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Molecules, Volume 15, Issue 9 (September 2010) – 56 articles , Pages 5840-6677

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132 KiB  
Article
Synthesis and Anti-Hyperlipidemic Evaluation of N‑(Benzoylphenyl)-5-fluoro-1H-indole-2-carboxamide Derivatives in Triton WR-1339-Induced Hyperlipidemic Rats
by Ghassan Shattat, Rania Al-Qirim, Yusuf Al-Hiari, Ghassan Abu Sheikha, Tariq Al-Qirim, Waseem El-Huneidi and Moyad Shahwan
Molecules 2010, 15(9), 5840-5849; https://doi.org/10.3390/molecules15095840 - 26 Aug 2010
Cited by 19 | Viewed by 9871
Abstract
The lipid-lowering activity of a series of novel N-(benzoylphenyl)-5-fluoro-1H-indole-2-carboxamide derivatives has been studied in Triton WR-1339-induced hyperlipidemia in rats. The test animals were divided into four groups: control, hyperlipidemic, compound + 4% DMSO [C1: N-(2-benzoylphenyl)-5-fluoro-1H-indole-2-carboxamide (1 [...] Read more.
The lipid-lowering activity of a series of novel N-(benzoylphenyl)-5-fluoro-1H-indole-2-carboxamide derivatives has been studied in Triton WR-1339-induced hyperlipidemia in rats. The test animals were divided into four groups: control, hyperlipidemic, compound + 4% DMSO [C1: N-(2-benzoylphenyl)-5-fluoro-1H-indole-2-carboxamide (1), C2: N-(3-benzoylphenyl)-5-fluoro-1H-indole-2-carboxamide (2), C3: N-(4-benzoylphenyl)-5-fluoro-1H-indole-2-carboxamide (3)]-treated and bezafibrate (BF)-treated. At a dose of 15 mg/Kg body weight, compounds 2, 3 and BF significantly reduced elevated plasma triglycerodes levels after 12 h. Moreover, high density lipoprotein-cholesterol levels were significantly increased in all treated groups after 12 h compared to the hyperlipidemic control group, except for C1 which was inactive. In sum, it may be stated that the results of the present study demonstrated new properties of some N-(benzoylphenyl)-5-fluoro-1H-indole-2-carboxamide derivatives as potent lipid lowering agents and these beneficial activities may contribute to their cardioprotective and antiatherosclerotic role. Full article
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173 KiB  
Article
Cytotoxic Tirucallane Triterpenoids from Melia azedarach Fruits
by Nikoletta G. Ntalli, Filippo Cottiglia, Carlos A. Bueno, Laura E. Alché, Marco Leonti, Simona Vargiu, Ersilia Bifulco, Urania Menkissoglu-Spiroudi and Pierluigi Caboni
Molecules 2010, 15(9), 5866-5877; https://doi.org/10.3390/molecules15095866 - 27 Aug 2010
Cited by 56 | Viewed by 11047
Abstract
The phytochemical investigation of the dichloromethane-soluble part of the methanol extract obtained from the fruits of Melia azedarach afforded one new tirucallane-type triterpene, 3-α-tigloylmelianol (1) and three known tirucallanes, melianone (2), 21-β-acetoxy-melianone (3), and [...] Read more.
The phytochemical investigation of the dichloromethane-soluble part of the methanol extract obtained from the fruits of Melia azedarach afforded one new tirucallane-type triterpene, 3-α-tigloylmelianol (1) and three known tirucallanes, melianone (2), 21-β-acetoxy-melianone (3), and methyl kulonate (4). The structure of the isolated compounds was mainly determined by 1D and 2D NMR experiments as well as HPLC-Q-TOF mass spectrometry. The cytotoxicity of the isolated compounds toward the human lung adenocarcinoma epithelial cell line A549 was determined, while no activity was observed against the phytonematode Meloidogyne incognita. Full article
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298 KiB  
Article
Modular Synthesis of Polyphenolic Benzofurans, and Application in the Total Synthesis of Malibatol A and Shoreaphenol
by David Y.-K. Chen, Qiang Kang and T. Robert Wu
Molecules 2010, 15(9), 5909-5927; https://doi.org/10.3390/molecules15095909 - 27 Aug 2010
Cited by 21 | Viewed by 8458
Abstract
A modular strategy for the synthesis of hexacyclic dimeric resveratrol polyphenolic benzofurans is reported. The developed synthetic technology was applied to the total synthesis of malibatol A, shoreaphenol, and other biologically relevant poly-phenols. Full article
(This article belongs to the Special Issue Diversity Oriented Synthesis)
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166 KiB  
Communication
An Efficient Procedure Based on a MW-Assisted Horner–Wadsworth-Emmons Reaction for the Synthesis of (Z)-3,3-Trisubstituted-a,b-unsaturated Esters
by Daniela Rossi, Anna Carnevale Baraglia, Massimo Serra, Ornella Azzolina and Simona Collina
Molecules 2010, 15(9), 5928-5942; https://doi.org/10.3390/molecules15095928 - 27 Aug 2010
Cited by 9 | Viewed by 7610
Abstract
A microwave-assisted HWE olefination process of readily accessible aryl-alkyl ketones has been developed to provide a rapid access to (Z)-3,3-trisubstituted-α,β-unsaturated methyl esters, key building blocks for the synthesis of biologically active compounds. Full article
(This article belongs to the Section Organic Chemistry)
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248 KiB  
Article
Antioxidant Properties of Marrubium peregrinum L. (Lamiaceae) Essential Oil
by Biljana Kaurinovic, Sanja Vlaisavljevic, Mira Popovic, Djendji Vastag and Maja Djurendic-Brenesel
Molecules 2010, 15(9), 5943-5955; https://doi.org/10.3390/molecules15095943 - 27 Aug 2010
Cited by 40 | Viewed by 9836
Abstract
The antioxidant activity of Marrubium peregrinum essential oil, collected from three different locations [Backo Gradiste - Rimski Sanac (No.1), Novi Knezevac (No.2) and Senta (No.3)] was evaluated as free radical scavenging capacity (RSC), together with inhibition on xanthine-oxidase and effects on lipid peroxidation [...] Read more.
The antioxidant activity of Marrubium peregrinum essential oil, collected from three different locations [Backo Gradiste - Rimski Sanac (No.1), Novi Knezevac (No.2) and Senta (No.3)] was evaluated as free radical scavenging capacity (RSC), together with inhibition on xanthine-oxidase and effects on lipid peroxidation (LP). RSC was assessed measuring the scavenging activity of the essential oils on 2,2-diphenyl-1-picrylhydrazyl (DPPH·), super oxide anion (O2·-), nitric-oxide (NO·) and hydroxyl (OH·) radicals. The activities of xanthine-oxidase (XOD) was determined by the nitrite method. Effects on LP were evaluated by following the activities of essential oils in the Fe2+/ascorbate induction system. Experimental results indicate that the essential oil of M. peregrinum from Senta (No.3) exhibited the strongest inhibitory effect, as the IC50 value was achieved with the lowest concentration. The same result was obtained in investigation of influence of essential oil on XOD and LP. The chemical profile of essential oil was evaluated by the means of gas chromatography-mass spectrometry (GC-MS). According to the analysis, the most powerful scavenging compounds were sesquiterpene hydrocarbons (b-caryophyllene, bicyclogermacrene and germacrene-D) and oxygenated sesquiterpenes (spathulenol and caryophyllene oxide). Full article
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356 KiB  
Article
In Vitro Antiophidian Properties of Dipteryx alata Vogel Bark Extracts
by Virgínia Sbrugnera Nazato, Leandro Rubem-Mauro, Nathalia Aparecida Gatto Vieira, Dimas Dos Santos Rocha, Júnior, Magali Glauzer Silva, Patricia Santos Lopes, Cháriston André Dal-Belo, Jose Carlos Cogo, Marcio Galdino Dos Santos, Maria Alice Da Cruz-Höfling and Yoko Oshima-Franco
Molecules 2010, 15(9), 5956-5970; https://doi.org/10.3390/molecules15095956 - 30 Aug 2010
Cited by 28 | Viewed by 13323
Abstract
Extracts from Dipteryx alata bark obtained with different solvents (hexane, dichloromethane, ethyl acetate and methanol) were mixed in vitro with Bothrops jararacussu (Bjssu, 40 μg/mL) and Crotalus durissus terrificus (Cdt, 15 μg/mL) snake venoms, and applied to a mouse phrenic nerve-diaphragm preparation to [...] Read more.
Extracts from Dipteryx alata bark obtained with different solvents (hexane, dichloromethane, ethyl acetate and methanol) were mixed in vitro with Bothrops jararacussu (Bjssu, 40 μg/mL) and Crotalus durissus terrificus (Cdt, 15 μg/mL) snake venoms, and applied to a mouse phrenic nerve-diaphragm preparation to evaluate the possible neutralization of venom effects. Cdt venom neurotoxic effect was not inhibited by any of the extracts, while the neurotoxic and myotoxic actions of Bjssu venom were decreased by the methanolic extract. This inhibition appears to be augmented by tannins. Dichloromethane bark extract inhibited ~40% of Bjssu venom effects and delayed blockade induced by Cdt. The methodology used to determine which extract was active allows inferring that: (i) phenolic acids and flavonoids contained in the methanolic extract plus tannins were responsible mostly for neutralization of Bjssu effects; (ii) terpenoids from the dichloromethane extract may participate in the anti-Cdt and anti-Bjssu venom effects; (iii) a given extract could not inhibit venoms from different species even if those belong to the same family, so it is improper to generalize a certain plant as antiophidian; (iv) different polarity extracts do not present the same inhibitory capability, thus demonstrating the need for characterizing both venom pharmacology and the phytochemistry of medicinal plant compounds Full article
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406 KiB  
Article
Evaluation of Antioxidant Potential of Lavandula x intermedia Emeric ex Loisel. 'Budrovka': A Comparative Study with L. angustifolia Mill.
by Biljana Blažeković, Sanda Vladimir-Knežević, Adelheid Brantner and Maja Bival Štefan
Molecules 2010, 15(9), 5971-5987; https://doi.org/10.3390/molecules15095971 - 30 Aug 2010
Cited by 70 | Viewed by 14213
Abstract
A Croatian indigenous cultivar of lavandin, Lavandula x intermedia 'Budrovka' (Lamiaceae) was studied for the phenolic acids, flavonoids, anthocyanins, procyanidins and total tannins, as well as total polyphenols content, in the flower, inflorescence stalk and leaf ethanolic extracts. Antioxidant potentials on these plant [...] Read more.
A Croatian indigenous cultivar of lavandin, Lavandula x intermedia 'Budrovka' (Lamiaceae) was studied for the phenolic acids, flavonoids, anthocyanins, procyanidins and total tannins, as well as total polyphenols content, in the flower, inflorescence stalk and leaf ethanolic extracts. Antioxidant potentials on these plant part extracts were assessed by the DPPH free radical scavenging activity, iron chelating activity, reducing power, lipid peroxidation inhibition properties and total antioxidant capacity assays. All results were compared with those of Lavandula angustifolia, the only member of the Lavandula genus officially used in modern phytotherapy. Based on the results of our parallel study, we may suggest that Lavandula x intermedia 'Budrovka' is as potent an antioxidant as Lavandula angustifolia and the antioxidant activity of the Lavandula extracts is mainly due to the presence of rosmarinic acid. A good correlation was found between the polyphenol contents and antioxidant activities of the extracts Full article
(This article belongs to the Special Issue Antioxidants)
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267 KiB  
Article
Screening of Natural Antioxidants from Traditional Chinese Medicinal Plants Associated with Treatment of Rheumatic Disease
by Ren-You Gan, Lei Kuang, Xiang-Rong Xu, Yuan Zhang, En-Qin Xia, Feng-Lin Song and Hua-Bin Li
Molecules 2010, 15(9), 5988-5997; https://doi.org/10.3390/molecules15095988 - 30 Aug 2010
Cited by 91 | Viewed by 13182
Abstract
In order to find new sources of natural antioxidants, the antioxidant capacities of 50 medicinal plants associated with treatment of rheumatic diseases were systemically evaluated using the ferric-reducing antioxidant power (FRAP) and Trolox equivalent antioxidant capacity (TEAC) assays, and their total phenolic contents [...] Read more.
