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Molecules, Volume 18, Issue 9 (September 2013), Pages 10095-11657

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Open AccessArticle A Modular Approach to Triazole-Containing Chemical Inducers of Dimerisation for Yeast Three-Hybrid Screening
Molecules 2013, 18(9), 11639-11657; https://doi.org/10.3390/molecules180911639
Received: 1 August 2013 / Revised: 5 September 2013 / Accepted: 6 September 2013 / Published: 23 September 2013
Cited by 8 | Viewed by 4834 | PDF Full-text (1196 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
The yeast three-hybrid (Y3H) approach shows considerable promise for the unbiased identification of novel small molecule-protein interactions. In recent years, it has been successfully used to link a number of bioactive molecules to novel protein binding partners. However despite its potential importance as
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The yeast three-hybrid (Y3H) approach shows considerable promise for the unbiased identification of novel small molecule-protein interactions. In recent years, it has been successfully used to link a number of bioactive molecules to novel protein binding partners. However despite its potential importance as a protein target identification method, the Y3H technique has not yet been widely adopted, in part due to the challenges associated with the synthesis of the complex chemical inducers of dimerisation (CIDs). The development of a modular approach using potentially “off the shelf” synthetic components was achieved and allowed the synthesis of a family of four triazole-containing CIDs, MTX-Cmpd2.2-2.5. These CIDs were then compared using the Y3H approach with three of them giving a strong positive interaction with a known target of compound 2, TgCDPK1. These results showed that the modular nature of our synthetic strategy may help to overcome the challenges currently encountered with CID synthesis and should contribute to the Y3H approach reaching its full potential as an unbiased target identification strategy. Full article
(This article belongs to the Special Issue Reagents and Methods for Protein Target Identification)
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Open AccessArticle Bioactivity-Guided Fractionation of Physical Fatigue-Attenuating Components from Rubus parvifolius L.
Molecules 2013, 18(9), 11624-11638; https://doi.org/10.3390/molecules180911624
Received: 19 July 2013 / Revised: 25 August 2013 / Accepted: 6 September 2013 / Published: 23 September 2013
Cited by 5 | Viewed by 3018 | PDF Full-text (278 KB) | HTML Full-text | XML Full-text
Abstract
Alleviation of fatigue has been emerging as a serious issue that requires urgent attention. Health professionals and sports physiologists have been looking for active natural products and synthetic compounds to overcome fatigue in humans. This study was designed to define the anti-fatigue property
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Alleviation of fatigue has been emerging as a serious issue that requires urgent attention. Health professionals and sports physiologists have been looking for active natural products and synthetic compounds to overcome fatigue in humans. This study was designed to define the anti-fatigue property of Rubus parvifolius L. (RPL) by characterization of active constituents using a mouse forced swimming test model. Four RPL fractions with different polarities containing anti-fatigue activity were sequentially isolated from the n-butanol RPL extract, followed by elution of 50% ethanol-water fraction from D101 macroporous resin chromatography to obtain nigaichigoside F1, suavissimoside R1 and coreanoside F1. Active constituents of the 50% ethanol-water eluate of RPL were total saponins. The fractions were examined based on the effect on weight-loaded swimming capacity of mice. Serum levels of urea nitrogen (SUN), triglyceride fatty acids (TG), lactate dehydrogenase (LDH), lactic acid (LA), ammonia and hepatic glycogen (HG) were also examined for potential mechanisms underlying the anti-fatigue effect of RPL extracts. During the experiment, two inflammatory markers, interleukin-6 (IL-6) and tumor necrosis factor (TNF-α) in serum, were measured. We found that total saponins from RPL possess potent capabilities to alleviate mouse fatigue induced by forced swimming and that nigaichigoside F1 was responsible for the pharmacological effect. The underlying mechanisms include delays of SUN and LA accumulation, a decrease in TG level by increasing fat consumption, increases in HG and LDH so that lactic acid accumulation and ammonia in the muscle were reduced, and suppression of increased immune activation and inflammatory cytokine production. Our findings will be helpful for functional identification of novel anti-fatigue components from natural medicinal herbs. Full article
(This article belongs to the Section Natural Products Chemistry)
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Open AccessArticle Combined Effects of Green Tea Extracts, Green Tea Polyphenols or Epigallocatechin Gallate with Acarbose on Inhibition against α-Amylase and α-Glucosidase in Vitro
Molecules 2013, 18(9), 11614-11623; https://doi.org/10.3390/molecules180911614
Received: 7 August 2013 / Revised: 13 September 2013 / Accepted: 16 September 2013 / Published: 18 September 2013
Cited by 34 | Viewed by 4702 | PDF Full-text (526 KB) | HTML Full-text | XML Full-text
Abstract
Green tea, green tea polyphenols and epigallocatechin gallate (EGCG) are confirmed to have beneficial effects in the treatment of diabetes mellitus, and a possible mechanism can be ascribed to their inhibitory effect against α-amylase and α-glucosidase in the digestive tract. In this paper,
[...] Read more.
