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Molecules

 
Articles from the last few issues of Molecules
 

Efficient Synthesis of Unprotected C-5-Aryl/Heteroaryl-2'-deoxyuridine via a Suzuki-Miyaura Reaction in Aqueous Media

  [CiTO]
Molecules, Vol. 17, No. 12. (05 December 2012), pp. 14409-14417, doi:10.3390/molecules171214409

Abstract

Following our previous results on an environmentally benign one-pot Sonogashira-cyclization protocol to obtain substituted furopyrimidine nucleosides under aqueous conditions, we investigate herein the Suzuki-Miyaura cross-coupling reactions of aryl and heteroaryl derivatives at the C5 position of unprotected 2'-deoxyuridine in the same media with a common catalyst system avoiding exotic ligands, since palladium acetate and triphenylphosphine afforded the expected products in moderate to good yields. ...

 

Production of Volatile Compounds in Reconstituted Milk Reduced-Fat Cheese and the Physicochemical Properties as Affected by Exopolysaccharide-Producing Strain

  [CiTO]
Molecules, Vol. 17, No. 12. (05 December 2012), pp. 14393-14408, doi:10.3390/molecules171214393

Abstract

The application of the exopolysaccharide-producing strains for improving the texture and technical properties of reduced-fat cheese looks very promising. Streptococcus thermophilus TM11 was evaluated for production of reduced-fat cheese using reconstituted milk powder (CRMP). The physicochemical analysis of fresh and stored cheeses showed that this strain slightly increased moisture content resulting in cheese with higher yield and lower protein content compared to the direct acidified cheese. The volatiles of cheese were determined by SPME and GC equipped with a mass spectrometer. ...

 

Formation of Sulfonyl Aromatic Alcohols by Electrolysis of a Bisazo Reactive Dye

  [CiTO]
Molecules, Vol. 17, No. 12. (05 December 2012), pp. 14377-14392, doi:10.3390/molecules171214377

Abstract

Five sulfonyl aromatic alcohols, namely 4-((2-hydroxyethyl)sulfonyl)phenol, 4-((2-(2-((4-hydroxyphenyl)sulfonyl)ethoxy)vinyl)sulfonyl)phenol, 4-(ethylsulfonyl)phenol, 4-(vinylsulfonyl)phenol and 5-((4-aminophenyl)sulfonyl)-2-penten-1-ol were identified by LC-ESI-Qq-TOF-MS as products formed by electrolysis of the bisazo reactive dye Reactive Black 5 (RB5). Since electrolyses were performed in an undivided cell equipped with Ni electrodes in alkaline medium, amines like 4-(2-methoxyethylsulfonyl)benzene-amine (MEBA) with m/z 216 were also suspected to be formed due to the plausible chemical reaction in the bulk or the cathodic reduction of RB5 and its oxidation by-products. Aiming to check this ...

 

Oxime-Based Carbonates as Useful Reagents for Both N-Protection and Peptide Coupling

  [CiTO]
Molecules, Vol. 17, No. 12. (05 December 2012), pp. 14361-14376, doi:10.3390/molecules171214361

Abstract

We have demonstrated that oxime-based mixed carbonates are very effective reagents for both N-protection and peptide coupling. ...

 

Assessment of the in Vitro Antiprotozoal and Cytotoxic Potential of 20 Selected Medicinal Plants from the Island of Soqotra

  [CiTO]
Molecules, Vol. 17, No. 12. (03 December 2012), pp. 14349-14360, doi:10.3390/molecules171214349

Abstract

Malaria, leishmaniasis and human African trypanosomiasis continue to be major public health problems in need of new and more effective drugs. The aim of this study was to evaluate in vitro antiprotozoal activity of twenty endemic medicinal plants collected from the island of Soqotra in the Indian Ocean. The plant materials were extracted with methanol and tested for antiplasmodial activity against erythrocytic schizonts of Plasmodium falciparum, for antileishmanial activity against intracellular amastigotes of Leishmania infantum and for antitrypanosomal activity against intracellular ...

 

In Vitro Antioxidant Activities of Three Red Wine Polyphenols and Their Mixtures: An Interaction Study

  [CiTO]
Molecules, Vol. 17, No. 12. (03 December 2012), pp. 14336-14348, doi:10.3390/molecules171214336

Abstract

The well-known antioxidant activity of red wine is explained mostly by its polyphenols content, where the final effect is based on the wine components’ interaction. The aim of our work was the study of the interaction of three red wine polyphenols—quercetin, resveratrol and caffeic acid—alone and in their equimolar binary and ternary mixtures in different antioxidant/scavenging assays (inhibition of 2-deoxy-D-ribose degradation by hydroxyl radical, FRAP, Fe(III) reducing power, DPPH, ABTS and NO scavenging, respectively). Interaction analysis, based on median effect equation, ...

 

Ionic Liquid-Based Microwave-Assisted Extraction of Flavonoids from Bauhinia championii (Benth.) Benth.

  [CiTO]
Molecules, Vol. 17, No. 12. (03 December 2012), pp. 14323-14335, doi:10.3390/molecules171214323

Abstract

An ionic liquids (IL)-based microwave-assisted approach for extraction and determination of flavonoids from Bauhinia championii (Benth.) Benth. was proposed for the first time. Several ILs with different cations and anions and the microwave-assisted extraction (MAE) conditions, including sample particle size, extraction time and liquid-solid ratio, were investigated. Two M 1-butyl-3-methylimidazolium bromide ([bmim] Br) solution with 0.80 M HCl was selected as the optimal solvent. Meanwhile the optimized conditions a ratio of liquid to material of 30:1, and the extraction for ...

