Molecules

406 KiB

Open AccessArticle

Physicochemical Characteristics and Immunomodulatory Activities of Three Polysaccharide-Protein Complexes of Longan Pulp

by Yang Yi, Sen Tai Liao, Ming Wei Zhang, John Shi, Rui Fen Zhang, Yuan Yuan Deng and Zhen Cheng Wei

Molecules 2011, 16(7), 6148-6164; https://doi.org/10.3390/molecules16076148 - 21 Jul 2011

Cited by 64 | Viewed by 8657

Abstract

Three polysaccharide-protein complexes of longan pulp (LP1-3) were isolated in this work. Their physicochemical characteristics and immunomodulatory effects on splenocytes, natural killer (NK) cells and macrophages in vitro were investigated. The carbohydrate portions of LP1-3 were principally composed of glucose, arabinose and mannose. [...] Read more.

Three polysaccharide-protein complexes of longan pulp (LP1-3) were isolated in this work. Their physicochemical characteristics and immunomodulatory effects on splenocytes, natural killer (NK) cells and macrophages in vitro were investigated. The carbohydrate portions of LP1-3 were principally composed of glucose, arabinose and mannose. LP3 displayed the maximal moisture absorption, and the thermal stability of LP2 was obviously higher than that of LP1 and LP3. All of them showed the characteristic polysaccharide and protein bands in the Fourier Transform Infrared (FTIR) spectrum. For a certain dose, all the fractions could significantly stimulate splenocyte proliferation, macrophage phagocytosis against neutral red, and NK cell cytotoxicity against YAC-1 lymphoma cell (P < 0.05). The results demonstrated that the polysaccharide-protein complexes of longan pulp have medical potential as immunotherapeutic adjuvants due to their immunomodulatory activities. Full article

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870 KiB

Open AccessArticle

Synthesis and E/Z Configuration Determination of Novel Derivatives of 3-Aryl-2-(benzothiazol-2'-ylthio) Acrylonitrile, 3-(Benzothiazol-2'-ylthio)-4-(furan-2''-yl)-3-buten-2-one and 2-(1-(Furan-2''-yl)-3'-oxobut-1''-en-2-ylthio)-3-phenylquinazolin-4(3H)-one

by Fatima Al-Omran, Rafat M. Mohareb and Adel Abou El-Khair

Molecules 2011, 16(7), 6129-6147; https://doi.org/10.3390/molecules16076129 - 20 Jul 2011

Cited by 9 | Viewed by 8390

Abstract

Knoevenagel condensation of 2-(benzothiazol-2-ylthio) acetonitrile (2) with either furan-2-carbaldehyde or thiophene-2-carbaldehydes leads to E-isomers 4a–b exclusively, while the condensation of the compound 2 with benzaldehyde or para-substituted benzaldehydes with an electron-donating group afforded E/Z mixtures 4c–e with preferentially formation [...] Read more.

Knoevenagel condensation of 2-(benzothiazol-2-ylthio) acetonitrile (2) with either furan-2-carbaldehyde or thiophene-2-carbaldehydes leads to E-isomers 4a–b exclusively, while the condensation of the compound 2 with benzaldehyde or para-substituted benzaldehydes with an electron-donating group afforded E/Z mixtures 4c–e with preferentially formation of the E-isomer. Condensation of furan-2-carbaldehyde (3a) with either 1-(benzothiazol-2'-ylthio) propan-2-one (5) or 2-(2'-oxo propylthio)-3-phenyl-quinazolin-4(3H)-one (9) leads exclusively to the Z-isomers of 6 and 10, respectively. The structures of the newly synthesized compounds were elucidated by elemental analyses, ¹H-NMR and ¹³C-NMR spectra, COSY, HSQC, HMBC, NOE, MS and X-ray crystallographic investigations. Full article

(This article belongs to the Special Issue Heterocycles)

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481 KiB

Open AccessArticle

Ruthenium-Catalyzed Selective Hydrogenation of bis-Arylidene Tetramic Acids. Application to the Synthesis of Novel Structurally Diverse Pyrrolidine-2,4-diones

by Christos S. Karaiskos, Dimitris Matiadis, John Markopoulos and Olga Igglessi-Markopoulou

Molecules 2011, 16(7), 6116-6128; https://doi.org/10.3390/molecules16076116 - 20 Jul 2011

Cited by 3 | Viewed by 5760

Abstract

Catalytic hydrogenation of 3,5-bis-arylidenetetramic acids, known for their biological activity, has been developed. The chemoselective ruthenium-catalyzed reduction of the exocyclic carbon-carbon double bonds on pyrrolidine-2,4-dione ring system, containing other reducible functions, has been investigated. Depending on the substrate the yield of the hydrogenation [...] Read more.

Catalytic hydrogenation of 3,5-bis-arylidenetetramic acids, known for their biological activity, has been developed. The chemoselective ruthenium-catalyzed reduction of the exocyclic carbon-carbon double bonds on pyrrolidine-2,4-dione ring system, containing other reducible functions, has been investigated. Depending on the substrate the yield of the hydrogenation process can reach up to 95%. The structural elucidation has been established using NMR and HRMS spectral data. Full article

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1154 KiB

Open AccessReview

The Stereochemistry of Complex Polyketide Biosynthesis by Modular Polyketide Synthases

by David H. Kwan and Frank Schulz

Molecules 2011, 16(7), 6092-6115; https://doi.org/10.3390/molecules16076092 - 20 Jul 2011

Cited by 62 | Viewed by 14313

Abstract

Polyketides are a diverse class of medically important natural products whose biosynthesis is catalysed by polyketide synthases (PKSs), in a fashion highly analogous to fatty acid biosynthesis. In modular PKSs, the polyketide chain is assembled by the successive condensation of activated carboxylic acid-derived [...] Read more.

