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Molecules, Volume 16, Issue 3 (March 2011) – 57 articles , Pages 1917-2742

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216 KiB  
Review
Essential Oils and Their Constituents: Anticonvulsant Activity
by Reinaldo Nóbrega de Almeida, Maria de Fátima Agra, Flávia Negromonte Souto Maior and Damião Pergentino De Sousa
Molecules 2011, 16(3), 2726-2742; https://doi.org/10.3390/molecules16032726 - 23 Mar 2011
Cited by 105 | Viewed by 12912
Abstract
A literature-based survey of plants species and their essential oils with anticonvulsant activity was carried out. As results, 30 species belonging to 13 families and 23 genera were identified for their activities in the experimental models used for anticonvulsant drug screening. Thirty chemical [...] Read more.
A literature-based survey of plants species and their essential oils with anticonvulsant activity was carried out. As results, 30 species belonging to 13 families and 23 genera were identified for their activities in the experimental models used for anticonvulsant drug screening. Thirty chemical constituents of essential oils with anticonvulsant properties were described. Information on these 30 species is presented together with isolated bioactive compound studies. Full article
(This article belongs to the Special Issue Neuroactive Compounds)
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294 KiB  
Article
Oxidative Decarboxylation of Levulinic Acid by Silver(I)/Persulfate
by Yan Gong and Lu Lin
Molecules 2011, 16(3), 2714-2725; https://doi.org/10.3390/molecules16032714 - 23 Mar 2011
Cited by 34 | Viewed by 9811
Abstract
The oxidative decarboxylation of levulinic acid (LA) by silver(I)/persulfate [Ag(I)/S2O82−] has been investigated in this paper. The effects of buffer solution, initial pH value, time and temperature and dosages of Ag(I)/S2O82− on the decarboxylation [...] Read more.
The oxidative decarboxylation of levulinic acid (LA) by silver(I)/persulfate [Ag(I)/S2O82−] has been investigated in this paper. The effects of buffer solution, initial pH value, time and temperature and dosages of Ag(I)/S2O82− on the decarboxylation of LA were examined in batch experiments and a reaction scheme was proposed on basis of the reaction process. The experimental results showed that a solution of NaOH-KH2PO4 was comparatively suitable for the LA decarboxylation reaction by silver(I)/persulfate. Under optimum conditions (temperature 160 °C, pH 5.0, and time 0.5 h), the rate of LA conversion in NaOH-KH2PO4 solutions with an initial concentration of 0.01 mol LA reached 70.2%, 2-butanone (methyl ethyl ketone) was the single product in the gas phase and the resulted molar yield reached 44.2%. Full article
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487 KiB  
Review
Glycosides, Depression and Suicidal Behaviour: The Role of Glycoside-Linked Proteins
by Gianluca Serafini, Maurizio Pompili, Marco Innamorati, Gloria Giordano, Roberto Tatarelli, David Lester, Paolo Girardi and Yogesh Dwivedi
Molecules 2011, 16(3), 2688-2713; https://doi.org/10.3390/molecules16032688 - 23 Mar 2011
Cited by 12 | Viewed by 9993
Abstract
Nowadays depression and suicide are two of the most important worldwide public health problems. Although their specific molecular mechanisms are still largely unknown, glycosides can play a fundamental role in their pathogenesis. These molecules act presumably through the up-regulation of plasticity-related proteins: probably [...] Read more.
Nowadays depression and suicide are two of the most important worldwide public health problems. Although their specific molecular mechanisms are still largely unknown, glycosides can play a fundamental role in their pathogenesis. These molecules act presumably through the up-regulation of plasticity-related proteins: probably they can have a presynaptic facilitatory effect, through the activation of several intracellular signaling pathways that include molecules like protein kinase A, Rap-1, cAMP, cADPR and G proteins. These proteins take part in a myriad of brain functions such as cell survival and synaptic plasticity. In depressed suicide victims, it has been found that their activity is strongly decreased, primarily in hippocampus and prefrontal cortex. These studies suggest that glycosides can regulate neuroprotection through Rap-1 and other molecules, and may play a crucial role in the pathophysiology of depression and suicide. Full article
(This article belongs to the Special Issue Glycosides)
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701 KiB  
Review
Challenges and Perspectives of Chemical Biology, a Successful Multidisciplinary Field of Natural Sciences
by Fernando A. Rojas-Ruiz, Leonor Y. Vargas-Méndez and Vladimir V. Kouznetsov
Molecules 2011, 16(3), 2672-2687; https://doi.org/10.3390/molecules16032672 - 23 Mar 2011
Cited by 5 | Viewed by 11633
Abstract
Objects, goals, and main methods as well as perspectives of chemical biology are discussed. This review is focused on the fundamental aspects of this emerging field of life sciences: chemical space, the small molecule library and chemical sensibilization (small molecule microassays). Full article
(This article belongs to the Special Issue Diversity Oriented Synthesis)
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370 KiB  
Article
Investigation of Solvolysis Kinetics of New Synthesized Fluocinolone Acetonide C-21 Esters—An In Vitro Model for Prodrug Activation
by Bojan D. Markovic, Vladimir D. Dobricic, Sote M. Vladimirov, Olivera A. Cudina, Vladimir M. Savic and Katarina D. Karljikovic-Rajic
Molecules 2011, 16(3), 2658-2671; https://doi.org/10.3390/molecules16032658 - 23 Mar 2011
Cited by 11 | Viewed by 9853
Abstract
In this study the solvolysis of newly synthesized fluocinolone acetonide C-21 esters was analysed in comparison with fluocinonide during a 24-hour period of time. The solvolysis was performed in an ethanol-water (90:10 v/v) mixture using the excess of NaHCO3. The solvolytic [...] Read more.