 

Antimicrobial and Cytotoxic Isohexenylnaphthazarins from Arnebia euchroma (Royle) Jonst. (Boraginaceae) Callus and Cell Suspension Culture

  [CiTO]
Molecules, Vol. 17, No. 12. (03 December 2012), pp. 14310-14322, doi:10.3390/molecules171214310

Abstract

The phytochemical investigation of the n-hexane extract from callus and cell suspension culture of Arnebia euchroma (Royle) Jonst. resulted in the isolation of nine isohexenylnaphthazarins: deoxyalkannin (1), alkannin (2), acetylalkannin (3), isobutyrylalkannin (4), β-hydroxyisovalerylalkannin (5), 2”-(S)-α-methylbutyrylalkannin (6), propionylalkannin (7), teracrylalkannin (8) and acetylshikonin (9). Their structures were determined by MS and NMR spectroscopy. Pigments 2–8 are isolated for the first time from Arnebia in vitro cultures, 4 and 7 are reported in the present work as novel metabolites within the Arnebia ...

 

Toxicological Assessment of β-(1à6)-Glucan (Lasiodiplodan) in Mice during a 28-Day Feeding Study by Gavage

  [CiTO]
Molecules, Vol. 17, No. 12. (03 December 2012), pp. 14298-14309, doi:10.3390/molecules171214298

Abstract

Studies evaluating the toxicity caused by fungal exopolysaccharides of the β-(1®6)-D-glucan type are rare. In this study, the toxicological effects of sub-chronic treatments with lasiodiplodan (β-(1®6)-D-glucan from Lasiodiplodia theobromae MMPI) were evaluated in mice through the assessment of biochemical, hematological, and histopathological alterations. Thirty-two mice (16 male, 16 female) were used in this study divided in two groups; one group received lasiodiplodan (50 mg/kg body weight) daily for 28 days via gavage, and another (control group) received saline during the ...

 

A Facile Synthesis for Novel Loperamide Analogs as Potential μ Opioid Receptor Agonists

  [CiTO]
Molecules, Vol. 17, No. 12. (03 December 2012), pp. 14288-14297, doi:10.3390/molecules171214288

Abstract

A facile synthesis for novel loperamide analogs as potential μ opioid receptors is described. The synthetic procedure for compound 5, which contains two 4-phenyl piperidine scaffolds, was optimized, and this compound was synthesized in excellent yield. We also describe a mild and highly efficient protocol for the synthesis of compounds 6 and 7. ...

 

In Vitro Antimicrobial, Antioxidant, Cytotoxicity and GC-MS Analysis of Mazus goodenifolius

  [CiTO]
Molecules, Vol. 17, No. 12. (03 December 2012), pp. 14275-14287, doi:10.3390/molecules171214275

Abstract

The antimicrobial, antioxidant and cytotoxic properties of Mazus goodenifolius (Hornem.) Pennell essential oil, methanol extract and some solvent-extracted subfractions of the latter were appraised. A qualitative, quantitative analysis of the classes of phytochemicals in the various fractions and GC-MS analysis of the essential oil was carried out. The activity of the plant extract and various subfractions against selected bacterial (Pasturella multocida, Escherichia coli, Bacillus subtilis and Staphylococcus aureus) and fungal strains (Aspergillus niger, Aspergillus flavus, Alternaria alternata and Rhizopus solani) was ...

 

Textile Dye Removal from Wastewater Effluents Using Bioflocculants Produced by Indigenous Bacterial Isolates

  [CiTO]
Molecules, Vol. 17, No. 12. (30 November 2012), pp. 14260-14274, doi:10.3390/molecules171214260

Abstract

Bioflocculant-producing bacteria were isolated from activated sludge of a wastewater treatment plant located in Durban, South Africa, and identified using standard biochemical tests as well as the analysis of their 16S rRNA gene sequences. The bioflocculants produced by these organisms were ethanol precipitated, purified using 2% (w/v) cetylpyridinium chloride solution and evaluated for removal of wastewater dyes under different pH, temperature and nutritional conditions. Bioflocculants from these indigenous bacteria were very effective for decolourizing the different dyes tested in this study, ...

 

Recent Developments in the Reformatsky-Claisen Rearrangement

  [CiTO]
Molecules, Vol. 17, No. 12. (30 November 2012), pp. 14249-14259, doi:10.3390/molecules171214249

Abstract

The rearrangement of allyl a-bromoacetates with Zn dust is known as the Reformatsky-Claisen rearrangement. Whereas the Ireland-Claisen rearrangement has been widely used in the synthesis of a diverse range of natural products, the Zn-mediated Reformatsky-Claisen rearrangement has not been utilized so often. In this article, we will provide an overview of recent advances in the Reformatsky-Claisen rearrangement field, including the In-mediated Reformatsky-Claisen rearrangement we have recently developed. ...

