. Full article
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Open AccessArticle Benzoylated Uronic Acid Building Blocks and Synthesis of N-Uronate Conjugates of Lamotrigine
Molecules 2012, 17(1), 820-835; doi:10.3390/molecules17010820
Received: 7 December 2011 / Revised: 2 January 2012 / Accepted: 4 January 2012 / Published: 16 January 2012
Cited by 2 | PDF Full-text (296 KB)
Abstract
A chemoenzymatic approach towards benzoylated uronic acid building blocks has been investigated starting with benzoylated hexapyranosides using regioselective C-6 enzymatic hydrolysis as the key step. Two of the building blocks were reacted with the antiepileptic drug lamotrigine. Glucuronidation of lamotrigine using methyl [...] Read more.
A chemoenzymatic approach towards benzoylated uronic acid building blocks has been investigated starting with benzoylated hexapyranosides using regioselective C-6 enzymatic hydrolysis as the key step. Two of the building blocks were reacted with the antiepileptic drug lamotrigine. Glucuronidation of lamotrigine using methyl (2,3,4-tri-O-benzoyl-α-D-glycopyranosyl bromide)uronate proceeded to give the N2-conjugate. However, lamotrigine-N2-glucuronide was most efficiently synthesised from methyl (2,3,4-tri-O-acetyl-α-D-glucopyranosyl bromide)uronate. Employing nitromethane as solvent with CdCO3 as a base lamotrigine-N2 glucuronide was prepared in a high yield (41%). Also methyl (2,3-di-O-benzoyl-4-deoxy-4-fluoro-α-D-glucosyl bromide)uronate underwent N-glucuronidation, but the product was unstable, eliminating hydrogen fluoride to give the corresponding enoate conjugate. Full article
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Open AccessArticle Isostreptazolin and Sannaphenol, Two New Metabolites from Streptomyces sannanensis
Molecules 2012, 17(1), 836-842; doi:10.3390/molecules17010836
Received: 3 November 2011 / Revised: 12 January 2012 / Accepted: 13 January 2012 / Published: 16 January 2012
Cited by 8 | PDF Full-text (177 KB)
Abstract
Two new compounds, isostreptazolin (1) and sannaphenol (2), were isolated from the culture broth of Streptomyces sannanensis and their structures elucidated on the basis of 1D and 2D NMR as well as MS, IR and UV spectroscopic data [...] Read more.
Two new compounds, isostreptazolin (1) and sannaphenol (2), were isolated from the culture broth of Streptomyces sannanensis and their structures elucidated on the basis of 1D and 2D NMR as well as MS, IR and UV spectroscopic data analysis. The cytotoxic activity of 1 and 2 were evaluated. Both compounds were inactive against H460 and HeLa cell lines at 100 mM. Full article
(This article belongs to the Section Natural Products)
Open AccessArticle Two Novel Naphthalene Glucosides and an Anthraquinone Isolated from Rumex dentatus and Their Antiproliferation Activities in Four Cell Lines
Molecules 2012, 17(1), 843-850; doi:10.3390/molecules17010843
Received: 6 December 2011 / Revised: 6 January 2012 / Accepted: 9 January 2012 / Published: 17 January 2012
Cited by 20 | PDF Full-text (156 KB) | Supplementary Files
Abstract
An ethyl acetate extract of the roots of Rumex dentatus L. was investigated. Three compounds were identified by their spectroscopic data as chrysophanol (1), 6-methyl-7-acetyl-1, 8-dihydroxy-3-methoxy naphthalene-1-O-β-D(L)-glucoside (2) and 6-methyl-7-acetyl-1, 8-dihydroxy naphthalene-1-O-β-D(L)-glucoside (3 [...] Read more.
An ethyl acetate extract of the roots of Rumex dentatus L. was investigated. Three compounds were identified by their spectroscopic data as chrysophanol (1), 6-methyl-7-acetyl-1, 8-dihydroxy-3-methoxy naphthalene-1-O-β-D(L)-glucoside (2) and 6-methyl-7-acetyl-1, 8-dihydroxy naphthalene-1-O-β-D(L)-glucoside (3) were found in the plant for the first time. Compounds 2 and 3 are novel compounds. Their antiproliferation activities were tested by the MTT assay in four cell lines (breast cancer MCF-7, gastric cancer 7901, melanoma A375 and oophoroma SKOV-3). Full article
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Open AccessArticle Effect of Efavirenz on UDP-Glucuronosyltransferase 1A1, 1A4, 1A6, and 1A9 Activities in Human Liver Microsomes
Molecules 2012, 17(1), 851-860; doi:10.3390/molecules17010851
Received: 28 October 2011 / Revised: 9 January 2012 / Accepted: 10 January 2012 / Published: 17 January 2012
Cited by 10 | PDF Full-text (291 KB)
Abstract
Efavirenz is a non-nucleoside reverse transcriptase inhibitor used for the treatment of human immunodeficiency virus type 1 infections. Drug interactions of efavirenz have been reported due to in vitro inhibition of CYP2C9, CYP2C19, CYP3A4, and UDP-glucuronosyltransferase 2B7 (UGT2B7) and in vivo CYP3A4 [...] Read more.