In order to find new sources of natural antioxidants, the antioxidant capacities of 50 medicinal plants associated with treatment of rheumatic diseases were systemically evaluated using the ferric-reducing antioxidant power (FRAP) and Trolox equivalent antioxidant capacity (TEAC) assays, and their total phenolic contents were measured by the Folin–Ciocalteu method. Their antioxidant activities of some of these plants were analyzed for the first time. The FRAP and TEAC assay results suggested that the antioxidant compounds in these plants possessed free radicals scavenging activity and oxidant reducing power. A positive linear correlation between antioxidant capacities and total phenolic contents implied that phenolic compounds in these plants could be the main components contributing to the observed activities. The results showed that Geranium wilfordii, Loranthus parasiticus, Polygonum aviculare, Pyrrosia sheaeri, Sinomenium acutum and Tripterygium wilfordii possessed the highest antioxidant capacities and total phenolic content among 50 plants tested, and could be rich potential sources of natural antioxidants. Full article
(This article belongs to the Special Issue Antioxidants)
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276 KiB  
Article
Preparative Separation of Phenolic Compounds from Halimodendron halodendron by High-Speed Counter-Current Chromatography
by Jihua Wang, Haifeng Gao, Jianglin Zhao, Qi Wang, Ligang Zhou, Jianguo Han, Zhu Yu and Fuyu Yang
Molecules 2010, 15(9), 5998-6007; https://doi.org/10.3390/molecules15095998 - 31 Aug 2010
Cited by 42 | Viewed by 14006
Abstract
Three phenolic compounds, p-hydroxybenzoic acid (1), isorhamnetin-3-O-β-D-rutinoside (2), and 3,3'-di-O-methylquercetin (5), along with a phenolic mixture were successfully separated from the ethyl acetate crude extract of Halimodendron halodendron by high-speed counter-current chromatography [...] Read more.
Three phenolic compounds, p-hydroxybenzoic acid (1), isorhamnetin-3-O-β-D-rutinoside (2), and 3,3'-di-O-methylquercetin (5), along with a phenolic mixture were successfully separated from the ethyl acetate crude extract of Halimodendron halodendron by high-speed counter-current chromatography (HSCCC) with chloroform-methanol-water-acetic acid (4:3:2:0.05, v/v) as the two-phase solvent system. The phenolic mixture from HSCCC was further separated by preparative HPLC and purified by Sephadex LH-20 to afford quercetin (3) and 3-O-methylquercetin (4). Seven hundred mg of ethyl acetate crude extract was separated by HSCCC to obtain six fractions which were then analyzed by high performance liquid chromatography (HPLC). The HSCCC separation obtained total of 80 mg of the mixture of quercetin (3) and 3-O-methylquercetin (4) (26.43% and 71.89%, respectively) in fraction 2, 14 mg of 3,3'-di-O-methylquercetin (5) at 95.14% of purity in fraction 3, 15 mg of p-hydroxybenzoic acid (1) at 92.83% of purity in fraction 5, 12 mg of isorhamnetin-3-O-β-D-rutinoside (2) at 97.99% of purity in fraction 6. This is the first time these phenolic compounds have been obtained from H. halodendron, and their chemical structures identified by means of physicochemical and spectrometric analysis. Full article
(This article belongs to the Special Issue Phenolics and Polyphenolics)
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849 KiB  
Article
Assessment of Euphorbia hirta L. Leaf, Flower, Stem and Root Extracts for Their Antibacterial and Antifungal Activity and Brine Shrimp Lethality
by Mohammad Abu Basma Rajeh, Zakaria Zuraini, Sreenivasan Sasidharan, Lachimanan Yoga Latha and Santhanam Amutha
Molecules 2010, 15(9), 6008-6018; https://doi.org/10.3390/molecules15096008 - 31 Aug 2010
Cited by 74 | Viewed by 16607
Abstract
The antimicrobial activities of the methanolic extracts of Euphorbia hirta L leaves, flowers, stems and roots were evaluated against some medically important bacteria and yeast using the agar disc diffusion method. Four Gram positive (Staphylococcus aureus, Micrococcus sp., Bacillus subtilis and [...] Read more.
The antimicrobial activities of the methanolic extracts of Euphorbia hirta L leaves, flowers, stems and roots were evaluated against some medically important bacteria and yeast using the agar disc diffusion method. Four Gram positive (Staphylococcus aureus, Micrococcus sp., Bacillus subtilis and Bacillus thuringensis), four Gram negative (Escherichia coli, Klebsiella pneumonia, Salmonella typhi and P. mirabilis) and one yeast (Candida albicans) species were screened. Inhibition zones ranged between 16–29 mm. Leaves extract inhibited the growth of all tested microorganisms with large zones of inhibition, followed by that of flowers, which also inhibited all the bacteria except C. albicans. The most susceptible microbes to all extracts were S. aureus and Micrococcus sp. Root extract displayed larger inhibition zones against Gram positive bacteria than Gram negative bacteria and had larger inhibition zones compared to stem extract. The lowest MIC values were obtained with E. coli and C. albicans (3.12 mg/mL), followed by S. aureus (12.50 mg/mL) and P. mirabilis (50.00 mg/mL). All the other bacteria had MIC values of 100.00 mg/mL. Scanning Electron Microscopic (SEM) studies revealed that the cells exposed to leaf extract displayed a rough surface with multiple blends and invaginations which increased with increasing time of treatment, and cells exposed to leaf extract for 36 h showed the most damage, with abundant surface cracks which may be related to final cell collapse and lossThe antimicrobial activities of the methanolic extracts of Euphorbia hirta L leaves, flowers, stems and roots were evaluated against some medically important bacteria and yeast using the agar disc diffusion method. Four Gram positive (Staphylococcus aureus, Micrococcus sp., Bacillus subtilis and Bacillus thuringensis), four Gram negative (Escherichia coli, Klebsiella pneumonia, Salmonella typhi and P. mirabilis) and one yeast (Candida albicans) species were screened. Inhibition zones ranged between 16–29 mm. Leaves extract inhibited the growth of all tested microorganisms with large zones of inhibition, followed by that of flowers, which also inhibited all the bacteria except C. albicans. The most susceptible microbes to all extracts were S. aureus and Micrococcus sp. Root extract displayed larger inhibition zones against Gram positive bacteria than Gram negative bacteria and had larger inhibition zones compared to stem extract. The lowest MIC values were obtained with E. coli and C. albicans (3.12 mg/mL), followed by S. aureus (12.50 mg/mL) and P. mirabilis (50.00 mg/mL). All the other bacteria had MIC values of 100.00 mg/mL. Scanning Electron Microscopic (SEM) studies revealed that the cells exposed to leaf extract displayed a rough surface with multiple blends and invaginations which increased with increasing time of treatment, and cells exposed to leaf extract for 36 h showed the most damage, with abundant surface cracks which may be related to final cell collpase and loss of function. Time-kill assay of C. albicans indicated a primarily fungicidal effect at 1- and 2-fold MIC. E. hirta extracts had LC50 values of 0.71, 0.66, 0.41 and 0.03 mg/mL for stems, leaves, roots and flowers, respectively against Artemia salina. Hence, these plants can be used to discover new bioactive natural products that may serve as leads in the development of new pharmaceuticals. Full article
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206 KiB  
Article
Synthesis of [4-(2-Hydroxyphenyl)thiazol-2-yl]methanones as Potential Bioisosteres of Salicylidene Acylhydrazides
by J. Mikael Hillgren, Markus K. Dahlgren, Tam M. To and Mikael Elofsson
Molecules 2010, 15(9), 6019-6034; https://doi.org/10.3390/molecules15096019 - 31 Aug 2010
Cited by 5 | Viewed by 5373
Abstract
A focused library of [4-(2-hydroxyphenyl)thiazol-2-yl]methanones was prepared in a four-step synthesis with the aim to obtain potent inhibitors of type III secretion in Gram-negative bacteria. The compounds are potential bioisosteres of salicylidene acylhydrazides that are a known class of type III secretion inhibitors. [...] Read more.
A focused library of [4-(2-hydroxyphenyl)thiazol-2-yl]methanones was prepared in a four-step synthesis with the aim to obtain potent inhibitors of type III secretion in Gram-negative bacteria. The compounds are potential bioisosteres of salicylidene acylhydrazides that are a known class of type III secretion inhibitors. Full article
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637 KiB  
Article
Antiradical and Cytoprotective Activities of Several C-Geranyl-substituted Flavanones from Paulownia tomentosa Fruit
by Aleš Zima, Jan Hošek, Jakub Treml, Jan Muselík, Pavel Suchý, Gabriela Pražanová, Ana Lopes and Milan Žemlička
Molecules 2010, 15(9), 6035-6049; https://doi.org/10.3390/molecules15096035 - 31 Aug 2010
Cited by 43 | Viewed by 10890
Abstract
Antiradical and cytoprotective activities of several flavanones isolated from Paulownia tomentosa (Thunb.) Steud. (Scrophulariaceae) have been evaluated using different in vitro and in vivo methods. The capacity of flavanones to scavenge radicals was measured in vitro by means of DPPH and ABTS assays, [...] Read more.
Antiradical and cytoprotective activities of several flavanones isolated from Paulownia tomentosa (Thunb.) Steud. (Scrophulariaceae) have been evaluated using different in vitro and in vivo methods. The capacity of flavanones to scavenge radicals was measured in vitro by means of DPPH and ABTS assays, the inhibition of hydroxyl radicals produced in Fenton reactions, FRAP, scavenging superoxide radicals using enzymatic and nonenzymatic assays and the inhibition of peroxynitrite-induced nitration of tyrosine. The in vivo testing involved measuring the cytoprotective effect of chosen flavanones against alloxan-induced diabetes in mice. The activity of tested compounds was expressed either as a Trolox® equivalent or was compared with rutin or morine as known antioxidant compounds. The highest activity in most tests was observed for diplacone and 3´-O-methyl-5´-hydroxydiplacone, and the structure vs. the antioxidant activity relationship of geranyl or prenyl-substituted flavonoids with different substitutions at the B and C ring was discussed. Full article
(This article belongs to the Special Issue Antioxidants)
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197 KiB  
Article
Heterocyclic Analogues of Xanthone and Xanthione. 1H-Pyrano[2,3-c:6,5-c]dipyrazol-4(7H)-ones and Thiones: Synthesis and NMR Data
by Barbara Datterl, Nicole Tröstner, Dorota Kucharski and Wolfgang Holzer
Molecules 2010, 15(9), 6106-6126; https://doi.org/10.3390/molecules15096106 - 1 Sep 2010
Cited by 20 | Viewed by 8180
Abstract
The synthesis of the title compounds is described. Reaction of 1-substituted 2-pyrazolin-5-ones with 5-chloro-1-phenyl-1H-pyrazole-4-carbonyl chloride or 5-chloro-3-methyl-1-phenyl-1H-pyrazole-4-carbonyl chloride, respectively, using calcium hydroxide in refluxing 1,4-dioxane gave the corresponding 4-heteroaroylpyrazol-5-ols, which were cyclized into 1H-pyrano[2,3-c:6,5-c]dipyrazol-4(7H)-ones by treatment with K2CO3/DMF. The latter were converted into [...] Read more.
