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Sample records for 5c aliphatic glucosinolates

  1. Differential effects of indole and aliphatic glucosinolates on lepidopteran herbivores.

    PubMed

    Müller, René; de Vos, Martin; Sun, Joel Y; Sønderby, Ida E; Halkier, Barbara A; Wittstock, Ute; Jander, Georg

    2010-08-01

    Glucosinolates are a diverse group of defensive secondary metabolites that is characteristic of the Brassicales. Arabidopsis thaliana (L.) Heynh. (Brassicaceae) lines with mutations that greatly reduce abundance of indole glucosinolates (cyp79B2 cyp79B3), aliphatic glucosinolates (myb28 myb29), or both (cyp79B2 cyp79B3 myb28 myb29) make it possible to test the in vivo defensive function of these two major glucosinolate classes. In experiments with Lepidoptera that are not crucifer-feeding specialists, aliphatic and indole glucosinolates had an additive effect on Spodoptera exigua (Hübner) (Lepidoptera: Noctuidae) larval growth, whereas Trichoplusia ni (Hübner) (Lepidoptera: Noctuidae) and Manduca sexta (L.) (Lepidoptera: Sphingidae) were affected only by the absence of aliphatic glucosinolates. In the case of two crucifer-feeding specialists, Pieris rapae (L.) (Lepidoptera: Pieridae) and Plutella xylostella (L.) (Lepidoptera: Plutellidae), there were no major changes in larval performance due to decreased aliphatic and/or indole glucosinolate content. Nevertheless, choice tests show that aliphatic and indole glucosinolates act in an additive manner to promote larval feeding of both species and P. rapae oviposition. Together, these results support the hypothesis that a diversity of glucosinolates is required to limit the growth of multiple insect herbivores. PMID:20617455

  2. The Impact of the Absence of Aliphatic Glucosinolates on Insect Herbivory in Arabidopsis

    PubMed Central

    van Dam, Nicole M.; Bertossi, Monica; Grandi, Valentina; Mizzi, Luca; Soloviev, Mikhail; Szabados, Laszlo; Molthoff, Jos W.; Schipper, Bert; Verbocht, Hans; de Vos, Ric C. H.; Morandini, Piero; Aarts, Mark G. M.; Bovy, Arnaud

    2008-01-01

    Aliphatic glucosinolates are compounds which occur in high concentrations in Arabidopsis thaliana and other Brassicaceae species. They are important for the resistance of the plant to pest insects. Previously, the biosynthesis of these compounds was shown to be regulated by transcription factors MYB28 and MYB29. We now show that MYB28 and MYB29 are partially redundant, but in the absence of both, the synthesis of all aliphatic glucosinolates is blocked. Untargeted and targeted biochemical analyses of leaf metabolites showed that differences between single and double knock-out mutants and wild type plants were restricted to glucosinolates. Biosynthesis of long-chain aliphatic glucosinolates was blocked by the myb28 mutation, while short-chain aliphatic glucosinolates were reduced by about 50% in both the myb28 and the myb29 single mutants. Most remarkably, all aliphatic glucosinolates were completely absent in the double mutant. Expression of glucosinolate biosynthetic genes was slightly but significantly reduced by the single myb mutations, while the double mutation resulted in a drastic decrease in expression of these genes. Since the myb28myb29 double mutant is the first Arabidopsis genotype without any aliphatic glucosinolates, we used it to establish the relevance of aliphatic glucosinolate biosynthesis to herbivory by larvae of the lepidopteran insect Mamestra brassicae. Plant damage correlated inversely to the levels of aliphatic glucosinolates observed in those plants: Larval weight gain was 2.6 fold higher on the double myb28myb29 mutant completely lacking aliphatic glucosinolates and 1.8 higher on the single mutants with intermediate levels of aliphatic glucosinolates compared to wild type plants. PMID:18446225

  3. Comparative quantitative trait loci mapping of aliphatic, indolic and benzylic glucosinolate production in Arabidopsis thaliana leaves and seeds.

    PubMed Central

    Kliebenstein, D J; Gershenzon, J; Mitchell-Olds, T

    2001-01-01

    Secondary metabolites are a diverse set of plant compounds believed to have numerous functions in plant-environment interactions. Despite this importance, little is known about the regulation of secondary metabolite accumulation. We are studying the regulation of glucosinolates, a large group of secondary metabolites, in Arabidopsis to investigate how secondary metabolism is controlled. We utilized Ler and Cvi, two ecotypes of Arabidopsis that have striking differences in both the types and amounts of glucosinolates that accumulate in the seeds and leaves. QTL analysis identified six loci determining total aliphatic glucosinolate accumulation, six loci controlling total indolic glucosinolate concentration, and three loci regulating benzylic glucosinolate levels. Our results show that two of the loci controlling total aliphatic glucosinolates map to biosynthetic loci that interact epistatically to regulate aliphatic glucosinolate accumulation. In addition to the six loci regulating total indolic glucosinolate concentration, mapping of QTL for the individual indolic glucosinolates identified five additional loci that were specific to subsets of the indolic glucosinolates. These data show that there are a large number of variable loci controlling glucosinolate accumulation in Arabidopsis thaliana. PMID:11560911

  4. Two Novel Flavin-Containing Monooxygenases Involved in Biosynthesis of Aliphatic Glucosinolates.

    PubMed

    Kong, Wenwen; Li, Jing; Yu, Qingyue; Cang, Wei; Xu, Rui; Wang, Yang; Ji, Wei

    2016-01-01

    Glucosinolates, a class of secondary metabolites from cruciferous plants, are derived from amino acids and have diverse biological activities, such as in biotic defense, depending on their side chain modification. The first structural modification step in the synthesis of aliphatic (methionine-derived) glucosinolates-S-oxygenation of methylthioalkyl glucosinolates to methylsulfinylalkyl glucosinolates-was found to be catalyzed by five flavin-containing monooxygenases (FMOs), FMOGS-OX1-5. Here, we report two additional FMOGS-OX enzymes, FMOGS-OX6, and FMOGS-OX7, encoded by At1g12130 and At1g12160, respectively. The overexpression of both FMOGS-OX6 and FMOGS-OX7 decreased the ratio of methylthioalkyl glucosinolates to the sum of methylthioalkyl and methylsulfinylalkyl glucosinolates, suggesting that the introduction of the two genes converted methylthioalkyl glucosinolates into methylsulfinylalkyl glucosinolates. Analysis of expression pattern revealed that the spatial expression of the two genes is quite similar and partially overlapped with the other FMOGS-OX genes, which are primarily expressed in vascular tissue. We further analyzed the responsive expression pattern of all the seven FMOGS-OX genes to exogenous treatment with abscisic acid, 1-aminocyclopropane-1-carboxylic acid (ACC), jasmonic acid (JA), salicylic acid, indole-3-acetic acid (IAA), and low and high temperatures. Although these genes showed same tendency toward the changing stimulus, the sensitivity of each gene was quite different. The variety in spatial expression among the FMOGS-OX genes while responding to environmental stimulus indicated a complex and finely tuned regulation of glucosinolates modifications. Identification of these two novel FMOGS-OX enzymes will enhance the understanding of glucosinolates modifications and the importance of evolution of these duplicated genes. PMID:27621741

  5. CYP79F1 and CYP79F2 have distinct functions in the biosynthesis of aliphatic glucosinolates in Arabidopsis.

    PubMed

    Chen, Sixue; Glawischnig, Erich; Jørgensen, Kirsten; Naur, Peter; Jørgensen, Bodil; Olsen, Carl-Erik; Hansen, Carsten H; Rasmussen, Hasse; Pickett, John A; Halkier, Barbara A

    2003-03-01

    Cytochromes P450 of the CYP79 family catalyze the conversion of amino acids to oximes in the biosynthesis of glucosinolates, a group of natural plant products known to be involved in plant defense and as a source of flavor compounds, cancer-preventing agents and bioherbicides. We report a detailed biochemical analysis of the substrate specificity and kinetics of CYP79F1 and CYP79F2, two cytochromes P450 involved in the biosynthesis of aliphatic glucosinolates in Arabidopsis thaliana. Using recombinant CYP79F1 and CYP79F2 expressed in Escherichia coli and Saccharomyces cerevisiae, respectively, we show that CYP79F1 metabolizes mono- to hexahomomethionine, resulting in both short- and long-chain aliphatic glucosinolates. In contrast, CYP79F2 exclusively metabolizes long-chain elongated penta- and hexahomomethionines. CYP79F1 and CYP79F2 are spatially and developmentally regulated, with different gene expression patterns. CYP79F2 is highly expressed in hypocotyl and roots, whereas CYP79F1 is strongly expressed in cotyledons, rosette leaves, stems, and siliques. A transposon-tagged CYP79F1 knockout mutant completely lacks short-chain aliphatic glucosinolates, but has an increased level of long-chain aliphatic glucosinolates, especially in leaves and seeds. The level of long-chain aliphatic glucosinolates in a transposon-tagged CYP79F2 knockout mutant is substantially reduced, whereas the level of short-chain aliphatic glucosinolates is not affected. Biochemical characterization of CYP79F1 and CYP79F2, and gene expression analysis, combined with glucosinolate profiling of knockout mutants demonstrate the functional role of these enzymes. This provides valuable insights into the metabolic network leading to the biosynthesis of aliphatic glucosinolates, and into metabolic engineering of altered aliphatic glucosinolate profiles to improve nutritional value and pest resistance. PMID:12609033

  6. Topsoil drying combined with increased sulfur supply leads to enhanced aliphatic glucosinolates in Brassica juncea leaves and roots.

