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Molecules, Volume 13, Issue 8 (August 2008), Pages 1530-2038

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Research

Jump to: Review

Open AccessArticle Isolation and Characterization of Phenolic Compounds from the Leaves of Salix matsudana
Molecules 2008, 13(8), 1530-1537; doi:10.3390/molecules13081530
Received: 2 July 2008 / Revised: 31 July 2008 / Accepted: 31 July 2008 / Published: 3 August 2008
Cited by 15 | PDF Full-text (194 KB) | HTML Full-text | XML Full-text
Abstract
A bioassay-guided in vitro screen has revealed that a 70% methanol extract of the leaves of Salix matsudana shows considerable inhibitory activity against cyclooxygenases (COX-1 and COX-2). A subsequent phytochemical study led to the isolation of a new flavonoid, matsudone A (1), [...] Read more.
A bioassay-guided in vitro screen has revealed that a 70% methanol extract of the leaves of Salix matsudana shows considerable inhibitory activity against cyclooxygenases (COX-1 and COX-2). A subsequent phytochemical study led to the isolation of a new flavonoid, matsudone A (1), together with five known flavonoids – luteolin (2), isoquercitrin (3), 7-methoxyflavone (4), luteolin 7-O-glucoside (5), 4',7-dihydroxyflavone (6) – and two phenolic glycosides, leonuriside A (7) and piceoside (8). Their structures were elucidated on the basis of extensive 1D- and 2D-NMR studies, high resolution ESI mass spectroscopic analyses and comparisons with literature data. The isolated compounds 1-8 were tested for their inhibitory activities against COX-1 and COX-2. Compounds 1, 5 and 6 were found to have potent inhibitory effect on COX-2 and compounds 3-5 exhibited moderate inhibition against COX-1. Full article
Open AccessArticle Structure Determination of β-Glucans from Ganoderma lucidum with Matrix-assisted Laser Desorption/ionization (MALDI) Mass Spectrometry
Molecules 2008, 13(8), 1538-1550; doi:10.3390/molecules13081538
Received: 26 May 2008 / Revised: 21 June 2008 / Accepted: 25 July 2008 / Published: 3 August 2008
Cited by 20 | PDF Full-text (481 KB) | HTML Full-text | XML Full-text
Abstract
A novel method that uses matrix-assisted laser desorption/ionization (MALDI) mass spectrometry to analyze molecular weight and sequencing of glucan in Ganoderma lucidum is presented. Thus, β-glucan, which was isolated from fruiting bodies of G. lucidum, was measured in a direct and [...] Read more.
A novel method that uses matrix-assisted laser desorption/ionization (MALDI) mass spectrometry to analyze molecular weight and sequencing of glucan in Ganoderma lucidum is presented. Thus, β-glucan, which was isolated from fruiting bodies of G. lucidum, was measured in a direct and fast way using MALDI mass spectrometry. In addition, tandem mass spectrometry of permethylated glucans of G. lucidum, dextran, curdlan and maltohexaose were also pursued and different fragment patterns were obtained. The G. lucidum glucan structure was determined and this method for linkage analysis of permethylated glucan has been proven feasible. Full article
Open AccessArticle 4-Azatricyclo[5.2.2.02,6]undecane-3,5,8-triones as Potential Pharmacological Agents
Molecules 2008, 13(8), 1570-1583; doi:10.3390/molecules13081570
Received: 14 May 2008 / Revised: 19 June 2008 / Accepted: 25 July 2008 / Published: 6 August 2008
Cited by 23 | PDF Full-text (297 KB) | HTML Full-text | XML Full-text
Abstract A series of twenty six arylpiperazine and aminoalkanol derivatives of 4-azatricyclo[ 5.2.2.02,6]undecane-3,5,8-trione have been prepared. The synthesized compounds were evaluated for their cytotoxicity and anti-HIV-1 activity in MT-4 cells. Full article
Open AccessArticle A Simple, Rapid and Mild One Pot Synthesis of Benzene Ring Acylated and Demethylated Analogues of Harmine under Solvent-free Conditions
Molecules 2008, 13(8), 1584-1598; doi:10.3390/molecules1301584
Received: 6 May 2008 / Revised: 24 June 2008 / Accepted: 23 July 2008 / Published: 6 August 2008
Cited by 2 | PDF Full-text (221 KB) | HTML Full-text | XML Full-text
Abstract
A simple, rapid, solvent-free, room temperature one pot synthesis of benzene ring acylated and demethylated analogues of harmine using acyl halides/acid anhydrides and AlCl3 has been developed. Eight different acyl halides/acid anhydrides were used in the synthesis. The resulting mixture of [...] Read more.