The synthesis of the title compounds is described. Reaction of 1-substituted 2-pyrazolin-5-ones with 5-chloro-1-phenyl-1H-pyrazole-4-carbonyl chloride or 5-chloro-3-methyl-1-phenyl-1H-pyrazole-4-carbonyl chloride, respectively, using calcium hydroxide in refluxing 1,4-dioxane gave the corresponding 4-heteroaroylpyrazol-5-ols, which were cyclized into 1H-pyrano[2,3-c:6,5-c]dipyrazol-4(7H)-ones by treatment with K2CO3/DMF. The latter were converted into the corresponding thiones upon reaction with Lawesson’s reagent. Detailed NMR spectroscopic investigations (1H, 13C, 15N) of the ring systems and their precursors are presented. Full article
(This article belongs to the Special Issue Advances in Heterocyclic Chemistry)
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115 KiB  
Communication
Screening of Filamentous Fungi to Identify Biocatalysts for Lupeol Biotransformation
by Tatiane C. de Carvalho, Aline M. Polizeli, Izabel C. C. Turatti, Marcela E. Severiano, Carlos E. de Carvalho, Sérgio R. Ambrósio, Antônio E. M. Crotti, Uir S. de Figueiredo, Paulo C. Vieira and Niege A. J. C. Furtado
Molecules 2010, 15(9), 6140-6151; https://doi.org/10.3390/molecules15096140 - 1 Sep 2010
Cited by 30 | Viewed by 12204
Abstract
The goal of the study was to evaluate the ability of filamentous fungi to biotransform the pentacyclic triterpene lupeol. The microbial transformations were carried out in shake flasks in different media. Experiments were also run with control flasks. Samples of each culture were [...] Read more.
The goal of the study was to evaluate the ability of filamentous fungi to biotransform the pentacyclic triterpene lupeol. The microbial transformations were carried out in shake flasks in different media. Experiments were also run with control flasks. Samples of each culture were taken every 24 hours, extracted with ethyl acetate, and analyzed by GC-MS. The biotransformation of lupeol by Aspergillus ochraceus and Mucor rouxii afforded two compounds in each culture, which were detected in the cultures developed for more than seven days only in the Koch’s K1 medium. The obtained data demonstrated that A. ochraceus is a good biocatalyst to introduce double bonds in the lupeol structure, whereas M. rouxii exhibits ability to biocatalyze oxygen insertions in that pentacyclic triterpene. Mass spectrometry was demonstrated to be an efficient analytical method to select promising biocatalysts for the compound investigated in this study. The biotransformation processes were influenced by the culture medium and incubation period. The obtained results open the perspective of using A. ochraceus and M. rouxii in pentacyclic triterpene biotransformations. Full article
(This article belongs to the Section Natural Products Chemistry)
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241 KiB  
Article
Antioxidant Capacity of Pure Compounds and Complex Mixtures Evaluated by the ORAC-Pyrogallol Red Assay in the Presence of Triton X-100 Micelles
by Max Romero, Benjamin Rojano, Jaime Mella-Raipán, Carlos David Pessoa-Mahana, Eduardo Lissi and Camilo López-Alarcón
Molecules 2010, 15(9), 6152-6167; https://doi.org/10.3390/molecules15096152 - 1 Sep 2010
Cited by 32 | Viewed by 10817
Abstract
The protective effect of different antioxidants and complex mixtures on the consumption of pyrogallol red (PGR) induced by peroxyl radicals was studied in the absence and presence of Triton X-100 micelles. The presence of micelles decreased significantly the protection of PGR afforded by [...] Read more.
The protective effect of different antioxidants and complex mixtures on the consumption of pyrogallol red (PGR) induced by peroxyl radicals was studied in the absence and presence of Triton X-100 micelles. The presence of micelles decreased significantly the protection of PGR afforded by lipophilic antioxidants (β-carotene, octyl gallate), while no effect of micelles was observed for hydrophilic antioxidants such as Trolox, caffeic acid, gallic acid, and ascorbic acid. In the presence of complex mixtures a clear effect of Triton X-100 micelles was also observed in the protection afforded by wines, tea infusions, and seed extracts of Eugenia jambolana and Myrciaria cauliflora. On the other hand, no effect of micelles was observed for orange juice and pulp fruit extracts. The ORAC (Oxygen Radical Absorbance Capacity) index was evaluated in the absence (ORAC-PGR) and presence of Triton X-100 micelles (ORAC-PGRMIC). Triton X-100 micelles affect ORAC-PGR values of antioxidants in a lipophilicity-dependent way. From the obtained results, we conclude that ORAC-PGR and ORAC-PGRMIC assays could be considered as an alternative to estimate the antioxidant ability (ORAC-PGR) and to infer the association to Triton X-100 micelles (ORAC-PGR/ORAC-PGRMIC) of pure antioxidants and their complex mixtures. Full article
(This article belongs to the Special Issue Antioxidants)
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262 KiB  
Article
Comparative Study of the Leaf Volatiles of Arctostaphylos uva-ursi (L.) Spreng. and Vaccinium vitis-idaea L. (Ericaceae)
by Niko Radulović, Polina Blagojević and Radosav Palić
Molecules 2010, 15(9), 6168-6185; https://doi.org/10.3390/molecules15096168 - 2 Sep 2010
Cited by 60 | Viewed by 10500
Abstract
The first GC and GC/MS analyses of the essential oils hydrodistilled from dry leaves of Arctostaphylos uva-ursi and Vaccinium vitis-idaea enabled the identification of 338 components in total (90.4 and 91.7% of the total GC peak areas, respectively). Terpenoids, fatty acids, fatty acid- [...] Read more.
The first GC and GC/MS analyses of the essential oils hydrodistilled from dry leaves of Arctostaphylos uva-ursi and Vaccinium vitis-idaea enabled the identification of 338 components in total (90.4 and 91.7% of the total GC peak areas, respectively). Terpenoids, fatty acids, fatty acid- and carotenoid derived compounds were predominant in the two samples. Both oils were characterized by high relative percentages of α-terpineol and linalool (4.7-17.0%). Compositional data on the volatiles of the presently analyzed and some other Ericaceae taxa (literature data) were mutually compared by means of multivariate statistical analyses (agglomerative hierarchical cluster analysis and principal component analysis). This was done in order to determine, based on the essential oil profiles, possible mutual relationships of the taxa within the family, especially that of species from the genera Arctostaphylos and Vaccinium. Results of the chemical and statistical analyses pointed to a strong relation between the genera Vaccinium and Arctostaphylos. Full article
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127 KiB  
Article
L-(-)-(N-trans-Cinnamoyl)-arginine, an Acylamino Acid from Glinus oppositifolius (L.) Aug. DC.
by Poolsak Sahakitpichan, Wannaporn Disadee, Somsak Ruchirawat and Tripetch Kanchanapoom
Molecules 2010, 15(9), 6186-6192; https://doi.org/10.3390/molecules15096186 - 2 Sep 2010
Cited by 19 | Viewed by 9250
Abstract
An amino acid derivative, L-(-)-(N-trans-cinnamoyl)-arginine, was isolated from the whole plant of Glinus oppositifolius (L.) Aug. DC. along with kaempferol 3-O-galactopyranoside, isorhamnetin 3-O-b-D-xylopyranosyl-(1®2)-b-D-galactopyranoside, vitexin, vicenin-2, adenosine and L-phenylalanine. The structure determinations were based on analyses of chemical and spectroscopic methods. Full article
(This article belongs to the Section Natural Products Chemistry)
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1470 KiB  
Article
Antioxidant Activities of Celery and Parsley Juices in Rats Treated with Doxorubicin
by Jovanka Kolarovic, Mira Popovic, Janka Zlinská, Svetlana Trivic and Matilda Vojnovic
Molecules 2010, 15(9), 6193-6204; https://doi.org/10.3390/molecules15096193 - 3 Sep 2010
Cited by 50 | Viewed by 10508
Abstract
We have examined the influence of diluted pure celery and parsley leaf and root juices and their combinations with doxorubicin on the antioxidant status [as measured by the content of reduced glutathione (GSH) and ferric reducing antioxidant power (FRAP)] in liver homogenate and [...] Read more.
We have examined the influence of diluted pure celery and parsley leaf and root juices and their combinations with doxorubicin on the antioxidant status [as measured by the content of reduced glutathione (GSH) and ferric reducing antioxidant power (FRAP)] in liver homogenate and hemolysate and on the contents of cytochrome P450 in liver homogenate. It was found that doxorubicin significantly decreased the content of reduced glutathione and the total antioxidative status (FRAP) in liver homogenate and hemolysate, while celery and parsley juices alone and in combination with doxorubicin had different actions. Doxorubicin and celery juice had no effect on content of cytochrome P450. However, in combination with doxorubicin, parsley root juice significant increased, and parsley leaves juice decreased the cytochrome P450 content (compared to doxorubicin treated animals). Only parsley root juice significantly increased the content of cytochrome P450. Full article
(This article belongs to the Section Medicinal Chemistry)
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107 KiB  
Article
Synthesis of New 2-(2´-Hydroxyaryl)benzotriazoles and Evaluation of Their Photochemical Behavior as Potential UV-Filters
by Renata Farkas, Virginie Lhiaubet-Vallet, Jordi Corbera, Mercedesz Törincsi, Olga Gorchs, Carles Trullas, Oscar Jiménez, Miguel A. Miranda and Lajos Novak
Molecules 2010, 15(9), 6205-6216; https://doi.org/10.3390/molecules15096205 - 3 Sep 2010
Cited by 20 | Viewed by 7688
Abstract
Two new 2-(2´-hydroxyaryl)benzotriazole derivatives were synthesized and studied by photophysical and photochemical techniques in order to assess their ability to act as UV-filters. The absorption and emission properties of both compounds were determined in solvents of different polarity. In non polar solvent, a [...] Read more.
Two new 2-(2´-hydroxyaryl)benzotriazole derivatives were synthesized and studied by photophysical and photochemical techniques in order to assess their ability to act as UV-filters. The absorption and emission properties of both compounds were determined in solvents of different polarity. In non polar solvent, a photoinduced excited state intramolecular proton transfer was established leading to efficient non radiative dissipation of UV-energy. In addition, the compounds considered were photostable under irradiation with simulated sunlight. Full article
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383 KiB  
Article
Characterization of the Active Constituents in Shixiao San Using Bioactivity Evaluation Followed by UPLC-QTOF and Markerlynx Analysis
by Wei Zhou, Shu-Lan Su, Jin-Ao Duan, Jian-Ming Guo, Da-Wei Qian, Er-Xin Shang and Jin Zhang
Molecules 2010, 15(9), 6217-6230; https://doi.org/10.3390/molecules15096217 - 3 Sep 2010
Cited by 15 | Viewed by 10893
Abstract
Shixiao San is a famous Traditional Chinese Medicine (TCM) formula that has been used for a long time for the treatment of gynecological diseases. In this paper, the active constituents in Shixiao San were characterized by using bioactivity evaluation followed by UPLC-QTOF and [...] Read more.
Shixiao San is a famous Traditional Chinese Medicine (TCM) formula that has been used for a long time for the treatment of gynecological diseases. In this paper, the active constituents in Shixiao San were characterized by using bioactivity evaluation followed by UPLC-QTOF and MarkerlynxTM analysis. The analgesic activities of two extracts of Shixiao San were evaluated using the hot-plate test, acetic acid-induced writhing and dysmenorrhea mice model. The results showed that the analgesic activity of Shixiao San vinegary extract (boiling vinegar) was superior to the aqueous extract. UPLC-QTOF and MarkerlynxTM analytic results showed that the process of boiling in vinegar may improve the dissolution of Shixiao San flavanoids, and these flavanoids may contribute to the observed analgesic activity. This work demonstrated that UPLC/QTOFMS and MarkerlynxTM could serve as new methods for fast generation and automated analysis of information-rich data from Chinese herbal medicines. Full article
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325 KiB  
Article
Identification and Concentration of Some Flavonoid Components in Malaysian Young Ginger (Zingiber officinale Roscoe) Varieties by a High Performance Liquid Chromatography Method
by Ali Ghasemzadeh, Hawa Z E Jaafar and Asmah Rahmat
Molecules 2010, 15(9), 6231-6243; https://doi.org/10.3390/molecules15096231 - 3 Sep 2010
Cited by 61 | Viewed by 16559
Abstract
Flavonoids make up one of the most pervasive groups of plant phenolics. Due to their importance in plants and human health, it would be useful to have a better understanding of flavonoid concentration and biological activities that could indicate their potentials as therapeutic [...] Read more.