    PubMed

    Tong, Yu; Gabriel-Neumann, Elke; Ngwene, Benard; Krumbein, Angelika; George, Eckhard; Platz, Stefanie; Rohn, Sascha; Schreiner, Monika

    2014-01-01

    The decrease of water availability is leading to an urgent demand to reduce the plants' water supply. This study evaluates the effect of topsoil drying, combined with varying sulfur (S) supply on glucosinolates in Brassica juncea in order to reveal whether a partial root drying may already lead to a drought-induced glucosinolate increase promoted by an enhanced S supply. Without decreasing biomass, topsoil drying initiated an increase in aliphatic glucosinolates in leaves and in topsoil dried roots supported by increased S supply. Simultaneously, abscisic acid was determined, particularly in dehydrated roots, associated with an increased abscisic acid concentration in leaves under topsoil drying. This indicates that the dehydrated roots were the direct interface for the plants' stress response and that the drought-induced accumulation of aliphatic glucosinolates is related to abscisic acid formation. Indole and aromatic glucosinolates decreased, suggesting that these glucosinolates are less involved in the plants' response to drought. PMID:24444925

  7. Two Novel Flavin-Containing Monooxygenases Involved in Biosynthesis of Aliphatic Glucosinolates

    PubMed Central

    Kong, Wenwen; Li, Jing; Yu, Qingyue; Cang, Wei; Xu, Rui; Wang, Yang; Ji, Wei

    2016-01-01

    Glucosinolates, a class of secondary metabolites from cruciferous plants, are derived from amino acids and have diverse biological activities, such as in biotic defense, depending on their side chain modification. The first structural modification step in the synthesis of aliphatic (methionine-derived) glucosinolates—S-oxygenation of methylthioalkyl glucosinolates to methylsulfinylalkyl glucosinolates—was found to be catalyzed by five flavin-containing monooxygenases (FMOs), FMOGS-OX1-5. Here, we report two additional FMOGS-OX enzymes, FMOGS-OX6, and FMOGS-OX7, encoded by At1g12130 and At1g12160, respectively. The overexpression of both FMOGS-OX6 and FMOGS-OX7 decreased the ratio of methylthioalkyl glucosinolates to the sum of methylthioalkyl and methylsulfinylalkyl glucosinolates, suggesting that the introduction of the two genes converted methylthioalkyl glucosinolates into methylsulfinylalkyl glucosinolates. Analysis of expression pattern revealed that the spatial expression of the two genes is quite similar and partially overlapped with the other FMOGS-OX genes, which are primarily expressed in vascular tissue. We further analyzed the responsive expression pattern of all the seven FMOGS-OX genes to exogenous treatment with abscisic acid, 1-aminocyclopropane-1-carboxylic acid (ACC), jasmonic acid (JA), salicylic acid, indole-3-acetic acid (IAA), and low and high temperatures. Although these genes showed same tendency toward the changing stimulus, the sensitivity of each gene was quite different. The variety in spatial expression among the FMOGS-OX genes while responding to environmental stimulus indicated a complex and finely tuned regulation of glucosinolates modifications. Identification of these two novel FMOGS-OX enzymes will enhance the understanding of glucosinolates modifications and the importance of evolution of these duplicated genes. PMID:27621741

  8. The impact of the absence of aliphatic glucosinolates on water transport under salt stress in Arabidopsis thaliana

    PubMed Central

    Martínez-Ballesta, Mcarmen; Moreno-Fernández, Diego A.; Castejón, Diego; Ochando, Cristina; Morandini, Piero A.; Carvajal, Micaela

    2015-01-01

    Members of the Brassicaceae are known for their contents of nutrients and health-promoting phytochemicals, including glucosinolates. Exposure to salinity increases the levels of several of these compounds, but their role in abiotic stress response is unclear. The effect of aliphatic glucosinolates on plant water balance and growth under salt stress, involving aquaporins, was investigated by means of Arabidopsis thaliana mutants impaired in aliphatic glucosinolate biosynthesis, which is controlled by two transcription factors: Myb28 and Myb29. The double mutant myb28myb29, completely lacking aliphatic glucosinolates, was compared to wild type Col-0 (WT) and the single mutant myb28. A greater reduction in the hydraulic conductivity of myb28myb29 was observed under salt stress, when compared to the WT and myb28; this correlated with the abundance of both PIP1 and PIP2 aquaporin subfamilies. Also, changes in root architecture in response to salinity were genotype dependent. Treatment with NaCl altered glucosinolates biosynthesis in a similar way in WT and the single mutant and differently in the double mutant. The results indicate that short-chain aliphatic glucosinolates may contribute to water saving under salt stress. PMID:26236322

  9. Collard Landraces are novel sources of Glucoraphanin and other Aliphatic Glucosinolates

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Glucosinolates form an important class of metabolites in Brassicas whose cognate isothiocyanates may provide chemoprotective effects in humans. Although certain B. oleracea crops have well documented glucosinolate profiles, collard (Brassica oleracea L. subsp. oleracea convar. acephala var. viridis ...

  10. Collard land races are novel sources of glucoraphanin and other aliphatic glucosinolates

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Glucosinolates form an important class of metabolites in Brassicas whose cognate isothiocyanates may provide chemoprotective effects in humans. Although certain B. oleracea crops have well documented glucosinolate profiles, collard (Brassica oleracea L. subsp. oleracea convar. acephala var. viridis)...

  11. Aliphatic glucosinolate synthesis and gene expression changes in gamma-irradiated cabbage.

    PubMed

    Banerjee, Aparajita; Rai, Archana N; Penna, Suprasanna; Variyar, Prasad S

    2016-10-15

    Glucosinolates, found principally in the plant order Brassicales, are modulated by different post-harvest processing operations. Among these, ionizing radiation, a non-thermal process, has gained considerable interest for ensuring food security and safety. In gamma-irradiated cabbage, enhanced sinigrin, a major glucosinolate, has been reported. However, the molecular basis of such a radiation induced effect is not known. Herein, the effect of radiation processing on the expression of glucosinolate biosynthetic genes was investigated. RT-PCR based expression analysis of seven glucosinolate biosynthetic pathway genes (MYB28, CYP79F1, CYP83A1, SUR1, UGT74B1, SOT18 and TGG1) showed that CYP83A1, MYB28, UGT74B1, CYP79F1 and SUR1 were up-regulated in irradiated cabbage. The content of jasmonates, signalling molecules involved in glucosinolate induction was, however, unaffected in irradiated cabbage suggesting their non-involvement in glucosinolate induction during radiation processing. This is the first report on the effect of gamma irradiation on the expression of glucosinolate biosynthetic genes in vegetables. PMID:27173540

  12. MAM3 catalyzes the formation of all aliphatic glucosinolate chain lengths in Arabidopsis.

    PubMed

    Textor, Susanne; de Kraker, Jan-Willem; Hause, Bettina; Gershenzon, Jonathan; Tokuhisa, James G

    2007-05-01

    Chain elongated, methionine (Met)-derived glucosinolates are a major class of secondary metabolites in Arabidopsis (Arabidopsis thaliana). The key enzymatic step in determining the length of the chain is the condensation of acetyl-coenzyme A with a series of omega-methylthio-2-oxoalkanoic acids, catalyzed by methylthioalkylmalate (MAM) synthases. The existence of two MAM synthases has been previously reported in the Arabidopsis ecotype Columbia: MAM1 and MAM3 (formerly known as MAM-L). Here, we describe the biochemical properties of the MAM3 enzyme, which is able to catalyze all six condensation reactions of Met chain elongation that occur in Arabidopsis. Underlining its broad substrate specificity, MAM3 also accepts a range of non-Met-derived 2-oxoacids, e.g. converting pyruvate to citramalate and 2-oxoisovalerate to isopropylmalate, a step in leucine biosynthesis. To investigate its role in vivo, we identified plant lines with mutations in MAM3 that resulted in a complete lack or greatly reduced levels of long-chain glucosinolates. This phenotype could be complemented by reintroduction of a MAM3 expression construct. Analysis of MAM3 mutants demonstrated that MAM3 catalyzes the formation of all glucosinolate chain lengths in vivo as well as in vitro, making this enzyme the major generator of glucosinolate chain length diversity in the plant. The localization of MAM3 in the chloroplast suggests that this organelle is the site of Met chain elongation. PMID:17369439

  13. Structure and Mechanism of Isopropylmalate Dehydrogenase from Arabidopsis thaliana: INSIGHTS ON LEUCINE AND ALIPHATIC GLUCOSINOLATE BIOSYNTHESIS.

    PubMed

    Lee, Soon Goo; Nwumeh, Ronald; Jez, Joseph M

    2016-06-24

    Isopropylmalate dehydrogenase (IPMDH) and 3-(2'-methylthio)ethylmalate dehydrogenase catalyze the oxidative decarboxylation of different β-hydroxyacids in the leucine- and methionine-derived glucosinolate biosynthesis pathways, respectively, in plants. Evolution of the glucosinolate biosynthetic enzyme from IPMDH results from a single amino acid substitution that alters substrate specificity. Here, we present the x-ray crystal structures of Arabidopsis thaliana IPMDH2 (AtIPMDH2) in complex with either isopropylmalate and Mg(2+) or NAD(+) These structures reveal conformational changes that occur upon ligand binding and provide insight on the active site of the enzyme. The x-ray structures and kinetic analysis of site-directed mutants are consistent with a chemical mechanism in which Lys-232 activates a water molecule for catalysis. Structural analysis of the AtIPMDH2 K232M mutant and isothermal titration calorimetry supports a key role of Lys-232 in the reaction mechanism. This study suggests that IPMDH-like enzymes in both leucine and glucosinolate biosynthesis pathways use a common mechanism and that members of the β-hydroxyacid reductive decarboxylase family employ different active site features for similar reactions. PMID:27137927

  14. Four genes encoding MYB28, a major transcriptional regulator of the aliphatic glucosinolate pathway, are differentially expressed in the allopolyploid Brassica juncea.