Efavirenz is a non-nucleoside reverse transcriptase inhibitor used for the treatment of human immunodeficiency virus type 1 infections. Drug interactions of efavirenz have been reported due to in vitro inhibition of CYP2C9, CYP2C19, CYP3A4, and UDP-glucuronosyltransferase 2B7 (UGT2B7) and in vivo CYP3A4 induction. The inhibitory potentials of efavirenz on the enzyme activities of four major UDP-glucuronosyltransferases (UGTs), 1A1, 1A4, 1A6, and 1A9, in human liver microsomes were investigated using liquid chromatography-tandem mass spectrometry. Efavirenz potently inhibited UGT1A4-mediated trifluoperazine N-glucuronidation and UGT1A9-mediated propofol glucuronidation, with Ki values of 2.0 and 9.4 μM, respectively. [I]/Ki ratios of efavirenz for trifluoperazine N-glucuronidation and propofol glucuronidation were 6.5 and 1.37, respectively. Efavirenz also moderately inhibited UGT1A1-mediated 17β-estradiol 3-glucuronidation, with a Ki value of 40.3 μM, but did not inhibit UGT1A6-mediated 1-naphthol glucuronidation. Those in vitro results suggest that efavirenz should be examined for potential pharmacokinetic drug interactions in vivo due to strong inhibition of UGT1A4 and UGT1A9. Full article
Open AccessArticle Phytochemical Study and Anti-inflammatory, Antidiabetic and Free Radical Scavenger Evaluations of Krameria pauciflora Methanol Extract
Molecules 2012, 17(1), 861-872; doi:10.3390/molecules17010861
Received: 16 December 2011 / Revised: 13 January 2012 / Accepted: 13 January 2012 / Published: 17 January 2012
Cited by 3 | PDF Full-text (248 KB) | Supplementary Files
Abstract
The plant Krameria pauciflora MOC et. Sessé ex DC. is used as an anti-inflammatory and antidiabetic in traditional medicine. The aim of this study was to evaluate the in vivo anti-inflammatory and antidiabetic effects of a methanol extract from the roots of [...] Read more.
The plant Krameria pauciflora MOC et. Sessé ex DC. is used as an anti-inflammatory and antidiabetic in traditional medicine. The aim of this study was to evaluate the in vivo anti-inflammatory and antidiabetic effects of a methanol extract from the roots of K. pauciflora. Dichloromethane and ethyl acetate extracts obtained by partitioning the methanol extract were also evaluated. Complete methanol and dichloromethane extracts showed anti-inflammatory effects at 3 mg/kg. An anti-inflammatory effect similar to indomethacin (10 mg/kg) was observed when the methanol and dichloromethane extracts, which contain a cycloartane-type triterpene and an sterol, were administered orally at several doses (3, 10, 30 and 100 mg/kg), whereas no anti-inflammatory effect was observed at any dose for the ethyl acetate extract, which contains catechin-type flavonoids. The antidiabetic effect of each extract was also determined. An antihyperglycaemic effect was observed in diabetic rats, but no effect in normoglycaemic animals was observed when the methanol extract was administrated at 30 mg/kg. All of the extracts exhibited radical scavenger activity. Additionally, constituents from all of the extracts were identified by NMR. This article supports the use of K. pauciflora as an anti-inflammatory because it exhibits a similar effect to indomethacin. However, its antidiabetic effect is not completely clear, although it could be useful for preventing diabetic complications. Full article
(This article belongs to the Section Natural Products)
Open AccessArticle Novel Benzothiazole, Benzimidazole and Benzoxazole Derivatives as Potential Antitumor Agents: Synthesis and Preliminary in Vitro Biological Evaluation
Molecules 2012, 17(1), 873-883; doi:10.3390/molecules17010873
Received: 12 December 2011 / Revised: 6 January 2012 / Accepted: 10 January 2012 / Published: 17 January 2012
Cited by 22 | PDF Full-text (596 KB)
Abstract
In a previous hit-to-lead research program targeting anticancer agents, two promising lead compounds, 1a and 1b, were found. However, the poor solubility of 1a and 1b made difficult further in vivo studies. To solve this problem, a lead optimization was conducted [...] Read more.
In a previous hit-to-lead research program targeting anticancer agents, two promising lead compounds, 1a and 1b, were found. However, the poor solubility of 1a and 1b made difficult further in vivo studies. To solve this problem, a lead optimization was conducted through introducing N-methyl-piperazine groups at the 2-position and 6-position. To our delight, the optimized analogue 1d showed comparable antiproliferative activity in vitro with better solubility, compared with 1a. Based on this result, the replacement of the benzothiazole scaffold with benzimidazole and benzoxazole moieties afforded 1f and 1g, whose activities were fundamentally retained. In the preliminary in vitro biological evaluation, the immunofluorescence staining of HCT116 cells indicated that 1d, 1f and 1g led to cytosolic vacuolization which was not induced by 1a at low micromolecular concentrations. These results suggest that these optimized compounds might potentially constitute a novel class of anticancer agents, which merit further studies. Full article
(This article belongs to the Section Medicinal Chemistry)
Open AccessArticle Design, Synthesis and Antifibrotic Activities of Carbohydrate- Modified 1-(Substituted aryl)-5-trifluoromethyl-2(1H) Pyridones
Molecules 2012, 17(1), 884-896; doi:10.3390/molecules17010884
Received: 16 November 2011 / Revised: 10 January 2012 / Accepted: 12 January 2012 / Published: 17 January 2012
Cited by 7 | PDF Full-text (279 KB)
Abstract
Pirfenidone, a pyridone compound, is an effective and novel antifibrotic agent. In this article, we describe the design, synthesis and activity evaluation of novel antifibrotic agents, 1-(substituted aryl)-5-trifluoromethyl-2(1H) pyridones modified with carbohydrate. Most of the title compounds exhibited comparable or [...] Read more.