Flavonoids make up one of the most pervasive groups of plant phenolics. Due to their importance in plants and human health, it would be useful to have a better understanding of flavonoid concentration and biological activities that could indicate their potentials as therapeutic agents, and also for predicting and controlling the quality of medicinal herbs. Ginger (Zingiber officinale Roscoe) is a famous and widely used herb, especially in Asia, that contains several interesting bioactive constituents and possesses health promoting properties. In this study, total flavonoids and some flavonoid components including quercetin, rutin, catechin, epicatechin, kaempferol and naringenin were extracted from the leaves and rhizomes of two varieties of Zingiber officinale (Halia Bentong and Halia Bara) at three different growth points (8, 12 and 16 weeks after planting), and analyzed by a high performance liquid chromatography (HPLC) method in order to determine the potential of the subterranean part of the young ginger. The results showed that Halia Bara had a higher content of flavonoids in the leaves and rhizomes as compared to Halia Bentong. In both varieties, the concentration of flavonoids in the leaves decreased (Halia Bentong, 42.3%; Halia Bara 36.7%), and in the rhizomes it increased (Halia Bentong 59.6%; Halia Bara 60.1%) as the growth period increased. Quercetin was abundant in both varieties. The antioxidant activity determined by the 1,1-diphenyl-2-picryl-hydrazyl (DPPH) assay showed high activities (65.7%) in the leaves of Halia Bara at 8 weeks after planting. Results suggested a good flavonoid content and antioxidant activity potential in ginger leaves at 8 weeks after planting. The leaves of these ginger varieties could be useful for both food flavourings and in traditional medicine. Full article
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193 KiB  
Article
Evaluation of Crocus sativus L. Stigma Phenolic and Flavonoid Compounds and Its Antioxidant Activity
by Ehsan Karimi, Ehsan Oskoueian, Rudi Hendra and Hawa Z.E. Jaafar
Molecules 2010, 15(9), 6244-6256; https://doi.org/10.3390/molecules15096244 - 6 Sep 2010
Cited by 196 | Viewed by 19878
Abstract
Saffron (Crocus sativus L.) belongs to the Iridaceae family. The stigma of saffron has been widely used as spice, medicinal plant, and food additive in the Mediterranean and Subtropical countries. Recently, attention has been paid to the identification of new sources of [...] Read more.
Saffron (Crocus sativus L.) belongs to the Iridaceae family. The stigma of saffron has been widely used as spice, medicinal plant, and food additive in the Mediterranean and Subtropical countries. Recently, attention has been paid to the identification of new sources of safe natural antioxidants for the food industry. The antioxidant activities of spices are mainly attributed to their phenolic and flavonoid compounds. Saffron is one of the spices believed to possess antioxidant properties, but information on its antioxidant activity and phenolic, flavonoids compound are rather limited, therefore this research was carried out to evaluate the antioxidant activity of saffron stigmas extracted with different solvents. The phenolic and flavonoid compounds of saffron were also examined using reversed phase (RP)-HPLC. Results showed that saffron stigma possess antioxidant activity. The free radical scavenging and ferric reducing power activities were higher for the methanolic extract of saffron stigma at a concentration of 300 μg/mL, with values of 68.2% and 78.9%, respectively, as compared to the corresponding boiling water and ethanolic extracts, but the activities were lower than those of antioxidant standards such as BHT and α-tocopherol. The obtained total phenolics value for methanolic saffron extract was 6.54 ± 0.02 mg gallic acid equivalent (GAE)/g dry weight (DW), and for total flavonoids, 5.88 ± 0.12 mg rutin equivalent/g DW, which were also higher than values obtained from the ethanolic and boiling water extracts. In addition, the RP-HPLC analyses indicated the presence of gallic acid and pyrogallol as two bioactive compounds. In summary, saffron stigmas showed antioxidant activity and methanol appeared to be the best solvent to extract the active components, among which the presence of gallic acid and pyrogallol might contribute towards the stigma’s antioxidant properties. Hence, saffron stigma could be applied as a natural antioxidant source for industrial purposes. Full article
(This article belongs to the Special Issue Antioxidants)
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976 KiB  
Article
Microwave Irradiation-Assisted Synthesis of a Novel Crown Ether Crosslinked Chitosan as a Chelating Agent for Heavy Metal Ions (M+n)
by Awwad A. Radwan, Fars K. Alanazi and Ibrahim A. Alsarra
Molecules 2010, 15(9), 6257-6268; https://doi.org/10.3390/molecules15096257 - 6 Sep 2010
Cited by 34 | Viewed by 9963
Abstract
Microwave irradiation was used to obtain a di-Schiff base type crosslinked chitosan dibenzocrown ether (CCdBE) via the reaction between the –NH2 and –CHO groups in chitosan and 4,4′-diformyldibenzo-18-c-6, respectively. The structure of the synthesized compound was characterized by elemental analysis, solid state [...] Read more.
Microwave irradiation was used to obtain a di-Schiff base type crosslinked chitosan dibenzocrown ether (CCdBE) via the reaction between the –NH2 and –CHO groups in chitosan and 4,4′-diformyldibenzo-18-c-6, respectively. The structure of the synthesized compound was characterized by elemental analysis, solid state 13C-NMR and FT-IR spectra analysis. The results showed that the mass fraction of nitrogen in the CCdBE derivative was much lower than those of chitosan. The FT-IR spectra of CCdBE revealed the expected chitosan-crown ether structure, as evidenced by the presence of the characteristic C=N and Ar peaks. The adsorption properties of CCdBE for Pd2+ and Hg2+ were investigated and the results demonstrated that the adsorbent has both desirable adsorption properties with a high particular adsorption selectivity for Hg2+ when in the presence of Pb2+ as well as selectivity coefficients for metal ions of KHg2+ /Pb2+ = 8.00 and KHg 2+/Pb2+ = 10.62 at pH values of 4 and 6, respectively. The reusability tests for CCdBE for Pb2+ adsorption showed that complete recovery of the ion was possible with CCdBE after 10-multiple reuses while CTS had no reusability at acidic solution because of its higher dissolution. The studied features of CCdBE suggested that the material could be considered as a new adsorbent. It is envisaged that the crosslinking of CTS into CCdBE would enhance practicality and effectiveness of adsorption in ion separation and removal procedures. Full article
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1594 KiB  
Article
Content of Phenolic Compounds and Antioxidant Capacity in Fruits of Apricot Genotypes
by Jiri Sochor, Ondrej Zitka, Helena Skutkova, Dusan Pavlik, Petr Babula, Boris Krska, Ales Horna, Vojtech Adam, Ivo Provaznik and Rene Kizek
Molecules 2010, 15(9), 6285-6305; https://doi.org/10.3390/molecules15096285 - 7 Sep 2010
Cited by 102 | Viewed by 14777
Abstract
Research on natural compounds is increasingly focused on their effects on human health. In this study, we were interested in the evaluation of nutritional value expressed as content of total phenolic compounds and antioxidant capacity of new apricot (Prunus armeniaca L.) genotypes [...] Read more.
Research on natural compounds is increasingly focused on their effects on human health. In this study, we were interested in the evaluation of nutritional value expressed as content of total phenolic compounds and antioxidant capacity of new apricot (Prunus armeniaca L.) genotypes resistant against Plum pox virus (PPV) cultivated on Department of Fruit Growing of Mendel University in Brno. Fruits of twenty one apricot genotypes were collected at the onset of consumption ripeness. Antioxidant capacities of the genotypes were determined spectrometrically using DPPH• (1,1-diphenyl-2-picryl-hydrazyl free radicals) scavenging test, TEAC (Trolox Equivalent Antioxidant Capacity), and FRAP (Ferric Reducing Antioxidant Power)methods. The highest antioxidant capacities were determined in the genotypes LE-3228 and LE-2527, the lowest ones in the LE-985 and LE-994 genotypes. Moreover, close correlation (r = 0.964) was determined between the TEAC and DPPH assays. Based on the antioxidant capacity and total polyphenols content, a clump analysis dendrogram of the monitored apricot genotypes was constructed. In addition, we optimized high performance liquid chromatography coupled with tandem electrochemical and spectrometric detection and determined phenolic profile consisting of the following fifteen phenolic compounds: gallic acid, 4-aminobenzoic acid, chlorogenic acid, ferulic acid, caffeic acid, procatechin, salicylic acid, p-coumaric acid, the flavonols quercetin and quercitrin, the flavonol glycoside rutin, resveratrol, vanillin, and the isomers epicatechin, (–)- and (+)- catechin. Full article
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323 KiB  
Article
Isolation and Crystal Structure of Marcanine A from Polyalthia plagioneura
by Bingjing Liu, Lin Wang, Guangying Chen, Changri Han and Jing Wang
Molecules 2010, 15(9), 6349-6356; https://doi.org/10.3390/molecules15096349 - 9 Sep 2010
Cited by 10 | Viewed by 8192
Abstract
Marcanine A was isolated from the stems of Polyalthia plagioneura as light yellow crystals. The molecular and crystal structures have been determined by 1D,2D-NMR and X-ray diffraction analysis. It crystallizes in the triclinic system, space group P-1 with a = 5.2140(5)Å, b = [...] Read more.
Marcanine A was isolated from the stems of Polyalthia plagioneura as light yellow crystals. The molecular and crystal structures have been determined by 1D,2D-NMR and X-ray diffraction analysis. It crystallizes in the triclinic system, space group P-1 with a = 5.2140(5)Å, b = 10.1871(11)Å, c = 11.0709(13)Å, α = 110.452(2)º, β = 103.376(2)°, γ = 90.1870(10)°, V = 533.74(10)Å3, Z = 2. There are three intermolecular hydrogen bonds in a unit cell. It displays some inhibitory activities towards four kinds of human tumor cells, including BEL-7402, K562, SPCA-1and SGC-7409. Full article
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188 KiB  
Article
Two New Flavones from Tridax procumbens Linn
by Runsheng Xu, Jing Zhang and Ke Yuan
Molecules 2010, 15(9), 6357-6364; https://doi.org/10.3390/molecules15096357 - 9 Sep 2010
Cited by 20 | Viewed by 9742
Abstract
Two new flavones, 8,3′-dihydroxy-3,7,4′-trimethoxy-6-O-β-D-glucopyranosyl flavone (1) and 6,8,3′-trihydroxy-3,7,4′-trimethoxyflavone (2) were isolated from Tridax procumbens Linn., together with the four known compounds puerarin (3), esculetin (4), oleanolic acid (5 [...] Read more.
Two new flavones, 8,3′-dihydroxy-3,7,4′-trimethoxy-6-O-β-D-glucopyranosyl flavone (1) and 6,8,3′-trihydroxy-3,7,4′-trimethoxyflavone (2) were isolated from Tridax procumbens Linn., together with the four known compounds puerarin (3), esculetin (4), oleanolic acid (5) and betulinic acid (6). The structures of the two new flavones were elucidated based on chemical analysis and spectral methods (IR, 1D and 2D NMR, ESI-MS, HR-ESI-MS). The antioxidant activity of the two new flavones were evaluated by two methods, the 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activity and ferric reducing antioxidant power (FRAP) assays, and the data showed that compounds 1 and 2 have certain antioxidant activity, with the antioxidant activity of compound 2 being stronger than that of compound 1. Full article
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Article
Microwave Assisted Extraction of Phenolic Compounds from Four Different Spices
by Monica Gallo, Rosalia Ferracane, Giulia Graziani, Alberto Ritieni and Vincenzo Fogliano
Molecules 2010, 15(9), 6365-6374; https://doi.org/10.3390/molecules15096365 - 9 Sep 2010
Cited by 127 | Viewed by 14292
Abstract
Spices and herbs are known not only for their taste, aroma and flavour, but also for their medical properties and value. Both spices and herbs have been used for centuries in traditional medical systems to cure various kinds of illnesses such as common [...] Read more.