Green tea, green tea polyphenols and epigallocatechin gallate (EGCG) are confirmed to have beneficial effects in the treatment of diabetes mellitus, and a possible mechanism can be ascribed to their inhibitory effect against α-amylase and α-glucosidase in the digestive tract. In this paper, we first investigated the combined inhibitory effect of green tea extracts, green tea polyphenols or EGCG with acarbose on α-amylase and α-glucosidase in vitro. Our results indicated that the interaction between green tea extracts (green tea polyphenols or EGCG) and acarbose was complicated. The combination of green tea extracts, green tea polyphenols or EGCG with acarbose had a synergistic effect on α-amylase and α-glucosidase at low concentrations and the combined effect turned out to be antagonistic at high concentrations according to the Combination Index (CI) values. These findings not only provided some significant quantitative values, but also provide some valuable implications for the combined use of acarbose and GTE (GTP or EGCG) in the treatment of diabetes mellitus. Full article
(This article belongs to the Section Natural Products Chemistry)
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Open AccessArticle Solution Properties and in Vitro Anti-Tumor Activities of Polysaccharides from Longan Pulp
Molecules 2013, 18(9), 11601-11613; https://doi.org/10.3390/molecules180911601
Received: 13 June 2013 / Revised: 28 August 2013 / Accepted: 11 September 2013 / Published: 18 September 2013
Cited by 13 | Viewed by 2840 | PDF Full-text (586 KB) | HTML Full-text | XML Full-text
Abstract
The solution properties of four fractions (LPI–IV) from crude longan pulp polysaccharides (LP3) were analyzed by size-exclusion chromatography combined with laser light scattering, viscometry, complex formation with Congo red, and atomic force microscopy. Their radii of gyration (<S2>z1/2)
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The solution properties of four fractions (LPI–IV) from crude longan pulp polysaccharides (LP3) were analyzed by size-exclusion chromatography combined with laser light scattering, viscometry, complex formation with Congo red, and atomic force microscopy. Their radii of gyration (<S2>z1/2) were 43.3, 62.6, 43.2 and 77.3 nm, exponents of <S2>z1/2 = k Mwv were 0.04, 0.50, 0.52 and 0.02, and intrinsic viscosities ([η]) were 9.945, 25.38, 308.2 and 452.1 mL/g, respectively. Moreover, the dependence of [η] on Mw was established to be [η] = 5.3 × 10−2Mw0.61 (mL/g). LPI had both a sphere-like conformation and a triple-helix structure, and LPII–IV existed as flexible chains. LP3, LPI, LPII and LPIII all exhibited direct inhibitory effects on A549, HeLa and HepG2 cells in a positive dose-dependent manner in the range of 50–400 µg/mL. The activities of LPIII, especially the inhibition of HepG2 cell proliferation, were stronger than those of others, which may be partly related to its flexible conformation. The present results support the cancer therapeutic potential of longan polysaccharides. Full article
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Open AccessReview Plasticity of the Human Olfactory System: The Olfactory Bulb
Molecules 2013, 18(9), 11586-11600; https://doi.org/10.3390/molecules180911586
Received: 15 August 2013 / Revised: 3 September 2013 / Accepted: 11 September 2013 / Published: 17 September 2013
Cited by 40 | Viewed by 4390 | PDF Full-text (1392 KB) | HTML Full-text | XML Full-text
Abstract
In the last years, an increasing interest has been paid to the olfactory system, particularly to its abilities of plasticity and its potential continuous neurogenesis throughout adult life. Although mechanisms underlying adult neurogenesis have been largely investigated in animals, to some degree they
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In the last years, an increasing interest has been paid to the olfactory system, particularly to its abilities of plasticity and its potential continuous neurogenesis throughout adult life. Although mechanisms underlying adult neurogenesis have been largely investigated in animals, to some degree they remain unclear in humans. Based on human research findings, the present review will focus on the olfactory bulb as an evidence of the astonishing plasticity of the human olfactory system. Full article
(This article belongs to the Special Issue Flavors and Fragrances)
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Open AccessArticle Synthesis of a Novel Carbocyclic Analog of Bredinin
Molecules 2013, 18(9), 11576-11585; https://doi.org/10.3390/molecules180911576
Received: 23 August 2013 / Revised: 5 September 2013 / Accepted: 10 September 2013 / Published: 17 September 2013
Cited by 1 | Viewed by 2649 | PDF Full-text (248 KB) | HTML Full-text | XML Full-text
Abstract
The natural nucleoside antibiotic, bredinin, exhibits antiviral and other biological activities. While various nucleosides related to bredinin have been synthesized, its carbocyclic analog has remained unknown. Synthesis of this heretofore unknown analog of bredinin is described. The key precursor, (3aS,4R
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The natural nucleoside antibiotic, bredinin, exhibits antiviral and other biological activities. While various nucleosides related to bredinin have been synthesized, its carbocyclic analog has remained unknown. Synthesis of this heretofore unknown analog of bredinin is described. The key precursor, (3aS,4R,6R,6aR)-6-((methoxy-methoxy)methyl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-amine (5), was prepared from the commercially available compound, (1R,4S)-2-azabicyclo[2.2.1] hept-5-en-3-one (4). Our initial approach used intermediate 6, derived in three transformations from 5, for the key photolytic step to produce the desired ring-opened precursor to the target compound. This photochemical transformation was unsuccessful. However, an appropriately protected and related precursor was synthesized from 5 through the following side-chain functional group transformations: elaboration of the amino group through malonyl ester formation, oximation at the central carbon, conversion of ester to amide and catalytic reduction of the oxime group. This precursor, on treatment with triethylorthoformate and catalytic acetic acid in ethanol, underwent cyclization to produce the desired 4-carbamoyl-imidazolium-5-olate ring. Deprotection of the latter product proceeded smoothly to give the carbocyclic analog of bredinin. This target molecule exhibits antiviral activity, albeit low, against a number of RNA viruses. Further biological evaluations are in progress. Full article
(This article belongs to the Special Issue Synthesis of Nucleosides, Nucleotides and Their Derivatives)
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Open AccessArticle A pH-Sensitive Peptide-Containing Lasso Molecular Switch
Molecules 2013, 18(9), 11553-11575; https://doi.org/10.3390/molecules180911553
Received: 24 July 2013 / Revised: 9 September 2013 / Accepted: 11 September 2013 / Published: 17 September 2013
Cited by 21 | Viewed by 3919 | PDF Full-text (2753 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
The synthesis of a peptide-containing lasso molecular switch by a self-entanglement strategy is described. The interlocked [1] rotaxane molecular machine consists of a benzometaphenylene[25]crown-8 (BMP25C8) macrocycle surrounding a molecular axle. This molecular axle contains a tripeptidic sequence and two molecular stations: a N