In this study the solvolysis of newly synthesized fluocinolone acetonide C-21 esters was analysed in comparison with fluocinonide during a 24-hour period of time. The solvolysis was performed in an ethanol-water (90:10 v/v) mixture using the excess of NaHCO3. The solvolytic mixtures of each investigated ester have been assayed by a RP-HPLC method using isocratic elution with methanol-water (75:25 v/v); flow rate 1 mL/min; detection at 238 nm; temperature 25 °C. Solvolytic rate constants were calculated from the obtained data. Geometry optimizations and charges calculations were carried out by Gaussian W03 software. A good correlation (R = 0.9924) was obtained between solvolytic rate constants and the polarity of the C-O2 bond of those esters. The established relation between solvolytic rate constant (K) and lipophilicity (cLogP) with experimental anti-inflammatory activity could be indicative for topical corticosteroid prodrug activation. Full article
(This article belongs to the Special Issue Prodrugs)
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178 KiB  
Article
Inter-Population Variability of Terpenoid Composition in Leaves of Pistacia lentiscus L. from Algeria: A Chemoecological Approach
by Samir Ait Said, Catherine Fernandez, Stéphane Greff, Franck Torre, Arezki Derridj, Thierry Gauquelin and Jean-Philippe Mevy
Molecules 2011, 16(3), 2646-2657; https://doi.org/10.3390/molecules16032646 - 22 Mar 2011
Cited by 21 | Viewed by 8146
Abstract
Three different altitudes were selected to study the variability of terpenoid composition from leaves of female plants of Pistacia lentiscus L. throughout the elevation gradient. GC-MS analyses showed that terpenoid contents change with altitude. Forty nine compounds were identified with a high interpopulation [...] Read more.
Three different altitudes were selected to study the variability of terpenoid composition from leaves of female plants of Pistacia lentiscus L. throughout the elevation gradient. GC-MS analyses showed that terpenoid contents change with altitude. Forty nine compounds were identified with a high interpopulation variability for low- and midaltitude sites that also exhibited the same major components when data were expressed on dry weight basis. However, Two-Way-ANOVA followed by Tukey’s post hoc test showed that monoterpene hydrocarbons increased with elevation, giving values of 21.7, 37.5 and 221.5 µg g−1 dw for low- mid- and highlands, respectively. On the other hand, applying P.C.A. with data expressed in percentage of the chromatogram of the volatile extract led to the identification of three chemotypes associated with altitudinal levels. In highlands (Group I), the major compounds were b-caryophyllene (12%), δ-cadinene (9.3%) and a-pinene (6.3%) while in midlands (Group II), b-caryophyllene (11.5%), δ-cadinene (8.6%) and caryophyllene oxide (6.8%) were the main components. In lowlands (Group III) δ-cadinene (10.9%), cubebol (10.5%) and β-bisabolene (7.7%) were chiefly present. Hence, the involvement of genetic factors, temperature and drought in the chemical polymorphism of P. lentiscus associated with elevation is discussed in this report. Full article
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209 KiB  
Article
Immunosuppressive Activity of 8-Gingerol on Immune Responses in Mice
by Jing Lu, Shuang Guan, Xue Shen, Wenhui Qian, Guoren Huang, Xuming Deng and Guanghong Xie
Molecules 2011, 16(3), 2636-2645; https://doi.org/10.3390/molecules16032636 - 22 Mar 2011
Cited by 35 | Viewed by 8330
Abstract
8-Gingerol is one of the principal components of ginger, which is widely used in China and elsewhere as a food, spice and herb. It shows immunosuppressive activity on the immune responses to ovalbumin (OVA) in mice. In the present study, we found that [...] Read more.
8-Gingerol is one of the principal components of ginger, which is widely used in China and elsewhere as a food, spice and herb. It shows immunosuppressive activity on the immune responses to ovalbumin (OVA) in mice. In the present study, we found that 8-gingerol suppressed lipopolysaccharide (LPS) and concanavalin A (ConA)-stimulated splenocyte proliferation in vitro. In vivo, 8-gingerol not only significantly suppressed Con A-, LPS- and OVA-induced splenocyte proliferation (P < 0.05) but also decreased the percentage of CD19+ B cells and CD3+ T cell (P < 0.05) at high doses (50, 100 mg/kg). Moreover, OVA-specific IgG, IgG1 and IgG2b levels in OVA-immunized mice were reduced by 8-gingerol at doses of 50, 100 mg/kg. These results suggest that 8-gingerol could suppress humoral and cellular immune responses in mice. The mechanism might be related to direct inhibition of sensitized T and B lymphocytes. Full article
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189 KiB  
Article
Synthesis and In Vitro Antibacterial Activity of 7-(3-Amino-6,7-dihydro-2-methyl-2H-pyrazolo[4,3-c] Pyridin-5(4H)-yl)fluoroquinolone Derivatives
by Xin Guo, Ming Liang Liu, Hui Yuan Guo, Yu Cheng Wang and Ju Xian Wang
Molecules 2011, 16(3), 2626-2635; https://doi.org/10.3390/molecules16032626 - 22 Mar 2011
Cited by 17 | Viewed by 7468
Abstract
A series of novel 7-(3-amino-6,7-dihydro-2-methyl-2H-pyrazolo[4,3-c]pyridin- 5(4H)-yl)fluoroquinolone derivatives were designed, synthesized and characterized by 1H-NMR, MS and HRMS. These fluoroquinolones were evaluated for their in vitro antibacterial activity against representative Gram-positive and Gram-negative strains. Results reveal that most of [...] Read more.
A series of novel 7-(3-amino-6,7-dihydro-2-methyl-2H-pyrazolo[4,3-c]pyridin- 5(4H)-yl)fluoroquinolone derivatives were designed, synthesized and characterized by 1H-NMR, MS and HRMS. These fluoroquinolones were evaluated for their in vitro antibacterial activity against representative Gram-positive and Gram-negative strains. Results reveal that most of the target compounds exhibit good growth inhibitory potency against methicillin-resistant Staphylococcus epidermidis (MRSE) (MIC: 0.25–4 μg/mL) and Streptococcus pneumoniae (MIC: 0.25–1 μg/mL). In addition, compound 8f is 8–128 fold more potent than the reference drugs gemifloxacin (GM), moxifloxacin (MX), ciprofloxacin (CP) and levofloxacin (LV) against methicillin-resistant Staphylococcus aureus 10-05 and Streptococcus hemolyticus 1002 and 2–64 fold more active against methicillin-sensitive Staphylococcus aureus 10-03 and 10-04. Full article
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913 KiB  
Article
Chemical Composition and In Vitro Activity of Plant Extracts from Ferula communis and Dittrichia viscosa against Postharvest Fungi
by Erjon Mamoci, Ivana Cavoski, Vito Simeone, Donato Mondelli, Lina Al-Bitar and Pierluigi Caboni
Molecules 2011, 16(3), 2609-2625; https://doi.org/10.3390/molecules16032609 - 22 Mar 2011
Cited by 39 | Viewed by 11217
Abstract
F. communis and D. viscosa are perennial Mediterranean weeds that have been used for different therapeutic purposes in traditional pharmacopeia. Plant extracts were obtained from air dried D. viscosa young shoots (DvA) and F. communis aerial part (FcA) and roots (FcR) with n [...] Read more.