Spices and herbs are known not only for their taste, aroma and flavour, but also for their medical properties and value. Both spices and herbs have been used for centuries in traditional medical systems to cure various kinds of illnesses such as common cold, diabetes, cough and cancers. The aim of this work was the comparison between two different extractive techniques in order to get qualitative and quantitative data regarding bioactive compounds of four different spices (Cinnamomum zeylanicum, Coriandrum sativum, Cuminum cyminum, Crocus sativus). The plants were extracted employing ultrasonication and microwave-assisted extractions. The efficiency of extraction of bioactive compounds obtained with the microwave extraction process was in general about four times higher than that resulting from sonication extraction. The various extracts obtained were analyzed for their antioxidant activity using ABTS, DPPH and FRAP assays and for their total polyphenolic content. It can be concluded that microwave-assisted extractions provide significant advantages in terms of extraction efficiency and time savings. Full article
(This article belongs to the Special Issue Phytochemicals with Signaling, Medicinal and Therapeutic Properties)
253 KiB  
Article
Composition of Sulla (Hedysarum coronarium L.) Honey Solvent Extractives Determined by GC/MS: Norisoprenoids and Other Volatile Organic Compounds
by Igor Jerković, Carlo I.G. Tuberso, Mirko Gugić and Dragan Bubalo
Molecules 2010, 15(9), 6375-6385; https://doi.org/10.3390/molecules15096375 - 9 Sep 2010
Cited by 31 | Viewed by 11767 | Correction
Abstract
Samples of unifloral sulla (Hedysarum coronarum L.) honey from Sardinia (Italy) were analysed. To investigate the chemical composition of the honey volatiles two solvent systems were used for ultrasonic solvent extraction (USE): 1) a 1:2 (v/v) pentane and diethyl ether mixture and [...] Read more.
Samples of unifloral sulla (Hedysarum coronarum L.) honey from Sardinia (Italy) were analysed. To investigate the chemical composition of the honey volatiles two solvent systems were used for ultrasonic solvent extraction (USE): 1) a 1:2 (v/v) pentane and diethyl ether mixture and 2) dichloromethane. All the extracts were analysed by GC and GC/MS. These procedures have permitted the identification of 56 compounds that include norisoprenoids, benzene derivatives, aliphatic compounds and Maillard reaction products. Norisoprenoids were the major compounds in both extracts, dominated by vomifoliol (5.3-11.2%; 9.6-14.0%) followed by minor percentages of other norisoprenoids such as α-isophorone, 4-ketoisophorone, 3-oxo-α-ionol or 3-oxo-α-ionone. Other abundant single compounds in the extracts were 3-hydroxy-4-phenylbutan-2-one (0.8-5.4%; 0.6-5.7%) and methyl syringate (3.0-5.7%; 2.2-4.1%). The composition of the volatiles and semi-volatiles in the obtained extracts suggests that sulla honey is quite distinctive relative to the other honeys that have been chemically studied by GC/MS, but no specific markers of the honey botanical origin were found. Full article
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196 KiB  
Article
Bio-guided Isolation of Antioxidant Compounds from Chrysophyllum perpulchrum, a Plant Used in the Ivory Coast Pharmacopeia
by Bidie Alain Philippe, Ndjoko Karine, Attioua Koffi Barthélemy, Zirihi Guédé Noél, N’guessan Jean David, Djaman Allico Joseph and Kurt Hosttetmann
Molecules 2010, 15(9), 6386-6398; https://doi.org/10.3390/molecules15096386 - 13 Sep 2010
Cited by 15 | Viewed by 9113
Abstract
Chrysophyllum perpulchrum (Sapotaceae) is used in the traditional Ivory Coast pharmacopeia to cure fevers. The extract of C. perpulchrum used for this study was the powdered form obtained from the maceration of the dried plant bark in 96% methanol, followed by evaporation to [...] Read more.
Chrysophyllum perpulchrum (Sapotaceae) is used in the traditional Ivory Coast pharmacopeia to cure fevers. The extract of C. perpulchrum used for this study was the powdered form obtained from the maceration of the dried plant bark in 96% methanol, followed by evaporation to dryness. In the present study, the antioxidative and radical-scavenging activities of the methanolic extract were studied with three standard biological tests: DPPH reduction, ferric thiocyanate (FTC) lipidic peroxidation inhibition and thiobarbituric acid reacting substances (TBARS). Gallic acid and quercetin were used as references. The total amount of phenolic compounds in the extract was determined by ultraviolet (UV) spectrometry and calculated as gallic acid equivalents. Catechin and two dimeric procyanidins were found to be the compounds responsible for the activities. They were chemically dereplicated in the extract by LC-MS. For quantitation purposes, they were isolated by successive chromatographic methods and characterized by mass spectrometry (MS) and nuclear magnetic resonance (NMR) spectrometry. The quantities of these compounds in C. perpulchrum were 5.4% for catechin (P1), and 5.6 and 9.2% for dimers (compounds 2 (P2) and 3 (P3)), respectively. They displayed antioxidant activity with IC50 values of 2.50 ± 0.15 µg/mL (P1), 2.10 ± 0.2 µg/mL (P2) and 2.10 ± 0.1 µg/mL (P3). The total extract, the active fractions and the pure compounds inhibited the lipid peroxidation by the FTC method and the TBARS method in the range of 60%. These values were comparable to those seen for quercetin. Full article
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282 KiB  
Article
Solid-Phase Synthesis and Evaluation of Glycopeptide Fragments from Rat Epididymal Cysteine-Rich Secretory Protein-1 (Crisp-1)
by Mian Liu, David W. Hamilton and George Barany
Molecules 2010, 15(9), 6399-6410; https://doi.org/10.3390/molecules15096399 - 14 Sep 2010
Cited by 2 | Viewed by 10222
Abstract
Three 18-residue peptides with the sequence Glp-Asp-Thr-Thr-Asp-Glu-Trp-Asp-Arg-Asp-Leu-Glu-Asn-Leu-Ser-Thr-Thr-Lys, taken from the N-terminus of the rat epididymal cysteine-rich secretory protein (Crisp-1) that is important in the fertilization process, were prepared by Fmoc solid-phase synthesis using a convergent strategy. These [...] Read more.
Three 18-residue peptides with the sequence Glp-Asp-Thr-Thr-Asp-Glu-Trp-Asp-Arg-Asp-Leu-Glu-Asn-Leu-Ser-Thr-Thr-Lys, taken from the N-terminus of the rat epididymal cysteine-rich secretory protein (Crisp-1) that is important in the fertilization process, were prepared by Fmoc solid-phase synthesis using a convergent strategy. These peptides were the parent sequence, plus two possible α-O-linked TN antigen-containing glycopeptides with a Thr(α-D-GalNAc) residue in place of either Thr3 or Thr4. During chain assembly, two deletion peptides [des-Asp2 and des-Thr(Ac3-α-D-GalNAc)] and one terminated peptide [N-acetylated 14-mer] arose, as did several peptides in which aspartimide formation had occurred at each of the four possible positions in the sequence. These by-products totaled ~20% of the desired product; they were recognized by HPLC and ESI-MS and removed during the intermediate purifications. Final products, obtained in 15-21% overall yields, were characterized by HPLC purities and ESI-MS. Circular dichroism (CD) spectra for all three purified peptides, recorded in pure water and in trifluoroethanol-H2O (1:1), revealed that the presence of a sugar moiety does not significantly impact the sampled conformations. Future biological evaluation could elucidate the nature and locus of sugar modification of Crisp-1, and provide insight as to why Crisp-1 protein E binds sperm irreversibly, in contrast to protein D that lacks a sugar near the N-terminus and only binds sperm loosely. Full article
(This article belongs to the Special Issue Solid Phase Synthesis)
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180 KiB  
Article
Chemical Analysis and Biological Activity of the Essential Oils of Two Valerianaceous Species from China: Nardostachys chinensis and Valeriana officinalis
by Jihua Wang, Jianglin Zhao, Hao Liu, Ligang Zhou, Zhilong Liu, Jingguo Wang, Jianguo Han, Zhu Yu and Fuyu Yang
Molecules 2010, 15(9), 6411-6422; https://doi.org/10.3390/molecules15096411 - 14 Sep 2010
Cited by 92 | Viewed by 11974
Abstract
In order to investigate essential oils with biological activity from local wild plants, two valerianaceous species, Nardostachys chinensis and Valeriana officinalis, were screened for their antimicrobial and antioxidant activity. The essential oils were obtained from the roots and rhizomes of the two [...] Read more.
In order to investigate essential oils with biological activity from local wild plants, two valerianaceous species, Nardostachys chinensis and Valeriana officinalis, were screened for their antimicrobial and antioxidant activity. The essential oils were obtained from the roots and rhizomes of the two plants by hydro-distillation, and were analyzed for their chemical composition by gas chromatography (GC) and gas chromatography-mass spectrometry (GC-MS). Calarene (25.31%), aristolone (13.35%), α-selinene (7.32%) and β-maaliene (6.70%) were the major compounds of the 23 identified components which accounted for 92.76% of the total oil of N. chinensis. Patchoulol (16.75%), α-pinene (14.81%), and β-humulene (8.19%) were the major compounds among the 20 identified components, which accounted for 88.11% of the total oil of V. officinalis. Both oils were rich in sesquiterpene hydrocarbons as well as their oxygenated derivatives. Essential oils were shown to have broad spectrum antibacterial activity with MIC values that ranged from 62.5 μg/mL to 400 μg/mL, and IC50 values from 36.93 μg/mL to 374.72 μg/mL. The oils were also shown to have moderate antifungal activity to Candida albicans growth as well as inhibition of spore germination of Magnaporthe oryzae. Two essential oils were assessed by 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical scavenging, β-carotene bleaching and ferrozine-ferrous ions assays, respectively, to show moderate antioxidant activity. Results suggest that the isolated essential oils could be used for future development of antimicrobial and antioxidant agents. Full article
1157 KiB  
Article
Inhibitory Effect of Indigo Naturalis on Tumor Necrosis Factor-α-Induced Vascular Cell Adhesion Molecule-1 Expression in Human Umbilical Vein Endothelial Cells
by Hsin-Ning Chang, Jong-Hwei Su Pang, Sien-Hung Yang, Chi-Feng Hung, Chi-Hsin Chiang, Tung-Yi Lin and Yin-Ku Lin
Molecules 2010, 15(9), 6423-6435; https://doi.org/10.3390/molecules15096423 - 14 Sep 2010
Cited by 25 | Viewed by 10048
Abstract
The use of indigo naturalis to treat psoriasis has proved effective in our previous clinical studies. The present study was designed to examine the anti-inflammatory effect of indigo naturalis in primary cultured human umbilical vein endothelial cells (HUVECs). Pretreatment of cells with indigo [...] Read more.
The use of indigo naturalis to treat psoriasis has proved effective in our previous clinical studies. The present study was designed to examine the anti-inflammatory effect of indigo naturalis in primary cultured human umbilical vein endothelial cells (HUVECs). Pretreatment of cells with indigo naturalis extract attenuated TNF-α-induced increase in Jurkat T cell adhesion to HUVECs as well as decreased the protein and messenger (m)RNA expression levels of vascular cell adhesion molecule-1 (VCAM-1) on HUVECs. Indigo naturalis extract also inhibited the protein expression of activator protein-1 (AP-1)/c-Jun, a critical transcription factor for the activation of VCAM-1 gene expression. Since the reduction of lymphocyte adhesion to vascular cells by indigo naturalis extract could subsequently reduce the inflammatory reactions caused by lymphocyte infiltration in the epidermal layer and help to improve psoriasis, this study provides a potential mechanism for the anti-inflammatory therapeutic effect of indigo naturalis extract in psoriasis. Full article
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733 KiB  
Article
Anti-Inflammatory Activity of Chrysophanol through the Suppression of NF-kB/Caspase-1 Activation in Vitro and in Vivo
by Su-Jin Kim, Min-Cheol Kim, Byong-Joo Lee, Dae-Hee Park, Seung-Heon Hong and Jae-Young Um
Molecules 2010, 15(9), 6436-6451; https://doi.org/10.3390/molecules15096436 - 16 Sep 2010
Cited by 115 | Viewed by 13628
Abstract
Chrysophanol is a member of the anthraquinone family and has multiple pharmacological effects, but the exact mechanism of the anti-inflammatory effects of chrysophanol has yet to be thoroughly elucidated. In this study, we attempted to determine the effects of chrysophanol on dextran sulfate [...] Read more.