    PubMed

    Augustine, Rehna; Majee, Manoj; Gershenzon, Jonathan; Bisht, Naveen C

    2013-11-01

    Glucosinolates are Capparales-specific secondary metabolites that have immense potential in human health and agriculture. Unlike Arabidopsis thaliana, our knowledge about glucosinolate regulators in the Brassica crops is sparse. In the current study, four MYB28 homologues were identified (BjuMYB28-1,-2,-3,-4) from the polyploid Brassica juncea, and the effects of allopolyploidization on the divergence of gene sequence, structure, function, and expression were assessed. The deduced protein sequences of the four BjuMYB28 genes showed 76.1-83.1% identity with the Arabidopsis MYB28. Phylogenetic analysis revealed that the four BjuMYB28 proteins have evolved via the hybridization and duplication processes forming the B. juncea genome (AABB) from B. rapa (AA) and B. nigra (BB), while retaining high levels of sequence conservation. Mutant complementation and over-expression studies in A. thaliana showed that all four BjuMYB28 genes encode functional MYB28 proteins and resulted in similar aliphatic glucosinolate composition and content. Detailed expression analysis using qRT-PCR assays and promoter-GUS lines revealed that the BjuMYB28 genes have both tissue- and cell-specific expression partitioning in B. juncea. The two B-genome origin BjuMYB28 genes had more abundant transcripts during the early stages of plant development than the A-genome origin genes. However, with the onset of the reproductive phase, expression levels of all four BjuMYB28 increased significantly, which may be necessary for producing and maintaining high amounts of aliphatic glucosinolates during the later stages of plant development. Taken together, our results suggest that the four MYB28 genes are differentially expressed and regulated in B. juncea to play discrete though overlapping roles in controlling aliphatic glucosinolate biosynthesis. PMID:24043856

  15. Three genes encoding AOP2, a protein involved in aliphatic glucosinolate biosynthesis, are differentially expressed in Brassica rapa.

    PubMed

    Zhang, Jifang; Liu, Zhiyuan; Liang, Jianli; Wu, Jian; Cheng, Feng; Wang, Xiaowu

    2015-10-01

    The glucosinolate biosynthetic gene AOP2 encodes an enzyme that plays a crucial role in catalysing the conversion of beneficial glucosinolates into anti-nutritional ones. In Brassica rapa, three copies of BrAOP2 have been identified, but their function in establishing the glucosinolate content of B. rapa is poorly understood. Here, we used phylogenetic and gene structure analyses to show that BrAOP2 proteins have evolved via a duplication process retaining two highly conserved domains at the N-terminal and C-terminal regions, while the middle part has experienced structural divergence. Heterologous expression and in vitro enzyme assays and Arabidopsis mutant complementation studies showed that all three BrAOP2 genes encode functional BrAOP2 proteins that convert the precursor methylsulfinyl alkyl glucosinolate to the alkenyl form. Site-directed mutagenesis showed that His356, Asp310, and Arg376 residues are required for the catalytic activity of one of the BrAOP2 proteins (BrAOP2.1). Promoter-β-glucuronidase lines revealed that the BrAOP2.3 gene displayed an overlapping but distinct tissue- and cell-specific expression profile compared with that of the BrAOP2.1 and BrAOP2.2 genes. Quantitative real-time reverse transcription-PCR assays demonstrated that BrAOP2.1 showed a slightly different pattern of expression in below-ground tissue at the seedling stage and in the silique at the reproductive stage compared with BrAOP2.2 and BrAOP2.3 genes in B. rapa. Taken together, our results revealed that all three BrAOP2 paralogues are active in B. rapa but have functionally diverged. PMID:26188204

  16. Three genes encoding AOP2, a protein involved in aliphatic glucosinolate biosynthesis, are differentially expressed in Brassica rapa

    PubMed Central

    Zhang, Jifang; Liu, Zhiyuan; Liang, Jianli; Wu, Jian; Cheng, Feng; Wang, Xiaowu

    2015-01-01

    The glucosinolate biosynthetic gene AOP2 encodes an enzyme that plays a crucial role in catalysing the conversion of beneficial glucosinolates into anti-nutritional ones. In Brassica rapa, three copies of BrAOP2 have been identified, but their function in establishing the glucosinolate content of B. rapa is poorly understood. Here, we used phylogenetic and gene structure analyses to show that BrAOP2 proteins have evolved via a duplication process retaining two highly conserved domains at the N-terminal and C-terminal regions, while the middle part has experienced structural divergence. Heterologous expression and in vitro enzyme assays and Arabidopsis mutant complementation studies showed that all three BrAOP2 genes encode functional BrAOP2 proteins that convert the precursor methylsulfinyl alkyl glucosinolate to the alkenyl form. Site-directed mutagenesis showed that His356, Asp310, and Arg376 residues are required for the catalytic activity of one of the BrAOP2 proteins (BrAOP2.1). Promoter–β-glucuronidase lines revealed that the BrAOP2.3 gene displayed an overlapping but distinct tissue- and cell-specific expression profile compared with that of the BrAOP2.1 and BrAOP2.2 genes. Quantitative real-time reverse transcription-PCR assays demonstrated that BrAOP2.1 showed a slightly different pattern of expression in below-ground tissue at the seedling stage and in the silique at the reproductive stage compared with BrAOP2.2 and BrAOP2.3 genes in B. rapa. Taken together, our results revealed that all three BrAOP2 paralogues are active in B. rapa but have functionally diverged. PMID:26188204

  17. BjuB.CYP79F1 Regulates Synthesis of Propyl Fraction of Aliphatic Glucosinolates in Oilseed Mustard Brassica juncea: Functional Validation through Genetic and Transgenic Approaches

    PubMed Central

    Sharma, Manisha; Mukhopadhyay, Arundhati; Gupta, Vibha; Pental, Deepak; Pradhan, Akshay K.

    2016-01-01

    Among the different types of methionine-derived aliphatic glucosinolates (GS), sinigrin (2-propenyl), the final product in 3C GS biosynthetic pathway is considered very important as it has many pharmacological and therapeutic properties. In Brassica species, the candidate gene regulating synthesis of 3C GS remains ambiguous. Earlier reports of GSL-PRO, an ortholog of Arabidopsis thaliana gene At1g18500 as a probable candidate gene responsible for 3C GS biosynthesis in B. napus and B. oleracea could not be validated in B. juncea through genetic analysis. In this communication, we report the isolation and characterization of the gene CYP79F1, an ortholog of A. thaliana gene At1g16410 that is involved in the first step of core GS biosynthesis. The gene CYP79F1 in B. juncea showed presence-absence polymorphism between lines Varuna that synthesizes sinigrin and Heera virtually free from sinigrin. Using this presence-absence polymorphism, CYP79F1 was mapped to the previously mapped 3C GS QTL region (J16Gsl4) in the LG B4 of B. juncea. In Heera, the gene was observed to be truncated due to an insertion of a ~4.7 kb TE like element leading to the loss of function of the gene. Functional validation of the gene was carried out through both genetic and transgenic approaches. An F2 population segregating only for the gene CYP79F1 and the sinigrin phenotype showed perfect co-segregation. Finally, genetic transformation of a B. juncea line (QTL-NIL J16Gsl4) having high seed GS but lacking sinigrin with the wild type CYP79F1 showed the synthesis of sinigrin validating the role of CYP79F1 in regulating the synthesis of 3C GS in B. juncea. PMID:26919200

  18. Molecular characterization of BrMYB28 and BrMYB29 paralogous transcription factors involved in the regulation of aliphatic glucosinolate profiles in Brassica rapa ssp. pekinensis.

    PubMed

    Baskar, Venkidasamy; Park, Se Won

    2015-07-01

    Glucosinolates (GSL) are one of the major secondary metabolites of the Brassicaceae family. In the present study, we aim at characterizing the multiple paralogs of aliphatic GSL regulators, such as BrMYB28 and BrMYB29 genes in Brassica rapa ssp. pekinensis, by quantitative real-time PCR (qRT-PCR) analysis in different tissues and at various developmental stages. An overlapping gene expression pattern between the BrMYBs as well as their downstream genes (DSGs) was found at different developmental stages. Among the BrMYB28 and BrMYB29 paralogous genes, the BrMYB28.3 and BrMYB29.1 genes were dominantly expressed in most of the developmental stages, compared to the other paralogs of the BrMYB genes. Furthermore, the differential expression pattern of the BrMYBs was observed under various stress treatments. Interestingly, BrMYB28.2 showed the least expression in most developmental stages, while its expression was remarkably high in different stress conditions. More specifically, the BrMYB28.2, BrMYB28.3, and BrMYB29.1 genes were highly responsive to various abiotic and biotic stresses, further indicating their possible role in stress tolerance. Moreover, the in silico cis motif analysis in the upstream regulatory regions of BrMYBs showed the presence of various putative stress-specific motifs, which further indicated their responsiveness to biotic and abiotic stresses. These observations suggest that the dominantly expressed BrMYBs, both in different developmental stages and under various stress treatments (BrMYB28.3 and BrMYB29.1), may be potential candidate genes for altering the GSL level through genetic modification studies in B. rapa ssp. pekinensis. PMID:26043798

  19. Glucose enhances indolic glucosinolate biosynthesis without reducing primary sulfur assimilation

    PubMed Central

    Miao, Huiying; Cai, Congxi; Wei, Jia; Huang, Jirong; Chang, Jiaqi; Qian, Hongmei; Zhang, Xin; Zhao, Yanting; Sun, Bo; Wang, Bingliang; Wang, Qiaomei