Pirfenidone, a pyridone compound, is an effective and novel antifibrotic agent. In this article, we describe the design, synthesis and activity evaluation of novel antifibrotic agents, 1-(substituted aryl)-5-trifluoromethyl-2(1H) pyridones modified with carbohydrate. Most of the title compounds exhibited comparable or better inhibitory activity than fluorofenidone. Notably, compound 19a demonstrated the highest cell-based inhibitory activity against NIH 3T3 (IC50 = 0.17 mM). Full article
(This article belongs to the Section Medicinal Chemistry)
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Open AccessArticle Studies on 3-Oxoalkanenitriles: Novel Rearrangement Reactions Observed in Studies of the Chemistry of 3-Heteroaroyl-3-Oxoalkanenitriles as Novel Routes to 2-Dialkylaminopyridines
Molecules 2012, 17(1), 897-909; doi:10.3390/molecules17010897
Received: 1 December 2011 / Revised: 16 January 2012 / Accepted: 16 January 2012 / Published: 18 January 2012
Cited by 6 | PDF Full-text (442 KB) | Supplementary Files
Abstract
3-Aroyl and 3-heteroaroyl substituted 3-oxoalkanenitriles were synthesized by the reactions of activated aromatic and hetero-aromatic substances with cyanoacetic acid in the presence of acetic anhydride. As part of studies focusing on the preparation of cyanoacetyl-1-N-methylbenzimidazole, we observed that reaction of [...] Read more.
3-Aroyl and 3-heteroaroyl substituted 3-oxoalkanenitriles were synthesized by the reactions of activated aromatic and hetero-aromatic substances with cyanoacetic acid in the presence of acetic anhydride. As part of studies focusing on the preparation of cyanoacetyl-1-N-methylbenzimidazole, we observed that reaction of N-methyl-benzimidazole with the cyanoanhydride formed by condensation of cyanoacetic acid with acetic anhydride, leads to the formation of 2-(1,3-diacetyl-2,3-dihydro-1H-benzo[d]-imidazol-2-yl)acetonitrile (5), whose structure was confirmed by X-ray crystallographic analysis. 3-Oxoalkanenitriles 3a,b were observed to undergo condensation reactions with dimethylformamide dimethyl acetal (DMFDMA) to afford the corresponding enamino-nitriles, which react with malononitrile to give 2-dialkylaminopyridines through a pathway involving a new, unexpected rearrangement process. Reactions of 3-oxoalkanenitriles with ethyl acetoacetate were found to afford 2-oxopyran-3-carbonitriles, also occurring via this unexpected rearrangement process. Mechanisms to account for both rearrangement reactions are suggested. In addition, reactions of 3-oxoalkanenitriles with acetylacetone in acetic acid in the presence of ammonium acetate result in the formation of pyridine-3-carbonitriles. Finally, upon heating in the presence of zeolite 3-oxoalkanenitriles 3b,c self-trimerized to produce the corresponding aniline derivatives 23b,c. Full article
(This article belongs to the Special Issue Heterocycles)
Open AccessArticle Antioxidant Effect of Stryphnodendron rotundifolium Martius Extracts from Cariri-Ceará State (Brazil): Potential Involvement in Its Therapeutic Use
Molecules 2012, 17(1), 934-950; doi:10.3390/molecules17010934
Received: 4 November 2011 / Revised: 16 December 2011 / Accepted: 20 December 2011 / Published: 18 January 2012
Cited by 5 | PDF Full-text (701 KB)
Abstract
Stryphnodendron rotundifolium is a phytotherapic used in the northeast of Brazil for the treatment of inflammatory processes which normally are associated with oxidative stress. Consequently, we have tested the antioxidant properties of hydroalcoholic (HAB) and aqueous extracts (AB) from the bark and [...] Read more.
Stryphnodendron rotundifolium is a phytotherapic used in the northeast of Brazil for the treatment of inflammatory processes which normally are associated with oxidative stress. Consequently, we have tested the antioxidant properties of hydroalcoholic (HAB) and aqueous extracts (AB) from the bark and aqueous extract (AL) from the leaves of Stryphnodendron rotundifolium to determine a possible association between antioxidant activity and the popular use of this plant. Free radical scavenger properties were assessed by the quenching of 1′,1′-diphenil-2-picrylhydrazyl (DPPH) and the calculated IC50 were: HAB = 5.4 ± 0.7, AB = 12.0 ± 2.6, and AL = 46.3 ± 12.3 µg/mL. Total phenolic contents were: HAB = 102.7 ± 2.8, AB = 114.4 ± 14.6, and AL = 93.8 ± 9.1 µg/mg plant). HPLC/DAD analyses indicated that gallic acid, catechin, rutin and caffeic acid were the major components of the crude extracts of S. rotundifolium. Plant extracts inhibited Fe(II)-induced lipid peroxidation in brain homogenates. Iron chelation was also investigated and only HBA exhibited a weak activity. Taken together, the results suggest that S. rotundifolium could be considered an effective agent in the prevention of diseases associated with oxidative stress. Full article
(This article belongs to the Section Natural Products)
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Open AccessArticle Effect of Wine and Vinegar Processing of Rhizoma Corydalis on the Tissue Distribution of Tetrahydropalmatine, Protopine and Dehydrocorydaline in Rats
Molecules 2012, 17(1), 951-970; doi:10.3390/molecules17010951
Received: 29 November 2011 / Revised: 5 January 2012 / Accepted: 9 January 2012 / Published: 18 January 2012
Cited by 4 | PDF Full-text (1411 KB)
Abstract
Vinegar and wine processing of medicinal plants are two traditional pharmaceutical techniques which have been used for thousands of years in China. Tetrahydropalmatine (THP), dehydrocorydaline (DHC) and protopine are three major bioactive molecules in Rhizoma Corydalis. In this study, a simple and [...] Read more.