 

Peptide-Based Selective Inhibitors of Matrix Metalloproteinase-Mediated Activities

  [CiTO]
Molecules, Vol. 17, No. 12. (30 November 2012), pp. 14230-14248, doi:10.3390/molecules171214230

Abstract

The matrix metalloproteinases (MMPs) exhibit a broad array of activities, some catalytic and some non-catalytic in nature. An overall lack of selectivity has rendered small molecule, active site targeted MMP inhibitors problematic in execution. Inhibitors that favor few or individual members of the MMP family often take advantage of interactions outside the enzyme active site. We presently focus on peptide-based MMP inhibitors and probes that do not incorporate conventional Zn2+ binding groups. In some cases, these inhibitors and probes function by ...

 

An Improved Method for Removal of Azo Dye Orange II from Textile Effluent Using Albumin as Sorbent

  [CiTO]
Molecules, Vol. 17, No. 12. (30 November 2012), pp. 14219-14229, doi:10.3390/molecules171214219

Abstract

Azo dyes are generally resistant to biodegradation due to their complex structures. Acid orange II is one of the most widely used dyes in the textile industry. The influence of bovine serum albumin (BSA) in different concentrations, pH, and time of contact on Orange II was investigated using kinetics and adsorption-isotherm experiments. The results showed that the maximum colour removed from dye/albumin was 99.50% and that a stable dye-protein complex had been formed at pH 3.5 and in a proportion of ...

 

Synthesis and Antifungal Activity of N-(Substituted pyridinyl)-1-methyl(phenyl)-3-(trifluoromethyl)-1H-pyrazole-4-carboxamide Derivatives

  [CiTO]
Molecules, Vol. 17, No. 12. (30 November 2012), pp. 14205-14218, doi:10.3390/molecules171214205

Abstract

A series of N-(substituted pyridinyl)-1-methyl(phenyl)-3-trifluoromethyl-1H-pyrazole-4-carboxamide derivatives were synthesized. All target compounds were characterized by spectral data (1H-NMR, 13C-NMR, IR, MS) and elemental analysis and were bioassayed in vitro against three kinds of phytopathogenic fungi (Gibberella zeae, Fusarium oxysporum, Cytospora mandshurica). The results showed that some of the synthesized N-(substituted pyridinyl)-1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxamides exhibited moderate antifungal activities, among which compounds 6a, 6b and 6c displayed more than 50% inhibition activities against G. zeae at 100 µg/mL, which was better than that of the commercial ...

 

Synthesis and Photophysical Properties of 2-Aryl-6,8-bis(arylethenyl)-4-methoxyquinolines

  [CiTO]
Molecules, Vol. 17, No. 12. (30 November 2012), pp. 14186-14204, doi:10.3390/molecules171214186

Abstract

Iodine-methanol mediated oxidative-aromatization of 2-aryl-6,8-dibromo-2,3-dihydroquinolin-4(1H)-ones afforded the corresponding 2-aryl-6,8-dibromo-4-methoxy-quinolines in high yield and purity. The isomeric 1-(2-amino-3,5-dibromophenyl)-3-aryl-2-propen-1-ones reacted with iodine in methanol afford in a single pot operation the corresponding 2-aryl-6,8-dibromo-4-methoxyquinoline (major) and 2-aryl-6,8-dibromoquinolin-4(1H)-one (minor) products that were separated in sequence by column chromatography on silica gel. Suzuki-Miyaura cross-coupling of the 6,8-dibromo-4-methoxyquinoline derivatives with excess arylvinylboronic acids afforded the corresponding 2-aryl-6,8-bis(2-arylethenyl)-4-methoxyquinolines. The absorption and fluorescence properties of these compounds were also determined. ...

 

Synthesis of Biotin Linkers with the Activated Triple Bond Donor [p-(N-propynoylamino)toluic Acid] (PATA) for Efficient Biotinylation of Peptides and Oligonucleotides

  [CiTO]
Molecules, Vol. 17, No. 12. (30 November 2012), pp. 14174-14185, doi:10.3390/molecules171214174

Abstract

Biotin is an important molecule for modern biological studies including, e.g., cellular transport. Its exclusive affinity to fluorescent streptavidin/avidin proteins allows ready and specific detection. As a consequence methods for the attachment of biotin to various biological targets are of high importance, especially when they are very selective and can also proceed in water. One useful method is Hüisgen dipolar [3+2]-cycloaddition, commonly referred to as “click chemistry”. As we reported recently, the activated triple bond donor p-(N-propynoylamino)toluic acid (PATA) gives excellent ...

 

Studies on the Interaction Mechanism of Pyrene Derivatives with Human Tumor-Related DNA

  [CiTO]
Molecules, Vol. 17, No. 12. (28 November 2012), pp. 14159-14173, doi:10.3390/molecules171214159

Abstract

Pyrene derivatives can be carcinogenic, teratogenic and mutagenic, thus having the potential to cause malignant diseases. In this work, the interactions of two selected pyrene derivatives (1-OHP and 1-PBO) and human tumor-related DNA (p53 DNA and C-myc DNA) are investigated by spectroscopic and non-native polyacrylamide gel electrophoresis (PAGE) methods. Using fluorescence spectrometry and circular dichroism (CD), DNA interactions of pyrene derivatives are confirmed to occur mainly via the groove binding mode supported by the intercalation into the base pairs of ...