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The synthesis of a peptide-containing lasso molecular switch by a self-entanglement strategy is described. The interlocked [1] rotaxane molecular machine consists of a benzometaphenylene[25]crown-8 (BMP25C8) macrocycle surrounding a molecular axle. This molecular axle contains a tripeptidic sequence and two molecular stations: a N-benzyltriazolium and a pH-sensitive anilinium station. The tripeptide is located between the macrocycle and the triazolium station, so that its conformation can be tailored depending on the shuttling of the macrocycle from one station to the other. At acidic pH, the macrocycle resides around the anilinium moiety, whereas it shuttles around the triazolium station after deprotonation. This molecular machinery thus forces the lasso to adopt a tightened or a loosened conformation. Full article
(This article belongs to the Special Issue Rotaxanes)
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Open AccessArticle Analysis of Biotinylated Generation 4 Poly(amidoamine) (PAMAM) Dendrimer Distribution in the Rat Brain and Toxicity in a Cellular Model of the Blood-Brain Barrier
Molecules 2013, 18(9), 11537-11552; https://doi.org/10.3390/molecules180911537
Received: 23 July 2013 / Revised: 3 September 2013 / Accepted: 10 September 2013 / Published: 17 September 2013
Cited by 14 | Viewed by 3672 | PDF Full-text (3257 KB) | HTML Full-text | XML Full-text
Abstract
Dendrimers are highly customizable nanopolymers with qualities that make them ideal for drug delivery. The high binding affinity of biotin/avidin provides a useful approach to fluorescently label synthesized dendrimer-conjugates in cells and tissues. In addition, biotin may facilitate delivery of dendrimers through the
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Dendrimers are highly customizable nanopolymers with qualities that make them ideal for drug delivery. The high binding affinity of biotin/avidin provides a useful approach to fluorescently label synthesized dendrimer-conjugates in cells and tissues. In addition, biotin may facilitate delivery of dendrimers through the blood-brain barrier (BBB) via carrier-mediated endocytosis. The purpose of this research was to: (1) measure toxicity using lactate dehydrogenase (LDH) assays of generation (G)4 biotinylated and non-biotinylated poly(amidoamine) (PAMAM) dendrimers in a co-culture model of the BBB, (2) determine distribution of dendrimers in the rat brain, kidney, and liver following systemic administration of dendrimers, and (3) conduct atomic force microscopy (AFM) on rat brain sections following systemic administration of dendrimers. LDH measurements showed that biotinylated dendrimers were toxic to cell co-culture after 48 h of treatment. Distribution studies showed evidence of biotinylated and non-biotinylated PAMAM dendrimers in brain. AFM studies showed evidence of dendrimers only in brain tissue of treated rats. These results indicate that biotinylation does not decrease toxicity associated with PAMAM dendrimers and that biotinylated PAMAM dendrimers distribute in the brain. Furthermore, this article provides evidence of nanoparticles in brain tissue following systemic administration of nanoparticles supported by both fluorescence microscopy and AFM. Full article
(This article belongs to the Special Issue Dendrimers in Medicine and Biotechnology)
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Open AccessArticle Effect of Tomato Industrial Processing on Phenolic Profile and Antiplatelet Activity
Molecules 2013, 18(9), 11526-11536; https://doi.org/10.3390/molecules180911526
Received: 8 August 2013 / Revised: 12 September 2013 / Accepted: 12 September 2013 / Published: 17 September 2013
Cited by 18 | Viewed by 4152 | PDF Full-text (915 KB) | HTML Full-text | XML Full-text
Abstract
Background: Regular consumption of fruits and vegetables (e.g., tomatoes) has been shown to be beneficial in terms of reducing the incidence of cardiovascular diseases. The industrial processing of tomatoes into tomato-based products includes several thermal treatments. Very little is known on the
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Background: Regular consumption of fruits and vegetables (e.g., tomatoes) has been shown to be beneficial in terms of reducing the incidence of cardiovascular diseases. The industrial processing of tomatoes into tomato-based products includes several thermal treatments. Very little is known on the effect of tomato industrial processing on antiaggregatory activity and phenolic profile. Methods: It was assessed the effect of tomato and by-products extracts on platelet aggregation induced by ADP, collagen, TRAP-6 and arachidonic acid. These in vitro antithrombotic properties were further supported in an in vivo model of thrombosis. A set of antiplatelet compounds has been selected for HPLC analysis in the different extracts. Results: Some natural compounds such as chlorogenic, caffeic, ferulic and p-coumaric acids were identified by HPLC in tomatoes and its products may inhibit platelet activation. Red tomatoes, tomato products (sauce, ketchup and juice) and by-products extracts inhibited platelet aggregation induced adenosine 5'-diphosphate, collagen, thrombin receptor activator peptide-6 and arachidonic acid, but to a different extent. Also, pomace extract presents antithrombotic activity. Conclusions: Processed tomatoes may have a higher content of health-benefiting compounds than fresh ones. Pomace even presents the best antiplatelet activity. Finally, tomato products may be used as a functional ingredient adding antiplatelet activities to processed foods. Full article
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Open AccessArticle Click Reactions as a Key Step for an Efficient and Selective Synthesis of D-Xylose-Based ILs
Molecules 2013, 18(9), 11512-11525; https://doi.org/10.3390/molecules180911512
Received: 27 June 2013 / Revised: 7 August 2013 / Accepted: 10 September 2013 / Published: 17 September 2013
Cited by 7 | Viewed by 2480 | PDF Full-text (456 KB) | HTML Full-text | XML Full-text
Abstract
D-Xylose-based ionic liquids have been prepared from D-xylose following a five steps reaction sequence, the key step being a click cycloaddition. These ionic liquids (ILs) have been characterized through classical analytical methods (IR, NMR, mass spectroscopy, elemental analysis) and their stability constants, Tg
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D-Xylose-based ionic liquids have been prepared from D-xylose following a five steps reaction sequence, the key step being a click cycloaddition. These ionic liquids (ILs) have been characterized through classical analytical methods (IR, NMR, mass spectroscopy, elemental analysis) and their stability constants, Tg and Tdec, were also determined. Considering their properties and their hydrophilicity, these compounds could be alternative solvents for chemical applications under mild conditions. Full article
(This article belongs to the collection Advances in Click Chemistry)
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Open AccessArticle Synthesis and Biological Evaluation of Apigenin Derivatives as Antibacterial and Antiproliferative Agents
Molecules 2013, 18(9), 11496-11511; https://doi.org/10.3390/molecules180911496
Received: 8 July 2013 / Revised: 2 September 2013 / Accepted: 12 September 2013 / Published: 17 September 2013
Cited by 18 | Viewed by 3436 | PDF Full-text (266 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Two series of apigenin [5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one] derivatives, 3a3j and 4a4j, were synthesized. The apigenin and alkyl amines moieties of these compounds were separated by C2 or C3 spacers, respectively. The chemical structures of the apigenin derivatives were