Polyketides are a diverse class of medically important natural products whose biosynthesis is catalysed by polyketide synthases (PKSs), in a fashion highly analogous to fatty acid biosynthesis. In modular PKSs, the polyketide chain is assembled by the successive condensation of activated carboxylic acid-derived units, where chain extension occurs with the intermediates remaining covalently bound to the enzyme, with the growing polyketide tethered to an acyl carrier domain (ACP). Carboxylated acyl-CoA precursors serve as activated donors that are selected by the acyltransferase domain (AT) providing extender units that are added to the growing chain by condensation catalysed by the ketosynthase domain (KS). The action of ketoreductase (KR), dehydratase (DH), and enoylreductase (ER) activities can result in unreduced, partially reduced, or fully reduced centres within the polyketide chain depending on which of these enzymes are present and active. The PKS-catalysed assembly process generates stereochemical diversity, because carbon–carbon double bonds may have either cis- or trans- geometry, and because of the chirality of centres bearing hydroxyl groups (where they are retained) and branching methyl groups (the latter arising from use of propionate extender units). This review shall cover the studies that have determined the stereochemistry in many of the reactions involved in polyketide biosynthesis by modular PKSs. Full article

(This article belongs to the Special Issue Polyketide)

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469 KiB

Open AccessArticle

Bent Dinuclear Platinum(II) Halo-Bridged Carbonyl Complexes

by Daniela Belli Dell'Amico, Luca Labella and Fabio Marchetti

Molecules 2011, 16(7), 6082-6091; https://doi.org/10.3390/molecules16076082 - 20 Jul 2011

Cited by 1 | Viewed by 5783

Abstract

Crystals of trans-Pt₂(μ-X)₂X₂(CO)₂ (X = Br, I) have been grown and their molecular and crystalline structures have been solved by X-ray diffraction methods. In both cases the dinuclear molecules are bent, with a [...] Read more.

Crystals of trans-Pt₂(μ-X)₂X₂(CO)₂ (X = Br, I) have been grown and their molecular and crystalline structures have been solved by X-ray diffraction methods. In both cases the dinuclear molecules are bent, with a bending angle of 164.6° and 156.5° for the bromide and the iodide, respectively. While the structure of the bromo-derivative is reported here for the first time, a modification of trans-Pt₂(μ-I)₂I₂(CO)₂ with planar centrosymmetric molecules is known. This appears to be a rare case of a platinum(II) halo-bridged derivative structurally characterized in both bent and planar forms. Full article

(This article belongs to the Special Issue Organometallic Chemistry)

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416 KiB

Open AccessArticle

Increased Carbon Dioxide Concentration Improves the Antioxidative Properties of the Malaysian Herb Kacip Fatimah (Labisia pumila Blume)

by Mohd Hafiz Ibrahim and Hawa Z.E. Jaafar

Molecules 2011, 16(7), 6068-6081; https://doi.org/10.3390/molecules16076068 - 20 Jul 2011

Cited by 34 | Viewed by 6287

Abstract

A randomized complete randomized design (RCBD) 3 by 3 experiment was designed to investigate and distinguish the relationships among production of secondary metabolites (total phenolics, TP; total flavonoids, TF), gluthatione (GSH), oxidized gluthatione (GSSG), soluble carbohydrate and antioxidant activities of the Malaysian medicinal [...] Read more.

A randomized complete randomized design (RCBD) 3 by 3 experiment was designed to investigate and distinguish the relationships among production of secondary metabolites (total phenolics, TP; total flavonoids, TF), gluthatione (GSH), oxidized gluthatione (GSSG), soluble carbohydrate and antioxidant activities of the Malaysian medicinal herb Labisia pumila Blume under three levels of CO₂ enrichment (400, 800 and 1,200 µmol mol⁻¹) for 15 weeks. It was found that the treatment effects were solely contributed by interaction of CO₂ levels and secondary metabolites distribution in plant parts, GSH, GSHH and antioxidant activities (peroxyl radicals (ROO), superoxide radicals (O₂), hydrogen peroxide (H₂O₂) and hydroxyl radicals (OH). The records of secondary metabolites, glutahione, oxidized gluthathione and antioxidant activities in a descending manner came from the leaf enriched with 1,200 µmol/mol CO₂ > leaf 800 µmol/mol CO₂ > leaf 400 µmol/mol CO₂ > stem 1,200 µmol/mol CO₂ > stem 800 µmol/mol CO₂ > stem 400 µmol/mol CO₂ > root 1,200 µmol/mol CO₂ > root 800 µmol/mol CO₂ > root 400 µmol/mol CO₂. Correlation analyses revealed strong significant positive coefficients of antioxidant activities with total phenolics, flavonoids, GSH and GSHH indicating that an increase in antioxidative activity of L. pumila under elevated CO₂ might be up-regulated by the increase in production of total phenolics, total flavonoids, GSH, GSHH and soluble sugar. This study implied that the medicinal potential of herbal plant such as L. pumila can be enhanced under elevated CO₂, which had simultaneously improved the antioxidative activity that indicated by the high oxygen radical absorbance activity against ROO, O₂, H₂O₂, and OH radicals. Full article

392 KiB

Open AccessArticle

Antifeedant Diterpenoids against Tribolium castaneum from the Stems and Twigs of Ceriops tagal (Rhizophoraceae)

by Shu Shan Du, Cheng Fang Wang, Jing Li, Hai Ming Zhang, Qi Zhi Liu, Zhi Long Liu and Zhi Wei Deng

Molecules 2011, 16(7), 6060-6067; https://doi.org/10.3390/molecules16076060 - 20 Jul 2011

Cited by 23 | Viewed by 7072

Abstract

The screening of several Chinese mangrove plants for insecticidal principles showed that ethanol extract of Ceriops tagal stems and twigs possessed significant feeding deterrent activity against the red flour beetle, Tribolium castaneum (Family: Rhizophoraceae). From the ethanol extract, three feeding deterrent diterpenoids were [...] Read more.

The screening of several Chinese mangrove plants for insecticidal principles showed that ethanol extract of Ceriops tagal stems and twigs possessed significant feeding deterrent activity against the red flour beetle, Tribolium castaneum (Family: Rhizophoraceae). From the ethanol extract, three feeding deterrent diterpenoids were isolated by bioassay-guided fractionation. The compounds were identified as tagalsin A, B, and H on the basis of their phytochemical and spectral data. Tagalsin A, B, and H exhibited strong feeding deterrent activity against T. castaneum adults with EC₅₀ values of 375.3 ppm, 277.3 ppm, and 285.45 ppm, respectively. Full article

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1722 KiB

Open AccessReview

Enzyme-Immobilized Microfluidic Process Reactors

by Yuya Asanomi, Hiroshi Yamaguchi, Masaya Miyazaki and Hideaki Maeda

Molecules 2011, 16(7), 6041-6059; https://doi.org/10.3390/molecules16076041 - 19 Jul 2011

Cited by 140 | Viewed by 12692

Abstract

Microreaction technology, which is an interdisciplinary science and engineering area, has been the focus of different fields of research in the past few years. Several microreactors have been developed. Enzymes are a type of catalyst, which are useful in the production of substance [...] Read more.