    2016-01-01

    The effect of glucose as a signaling molecule on induction of aliphatic glucosinolate biosynthesis was reported in our former study. Here, we further investigated the regulatory mechanism of indolic glucosinolate biosynthesis by glucose in Arabidopsis. Glucose exerted a positive influence on indolic glucosinolate biosynthesis, which was demonstrated by induced accumulation of indolic glucosinolates and enhanced expression of related genes upon glucose treatment. Genetic analysis revealed that MYB34 and MYB51 were crucial in maintaining the basal indolic glucosinolate accumulation, with MYB34 being pivotal in response to glucose signaling. The increased accumulation of indolic glucosinolates and mRNA levels of MYB34, MYB51, and MYB122 caused by glucose were inhibited in the gin2-1 mutant, suggesting an important role of HXK1 in glucose-mediated induction of indolic glucosinolate biosynthesis. In contrast to what was known on the function of ABI5 in glucose-mediated aliphatic glucosinolate biosynthesis, ABI5 was not required for glucose-induced indolic glucosinolate accumulation. In addition, our results also indicated that glucose-induced glucosinolate accumulation was due to enhanced sulfur assimilation instead of directed sulfur partitioning into glucosinolate biosynthesis. Thus, our data provide new insights into molecular mechanisms underlying glucose-regulated glucosinolate biosynthesis. PMID:27549907

  20. Glucose enhances indolic glucosinolate biosynthesis without reducing primary sulfur assimilation.

    PubMed

    Miao, Huiying; Cai, Congxi; Wei, Jia; Huang, Jirong; Chang, Jiaqi; Qian, Hongmei; Zhang, Xin; Zhao, Yanting; Sun, Bo; Wang, Bingliang; Wang, Qiaomei

    2016-01-01

    The effect of glucose as a signaling molecule on induction of aliphatic glucosinolate biosynthesis was reported in our former study. Here, we further investigated the regulatory mechanism of indolic glucosinolate biosynthesis by glucose in Arabidopsis. Glucose exerted a positive influence on indolic glucosinolate biosynthesis, which was demonstrated by induced accumulation of indolic glucosinolates and enhanced expression of related genes upon glucose treatment. Genetic analysis revealed that MYB34 and MYB51 were crucial in maintaining the basal indolic glucosinolate accumulation, with MYB34 being pivotal in response to glucose signaling. The increased accumulation of indolic glucosinolates and mRNA levels of MYB34, MYB51, and MYB122 caused by glucose were inhibited in the gin2-1 mutant, suggesting an important role of HXK1 in glucose-mediated induction of indolic glucosinolate biosynthesis. In contrast to what was known on the function of ABI5 in glucose-mediated aliphatic glucosinolate biosynthesis, ABI5 was not required for glucose-induced indolic glucosinolate accumulation. In addition, our results also indicated that glucose-induced glucosinolate accumulation was due to enhanced sulfur assimilation instead of directed sulfur partitioning into glucosinolate biosynthesis. Thus, our data provide new insights into molecular mechanisms underlying glucose-regulated glucosinolate biosynthesis. PMID:27549907

  1. Identification and expression analysis of glucosinolate biosynthetic genes and estimation of glucosinolate contents in edible organs of Brassica oleracea subspecies.

    PubMed

    Yi, Go-Eun; Robin, Arif Hasan Khan; Yang, Kiwoung; Park, Jong-In; Kang, Jong-Goo; Yang, Tae-Jin; Nou, Ill-Sup

    2015-01-01

    Glucosinolates are anti-carcinogenic, anti-oxidative biochemical compounds that defend plants from insect and microbial attack. Glucosinolates are abundant in all cruciferous crops, including all vegetable and oilseed Brassica species. Here, we studied the expression of glucosinolate biosynthesis genes and determined glucosinolate contents in the edible organs of a total of 12 genotypes of Brassica oleracea: three genotypes each from cabbage, kale, kohlrabi and cauliflower subspecies. Among the 81 genes analyzed by RT-PCR, 19 are transcription factor-related, two different sets of 25 genes are involved in aliphatic and indolic biosynthesis pathways and the rest are breakdown-related. The expression of glucosinolate-related genes in the stems of kohlrabi was remarkably different compared to leaves of cabbage and kale and florets of cauliflower as only eight genes out of 81 were expressed in the stem tissues of kohlrabi. In the stem tissue of kohlrabi, only one aliphatic transcription factor-related gene, Bol036286 (MYB28) and one indolic transcription factor-related gene, Bol030761 (MYB51), were expressed. The results indicated the expression of all genes is not essential for glucosinolate biosynthesis. Using HPLC analysis, a total of 16 different types of glucosinolates were identified in four subspecies, nine of them were aliphatic, four of them were indolic and one was aromatic. Cauliflower florets measured the highest number of 14 glucosinolates. Among the aliphatic glucosinolates, only gluconapin was found in the florets of cauliflower. Glucoiberverin and glucobrassicanapin contents were the highest in the stems of kohlrabi. The indolic methoxyglucobrassicin and aromatic gluconasturtiin accounted for the highest content in the florets of cauliflower. A further detailed investigation and analyses is required to discern the precise roles of each of the genes for aliphatic and indolic glucosinolate biosynthesis in the edible organs. PMID:26205053

  2. Glucosinolate Desulfation by the Phloem-Feeding Insect Bemisia tabaci.

    PubMed

    Malka, Osnat; Shekhov, Anton; Reichelt, Michael; Gershenzon, Jonathan; Vassão, Daniel Giddings; Morin, Shai

    2016-03-01

    Glucosinolates are plant secondary defense metabolites confined nearly exclusively to the order Brassicales. Upon tissue rupture, glucosinolates are hydrolyzed to various bioactive breakdown products by the endogenous plant enzyme myrosinase. As the feeding of chewing insect herbivores is associated with plant tissue damage, these insects have developed several independent strategies for coping with the glucosinolate-myrosinase defense system. On the other hand, our knowledge of how phloem-feeding insects interact with the glucosinolate-myrosinase system is much more limited. In fact, phloem feeders might avoid contact with myrosinase altogether so their susceptibility to intoxication by glucosinolate hydrolysis products is unclear. Previous studies utilizing Arabidopsis thaliana plants accumulating high levels of aliphatic- or indolic-glucosinolates indicated that both glucosinolate groups have moderate negative effects on the reproductive performance of Bemisia tabaci, a generalist phloem-feeding insect. To get a deeper understanding of the interaction between B. tabaci and glucosinolate-defended plants, adults were allowed to feed on artificial diet containing intact glucosinolates or on Brussels sprout and A. thaliana plants, and their honeydew was analyzed for the presence of possible metabolites. We found that B. tabaci is capable of cleaving off the sulfate group of intact glucosinolates, producing desulfoglucosinolates that cannot be activated by myrosinases, a mechanism described to date only in several chewing insect herbivores. The presence of desulfated glucosinolates in the honeydew of a generalist phloem-feeder may indicate the necessity to detoxify glucosinolates, likely due to some level of cellular damage during feeding, which results in glucosinolate activation, or as a mechanism to circumvent the non-enzymatic breakdown of indolic glucosinolates. PMID:26961756

  3. Glucosinolates in Moringa stenopetala.

    PubMed

    Mekonnen, Yalemtsehay; Dräger, Birgit

    2003-04-01

    Bio-guided fractionation of seed extracts from Moringa stenopetala resulted in a myrosinase hydrolysis product, 5,5-dimethyloxazolidine-2-thione. It is formed from the glucosinolate glucoconringiin, which was identified together with O-(rhamnopyranosyloxy)benzyl glucosinolate from M. stenopetala for the first time. The glucosinolates in seeds, leaves and roots of M. stenopetala were quantified as des-sulphoglucosinolate by HPLC. The seeds without testa contained the highest concentration of glucoconringiin and of O-(rhamnopyranosyloxy)benzyl glucosinolate within the plant, 3 % and 19 % of dry mass, respectively. Abbreviations. GLS:glucosinolate GC:glucoconringiin RB-GLS: O-(rhamnopyranosyloxy)benzyl glucosinolate PMID:12709911

  4. Biotic elicitors and mechanical damage modulate glucosinolate accumulation by co-ordinated interplay of glucosinolate biosynthesis regulators in polyploid Brassica juncea.

    PubMed

    Augustine, Rehna; Bisht, Naveen C

    2015-09-01

    Glucosinolates are nitrogen and sulfur containing secondary metabolites found mainly in the Brassicaceae. They function as plant defense compounds against a broad spectrum of pathogens and pests. Since these molecules form part of the plant defense mechanism, glucosinolate biosynthesis may be modulated by environmental signals leading to activation of a biological stress response. In the current study, we have mimicked such conditions by exogenously applying biotic elicitors such as methyl jasmonate, salicylic acid, glucose and mechanical injury in Brassica juncea seedling over a time course experiment. We found that total glucosinolates over-accumulated under these stress conditions with maximum accumulation observed 24h post treatment. Indole glucosinolates like 1-methoxy-indol-3-ylmethyl and its precursor indol-3-methyl glucosinolates showed a more significant induction compared to aliphatic glucosinolates thereby suggesting a prominent role of indole glucosinolates during plant defense response in B. juncea seedlings. In contrast, the higher amounts of aliphatic glucosinolates were less regulated by the tested biotic elicitors in B. juncea. Expression profiling of multiple homologs of key transcriptional regulators of glucosinolate biosynthesis further showed that a complex interplay of these regulators exists in polyploid B. juncea where they exert co-ordinated and overlapping effects toward altering glucosinolate accumulation. This study has a significant role toward understanding and augmenting plant defense mechanisms in B. juncea, a globally important oilseed crop of genus Brassica. PMID:26057228

  5. Expression Profiling of Glucosinolate Biosynthetic Genes in Brassica oleracea L. var. capitata Inbred Lines Reveals Their Association with Glucosinolate Content.