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Two series of apigenin [5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one] derivatives, 3a3j and 4a4j, were synthesized. The apigenin and alkyl amines moieties of these compounds were separated by C2 or C3 spacers, respectively. The chemical structures of the apigenin derivatives were confirmed using 1H-NMR, 13C-NMR, and electrospray ionization mass spectroscopy. The in vitro antibacterial and antiproliferative activities of all synthesized compounds were determined. Among the tested compounds, 4a4j displayed significant antibacterial activity against the tested strains (Staphylococcus aureus, Bacillus subtilis, Escherichia coli, and Pseudomonas aeruginosa). Additionally, 4i showed the best inhibitory activity with minimum inhibitory concentrations of 1.95, 3.91, 3.91, and 3.91 μg/mL against S. aureus, B. subtilis, E. coli, and P. aeruginosa, respectively. The antiproliferative activity of the apigenin derivatives was evaluated by an MTT [3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide] assay. We determined that 4a4j displayed better growth inhibition activity against four human cancer cell lines, namely, human lung (A549), human cervical (HeLa), human hepatocellular liver (HepG2), and human breast (MCF-7) cancer cells, than the parent apigenin. Compound 4j was found to be the most active antiproliferative compound against the selected cancer cells. Structure-activity relationships were also discussed based on the obtained experimental data. Full article
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Open AccessArticle Fremy’s Salt-Mediated Oxidative Addition. A New Approach in the Total Synthesis of Naturally Dipetalolactone and Its Immunomodulatory Activity
Molecules 2013, 18(9), 11485-11495; https://doi.org/10.3390/molecules180911485
Received: 2 July 2013 / Revised: 30 July 2013 / Accepted: 26 August 2013 / Published: 16 September 2013
Cited by 1 | Viewed by 2409 | PDF Full-text (250 KB) | HTML Full-text | XML Full-text
Abstract
The structure of the natural dipyranocoumarin dipetalolactone has been confirmed by an unambiguous synthetic route from resorcinol. This sequence was initiated by a pyran ring formation step which introduced the 3-chloro-3-methylbut-1-yne moiety. Then, the expected product undergoes a Fremy’s salt-meditated oxidative addition followed
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The structure of the natural dipyranocoumarin dipetalolactone has been confirmed by an unambiguous synthetic route from resorcinol. This sequence was initiated by a pyran ring formation step which introduced the 3-chloro-3-methylbut-1-yne moiety. Then, the expected product undergoes a Fremy’s salt-meditated oxidative addition followed by ring closure to yield dipetalolactone. Dipetalolactone was also found to have immunological activity in a mouse carcinoma S180-bearing mice cell line. Full article
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Open AccessArticle Probing the Residual Structure in Avian Prion Hexarepeats by CD, NMR and MD Techniques
Molecules 2013, 18(9), 11467-11484; https://doi.org/10.3390/molecules180911467
Received: 5 August 2013 / Revised: 3 September 2013 / Accepted: 9 September 2013 / Published: 16 September 2013
Cited by 4 | Viewed by 2612 | PDF Full-text (907 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Many proteins perform essential biological functions by means of regions that lacking specific organized structure exist as an ensemble of interconverting transient conformers. The characterization of such regions, including the description of their structural propensities, number of conformations and relative populations can provide
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Many proteins perform essential biological functions by means of regions that lacking specific organized structure exist as an ensemble of interconverting transient conformers. The characterization of such regions, including the description of their structural propensities, number of conformations and relative populations can provide useful insights. Prion diseases result from the conversion of a normal glycoprotein into a misfolded pathogenic isoform. The structures of mammal and chicken prion proteins show a similar fold with a globular domain and a flexible N-terminal portion that contains different repeated regions: octarepeats (PHGGGWGQ) in mammals and hexarepeats (PHNPGY) in chickens. The higher number of prolines in the hexarepeat region suggests that this region may retain a significant amount of residual secondary structure. Here, we report the CD, NMR and MD characterization of a peptide (2-HexaPY) composed of two hexarepeats. We combine experimental NMR data and MD to investigate at atomic level its ensemble-averaged structural properties, demonstrating how each residue of both repeats has a different quantified PPII propensity that shows a periodicity along the sequence. This feature explains the absence of cooperativity to stabilize a PPII conformation. Nonetheless, such residual structure can play a role in nucleating local structural transitions as well as modulating intra-molecular or inter-molecular interactions. Full article
(This article belongs to the Special Issue NMR of Proteins and Small Biomolecules)
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Open AccessArticle Determination and Pharmacokinetics of Di-(2-ethylhexyl) Phthalate in Rats by Ultra Performance Liquid Chromatography with Tandem Mass Spectrometry
Molecules 2013, 18(9), 11452-11466; https://doi.org/10.3390/molecules180911452
Received: 22 July 2013 / Revised: 1 September 2013 / Accepted: 13 September 2013 / Published: 16 September 2013
Cited by 7 | Viewed by 3317 | PDF Full-text (1235 KB) | HTML Full-text | XML Full-text
Abstract
Di-(2-ethylhexyl) phthalate (DEHP) is used to increase the flexibility of plastics for industrial products. However, the illegal use of the plasticizer DEHP in food and drinks has been reported in Taiwan in 2011. In order to assess the exact extent of the absorption
[...] Read more.
Di-(2-ethylhexyl) phthalate (DEHP) is used to increase the flexibility of plastics for industrial products. However, the illegal use of the plasticizer DEHP in food and drinks has been reported in Taiwan in 2011. In order to assess the exact extent of the absorption of DEHP via the oral route, the aim of this study is to develop a reliable and validated ultra performance liquid chromatography with tandem mass spectrometry (UPLC-MS/MS) method to evaluate the oral bioavailability of DEHP in rats. The optimal chromatographic separation of DEHP and butyl benzyl phthalate (BBP; used as internal standard) were achieved on a C18 column. The mobile phase was consisted of 5 mM ammonium acetate-methanol (11:89, v/v) with a flow rate of 0.25 mL/min. The monitoring ion transitions were m/z 391.4 → 149.0 for DEHP and m/z 313.3 → 149.0 for BBP. The mean matrix effects of DEHP at low, medium and high concentrations were 94.5 ± 5.7% and 100.1 ± 2.3% in plasma and feces homogenate samples, respectively. In conclusion, the validated UPLC-MS/MS method is suitable for analyzing the rat plasma sample of DEHP and the oral bioavailability of DEHP was about 7% in rats. Full article
(This article belongs to the Section Metabolites)
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Open AccessArticle Harvestman Phenols and Benzoquinones: Characterisation and Biosynthetic Pathway
Molecules 2013, 18(9), 11429-11451; https://doi.org/10.3390/molecules180911429
Received: 19 July 2013 / Revised: 5 September 2013 / Accepted: 6 September 2013 / Published: 16 September 2013
Cited by 16 | Viewed by 2615 | PDF Full-text (1006 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Benzoquinones are usually present in arthropod defence exudates. Here, we describe the chemical profiles of 12 harvestman species belonging to the neotropical family Gonyleptidae. Nine of the studied species produced benzoquinones, while three produced alkyl phenols. Two benzoquinones and one phenol exhibited biological
[...] Read more.