Microreaction technology, which is an interdisciplinary science and engineering area, has been the focus of different fields of research in the past few years. Several microreactors have been developed. Enzymes are a type of catalyst, which are useful in the production of substance in an environmentally friendly way, and they also have high potential for analytical applications. However, not many enzymatic processes have been commercialized, because of problems in stability of the enzymes, cost, and efficiency of the reactions. Thus, there have been demands for innovation in process engineering, particularly for enzymatic reactions, and microreaction devices represent important tools for the development of enzyme processes. In this review, we summarize the recent advances of microchannel reaction technologies especially for enzyme immobilized microreactors. We discuss the manufacturing process of microreaction devices and the advantages of microreactors compared to conventional reaction devices. Fundamental techniques for enzyme immobilized microreactors and important applications of this multidisciplinary technology are also included in our topics. Full article

(This article belongs to the Special Issue Enzyme-Catalyzed Reactions)

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1284 KiB

Open AccessArticle

Benzylidene-bis-(4-Hydroxycoumarin) and Benzopyrano-Coumarin Derivatives: Synthesis, ¹H/¹³C-NMR Conformational and X-ray Crystal Structure Studies and In Vitro Antiviral Activity Evaluations

by Davorka Završnik, Samija Muratović, Damjan Makuc, Janez Plavec, Mario Cetina, Ante Nagl, Erik De Clercq, Jan Balzarini and Mladen Mintas

Molecules 2011, 16(7), 6023-6040; https://doi.org/10.3390/molecules16076023 - 19 Jul 2011

Cited by 92 | Viewed by 12641

Abstract

We report on the synthesis of 4-hydroxycoumarin dimers 1–15 bearing an aryl substituent on the central linker and fused benzopyranocoumarin derivatives 16–20 and on their in vitro broad anti-DNA and RNA virus activity evaluations. The chemical identities and structure [...] Read more.

We report on the synthesis of 4-hydroxycoumarin dimers 1–15 bearing an aryl substituent on the central linker and fused benzopyranocoumarin derivatives 16–20 and on their in vitro broad anti-DNA and RNA virus activity evaluations. The chemical identities and structure of compounds 1–20 were deduced from their homo- and heteronuclear NMR measurements whereas the conformational properties of 5, 14 and 20 were assessed by the use of 1D difference NOE enhancements. Unequivocal proof of the stereostructure of compounds 7, 9, 16 and 18 was obtained by single crystal X-ray diffraction method. The X-ray crystal structure analysis revealed that two 4-hydroxycoumarin moieties in the 4-trifluoromethylphenyl- and 2-nitrophenyl derivatives (compounds 7 and 9, respectively) are intramolecularly hydrogen-bonded between hydroxyl and carbonyl oxygen atoms. Consequently, the compounds 7 and 9 adopt conformations in which two 4-hydroxy-coumarin moieties are anti-disposed. Antiviral activity evaluation results indicated that the 4-bromobenzylidene derivative of bis-(4-hydroxycoumarin) (compound 3) possesses inhibitory activity against HSV-1 (KOS), HSV-2 (G), vaccinia virus and HSV-1 TK^- KOS (ACV^r) at a concentration of 9–12 μM and at a minimum cytotoxic concentration (MCC) greater than 20 μM. Compounds 4–6, 8, and 20 were active against feline herpes virus (50% effective concentration, EC₅₀ = 5–8.1 μM), that is at a 4-7-fold lower concentration than the MCC. Full article

(This article belongs to the Special Issue Antivirals)

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881 KiB

Open AccessArticle

Inhibitory Effects of Constituents from Morus alba var. multicaulis on Differentiation of 3T3-L1 Cells and Nitric Oxide Production in RAW264.7 Cells

by Zhi-Gang Yang, Keiichi Matsuzaki, Satoshi Takamatsu and Susumu Kitanaka

Molecules 2011, 16(7), 6010-6022; https://doi.org/10.3390/molecules16076010 - 19 Jul 2011

Cited by 92 | Viewed by 11867

Abstract

A new arylbenzofuran, 3',5'-dihydroxy-6-methoxy-7-prenyl-2-arylbenzofuran (1), and 25 known compounds, including moracin R (2), moracin C (3), moracin O (4), moracin P (5), artoindonesianin O (6), moracin D (7), alabafuran [...] Read more.

A new arylbenzofuran, 3',5'-dihydroxy-6-methoxy-7-prenyl-2-arylbenzofuran (1), and 25 known compounds, including moracin R (2), moracin C (3), moracin O (4), moracin P (5), artoindonesianin O (6), moracin D (7), alabafuran A (8), mulberrofuran L (9), mulberrofuran Y (10), kuwanon A (11), kuwanon C (12), kuwanon T (13), morusin (14), kuwanon E (15), sanggenon F (16), betulinic acid (17), uvaol (18), ursolic acid (19), β-sitosterol (20), oxyresveratrol 2-O-β-D-glucopyranoside (21), mulberroside A (22), mulberroside B (23), 5,7-dihydroxycoumarin 7-O-β-D-glucopyranoside (24), 5,7-dihydroxycoumarin 7-O-β-D-apiofuranosyl-(1→6)-O-β-D-glucopyranoside (25) and adenosine (26), were isolated from Morus alba var. multicaulis Perro. (Moraceae). Their structures were determined by spectroscopic methods. The prenyl-flavonoids 11–14, 16, triterpenoids 17,18 and 20 showed significant inhibitory activity towards the differentiation of 3T3-L1 adipocytes. The arylbenzofurans 1–10 and prenyl-flavonoids 11–16 also showed significant nitric oxide (NO) production inhibitory effects in RAW264.7 cells. Full article

(This article belongs to the Section Natural Products Chemistry)

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488 KiB

Open AccessArticle

Antioxidant Activities of Extracts and Fractions from Eupatorium lindleyanum DC

by Guilong Yan, Lilian Ji, Yuming Luo and Yonghong Hu

Molecules 2011, 16(7), 5998-6009; https://doi.org/10.3390/molecules16075998 - 19 Jul 2011

Cited by 20 | Viewed by 6465

Abstract

The antioxidant activities of water extract (WE), ethanol extract (EE), residue water extract (RWE) and petroleum ether (PF), ethyl acetate (EF), n-BuOH (BF) and water (WF) fractions of the ethanol extract from Eupatorium Lindley DC were investigated for the first time. Total [...] Read more.