    PubMed

    Robin, Arif Hasan Khan; Yi, Go-Eun; Laila, Rawnak; Yang, Kiwoung; Park, Jong-In; Kim, Hye Ran; Nou, Ill-Sup

    2016-01-01

    Glucosinolates are the biochemical compounds that provide defense to plants against pathogens and herbivores. In this study, the relative expression level of 48 glucosinolate biosynthesis genes was explored in four morphologically-different cabbage inbred lines by qPCR analysis. The content of aliphatic and indolic glucosinolate molecules present in those cabbage lines was also estimated by HPLC analysis. The possible association between glucosinolate accumulation and related gene expression level was explored by principal component analysis (PCA). The genotype-dependent variation in the relative expression level of different aliphatic and indolic glucosinolate biosynthesis genes is the novel result of this study. A total of eight different types of glucosinolates, including five aliphatic and three indolic glucosinolates, was detected in four cabbage lines. Three inbred lines BN3383, BN4059 and BN4072 had no glucoraphanin, sinigrin and gluconapin detected, but the inbred line BN3273 had these three aliphatic glucosinolate compounds. PCA revealed that a higher expression level of ST5b genes and lower expression of GSL-OH was associated with the accumulation of these three aliphatic glucosinolate compounds. PCA further revealed that comparatively higher accumulation of neoglucobrassicin in the inbred line, BN4072, was associated with a high level of expression of MYB34 (Bol017062) and CYP81F1 genes. The Dof1 and IQD1 genes probably trans-activated the genes related to biosynthesis of glucoerucin and methoxyglucobrassicin for their comparatively higher accumulation in the BN4059 and BN4072 lines compared to the other two lines, BN3273 and BN3383. A comparatively higher progoitrin level in BN3273 was probably associated with the higher expression level of the GSL-OH gene. The cabbage inbred line BN3383 accounted for the significantly higher relative expression level for the 12 genes out of 48, but this line had comparatively lower total glucosinolates detected

  6. Targeted silencing of BjMYB28 transcription factor gene directs development of low glucosinolate lines in oilseed Brassica juncea.

    PubMed

    Augustine, Rehna; Mukhopadhyay, Arundhati; Bisht, Naveen C

    2013-09-01

    Brassica juncea (Indian mustard), a globally important oilseed crop, contains relatively high amount of seed glucosinolates ranging from 80 to 120 μmol/g dry weight (DW). One of the major breeding objectives in oilseed Brassicas is to improve the seed-meal quality through the development of low-seed-glucosinolate lines (<30 μmol/g DW), as high amounts of certain seed glucosinolates are known to be anti-nutritional and reduce the meal palatability. Here, we report the development of transgenic B. juncea lines having seed glucosinolates as low as 11.26 μmol/g DW, through RNAi-based targeted suppression of BjMYB28, a R2R3-MYB transcription factor family gene involved in aliphatic glucosinolate biosynthesis. Targeted silencing of BjMYB28 homologs provided significant reduction in the anti-nutritional aliphatic glucosinolates fractions, without altering the desirable nonaliphatic glucosinolate pool, both in leaves and seeds of transgenic plants. Molecular characterization of single-copy, low glucosinolate homozygous lines confirmed significant down-regulation of BjMYB28 homologs vis-à-vis enhanced accumulation of BjMYB28-specific siRNA pool. Consequently, these low glucosinolate lines also showed significant suppression of genes involved in aliphatic glucosinolate biosynthesis. The low glucosinolate trait was stable in subsequent generations of the transgenic lines with no visible off-target effects on plant growth and development. Various seed quality parameters including fatty acid composition, oil content, protein content and seed weight of the low glucosinolate lines also remained unaltered, when tested under containment conditions in the field. Our results indicate that targeted silencing of a key glucosinolate transcriptional regulator MYB28 has huge potential for reducing the glucosinolates content and improving the seed-meal quality of oilseed Brassica crops. PMID:23721233

  7. Natural Variation in MAM Within and Between Populations of Arabidopsis lyrata Determines Glucosinolate Phenotype

    PubMed Central

    Heidel, Andrew J.; Clauss, Maria J.; Kroymann, Juergen; Savolainen, Outi; Mitchell-Olds, Thomas

    2006-01-01

    The genetic variation that underlies the glucosinolate phenotype of Arabidopsis lyrata ssp. petraea was investigated between and within populations. A candidate glucosinolate biosynthetic locus (MAM, containing methylthioalkylmalate synthase genes) was mapped in A. lyrata to a location on linkage group 6 corresponding to the homologous location for MAM in A. thaliana. In A. thaliana MAM is responsible for side chain elongation in aliphatic glucosinolates, and the MAM phenotype can be characterized by the ratios of long- to short-chain glucosinolates. A quantitative trait loci (QTL) analysis of glucosinolate ratios in an A. lyrata interpopulation cross found one QTL at MAM. Additional QTL were identified for total indolic glucosinolates and for the ratio of aliphatic to indolic glucosinolates. MAM was then used as the candidate gene for a within-population cosegregation analysis in a natural A. lyrata population from Germany. Extensive variation in microsatellite markers at MAM was found and this variation cosegregated with the same glucosinolate ratios as in the QTL study. The combined results indicate that both between- and within-population genetic variation in the MAM region determines phenotypic variation in glucosinolate side chains in A. lyrata. PMID:16702431

  8. The Effects of Glucosinolates and Their Breakdown Products on Necrotrophic Fungi

    PubMed Central

    Barda, Omer; Levy, Maggie

    2013-01-01

    Glucosinolates are a diverse class of S- and N-containing secondary metabolites that play a variety of roles in plant defense. In this study, we used Arabidopsis thaliana mutants that contain different amounts of glucosinolates and glucosinolate-breakdown products to study the effects of these phytochemicals on phytopathogenic fungi. We compared the fungus Botrytis cinerea, which infects a variety of hosts, with the Brassicaceae-specific fungus Alternaria brassicicola. B. cinerea isolates showed variable composition-dependent sensitivity to glucosinolates and their hydrolysis products, while A. brassicicola was more strongly affected by aliphatic glucosinolates and isothiocyanates as decomposition products. We also found that B. cinerea stimulates the accumulation of glucosinolates to a greater extent than A. brassicicola. In our work with A. brassicicola, we found that the type of glucosinolate-breakdown product is more important than the type of glucosinolate from which that product was derived, as demonstrated by the sensitivity of the Ler background and the sensitivity gained in Col-0 plants expressing epithiospecifier protein both of which accumulate simple nitrile and epithionitriles, but not isothiocyanates. Furthermore, in vivo, hydrolysis products of indole glucosinolates were found to be involved in defense against B. cinerea, but not in the host response to A. brassicicola. We suggest that the Brassicaceae-specialist A. brassicicola has adapted to the presence of indolic glucosinolates and can cope with their hydrolysis products. In contrast, some isolates of the generalist B. cinerea are more sensitive to these phytochemicals. PMID:23940639

  9. Effect of growth temperature on glucosinolate profiles in Arabidopsis thaliana accessions.

    PubMed

    Kissen, Ralph; Eberl, Franziska; Winge, Per; Uleberg, Eivind; Martinussen, Inger; Bones, Atle M

    2016-10-01

    Glucosinolates are plant secondary metabolites with important roles in plant defence against pathogens and pests and are also known for their health benefits. Understanding how environmental factors affect the level and composition of glucosinolates is therefore of importance in the perspective of climate change. In this study we analysed glucosinolates in Arabidopsis thaliana accessions when grown at constant standard (21 °C), moderate (15 °C) and low (9 °C) temperatures during three generations. In most of the tested accessions moderate and pronounced chilling temperatures led to higher levels of glucosinolates, especially aliphatic glucosinolates. Which temperature yielded the highest glucosinolate levels was accession-dependent. Transcriptional profiling revealed also accession-specific gene responses, but only a limited correlation between changes in glucosinolate-related gene expression and glucosinolate levels. Different growth temperatures in one generation did not consistently affect glucosinolate composition in subsequent generations, hence a clear transgenerational effect of temperature on glucosinolates was not observed. PMID:27319377

  10. Screening crucifer seeds as sources of specific intact glucosinolates using ion-pair high-performance liquid chromatography negative ion electrospray mass spectrometry.

    PubMed

    Bennett, Richard N; Mellon, Fred A; Kroon, Paul A

    2004-02-11

    Seeds, of either commercial crucifer crops or some wild and weed relatives, were screened for intact glucosinolates using a previously developed ion-pair LC-MS method. This method, in contrast to GC-MS techniques, ensures the accurate measurement of all classes of glucosinolates. Many crucifer seeds contained very high concentrations of glucosinolates with low concentrations of additional pigments and secondary metabolites. The other common seed metabolites were cinnamoylcholine esters, for example, sinapine. Glucosinolates derived from homologues of l-methionine were characteristic of Brassica and related crucifer species. In addition, significant concentrations of 4-hydroxy-3-indolylmethylglucosinolate were found in the majority of Brassica species. Wild and weed species often had relatively simple glucosinolate profiles: either a single glucosinolate or a predominant glucosinolate together with trace amounts of others. Species identified with seed glucosinolate profiles suitable for purification included various Alyssum, Erysimum, and Iberis species for 3-methythiopropyl-glucosinolate and 3-methylsulfinylpropyl-glucosinolate and various Alyssum, Erysimum, and Lepidium species with very high concentrations of C4-C6 aliphatic glucosinolates. Seeds of Arabis, Barbarea, Lepidium, Moringa, and Sinapis species were good sources of aromatic glucosinolates, and Azima tetracantha was a good source for N-methoxy-3-indolylmethyl-glucosinolate. MS data are reported for all of the intact glucosinolates detected from the screening process. PMID:14759128

  11. Plant plasma membrane aquaporins in natural vesicles as potential stabilizers and carriers of glucosinolates.

    PubMed

    Martínez-Ballesta, Maria Del Carmen; Pérez-Sánchez, Horacio; Moreno, Diego A; Carvajal, Micaela

    2016-07-01

    Their biodegradable nature and ability to target cells make biological vesicles potential nanocarriers for bioactives delivery. In this work, the interaction between proteoliposomes enriched in aquaporins derived from broccoli plants and the glucosinolates was evaluated. The vesicles were stored at different temperatures and their integrity was studied. Determination of glucosinolates, showed that indolic glucosinolates were more sensitive to degradation in aqueous solution than aliphatic glucosinolates. Glucoraphanin was stabilized by leaf and root proteoliposomes at 25°C through their interaction with aquaporins. An extensive hydrogen bond network, including different aquaporin residues, and hydrophobic interactions, as a consequence of the interaction between the linear alkane chain of glucoraphanin and Glu31 and Leu34 protein residues, were established as the main stabilizing elements. Combined our results showed that plasma membrane vesicles from leaf and root tissues of broccoli plants may be considered as suitable carriers for glucosinolate which stabilization can be potentially attributed to aquaporins. PMID:27022872

  12. Glucosinolates from Host Plants Influence Growth of the Parasitic Plant Cuscuta gronovii and Its Susceptibility to Aphid Feeding.