Chrysophanol is a member of the anthraquinone family and has multiple pharmacological effects, but the exact mechanism of the anti-inflammatory effects of chrysophanol has yet to be thoroughly elucidated. In this study, we attempted to determine the effects of chrysophanol on dextran sulfate sodium (DSS)-induced colitis and lipopolysaccharide (LPS)-induced inflammatory responses in mouse peritoneal macrophages. The findings of this study demonstrated that chrysophanol effectively attenuated overall clinical scores as well as various pathological markers of colitis. Additionally, chrysophanol inhibited the production of tumor necrosis factor (TNF)-a, interleukin (IL)-6 and the expression of cyclooxygenase (COX)-2 levels induced by LPS. We showed that this anti-inflammatory effect of chrysophanol is through suppression of the activation of NF-kB and caspase-1 in LPS-stimulated macrophages. These results provide novel insights into the pharmacological actions of chrysophanol as a potential molecule for use in the treatment of inflammatory diseases. Full article
(This article belongs to the Section Natural Products Chemistry)
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357 KiB  
Article
Effects of Eupatilin and Jaceosidin on Cytochrome P450 Enzyme Activities in Human Liver Microsomes
by Hye Young Ji, Sung Yeon Kim, Dong Kyun Kim, Ji Hyun Jeong and Hye Suk Lee
Molecules 2010, 15(9), 6466-6475; https://doi.org/10.3390/molecules15096466 - 16 Sep 2010
Cited by 33 | Viewed by 11359
Abstract
Eupatilin and jaceosidin are bioactive flavones found in the medicinal herbs of the genus Artemisia. These bioactive flavones exhibit various antioxidant, antiinflammatory, antiallergic, and antitumor activities. The inhibitory potentials of eupatilin and jaceosidin on the activities of seven major human cytochrome P450 [...] Read more.
Eupatilin and jaceosidin are bioactive flavones found in the medicinal herbs of the genus Artemisia. These bioactive flavones exhibit various antioxidant, antiinflammatory, antiallergic, and antitumor activities. The inhibitory potentials of eupatilin and jaceosidin on the activities of seven major human cytochrome P450 enzymes in human liver microsomes were investigated using a cocktail probe assay. Eupatilin and jaceosidin potently inhibited CYP1A2-catalyzed phenacetin O-deethylation with 50% inhibitory concentration (IC50) values of 9.4 mM and 5.3 mM, respectively, and CYP2C9-catalyzed diclofenac 4-hydroxylation with IC50 values of 4.1 mM and 10.2 mM, respectively. Eupatilin and jaceosidin were also found to moderately inhibit CYP2C19-catalyzed [S]-mephenytoin 4¢-hydroxylation, CYP2D6-catalyzed bufuralol 1¢-hydroxylation, and CYP2C8-catalyzed amodiaquine N-deethylation. Kinetic analysis of human liver microsomes showed that eupatilin is a competitive inhibitor of CYP1A2 with a Ki value of 2.3 mM and a mixed-type inhibitor of CYP2C9 with a Ki value of 1.6 mM. Jaceosidin was shown to be a competitive inhibitor of CYP1A2 with a Ki value of 3.8 mM and a mixed-type inhibitor of CYP2C9 with Ki value of 6.4 mM in human liver microsomes. These in vitro results suggest that eupatilin and jaceosidin should be further examined for potential pharmacokinetic drug interactions in vivo due to inhibition of CYP1A2 and CYP2C9. Full article
(This article belongs to the Collection Bioactive Compounds)
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Communication
Isoquinolines from the Roots of Thalictrum flavum L. and Their Evaluation as Antiparasitic Compounds
by Jacqueline Ropivia, Séverine Derbré, Caroline Rouger, Fabrice Pagniez, Patrice Le Pape and Pascal Richomme
Molecules 2010, 15(9), 6476-6484; https://doi.org/10.3390/molecules15096476 - 16 Sep 2010
Cited by 22 | Viewed by 16075
Abstract
Alkaloids from Thalictrum flavum L. (Ranuculaceae) growing in the Loire valley (France) were isolated and evaluated for their antiplasmodial and leishmanicidal activities. Berberine was identified as a major component but its analogue, pseudoberberine, was isolated for the first time from this plant. As [...] Read more.
Alkaloids from Thalictrum flavum L. (Ranuculaceae) growing in the Loire valley (France) were isolated and evaluated for their antiplasmodial and leishmanicidal activities. Berberine was identified as a major component but its analogue, pseudoberberine, was isolated for the first time from this plant. As far as bisbenzylisoquinolines are concerned, thalfoetidine was also isolated and, besides, its nor- derivative, northalfoetidine, was identified as a new compound. Previously isolated alkaloids from Thalictrum species such as northalidasine, northalrugosidine, thaligosidine, thalicberine, thaliglucinone, preocoteine, O-methylcassythine and armepavine were newly described in the roots of T. flavum. Tertiary isoquinolines, and particularly bisbenzylisoquinolines, were found to be leishmanicidal against L. major. Thalfoetidine appeared as the most potent but its new nor- derivative northalfoetidine, as well as northalidasine, were of particular interest due to the fact that their potential leishmanicidal activity was not associated to a strong cytotoxicity. Full article
(This article belongs to the Section Natural Products Chemistry)
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269 KiB  
Communication
Synthesis and Antifungal Activity of Carabrone Derivatives
by Jun-Tao Feng, Zhi-Qing Ma, Jiang-Hua Li, Jun He, Hui Xu and Xing Zhang
Molecules 2010, 15(9), 6485-6492; https://doi.org/10.3390/molecules15096485 - 16 Sep 2010
Cited by 22 | Viewed by 6737
Abstract
Nine derivatives 6-14 of carabrone (1) were synthesized and tested in vitro against Colletotrichum lagenarium Ell et Halst using the spore germination method. Among all of the derivatives, compounds 6-8 and 12 showed more potent antifungal activity than [...] Read more.
Nine derivatives 6-14 of carabrone (1) were synthesized and tested in vitro against Colletotrichum lagenarium Ell et Halst using the spore germination method. Among all of the derivatives, compounds 6-8 and 12 showed more potent antifungal activity than 1. Structure-activity relationships (SAR) demonstrated that the γ-lactone was necessary for the antifungal activity of 1, and the substituents on the C-4 position of 1 could significantly affect the antifungal activity. Full article
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184 KiB  
Article
An Efficient and Chemoselective Procedure for Acylal Synthesis
by Da-He Fan, Hui Wang, Xing-Xing Mao and Yong-Miao Shen
Molecules 2010, 15(9), 6493-6501; https://doi.org/10.3390/molecules15096493 - 16 Sep 2010
Cited by 8 | Viewed by 10456
Abstract
A novel heterogeneous efficient procedure has been developed for the chemoselective synthesis of acylals (1,1-diacetates) under solvent-free conditions. A novel catalyst prepared by the sulfuric acid catalyzed copolymerization of p-toluenesulfonic acid and paraformaldehyde displays extremely high activities for the title reactions, affording [...] Read more.
A novel heterogeneous efficient procedure has been developed for the chemoselective synthesis of acylals (1,1-diacetates) under solvent-free conditions. A novel catalyst prepared by the sulfuric acid catalyzed copolymerization of p-toluenesulfonic acid and paraformaldehyde displays extremely high activities for the title reactions, affording average yields over 90% within several minutes. A comparative study showed that the novel catalyst has much higher activity than other catalysts used for this purpose. Besides, the novel catalyst displays chemoselectivity for the protection of aldehydes in the presence of ketones. In addition the high acidity (4.0 mmol/g), thermal stability (200 ºC) and easy reusability make the novel catalyst one of the best choices for the process. Full article
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Article
Synthesis and Antitumor Activity of Diterpenylhydroquinone Derivatives of Natural Ent-Labdanes
by Luis Espinoza Catalán, Evelyn Baeza Maturana, Karen Catalán Marín, Mauricio Osorio Olivares, Héctor Carrasco Altamirano, Mauricio Cuellar Fritis and Joan Villena García
Molecules 2010, 15(9), 6502-6511; https://doi.org/10.3390/molecules15096502 - 17 Sep 2010
Cited by 12 | Viewed by 8867
Abstract
Two new compounds 2β-acetoxy-15-phenyl-(22,25-acetoxy)-ent-labda-8(17), 13(E)-diene (9) and 2β-hydroxy-15-phenyl-(22,24,26-trimethoxy)-ent-labda-8(17),13(E)-diene (10) have been prepared by an Electrophilic Aromatic Substitution (EAS) reaction between diterpenyl allylic alcohols and 1,4-hydroquinone or 1,3,5-trimethoxybenzene using BF [...] Read more.
Two new compounds 2β-acetoxy-15-phenyl-(22,25-acetoxy)-ent-labda-8(17), 13(E)-diene (9) and 2β-hydroxy-15-phenyl-(22,24,26-trimethoxy)-ent-labda-8(17),13(E)-diene (10) have been prepared by an Electrophilic Aromatic Substitution (EAS) reaction between diterpenyl allylic alcohols and 1,4-hydroquinone or 1,3,5-trimethoxybenzene using BF3.Et2O as a catalyst. These compounds, along with a series of natural ent-labdanes 3-8, have been evaluated for their in vitro cytotoxic activities against cultured human cancer cells of PC-3 and DU-145 human prostate cancer, MCF-7 and MDA-MB-231 breast carcinoma and dermal human fibroblasts (DHF). Some compounds displayed inhibition at µM IC50 values. Full article
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276 KiB  
Article
New 2-Arylbenzofurans from the Root Bark of Artocarpus lakoocha
by Boonchoo Sritularak, Kullasap Tantrakarnsakul, Kittisak Likhitwitayawuid and Vimolmas Lipipun
Molecules 2010, 15(9), 6548-6558; https://doi.org/10.3390/molecules15096548 - 17 Sep 2010
Cited by 15 | Viewed by 5812
Abstract
Three new prenylated 2-arylbenzofurans – artolakoochol, 4-hydroxy-artolakoochol and cycloartolakoochol – have been isolated from the root bark of Artocarpus lakoocha Roxb., Their structures were elucidated through analysis of their spectroscopic data, and their antiherpetic potential was evaluated by the plaque reduction assay. Full article
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Article
Correlation between Cytotoxic Activities and Reduction Potentials of Heterocyclic Quinones
by Junko Koyama, Izumi Morita and Takao Yamori
Molecules 2010, 15(9), 6559-6569; https://doi.org/10.3390/molecules15096559 - 20 Sep 2010
Cited by 18 | Viewed by 7741
Abstract
To search for possible anti-tumor agents or anti-tumor promoters among natural or synthetic products, we used cyclic voltammetry to determine the reduction-oxidation potentials of heterocyclic quinones in phosphate buffer at pH 7.2. We determined the growth inhibitory- and cytotoxic activities of 12 heterocyclic [...] Read more.
To search for possible anti-tumor agents or anti-tumor promoters among natural or synthetic products, we used cyclic voltammetry to determine the reduction-oxidation potentials of heterocyclic quinones in phosphate buffer at pH 7.2. We determined the growth inhibitory- and cytotoxic activities of 12 heterocyclic quinone anti-tumor agent candidates against a panel of 39 human cancer cell lines (JFCR39). The average concentrations of the heterocyclic quinones required for 50% growth inhibition (GI50) against JFCR39 ranged from 0.045 to 13.2 µM, and the 50% lethal concentration (LC50) against JFCR39 ranged from 0.398 to 77.7 µM. The average values of GI50 or LC50 of the heterocyclic quinones correlated significantly with their reduction potentials. These results suggested that reduction-oxidation potentials could be a useful method for the discovery of novel antitumor agents. Full article
(This article belongs to the Collection Bioactive Compounds)
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Article
Determination of Quercetin and Resveratrol in Whole Blood—Implications for Bioavailability Studies
by Lucia Biasutto, Ester Marotta, Spiridione Garbisa, Mario Zoratti and Cristina Paradisi
Molecules 2010, 15(9), 6570-6579; https://doi.org/10.3390/molecules15096570 - 20 Sep 2010
Cited by 66 | Viewed by 12825
Abstract
Resveratrol (trans-3,4',5-trihydroxystilbene) and quercetin (3,3’,4’,5,7-pentahydroxyflavone) are two naturally occurring polyphenols with the potential to exert beneficial health effects. Since their low bioavailability is a major obstacle to biomedical applications, efforts are being made to improve their absorption and slow down phase [...] Read more.