Vinegar and wine processing of medicinal plants are two traditional pharmaceutical techniques which have been used for thousands of years in China. Tetrahydropalmatine (THP), dehydrocorydaline (DHC) and protopine are three major bioactive molecules in Rhizoma Corydalis. In this study, a simple and reliable HPLC method was developed for simultaneous analysis of THP, DHC and protopine in rat tissues after gastric gavage administration of Rhizoma Corydalis. The validated HPLC method was successfully applied to investigate the effect of wine and vinegar processing on the compounds’ distribution in rat tissues. Our results showed that processing mainly affect the Tmax and mean residence time (MRT) of the molecules without changing their Cmax and AUC0–24 h Vinegar processing significantly increased the Tmax of DHC in heart, kidney, cerebrum, cerebrellum, brain stem and striatum and prolonged the Tmax of protopine in brain. No significant changes were observed on the Tmax of THP in rat tissues after vinegar processing. Wine processing reduced the Tmax of protopine and DHC in liver and spleen and Tmax of protopine in lung, but increased the Tmax of THP in all the rat tissues examined. To our knowledge, this is the first report on the effects of processing on the tissue distribution of the bioactive molecules from Rhizoma Corydalis. Full article
(This article belongs to the Section Natural Products)
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Open AccessArticle Synthesis, Reactions and Antimicrobial Activities of 8-Ethoxycoumarin Derivatives
Molecules 2012, 17(1), 971-988; doi:10.3390/molecules17010971
Received: 14 November 2011 / Revised: 1 January 2012 / Accepted: 4 January 2012 / Published: 18 January 2012
Cited by 7 | PDF Full-text (809 KB)
Abstract
Condensation of 3-acetyl-8-ethoxycoumarin (3) with thiosemicarbazide gave ethylidenehydrazinecarbothioamide 5, which was transformed into the thiazolidin-4-one derivatives 6,7. Interaction of 3 with DMF/POCl3 gave b-chloroacroline derivative 8. Treatment of 3 with malononitrile gave benzo[ [...] Read more.
Condensation of 3-acetyl-8-ethoxycoumarin (3) with thiosemicarbazide gave ethylidenehydrazinecarbothioamide 5, which was transformed into the thiazolidin-4-one derivatives 6,7. Interaction of 3 with DMF/POCl3 gave b-chloroacroline derivative 8. Treatment of 3 with malononitrile gave benzo[c]chromone and 2-aminobenzonitrile derivatives 9 and 10, respectively with respect to the reaction conditions. Condensation of 3-(2-bromoacetyl)-8-ethoxycoumarin (4) with o-phenylenediamine gave 3-(quioxaline-2-yl)-8-ethoxycoumarin hydrobromide (11), while 4 reacted with 2-aminopyridine to give chromenopyridopyrimidine derivative 12. Condensation of 4 with potassium thio-cyanate/methanol gave an unexpected derivative, 2H-chromeno-3-carboxy(methyl-carbonimidic)thioanhydride 16, which upon treatment with (NH2)2·H2O gave 3-ethoxy-2-hydroxybenzaldehyde azine 19. Interaction of 4 with thiourea derivatives gave thiazole derivatives 20a–c. The structures of the newly synthesized compounds were confirmed by their spectra data. The newly synthesized compounds were also screened for their antimicrobial activity. Full article
(This article belongs to the Special Issue Heterocycles)
Open AccessArticle Synthesis, Structure and Antifungal Activity of New 3-[(5-Aryl-1,3,4-oxadiazol-2-yl)methyl]benzo[d]thiazol-2(3H)-ones
Molecules 2012, 17(1), 989-1001; doi:10.3390/molecules17010989
Received: 7 December 2011 / Revised: 6 January 2012 / Accepted: 9 January 2012 / Published: 18 January 2012
Cited by 6 | PDF Full-text (546 KB) | Supplementary Files
Abstract
A series of new 3-[(5-aryl-1,3,4-oxadiazol-2-yl)methy])benzo[d]thiazol-2(3H)-ones were synthesized by reaction of (5-substituted-2-oxobenzothiazolin-3-yl)-acetohydrazide with various aromatic acids in POCl3 under reflux conditions. The structures of the title compounds were confirmed by 1H-NMR, 13C-NMR, IR, MS and elemental [...] Read more.
A series of new 3-[(5-aryl-1,3,4-oxadiazol-2-yl)methy])benzo[d]thiazol-2(3H)-ones were synthesized by reaction of (5-substituted-2-oxobenzothiazolin-3-yl)-acetohydrazide with various aromatic acids in POCl3 under reflux conditions. The structures of the title compounds were confirmed by 1H-NMR, 13C-NMR, IR, MS and elemental analysis. Furthermore, the structure of compound 4i was determined by single-crystal X-ray diffraction. The preliminary bioassy results indicated that some of them showed moderate inhibition activity against Colletotrichum orbiculare, Botrytis cinerea and Rhizoctonia solani. Full article
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Open AccessArticle Antifungal Activity of Eugenol Analogues. Influence of Different Substituents and Studies on Mechanism of Action
Molecules 2012, 17(1), 1002-1024; doi:10.3390/molecules17011002
Received: 26 December 2011 / Revised: 13 January 2012 / Accepted: 13 January 2012 / Published: 19 January 2012
Cited by 18 | PDF Full-text (324 KB)
Abstract
Twenty one phenylpropanoids (including eugenol and safrole) and synthetic analogues, thirteen of them new compounds, were evaluated for antifungal properties, first with non-targeted assays against a panel of human opportunistic pathogenic fungi. Some structure-activity relationships could be observed, mainly related to the [...] Read more.