The antioxidant activities of water extract (WE), ethanol extract (EE), residue water extract (RWE) and petroleum ether (PF), ethyl acetate (EF), n-BuOH (BF) and water (WF) fractions of the ethanol extract from Eupatorium Lindley DC were investigated for the first time. Total phenolics content, DPPH radical scavenging activities, superoxide radical scavenging activities, total reduction capability, and ferrous ions chelating activities were determined for all the extracts and fractions. The results showed that all the extracts and fractions exhibited antioxidant activities with different magnitudes of potency. Among all the samples, WE and RWE exhibited the best antioxidant capacities, the BF also exhibited high antioxidant abilities in all tests except for the metal chelating activity, while the other extracts and fractions were relatively weak antioxidants. The BF had the highest total phenolics contents in all extracts and fractions, and the WE and RWE were found to be rich in tannins. Furthermore, the content of total phenolics showed good correlation with DPPH radical scavenging activity, superoxide anion radical scavenging activity, and the reducing power. Phenolic composition of all the extracts and fractions was identified and quantified by HPLC. The results indicate that the extracts of E. Lindley DC might be a useful potential source of natural antioxidant ingredients. Full article

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460 KiB

Open AccessArticle

Three New Phytoecdysteroids Containing a Furan Ring from the Roots of Achyranthes bidentata Bl.

by Qiu-Hong Wang, Liu Yang, Hai Jiang, Zhi-Bin Wang, Bing-You Yang and Hai-Xue Kuang

Molecules 2011, 16(7), 5989-5997; https://doi.org/10.3390/molecules16075989 - 18 Jul 2011

Cited by 22 | Viewed by 8692

Abstract

Three new phytoecdysteroid compounds, named niuxixinsterone A (1), B (2) and C (3) with acetal functions in the side-chain were isolated from Achyranthes bidentata Bl. The structures were established as (20R,22R,24S)-20- [...] Read more.

Three new phytoecdysteroid compounds, named niuxixinsterone A (1), B (2) and C (3) with acetal functions in the side-chain were isolated from Achyranthes bidentata Bl. The structures were established as (20R,22R,24S)-20-O,22-O-(5′-hydroxymethyl)-furfurylidene-2β,3β,14α,25-tetrahydroxy-5β-ergost-7-en-6-one (1), (20R,22R)-20-O,22-O-(5′-hydroxymethyl)-furfurylidene-2β,3β,25-trihydroxy-14β-methyl-18-nor-5β-cholesta-7,12-dien-6-one (2) and (20R,22R,25R)-20-O,22-O-(5′-hydroxymethyl)-furfurylidene-2β, 3β,5β,14α,26-pentahydroxycholest-7-en-6-one (3) by means of spectroscopic evidence. Full article

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Graphical abstract

549 KiB

Open AccessArticle

Integrated One-Pot Enrichment and Immobilization of Styrene Monooxygenase (StyA) Using SEPABEAD EC-EA and EC-Q1A Anion-Exchange Carriers

by Reto Ruinatscha, Rohan Karande, Katja Buehler and Andreas Schmid

Molecules 2011, 16(7), 5975-5988; https://doi.org/10.3390/molecules16075975 - 18 Jul 2011

Cited by 6 | Viewed by 7009

Abstract

A straightforward one-pot procedure combining enrichment and immobilization of recombinantely expressed FADH₂ dependent styrene monooxygenase (StyA) directly from Escherichia coli cell extracts was investigated. Sepabeads EC-EA and EC-Q1A anion-exchange carriers were employed to non-covalently adsorb StyA from the cell extracts depending on [...] Read more.

A straightforward one-pot procedure combining enrichment and immobilization of recombinantely expressed FADH₂ dependent styrene monooxygenase (StyA) directly from Escherichia coli cell extracts was investigated. Sepabeads EC-EA and EC-Q1A anion-exchange carriers were employed to non-covalently adsorb StyA from the cell extracts depending on basic parameters such as varying initial protein concentrations and pH. The protein fraction of the cell extract contained around 25% StyA. At low initial protein concentrations (2.5 mg mL⁻¹) and pH 6, the enzyme could be enriched up to 52.4% on Sepabeads EC-EA and up to 46.0% on Sepabeads EC-Q1A, accounting for an almost complete StyA adsorption from the cell extracts. Higher initial protein concentrations were necessary to exploit the high loading capacity of the beads. At 20 mg mL⁻¹, up to 37.6% of the theoretical bead loading capacity could be utilized for StyA binding using Sepabeads EC-EA, and 34.0% using Sepabeads EC-Q1A. For both carriers, protein leakage under reaction conditions could be reduced to less than 2%. During assays, the FADH₂ cofactor necessary for StyA activity was supplied by the NADH-FAD reductase component styrene monooxygenase B (StyB). StyA immobilized on Sepabeads EC-Q1A displayed twice as high styrene epoxidation rates (0.2 U mg_StyA⁻¹) as compared to Sepabeads EC-EA. This activity could be increased to 0.7 U mg_StyA⁻¹ by co-immobilizing StyB on Sepabeads EC-Q1A, which corresponds to 33% of the soluble StyA activity. Full article

(This article belongs to the Special Issue Enzyme-Catalyzed Reactions)

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440 KiB

Open AccessArticle

Synthetic Organic Electrochemistry in Ionic Liquids: The Viscosity Question

by Steven Bornemann and Scott T. Handy

Molecules 2011, 16(7), 5963-5974; https://doi.org/10.3390/molecules16075963 - 18 Jul 2011

Cited by 16 | Viewed by 7468

Abstract

Ionic liquids are obvious candidates for use in electrochemical applications due to their ionic character. Nevertheless, relatively little has been done to explore their application in electrosynthesis. We have studied the Shono oxidation of arylamines and carbamates using ionic liquids as recyclable solvents [...] Read more.