Resveratrol (trans-3,4',5-trihydroxystilbene) and quercetin (3,3’,4’,5,7-pentahydroxyflavone) are two naturally occurring polyphenols with the potential to exert beneficial health effects. Since their low bioavailability is a major obstacle to biomedical applications, efforts are being made to improve their absorption and slow down phase II metabolism. An accurate evaluation of the corresponding levels in the bloodstream is important to assess delivery strategies, as well as to verify claims of efficacy based on in vitro results. In the present work we have optimized a simple method ensuring complete stabilization and extraction of resveratrol and quercetin from whole blood. The suitability of different protocols was evaluated by measuring the recovery of polyphenol and internal standard from spiked blood samples via HPLC/UV analysis. The optimized procedure ensured a satisfactory recovery of both internal standards and compounds. Comparing plasma and whole blood, up to 76% of the analyte, being associated with the cellular fraction, was unaccounted for when examining only plasma. This indicates the importance of analysing whole blood rather than plasma to avoid underestimating polyphenol absorption in bioavailability studies. Full article
(This article belongs to the Special Issue Phenolics and Polyphenolics)
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Communication
Variation of Oleanolic and Ursolic Acid in the Flesh of Persimmon Fruit among Different Cultivars
by Chunhua Zhou, Yanle Sheng, Daqiu Zhao, Zhiqin Wang and Jun Tao
Molecules 2010, 15(9), 6580-6587; https://doi.org/10.3390/molecules15096580 - 20 Sep 2010
Cited by 35 | Viewed by 8937
Abstract
Oleanolic acid (OA) and ursolic acid (UA) are important bioactive components in many plants, including persimmon (Diospyros kaki L.). The present work was carried out to determine OA and UA contents in the flesh of persimmon fruit from 32 cultivars, including 23 astringent [...] Read more.
Oleanolic acid (OA) and ursolic acid (UA) are important bioactive components in many plants, including persimmon (Diospyros kaki L.). The present work was carried out to determine OA and UA contents in the flesh of persimmon fruit from 32 cultivars, including 23 astringent and 9 non-astringent ones, by applying high performance liquid chromatography (HPLC) with UV detection. Both OA and UA were present in all of the investigated cultivars, except for three, ‘Hiratanenashi’, ‘Ribenhongshi’ and ‘Matsumotowase’. The OA content ranged from traces to 88.57 μg/g FW, and that of UA were between traces and 27.64 μg/g FW. Full article
(This article belongs to the Section Natural Products Chemistry)
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Article
Synthesis of Chiral Macrocyclic or Linear Pyridine Carboxamides from Pyridine-2,6-dicarbonyl Dichloride as Antimicrobial Agents
by Rashad A. Al-Salahi, Mohamed A Al-Omar and Abd El-Galil E Amr
Molecules 2010, 15(9), 6588-6597; https://doi.org/10.3390/molecules15096588 - 20 Sep 2010
Cited by 55 | Viewed by 10450
Abstract
A series of chiral linear and macrocyclic bridged pyridines has been prepared starting from pyridine-2,6-dicarbonyl dichloride (2). The coupling of 1 with D-alanyl methyl ester gave 2,6-bis-D-alanyl pyridine methyl ester (3). Hydrazinolysis of 3 with hydrazine hydrate afforded bis-hydrazide 4. The latter was [...] Read more.
A series of chiral linear and macrocyclic bridged pyridines has been prepared starting from pyridine-2,6-dicarbonyl dichloride (2). The coupling of 1 with D-alanyl methyl ester gave 2,6-bis-D-alanyl pyridine methyl ester (3). Hydrazinolysis of 3 with hydrazine hydrate afforded bis-hydrazide 4. The latter was reacted with thiophene-2-carbaldehyde, phthalic anhydride or cyclohexanone to afford bis-carboxamide pyridine derivatives 5-7, respectively. Compound 4 was coupled with p-methoxy- or p-nitroaceto-phenone to yield compounds 8 and 9. In addition, 4 was reacted with 1,2,4,5-benzenetetra-carboxylic acid dianhydride or 1,4,5,8-naphthalenetetracarboxylic acid dianhydride to afford the macrocyclic octacarboxaamide pyridines 10 and 11. The detailed synthesis, spectroscopic data and antimicrobial screening for the synthesized compounds are reported. Full article
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Article
Green One Pot Solvent-Free Synthesis of Pyrano[2,3-c]-Pyrazoles and Pyrazolo[1,5-a]Pyrimidines
by Hamad M. Al-Matar, Khaled D. Khalil, Aisha Y. Adam and Mohamed H. Elnagdi
Molecules 2010, 15(9), 6619-6629; https://doi.org/10.3390/molecules15096619 - 20 Sep 2010
Cited by 92 | Viewed by 13824
Abstract
Pyrano[2,3-c]pyrazoles are obtained via mixing ethyl acetoacetate, hydrazine hydrate, aldehydes or ketones and malononitrile in the absence of solvent. These same products were also obtained by reacting arylidenemalononitriles 3 with 3-methyl-2-pyrazolin-5-ones. NOE difference experiments confirmed that these products exist solely in [...] Read more.
Pyrano[2,3-c]pyrazoles are obtained via mixing ethyl acetoacetate, hydrazine hydrate, aldehydes or ketones and malononitrile in the absence of solvent. These same products were also obtained by reacting arylidenemalononitriles 3 with 3-methyl-2-pyrazolin-5-ones. NOE difference experiments confirmed that these products exist solely in the 2H form. Similar treatments of 3-amino-2-pyrazolin-5-one with arylidene-malononitrile afforded adduct 6. Similarly mixing ethyl cyanoacetate, hydrazine hydrate, aldehydes, with malononitrile gave the same product 6. A novel synthesis of 4-oxo-4H-pyrano[2,3-c]pyrazole (8) could be achieved via reacting 3-methyl-2-pyrazolin-5-one with a mixture of cyanoacetic acid and acetic anhydride. Similar treatment of 3-aminopyrazole 11 with the benzylidene-malononitrile produced the pyrazolo[2,3-a]pyrimidines 12a,b. Full article
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Article
The Antigerminative Activity of Twenty-Seven Monoterpenes
by Laura De Martino, Emilia Mancini, Luiz Fernando Rolim de Almeida and Vincenzo De Feo
Molecules 2010, 15(9), 6630-6637; https://doi.org/10.3390/molecules15096630 - 21 Sep 2010
Cited by 170 | Viewed by 13990
Abstract
Monoterpenes, the main constituents of essential oils, are known for their many biological activities. The present work studied the potential biological activity of twenty-seven monoterpenes, including monoterpene hydrocarbons and oxygenated ones, against seed germination and subsequent primary radicle growth of Raphanus sativus L. [...] Read more.
Monoterpenes, the main constituents of essential oils, are known for their many biological activities. The present work studied the potential biological activity of twenty-seven monoterpenes, including monoterpene hydrocarbons and oxygenated ones, against seed germination and subsequent primary radicle growth of Raphanus sativus L. (radish) and Lepidium sativum L. (garden cress), under laboratory conditions. The compounds, belonging to different chemical classes, showed different potency in affecting both parameters evaluated. The assayed compounds demonstrated a good inhibitory activity in a dose-dependent way. In general, radish seed is more sensitive than garden cress and its germination appeares more inhibited by alcohols; at the highest concentration tested, the more active substances were geraniol, borneol, (±)-β-citronellol and α-terpineol. Geraniol and carvone inhibited, in a significant way, the germination of garden cress, at the highest concentration tested. Radicle elongation of two test species was inhibited mainly by alcohols and ketones. Carvone inhibited the radicle elongation of both seeds, at almost all concentrations assayed, while 1,8-cineole inhibited their radicle elongation at the lowest concentrations (10−5 M, 10−6 M). Full article
(This article belongs to the Section Natural Products Chemistry)

Review

Jump to: Research

541 KiB  
Review
Generation and Development of RNA Ligase Ribozymes with Modular Architecture Through “Design and Selection”
by Yuki Fujita, Junya Ishikawa, Hiroyuki Furuta and Yoshiya Ikawa
Molecules 2010, 15(9), 5850-5865; https://doi.org/10.3390/molecules15095850 - 26 Aug 2010
Cited by 8 | Viewed by 9115
Abstract
In vitro selection with long random RNA libraries has been used as a powerful method to generate novel functional RNAs, although it often requires laborious structural analysis of isolated RNA molecules. Rational RNA design is an attractive alternative to avoid this laborious step, [...] Read more.
In vitro selection with long random RNA libraries has been used as a powerful method to generate novel functional RNAs, although it often requires laborious structural analysis of isolated RNA molecules. Rational RNA design is an attractive alternative to avoid this laborious step, but rational design of catalytic modules is still a challenging task. A hybrid strategy of in vitro selection and rational design has been proposed. With this strategy termed “design and selection,” new ribozymes can be generated through installation of catalytic modules onto RNA scaffolds with defined 3D structures. This approach, the concept of which was inspired by the modular architecture of naturally occurring ribozymes, allows prediction of the overall architectures of the resulting ribozymes, and the structural modularity of the resulting ribozymes allows modification of their structures and functions. In this review, we summarize the design, generation, properties, and engineering of four classes of ligase ribozyme generated by design and selection. Full article
(This article belongs to the Special Issue Catalytic Nucleic Acids)
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642 KiB  
Review
Discovery and Development of Anti-HBV Agents and Their Resistance
by Kyun-Hwan Kim, Nam Doo Kim and Baik-Lin Seong
Molecules 2010, 15(9), 5878-5908; https://doi.org/10.3390/molecules15095878 - 27 Aug 2010
Cited by 57 | Viewed by 11963
Abstract
Hepatitis B virus (HBV) infection is a prime cause of liver diseases such as hepatitis, cirrhosis and hepatocellular carcinoma. The current drugs clinically available are nucleot(s)ide analogues that inhibit viral reverse transcriptase activity. Most drugs of this class are reported to have viral [...] Read more.
Hepatitis B virus (HBV) infection is a prime cause of liver diseases such as hepatitis, cirrhosis and hepatocellular carcinoma. The current drugs clinically available are nucleot(s)ide analogues that inhibit viral reverse transcriptase activity. Most drugs of this class are reported to have viral resistance with breakthrough. Recent advances in methods for in silico virtual screening of chemical libraries, together with a better understanding of the resistance mechanisms of existing drugs have expedited the discovery and development of novel anti-viral drugs. This review summarizes the current status of knowledge about and viral resistance of HBV drugs, approaches for the development of novel drugs as well as new viral and host targets for future drugs. Full article
(This article belongs to the Special Issue Anti-Infective Agents)
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1229 KiB  
Review
Neuroscientists as Cartographers: Mapping the Crossroads of Gonadal Hormones, Memory and Age Using Animal Models
by Heather A. Bimonte-Nelson, Jazmin I. Acosta and Joshua S. Talboom
Molecules 2010, 15(9), 6050-6105; https://doi.org/10.3390/molecules15096050 - 31 Aug 2010
Cited by 38 | Viewed by 12370
Abstract
Cognitive function is multidimensional and complex, and research in multiple species indicates it is considerably impacted by age and gonadal hormone milieu. One domain of cognitive function particularly susceptible to age-related decrements is spatial memory. Gonadal hormones can alter spatial memory, and they [...] Read more.