Twenty one phenylpropanoids (including eugenol and safrole) and synthetic analogues, thirteen of them new compounds, were evaluated for antifungal properties, first with non-targeted assays against a panel of human opportunistic pathogenic fungi. Some structure-activity relationships could be observed, mainly related to the influence of an allyl substituent at C-4, an OH group at C-1 and an OCH3 at C-2 or the presence of one or two NO2 groups in different positions of the benzene ring. All active compounds were tested in a second panel of clinical isolates of C. albicans and non-albicans Candida spp., Cryptococcus neoformans and dermatophytes. The eugenol derivative 4-allyl-2-methoxy-5-nitrophenol (2) was the most active structure against all strains tested, and therefore it was submitted to targeted assays. These studies showed that the antifungal activity of 2 was not reversed in the presence of an osmotic support such as sorbitol, suggesting that it does not act by inhibiting the fungal cell wall synthesis or assembly. On the other hand, the Ergosterol Assay showed that 2 did not bind to the main sterol of the fungal membrane up to 250 µg mL−1. In contrast, a 22% of fungal membrane damage was observed at concentrations = 1 × MIC and 71% at 4× MIC, when 2 was tested in the Cellular Leakage assay. The comparison of log P and MICs for all compounds revealed that the antifungal activity of the eugenol analogues would not to be related to lipophilicity. Full article
(This article belongs to the Special Issue Dendrimers - from Synthesis to Applications)
Open AccessArticle Synthesis and Preliminary Antimicrobial Activities of New Arylideneamino-1,3,4-thiadiazole-(thio/dithio)-acetamido Cephalosporanic Acids
Molecules 2012, 17(1), 1025-1038; doi:10.3390/molecules17011025
Received: 9 October 2011 / Revised: 27 December 2011 / Accepted: 4 January 2012 / Published: 19 January 2012
Cited by 10 | PDF Full-text (271 KB)
Abstract
New derivatives of 7-aminocephalosporanic acid 18 were synthesized by acylation of the 7-amino group of the cephem nucleus with various arylidinimino-1,3,4-thiadiazole-thio(or dithio)-acetic acid intermediates 3ad and 5ad, respectively, so the acyl side chains of these [...] Read more.
New derivatives of 7-aminocephalosporanic acid 18 were synthesized by acylation of the 7-amino group of the cephem nucleus with various arylidinimino-1,3,4-thiadiazole-thio(or dithio)-acetic acid intermediates 3ad and 5ad, respectively, so the acyl side chains of these new cephalosporins contained a sulfide or disulfide bond. This unique combination of a Schiff base with the sulfide or disulfide bonds in the acyl side chain afforded new cephalosporins of reasonable potencies, some of which were found to possess moderate activities against the tested microorganisms. Their chemical structures were characterized by ¹H-NMR, IR spectroscopy and elemental microanalysis. Preliminary in vitro antimicrobial activities of the prepared cephalosporins were investigated using a panel of selected microorganisms. Results indicated that the newly synthesized cephalosporins containing disulfide bonds (compounds 58) exhibited better activities against Staphylococcus aureus and Escherichia coli. The cephalosporins cross-linked by a sulfide bond (compounds 14) showed a slight change in antimicrobial activities when compared with that of the reference cephalosporin (cephalexin). Full article
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Open AccessArticle The Metal Cation Chelating Capacity of Astaxanthin. Does This Have Any Influence on Antiradical Activity?
Molecules 2012, 17(1), 1039-1054; doi:10.3390/molecules17011039
Received: 30 November 2011 / Revised: 16 December 2011 / Accepted: 5 January 2012 / Published: 20 January 2012
Cited by 5 | PDF Full-text (1227 KB) | Supplementary Files
Abstract
In this Density Functional Theory study, it became apparent that astaxanthin (ASTA) may form metal ion complexes with metal cations such as Ca+2, Cu+2, Pb+2, Zn+2, Cd+2 and Hg+2. The presence [...] Read more.
In this Density Functional Theory study, it became apparent that astaxanthin (ASTA) may form metal ion complexes with metal cations such as Ca+2, Cu+2, Pb+2, Zn+2, Cd+2 and Hg+2. The presence of metal cations induces changes in the maximum absorption bands which are red shifted in all cases. Therefore, in the case of compounds where metal ions are interacting with ASTA, they are redder in color. Moreover, the antiradical capacity of some ASTA-metal cationic complexes was studied by assessing their vertical ionization energy and vertical electron affinity, reaching the conclusion that metal complexes are slightly better electron donors and better electron acceptors than ASTA. Full article
(This article belongs to the Special Issue Carotenoids)
Open AccessArticle Fluorescent Lipids: Functional Parts of Fusogenic Liposomes and Tools for Cell Membrane Labeling and Visualization
Molecules 2012, 17(1), 1055-1073; doi:10.3390/molecules17011055
Received: 30 November 2011 / Revised: 10 January 2012 / Accepted: 16 January 2012 / Published: 20 January 2012
Cited by 16 | PDF Full-text (1126 KB) | Supplementary Files
Abstract
In this paper a rapid and highly efficient method for controlled incorporation of fluorescent lipids into living mammalian cells is introduced. Here, the fluorescent molecules have two consecutive functions: First, they trigger rapid membrane fusion between cellular plasma membranes and the lipid [...] Read more.