Ionic liquids are obvious candidates for use in electrochemical applications due to their ionic character. Nevertheless, relatively little has been done to explore their application in electrosynthesis. We have studied the Shono oxidation of arylamines and carbamates using ionic liquids as recyclable solvents and have noted that the viscosity of the medium is a major problem, although with the addition of sufficient co-solvent, good results and excellent recovery and recycling of the ionic liquid can be achieved. Full article

(This article belongs to the Special Issue Organic Electrosynthesis)

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756 KiB

Open AccessReview

In Mesopore Protein Digestion: A New Forthcoming Strategy in Proteomics

by Rocco Savino, Francesca Casadonte and Rosa Terracciano

Molecules 2011, 16(7), 5938-5962; https://doi.org/10.3390/molecules16075938 - 15 Jul 2011

Cited by 24 | Viewed by 7078

Abstract

The conventional protocols for in solution or in gel protein digestion require many steps and long reaction times. The use of trypsin immobilized onto solid supports has recently captured the attention of many research groups, because these systems can speed-up protein digestion significantly. [...] Read more.

The conventional protocols for in solution or in gel protein digestion require many steps and long reaction times. The use of trypsin immobilized onto solid supports has recently captured the attention of many research groups, because these systems can speed-up protein digestion significantly. The utilization of new materials such as mesoporous silica as supports, in which enzyme and substrate are dramatically concentrated and confined in the nanospace, offers new opportunities to reduce the complexity of proteomics workflows. An overview of the procedures for in situ proteolysis of single proteins or complex protein mixtures is reported, with a special focus on porous materials used as catalysts. The challenging efforts for designing such systems aimed at mimicking the biochemistry of living cells are reviewed. Potentials, limitations and challenges of this branch of enzyme catalysis, which we indicate as in mesopore digestion, are discussed, in relation to its suitability for high-speed and high-throughput proteomics. Full article

(This article belongs to the Special Issue Catalytic Asymmetric Synthesis)

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492 KiB

Open AccessArticle

The Use of Response Surface Methodology to Optimize the Ultrasound-Assisted Extraction of Five Anthraquinones from Rheum palmatum L.

by Li-Chun Zhao, Jian Liang, Wei Li, Kun-Mu Cheng, Xianghua Xia, Xin Deng and Geng-Liang Yang

Molecules 2011, 16(7), 5928-5937; https://doi.org/10.3390/molecules16075928 - 15 Jul 2011

Cited by 51 | Viewed by 12973

Abstract

In this paper, ultrasound-assisted extraction (UAE) was applied to the extraction of anthraquinones (aloe-emodin, rhein, emodin, chrysophanol and physcion) from Rheum palmatum L. The five anthraquinones were quantified and analyzed by high performance liquid chromatography coupled with UV detection (HPLC-UV). The extraction solvent, [...] Read more.

In this paper, ultrasound-assisted extraction (UAE) was applied to the extraction of anthraquinones (aloe-emodin, rhein, emodin, chrysophanol and physcion) from Rheum palmatum L. The five anthraquinones were quantified and analyzed by high performance liquid chromatography coupled with UV detection (HPLC-UV). The extraction solvent, extraction temperature and extraction time parameters, the three main factors for UAE, were optimized with response surface methodology (RSM) to obtain the highest extraction efficiency. The optimal conditions were the use of 84% methanol as solvent, an extraction time of 33 min and an extraction temperature of 67 °C. Under these optimal conditions, the experimental values agreed closely with the predicted values. The analysis of variance indicated a high goodness of model fit and the success of RSM method for optimizing anthraquinones extraction in Rheum palmatum L. Full article

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605 KiB

Open AccessArticle

Industrial Aplication of Catalytic Systems for n-Heptane Isomerization

by Laura Olivia Alemán-Vázquez, José Luis Cano-Domínguez, Enelio Torres-García and José Roberto Villagómez-Ibarra

Molecules 2011, 16(7), 5916-5927; https://doi.org/10.3390/molecules16075916 - 14 Jul 2011

Cited by 23 | Viewed by 9536

Abstract

The ideal gasoline must have a high pump octane number, in the 86 to 94 range, and a low environmental impact. Alkanes, as a family, have much lower photochemical reactivities than aromatics or olefins, but only the highly branched alkanes have adequate octane [...] Read more.

The ideal gasoline must have a high pump octane number, in the 86 to 94 range, and a low environmental impact. Alkanes, as a family, have much lower photochemical reactivities than aromatics or olefins, but only the highly branched alkanes have adequate octane numbers. The purpose of this work is to examine the possibilities of extending the technological alternative of paraffin isomerization to heavier feedstocks (i.e., n-heptane) using non-conventional catalytic systems which have been previously proposed in the literature: a Pt/sulfated zirconia catalyst and a molybdenum sub-oxide catalyst. Under the experimental conditions at which these catalysts have been evaluated, the molybdenum sub-oxide catalyst maintains a good activity and selectivity to isomerization after 24 h, while the Pt/sulfated zirconia catalyst shows a higher dimethylpentanes/methylhexanes ratio, probably due to a lower operating temperature, but also a high formation of cracking products, and presents signs of deactivation after 8 h. Though much remains to be done, the performance of these catalysts indicates that there are good perspectives for their industrial application in the isomerization of n-heptane and heavier alkanes. Full article

(This article belongs to the Section Molecular Diversity)

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Open AccessArticle

HPLC Separation of All Aldopentoses and Aldohexoses on an Anion-Exchange Stationary Phase Prepared from Polystyrene-Based Copolymer and Diamine: The Effect of NaOH Eluent Concentration

by Kadumi Inoue, Kei-ichi Kitahara, Yoshihiro Aikawa, Sadao Arai and Takako Masuda-Hanada

Molecules 2011, 16(7), 5905-5915; https://doi.org/10.3390/molecules16075905 - 14 Jul 2011

Cited by 17 | Viewed by 7485

Abstract

To investigate the separations of all aldopentoses (ribose, arabinose, xylose and lyxose) and aldohexoses (glucose, galactose, allose, altrose, mannose, gulose, idose and talose) on the D₆ stationary phase prepared by the reaction of chloromethylated styrene-divinylbenzene copolymer and N,N,N [...] Read more.