Benzoquinones are usually present in arthropod defence exudates. Here, we describe the chemical profiles of 12 harvestman species belonging to the neotropical family Gonyleptidae. Nine of the studied species produced benzoquinones, while three produced alkyl phenols. Two benzoquinones and one phenol exhibited biological activity against bacteria and fungi. We also studied the biosynthesis of 2-ethyl-1,4-benzoquinone by feeding Magnispina neptunus individuals with 13C-labelled precursors; the benzoquinones were biosynthesised through a polyketide pathway using acetate and propionate building blocks. Full article
(This article belongs to the Section Natural Products Chemistry)
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Open AccessReview Oxetane Synthesis through the Paternò-Büchi Reaction
Molecules 2013, 18(9), 11384-11428; https://doi.org/10.3390/molecules180911384
Received: 29 July 2013 / Revised: 5 September 2013 / Accepted: 10 September 2013 / Published: 16 September 2013
Cited by 30 | Viewed by 3965 | PDF Full-text (412 KB) | HTML Full-text | XML Full-text
Abstract
The Paternò-Büchi reaction is a photochemical reaction between a carbonyl compound and an alkene to give the corresponding oxetane. In this review the mechanism of the reaction is discussed. On this basis the described use in the reaction with electron rich alkenes (enolethers,
[...] Read more.
The Paternò-Büchi reaction is a photochemical reaction between a carbonyl compound and an alkene to give the corresponding oxetane. In this review the mechanism of the reaction is discussed. On this basis the described use in the reaction with electron rich alkenes (enolethers, enol esters, enol silyl ethers, enanines, heterocyclic compounds has been reported. The stereochemical behavior of the reaction is particularly stressed. We pointed out the reported applications of this reaction to the synthesis of naturally occuring compounds. Full article
(This article belongs to the Special Issue Named Organic Reactions based on Italian Chemists)
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Open AccessLetter A New Lignan Glucoside from the Whole Plants of Salvia Scapiformis
Molecules 2013, 18(9), 11377-11383; https://doi.org/10.3390/molecules180911377
Received: 30 August 2013 / Revised: 6 September 2013 / Accepted: 9 September 2013 / Published: 13 September 2013
Cited by 4 | Viewed by 2730 | PDF Full-text (467 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Phytochemical investigation of the whole plants of Salvia scapiformis Hance afforded eight compounds, including one new lignan, (+)-8α-hydroxypinoresinol-8-O-[6′′-O-(4′′′-hydroxybenzoyl)]-β-d-glucopyranoside (1), four known lignans, (+)-8α-hydroxy-pinoresinol-8-O-β-d-glucopyranoside (2), (+)-8
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Phytochemical investigation of the whole plants of Salvia scapiformis Hance afforded eight compounds, including one new lignan, (+)-8α-hydroxypinoresinol-8-O-[6′′-O-(4′′′-hydroxybenzoyl)]-β-d-glucopyranoside (1), four known lignans, (+)-8α-hydroxy-pinoresinol-8-O-β-d-glucopyranoside (2), (+)-8α-hydroxypinoresinol (3), (+)-pinoresinol (4), and (+)-medioresinol (5), and three known triterpenoids, ursolic acid (6), 4-epi-niga-ichigoside F1 (7), and niga-ichigoside F1 (8). Their structures were determined on the basis of extensive spectroscopic analyses and comparison with spectroscopic data in the literature. The absolute configuration of the new compound 1 was determined by chemical transformation and GC analysis. Full article
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Open AccessReview Anticancer and Antifungal Compounds from Aspergillus, Penicillium and Other Filamentous Fungi
Molecules 2013, 18(9), 11338-11376; https://doi.org/10.3390/molecules180911338
Received: 3 July 2013 / Revised: 23 August 2013 / Accepted: 3 September 2013 / Published: 13 September 2013
Cited by 38 | Viewed by 4870 | PDF Full-text (490 KB) | HTML Full-text | XML Full-text
Abstract
This review covers important anticancer and antifungal compounds reported from filamentous fungi and in particular from Aspergillus, Penicillium and Talaromyces. The taxonomy of these fungi is not trivial, so a focus of this review has been to report the correct identity
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This review covers important anticancer and antifungal compounds reported from filamentous fungi and in particular from Aspergillus, Penicillium and Talaromyces. The taxonomy of these fungi is not trivial, so a focus of this review has been to report the correct identity of the producing organisms based on substantial previous in-house chemotaxonomic studies. Full article
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Open AccessArticle Dillapiole, Isolated from Peperomia pellucida, Shows Gastroprotector Activity against Ethanol-Induced Gastric Lesions in Wistar Rats
Molecules 2013, 18(9), 11327-11337; https://doi.org/10.3390/molecules180911327
Received: 15 July 2013 / Revised: 4 September 2013 / Accepted: 10 September 2013 / Published: 13 September 2013
Cited by 14 | Viewed by 3183 | PDF Full-text (221 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Peperomia pellucida is a plant used in traditional medicine to treat gastric ulcers. Although this gastroprotective activity was reported, the active compounds have not been identified. Therefore, the aim herein was to identify the most active compound in the gastroprotective activity of P.