 

Ultrasound-Promoted Greener Synthesis of Novel Trifurcate 3-Substituted-chroman-2,4-dione Derivatives and Their Drug-Likeness Evaluation

  [CiTO]
Molecules, Vol. 17, No. 12. (28 November 2012), pp. 14146-14158, doi:10.3390/molecules171214146

Abstract

An efficient and convenient approach for one-pot synthesis of 3-substituted chroman-2,4-diones via a three-component reaction of aromatic aldehydes, 4-hydroxy- coumarins and diverse pyrazolone derivatives was described. The combinatorial synthesis for this methodology was achieved by applying ultrasound irradiation in the absence of activator while making use of water as green solvent. Additionally, novel chroman-2,4-dione derivatives attached to an edaravone moiety represent an exploitable source of brand new anticancer agents. In comparison with conventional methods, experimental simplicity, good functional group tolerance, excellent ...

 

Design, Synthesis, Antinociceptive and Anti-Inflammatory Activities of Novel Piroxicam Analogues

  [CiTO]
Molecules, Vol. 17, No. 12. (28 November 2012), pp. 14126-14145, doi:10.3390/molecules171214126

Abstract

In this paper we report the design, synthesis, antinociceptive and anti-inflammatory activities of a series of benzothiazine N-acylhydrazones 14a–h, planned by structural modification of piroxicam (1), a non steroidal anti-inflammatory drug. Among the synthesized analogues, compounds 14f (LASSBio-1637) and 14g (LASSBio-1639) were identified as novel antinociceptive and anti-inflammatory prototypes, active by oral administration, acting by a mechanism of action that seems to be different from that of piroxicam, since they were inactive as an inhibitor of cyclooxygenase (COX-1 and COX-2) at ...

 

Study of the Volatile Constituents in Radix Flemingiae Macrophyllae and a Substitute by Gas Chromatography-Mass Spectrometry and Chemometric Methods

  [CiTO]
Molecules, Vol. 17, No. 12. (28 November 2012), pp. 14111-14125, doi:10.3390/molecules171214111

Abstract

A combined approach of subwindow factor analysis and spectral correlative chromatography was used to analyze the volatile components in Radix Flemingiae Macrophyllae and Flemingiae Latifolia Benth, one of its substitutes. After extraction by a water distillation method, the volatile components in Radix Flemingiae Macrophyllae and Flemingiae Latifolia Benth were detected by GC-MS. Then the qualitative and quantitative analysis of the volatile components in Radix Flemingiae Macrophyllae was completed with the help of subwindow factor analysis resolving two-dimensional original data into mass ...

 

Allylation of Functionalized Aldehydes by Potassium Allyltrifluoroborate Catalyzed by 18-Crown-6 in Aqueous Media

  [CiTO]
Molecules, Vol. 17, No. 12. (28 November 2012), pp. 14099-14110, doi:10.3390/molecules171214099

Abstract

An efficient method for the allylation of aldehydes containing a broad range of functional groups using potassium allyltrifluoroborate is described. The reaction utilizes a catalytic amount of 18-C-6 in biphasic media under open atmosphere and room temperature to provide the corresponding homoallylic alcohols in high yields and without the necessity of any subsequent purification. ...

 

Isolation, Identification and Antimicrobial Activities of Two Secondary Metabolites of Talaromyces verruculosus

  [CiTO]
Molecules, Vol. 17, No. 12. (28 November 2012), pp. 14091-14098, doi:10.3390/molecules171214091

Abstract

From the ethyl acetate extract of the culture broth of Talaromyces verruculosus, a rhizosphere fungus of Stellera chamaejasme L., (−)-8-hydroxy-3-(4-hydroxypentyl)-3,4-dihydroisocoumarin (1) and (E)-3-(2,5-dioxo-3-(propan-2-ylidene)pyrrolidin-1-yl)acrylic acid (2) were isolated and evaluated for their antimicrobial activities. Their structures were elucidated by UV, IR, MS, 1H-NMR, 13C-NMR and 2D NMR spectra. Compound 1 exhibited the significant activities in vitro against two strains of bacteria and four strains of fungi. Compound 2 gave slight activities on the fungi at 100 µg mL−1, but no activities on ...

 

Fluorescent Probes and Fluorescence (Microscopy) Techniques — Illuminating Biological and Biomedical Research

  [CiTO]
Molecules, Vol. 17, No. 12. (28 November 2012), pp. 14067-14090, doi:10.3390/molecules171214067

Abstract

Fluorescence, the absorption and re-emission of photons with longer wavelengths, is one of those amazing phenomena of Nature. Its discovery and utilization had, and still has, a major impact on biological and biomedical research, since it enables researchers not just to visualize normal physiological processes with high temporal and spatial resolution, to detect multiple signals concomitantly, to track single molecules in vivo, to replace radioactive assays when possible, but also to shed light on many pathobiological processes underpinning disease states, ...

 

Norcembranoidal Diterpenes from a Formosan Soft Coral Sinularia sp.

  [CiTO]
Molecules, Vol. 17, No. 12. (27 November 2012), pp. 14058-14066, doi:10.3390/molecules171214058

Abstract

Two norcembranoidal diterpenes, 5-episinuleptolide acetate (1) and scabrolide D (2), were isolated from a Formosan octocoral identified as Sinularia sp. The structures of norcembranoids 1 and 2 were established by spectroscopic methods and by comparison of the spectral data with those of known analogues and 1 was proven to be a new natural product. Norcembranoid 1 was found to exhibit cytotoxicity toward a panel of tumor cells. ...