In this paper a rapid and highly efficient method for controlled incorporation of fluorescent lipids into living mammalian cells is introduced. Here, the fluorescent molecules have two consecutive functions: First, they trigger rapid membrane fusion between cellular plasma membranes and the lipid bilayers of their carrier particles, so called fusogenic liposomes, and second, after insertion into cellular membranes these molecules enable fluorescence imaging of cell membranes and membrane traffic processes. We tested the fluorescent derivatives of the following essential membrane lipids for membrane fusion: Ceramide, sphingomyelin, phosphocholine, phosphatidylinositol-bisphosphate, ganglioside, cholesterol, and cholesteryl ester. Our results show that all probed lipids could more efficiently be incorporated into the plasma membrane of living cells than by using other methods. Moreover, labeling occurred in a gentle manner under classical cell culture conditions reducing cellular stress responses. Staining procedures were monitored by fluorescence microscopy and it was observed that sphingolipids and cholesterol containing free hydroxyl groups exhibit a decreased distribution velocity as well as a longer persistence in the plasma membrane compared to lipids without hydroxyl groups like phospholipids or other artificial lipid analogs. After membrane staining, the fluorescent molecules were sorted into membranes of cell organelles according to their chemical properties and biological functions without any influence of the delivery system. Full article
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Open AccessCommunication The Newly Isolated Endophytic Fungus Paraconiothyrium sp. LK1 Produces Ascotoxin
Molecules 2012, 17(1), 1103-1112; doi:10.3390/molecules17011103
Received: 19 December 2011 / Revised: 6 January 2012 / Accepted: 11 January 2012 / Published: 20 January 2012
Cited by 6 | PDF Full-text (324 KB) | Supplementary Files
Abstract
We have isolated five endophytic fungi from the roots of Capsicum annuum, Cucumis sativus and Glycine max. The culture filtrates (CF) of these endophytes were screened on dwarf mutant rice (Waito-C) and normal rice (Dongjin-byeo). Endophyte CAC-1A significantly [...] Read more.
We have isolated five endophytic fungi from the roots of Capsicum annuum, Cucumis sativus and Glycine max. The culture filtrates (CF) of these endophytes were screened on dwarf mutant rice (Waito-C) and normal rice (Dongjin-byeo). Endophyte CAC-1A significantly inhibited the growth of Waito-C and Dongjin-byeo. Endophyte CAC-1A was identified as Paraconiothyrium sp. by sequencing the ITS rDNA region and phylogenetic analysis. The ethyl acetate fraction of Paraconiothyrium sp. suppressed the germination of Lactuca sativa and Echinochloa crus-galli seeds. The ethyl acetate fraction of the endophyte was subjected to bioassay-guided isolation and we obtained the phytotoxic compound ascotoxin (1) which was characterized through NMR and GC/MS techniques. Ascotoxin revealed 100% inhibitory effects on seed germination of Echinochloa crus-galli. Compound (1) was isolated for the first time from Paraconiothyrium sp. Full article
(This article belongs to the Section Natural Products)
Open AccessArticle Phenolic Enriched Extract of Baccharis trimera Presents Anti-inflammatory and Antioxidant Activities
Molecules 2012, 17(1), 1113-1123; doi:10.3390/molecules17011113
Received: 5 December 2011 / Revised: 27 December 2011 / Accepted: 9 January 2012 / Published: 23 January 2012
Cited by 15 | PDF Full-text (246 KB)
Abstract
Baccharis trimera is a plant popularly used as a tea and to treat gastrointestinal diseases and inflammatory processes as well. The total phenolic content was determined and the antioxidant and anti-inflammatory activities of six extracts (dichloromethane, ethyl acetate, butanol, aqueous, saponin and phenolic) from B. trimera were evaluated. Using carrageenan-induced pleurisy as a model of acute inflammation, the phenolic extract at 15 mg/kg decreased significantly the analyzed parameters when compared to the carrageenan group ( p < 0.05), thus showing potential anti-inflammatory activity. The total phenolic content and antioxidant activity were evaluated by the Folin-Ciocalteau and DPPH methods, respectively. Phenolic and ethyl acetate extracts presented higher antioxidant activity ( p < 0.05) than ascorbic acid. The phenolic extract also showed the highest antioxidant potential in relation to the other extracts, thus suggesting that the antioxidant and anti-inflammatory activities were due to the presence of phenolic compounds. Full article
(This article belongs to the Section Natural Products)
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Open AccessArticle New Sorafenib Derivatives: Synthesis, Antiproliferative Activity Against Tumour Cell Lines and Antimetabolic Evaluation
Molecules 2012, 17(1), 1124-1137; doi:10.3390/molecules17011124
Received: 26 November 2011 / Revised: 1 January 2012 / Accepted: 5 January 2012 / Published: 23 January 2012
Cited by 5 | PDF Full-text (305 KB)
Abstract
Sorafenib is a relatively new cytostatic drug approved for the treatment of renal cell and hepatocellular carcinoma. In this report we describe the synthesis of sorafenib derivatives 4ae which differ from sorafenib in their amide part. A 4-step synthetic pathway [...] Read more.
Sorafenib is a relatively new cytostatic drug approved for the treatment of renal cell and hepatocellular carcinoma. In this report we describe the synthesis of sorafenib derivatives 4ae which differ from sorafenib in their amide part. A 4-step synthetic pathway includes preparation of 4-chloropyridine-2-carbonyl chloride hydrochloride (1), 4-chloro-pyridine-2-carboxamides 2ae, 4-(4-aminophenoxy)-pyridine-2-carboxamides 3ae and the target compounds 4-[4-[[4-chloro-3-(trifluoromethyl)phenyl]carbamoylamino]-phenoxy]-pyridine-2-carboxamides 4ae. All compounds were fully chemically characterized and evaluated for their cytostatic activity against a panel of carcinoma, lymphoma and leukemia tumour cell lines. In addition, their antimetabolic potential was investigated as well. The most prominent antiproliferative activity was obtained for compounds 4ae (IC50 = 1-4.3 μmol·L−1). Their potency was comparable to the potency of sorafenib, or even better. The compounds inhibited DNA, RNA and protein synthesis to a similar extent and did not discriminate between tumour cell lines and primary fibroblasts in terms of their anti-proliferative activity. Full article
(This article belongs to the Section Medicinal Chemistry)

Review

Jump to: Research

Open AccessReview Phenolic Profile of Edible Honeysuckle Berries (Genus Lonicera) and Their Biological Effects
Molecules 2012, 17(1), 61-79; doi:10.3390/molecules17010061
Received: 18 November 2011 / Revised: 14 December 2011 / Accepted: 19 December 2011 / Published: 22 December 2011
Cited by 37 | PDF Full-text (1084 KB)
Abstract
The current status of research on polyphenolic compounds in the berries of edible honeysuckle and their biological effects, including recommended utilization, are reviewed. The major classes of phenolic compounds in the blue berried honeysuckle are flavonols (quercetin, rutin, quercitrin) and flavanes (proanthocyanidins, [...] Read more.