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Peperomia pellucida is a plant used in traditional medicine to treat gastric ulcers. Although this gastroprotective activity was reported, the active compounds have not been identified. Therefore, the aim herein was to identify the most active compound in the gastroprotective activity of P. pellucida using an ethanol-induced gastric ulcer experimental rat model. A gastroprotective effect was observed when the hexane and dichloromethane extracts were tested, with the higher effect being obtained with the dichloromethane extract (82.3 ± 5.6%) at 100 mg/kg. Dillapiole was identified as the most active compound in this extract. Although there have been previous reports on dillapiole, this is the first on its gastroprotective activity. Rats treated with this compound at 3, 10, 30 and 100 mg/kg showed 23.1, 56.1, 73.2 and 85.5% gastroprotection, respectively. The effect elicited by dillapiole at 100 mg/kg was not attenuated by pretreatment with indomethacin (10 mg/kg, s.c.), a prostaglandin synthesis blocker, NG-nitro-l-arginine methyl ester (70 mg/kg, i.p.), a nitric oxide (NO) synthase inhibitor, or N-ethylmaleimide (10 mg/kg, s.c.), a blocker of sulfhydryl groups. This suggests that the gastroprotective mechanism of action of dillapiole does not involve prostaglandins, NO or sulfhydryl groups. Full article
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Open AccessReview Revealing the Properties of Plant Defensins through Dynamics
Molecules 2013, 18(9), 11311-11326; https://doi.org/10.3390/molecules180911311
Received: 17 July 2013 / Revised: 7 September 2013 / Accepted: 10 September 2013 / Published: 13 September 2013
Cited by 10 | Viewed by 2754 | PDF Full-text (2050 KB) | HTML Full-text | XML Full-text
Abstract
Defensins are potent, ancient natural antibiotics that are present in organisms ranging from lower organisms to humans. Although the structures of several defensins have been well characterized, the dynamics of only a few have been studied. This review discusses the diverse dynamics of
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Defensins are potent, ancient natural antibiotics that are present in organisms ranging from lower organisms to humans. Although the structures of several defensins have been well characterized, the dynamics of only a few have been studied. This review discusses the diverse dynamics of two plant defensins for which the structure and dynamics have been characterized, both in the free state and in the presence of target membranes. Multiple motions are observed in loops and in secondary structure elements and may be related to twisting or breathing of the α-helix and β-sheet. This complex behavior is altered in the presence of an interface and is responsive to the presence of the putative target. The stages of membrane recognition and disruption can be mapped over a large time scale range, demonstrating that defensins in solution exist as an ensemble of different conformations, a subset of which is selected upon membrane binding. Therefore, studies on the dynamics have revealed that defensins interact with membranes through a mechanism of conformational selection. Full article
(This article belongs to the Special Issue NMR of Proteins and Small Biomolecules)
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Open AccessArticle Isolation and Identification of Two Novel Attractant Compounds from Chinese Cockroach (Eupolyphaga sinensis Walker) by Combination of HSCCC, NMR and CD Techniques
Molecules 2013, 18(9), 11299-11310; https://doi.org/10.3390/molecules180911299
Received: 5 August 2013 / Revised: 6 September 2013 / Accepted: 6 September 2013 / Published: 13 September 2013
Cited by 2 | Viewed by 2983 | PDF Full-text (234 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
High-speed counter-current chromatography (HSCCC) with a two-phase solvent system composed of n-hextane-ethyl acetate-methanol-water (1.5:1:1.5:1, v/v/v/v) was applied to the isolation and purification of attractants from Chinese cockroach, Eupolyphaga sinensis Walker. Two new attractants with attractant activity towards the male insects were
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High-speed counter-current chromatography (HSCCC) with a two-phase solvent system composed of n-hextane-ethyl acetate-methanol-water (1.5:1:1.5:1, v/v/v/v) was applied to the isolation and purification of attractants from Chinese cockroach, Eupolyphaga sinensis Walker. Two new attractants with attractant activity towards the male insects were obtained from the extract sample in a one-step separation. Their purities were determined by HPLC. Subsequent MS, NMR and CD analyses have led to the characterization of (R)-3-ethyl-6,8-dihydroxy-7-methyl-3,4-dihydroisochromen-1-one (1) and (R)-6,8-dihydroxy-3,7-dimethyl-3,4-dihydroisochromen-1-one (2), two novel isocumarin type attractants. Based on these results, it is concluded that HSCCC is a viable separation method option for purifying insect attractants, while effectively maintaining the attracting activity of the isolates. This is the first attempt to apply counter-current chromatography technique to separate attractants from Chinese cockroach. Full article
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Open AccessArticle Identification of Multiple Ingredients for a Traditional Chinese Medicine Preparation (Bu-yang-huan-wu-tang) by Liquid Chromatography Coupled with Tandem Mass Spectrometry
Molecules 2013, 18(9), 11281-11298; https://doi.org/10.3390/molecules180911281
Received: 19 July 2013 / Revised: 5 September 2013 / Accepted: 10 September 2013 / Published: 12 September 2013
Cited by 14 | Viewed by 4078 | PDF Full-text (1076 KB) | HTML Full-text | XML Full-text
Abstract
Bu-yang-huan-wu-tang (BYHWT) is a popular Traditional Chinese Medicine formula consisting of seven herbal medicines (Astragalus membranaceus, Angelica sinensis, Paeonia lactiflora, Ligusticum chuanxiong, Carthamus tinctorius, Amygdalus persica and Pheretima aspergillum), that has been used in China for centuries to overcome stroke-induced disability. To ensure
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Bu-yang-huan-wu-tang (BYHWT) is a popular Traditional Chinese Medicine formula consisting of seven herbal medicines (Astragalus membranaceus, Angelica sinensis, Paeonia lactiflora, Ligusticum chuanxiong, Carthamus tinctorius, Amygdalus persica and Pheretima aspergillum), that has been used in China for centuries to overcome stroke-induced disability. To ensure the consistency of quality, a reliable analytical method is required, therefore, we developed a liquid chromatography with tandem mass spectrometry (LC-MS/MS) method for quantitative analysis of the major constituents in BYHWT. The herbal ingredients consisting of the cycloartane-type triterpene glycosides of astragaloside I, astragaloside II and astragaloside IV; isoflavones of formononetin, ononin calycosin, calycosin-7-O-β-d-glucoside; ligustilide and paeoniflorin were separated on a C18 column with gradient elution of methanol/10 mM ammonium acetate buffer–formic acid (100:0.1, v/v). This study was performed by a mass spectrometer using electrospray ionization (ESI) with positive ionization ions monitored in the multiple reaction-monitoring (MRM) mode. The linearity, accuracy, precision, limit of detection (LOD) and lower limit of quantification (LLOQ) were validated for this quantification method, and the sensitivity, reliability and reproducibility were all confirmed. The experiments provided a good method for analyzing BYHWT extracts. This study also quantitated the active components in various brands of commercially available products. The results indicated that the pharmaceutical industrial products of BYHWT exhibited considerable variation in their contents of the herbal compounds. Full article