 

4,5-Seco-Guaiane and a Nine-Membered Sesquiterpene Lactone from Holostylis reniformis

  [CiTO]
Molecules, Vol. 17, No. 12. (27 November 2012), pp. 14046-14057, doi:10.3390/molecules171214046

Abstract

Root extracts of Holostylis reniformis (Aristolochiaceae) yielded three new natural sesquiterpenes, a sesquiterpene with an unusual carbon skeleton, 4,5-seco-guaiane (7-epi-11-hydroxychabrolidione A, 1), a nine-membered lactone with new carbon skeleton (holostylactone, 2), and a new megastigmane [(6S,7E)-6,9-dihydroxy-10-(2'-hydroxy-ethoxy)-4,7-megastigmadien-3-one, 3], together with bulnesol and sitosterol-3-O-β-D-glucopyranoside. The structures of these compounds were determined by spectroscopic analyses and B3LYP/STO-3G** theoretical studies. ...

 

Antioxidant Phenolic Compounds from Pu-erh Tea

  [CiTO]
Molecules, Vol. 17, No. 12. (27 November 2012), pp. 14037-14045, doi:10.3390/molecules171214037

Abstract

Eight compounds were isolated from the water extract of Pu-erh tea and their structures were elucidated by NMR and MS as gallic acid (1), (+)-catechin (2), (−)-epicatechin (3), (−)-epicatechin-3-O-gallate (4), (−)-epigallocatechin-3-O-gallate (5), (−)-epiafzelechin- 3-O-gallate (6), kaempferol (7), and quercetin (8). Their in vitro antioxidant activities were assessed by the DPPH and ABTS scavenging methods with microplate assays. The relative order of DPPH scavenging capacity for these compounds was compound 8 > compound 7 > compound 1 > compound 6 > compound ...

 

Antifungal Activity of Homoaconitate and Homoisocitrate Analogs

  [CiTO]
Molecules, Vol. 17, No. 12. (27 November 2012), pp. 14022-14036, doi:10.3390/molecules171214022

Abstract

Thirteen structural analogs of two initial intermediates of the L-a-aminoadipate pathway of L-lysine biosynthesis in fungi have been designed and synthesized, including fluoro- and epoxy-derivatives of homoaconitate and homoisocitrate. Some of the obtained compounds exhibited at milimolar range moderate enzyme inhibitory properties against homoaconitase and/or homoisocitrate dehydrogenase of Candida albicans. The structural basis for homoisocitrate dehydrogenase inhibition was revealed by molecular modeling of the enzyme-inhibitor complex. On the other hand, the trimethyl ester forms of some of the novel compounds exhibited ...

 

New Furanones from the Plant Endophytic Fungus Pestalotiopsis besseyi

  [CiTO]
Molecules, Vol. 17, No. 12. (27 November 2012), pp. 14015-14021, doi:10.3390/molecules171214015

Abstract

Pestalafuranones A–E (compounds 1–5), five new 2(5H)-furanones, have been isolated from cultures of an isolate of Pestalotiopsis besseyi. The structures of these compounds were elucidated mainly by analysis of their NMR spectroscopic data and HRESIMS experiments. Pestalafuranones A–C (compounds 1–3) displayed weak inhibitory effects against HIV-1 replication in C8166 cells, whereas pestalafuranones D (4) and E (5) showed moderate antifungal activity against the plant pathogens Verticillium dahiae and Alternaria longipes. ...

 

Novel Steroidal Components from the Underground Parts of Ruscus aculeatus L.

  [CiTO]
Molecules, Vol. 17, No. 12. (26 November 2012), pp. 14002-14014, doi:10.3390/molecules171214002

Abstract

Two new furostanol saponins 1–2 and three new sulphated glycosides 3a,b and 4 were isolated from the underground parts of Ruscus aculeatus L., along with four known furostanol and one spirostanol saponins 5–9 and three free sterols. All of the structures have been elucidated on the basis of spectroscopic data 1D and 2D NMR experiments, MS spectra and GC analyses. ...

 

Synthesis and Insecticidal Activity of an Oxabicyclolactone and Novel Pyrethroids

  [CiTO]
Molecules, Vol. 17, No. 12. (26 November 2012), pp. 13989-14001, doi:10.3390/molecules171213989

Abstract

Deltamethrin, a member of the pyrethroids, one of the safest classes of pesticides, is among some of the most popular and widely used insecticides in the World. Our objective was to synthesize an oxabicyclolactone 6 and five novel pyrethroids 8–12 from readily available furfural and D-mannitol, respectively, and evaluate their biological activity against four insect species of economic importance namely A. obtectus, S. zeamais, A. monuste orseis, and P. americana. A concise and novel synthesis of 6,6-dimethyl-3-oxabicyclo[3.1.0]hexan-2-one (6) from furfural is ...

 

Novel Self-Dyed Wholly Aromatic Polyamide-Hydrazides Covalently Bonded with Azo Groups in Their Main Chains: 1. Structure-Property Relationships

  [CiTO]
Molecules, Vol. 17, No. 12. (26 November 2012), pp. 13969-13988, doi:10.3390/molecules171213969

Abstract

Twelve novel intrinsically colored wholly aromatic azopolyamide-hydrazides containing various proportions of para- and meta-phenylene units were successfully synthesized by a low temperature (−10 °C) solution polycondensation reaction of either 4-amino-3-hydroxybenzhydrazide (4A3HBH) or 3-amino-4-hydroxybenzhydrazide (3A4HBH) with an equimolar amount of either 4,4'-azodibenzoyl chloride (4,4'ADBC), 3,3'-azodibenzoyl chloride (3,3'ADBC), or mixtures of various molar ratios of 4,4'ADBC and 3,3'ADBC in anhydrous N,N-dimethyl acetamide (DMAc) containing 3% (wt/v) LiCl as a solvent. The structures of the polymers were proven by elemental analysis, FTIR, 1H- ...