A simple, rapid, solvent-free, room temperature one pot synthesis of benzene ring acylated and demethylated analogues of harmine using acyl halides/acid anhydrides and AlCl3 has been developed. Eight different acyl halides/acid anhydrides were used in the synthesis. The resulting mixture of products was separated by column chromatography to afford 10- and 12-monoacyl analogues, along with 10,12-diacyl-11-hydroxy products. In five cases the corresponding 10-acyl-11-hydroxy analogues were also obtained. Yields from the eight syntheses (29 products in total) were in the 6-34% range and all compounds were fully characterized. Full article
(This article belongs to the Special Issue Alkaloids: Novel Therapeutic Perspectives)
Open AccessArticle Statistical Assessment of Solvent Mixture Models Used for Separation of Biological Active Compounds
Molecules 2008, 13(8), 1617-1639; doi:10.3390/molecules13081617
Received: 23 May 2008 / Revised: 7 August 2008 / Accepted: 7 August 2008 / Published: 11 August 2008
Cited by 4 | PDF Full-text (238 KB) | HTML Full-text | XML Full-text
Abstract
Two mathematical models with seven and six parameters have been created for use as methods for identification of the optimum mobile phase in chromatographic separations. A series of chromatographic response functions were proposed and implemented in order to assess and validate the [...] Read more.
Two mathematical models with seven and six parameters have been created for use as methods for identification of the optimum mobile phase in chromatographic separations. A series of chromatographic response functions were proposed and implemented in order to assess and validate the models. The assessment was performed on a set of androstane isomers. Pearson, Spearman, Kendall tau-a,b,c and Goodman-Kruskal correlation coefficients were used in order to identify and to quantify the link and its nature (quantitative, categorical, semi-quantitative, both quantitative and categorical) between experimental values and the values estimated by the mathematical models. The study revealed that the six parameter model is valid and reliable for five chromatographic response factors (retardation factor, retardation factor ordered ascending by the chromatographic peak, resolution of pairs of compound, resolution matrix of successive chromatographic peaks, and quality factor). Furthermore, the model could be used as an instrument in analysis of the quality of experimental data. The results obtained by applying the model with six parameters for deviations of rank sums suggest that the data of the experiment no. 8 are questionable. Full article
Open AccessArticle New Acetylenic Norlignan Compounds from Rhizomes of Curculigo crassifolia
Molecules 2008, 13(8), 1696-1701; doi:10.3390/molecules13081696
Received: 13 June 2008 / Revised: 1 August 2008 / Accepted: 6 August 2008 / Published: 13 August 2008
Cited by 8 | PDF Full-text (190 KB) | HTML Full-text | XML Full-text
Abstract
Two pairs of diastereoisomeric acetylenic norlignan compounds with PhCH(OR1)CH(OR2)CH2C≡CPh skeleta: (1R, 2R)-1-O-methylnyasicoside (1) and (1S, 2R)-1-O-methylnyasicoside (2), and (1R, 2R)-crassifogenin D (3) and (1S, 2R)- crassifogenin D (4), were isolated from the ethanolic extract of rhizomes [...] Read more.
Two pairs of diastereoisomeric acetylenic norlignan compounds with PhCH(OR1)CH(OR2)CH2C≡CPh skeleta: (1R, 2R)-1-O-methylnyasicoside (1) and (1S, 2R)-1-O-methylnyasicoside (2), and (1R, 2R)-crassifogenin D (3) and (1S, 2R)- crassifogenin D (4), were isolated from the ethanolic extract of rhizomes of Curculigo crassifolia. Compounds 3 and 4 are new and their structures were elucidated on the basis of spectroscopic evidence and comparisons with literature data. Full article
Open AccessArticle Extraction and Separation of Volatile and Fixed Oils from Berries of Laurus nobilis L. by Supercritical CO2
Molecules 2008, 13(8), 1702-1711; doi:10.3390/molecules13081702
Received: 26 June 2008 / Revised: 28 July 2008 / Accepted: 5 August 2008 / Published: 13 August 2008
Cited by 17 | PDF Full-text (172 KB) | HTML Full-text | XML Full-text
Abstract
Isolation of volatile and fixed oils from dried berries of Laurus nobilis L. from Tunisia have been obtained by supercritical fractioned extraction with carbon dioxide. Extraction experiments were carried out at a temperature of 40 °C and pressures of 90 and 250 [...] Read more.
Isolation of volatile and fixed oils from dried berries of Laurus nobilis L. from Tunisia have been obtained by supercritical fractioned extraction with carbon dioxide. Extraction experiments were carried out at a temperature of 40 °C and pressures of 90 and 250 bar. The extraction step performed at 90 bar produced a volatile fraction mainly composed of (E)-β-ocimene (20.9%), 1,8-cineole (8.8%), α-pinene (8.0%), β-longipinene (7.1%), linalool acetate (4.5%), cadinene (4.7%), β-pinene (4.2%), α-terpinyl acetate (3.8%) and α-bulnesene (3.5%). The oil yield in this step of the process was 0.9 % by weight charged. The last extraction step at 250 bar produced an odorless liquid fraction, in which a very small percentage of fragrance compounds was found, whereas triacylglycerols were dominant. The yield of this step was 15.0 % by weight. The most represented fatty acids of the whole berry fixed oil were 12:0 (27.6%), 18:1 n-9 (27.1%), 18:2 n-6 (21.4%), and 16:0 (17,1%), with the 18:1 n-9 and 18:2 n-6 unsaturated fatty acids in particular averaging 329 μg/mg of oil. Full article
Open AccessArticle New Triterpene Diglycosides from the Rhizome of Cimifuga foetida
Molecules 2008, 13(8), 1712-1721; doi:10.3390/molecules13081712
Received: 17 May 2008 / Revised: 17 July 2008 / Accepted: 18 July 2008 / Published: 13 August 2008
Cited by 7 | PDF Full-text (269 KB) | HTML Full-text | XML Full-text
Abstract
Five new 9,19-cycloartane triterpene diglycosides, which have been named cimiaceroside C (1), and cimifosides A-D (2-5) together with the known compounds cimiracemoside D (6), cimidahurine (7) and α-D-glucopyranosyl-l-β-D-fructofuranoside (8) were isolated from the rhizome of Cimicifuga foetida. The new triterpene diglycosides 1-5 [...] Read more.