F. communis and D. viscosa are perennial Mediterranean weeds that have been used for different therapeutic purposes in traditional pharmacopeia. Plant extracts were obtained from air dried D. viscosa young shoots (DvA) and F. communis aerial part (FcA) and roots (FcR) with n-hexane. The chemical compositions of the extracts were analyzed by HPLC-DAD, LC-MS (ESI) and LC-Q-TOF techniques. Two sesquiterpene lactones (inuviscolide, tomentosin) and three sesquiterpene acids (costic acid, hydroxycostic acid, ilicic acid) were identified from the D. viscosa extract, while in F. communis extracts three daucane sesquiterpenes (acetoxyferutinin, oxojaeskeanadioyl anisate, fertidin) and one coumarin (ferulenol) derivates were found. Biological activities of plant extracts were studied in in vitro experiments on the colonies and conidia of Botryotinia fuckeliana, Penicillium digitatum, P. expansum, Monilinia laxa, M. fructigena and Aspergillus spp. Extracts showed varying degree of antifungal activities on colony growth and conidia germination. The extract from FcA showed the least effect, while DvA extract had the strongest fungitoxic effects. FcR extract presented a fungitoxic effect on the colony growth, but it was not able to inhibit the conidia germination. These distinctions can be attributed to the differences in chemical composition of plant extracts. Full article
(This article belongs to the Section Natural Products Chemistry)
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353 KiB  
Article
Studies on the Genetic Variation of the Green Unicellular Alga Haematococcus pluvialis (Chlorophyceae) Obtained from Different Geographical Locations Using ISSR and RAPD Molecular Marker
by Noroozi Mostafa, Hishamuddin Omar, Soon Guan Tan and Suhaimi Napis
Molecules 2011, 16(3), 2599-2608; https://doi.org/10.3390/molecules16032599 - 22 Mar 2011
Cited by 17 | Viewed by 7272
Abstract
Haematococcus pluvialis (Flotow) is a unicellular green alga, which is considered to be the best astaxanthin-producing organism. Molecular markers are suitable tools for the purpose of finding out genetic variations in organisms; however there have been no studies conducted on ISSR or RAPD [...] Read more.
Haematococcus pluvialis (Flotow) is a unicellular green alga, which is considered to be the best astaxanthin-producing organism. Molecular markers are suitable tools for the purpose of finding out genetic variations in organisms; however there have been no studies conducted on ISSR or RAPD molecular markers for this organism. The DNA of 10 different strains of H. pluvialis (four strains from Iran, two strains from Finland, one strain from Switzerland and three strains from the USA) was extracted. A genetic similarity study was carried out using 14 ISSR and 12 RAPD primers. Moreover, the molecular weights of the bands produced ranged from 0.14 to 3.4 Kb. The PCA and dendrogram clustered the H. pluvialis strains into various groups according to their geographical origin. The lowest genetic similarity was between the Iran2 and USA2 strains (0.08) and the highest genetic similarity was between Finland1 and Finland2 (0.64). The maximum numbers of bands produced by the ISSR and RAPD primers were 35 and 6 bands, respectively. The results showed that ISSR and RAPD markers are useful for genetic diversity studies of Haematococcus as they showed geographical discrimination. Full article
(This article belongs to the Section Molecular Diversity)
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1490 KiB  
Article
Panduratin A Inhibits the Growth of A549 Cells through Induction of Apoptosis and Inhibition of NF-KappaB Translocation
by Shiau-Chuen Cheah, David R. Appleton, Sui-Ting Lee, May-Lynn Lam, A. Hamid A. Hadi and Mohd. Rais Mustafa
Molecules 2011, 16(3), 2583-2598; https://doi.org/10.3390/molecules16032583 - 21 Mar 2011
Cited by 60 | Viewed by 16337
Abstract
In the present study we investigated the effects of panduratin A, isolated from Boesenbergia rotunda, on proliferation and apoptosis in A549 human non-small cell lung cancer cells. Cell proliferation and induction of apoptosis was determined by the real-time cellular analyzer (RTCA), MTT [...] Read more.
In the present study we investigated the effects of panduratin A, isolated from Boesenbergia rotunda, on proliferation and apoptosis in A549 human non-small cell lung cancer cells. Cell proliferation and induction of apoptosis was determined by the real-time cellular analyzer (RTCA), MTT assay and High Content Screening (HCS). The RTCA assay indicated that panduratin A exhibited cytotoxicity, with an IC50 value of 4.4 µg/mL (10.8 µM). Panduratin A arrested cancer cells labeled with bromodeoxyuridine (BrdU) and phospho-Histone H3 in the mitotic phase. The cytotoxic effects of panduratin A were found to be accompanied by a dose-dependent induction of apoptosis, as assessed by DNA condensation, nuclear morphology and intensity, cell permeability, mitochondrial mass/ potential, F-actin and cytochrome c. In addition, treatment with an apoptosis-inducing concentration of panduratin A resulted in significant inhibition of Nuclear Factor-kappa Beta (NF-κB) translocation from cytoplasm to nuclei activated by tumor necrosis factor-alpha (TNF-α), as illustrated by the HCS assay. Our study provides evidence for cell growth inhibition and induction of apoptosis by panduratin A in the A549 cell line, suggesting its therapeutic potential as an NF-κB inhibitor. Full article
(This article belongs to the Section Natural Products Chemistry)
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625 KiB  
Article
Purification, Biochemical Characterization, and Bioactive Properties of a Lectin Purified from the Seeds of White Tepary Bean (Phaseolus Acutifolius Variety Latifolius)
by Carmen Valadez-Vega, Ana María Guzmán-Partida, Francisco Javier Soto-Cordova, Gerardo Álvarez-Manilla, José A. Morales-González, Eduardo Madrigal-Santillán, José Roberto Villagómez-Ibarra, Clara Zúñiga-Pérez, José Gutiérrez-Salinas and Marco A. Becerril-Flores
Molecules 2011, 16(3), 2561-2582; https://doi.org/10.3390/molecules16032561 - 21 Mar 2011
Cited by 16 | Viewed by 12075
Abstract
The present work shows the characterization of Phaseolus acutifolius variety latifolius, on which little research has been published, and provides detailed information on the corresponding lectin. This protein was purified from a semi-domesticated line of white tepary beans from Sonora, Mexico, by precipitation [...] Read more.