The current status of research on polyphenolic compounds in the berries of edible honeysuckle and their biological effects, including recommended utilization, are reviewed. The major classes of phenolic compounds in the blue berried honeysuckle are flavonols (quercetin, rutin, quercitrin) and flavanes (proanthocyanidins, catechins) and anthocyanins. Cyanidin-3-glucoside and cyanidin-3-rutinoside are considered as major anthocyanidins in edible honeysuckle berries. Such a high level of antioxidant activity in the berries of different species of the genus Lonicera is especially due to the high level of polyphenolic compounds, especially anthocyanins. These berries seem to be prospective sources of health-supporting phytochemicals that exhibit beneficial anti-adherence and chemo-protective activities, thus they may provide protection against a number of chronic conditions, e.g., cancer, diabetes mellitus, tumour growth or cardiovascular and neurodegenerative diseases. Full article
(This article belongs to the Section Natural Products)
Open AccessReview Like a Bolt from the Blue: Phthalocyanines in Biomedical Optics
Molecules 2012, 17(1), 98-144; doi:10.3390/molecules17010098
Received: 4 November 2011 / Revised: 5 December 2011 / Accepted: 14 December 2011 / Published: 23 December 2011
Cited by 75 | PDF Full-text (630 KB)
Abstract
The purpose of this review is to compile preclinical and clinical results on phthalocyanines (Pcs) as photosensitizers (PS) for Photodynamic Therapy (PDT) and contrast agents for fluorescence imaging. Indeed, Pcs are excellent candidates in these fields due to their strong absorbance in [...] Read more.
The purpose of this review is to compile preclinical and clinical results on phthalocyanines (Pcs) as photosensitizers (PS) for Photodynamic Therapy (PDT) and contrast agents for fluorescence imaging. Indeed, Pcs are excellent candidates in these fields due to their strong absorbance in the NIR region and high chemical and photo-stability. In particular, this is mostly relevant for their in vivo activation in deeper tissular regions. However, most Pcs present two major limitations, i.e., a strong tendency to aggregate and a low water-solubility. In order to overcome these issues, both chemical tuning and pharmaceutical formulation combined with tumor targeting strategies were applied. These aspects will be developed in this review for the most extensively studied Pcs during the last 25 years, i.e., aluminium-, zinc- and silicon-based Pcs. Full article
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Open AccessReview Chromone and Flavonoid Alkaloids: Occurrence and Bioactivity
Molecules 2012, 17(1), 191-206; doi:10.3390/molecules17010191
Received: 9 November 2011 / Revised: 7 December 2011 / Accepted: 24 December 2011 / Published: 27 December 2011
Cited by 64 | PDF Full-text (259 KB)
Abstract
The chromone and flavonoid alkaloids represent an unusual group of structurally diverse secondary metabolites, derived from the convergence of multiple biosynthetic pathways that are widely distributed through the plant and animal kingdoms. Many of them have been discovered through bioassay-guided chemical investigations [...] Read more.
The chromone and flavonoid alkaloids represent an unusual group of structurally diverse secondary metabolites, derived from the convergence of multiple biosynthetic pathways that are widely distributed through the plant and animal kingdoms. Many of them have been discovered through bioassay-guided chemical investigations of traditional medicines, suggesting potential therapeutic significance. Their unique structures and varied pharmacological activities may provide important new leads for the discovery of drugs with novel mechanisms of action. Potential therapeutic indications are as diverse as cancer and viral infections, inflammation and immunomodulation, neurological and psychiatric conditions, and diabetes. Full article
(This article belongs to the Special Issue Alkaloids: Novel Therapeutic Perspectives)
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Open AccessReview Oligosaccharides Might Contribute to the Antidiabetic Effect of Honey: A Review of the Literature
Molecules 2012, 17(1), 248-266; doi:10.3390/molecules17010248
Received: 26 October 2011 / Revised: 15 December 2011 / Accepted: 16 December 2011 / Published: 28 December 2011
Cited by 12 | PDF Full-text (216 KB)
Abstract
Evidence shows that honey improves glycemic control in diabetes mellitus. Besides its hypoglycemic effect, studies indicate that honey ameliorates lipid abnormalities in rats and humans with diabetes. The majority of these studies do not examine the mechanisms by which honey ameliorates glycemic [...] Read more.