 

A New Ursane-Type Nor-Triterpenoid from the Leaves of Eucommia ulmoides Oliv.

  [CiTO]
Molecules, Vol. 17, No. 12. (26 November 2012), pp. 13960-13968, doi:10.3390/molecules171213960

Abstract

A new ursane-type nortriterpenoid, (11S,12S)-4-methyl-11,12-epoxy-2-hydroxy-3-oxoursa-1,4-dine-28-oic acid γ-lactone (1), named ulmoidol A, together with ten known compounds: ulmoidol (2), corosolic acid (3), 2α,3α-dihydroxy-24-nor-4(23),12-oleanadien-28-oic acid (4), oleanolic acid (5), ursolic acid (6), cycloart-3β, 25-diol (7), foliasalacioside B1 (8), (6R,7E,9R)-9-hydroxy-4,7-megastigmadien-3-one-9-O-α-L-arabinopyranosyl-(1→6)-β-D-glucopyranoside (9), (6R,7E,9R)-9-hydroxy-4,7-megastigma-dien-3-one-9-O-β-D-xylopyranosyl-(1→6)-β-D-glucopyranoside (10), and quercetin 3-O-sambubioside (11) were isolated from the leaves of Eucommia ulmoides Oliv. The structure of compound 1 was determined by extensive spectroscopic analysis, and its absolute configuration was determined by CD experiments and a computational method. Compounds 3, 4, 7–10 ...

 

A Comparative Uptake Study of Multiplexed PET Tracers in Mice with Turpentine-Induced Inflammation

  [CiTO]
Molecules, Vol. 17, No. 12. (26 November 2012), pp. 13948-13959, doi:10.3390/molecules171213948

Abstract

The potential value of multiplexed positron emission tomography (PET) tracers in mice with turpentine-induced inflammation was evaluated and compared with 2-[18F]fluoro-2-deoxy-D-glucose ([18F]FDG) for glucose metabolism imaging. These PET tracers included [18F]fluoromethylcholine ([18F]FCH) for choline metabolism imaging, (S-[11C]methyl)-D-cysteine ([11C]DMCYS) for amino acid metabolism imaging, [11C]bis(zinc(II)-dipicolylamine) ([11C]DPA-Zn2+) for apoptosis imaging, 2-(4-N-[11C]-methylaminophenyl)-6-hydroxybenzothiazole ([11C]PIB) for β amyloid binding imaging, and [18F]fluoride (18F−) for bone metabolism imaging. In mice with turpentine-induced inflammation mice, the biodistribution of all the tracers mentioned above at 5, 15, ...

 

Evaluation of the Hepatoprotective Effects of Lantadene A, a Pentacyclic Triterpenoid of Lantana Plants against Acetaminophen-induced Liver Damage

  [CiTO]
Molecules, Vol. 17, No. 12. (23 November 2012), pp. 13937-13947, doi:10.3390/molecules171213937

Abstract

The aim of the present study was to evaluate the hepatoprotective activity of lantadene A against acetaminophen-induced liver toxicity in mice was studied. Activity was measured by monitoring the levels of aspartate aminotransferase (AST), alanine aminotransferase (ALT), alkaline phosphatase (ALP) and bilirubin, along with histo-pathological analysis. Silymarin was used as positive control. A bimodal pattern of behavioural toxicity was exhibited by the lantadene A-treated group at the beginning of the treatment. However, treatment with lantadene A and silymarin resulted in an ...

 

Subnanosecond Charge Recombination Dynamics in P3HT/PC61BM Films

  [CiTO]
Molecules, Vol. 17, No. 12. (23 November 2012), pp. 13923-13936, doi:10.3390/molecules171213923

Abstract

Ultrafast near-infrared absorption spectroscopy was used to investigate the influence of film morphology and excitation photon energy on the charge recombination (CR) dynamics in the initial nanosecond timescale in the P3HT/PC61BM blend films. With reference to the CS2-cast films, the solvent vapor annealed (SVA) ones show 2–3-fold improvement in hole mobility and more than 5-fold reduction in the polymer-localized trap states of holes. At Dt = 70 ps, the hole mobility (mh) and the bimolecular CR rate (gbi) of the SVA ...

 

Isolation and Identification of the Phenolic Compounds from the Roots of Sanguisorba officinalis L. and Their Antioxidant Activities

  [CiTO]
Molecules, Vol. 17, No. 12. (23 November 2012), pp. 13917-13922, doi:10.3390/molecules171213917

Abstract

Four phenolic compounds were isolated from the roots of Sanguisorba officinalis L. by silica gel column chromatography and preparative HPLC. On the basis of chemical and spectroscopic methods, their structures were identified as methyl 4-O-β-D-glucopyranosy-5-hydroxy-3-methoxylbenzoate (1), 3,3′,4′-tri-O-methylellagic acid (2), fisetinidol-(4α-8)-catechin (3), and (+)-catechin (4). Compound 1 is a new phenolic glycoside and compounds 2 and 3 were isolated from the Sanguisorba genus for the first time. Compounds 1–4 were also assayed for their antioxidant activities using the DPPH free radical assay. ...