The present work shows the characterization of Phaseolus acutifolius variety latifolius, on which little research has been published, and provides detailed information on the corresponding lectin. This protein was purified from a semi-domesticated line of white tepary beans from Sonora, Mexico, by precipitation of the aqueous extract with ammonium sulfate, followed by affinity chromatography on an immobilized fetuin matrix. MALDI TOF analysis of Phaseolus acutifolius agglutinin (PAA) showed that this lectin is composed of monomers with molecular weights ranging between 28 and 31 kDa. At high salt concentrations, PAA forms a dimer of 63 kDa, but at low salt concentrations, the subunits form a tetramer. Analysis of PAA on 2D-PAGE showed that there are mainly three types of subunits with isoelectric points of 4.2, 4.4, and 4.5. The partial sequence obtained by LC/MS/MS of tryptic fragments from the PAA subunits showed 90–100% identity with subunits from genus Phaseolus lectins in previous reports. The tepary bean lectin showed lower hemagglutination activity than Phaseolus vulgaris hemagglutinin (PHA-E) toward trypsinized human A and O type erythrocytes. The hemagglutination activity was inhibited by N-glycans from glycoproteins. Affinity chromatography with the immobilized PAA showed a high affinity to glycopeptides from thyroglobulin, which also has N-glycans with a high content of N-acetylglucosamine. PAA showed less mitogenic activity toward human lymphocytes than PHA-L and Con A. The cytotoxicity of PAA was determined by employing three clones of the 3T3 cell line, demonstrating variability among the clones as follows: T4 (DI50 51.5 µg/mL); J20 (DI50 275 µg/mL), and N5 (DI50 72.5 µg/mL). Full article
(This article belongs to the Section Molecular Diversity)
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345 KiB  
Communication
LC/MS Guided Isolation of Alkaloids from Lotus Leaves by pH-Zone-Refining Counter-Current Chromatography
by Xia Xu, Cui-Rong Sun, Xiao-Jing Dai, Rui-Lin Hu, Yuan-Jiang Pan and Zhang-Fa Yang
Molecules 2011, 16(3), 2551-2560; https://doi.org/10.3390/molecules16032551 - 18 Mar 2011
Cited by 21 | Viewed by 7509
Abstract
The traditional methods used in natural product separation primarily target the major components and the minor components may thus be lost during the separation procedure. Consequently, it’s necessary to develop efficient methods for the preparative separation and purification of relatively minor bioactive components. [...] Read more.
The traditional methods used in natural product separation primarily target the major components and the minor components may thus be lost during the separation procedure. Consequently, it’s necessary to develop efficient methods for the preparative separation and purification of relatively minor bioactive components. In this paper, a LC/MS method was applied to guide the separation of crude extract of lotus (Nelumbo nucifera Gaertn.) leaves whereby a minor component was identified in the LC/MS analysis. Afterwards, an optimized pH-zone-refining CCC method was performed to isolate this product, identified as N-demethylarmepavine. The separation procedure was carried out with a biphasic solvent system composed of hexane-ethyl acetate-methyl alcohol-water (1:6:1:6, v/v) with triethylamine (10 mM) added to the upper organic phase as a retainer and hydrochloric acid (5 mM) to the aqueous mobile phase eluent. Two structurally similar compounds – nuciferine and roemerine – were also obtained from the crude lotus leaves extract. In total 500 mg of crude extract furnished 7.4 mg of N-demethylarmepavine, 45.3 mg of nuciferine and 26.6 mg of roemerine with purities of 90%, 92% and 96%, respectively. Their structures were further identified by HPLC/ESI-MSn, FTICR/MS and the comparison with reference compounds. Full article
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454 KiB  
Article
The Effect of Lycium Barbarum Polysaccharide on Alcohol-Induced Oxidative Stress in Rats
by Daye Cheng and Hong Kong
Molecules 2011, 16(3), 2542-2550; https://doi.org/10.3390/molecules16032542 - 17 Mar 2011
Cited by 111 | Viewed by 8866
Abstract
The aim of this study was to investigate the effects of Lycium barbarum Polysaccharide (LBP) on alcohol-induced liver damage in rats. A total of 36 rats were divided into control, ethanol and ethanol + LBP groups. Rats in the ethanol group were fed [...] Read more.
The aim of this study was to investigate the effects of Lycium barbarum Polysaccharide (LBP) on alcohol-induced liver damage in rats. A total of 36 rats were divided into control, ethanol and ethanol + LBP groups. Rats in the ethanol group were fed 7 g ethanol/kg body weight by gastric infusion, three times a day, for 30 consecutive days, while rats in the control group received the same volume of physiological saline instead of ethanol, and rats in ethanol + LBP group were fed both ethanol (7 g/kg body weight) and LBP (300 mg/Kg body weight/day). Alcoholic liver injury was examined by serum ALT and AST activities, alcoholic fatty liver was assessed by lipid levels, and oxidative stress was evaluated by SOD, CAT, GSH-Px, GSH and MDA assays. In the ethanol group, a significant elevation of enzymes and lipid in serum, increased MDA level and depletion of SOD, CAT, GSH-Px and GSH in liver were observed. LBP administration significantly ameliorated liver injury, prevented the progression of alcohol-induced fatty liver, and improved the antioxidant functions when compared with the ethanol group. Histopathological examination of rat liver revealed that LBP administration protected liver cells from the damage induced by ethanol. The results suggest that LBP is a promising agent to protect the liver from hepatotoxicity and fatty liver induced by ethanol intake. Full article
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157 KiB  
Article
Antioxidant Bibenzyl Derivatives from Notholaena nivea Desv.
by Giuseppina Cioffi, Paola Montoro, Olga Lock De Ugaz, Antonio Vassallo, Lorella Severino, Cosimo Pizza and Nunziatina De Tommasi
Molecules 2011, 16(3), 2527-2541; https://doi.org/10.3390/molecules16032527 - 17 Mar 2011
Cited by 14 | Viewed by 9134
Abstract
Four new bibenzyl derivatives were isolated, together with other known bibenzyls, by bioassay-guided fractionation of a CHCl3-MeOH extract of Notholaena nivea Desv. (Pteridaceae) aerial parts. The structures were elucidated by NMR, ESIMS and other spectral analyses. Their antioxidative effects towards superoxide, [...] Read more.