Five new 9,19-cycloartane triterpene diglycosides, which have been named cimiaceroside C (1), and cimifosides A-D (2-5) together with the known compounds cimiracemoside D (6), cimidahurine (7) and α-D-glucopyranosyl-l-β-D-fructofuranoside (8) were isolated from the rhizome of Cimicifuga foetida. The new triterpene diglycosides 1-5 were identified as cimiacerol-3-O-β-D-xylopyranosyl-(1''→3')-β-D-xylopyranoside, 12β-hydroxycimigenol-3-O-β-D-xylopyranosyl-(1''→3')-β-D-xylopyranoside, 25-Oacetylcimig- enol-3-O-β-D-xylopyranosyl-(1''→3')-β-D-xylopyranoside, 24- acetylhydroshengmanol-3-O-β-D-xylopyranosyl-(1''→3')-β-D-xylopyranoside and 26- deoxyacetylacteol-3-O-β-D-xylo- pyranosyl-(1''→3')-β-D-xylopyranoside, respectively, based on analysis of their spectral data and chemical reactions. Full article
Open AccessArticle 1,2,5,10,11,14-Hexaoxadispiro[5.2.5.2]hexadecanes: Novel Spirofused Bis-Trioxane Peroxides
Molecules 2008, 13(8), 1743-1758; doi:10.3390/molecules13081743
Received: 28 July 2008 / Revised: 15 August 2008 / Accepted: 18 August 2008 / Published: 19 August 2008
Cited by 4 | PDF Full-text (759 KB) | HTML Full-text | XML Full-text
Abstract
A set of new bis-spirofused 1,2,4-trioxanes 4a-d was obtained from the reaction of cyclohexane-1,4-dione with allylic hydroperoxides 2a-d, bearing an additional hydroxy group in the homoallylic position, by diastereoselective photooxygenation of allylic alcohols 1a-d and subsequent BF3-catalyzed peroxyacetalization with the [...] Read more.
A set of new bis-spirofused 1,2,4-trioxanes 4a-d was obtained from the reaction of cyclohexane-1,4-dione with allylic hydroperoxides 2a-d, bearing an additional hydroxy group in the homoallylic position, by diastereoselective photooxygenation of allylic alcohols 1a-d and subsequent BF3-catalyzed peroxyacetalization with the diketone. From the reaction of a monoprotected cyclohexane-1,4-dione 5 with the allylic hydroperoxide 6 derived from the singlet oxygenation of methyl hydroxytiglate, one monospiro compound was obtained, the 1,2,4-trioxane ketone 7, as well as a mixture of the diastereoisomeric syn- and anti bis-1,2,4-trioxanes 8. The structures of bis-1,2,4-trioxanes were examined theoretically by DFT methods and compared with X-ray structural data in order to evaluate the preferential trioxane ring conformational orientation. Full article
(This article belongs to the Special Issue Spiro Compounds)
Open AccessArticle Amifostine Protection Against Mitomycin-induced Chromosomal Breakage in Fanconi Anaemia Lymphocytes
Molecules 2008, 13(8), 1759-1772; doi:10.3390/molecules13081759
Received: 7 June 2008 / Revised: 13 August 2008 / Accepted: 14 August 2008 / Published: 21 August 2008
Cited by 4 | PDF Full-text (226 KB) | HTML Full-text | XML Full-text
Abstract
Fanconi anaemia (FA) is a rare genetic chromosomal instability syndrome caused by impairment of DNA repair and reactive oxygen species (ROS) imbalance. This disease is also related to bone marrow failure and cancer. Treatment of these complications with radiation and alkylating agents may enhance chromosomal breakage. We have evaluated the effect of amifostine (AMF) on basal and mitomycin C (MMC)-induced chromosomal breakage in FA blood cells using the micronucleus assay. The basal micronuclei count was higher among FA patients than healthy subjects. Pre-treatment with AMF significantly inhibited micronucleation induced by MMC in healthy subjects (23.4 ± 4.0 – MMC vs 12.3 ± 2.9 – AMF →MMC) MN/1000CB, p < 0.01, one way ANOVA) as well as in FA patients (80.0 ± 5.8 – MMC vs 40.1 ± 5.8 – AMF →MMC) MN/1000CB, p < 0.01, ANOVA). Release of ROS by peripheral blood mononuclear cells treated with AMF →MMC and measured by chemoluminometry showed that AMF-protection was statistically higher among FA patients than in healthy individuals. Based on these results we suggest that AMF prevents chromosomal breakage induced by MMC, probably by its antioxidant effect. Full article
Open AccessCommunication Synthesis of RP 48497, an Impurity of Eszopiclone
Molecules 2008, 13(8), 1817-1821; doi:10.3390/molecules13081817
Received: 5 June 2008 / Revised: 8 August 2008 / Accepted: 12 August 2008 / Published: 22 August 2008
Cited by 3 | PDF Full-text (161 KB) | HTML Full-text | XML Full-text
Abstract
RP 48497 is a photodegradation product of eszopiclone, a non-benzodiazepine sedative-hypnotic used in the treatment of insomnia. We report herein the first synthesis of RP 48497 via reduction, chlorination, and recyclization of 6-(5-chloropyridin-2-yl)-7-hydroxy-6,7-dihydropyrrolo[3,4-b]pyrazin-5-one (3), a key intermediate in the synthesis of eszopiclone. [...] Read more.