Evidence shows that honey improves glycemic control in diabetes mellitus. Besides its hypoglycemic effect, studies indicate that honey ameliorates lipid abnormalities in rats and humans with diabetes. The majority of these studies do not examine the mechanisms by which honey ameliorates glycemic and/or lipid derangements. The gut microbiota is now recognized for its ability to increase energy harvest from the diet and alter lipid metabolism of the host. Recently available data implicate a causal role of these gut microbes in the pathophysiology of obesity, insulin resistance, and diabetes mellitus. In this review, we present some of the latest findings linking gut microbiota to pathogenesis of obesity, insulin resistance, and diabetes mellitus. The review also underlines data that demonstrate the beneficial effects of oligosaccharides on various abnormalities commonly associated with these disorders. Based on the similarities of some of these findings with those of honey, together with the evidence that honey contains oligosaccharides, we hypothesize that oligosaccharides present in honey might contribute to the antidiabetic and other health-related beneficial effects of honey. We anticipate that the possibility of oligosaccharides in honey contributing to the antidiabetic and other health-related effects of honey will stimulate a renewed research interest in this field. Full article
Open AccessReview Recent Applications of the (TMS)3SiH Radical-Based Reagent
Molecules 2012, 17(1), 527-555; doi:10.3390/molecules17010527
Received: 29 November 2011 / Revised: 29 December 2011 / Accepted: 2 January 2012 / Published: 6 January 2012
Cited by 26 | PDF Full-text (582 KB)
Abstract
This review article focuses on the recent applications of tris(trimethylsilyl)silane as a radical-based reagent in organic chemistry. Numerous examples of the successful use of (TMS)3SiH in radical reductions, hydrosilylation and consecutive radical reactions are given. The use of (TMS)3 [...] Read more.
This review article focuses on the recent applications of tris(trimethylsilyl)silane as a radical-based reagent in organic chemistry. Numerous examples of the successful use of (TMS)3SiH in radical reductions, hydrosilylation and consecutive radical reactions are given. The use of (TMS)3SiH allows reactions to be carried out under mild conditions with excellent yields of products and remarkable chemo-, regio-, and stereoselectivity. The strategic role of (TMS)3SiH in polymerization is underlined with emphasis on the photo-induced radical polymerization of olefins and photo-promoted cationic polymerization of epoxides. Full article
(This article belongs to the Special Issue Organosilicon Chemistry)
Open AccessReview Mixed Biopolymer Systems Based on Starch
Molecules 2012, 17(1), 584-597; doi:10.3390/molecules17010584
Received: 14 November 2011 / Revised: 23 December 2011 / Accepted: 26 December 2011 / Published: 9 January 2012
Cited by 6 | PDF Full-text (398 KB)
Abstract
A binary mixture of starch–starch or starch with other biopolymers such as protein and non-starch polysaccharides could provide a new approach in producing starch-based food products. In the context of food processing, a specific adjustment in the rheological properties plays an important [...] Read more.
A binary mixture of starch–starch or starch with other biopolymers such as protein and non-starch polysaccharides could provide a new approach in producing starch-based food products. In the context of food processing, a specific adjustment in the rheological properties plays an important role in regulating production processing and optimizing the applicability, stability, and sensory of the final food products. This review examines various biopolymer mixtures based on starch and the influence of their interaction on physicochemical and rheological properties of the starch-based foods. It is evident that the physicochemical and rheological characteristics of the biopolymers mixture are highly dependent on the type of starch and other biopolymers that make them up mixing ratios, mixing procedure and presence of other food ingredients in the mixture. Understanding these properties will lead to improve the formulation of starch–based foods and minimize the need to resort to chemically modified starch. Full article
(This article belongs to the Special Issue Natural Polysaccharides: Chemistry, Bioactivity and Analysis)
Open AccessReview Oligothiophenes as Fluorescent Markers for Biological Applications
Molecules 2012, 17(1), 910-933; doi:10.3390/molecules17010910
Received: 2 December 2011 / Revised: 4 January 2012 / Accepted: 9 January 2012 / Published: 18 January 2012
Cited by 19 | PDF Full-text (1216 KB)
Abstract
This paper summarizes some of our results on the application of oligothiophenes as fluorescent markers for biological studies. The oligomers of thiophene, widely known for their semiconductor properties in organic electronics, are also fluorescent compounds characterized by chemical and optical stability, high [...] Read more.
This paper summarizes some of our results on the application of oligothiophenes as fluorescent markers for biological studies. The oligomers of thiophene, widely known for their semiconductor properties in organic electronics, are also fluorescent compounds characterized by chemical and optical stability, high absorbance and quantum yield. Their fluorescent emission can be easily modulated via organic synthesis by changing the number of thiophene rings and the nature of side-chains. This review shows how oligothiophenes can be derivatized with active groups such as phosphoramidite, N-hydroxysuccinimidyl and 4-sulfotetrafluorophenyl esters, isothiocyanate and azide by which the (bio)molecules of interest can be covalently bound. This paper also describes how molecules such as oligonucleotides, proteins and even nanoparticles, tagged with oligothiophenes, can be used in experiments ranging from hybridization studies to imaging of fixed and living cells. Finally, a few multilabeling experiments are described. Full article
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Open AccessReview Diversity Oriented Syntheses of Conventional Heterocycles by Smart Multi Component Reactions (MCRs) of the Last Decade
Molecules 2012, 17(1), 1074-1102; doi:10.3390/molecules17011074
Received: 9 December 2011 / Revised: 11 January 2012 / Accepted: 12 January 2012 / Published: 20 January 2012
Cited by 80 | PDF Full-text (964 KB)
Abstract
A collection of smart multicomponent reactions (MCRs) with continuative post condensation cyclizations (PCCs) is presented to construct conventional three- to seven-membered heterocyclic compounds in diversity oriented syntheses (DOS). These will provide a high degree of applying economical and ecological advantages as well [...] Read more.
A collection of smart multicomponent reactions (MCRs) with continuative post condensation cyclizations (PCCs) is presented to construct conventional three- to seven-membered heterocyclic compounds in diversity oriented syntheses (DOS). These will provide a high degree of applying economical and ecological advantages as well as of practicability. Water, ionic liquids, and solvent-less syntheses as well as use of various forms of energy as microwave and ultrasonic irradiation are examined and discussed. Full article
(This article belongs to the Special Issue Multicomponent Reaction)
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