Four new bibenzyl derivatives were isolated, together with other known bibenzyls, by bioassay-guided fractionation of a CHCl3-MeOH extract of Notholaena nivea Desv. (Pteridaceae) aerial parts. The structures were elucidated by NMR, ESIMS and other spectral analyses. Their antioxidative effects towards superoxide, lipidic peroxidation and the 2,2'-azino-bis-3-ethilbenzothiazoline-6-sulfonic acid (ABTS) radical were assayed. Results showed that the compound 3,12-dihydroxy-5-methoxybibenzyl (6) is the most active compound in the ABTS free-radical scavenging test, while in the coupled oxidation of β-carotene and linoleic acid assay the compound 5,12-dihydroxy-3-methoxydibenzyl-6-carboxylic acid (1) exerted the highest activity after 1h. A superoxide anion enzymatic test was also carried out and the results were confirmed by an inhibition of xanthine oxidase activity assay. The putative protective role played by compounds 1 and 6 on the injurious effects of reactive oxygen metabolites on the intestinal epithelium, using a Caco-2 human cell line, was investigated. H2O2-induced alterations were prevented by preincubating the cells with compounds 1 and 6. Full article
(This article belongs to the Section Natural Products Chemistry)
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187 KiB  
Article
Synthesis and Biological Evaluation of Novel Acenaphthene Derivatives as Potential Antitumor Agents
by Yong-Mei Xie, Yi Deng, Xiao-Yun Dai, Jie Liu, Liang Ouyang, Yu-Quan Wei and Ying-Lan Zhao
Molecules 2011, 16(3), 2519-2526; https://doi.org/10.3390/molecules16032519 - 17 Mar 2011
Cited by 13 | Viewed by 7950
Abstract
Twelve novel acenaphthene derivatives have been synthesized. The structures of all compounds were confirmed by 1H-NMR, MS and elemental analysis. Their antitumor activities were evaluated in six human solid tumor cell lines, namely non-small cell lung cancer (H460), human colon adenocarcinoma (SW480), [...] Read more.
Twelve novel acenaphthene derivatives have been synthesized. The structures of all compounds were confirmed by 1H-NMR, MS and elemental analysis. Their antitumor activities were evaluated in six human solid tumor cell lines, namely non-small cell lung cancer (H460), human colon adenocarcinoma (SW480), human breast cancer cell (MDA-MB-468 and SKRB-3), human melanoma cell (A375) and human pancreatic cancer (BxPC-3) . Among them, compound 3c shows the best antitumor activity against SKRB-3 cell line, as high as the positive control adriamycin. Full article
(This article belongs to the Section Medicinal Chemistry)
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174 KiB  
Article
Screening of Natural Organic Volatiles from Prunus mahaleb L. Honey: Coumarin and Vomifoliol as Nonspecific Biomarkers
by Igor Jerković, Zvonimir Marijanović and Mladenka Malenica Staver
Molecules 2011, 16(3), 2507-2518; https://doi.org/10.3390/molecules16032507 - 16 Mar 2011
Cited by 36 | Viewed by 8212
Abstract
Headspace solid-phase microextraction (HS-SPME; PDMS/DVB fibre) and ultrasonic solvent extraction (USE; solvent A: pentane and diethyl ether (1:2 v/v), solvent B: dichloromethane) followed by gas chromatography and mass spectrometry (GC, GC-MS) were used for the analysis of Prunus mahaleb L. honey samples. Screening [...] Read more.
Headspace solid-phase microextraction (HS-SPME; PDMS/DVB fibre) and ultrasonic solvent extraction (USE; solvent A: pentane and diethyl ether (1:2 v/v), solvent B: dichloromethane) followed by gas chromatography and mass spectrometry (GC, GC-MS) were used for the analysis of Prunus mahaleb L. honey samples. Screening was focused toward chemical composition of natural organic volatiles to determine if it is useful as a method of determining honey-sourcing. A total of 34 compounds were identified in the headspace and 49 in the extracts that included terpenes, norisoprenoids and benzene derivatives, followed by minor percentages of aliphatic compounds and furan derivatives. High vomifoliol percentages (10.7%–24.2%) in both extracts (dominant in solvent B) and coumarin (0.3%–2.4%) from the extracts (more abundant in solvent A) and headspace (0.9%–1.8%) were considered characteristic for P. mahaleb honey and highlighted as potential nonspecific biomarkers of the honey’s botanical origin. In addition, comparison with P. mahaleb flowers, leaves, bark and wood volatiles from our previous research revealed common compounds among norisoprenoids and benzene derivatives. Full article
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109 KiB  
Article
Fungicidal Properties of the Essential Oil of Hesperozygis marifolia on Aspergillus flavus Link
by Marco Martín González-Chávez, Norma Cecilia Cárdenas-Ortega, Cristina Andrea Méndez-Ramos and Salud Pérez-Gutiérrez
Molecules 2011, 16(3), 2501-2506; https://doi.org/10.3390/molecules16032501 - 15 Mar 2011
Cited by 13 | Viewed by 8126
Abstract
The chemical composition of the essential oil from Hesperozygis marifolia was analyzed by gas chromatography-mass spectrometry (GC-MS), and fourteen compounds were identified. (R)-pulegone (40.75%), isomenthone (30.34%) and menthone (4.46%) were found to be the main components of the oil. The essential [...] Read more.
The chemical composition of the essential oil from Hesperozygis marifolia was analyzed by gas chromatography-mass spectrometry (GC-MS), and fourteen compounds were identified. (R)-pulegone (40.75%), isomenthone (30.34%) and menthone (4.46%) were found to be the main components of the oil. The essential oil at a concentration of 2.0 mg/mL and (R)-pulegone at concentration of 0.8 mg/mL completely inhibited the growth of Aspergillus flavus Link. The fungicidal effects of this essential oil warrant further research into its potential for commercial use. Full article
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2632 KiB  
Article
Role of the Morphology and Polyphosphate in Trichoderma harzianum Related to Cadmium Removal
by Adriana De Freitas Lima, Gabrielle Ferreira de Moura, Marcos Antonio Barbosa de Lima, Patrícia Mendes de Souza, Carlos Alberto Alves da Silva, Galba Maria De Campos Takaki and Aline Elesbão Do Nascimento
Molecules 2011, 16(3), 2486-2500; https://doi.org/10.3390/molecules16032486 - 15 Mar 2011
Cited by 35 | Viewed by 11286
Abstract
This study concerns the metabolism of polyphosphate in Trichoderma harzianum, a biocontrol agent with innate resistance against most chemicals used in agriculture, including metals, when grown in the presence of different concentrations of cadmium. The biomass production was affected by the concentration [...] Read more.