Cognitive function is multidimensional and complex, and research in multiple species indicates it is considerably impacted by age and gonadal hormone milieu. One domain of cognitive function particularly susceptible to age-related decrements is spatial memory. Gonadal hormones can alter spatial memory, and they are potent modulators of brain microstructure and function in many of the same brain areas affected by aging. In this paper, we review decades of animal and human literature to support a tertiary model representing interactions between gonadal hormones, spatial cognition and age given that: 1) gonadal hormones change with age, 2) age impacts spatial learning and memory, and 3) gonadal hormones impact spatial learning and memory. While much has been discovered regarding these individual tenets, the compass for future aging research points toward clarifying the interactions that exist between these three points, and understanding mediating variables. Indeed, identifying and aligning the various components of the complex interactions between these tenets, including evaluations using basic science, systems, and clinical perspectives, is the optimal approach to attempt to converge the many findings that may currently appear contradictory. In fact, as discoveries are being made it is becoming clear that the findings across studies that appear contradictory are not contradictory at all. Rather, there are mediating variables that are influencing outcome and affecting the extent, and even the direction, of the effects that gonadal hormones have on cognition during aging. These mediating variables are just starting to be understood. By aligning basic scientific discoveries with clinical interpretations, we can maximize the opportunities for discoveries and subsequent interventions to allow individuals to “optimize their aging” and find their own map to cognitive health as aging ensues. Full article
(This article belongs to the Special Issue Neuroprotective Strategies)
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Review
A Therapeutic Approach to Nasopharyngeal Carcinomas by DNAzymes Targeting EBV LMP-1 Gene
by Lifang Yang, Zhongxin Lu, Xiaoqian Ma, Ya Cao and Lun-Quan Sun
Molecules 2010, 15(9), 6127-6139; https://doi.org/10.3390/molecules15096127 - 1 Sep 2010
Cited by 38 | Viewed by 9969
Abstract
Epstein-Barr virus (EBV)-encoded latent membrane protein 1 (LMP1) has been known to have oncogenic properties during latent infection in nasopharyngeal carcinoma (NPC). Genetic manipulation of LMP1 expression may provide a novel strategy for the treatment of NPC. DNAzymes are synthetic, single-stranded DNA catalysts [...] Read more.
Epstein-Barr virus (EBV)-encoded latent membrane protein 1 (LMP1) has been known to have oncogenic properties during latent infection in nasopharyngeal carcinoma (NPC). Genetic manipulation of LMP1 expression may provide a novel strategy for the treatment of NPC. DNAzymes are synthetic, single-stranded DNA catalysts that can be engineered to bind and cleave the target mRNA of a disease-causing gene. By targeting the LMP1 mRNA, we successfully obtained a phosphorothioate-modified ‘‘10–23’’ DNAzyme namely DZ1, through screening a series of DNAzymes. DZ1 could significantly down-regulate the expression of LMP1 in NPC cells, inhibit cell proliferation, metastasis, promote apoptosis and enhance radiosensitivity of NPC through interfering signal pathways which are abnormally activated by LMP1, including NF-κB, AP-1 and STAT3 signal pathways. Together, interfering LMP1 signaling pathway could be a promising strategy to target the malignant phenotypes of NPC. Full article
(This article belongs to the Special Issue Catalytic Nucleic Acids)
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1373 KiB  
Review
The Structural Diversity of Deoxyribozymes
by Simon A. McManus and Yingfu Li
Molecules 2010, 15(9), 6269-6284; https://doi.org/10.3390/molecules15096269 - 6 Sep 2010
Cited by 18 | Viewed by 10889
Abstract
When not constrained to long double-helical arrangements, DNA is capable of forming structural arrangements that enable specific sequences to perform functions such as binding and catalysis under defined conditions. Through a process called in vitro selection, numerous catalytic DNAs, known as deoxyribozymes or [...] Read more.
When not constrained to long double-helical arrangements, DNA is capable of forming structural arrangements that enable specific sequences to perform functions such as binding and catalysis under defined conditions. Through a process called in vitro selection, numerous catalytic DNAs, known as deoxyribozymes or DNAzymes, have been isolated. Many of these molecules have the potential to act as therapeutic agents and diagnostic tools. As such, a better understanding of the structural arrangements present in these functional DNAs will aid further efforts in the development and optimization of these useful molecules. Structural characterization of several deoxyribozymes through mutagenesis, in vitro re-selection, chemical probing and circular dichroism has revealed many distinct and elaborate structural classes. Deoxyribozymes have been found to contain diverse structural elements including helical junctions, pseudoknots, triplexes, and guanine quadruplexes. Some of these studies have further shown the repeated isolation of similar structural motifs in independent selection experiments for the same type of chemical reaction, suggesting that some structural motifs are well suited for catalyzing a specific chemical reaction. To investigate the extent of structural diversity possible in deoxyribozymes, a group of kinase deoxyribozymes have been extensively characterized. Such studies have discovered some interesting structural features of these DNAzymes while revealing some novel DNA structures. Full article
(This article belongs to the Special Issue Catalytic Nucleic Acids)
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227 KiB  
Review
Recent Applications of Polymer Supported Organometallic Catalysts in Organic Synthesis
by Nina Kann
Molecules 2010, 15(9), 6306-6331; https://doi.org/10.3390/molecules15096306 - 7 Sep 2010
Cited by 77 | Viewed by 11414
Abstract
Recent developments concerning the application of polymer supported organometallic reagents in solid phase synthesis are reviewed, with a special focus on methodology for carbon-carbon formation. Examples of reactions that are covered include the classical Suzuki, Sonogashira and Heck coupings, but also aryl amination, [...] Read more.
Recent developments concerning the application of polymer supported organometallic reagents in solid phase synthesis are reviewed, with a special focus on methodology for carbon-carbon formation. Examples of reactions that are covered include the classical Suzuki, Sonogashira and Heck coupings, but also aryl amination, epoxide opening, rearrangements, metathesis and cyclopropanation. Applications in the field of asymmetric synthesis are also discussed. Full article
(This article belongs to the Special Issue Solid Phase Synthesis)
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392 KiB  
Review
Transactivation of Genes Encoding for Phase II Enzymes and Phase III Transporters by Phytochemical Antioxidants
by Yoon Mee Yang, Kyoung Noh, Chang Yeob Han and Sang Geon Kim
Molecules 2010, 15(9), 6332-6348; https://doi.org/10.3390/molecules15096332 - 7 Sep 2010
Cited by 23 | Viewed by 10318
Abstract
The induction of phase II enzymes and phase III transporters contributes to the metabolism, detoxification of xenobiotics, antioxidant capacity, redox homeostasis and cell viability. Transactivation of the genes that encode for phase II enzymes and phase III transporters is coordinatively regulated by activating [...] Read more.
The induction of phase II enzymes and phase III transporters contributes to the metabolism, detoxification of xenobiotics, antioxidant capacity, redox homeostasis and cell viability. Transactivation of the genes that encode for phase II enzymes and phase III transporters is coordinatively regulated by activating transcription factors in response to external stimuli. Comprehensive studies indicate that antioxidant phytochemicals promote the induction of phase II enzymes and/or phase III transporters through various signaling pathways, including phosphoinositide 3-kinase, protein kinase C, and mitogen-activated protein kinases. This paper focuses on the molecular mechanisms and signaling pathways responsible for the transactivation of genes encoding for these proteins, as orchestrated by a series of transcription factors and related signaling components. Full article
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301 KiB  
Review
Honokiol and Magnolol as Multifunctional Antioxidative Molecules for Dermatologic Disorders
by Jui-Lung Shen, Kee-Ming Man, Po-Hsun Huang, Wen-Chi Chen, Der-Cherng Chen, Ya-Wen Cheng, Po-Len Liu, Ming-Chih Chou and Yung-Hsiang Chen
Molecules 2010, 15(9), 6452-6465; https://doi.org/10.3390/molecules15096452 - 16 Sep 2010
Cited by 139 | Viewed by 21033
Abstract
Chinese herbs have been and still are widely used as important remedies in Oriental medicine. Over the recent years, a variety of biologically active constituents have been isolated from these sources and confirmed to have multifunctional activity in experimental studies. Honokiol is a [...] Read more.
Chinese herbs have been and still are widely used as important remedies in Oriental medicine. Over the recent years, a variety of biologically active constituents have been isolated from these sources and confirmed to have multifunctional activity in experimental studies. Honokiol is a small-molecule polyphenol isolated from the genus Magnolia. It is accompanied by other related polyphenols, including magnolol, with which it shares certain biological properties. Recently, honokiol and magnolol have been found to have anti-oxidative, anti-inflammatory, anti-tumor, and anti-microbial properties in preclinical models, without appreciable toxicity. These findings have increased interest in bringing honokiol and magnolol to the clinic as novel therapeutic agents in dermatology. In this review, the findings concerning the major mechanisms of action of honokiol and magnolol are described. Knowledge of the multiple activities of honokiol and magnolol can assist with the development of honokiol and magnolol derivatives and the design of clinical trials that will maximize the potential benefit of honokiol and magnolol in the patient setting for dermatologic disorders. Full article
(This article belongs to the Special Issue Antioxidants)
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1102 KiB  
Review
The 9-Phenyl-9-fluorenyl Group for Nitrogen Protection in Enantiospecific Synthesis
by Essi J. Karppanen and Ari M. P. Koskinen
Molecules 2010, 15(9), 6512-6547; https://doi.org/10.3390/molecules15096512 - 17 Sep 2010
Cited by 13 | Viewed by 10883
Abstract
One of the biggest challenges in asymmetric synthesis is to prevent racemization of enantiopure starting materials. However, at least some of the enantiopurity is lost in most of the existing reactions used in synthetic organic chemistry. This translates into unnecessary material losses. Naturally [...] Read more.
One of the biggest challenges in asymmetric synthesis is to prevent racemization of enantiopure starting materials. However, at least some of the enantiopurity is lost in most of the existing reactions used in synthetic organic chemistry. This translates into unnecessary material losses. Naturally enantiopure proteinogenic amino acids that can be transformed into many useful intermediates in drug syntheses, for example, are especially vulnerable to this. The phenylfluoren-9-yl (Pf) group, a relatively rarely used protecting group, has proven to be able to prevent racemization in α-amino compounds. This review article showcases the use of Pf-protected amino acid derivatives in enantiospecific synthesis. Full article
(This article belongs to the Special Issue Protecting Group in Organic Synthesis)
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198 KiB  
Review
Kinin Receptor Antagonists as Potential Neuroprotective Agents in Central Nervous System Injury
by Emma Thornton, Jenna M Ziebell, Anna V Leonard and Robert Vink
Molecules 2010, 15(9), 6598-6618; https://doi.org/10.3390/molecules15096598 - 20 Sep 2010
Cited by 36 | Viewed by 10809
Abstract
Injury to the central nervous system initiates complex physiological, cellular and molecular processes that can result in neuronal cell death. Of interest to this review is the activation of the kinin family of neuropeptides, in particular bradykinin and substance P. These neuropeptides are [...] Read more.
Injury to the central nervous system initiates complex physiological, cellular and molecular processes that can result in neuronal cell death. Of interest to this review is the activation of the kinin family of neuropeptides, in particular bradykinin and substance P. These neuropeptides are known to have a potent pro-inflammatory role and can initiate neurogenic inflammation resulting in vasodilation, plasma extravasation and the subsequent development of edema. As inflammation and edema play an integral role in the progressive secondary injury that causes neurological deficits, this review critically examines kinin receptor antagonists as a potential neuroprotective intervention for acute brain injury, and more specifically, traumatic brain and spinal cord injury and stroke. Full article
(This article belongs to the Special Issue Neuroprotective Strategies)
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892 KiB  
Review
Structural and Pharmacological Effects of Ring-Closing Metathesis in Peptides
by Øyvind Jacobsen, Jo Klaveness and Pål Rongved
Molecules 2010, 15(9), 6638-6677; https://doi.org/10.3390/molecules15096638 - 21 Sep 2010
Cited by 36 | Viewed by 9672
Abstract
Applications of ring-closing alkene metathesis (RCM) in acyclic α- and β-peptides and closely related systems are reviewed, with a special emphasis on the structural and pharmacological effects of cyclization by RCM. Full article
(This article belongs to the Special Issue Ring-Closing Metathesis)
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