To investigate the separations of all aldopentoses (ribose, arabinose, xylose and lyxose) and aldohexoses (glucose, galactose, allose, altrose, mannose, gulose, idose and talose) on the D₆ stationary phase prepared by the reaction of chloromethylated styrene-divinylbenzene copolymer and N,N,N’,N’-tetramethyl-1,6-diaminohexane, we examined the effect of varying the concentration of the NaOH eluent on the elution orders. Separations of these aldoses were achieved using a 20 mM NaOH eluent. The elution behaviors of the aldoses were probably due to not only the individual pK_a values, but also the chemical structures of the cyclic aldoses. Full article

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Open AccessArticle

Biocatalytic Resolution of Enantiomeric Mixtures of 1-Aminoethanephosphonic Acid

by Małgorzata Brzezińska-Rodak, Magdalena Klimek-Ochab, Ewa Żymańczyk-Duda and Paweł Kafarski

Molecules 2011, 16(7), 5896-5904; https://doi.org/10.3390/molecules16075896 - 14 Jul 2011

Cited by 21 | Viewed by 6552

Abstract

Several fungal strains, namely Bauveria bassiana, Cuninghamella echinulata, Aspergillus fumigatus, Penicillium crustosum and Cladosporium herbarum, were used as biocatalysts to resolve racemic mixtures of 1-aminoethanephosphonic acid using L/D amino acid oxidase activity. The course of reaction was analyzed by ³¹P-NMR in [...] Read more.

Several fungal strains, namely Bauveria bassiana, Cuninghamella echinulata, Aspergillus fumigatus, Penicillium crustosum and Cladosporium herbarum, were used as biocatalysts to resolve racemic mixtures of 1-aminoethanephosphonic acid using L/D amino acid oxidase activity. The course of reaction was analyzed by ³¹P-NMR in the presence of cyclodextrin used as chiral discriminating agent. The best result (42% e.e of R-isomer) was obtained with a strain of Cuninghamella echinulata. Full article

(This article belongs to the Special Issue Enzyme-Catalyzed Reactions)

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Open AccessArticle

Friedel-Craft Acylation of ar-Himachalene: Synthesis of Acyl-ar-Himachalene and a New Acyl-Hydroperoxide

by Issam Hossini, Mohamed Anoir Harrad, Mustapha Ait Ali, Larbi El Firdoussi, Abdallah Karim, Pedro Valerga and M. Carmen Puerta

Molecules 2011, 16(7), 5886-5895; https://doi.org/10.3390/molecules16075886 - 14 Jul 2011

Cited by 9 | Viewed by 10645

Abstract

Friedel-Craft acylation at 100 °C of 2,5,9,9-tetramethyl-6,7,8,9-tetrahydro-5H-benzocycloheptene [ar-himachalene (1)], a sesquiterpenic hydrocarbon obtained by catalytic dehydrogenation of α-, β- and γ-himachalenes, produces a mixture of two compounds: (3,5,5,9-tetramethyl-6,7,8,9-tetrahydro-5H-benzocyclohepten-2-yl)-ethanone (2, in 69% yield), with a conserved [...] Read more.

Friedel-Craft acylation at 100 °C of 2,5,9,9-tetramethyl-6,7,8,9-tetrahydro-5H-benzocycloheptene [ar-himachalene (1)], a sesquiterpenic hydrocarbon obtained by catalytic dehydrogenation of α-, β- and γ-himachalenes, produces a mixture of two compounds: (3,5,5,9-tetramethyl-6,7,8,9-tetrahydro-5H-benzocyclohepten-2-yl)-ethanone (2, in 69% yield), with a conserved reactant backbone, and 3, with a different skeleton, in 21% yield. The crystal structure of 3 reveals it to be 1-(8-ethyl-8-hydroperoxy-3,5,5-trimethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-ethanone. In this compound O-H…O bonds form dimers. These hydrogen-bonds, in conjunction with weaker C-H…O interactions, form a more extended supramolecular arrangement in the crystal. Full article

(This article belongs to the Section Organic Chemistry)

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Open AccessArticle

Comparative Properties of Amazonian Oils Obtained by Different Extraction Methods

by Bianca Silva Ferreira, Camila Guimarães De Almeida, Lara Pereira Faza, Angelina De Almeida, Cláudio Galuppo Diniz, Vânia Lúcia da Silva, Richard Michael Grazul and Mireille Le Hyaric

Molecules 2011, 16(7), 5875-5885; https://doi.org/10.3390/molecules16075875 - 13 Jul 2011

Cited by 83 | Viewed by 12488

Abstract

Pequi (Caryocar brasiliense Camb.), babaçu (Orbignya phalerata Mart.), buriti (Mauritia flexuosa), and passion fruit (Passiflora edulis) oils were studied to determine their antibacterial, antioxidant and cytotoxic activities, as well as their total phenol and carotenoid [...] Read more.

Pequi (Caryocar brasiliense Camb.), babaçu (Orbignya phalerata Mart.), buriti (Mauritia flexuosa), and passion fruit (Passiflora edulis) oils were studied to determine their antibacterial, antioxidant and cytotoxic activities, as well as their total phenol and carotenoid contents. The fatty acid contents were determined by GC-MS. The three types of passion fruit oils studied were refined, cold pressed or extracted from seeds in a Soxhlet apparatus. The oils thus obtained showed differences in antioxidant activity and carotenoid content, but were similar in regard to total phenols. Buriti and pequi had the highest carotenoid contents, while refined and cold pressed passion fruit oil displayed the highest antioxidant activity. Pequi oil was the only oil to display antibacterial and cytotoxic activity. Full article

(This article belongs to the Section Natural Products Chemistry)

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Open AccessArticle

Synthesis and Biological Activities on Metal Complexes of 2,5-Diamino-1,3,4-thiadiazole Derived from Semicarbazide Hydrochloride

by Joshua A. Obaleye, Johnson F. Adediji and Matthew A. Adebayo

Molecules 2011, 16(7), 5861-5874; https://doi.org/10.3390/molecules16075861 - 12 Jul 2011

Cited by 31 | Viewed by 7710

Abstract

A bioactive ligand, 2,5-diamino-1,3,4-thiadiazole (L), derived from semicarbazide hydrochloride, and its metal complexes were prepared and characterized. The complexes were characterized using elemental, infra-red, ultraviolet/visible, magnetic moment, atomic absorption, thin layer chromatography and molar conductance measurements. The IR data revealed that [...] Read more.