This study concerns the metabolism of polyphosphate in Trichoderma harzianum, a biocontrol agent with innate resistance against most chemicals used in agriculture, including metals, when grown in the presence of different concentrations of cadmium. The biomass production was affected by the concentration of metal used. Control cultures were able to accumulate polyphosphate under the conditions used. Moreover, the presence of cadmium induced a reduction in polyphosphate content related to the concentration used. The morphological/ultrastructural aspects were characterized by using optical and scanning electron microscopy, and were affected by the heavy metal presence and concentration. The efficiency of cadmium removal revealed the potential of the microorganism for use in remediation. The data indicate the potential for polyphosphate accumulation by the fungus, as well as its degradation related to tolerance/survival in the presence of cadmium ions. Full article
(This article belongs to the Section Natural Products Chemistry)
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1214 KiB  
Review
Miniproteins as Phage Display-Scaffolds for Clinical Applications
by Frederic Zoller, Uwe Haberkorn and Walter Mier
Molecules 2011, 16(3), 2467-2485; https://doi.org/10.3390/molecules16032467 - 14 Mar 2011
Cited by 29 | Viewed by 8993
Abstract
Miniproteins are currently developed as alternative, non-immunoglobin proteins for the generation of novel binding motifs. Miniproteins are rigid scaffolds that are stabilised by alpha-helices, beta-sheets and disulfide-constrained secondary structural elements. They are tolerant to multiple amino acid substitutions, which allow for the integration [...] Read more.
Miniproteins are currently developed as alternative, non-immunoglobin proteins for the generation of novel binding motifs. Miniproteins are rigid scaffolds that are stabilised by alpha-helices, beta-sheets and disulfide-constrained secondary structural elements. They are tolerant to multiple amino acid substitutions, which allow for the integration of a randomised affinity function into the stably folded framework. These properties classify miniprotein scaffolds as promising tools for lead structure generation using phage display technologies. Owing to their high enzymatic resistance and structural stability, miniproteins are ideal templates to display binding epitopes for medical applications in vivo. This review summarises the characteristics and the engineering of miniproteins as a novel class of scaffolds to generate of alternative binding agents using phage display screening. Moreover, recent developments for therapeutic and especially diagnostic applications of miniproteins are reviewed. Full article
(This article belongs to the Special Issue Phage Display of Combinatorial Libraries)
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233 KiB  
Review
Allobetulin and Its Derivatives: Synthesis and Biological Activity
by Wim Dehaen, Anastassiya A. Mashentseva and Talgat S. Seitembetov
Molecules 2011, 16(3), 2443-2466; https://doi.org/10.3390/molecules16032443 - 14 Mar 2011
Cited by 82 | Viewed by 10478
Abstract
This review covers the chemistry of allobetulin analogs, including their formation by rearrangement from betulin derivatives, their further derivatisation, their fusion with heterocyclic rings, and any further rearrangements of allobetulin compounds including ring opening, ring contraction and ring expansion reactions. In the last [...] Read more.
This review covers the chemistry of allobetulin analogs, including their formation by rearrangement from betulin derivatives, their further derivatisation, their fusion with heterocyclic rings, and any further rearrangements of allobetulin compounds including ring opening, ring contraction and ring expansion reactions. In the last part, the most important biological activities of allobetulin derivatives are listed. One hundred and fifteen references are cited and the relevant literature is covered, starting in 1922 up to the end of 2010. Full article
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161 KiB  
Article
Bioflocculant Production by Virgibacillus sp. Rob Isolated from the Bottom Sediment of Algoa Bay in the Eastern Cape, South Africa
by Sekelwa Cosa, Leonard V. Mabinya, Ademola O. Olaniran, Omobola O. Okoh, Kim Bernard, Shaun Deyzel and Anthony I. Okoh
Molecules 2011, 16(3), 2431-2442; https://doi.org/10.3390/molecules16032431 - 14 Mar 2011
Cited by 70 | Viewed by 8797
Abstract
A bioflocculant-producing marine bacterium previously isolated from marine sediment of Algoa Bay was screened for flocculant production. Comparative analysis of 16S rDNA sequence identified the isolate to have 99% similarity to Virgibacillus sp. XQ-1 and it was deposited in the GenBank as Virgibacillus [...] Read more.
A bioflocculant-producing marine bacterium previously isolated from marine sediment of Algoa Bay was screened for flocculant production. Comparative analysis of 16S rDNA sequence identified the isolate to have 99% similarity to Virgibacillus sp. XQ-1 and it was deposited in the GenBank as Virgibacillus sp. Rob with accession number HQ537127. The bacterium produced biflocculants optimally in glucose (70.4%) and peptone (70.4%) as sole sources of carbon and nitrogen, alkaline pH (12) (74%); and the presence of Fe2+ (74%). Chemical analysis of the bioflocculant revealed it to be a polysaccharide. Full article
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312 KiB  
Article
Investigating Spectrum of Biological Activity of 4- and 5-Chloro-2-hydroxy-N-[2-(arylamino)-1-alkyl-2-oxoethyl]benzamides
by Ales Imramovsky, Matus Pesko, Katarina Kralova, Marcela Vejsova, Jirina Stolarikova, Jarmila Vinsova and Josef Jampilek
Molecules 2011, 16(3), 2414-2430; https://doi.org/10.3390/molecules16032414 - 14 Mar 2011
Cited by 42 | Viewed by 6983
Abstract
In this study, a series of twenty-two 5-chloro-2-hydroxy-N-[2-(arylamino)-1-alkyl-2-oxoethyl]benzamides and ten 4-chloro-2-hydroxy-N-[2-(arylamino)-1-alkyl-2-oxoethyl]benzamides is described. The compounds were analyzed using RP-HPLC to determine lipophilicity. Primary in vitro screening of the synthesized compounds was performed against mycobacterial, bacterial and fungal strains. They [...] Read more.