    PubMed

    Smith, Jason D; Woldemariam, Melkamu G; Mescher, Mark C; Jander, Georg; De Moraes, Consuelo M

    2016-09-01

    Parasitic plants acquire diverse secondary metabolites from their hosts, including defense compounds that target insect herbivores. However, the ecological implications of this phenomenon, including the potential enhancement of parasite defenses, remain largely unexplored. We studied the translocation of glucosinolates from the brassicaceous host plant Arabidopsis (Arabidopsis thaliana) into parasitic dodder vines (Convolvulaceae; Cuscuta gronovii) and its effects on the parasite itself and on dodder-aphid interactions. Aliphatic and indole glucosinolates reached concentrations in parasite tissues higher than those observed in corresponding host tissues. Dodder growth was enhanced on cyp79B2 cyp79B3 hosts (without indole glucosinolates) but inhibited on atr1D hosts (with elevated indole glucosinolates) relative to wild-type hosts, which responded to parasitism with localized elevation of indole and aliphatic glucosinolates. These findings implicate indole glucosinolates in defense against parasitic plants. Rates of settling and survival on dodder vines by pea aphids (Acyrthosiphon pisum) were reduced significantly when dodder parasitized glucosinolate-producing hosts (wild type and atr1D) compared with glucosinolate-free hosts (cyp79B2 cyp79B3 myb28 myb29). However, settling and survival of green peach aphids (Myzus persicae) were not affected. M. persicae population growth was actually reduced on dodder parasitizing glucosinolate-free hosts compared with wild-type or atr1D hosts, even though stems of the former contain less glucosinolates and more amino acids. Strikingly, this effect was reversed when the aphids fed directly upon Arabidopsis, which indicates an interactive effect of parasite and host genotype on M. persicae that stems from host effects on dodder. Thus, our findings indicate that glucosinolates may have both direct and indirect effects on dodder-feeding herbivores. PMID:27482077

  13. Camelina sativa defatted seed meal contains both alkyl sulfinyl glucosinolates and quercetin that synergize bioactivity

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Camelina sativa L. Crantz is under development as a novel oil-seed crop, yet bioefficacy of camelina phytochemicals is unknown. Defatted camelina seed meal contains two major aliphatic glucosinolates (GSL), glucoarabin (9-(methylsulfinyl)nonylglucosinolate; GSL 9) and glucocamelinin (10-(methylsulfi...

  14. Identification of metabolic QTLs and candidate genes for glucosinolate synthesis in Brassica oleracea leaves, seeds and flower buds.

    PubMed

    Sotelo, Tamara; Soengas, Pilar; Velasco, Pablo; Rodríguez, Víctor M; Cartea, María Elena

    2014-01-01

    Glucosinolates are major secondary metabolites found in the Brassicaceae family. These compounds play an essential role in plant defense against biotic and abiotic stresses, but more interestingly they have beneficial effects on human health. We performed a genetic analysis in order to identify the genome regions regulating glucosinolates biosynthesis in a DH mapping population of Brassica oleracea. In order to obtain a general overview of regulation in the whole plant, analyses were performed in the three major organs where glucosinolates are synthesized (leaves, seeds and flower buds). Eighty two significant QTLs were detected, which explained a broad range of variability in terms of individual and total glucosinolate (GSL) content. A meta-analysis rendered eighteen consensus QTLs. Thirteen of them regulated more than one glucosinolate and its content. In spite of the considerable variability of glucosinolate content and profiles across the organ, some of these consensus QTLs were identified in more than one tissue. Consensus QTLs control the GSL content by interacting epistatically in complex networks. Based on in silico analysis within the B. oleracea genome along with synteny with Arabidopsis, we propose seven major candidate loci that regulate GSL biosynthesis in the Brassicaceae family. Three of these loci control the content of aliphatic GSL and four of them control the content of indolic glucosinolates. GSL-ALK plays a central role in determining aliphatic GSL variation directly and by interacting epistatically with other loci, thus suggesting its regulatory effect. PMID:24614913

  15. ANALYSIS OF GLUCOSINOLATES AND GLUCOSINOLATE DEGRADATION PRODUCTS IN SPROUTING BROCCOLI SEEDS

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Total glucosinolate content and glucosinolate degradation products were examined in unsprouted `Marathon' broccoli (Brassica oleracea L., Italica group) seeds and in 1-, 2-, 3-, 5-, 7-, and 10-day-old sprouts. Glucosinolates identified were glucoiberin, glucoraphanin, gluconapin, glucoiberverin, 4-...

  16. Genes of primary sulfate assimilation are part of the glucosinolate biosynthetic network in Arabidopsis thaliana.

    PubMed

    Yatusevich, Ruslan; Mugford, Sarah G; Matthewman, Colette; Gigolashvili, Tamara; Frerigmann, Henning; Delaney, Sean; Koprivova, Anna; Flügge, Ulf-Ingo; Kopriva, Stanislav

    2010-04-01

    Glucosinolates are plant secondary metabolites involved in responses to biotic stress. The final step of their synthesis is the transfer of a sulfo group from 3'-phosphoadenosine 5'-phosphosulfate (PAPS) onto a desulfo precursor. Thus, glucosinolate synthesis is linked to sulfate assimilation. The sulfate donor for this reaction is synthesized from sulfate in two steps catalyzed by ATP sulfurylase (ATPS) and adenosine 5'-phosphosulfate kinase (APK). Here we demonstrate that R2R3-MYB transcription factors, which are known to regulate both aliphatic and indolic glucosinolate biosynthesis in Arabidopsis thaliana, also control genes of primary sulfate metabolism. Using trans-activation assays we found that two isoforms of APK, APK1, and APK2, are regulated by both classes of glucosinolate MYB transcription factors; whereas two ATPS genes, ATPS1 and ATPS3, are differentially regulated by these two groups of MYB factors. In addition, we show that the adenosine 5'-phosphosulfate reductases APR1, APR2, and APR3, which participate in primary sulfate reduction, are also activated by the MYB factors. These observations were confirmed by analysis of transgenic lines with modulated expression levels of the glucosinolate MYB factors. The changes in transcript levels also affected enzyme activities, the thiol content and the sulfate reduction rate in some of the transgenic plants. Altogether the data revealed that the MYB transcription factors regulate genes of primary sulfate metabolism and that the genes involved in the synthesis of activated sulfate are part of the glucosinolate biosynthesis network. PMID:20042022

  17. Macroevolutionary patterns of glucosinolate defense and tests of defense-escalation and resource availability hypotheses.

    PubMed

    Cacho, N Ivalú; Kliebenstein, Daniel J; Strauss, Sharon Y

    2015-11-01

    We explored macroevolutionary patterns of plant chemical defense in Streptanthus (Brassicaceae), tested for evolutionary escalation of defense, as predicted by Ehrlich and Raven's plant-herbivore coevolutionary arms-race hypothesis, and tested whether species inhabiting low-resource or harsh environments invest more in defense, as predicted by the resource availability hypothesis (RAH). We conducted phylogenetically explicit analyses using glucosinolate profiles, soil nutrient analyses, and microhabitat bareness estimates across 30 species of Streptanthus inhabiting varied environments and soils. We found weak to moderate phylogenetic signal in glucosinolate classes and no signal in total glucosinolate production; a trend toward evolutionary de-escalation in the numbers and diversity of glucosinolates, accompanied by an evolutionary increase in the proportion of aliphatic glucosinolates; some support for the RAH relative to soil macronutrients, but not relative to serpentine soil use; and that the number of glucosinolates increases with microhabitat bareness, which is associated with increased herbivory and drought. Weak phylogenetic signal in chemical defense has been observed in other plant systems. A more holistic approach incorporating other forms of defense might be necessary to confidently reject escalation of defense. That defense increases with microhabitat bareness supports the hypothesis that habitat bareness is an underappreciated selective force on plants in harsh environments. PMID:26192213

  18. Metabolic Profiling in Chinese Cabbage (Brassica rapa L. subsp. pekinensis) Cultivars Reveals that Glucosinolate Content Is Correlated with Carotenoid Content.