RP 48497 is a photodegradation product of eszopiclone, a non-benzodiazepine sedative-hypnotic used in the treatment of insomnia. We report herein the first synthesis of RP 48497 via reduction, chlorination, and recyclization of 6-(5-chloropyridin-2-yl)-7-hydroxy-6,7-dihydropyrrolo[3,4-b]pyrazin-5-one (3), a key intermediate in the synthesis of eszopiclone. The structure of RP 48497 was confirmed by its 1H-NMR and MS data. The mechanism of the reduction step in the synthesis of RP 48497 was also studied and the key parameters were determined. These findings should be important for quality control purposes in the manufacture of eszopiclone. Full article
Open AccessArticle CoMFA, CoMSIA and Eigenvalue Analysis on Dibenzodioxepinone and Dibenzodioxocinone Derivatives as Cholesteryl Ester Transfer Protein Inhibitors
Molecules 2008, 13(8), 1822-1839; doi:10.3390/molecules13081822
Received: 29 July 2008 / Revised: 7 August 2008 / Accepted: 7 August 2008 / Published: 22 August 2008
Cited by 5 | PDF Full-text (1424 KB) | HTML Full-text | XML Full-text
Abstract
CoMFA, CoMSIA and eigenvalue analysis (EVA) were performed to study the structural features of 61 diverse dibenzodioxepinone and dibenzodioxocinone analogues to probe cholesteryl ester transfer protein (CETP) inhibitory activity. Three methods yielded statistically significant models upon assessment of cross-validation, bootstrapping, and progressive [...] Read more.
CoMFA, CoMSIA and eigenvalue analysis (EVA) were performed to study the structural features of 61 diverse dibenzodioxepinone and dibenzodioxocinone analogues to probe cholesteryl ester transfer protein (CETP) inhibitory activity. Three methods yielded statistically significant models upon assessment of cross-validation, bootstrapping, and progressive scrambling. This was further validated by an external set of 13 derivatives. Our results demonstrate that three models have a good interpolation as well as extrapolation. The hydrophobic features were confirmed to contribute significantly to inhibitor potencies, while a pre-oriented hydrogen bond provided by the hydroxyl group at the 3-position indicated a good correlation with previous SAR, and a hydrogen bond acceptor may play a crucial role in CETP inhibition. These derived models may help us to gain a deeper understanding of the binding interaction of these lactone-based compounds and aid in the design of new potent compounds against CETP. Full article
Open AccessArticle Synthesis of a Novel D-Glucose-Conjugated 15-Crown-5 Ether with a Spiro Ketal Structure
Molecules 2008, 13(8), 1840-1845; doi:10.3390/molecules13081840
Received: 18 July 2008 / Revised: 12 August 2008 / Accepted: 19 August 2008 / Published: 22 August 2008
Cited by 6 | PDF Full-text (203 KB) | HTML Full-text | XML Full-text
Abstract
This paper describes a synthetic approach to a novel D-glucose-conjugated 15-crown-5 ether having a spiroketal structure starting from a 1-C-vinylated glucose derivative. The approach consists of the glycosylation of the vinylated glucose derivative to give an ethyleneoxy spacer derivative using bismuth(III) triflate, [...] Read more.