 

A New Prenylated Naphthoquinoid from the Aerial Parts of Clinopodium chinense (Benth.) O. Kuntze

  [CiTO]
Molecules, Vol. 17, No. 12. (23 November 2012), pp. 13910-13916, doi:10.3390/molecules171213910

Abstract

A new prenylated naphthoquinoid, named (3R,4aR,10bR)-3,10-dihydroxy-2,2-dimethyl-3,4,4a,10b-tetrahydro-2H-naphtho[1,2-b]-pyran-5H-6-one (1), was isolated from the aerial parts of Clinopodium chinense (Benth.) O. Kuntze, together with six known compounds: apigenin (2), luteolin (3), neoeriocitrin (4), naringenin (5), narirutin (6), and didymin (7). Neoeriocitrin was isolated for the first time from the species C. chinense. Their structures were elucidated by spectroscopic methods, including 1D, 2D (1H-1H-COSY, HSQC, HMBC and NOESY) NMR, HR-ESI-MS. The absolute configuration of 1 was determinated using the CD method. We highlight that the ...

 

A Facile Synthesis of New Monoazo Disperse Dyes Derived from 4-Hydroxyphenylazopyrazole-5-amines: Evaluation of Microwave Assisted Dyeing Behavior

  [CiTO]
Molecules, Vol. 17, No. 12. (23 November 2012), pp. 13891-13909, doi:10.3390/molecules171213891

Abstract

A series of new monoazo disperse dyes containing pyrazolopyrimidine moieties was synthesized by coupling malononitrile or 3-aminocrotononitrile with 4-hydroxy- benzenediazonium chloride. Treatment of the resulting products with hydrazine hydrate yields the corresponding 4-arylazoaminopyrazoles, which then react with either 2,4-pentanedione and enaminonitriles or aryl-substituted enaminoketones to give the target pyrazolopyrimidine monoazo disperse dyes. Structural assignments of the dyes were made using both NMR spectroscopic and X-ray crystallographic methods. A high temperature dyeing method, by microwave irradiation, was employed with polyester fabrics. ...

 

Novel Rearrangements in the Reactions Directed Toward Preparation of Spiro-N,N-ketals: Reactions of Naphthalene-1,8-diamine with Ninhydrin and Isatin

  [CiTO]
Molecules, Vol. 17, No. 12. (22 November 2012), pp. 13879-13890, doi:10.3390/molecules171213879

Abstract

Spiro-N,N-ketal 5, consisting of a phthaloperine heterocyclic ring and a naphtha[1,8-ef][1,4]diazepine ring, was obtained along with spiro-N,N-ketal 2 via 2,2-condensation in the reaction of ninhydrin with naphthalene-1,8-diamine. Their molecular structures were elucidated by X-ray crystal structural analysis. Aside from these spiro compounds, the diazapleiadiene compound 3 formed by 1,2-condensation and the 1,4-isoquinolinedione compound 4 arising from ring expansion were isolated. When isatin was reacted with naphthalene-1,8-diamine, spiro-N,N-ketal 6 and the two 1H-perimidine-based compounds 7 and 8 were isolated. Compound ...

 

Efficient Preparation of α-Ketoacetals

  [CiTO]
Molecules, Vol. 17, No. 12. (22 November 2012), pp. 13864-13878, doi:10.3390/molecules171213864

Abstract

The Weinreb amides 2a,b were prepared from the α,α-dimethoxyacetic acids 1c,d. A number of representative nucleophilic additions (RMgX and RLi) on 2 afforded α-ketoacetals 3a–j in 70–99% yield. These compounds represent a versatile arrangement of functional groups of significant synthetic value, as demonstrated in the synthesis of (±)-salbutamol. ...

 

An Efficient One-Pot Synthesis of Pyrano[3,2-c]quinolin-2,5-dione Derivatives Catalyzed by L-Proline

  [CiTO]
Molecules, Vol. 17, No. 12. (22 November 2012), pp. 13856-13863, doi:10.3390/molecules171213856

Abstract

A series of 4-aryl-6-methyl-3,4-dihydro-2H-pyrano[3,2-c]quinolin-2,5(6H)-diones were synthesized via the three-component reactions of aromatic aldehydes, 4-hydroxy-1-methylquinolin-2(1H)-one, and Meldrum’s acid catalyzed by L-proline. The structures of the products were identified by spectroscopic analysis. A mechanism for this three-component reaction catalyzed by L-proline was proposed. ...

 

Influence of Nonpolar Substances on the Extraction Efficiency of Six Alkaloids in Zoagumhwan Investigated by Ultra Performance Liquid Chromatography and Photodiode Array Detection

  [CiTO]
Molecules, Vol. 17, No. 12. (22 November 2012), pp. 13844-13855, doi:10.3390/molecules171213844

Abstract

A reverse phase ultra performance liquid chromatography and photodiode array (UPLC-PDA) detection method was established for the determination of six alkaloids in Zoagumhwan (ZGW), and further for investigating the influence of nonpolar substances on the extraction efficiency of these alkaloids. The method was based on a BEH C18 (50 mm × 2.1 mm, 1.7 μm) column and mobile phase of aqueous phosphoric acid and acetonitrile including 0.05% buffer solution under gradient elution. ZGW samples of ZGW I, II, III and ...