In this study, a series of twenty-two 5-chloro-2-hydroxy-N-[2-(arylamino)-1-alkyl-2-oxoethyl]benzamides and ten 4-chloro-2-hydroxy-N-[2-(arylamino)-1-alkyl-2-oxoethyl]benzamides is described. The compounds were analyzed using RP-HPLC to determine lipophilicity. Primary in vitro screening of the synthesized compounds was performed against mycobacterial, bacterial and fungal strains. They were also evaluated for their activity related to the inhibition of photosynthetic electron transport (PET) in spinach (Spinacia oleracea L.) chloroplasts. The compounds showed biological activity comparable with or higher than the standards isoniazid, fluconazole, penicillin G or ciprofloxacin. For all the compounds, the relationships between the lipophilicity and the chemical structure of the studied compounds as well as their structure-activity relationships are discussed. Full article
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1625 KiB  
Review
Quantitative Mass Spectrometry for Bacterial Protein Toxins — A Sensitive, Specific, High-Throughput Tool for Detection and Diagnosis
by Anne E. Boyer, Maribel Gallegos-Candela, Renato C. Lins, Zsuzsanna Kuklenyik, Adrian Woolfitt, Hercules Moura, Suzanne Kalb, Conrad P. Quinn and John R. Barr
Molecules 2011, 16(3), 2391-2413; https://doi.org/10.3390/molecules16032391 - 14 Mar 2011
Cited by 47 | Viewed by 12510
Abstract
Matrix-assisted laser-desorption time-of-flight (MALDI-TOF) mass spectrometry (MS) is a valuable high-throughput tool for peptide analysis. Liquid chromatography electrospray ionization (LC-ESI) tandem-MS provides sensitive and specific quantification of small molecules and peptides. The high analytic power of MS coupled with high-specificity substrates is ideally [...] Read more.
Matrix-assisted laser-desorption time-of-flight (MALDI-TOF) mass spectrometry (MS) is a valuable high-throughput tool for peptide analysis. Liquid chromatography electrospray ionization (LC-ESI) tandem-MS provides sensitive and specific quantification of small molecules and peptides. The high analytic power of MS coupled with high-specificity substrates is ideally suited for detection and quantification of bacterial enzymatic activities. As specific examples of the MS applications in disease diagnosis and select agent detection, we describe recent advances in the analyses of two high profile protein toxin groups, the Bacillus anthracis toxins and the Clostridium botulinum neurotoxins. The two binary toxins produced by B. anthracis consist of protective antigen (PA) which combines with lethal factor (LF) and edema factor (EF), forming lethal toxin and edema toxin respectively. LF is a zinc-dependent endoprotease which hydrolyzes specific proteins involved in inflammation and immunity. EF is an adenylyl cyclase which converts ATP to cyclic-AMP. Toxin-specific enzyme activity for a strategically designed substrate, amplifies reaction products which are detected by MALDI-TOF-MS and LC-ESI-MS/MS. Pre-concentration/purification with toxin specific monoclonal antibodies provides additional specificity. These combined technologies have achieved high specificity, ultrasensitive detection and quantification of the anthrax toxins. We also describe potential applications to diseases of high public health impact, including Clostridium difficile glucosylating toxins and the Bordetella pertussis adenylyl cyclase. Full article
(This article belongs to the Special Issue Toxins - Organic and Analytical Chemistry)
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442 KiB  
Article
Cranberry Proanthocyanidins Mediate Growth Arrest of Lung Cancer Cells through Modulation of Gene Expression and Rapid Induction of Apoptosis
by Laura A. Kresty, Amy B. Howell and Maureen Baird
Molecules 2011, 16(3), 2375-2390; https://doi.org/10.3390/molecules16032375 - 11 Mar 2011
Cited by 40 | Viewed by 10776
Abstract
Cranberries are rich in bioactive constituents purported to enhance immune function, improve urinary tract health, reduce cardiovascular disease and more recently, inhibit cancer in preclinical models. However, identification of the cranberry constituents with the strongest cancer inhibitory potential and the mechanism associated with [...] Read more.
Cranberries are rich in bioactive constituents purported to enhance immune function, improve urinary tract health, reduce cardiovascular disease and more recently, inhibit cancer in preclinical models. However, identification of the cranberry constituents with the strongest cancer inhibitory potential and the mechanism associated with cancer inhibition by cranberries remains to be elucidated. This study investigated the ability of a proanthocyanidin rich cranberry fraction (PAC) to alter gene expression, induce apoptosis and impact the cell cycle machinery of human NCI-H460 lung cancer cells. Lung cancer is the leading cause of cancer-related deaths in the United States and five year survival rates remain poor at 16%. Thus, assessing potential inhibitors of lung cancer-linked signaling pathways is an active area of investigation. Full article
(This article belongs to the Special Issue Tannins)
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Article
A-Type Cranberry Proanthocyanidins Inhibit the RANKL-Dependent Differentiation and Function of Human Osteoclasts
by Shinichi Tanabe, Juliana Santos, Vu Dang La, Amy B. Howell and Daniel Grenier
Molecules 2011, 16(3), 2365-2374; https://doi.org/10.3390/molecules16032365 - 11 Mar 2011
Cited by 31 | Viewed by 10990
Abstract
This study investigated the effect of A-type cranberry proanthocyanidins (AC-PACs) on osteoclast formation and bone resorption activity. The differentiation of human pre-osteoclastic cells was assessed by tartrate-resistant acid phosphatase (TRAP) staining, while the secretion of interleukin-8 (IL-8) and matrix metalloproteinases (MMPs) was measured [...] Read more.
This study investigated the effect of A-type cranberry proanthocyanidins (AC-PACs) on osteoclast formation and bone resorption activity. The differentiation of human pre-osteoclastic cells was assessed by tartrate-resistant acid phosphatase (TRAP) staining, while the secretion of interleukin-8 (IL-8) and matrix metalloproteinases (MMPs) was measured by ELISA. Bone resorption activity was investigated by using a human bone plate coupled with an immunoassay that detected the release of collagen helical peptides. AC-PACs up to 100 µg/mL were atoxic for osteoclastic cells. TRAP staining evidenced a dose-dependent inhibition of osteoclastogenesis. More specifically, AC-PACs at 50 µg/mL caused a 95% inhibition of RANKL-dependent osteoclast differentiation. This concentration of AC-PACs also significantly increased the secretion of IL-8 (6-fold) and inhibited the secretion of both MMP-2 and MMP-9. Lastly, AC-PACs (10, 25, 50 and 100 µg/ml) affected bone degradation mediated by mature osteoclasts by significantly decreasing the release of collagen helical peptides. This study suggests that AC-PACs can interfere with osteoclastic cell maturation and physiology as well as prevent bone resorption. These compounds may be considered as therapeutic agents for the prevention and treatment of periodontitis. Full article
(This article belongs to the Special Issue Tannins)
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225 KiB  
Review
Wine and Grape Tannin Interactions with Salivary Proteins and Their Impact on Astringency: A Review of Current Research
by Jacqui M. McRae and James A. Kennedy
Molecules 2011, 16(3), 2348-2364; https://doi.org/10.3390/molecules16032348 - 11 Mar 2011
Cited by 208 | Viewed by 19046
Abstract
Astringency is an important characteristic of red wine quality. The sensation is generally thought to be produced by the interaction of wine tannins with salivary proteins and the subsequent aggregation and precipitation of protein-tannin complexes. The importance of wine astringency for marketability has [...] Read more.