This paper describes a synthetic approach to a novel D-glucose-conjugated 15-crown-5 ether having a spiroketal structure starting from a 1-C-vinylated glucose derivative. The approach consists of the glycosylation of the vinylated glucose derivative to give an ethyleneoxy spacer derivative using bismuth(III) triflate, the conversion of the 1-C-vinyl group of the glucoside produced into a carboxylic acid group, and the intramolecular condensation between the carboxyl group and the terminal hydroxyl group in the ethyleneoxy spacer. A D-glucose-conjugated 15-crown-5 ether having a unique spiroketal structure was thus successfully synthesized. Full article
(This article belongs to the Special Issue Spiro Compounds)
Open AccessArticle Oligomerization of Indole Derivatives with Incorporation of Thiols
Molecules 2008, 13(8), 1846-1863; doi:10.3390/molecules13081846
Received: 10 June 2008 / Revised: 18 August 2008 / Accepted: 19 August 2008 / Published: 26 August 2008
PDF Full-text (424 KB) | HTML Full-text | XML Full-text
Abstract
Two molecules of indole derivative, e.g. indole-5-carboxylic acid, reacted with one molecule of thiol, e.g. 1,2-ethanedithiol, in the presence of trifluoroacetic acid to yield adducts such as 3-[2-(2-amino-5-carboxyphenyl)-1-(2-mercaptoethylthio)ethyl]-1Hindole-5-carboxylic acid. Parallel formation of dimers, such as 2,3-dihydro-1H,1'H-2,3'-biindole-5,5'-dicarboxylic acid and trimers, such as 3,3'-[2-(2-amino-5-carboxyphenyl) [...] Read more.
Two molecules of indole derivative, e.g. indole-5-carboxylic acid, reacted with one molecule of thiol, e.g. 1,2-ethanedithiol, in the presence of trifluoroacetic acid to yield adducts such as 3-[2-(2-amino-5-carboxyphenyl)-1-(2-mercaptoethylthio)ethyl]-1Hindole-5-carboxylic acid. Parallel formation of dimers, such as 2,3-dihydro-1H,1'H-2,3'-biindole-5,5'-dicarboxylic acid and trimers, such as 3,3'-[2-(2-amino-5-carboxyphenyl) ethane-1,1-diyl]bis(1H-indole-5-carboxylic acid) of the indole derivatives was also observed. Reaction of a mixture of indole and indole-5-carboxylic acid with 2-phenylethanethiol proceeded in a regioselective way, affording 3-[2-(2-aminophenyl)-1-(phenethylthio)ethyl]-1H-indole-5-carboxylic acid. An additional product of this reaction was 3-[2-(2-aminophenyl)-1-(phenethylthio)ethyl]-2,3-dihydro-1H,1'H-2,3'-biindole-5'-carboxylic acid, which upon standing in DMSO-d6 solution gave 3-[2-(2-aminophenyl)-1-(phenethylthio)ethyl]-1H,1'H-2,3'-biindole-5'-carboxylic acid. Structures of all compounds were elucidated by NMR, and a mechanism for their formation was suggested. Full article
Open AccessArticle Evaluation of the Chemical Composition of Brazilian Commercial Cymbopogon citratus (D.C.) Stapf Samples
Molecules 2008, 13(8), 1864-1874; doi:10.3390/molecules13081864
Received: 11 July 2008 / Revised: 21 August 2008 / Accepted: 22 August 2008 / Published: 27 August 2008
Cited by 37 | PDF Full-text (224 KB) | HTML Full-text | XML Full-text
Abstract
The concentration and the chemical composition of the essential oils obtained from different samples of Cymbopogon citratus were evaluated. Among the 12 samples investigated (11 dried leaf samples and fresh plant leaves), seven presented essential oil concentrations within the threshold established by [...] Read more.
The concentration and the chemical composition of the essential oils obtained from different samples of Cymbopogon citratus were evaluated. Among the 12 samples investigated (11 dried leaf samples and fresh plant leaves), seven presented essential oil concentrations within the threshold established by the Brazilian legislation. The moisture content was also determined and the majority of the samples presented humidity contents near 12%. The GC and GC/MS analyses of the essential oils led to identification of 22 compounds, with neral and geranial as the two major components. The total percentage of these two compounds varied within the investigated sample oils from 40.7% to 75.4%. In addition, a considerable variation in the chemical composition of the analyzed samples was observed. The process of grinding the leaves significantly decreased (by up to 68%) the essential oil content, as well as the percentage of myrcene in the oils. Full article
Open AccessCommunication A New 3-Benzylchroman Derivative from Sappan Lignum (Caesalpinia sappan)
Molecules 2008, 13(8), 1923-1930; doi:10.3390/molecules13081923
Received: 28 July 2008 / Revised: 11 August 2008 / Accepted: 11 August 2008 / Published: 28 August 2008
Cited by 22 | PDF Full-text (264 KB) | HTML Full-text | XML Full-text
Abstract
3'-Deoxy-4-O-methylepisappanol, a new 3-benzylchroman derivative, was isolated from Sappan Lignum, together with thirteen known chemical compounds identified as protosappanin A, sappanchalcone, sappanone B, palmitic acid, (+)-(8S,8'S)-bisdihydrosiringenin, brazilein, 3-deoxysappanchalcone, (+)-lyoniresinol, 3-deoxysappanone B, protosappanin B, isoprotosappanin B, 3'-O-methylbrazilin and brazilin, respectively. Among these known [...] Read more.