    PubMed

    Baek, Seung-A; Jung, Young-Ho; Lim, Sun-Hyung; Park, Sang Un; Kim, Jae Kwang

    2016-06-01

    A total of 38 bioactive compounds, including glucosinolates, carotenoids, tocopherols, sterols, and policosanols, were characterized from nine varieties of Chinese cabbage (Brassica rapa L. subsp. pekinensis) to determine their phytochemical diversity and analyze their abundance relationships. The metabolite profiles were evaluated with principal component analysis (PCA), Pearson correlation analysis, and hierarchical clustering analysis (HCA). PCA and HCA identified two distinct varieties of Chinese cabbage (Cheonsangcheonha and Waldongcheonha) with higher levels of glucosinolates and carotenoids. Pairwise comparisons of the 38 metabolites were calculated using Pearson correlation coefficients. The HCA, which used the correlation coefficients, clustered metabolites that are derived from closely related biochemical pathways. Significant correlations were discovered between chlorophyll and carotenoids. Additionally, aliphatic glucosinolate and carotenoid levels were positively correlated. The Cheonsangcheonha and Waldongcheonha varieties appear to be good candidates for breeding because they have high glucosinolate and carotenoid levels. PMID:27172980

  19. Atmospheric H2S and SO2 as sulfur source for Brassica juncea and Brassica rapa: impact on the glucosinolate composition

    PubMed Central

    Aghajanzadeh, Tahereh; Kopriva, Stanislav; Hawkesford, Malcolm J.; Koprivova, Anna; De Kok, Luit J.

    2015-01-01

    The impact of sulfate deprivation and atmospheric H2S and SO2 nutrition on the content and composition of glucosinolates was studied in Brassica juncea and B. rapa. Both species contained a number of aliphatic, aromatic and indolic glucosinolates. The total glucosinolate content was more than 5.5-fold higher in B. juncea than in B. rapa, which could solely be attributed to the presence of high levels of sinigrin, which was absent in the latter species. Sulfate deprivation resulted in a strong decrease in the content and an altered composition of the glucosinolates of both species. Despite the differences in patterns in foliarly uptake and metabolism, their exposure hardly affected the glucosinolate composition of the shoot, both at sulfate-sufficient and sulfate-deprived conditions. This indicated that the glucosinolate composition in the shoot was hardly affected by differences in sulfur source (viz., sulfate, sulfite and sulfide). Upon sulfate deprivation, where foliarly absorbed H2S and SO2 were the sole sulfur source for growth, the glucosinolate composition of roots differed from sulfate-sufficient B. juncea and B. rapa, notably the fraction of the indolic glucosinolates was lower than that observed in sulfur-sufficient roots. PMID:26579170

  20. A Gene Controlling Variation in Arabidopsis Glucosinolate Composition Is Part of the Methionine Chain Elongation Pathway1

    PubMed Central

    Kroymann, Juergen; Textor, Susanne; Tokuhisa, Jim G.; Falk, Kimberly L.; Bartram, Stefan; Gershenzon, Jonathan; Mitchell-Olds, Thomas

    2001-01-01

    Arabidopsis and other Brassicaceae produce an enormous diversity of aliphatic glucosinolates, a group of methionine (Met)-derived plant secondary compounds containing a β-thio-glucose moiety, a sulfonated oxime, and a variable side chain. We fine-scale mapped GSL-ELONG, a locus controlling variation in the side-chain length of aliphatic glucosinolates. Within this locus, a polymorphic gene was identified that determines whether Met is extended predominantly by either one or by two methylene groups to produce aliphatic glucosinolates with either three- or four-carbon side chains. Two allelic mutants deficient in four-carbon side-chain glucosinolates were shown to contain independent missense mutations within this gene. In cell-free enzyme assays, a heterologously expressed cDNA from this locus was capable of condensing 2-oxo-4-methylthiobutanoic acid with acetyl-coenzyme A, the initial reaction in Met chain elongation. The gene methylthioalkylmalate synthase1 (MAM1) is a member of a gene family sharing approximately 60% amino acid sequence similarity with 2-isopropylmalate synthase, an enzyme of leucine biosynthesis that condenses 2-oxo-3-methylbutanoate with acetyl-coenzyme A. PMID:11706188

  1. Phyllotreta striolata flea beetles use host plant defense compounds to create their own glucosinolate-myrosinase system.

    PubMed

    Beran, Franziska; Pauchet, Yannick; Kunert, Grit; Reichelt, Michael; Wielsch, Natalie; Vogel, Heiko; Reinecke, Andreas; Svatoš, Aleš; Mewis, Inga; Schmid, Daniela; Ramasamy, Srinivasan; Ulrichs, Christian; Hansson, Bill S; Gershenzon, Jonathan; Heckel, David G

    2014-05-20

    The ability of a specialized herbivore to overcome the chemical defense of a particular plant taxon not only makes it accessible as a food source but may also provide metabolites to be exploited for communication or chemical defense. Phyllotreta flea beetles are adapted to crucifer plants (Brassicales) that are defended by the glucosinolate-myrosinase system, the so-called "mustard-oil bomb." Tissue damage caused by insect feeding brings glucosinolates into contact with the plant enzyme myrosinase, which hydrolyzes them to form toxic compounds, such as isothiocyanates. However, we previously observed that Phyllotreta striolata beetles themselves produce volatile glucosinolate hydrolysis products. Here, we show that P. striolata adults selectively accumulate glucosinolates from their food plants to up to 1.75% of their body weight and express their own myrosinase. By combining proteomics and transcriptomics, a gene responsible for myrosinase activity in P. striolata was identified. The major substrates of the heterologously expressed myrosinase were aliphatic glucosinolates, which were hydrolyzed with at least fourfold higher efficiency than aromatic and indolic glucosinolates, and β-O-glucosides. The identified beetle myrosinase belongs to the glycoside hydrolase family 1 and has up to 76% sequence similarity to other β-glucosidases. Phylogenetic analyses suggest species-specific diversification of this gene family in insects and an independent evolution of the beetle myrosinase from other insect β-glucosidases. PMID:24799680

  2. Interaction between plants and bacteria: glucosinolates and phyllospheric colonization of cruciferous vegetables by Enterobacter radicincitans DSM 16656.

    PubMed

    Schreiner, Monika; Krumbein, Angelika; Ruppel, Silke

    2009-01-01

    For determining interactive plant-bacterial effects between glucosinolates and phyllospheric colonization by a plant growth-promoting strain, Enterobacter radicincitans DSM 16656, in cruciferous vegetables, the extent of bacterial colonization was assessed in 5 cruciferous vegetables (Brassica juncea, Brassica campestris, Brassica oleracea var. capitata, Brassica rapa var. alboglabra, Nasturtium officinale) using a species-specific TaqMan probe and quantitative real-time PCR. Colonization ability of inoculated E. radicincitans in the phyllosphere of these species varied from inability to colonize B. rapa up to a very good colonization rate of B. campestris. In addition to morphological factors and other plant compounds, the colonization rate was affected by different individual aromatic and aliphatic glucosinolates and their concentration, revealing that both plant pathogens and plant growth-promoting bacteria were affected by glucosinolates in their colonization behavior. In contrast, after E. radicincitans inoculation neither the total nor the individual glucosinolate concentrations in the phyllosphere of the 5 cruciferous species were affected, indicating that the nonpathogenic E. radicincitans might cause only poor cell damage by metabolizing plant cell components and does not induce a plant defense response and thus subsequently an increased glucosinolate concentration in the phyllosphere. Moreover, E. radicincitans induced no stimulation of indole glucosinolate biosynthesis by additional bacterial auxin supply. PMID:19556746

  3. Behavior of glucosinolates in pickling cruciferous vegetables.

    PubMed

    Suzuki, Chise; Ohnishi-Kameyama, Mayumi; Sasaki, Keisuke; Murata, Takashi; Yoshida, Mitsuru

    2006-12-13

    Crucifer species, which include widely consumed vegetables, contain glucosinolates as secondary metabolites. Cruciferous vegetables are consumed in Japan in salt-preserved or pickled form as well as cooked and raw fresh vegetables. In this study, changes in contents of glucosinolates during the pickling process were investigated. 4-Methylthio-3-butenyl glucosinolate, a major glucosinolate in the root of Japanese radish, daikon (Raphanus sativus L.), was detected in pickled products with a short maturation period but not in those with a long maturation period. As a model pickling experiment, fresh watercress (Nasturtium officinale) and blanched watercress were soaked in 3% NaCl solution for 7 days. The results showed that the ratio of indole glucosinolates to total glucosinolates increased during the pickling process, whereas total glucosinolates decreased. Myrosinase digestion of glucosinolates in nozawana (Brassica rapa L.) indicated that indole glucosinolates, especially 4-methoxyglucobrassicin, were relatively resistant to the enzyme. The effect of pickling on glucosinolate content and the possible mechanism are discussed in view of degradation by myrosinase and synthetic reaction in response to salt stress or compression during the pickling process. PMID:17147429

  4. Lineage-specific evolution of Methylthioalkylmalate synthases (MAMs) involved in glucosinolates biosynthesis.

    PubMed

    Zhang, Jifang; Wang, Xiaobo; Cheng, Feng; Wu, Jian; Liang, Jianli; Yang, Wencai; Wang, Xiaowu

    2015-01-01

    Methylthioalkylmalate synthases (MAMs) encoded by MAM genes are central to the diversification of the glucosinolates, which are important secondary metabolites in Brassicaceae species. However, the evolutionary pathway of MAM genes is poorly understood. We analyzed the phylogenetic and synteny relationships of MAM genes from 13 sequenced Brassicaceae species. Based on these analyses, we propose that the syntenic loci of MAM genes, which underwent frequent tandem duplications, divided into two independent lineage-specific evolution routes and were driven by positive selection after the divergence from Aethionema arabicum. In the lineage I species Capsella rubella, Camelina sativa, Arabidopsis lyrata, and A. thaliana, the MAM loci evolved three tandem genes encoding enzymes responsible for the biosynthesis of aliphatic glucosinolates with different carbon chain-lengths. In lineage II species, the MAM loci encode enzymes responsible for the biosynthesis of short-chain aliphatic glucosinolates. Our proposed model of the evolutionary pathway of MAM genes will be useful for understanding the specific function of these genes in Brassicaceae species. PMID:25691886