Astringency is an important characteristic of red wine quality. The sensation is generally thought to be produced by the interaction of wine tannins with salivary proteins and the subsequent aggregation and precipitation of protein-tannin complexes. The importance of wine astringency for marketability has led to a wealth of research on the causes of astringency and how tannins impact the quality of the sensation, particularly with respect to tannin structure. Ultimately, the understanding of how tannin structure impacts astringency will allow the controlled manipulation of tannins via such methods as micro-oxygenation or fining to improve the quality of wines. Full article
(This article belongs to the Special Issue Tannins)
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230 KiB  
Article
Antioxidant and Antityrosinase Activities of Various Extracts from the Fruiting Bodies of Lentinus lepideus
by Ki Nam Yoon, Nuhu Alam, Kyung Rim Lee, Pyung Gyun Shin, Jong Chun Cheong, Young Bok Yoo and Tae Soo Lee
Molecules 2011, 16(3), 2334-2347; https://doi.org/10.3390/molecules16032334 - 10 Mar 2011
Cited by 52 | Viewed by 9872
Abstract
Lentinus lepideus is an edible mushroom currently available in Korea. The acetone, methanol and hot water extracts were prepared and assayed for their antioxidant and antityrosinase inhibitory activities. The hot water extract showed the strongest β-carotene-linoleic acid inhibition compared to the other extracts. [...] Read more.
Lentinus lepideus is an edible mushroom currently available in Korea. The acetone, methanol and hot water extracts were prepared and assayed for their antioxidant and antityrosinase inhibitory activities. The hot water extract showed the strongest β-carotene-linoleic acid inhibition compared to the other extracts. At 8 mg/mL, the methanolic extract showed a high reducing power of 1.21. The acetone and methanol extracts were more effective in scavenging DPPH radicals than the hot water extract. The strongest chelating effect was obtained from the methanolic extract. Xanthine oxidase and tyrosinase inhibitory activities of the acetonic, methanol and hot water extracts increased with increasing concentration. Gallic acid, chlorogenic acid, vanillin, naringin, naringenin, formononetin, and biochanin-A were detected in the acetonitrile and hydrochloric acid (5:1) solvent extract. This study suggests that fruiting bodies of L. lepideus can potentially be used as a readily accessible source of natural antioxidants. Full article
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Article
An Allelochemical from Myrica gale with Strong Phytotoxic Activity against Highly Invasive Fallopia x bohemica Taxa
by Jean Popovici, Cedric Bertrand, Dominique Jacquemoud, Floriant Bellvert, Maria P. Fernandez, Gilles Comte and Florence Piola
Molecules 2011, 16(3), 2323-2333; https://doi.org/10.3390/molecules16032323 - 10 Mar 2011
Cited by 23 | Viewed by 10445
Abstract
We report the identification of the allelochemical 3-(1-oxo-3-phenylpropyl)-1,1,5-trimethylcyclo-hexane-2,4,6-trione, known as myrigalone A, from the fruits and leaves of Myrica gale. The structure of the compound was confirmed by high-resolution techniques (UV, MS and NMR analysis). The compound is phytotoxic towards classical plant [...] Read more.
We report the identification of the allelochemical 3-(1-oxo-3-phenylpropyl)-1,1,5-trimethylcyclo-hexane-2,4,6-trione, known as myrigalone A, from the fruits and leaves of Myrica gale. The structure of the compound was confirmed by high-resolution techniques (UV, MS and NMR analysis). The compound is phytotoxic towards classical plant species used for allelochemical assays and also against Fallopia x bohemica, a highly invasive plant. Application of either powdered dry leaves or dry fruits of M. gale also showed in vitro phytotoxic activity. We hypothesize that M. gale could be used as a green allelopathic shield to control Fallopia x bohemica invasion, in addition to its potential use as an environmentally friendly herbicide. Full article
(This article belongs to the Section Natural Products Chemistry)
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438 KiB  
Article
Effect of Calcinated Oyster Shell Powder on Growth, Yield, Spawn Run, and Primordial Formation of King Oyster Mushroom (Pleurotus Eryngii)
by Ung-Kyu Choi, Ok-Hwan Lee and Young-Chan Kim
Molecules 2011, 16(3), 2313-2322; https://doi.org/10.3390/molecules16032313 - 10 Mar 2011
Cited by 18 | Viewed by 9882
Abstract
This study was conducted to evaluate the calcium (Ca) absorption efficacy of king oyster mushroom (Pleurotus eryngii) grown on sawdust medium supplemented with Ca-sources, including oyster shell powder, and to determine the efficacy of oyster shell powder as a calcium supplement [...] Read more.
This study was conducted to evaluate the calcium (Ca) absorption efficacy of king oyster mushroom (Pleurotus eryngii) grown on sawdust medium supplemented with Ca-sources, including oyster shell powder, and to determine the efficacy of oyster shell powder as a calcium supplement on growth, yield, spawn run and primordial formation of P. eryngii. Optimum calcination of oyster shell powder was achieved at the temperature of 620.56 °C. A 1% supplementation of oyster shell powder in sawdust medium did not suppress the mycelial growth of P. eryngii. Also the supplementation of 2% calcinated oyster shell powder to sawdust medium potentially increased the calcium content up to a level of 315.7 ± 15.7 mg/100 g in the fruiting body of P. eryngii, without extension of duration of spawn run and the retardation of the days to primordial formation. These results suggest that the shellfish by-products, including oyster shell powder, can be utilized to develop calcium enriched king oyster mushrooms. Full article
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