3'-Deoxy-4-O-methylepisappanol, a new 3-benzylchroman derivative, was isolated from Sappan Lignum, together with thirteen known chemical compounds identified as protosappanin A, sappanchalcone, sappanone B, palmitic acid, (+)-(8S,8'S)-bisdihydrosiringenin, brazilein, 3-deoxysappanchalcone, (+)-lyoniresinol, 3-deoxysappanone B, protosappanin B, isoprotosappanin B, 3'-O-methylbrazilin and brazilin, respectively. Among these known compounds, this is the first time that (+)-(8S,8'S)-bisdihydrosiringenin was obtained from the family Caesalpiniaceae. Full article
Open AccessArticle Flavonoids and a New Polyacetylene from Bidens parviflora Willd
Molecules 2008, 13(8), 1931-1941; doi:10.3390/molecules13081931
Received: 20 July 2008 / Revised: 19 August 2008 / Accepted: 26 August 2008 / Published: 28 August 2008
Cited by 63 | PDF Full-text (226 KB) | HTML Full-text | XML Full-text
Abstract
Fifteen flavonoids, 1-7 and 9-16, and a polyacetylene, 8, were isolated from the ethanol extract of the dried whole plant of Bidens parviflora Willd. by various chromatographic techniques. Their structures have been elucidated on the basis of spectroscopic analyses and chemical studies. [...] Read more.
Fifteen flavonoids, 1-7 and 9-16, and a polyacetylene, 8, were isolated from the ethanol extract of the dried whole plant of Bidens parviflora Willd. by various chromatographic techniques. Their structures have been elucidated on the basis of spectroscopic analyses and chemical studies. Compound 8 is new and was identified as 3-(R),8(E)-decene-4,6-diyne-1,3,10-triol. All the flavonoid compounds were isolated for the first time from this plant species. Full article
(This article belongs to the Special Issue Phenolics and Polyphenolics)

Review

Jump to: Research

Open AccessReview 5-Fluorouracil: Mechanisms of Resistance and Reversal Strategies
Molecules 2008, 13(8), 1551-1569; doi:10.3390/molecules13081551
Received: 18 June 2008 / Revised: 1 July 2008 / Accepted: 15 July 2008 / Published: 5 August 2008
Cited by 103 | PDF Full-text (214 KB) | HTML Full-text | XML Full-text
Abstract
The purpose of this work is to review the published studies on the mechanisms of action and resistance of 5-fluorouracil. The review is divided into three main sections: mechanisms of anti-tumor action, studies of the resistance to the drug, and procedures for [...] Read more.
The purpose of this work is to review the published studies on the mechanisms of action and resistance of 5-fluorouracil. The review is divided into three main sections: mechanisms of anti-tumor action, studies of the resistance to the drug, and procedures for the identification of new genes involved in resistance with microarray techniques. The details of the induction and reversal of the drug resistance are also described. Full article
(This article belongs to the Special Issue 5-Fluorouracil)
Open AccessReview Composition and Applications of Aloe vera Leaf Gel
Molecules 2008, 13(8), 1599-1616; doi:10.3390/molecules13081599
Received: 28 May 2008 / Accepted: 25 July 2008 / Published: 8 August 2008
Cited by 194 | PDF Full-text (230 KB) | HTML Full-text | XML Full-text
Abstract
Many of the health benefits associated with Aloe vera have been attributed to the polysaccharides contained in the gel of the leaves. These biological activities include promotion of wound healing, antifungal activity, hypoglycemic or antidiabetic effects antiinflammatory, anticancer, immunomodulatory and gastroprotective properties. [...] Read more.
Many of the health benefits associated with Aloe vera have been attributed to the polysaccharides contained in the gel of the leaves. These biological activities include promotion of wound healing, antifungal activity, hypoglycemic or antidiabetic effects antiinflammatory, anticancer, immunomodulatory and gastroprotective properties. While the known biological activities of A. vera will be briefly discussed, it is the aim of this review to further highlight recently discovered effects and applications of the leaf gel. These effects include the potential of whole leaf or inner fillet gel liquid preparations of A. vera to enhance the intestinal absorption and bioavailability of co-administered compounds as well as enhancement of skin permeation. In addition, important pharmaceutical applications such as the use of the dried A. vera gel powder as an excipient in sustained release pharmaceutical dosage forms will be outlined. Full article
Open AccessReview Chemical and Enzymatic Approaches to Carbohydrate-Derived Spiroketals: Di-D-Fructose Dianhydrides (DFAs)
Molecules 2008, 13(8), 1640-1670; doi:10.3390/molecules13081640
Received: 20 June 2008 / Revised: 22 July 2008 / Accepted: 28 July 2008 / Published: 12 August 2008
Cited by 14 | PDF Full-text (512 KB) | HTML Full-text | XML Full-text
Abstract
Di-D-fructose dianhydrides (DFAs) comprise a unique family of stereoisomeric spiro-tricyclic disaccharides formed upon thermal and/or acidic activation of sucroseand/ or D-fructose-rich materials. The recent discovery of the presence of DFAs in food products and their remarkable nutritional features has attracted considerable interest [...] Read more.