(This article belongs to the Section Natural Products Chemistry)
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Open AccessArticle Anti-Peroxyl Radical Quality and Antibacterial Properties of Rooibos Infusions and Their Pure Glycosylated Polyphenolic Constituents
Molecules 2013, 18(9), 11264-11280; https://doi.org/10.3390/molecules180911264
Received: 26 July 2013 / Revised: 3 September 2013 / Accepted: 9 September 2013 / Published: 12 September 2013
Cited by 9 | Viewed by 3554 | PDF Full-text (1002 KB) | HTML Full-text | XML Full-text
Abstract
The anti-peroxyl radical quality of two aqueous rooibos infusions and solutions of their most abundant glycosylated polyphenols was evaluated using pyrogallol red and fluorescein-based oxygen radical absorbance ratios. It was observed that the artificial infusions, prepared using only the most abundant polyphenols present
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The anti-peroxyl radical quality of two aqueous rooibos infusions and solutions of their most abundant glycosylated polyphenols was evaluated using pyrogallol red and fluorescein-based oxygen radical absorbance ratios. It was observed that the artificial infusions, prepared using only the most abundant polyphenols present in rooibos and at concentrations similar to those found in the natural infusions, showed greater antioxidant quality than the latter infusions, reaching values close to those reported for tea infusions. Additionally, the antimicrobial activity of the natural and artificial infusions was assessed against three species of bacteria: Gram (+) Staphylococus epidermidis and Staphylococcus aureus and Gram (−) Escherichia coli. When compared to the natural infusions the artificial beverages did not demonstrate any bacterostatic/cidal activity, suggesting that the antibacterial activity of rooibos is related to compounds other than the glycosylated polyphenols employed in our study. Full article
(This article belongs to the Section Natural Products Chemistry)
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Open AccessArticle Design and Synthesis of N1,N5-bis[4-(5-Alkyl-1,2,4-oxadiazol-3-yl)phenyl]glutaramides as Potential Antifungal Prodrugs
Molecules 2013, 18(9), 11250-11263; https://doi.org/10.3390/molecules180911250
Received: 29 July 2013 / Revised: 4 September 2013 / Accepted: 10 September 2013 / Published: 12 September 2013
Cited by 6 | Viewed by 2508 | PDF Full-text (494 KB) | HTML Full-text | XML Full-text
Abstract
A facile three step synthesis of a group of N1,N5-bis[4-(5-alkyl-1,2,4-oxadiazol-3-yl)phenyl]glutaramides, N1,N5-bis[4-(1,2,4-oxadiazol-3-yl)phenyl]glutaramide and N1,N5-bis[4-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)phenyl]glutaramide is described. These products are designed to function as masked bis-amidine prodrugs of a promising N1,N5-bis[4-(N'-(carbamimidoyl)phenyl]glutaramide antifungal lead. Full article
(This article belongs to the Special Issue Advances in Medicinal Chemistry of Antifungals)
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Open AccessArticle Two New Sphingolipids from the Leaves of Piper betle L.
Molecules 2013, 18(9), 11241-11249; https://doi.org/10.3390/molecules180911241
Received: 14 July 2013 / Revised: 4 September 2013 / Accepted: 5 September 2013 / Published: 12 September 2013
Cited by 4 | Viewed by 2525 | PDF Full-text (214 KB) | HTML Full-text | XML Full-text
Abstract
Two new sphingolipids, pipercerebrosides A (1) and B (2), were isolated from the leaves of Piper betle L. Their structures, including absolute configurations, were determined by spectroscopic analysis and chemical degradation. These two compounds did not show significant cytotoxic
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Two new sphingolipids, pipercerebrosides A (1) and B (2), were isolated from the leaves of Piper betle L. Their structures, including absolute configurations, were determined by spectroscopic analysis and chemical degradation. These two compounds did not show significant cytotoxic activity against the cancer cell lines K562 and HL-60 in a MTT assay. Full article
(This article belongs to the Section Natural Products Chemistry)
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Open AccessArticle Thymoquinone Induces Mitochondria-Mediated Apoptosis in Acute Lymphoblastic Leukaemia in Vitro
Molecules 2013, 18(9), 11219-11240; https://doi.org/10.3390/molecules180911219
Received: 18 July 2013 / Revised: 25 August 2013 / Accepted: 30 August 2013 / Published: 12 September 2013
Cited by 29 | Viewed by 10318 | PDF Full-text (1807 KB) | HTML Full-text | XML Full-text
Abstract
There has been a growing interest in naturally occurring compounds from traditional medicine with anti-cancer potential. Nigella sativa (black seed) is one of the most widely studied plants. This annual herb grows in countries bordering the Mediterranean Sea and India. Thymoquinone (TQ) is
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There has been a growing interest in naturally occurring compounds from traditional medicine with anti-cancer potential. Nigella sativa (black seed) is one of the most widely studied plants. This annual herb grows in countries bordering the Mediterranean Sea and India. Thymoquinone (TQ) is an active ingredient isolated from Nigella sativa. The anti-cancer effect of TQ, via the induction of apoptosis resulting from mitochondrial dysfunction, was assessed in an acute lymphocyte leukemic cell line (CEMss) with an IC50 of 1.5 µg/mL. A significant increase in chromatin condensation in the cell nucleus was observed using fluorescence analysis. The apoptosis was then confirmed by Annexin V and an increased number of cellular DNA breaks in treated cells were observed as a DNA ladder. Treatment of CEMss cells with TQ encouraged apoptosis with cell death-transducing signals by a down-regulation of Bcl-2 and up-regulation of Bax. Moreover, the significant generation of cellular ROS, HSP70 and activation of caspases 3 and 8 were also observed in the treated cells. The mitochondrial apoptosis was clearly associated with the S phase cell cycle arrest. In conclusion, the results from the current study indicated that TQ could be a promising agent for the treatment of leukemia. Full article
(This article belongs to the Section Natural Products Chemistry)
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Open AccessArticle Synthesis of a-O- and a-S-Glycosphingolipids Related to Sphingomonous cell Wall Antigens Using Anomerisation