A bioactive ligand, 2,5-diamino-1,3,4-thiadiazole (L), derived from semicarbazide hydrochloride, and its metal complexes were prepared and characterized. The complexes were characterized using elemental, infra-red, ultraviolet/visible, magnetic moment, atomic absorption, thin layer chromatography and molar conductance measurements. The IR data revealed that the ligand (L) behaved as a tridentate neutral ligand. It coordinated to the metal ion via sulphur and nitrogen of the amines. The molar conductance data reveal that the chelates are non-electrolytes. From the Ultraviolet/Visible spectra and magnetic moment data, the complexes were found to have octahedral geometrical structure. In vivo evaluation of the antimicrobial activities of the metal complexes and the ligands showed greater activity against some micro-organisms when compared to the parent compounds. The chelates do not show toxicity against the activities of enzymes from homogenates of liver, kidney and serum in experimental rats. Full article

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Open AccessArticle

Synthesis and Cytotoxic Activity of Some New 2,6-Substituted Purines

by Nageswara Rao Kode and Shashikant Phadtare

Molecules 2011, 16(7), 5840-5860; https://doi.org/10.3390/molecules16075840 - 11 Jul 2011

Cited by 12 | Viewed by 6318

Abstract

A seriesof twenty four acyclic unsaturated 2,6-substututed purines 5a-20b were synthesized. These compounds were evaluated for cytotoxic activity against NCI-60 DTP human tumor cell line screen at 10µMconcentration. N₉-[(Z)-4'-chloro-2'-butenyl-1'-yl]-2,6-dichloropurine(5a), N₉-[4'-chloro-2'-butynyl-1'-yl]-2,6-dichloropurine(10a), N₉-[( [...] Read more.

A seriesof twenty four acyclic unsaturated 2,6-substututed purines 5a-20b were synthesized. These compounds were evaluated for cytotoxic activity against NCI-60 DTP human tumor cell line screen at 10µMconcentration. N₉-[(Z)-4'-chloro-2'-butenyl-1'-yl]-2,6-dichloropurine(5a), N₉-[4'-chloro-2'-butynyl-1'-yl]-2,6-dichloropurine(10a), N₉-[(E)-2',3'-dibromo-4'-chloro-2'-butenyl-1'-yl]-6-methoxypurine(14)and N₉-[4'-chloro-2'-butynyl-1'-yl]-6-(4-methoxyphenyl)-purine(19)exhibited highly potent cytotoxic activity with GI₅₀ values in the 1–5 µM range for most human tumor cell lines. Other compounds exhibited moderate activity. Full article

(This article belongs to the Section Medicinal Chemistry)

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Open AccessArticle

Two New Withanolide Lactones from Flos Daturae

by Hai-Xue Kuang, Bing-You Yang, Yong-Gang Xia and Qiu-Hong Wang

Molecules 2011, 16(7), 5833-5839; https://doi.org/10.3390/molecules16075833 - 11 Jul 2011

Cited by 39 | Viewed by 6791

Abstract

Chemical investigation of the 50% ethanol eluate fraction from a macroporous resin of flowers of Datura metel L. collected in the Jiangsu Province of China resulted in the isolation of two new withanolides, baimantuoluoline G (1) and baimantuoluoside H (2 [...] Read more.

Chemical investigation of the 50% ethanol eluate fraction from a macroporous resin of flowers of Datura metel L. collected in the Jiangsu Province of China resulted in the isolation of two new withanolides, baimantuoluoline G (1) and baimantuoluoside H (2). Their structures were elucidated as (12β,6β,22R)-1,10-seco-6,12,27-trihydroxy-26-oxo-witha-3,5,24-trienolide-1-oic acid-ε-lactone (1) and (5β,6α,12β,22R)-5,6,12,27-tetra-hydroxy-1,26-dioxo-witha-2,24-dienolide-27-O-β-glucopyranoside (2) on the basis of extensive spectroscopic analysis (1D, 2D-NMR and HRESIMS) and chemical studies. Full article

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Open AccessArticle

Characterization and Determination of the Alkaloid Metabolites of Evodiae fructus in Rat Urine by Liquid Chromatography-Tandem Mass Spectrometry Detection

by Rui Yan, Qier Mu, Yin Wang, Youping Liu and Xin Di

Molecules 2011, 16(7), 5822-5832; https://doi.org/10.3390/molecules16075822 - 8 Jul 2011

Cited by 6 | Viewed by 6786

Abstract

The lack of authentic standards limits the quantitative analysis of herbal drugs in biological samples. This present work demonstrated a practicable assay of herbs and their metabolites independent of the availability of authentic standards. A liquid chromatography–electrospray ionization–mass spectrometry (LC–ESI–MS) method for the [...] Read more.

The lack of authentic standards limits the quantitative analysis of herbal drugs in biological samples. This present work demonstrated a practicable assay of herbs and their metabolites independent of the availability of authentic standards. A liquid chromatography–electrospray ionization–mass spectrometry (LC–ESI–MS) method for the qualitative and quantitative determination of the metabolites after oral administration of Evodiae fructus and Zuojinwan preparation in rat urine has been developed. Urine samples extracted with a protein precipitation procedure were separated on a C₁₈ column using a mixture of water (containing 0.1% formic acid) and acetonitrile (30:70, v/v) as mobile phase. The detection was performed by MS with electrospray ionization interface in positive selected reaction monitoring (SRM) mode. One urine sample after administration was selected as 'standard'. The method validation was carried out according to a conventional method that was calibrated by authentic standards. The fully validated method was applied to the pharmacokinetic study of the metabolites in rat urine. The results could provide evidence to explain the combination of Coptidis rhizoma and Evodiae fructus in terms of elimination. Full article

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Open AccessArticle

Synthesis and Spectroscopic Characterization of Two Tetrasubstituted Cationic Porphyrin Derivatives

by Antonio E.H. Machado, Weverson R. Gomes, Diesley M.S. Araújo, Hércules S. Miglio, Leonardo T. Ueno, Rodrigo De Paula, José A.S. Cavaleiro and Newton M. Barbosa Neto

Molecules 2011, 16(7), 5807-5821; https://doi.org/10.3390/molecules16075807 - 8 Jul 2011

Cited by 12 | Viewed by 8412

Abstract

An imidazolium tetrasubstituted cationic porphyrin derivative (the free base and its Zn(II) complex) with five-membered heterocyclic groups in the meso-positions were synthesized using microwave irradiation, and the compounds obtained characterized by ¹H-NMR and mass spectrometry. We observed that under microwave irradiation [...] Read more.