Di-D-fructose dianhydrides (DFAs) comprise a unique family of stereoisomeric spiro-tricyclic disaccharides formed upon thermal and/or acidic activation of sucroseand/ or D-fructose-rich materials. The recent discovery of the presence of DFAs in food products and their remarkable nutritional features has attracted considerable interest from the food industry. DFAs behave as low-caloric sweeteners and have proven to exert beneficial prebiotic nutritional functions, favouring the growth of Bifidobacterium spp. In the era of functional foods, investigation of the beneficial properties of DFAs has become an important issue. However, the complexity of the DFA mixtures formed during caramelization or roasting of carbohydrates by traditional procedures (up to 14 diastereomeric spiroketal cores) makes evaluation of their individual properties a difficult challenge. Great effort has gone into the development of efficient procedures to obtain DFAs in pure form at laboratory and industrial scale. This paper is devoted to review the recent advances in the stereoselective synthesis of DFAs by means of chemical and enzymatic approaches, their scope, limitations, and complementarities. Full article
(This article belongs to the Special Issue Spiro Compounds)
Open AccessReview Fucoidan: Structure and Bioactivity
Molecules 2008, 13(8), 1671-1695; doi:10.3390/molecules13081671
Received: 20 June 2008 / Revised: 22 July 2008 / Accepted: 28 July 2008 / Published: 12 August 2008
Cited by 298 | PDF Full-text (301 KB) | HTML Full-text | XML Full-text
Abstract
Fucoidan refers to a type of polysaccharide which contains substantial percentages of L-fucose and sulfate ester groups, mainly derived from brown seaweed. For the past decade fucoidan has been extensively studied due to its numerous interesting biological activities. Recently the search for [...] Read more.
Fucoidan refers to a type of polysaccharide which contains substantial percentages of L-fucose and sulfate ester groups, mainly derived from brown seaweed. For the past decade fucoidan has been extensively studied due to its numerous interesting biological activities. Recently the search for new drugs has raised interest in fucoidans. In the past few years, several fucoidans’ structures have been solved, and many aspects of their biological activity have been elucidated. This review summarizes the research progress on the structure and bioactivity of fucoidan and the relationships between structure and bioactivity. Full article
Open AccessReview Application of Metabolic Engineering to the Production of Scopolamine
Molecules 2008, 13(8), 1722-1742; doi:10.3390/molecules13081722
Received: 3 June 2008 / Revised: 12 August 2008 / Accepted: 14 August 2008 / Published: 18 August 2008
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Abstract
Scopolamine is an alkaloid widely used in medicine for its anticholinergic activity. The aim of this review is to show that metabolic engineering techniques constitute a suitable tool to improve the production of tropane alkaloids, focusing in particular on scopolamine. We present [...] Read more.
Scopolamine is an alkaloid widely used in medicine for its anticholinergic activity. The aim of this review is to show that metabolic engineering techniques constitute a suitable tool to improve the production of tropane alkaloids, focusing in particular on scopolamine. We present an overview of results obtained by various research groups, including our own, who have studied the overexpression of genes involved in the biosynthesis of scopolamine in different plant species that produce tropane alkaloids. Experiments carried out to improve production in hairy root cultures will also be described, as well as those attempting to biotransform hyoscyamine into scopolamine in roots and transgenic tobacco cells. Full article
(This article belongs to the Special Issue Alkaloids: Novel Therapeutic Perspectives)
Open AccessReview Trehalose and Trehalose-based Polymers for Environmentally Benign, Biocompatible and Bioactive Materials
Molecules 2008, 13(8), 1773-1816; doi:10.3390/molecules13081773
Received: 13 July 2008 / Accepted: 11 August 2008 / Published: 21 August 2008
Cited by 39 | PDF Full-text (1744 KB) | HTML Full-text | XML Full-text
Abstract
Trehalose is a non-reducing disaccharide that is found in many organisms but not in mammals. This sugar plays important roles in cryptobiosis of selaginella mosses, tardigrades (water bears), and other animals which revive with water from a state of suspended animation induced [...] Read more.