Molecules 2013, 18(9), 11198-11218; https://doi.org/10.3390/molecules180911198
Received: 31 July 2013 / Revised: 4 September 2013 / Accepted: 5 September 2013 / Published: 12 September 2013
Cited by 8 | Viewed by 2923 | PDF Full-text (560 KB) | HTML Full-text | XML Full-text
Abstract
Analogues of glycolipids from Spingomonadacaece with O- and S- and SO2-linkages have been prepared using chelation induced anomerisation promoted by TiCl4. Included are examples of the anomerisation of intermediates with O- and S-glycosidic linkages as
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Analogues of glycolipids from Spingomonadacaece with O- and S- and SO2-linkages have been prepared using chelation induced anomerisation promoted by TiCl4. Included are examples of the anomerisation of intermediates with O- and S-glycosidic linkages as well as isomerisation of β-thioglycuronic acids (β-glycosyl thiols). The β-O-glucuronide and β-O-galacturonide precursors were efficiently prepared using benzoylated trichloroacetimidates. β-Glycosyl thiols were precursors to β-S-derivatives. Triazole containing mimics of the natural glycolipids were prepared using CuI promoted azide-alkyne cycloaddition reactions in THF. The glycolipid antigens are being evaluated currently for their effects on iNKT cells. Full article
(This article belongs to the Special Issue Synthesis, Structure, Analysis and Properties of Glycolipids)
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Open AccessReview Metal Complexes of Quinolone Antibiotics and Their Applications: An Update
Molecules 2013, 18(9), 11153-11197; https://doi.org/10.3390/molecules180911153
Received: 8 August 2013 / Revised: 2 September 2013 / Accepted: 2 September 2013 / Published: 11 September 2013
Cited by 95 | Viewed by 5609 | PDF Full-text (447 KB) | HTML Full-text | XML Full-text
Abstract
Quinolones are synthetic broad-spectrum antibiotics with good oral absorption and excellent bioavailability. Due to the chemical functions found on their nucleus (a carboxylic acid function at the 3-position, and in most cases a basic piperazinyl ring (or another N-heterocycle) at the 7-position, and
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Quinolones are synthetic broad-spectrum antibiotics with good oral absorption and excellent bioavailability. Due to the chemical functions found on their nucleus (a carboxylic acid function at the 3-position, and in most cases a basic piperazinyl ring (or another N-heterocycle) at the 7-position, and a carbonyl oxygen atom at the 4-position) quinolones bind metal ions forming complexes in which they can act as bidentate, as unidentate and as bridging ligand, respectively. In the polymeric complexes in solid state, multiple modes of coordination are simultaneously possible. In strongly acidic conditions, quinolone molecules possessing a basic side nucleus are protonated and appear as cations in the ionic complexes. Interaction with metal ions has some important consequences for the solubility, pharmacokinetics and bioavailability of quinolones, and is also involved in the mechanism of action of these bactericidal agents. Many metal complexes with equal or enhanced antimicrobial activity compared to the parent quinolones were obtained. New strategies in the design of metal complexes of quinolones have led to compounds with anticancer activity. Analytical applications of complexation with metal ions were oriented toward two main directions: determination of quinolones based on complexation with metal ions or, reversely, determination of metal ions based on complexation with quinolones. Full article
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Open AccessArticle An Efficient Synthesis of Enantiopure (R)-heteroarylpyrimidine Analogs
Molecules 2013, 18(9), 11144-11152; https://doi.org/10.3390/molecules180911144
Received: 23 August 2013 / Revised: 3 September 2013 / Accepted: 4 September 2013 / Published: 11 September 2013
Cited by 1 | Viewed by 2475 | PDF Full-text (333 KB) | HTML Full-text | XML Full-text
Abstract
An efficient synthesis of enantiopure (R)-heteroarylpyrimidine analogs is described here, which involves introduction of a chiral group, formation and separation of diasteroisomers and final transformation of an amide to an ester. The absolute configuration of the enantiopure HAPs is confirmed by
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An efficient synthesis of enantiopure (R)-heteroarylpyrimidine analogs is described here, which involves introduction of a chiral group, formation and separation of diasteroisomers and final transformation of an amide to an ester. The absolute configuration of the enantiopure HAPs is confirmed by X-ray analysis of their intermediates. Full article
(This article belongs to the Section Medicinal Chemistry)
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Open AccessArticle In Vivo and in Vitro Effects of Secondary Metabolites against Xanthomonas campestris pv. campestris
Molecules 2013, 18(9), 11131-11143; https://doi.org/10.3390/molecules180911131
Received: 13 August 2013 / Revised: 6 September 2013 / Accepted: 9 September 2013 / Published: 11 September 2013
Cited by 8 | Viewed by 3093 | PDF Full-text (491 KB) | HTML Full-text | XML Full-text
Abstract
Brassica rapa is a crucifer that is grown worldwide, mainly as a vegetable. The quality of B. rapa crops is highly affected by the disease caused by the bacteria Xanthomonas campestris pv. campestris (Xcc). Glucosinolates and phenolic compounds can confer resistance to
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Brassica rapa is a crucifer that is grown worldwide, mainly as a vegetable. The quality of B. rapa crops is highly affected by the disease caused by the bacteria Xanthomonas campestris pv. campestris (Xcc). Glucosinolates and phenolic compounds can confer resistance to Brassica crops against pests and diseases, but few works have been done to evaluate their role in Xcc resistance. The objectives of this work were: (1) to evaluate the in vivo and in vitro antibacterial effect of gluconapin, its isothiocyanate and the methanolic extracts of B. rapa against the type 4 of Xcc, and (2) to test if there is induced resistance mediated by glucosinolates or phenolic compounds in two varieties of B. rapa. Gluconapin and its ITC varieties had an antibacterial effect on the development of Xanthomonas and this effect was strongly dependent on the concentration applied. Methanolic extracts from B. rapa, containing glucosinolates and phenolic compounds, inhibited the growth of these bacteria. Concentration of gluconapin is higher in resistant plants than in the susceptible ones and there is an induction of gluconapin, some flavonoids and sinapic acid 48 to 72 h after inoculation. Gluconapin plays a role in the constitutive resistance to Xcc, while gluconapin, some flavonoids and hydroxycinnamic acids are induced by a Xcc infection but it is not clear if this induction confers resistance to this disease. Full article
(This article belongs to the Section Metabolites)
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