 

Oligonucleotide-Peptide Conjugates: Solid-Phase Synthesis under Acidic Conditions and Use in ELISA Assays

  [CiTO]
Molecules, Vol. 17, No. 12. (22 November 2012), pp. 13825-13843, doi:10.3390/molecules171213825

Abstract

Here we used solid-phase methods to prepare oligonucleotides carrying fibrin/ filaggrin citrullinated peptides. Post-synthetic conjugation protocols were successfully applied for the synthesis of oligonucleotides carrying small peptides. A stepwise protocol using acid treatment for the final deprotection allowed the preparation of polypyrimidine oligonucleotides carrying longer and arginine-rich peptides. An ELISA-based test using the oligonucleotide-citrullinated peptide conjugates was developed for the detection of anti-citrullinated protein/peptide antibodies in human serum from rheumatoid arthritis patients. ...

 

Lipases as Tools in the Synthesis of Prodrugs from Racemic 9-(2,3-Dihydroxypropyl)adenine

  [CiTO]
Molecules, Vol. 17, No. 12. (22 November 2012), pp. 13813-13824, doi:10.3390/molecules171213813

Abstract

Lipases from Geotrichum candidum 4013 (extracellular lipase and cell-bound lipase) were immobilized by adsorption on chitosan beads. The enzyme preparations were tested in the synthesis of ester prodrugs from racemic 9-(2,3-dihydroxypropyl)adenine in dimethylformamide with different vinyl esters (acetate, butyrate, decanoate, laurate, palmitate). The transesterification activities of these immobilized enzymes were compared with commercially available lipases (lipase from hog pancreas, Aspergillus niger, Candida antarctica, Pseudomonas fluorescens). Lipase from Candida antarctica was found to be the most efficient enzyme regarding chemical yield of ...

 

Headspace Solid-Phase Microextraction Gas Chromatography-Mass Spectrometry and Gas Chromatography-Olfactometry Analysis of Volatile Compounds in Pineapple Breads

  [CiTO]
Molecules, Vol. 17, No. 12. (22 November 2012), pp. 13795-13812, doi:10.3390/molecules171213795

Abstract

Sensorial analysis of pineapple breads (conventionally baked, Cpb; fully baked frozen, Fpb and partially baked, Ppb) showed no significant differences in terms of aroma and taste. On the contrary, the scores for the overall quality between the partially baked and conventionally baked breads showed significant (p < 0.05) differences. At the same time, headspace analysis using a solid-phase microextraction (SPME) method identified 59 volatile compounds. The results of the aroma extracts dilution analysis (AEDA) revealed 19 most odour-active compounds with ...

 

Spiroheterocyclization of Methyl 1-Aryl-3-cinnamoyl-4,5-dioxo-4,5-dihydro-1H-pyrrole-2-carboxylates by the Action of 3-(Arylamino)-1H-inden-1-ones

  [CiTO]
Molecules, Vol. 17, No. 12. (22 November 2012), pp. 13787-13794, doi:10.3390/molecules171213787

Abstract

Methyl 1-aryl-3-cinnamoyl-4,5-dioxo-4,5-dihydro-1H-pyrrole-2-carboxylates interact with 3-(arylamino)-1H-inden-1-ones to give the corresponding 1,1'-diaryl-3'-cinnamoyl-4'-hydroxy-1H-spiro[indeno[1,2-b]pyrrole-3,2'-pyrrole]-2,4,5'(1'H)-triones in good yields. ...

 

Red Ginseng Marc Oil Inhibits iNOS and COX-2 via NFκB and p38 Pathways in LPS-Stimulated RAW 264.7 Macrophages

  [CiTO]
Molecules, Vol. 17, No. 12. (22 November 2012), pp. 13769-13786, doi:10.3390/molecules171213769

Abstract

In this study, we investigated the anti-inflammatory effects of red ginseng marc oil (RMO) in the RAW 264.7 macrophage cell line. RMO was prepared by a supercritical CO2 extraction of waste product generated after hot water extraction of red ginseng. RMO significantly inhibited the production of oxidative stress molecules such as nitric oxide and reactive oxygen species in lipopolysaccharide (LPS)-activated RAW 264.7 cells. Levels of inflammatory targets including prostaglandin E2, tumor necrosis factor-α, interleukin (IL)-1β and IL-6 were also reduced ...

 

Palladium-Catalyzed Multicomponent Synthesis of 2-Imidazolines from Imines and Acid Chlorides

  [CiTO]
Molecules, Vol. 17, No. 12. (22 November 2012), pp. 13759-13768, doi:10.3390/molecules171213759

Abstract

We describe the palladium-catalyzed multicomponent synthesis of 2-imidazolines. This reaction proceeds via the coupling of imines, acid chlorides and carbon monoxide to form imidazolinium carboxylates, followed by a decarboxylation. Decarboxylation in CHCl3 is found to result in a mixture of imidazolinium and imidazolium salts. However, the addition of benzoic acid suppresses aromatization, and generates the trans-disubstituted imidazolines in good yield. Combining this reaction with subsequent nitrogen deprotection provides an overall synthesis of imidazolines from multiple available building blocks. ...


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