Trehalose is a non-reducing disaccharide that is found in many organisms but not in mammals. This sugar plays important roles in cryptobiosis of selaginella mosses, tardigrades (water bears), and other animals which revive with water from a state of suspended animation induced by desiccation. The interesting properties of trehalose are due to its unique symmetrical low-energy structure, wherein two glucose units are bonded face-to-face by 1→1-glucoside links. The Hayashibara Co. Ltd., is credited for developing an inexpensive, environmentally benign and industrial-scale process for the enzymatic conversion of α-1,4-linked polyhexoses to α,α-D-trehalose, which made it easy to explore novel food, industrial, and medicinal uses for trehalose and its derivatives. Trehalosechemistry is a relatively new and emerging field, and polymers of trehalose derivatives appear environmentally benign, biocompatible, and biodegradable. The discriminating properties of trehalose are attributed to its structure, symmetry, solubility, kinetic and thermodynamic stability and versatility. While syntheses of trehalose-based polymer networks can be straightforward, syntheses and characterization of well defined linear polymers with tailored properties using trehalose-based monomers is challenging, and typically involves protection and deprotection of hydroxyl groups to attain desired structural, morphological, biological, and physical and chemical properties in the resulting products. In this review, we will overview known literature on trehalose’s fascinating involvement in cryptobiology; highlight its applications in many fields; and then discuss methods we used to prepare new trehalose-based monomers and polymers and explain their properties. Full article
Open AccessReview Rigorous Biogenetic Network for a Group of Indole Alkaloids Derived from Strictosidine
Molecules 2008, 13(8), 1875-1896; doi:10.3390/molecules13081875
Received: 5 August 2008 / Revised: 24 August 2008 / Accepted: 26 August 2008 / Published: 27 August 2008
Cited by 18 | PDF Full-text (410 KB) | HTML Full-text | XML Full-text
Abstract
Strictosidine, the precursor of more than 2,500 indole alkaloids, was isolated from four species of three plant families. By searching the Dictionary of Natural Products on DVD it was found that about 150 indole alkaloids were obtained from the same species (coalkaloids), [...] Read more.
Strictosidine, the precursor of more than 2,500 indole alkaloids, was isolated from four species of three plant families. By searching the Dictionary of Natural Products on DVD it was found that about 150 indole alkaloids were obtained from the same species (coalkaloids), which is a direct proof of their common origin. On the base of their threedimensional structure, taxonomic properties and standard reaction mechanisms an extended network was established which involved the four fundamental skeletons, the three types of carbon framework in the secologanin subunit and all major groups of indole alkaloids derived from secologanin and tryptamine (except a few minor groups, in which only less then 10 alkaloids were known). The system was extended to the heterodimer indole alkaloids and the quinoindole alkaloids as well. Full article
(This article belongs to the Special Issue Alkaloids: Novel Therapeutic Perspectives)
Open AccessReview Efficacy of the Oral Fluorouracil Pro-drug Capecitabine in Cancer Treatment: a Review
Molecules 2008, 13(8), 1897-1922; doi:10.3390/molecules13081897
Received: 30 May 2008 / Revised: 15 August 2008 / Accepted: 25 August 2008 / Published: 27 August 2008
Cited by 36 | PDF Full-text (289 KB) | HTML Full-text | XML Full-text
Abstract
Capecitabine (Xeloda®) was developed as a pro-drug of fluorouracil (FU), with the aim of improving tolerability and intratumor drug concentrations through its tumorspecific conversion to the active drug. The purpose of this paper is to review the available information on capecitabine, focusing [...] Read more.
Capecitabine (Xeloda®) was developed as a pro-drug of fluorouracil (FU), with the aim of improving tolerability and intratumor drug concentrations through its tumorspecific conversion to the active drug. The purpose of this paper is to review the available information on capecitabine, focusing on its clinical effectiveness against various carcinomas. Identification of all eligible English trails was made by searching the PubMed and Cochrane databases from 1980 to 2007. Search terms included capecitabine, Xeloda and cancer treatment. Nowadays, FDA has approved the use of capecitabine as a first line therapy in patients with metastatic colorectal cancer when single-agent fluoropyrimidine is preferred. The drug is also approved for use as a single agent in metastatic breast cancer patients who are resistant to both anthracycline and paclitaxel-based regimens or when further anthracycline treatment is contraindicated. It is also approved in combination with docetaxel after failure of prior anthracycline-based chemotherapy. In patients with prostate, pancreatic, renal cell and ovarian carcinomas, capecitabine as a single-agent or in combination with other drugs has also shown benefits. Improved tolerability and comparable efficacy, compared with the intravenous FU/LV combination, in addition to its oral administration, make capecitabine an attractive option for the treatment of several types of carcinomas. Full article
(This article belongs to the Special Issue 5-Fluorouracil)
Open AccessReview Asymmetric Synthesis of Naturally Occuring Spiroketals
Molecules 2008, 13(8), 1942-2038; doi:10.3390/molecules13081942
Received: 21 July 2008 / Revised: 22 August 2008 / Accepted: 22 August 2008 / Published: 28 August 2008
Cited by 51 | PDF Full-text (845 KB) | HTML Full-text | XML Full-text
Abstract
Spiroketals are widely found as substructures of many naturally occurring compounds from diverse sources including plants, animals as well as microbes. Naturally occurring spiroketals are biologically active and most of them are chiral molecules. This article aims at reviewing the asymmetric synthesis [...] Read more.
Spiroketals are widely found as substructures of many naturally occurring compounds from diverse sources including plants, animals as well as microbes. Naturally occurring spiroketals are biologically active and most of them are chiral molecules. This article aims at reviewing the asymmetric synthesis of biologically active spiroketals for last 10 years (1998-2007). Full article
(This article belongs to the Special Issue Spiro Compounds)

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