An imidazolium tetrasubstituted cationic porphyrin derivative (the free base and its Zn(II) complex) with five-membered heterocyclic groups in the meso-positions were synthesized using microwave irradiation, and the compounds obtained characterized by ¹H-NMR and mass spectrometry. We observed that under microwave irradiation the yield is similar to when the synthesis is performed under conventional heating, however, the time required to prepare the porphyrins decreases enormously. In order to investigate the electronic state of these compounds, we employed UV-Vis and fluorescence spectroscopy combined with quantum chemical calculations. The results reveal the presence, in both compounds, of a large number of electronic states involving the association between the Soret and a blue-shifted band. The Soret band in both compounds also shows a considerable solvent dependence. As for emission, these compounds present low quantum yield at room temperature and no solvent influence on the fluorescence spectra was observed. Full article

(This article belongs to the Special Issue Organometallic Chemistry)

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Design, Synthesis and Biological Activity Evaluation of Arylpiperazine Derivatives for the Treatment of Neuropathic Pain

by Yin Chen, Guan Wang, Xiangqing Xu, Bi-Feng Liu, Jianqi Li and Guisen Zhang

Molecules 2011, 16(7), 5785-5806; https://doi.org/10.3390/molecules16075785 - 7 Jul 2011

Cited by 9 | Viewed by 6054

Abstract

In this work, a series of arylpiperazine derivatives were synthesized and screened by in vivo pharmacological trials. Among the tested compounds, 2-(4-(3-(trifluoromethyl)phenyl)piperazin-1-yl)-1-phenylethanone (18) and 2-(4-(2,3-dimethylphenyl)piperazin-1-yl)-1-phenylethanone (19) exhibited potent analgesic activities in both the mice writhing and mice hot [...] Read more.

In this work, a series of arylpiperazine derivatives were synthesized and screened by in vivo pharmacological trials. Among the tested compounds, 2-(4-(3-(trifluoromethyl)phenyl)piperazin-1-yl)-1-phenylethanone (18) and 2-(4-(2,3-dimethylphenyl)piperazin-1-yl)-1-phenylethanone (19) exhibited potent analgesic activities in both the mice writhing and mice hot plate tests. They showed more than 70% inhibition relative to controls in the writhing test, and increased latency by 116.0% and 134.4%, respectively, in the hot plate test. Furthermore, compound 18 was also active in the models of formalin pain and neuropathic pain without sedative side effects. Full article

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Open AccessArticle

Use of Novel Cardanol-Porphyrin Hybrids and Their TiO₂-Based Composites for the Photodegradation of 4-Nitrophenol in Water

by Giuseppe Vasapollo, Giuseppe Mele, Roberta Del Sole, Iolanda Pio, Jun Li and Selma Elaine Mazzetto

Molecules 2011, 16(7), 5769-5784; https://doi.org/10.3390/molecules16075769 - 7 Jul 2011

Cited by 32 | Viewed by 7863

Abstract

Cardanol, a well known hazardous byproduct of the cashew industry, has been used as starting material for the synthesis of useful differently substituted “cardanol-based” porphyrins and their zinc(II), copper(II), cobalt(II) and Fe(III) complexes. Novel composites prepared by impregnation of polycrystalline TiO₂ powder [...] Read more.

Cardanol, a well known hazardous byproduct of the cashew industry, has been used as starting material for the synthesis of useful differently substituted “cardanol-based” porphyrins and their zinc(II), copper(II), cobalt(II) and Fe(III) complexes. Novel composites prepared by impregnation of polycrystalline TiO₂ powder with an opportune amount of “cardanol-based” porphyrins, which act as sensitizers for the improvement of the photo-catalytic activity of the bare TiO₂, have been used in the photodegradation in water of 4-nitrophenol (4-NP), which is a toxic and bio-refractory pollutant, dangerous for ecosystems and human health. Full article

(This article belongs to the Special Issue Tetrapyrroles, Porphyrins and Phthalocyanines)

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Pentamethylquercetin Improves Adiponectin Expression in Differentiated 3T3-L1 Cells via a Mechanism that Implicates PPARγ together with TNF-α and IL-6

by Lei Chen, Ting He, Yi Han, Ji-Zhong Sheng, Si Jin and Man-Wen Jin

Molecules 2011, 16(7), 5754-5768; https://doi.org/10.3390/molecules16075754 - 6 Jul 2011

Cited by 34 | Viewed by 8279

Abstract

Adiponectin is an adipocyte-derived hormone that plays a pivotal role in the regulation of lipid and glucose metabolism. Up-regulation of adiponectin expression and production has been shown to benefit for metabolic disorders, including type 2 diabetes, hyperlipidemia, etc. The present study investigated whether [...] Read more.

Adiponectin is an adipocyte-derived hormone that plays a pivotal role in the regulation of lipid and glucose metabolism. Up-regulation of adiponectin expression and production has been shown to benefit for metabolic disorders, including type 2 diabetes, hyperlipidemia, etc. The present study investigated whether the novel polymethoxylated flavonoid pentamethylquercetin (PMQ), a member of polymethoxylated flavonoids family which is present in seabuckthorn (Hippophae L.) would affect adiponectin production in differentiated 3T3-L1 adipocytes. It was found that PMQ increased the adiponectin mRNA and protein expressions in adipocytes in time- and concentration-dependent manners. The PPARγ pathway plays a important roles in this effect of PMQ because blockade of PPARγ by GW9662 eliminates the PMQ-induced up-regulation of adiponectin expression. Furthermore, significant decreases of mRNA expression and secretion of TNF-α and IL-6 were also observed in PMQ-treated cells. Taken together, our study demonstrated that PMQ up-regulates adiponectin expression via a mechanism that implicates PPARγ together with TNF-α and IL-6, suggesting that PMQ might be a potential candidate for the treatment of metabolic diseases. Full article

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Open AccessCorrection

Drozdowska D., New Solid Phase Synthesis of Distamycin Analogues. Molecules, 2011, 16, 3066-3076

by Danuta Drozdowska

Molecules 2011, 16(7), 5753; https://doi.org/10.3390/molecules16075753 - 6 Jul 2011

Cited by 6 | Viewed by 3729

Abstract

The author wishes to make the following correction to this paper [1]: The correct author’s name is: Danuta Drozdowska. [...] Full article

(This article belongs to the Section Medicinal Chemistry)

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