  5. Lineage-specific evolution of Methylthioalkylmalate synthases (MAMs) involved in glucosinolates biosynthesis

    PubMed Central

    Zhang, Jifang; Wang, Xiaobo; Cheng, Feng; Wu, Jian; Liang, Jianli; Yang, Wencai; Wang, Xiaowu

    2015-01-01

    Methylthioalkylmalate synthases (MAMs) encoded by MAM genes are central to the diversification of the glucosinolates, which are important secondary metabolites in Brassicaceae species. However, the evolutionary pathway of MAM genes is poorly understood. We analyzed the phylogenetic and synteny relationships of MAM genes from 13 sequenced Brassicaceae species. Based on these analyses, we propose that the syntenic loci of MAM genes, which underwent frequent tandem duplications, divided into two independent lineage-specific evolution routes and were driven by positive selection after the divergence from Aethionema arabicum. In the lineage I species Capsella rubella, Camelina sativa, Arabidopsis lyrata, and A. thaliana, the MAM loci evolved three tandem genes encoding enzymes responsible for the biosynthesis of aliphatic glucosinolates with different carbon chain-lengths. In lineage II species, the MAM loci encode enzymes responsible for the biosynthesis of short-chain aliphatic glucosinolates. Our proposed model of the evolutionary pathway of MAM genes will be useful for understanding the specific function of these genes in Brassicaceae species. PMID:25691886

  6. The Defense Metabolite, Allyl Glucosinolate, Modulates Arabidopsis thaliana Biomass Dependent upon the Endogenous Glucosinolate Pathway

    PubMed Central

    Francisco, Marta; Joseph, Bindu; Caligagan, Hart; Li, Baohua; Corwin, Jason A.; Lin, Catherine; Kerwin, Rachel; Burow, Meike; Kliebenstein, Daniel J.

    2016-01-01

    Glucosinolates (GSLs) play an important role in plants as direct mediators of biotic and abiotic stress responses. Recent work is beginning to show that the GSLs can also inducing complex defense and growth networks. However, the physiological significance of these GSL-induced responses and the molecular mechanisms by which GSLs are sensed and/or modulate these responses are not understood. To identify these potential mechanisms within the plant and how they may relate to the endogenous GSLs, we tested the regulatory effect of exogenous allyl GSL application on growth and defense metabolism across sample of Arabidopsis thaliana accessions. We found that application of exogenous allyl GSL had the ability to initiate changes in plant biomass and accumulation of defense metabolites that genetically varied across accessions. This growth effect was related to the allyl GSL side-chain structure. Utilizing this natural variation and mutants in genes within the GSL pathway we could show that the link between allyl GSL and altered growth responses are dependent upon the function of known genes controlling the aliphatic GSL pathway. PMID:27313596

  7. Purification of glucosinolates from Camelina sativa seeds

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Camelina sativa L. Crantz defatted seed press cake contains a number of phytochemicals, including the flavonoid rutin (quercetin 3-O-rutinoside), an acylated quercetin glycoside, and three glucosinolates: glucoarabin (9-(methylsulfinyl)nonyl-glucosinolate) glucocamelinin (10-(methylsulfinyl)decyl-gl...

  8. Structural and functional evolution of isopropylmalate dehydrogenases in the leucine and glucosinolate pathways of Arabidopsis thaliana

    SciTech Connect

    He, Yan; Galant, Ashley; Pang, Qiuying; Strul, Johanna M.; Balogun, Sherifat F.; Jez, Joseph M.; Chen, Sixue

    2012-10-24

    The methionine chain-elongation pathway is required for aliphatic glucosinolate biosynthesis in plants and evolved from leucine biosynthesis. In Arabidopsis thaliana, three 3-isopropylmalate dehydrogenases (AtIPMDHs) play key roles in methionine chain-elongation for the synthesis of aliphatic glucosinolates (e.g. AtIPMDH1) and leucine (e.g. AtIPMDH2 and AtIPMDH3). Here we elucidate the molecular basis underlying the metabolic specialization of these enzymes. The 2.25 {angstrom} resolution crystal structure of AtIPMDH2 was solved to provide the first detailed molecular architecture of a plant IPMDH. Modeling of 3-isopropylmalate binding in the AtIPMDH2 active site and sequence comparisons of prokaryotic and eukaryotic IPMDH suggest that substitution of one active site residue may lead to altered substrate specificity and metabolic function. Site-directed mutagenesis of Phe-137 to a leucine in AtIPMDH1 (AtIPMDH1-F137L) reduced activity toward 3-(2'-methylthio)ethylmalate by 200-fold, but enhanced catalytic efficiency with 3-isopropylmalate to levels observed with AtIPMDH2 and AtIPMDH3. Conversely, the AtIPMDH2-L134F and AtIPMDH3-L133F mutants enhanced catalytic efficiency with 3-(2'-methylthio)ethylmalate {approx}100-fold and reduced activity for 3-isopropylmalate. Furthermore, the altered in vivo glucosinolate profile of an Arabidopsis ipmdh1 T-DNA knock-out mutant could be restored to wild-type levels by constructs expressing AtIPMDH1, AtIPMDH2-L134F, or AtIPMDH3-L133F, but not by AtIPMDH1-F137L. These results indicate that a single amino acid substitution results in functional divergence of IPMDH in planta to affect substrate specificity and contributes to the evolution of specialized glucosinolate biosynthesis from the ancestral leucine pathway.

  9. Glucosinolate Accumulation and Related Gene Expression in Pak Choi (Brassica rapa L. ssp. chinensis var. communis [N. Tsen & S.H. Lee] Hanelt) in Response to Insecticide Application.

    PubMed

    Zhu, Biao; Yang, Jing; He, Yong; Zang, Yunxiang; Zhu, Zhujun

    2015-11-11

    Glucosinolates and their breakdown products are well-known for their cancer-chemoprotective functions and biocidal activities against pathogens and generalist herbivores. Insecticides are commonly used in the production of pak choi (Brassica rapa L. ssp. chinensis var. communis [N. Tsen & S.H. Lee] Hanelt). We studied the effects of four commonly used insecticides, namely, β-cypermethrin, acephate, pymetrozine, and imidacloprid, on glucosinolate metabolism in pak choi. All insecticides significantly increased both the transcription of glucosinolate biosynthetic genes and the aliphatic and total glucosinolate accumulations in pak choi. β-Cypermethrin and acephate caused gradual and continuous up-regulation of gene expression from 0.5 to 24 h after treatment, whereas pymetrozine and imidacloprid did so more rapidly, reaching a peak at 1 h and returning to normal at 3 h. Our findings indicate that the four insecticides affect glucosinolate metabolism in pak choi plants to various degrees and suggest that glucosinolates may be involved in plant insecticide metabolism. PMID:26485123

  10. Elucidating the role of transport processes in leaf glucosinolate distribution.

    PubMed

    Madsen, Svend Roesen; Olsen, Carl Erik; Nour-Eldin, Hussam Hassan; Halkier, Barbara Ann

    2014-11-01

    In Arabidopsis (Arabidopsis thaliana), a strategy to defend its leaves against herbivores is to accumulate glucosinolates along the midrib and at the margin. Although it is generally assumed that glucosinolates are synthesized along the vasculature in an Arabidopsis leaf, thereby suggesting that the margin accumulation is established through transport, little is known about these transport processes. Here, we show through leaf apoplastic fluid analysis and glucosinolate feeding experiments that two glucosinolate transporters, GTR1 and GTR2, essential for long-distance transport of glucosinolates in Arabidopsis, also play key roles in glucosinolate allocation within a mature leaf by effectively importing apoplastically localized glucosinolates into appropriate cells. Detection of glucosinolates in root xylem sap unambiguously shows that this transport route is involved in root-to-shoot glucosinolate allocation. Detailed leaf dissections show that in the absence of GTR1 and GTR2 transport activity, glucosinolates accumulate predominantly in leaf margins and leaf tips. Furthermore, we show that glucosinolates accumulate in the leaf abaxial epidermis in a GTR-independent manner. Based on our results, we propose a model for how glucosinolates accumulate in the leaf margin and epidermis, which includes symplasmic movement through plasmodesmata, coupled with the activity of putative vacuolar glucosinolate importers in these peripheral cell layers. PMID:25209984

  11. Dynamics of glucosinolate-myrosinase system during Plutella xylostella interaction to a novel host Lepidium latifolium L.

    PubMed

    Kaur, Tarandeep; Bhat, Rohini; Khajuria, Manu; Vyas, Ruchika; Kumari, Anika; Nadda, Gireesh; Vishwakarma, Ram; Vyas, Dhiraj

    2016-09-01

    Plutella xylostella L. is a notorious pest of cruciferous crops causing worldwide losses of $4-5 billion per year. Developing classical biological control to this pest include an introduction of host plants that act as natural enemies showing deviation from the preference-performance regimen in the evolutionary ecology of plant-insect interactions. The present study was designed to understand the role of glucosinolate-myrosinase system during P. xylostella interactions with a novel host. Adult moth preference and larval performance study were conducted on a novel host Lepidium latifolium L. (LL) that has high sinigrin content and was compared with its laboratory host Arabidopsis thaliana (AT). The glucosinolate-myrosinase system was studied in a time course experiment during larval feeding in choice and no-choice experiments. Adult moths visit and prefers LL over AT for oviposition. Conversely, LL leaves were not preferred and proved detrimental for P. xylostella larvae. Aliphatic and indolic glucosinolates were found to decrease significantly (p≤0.05) in AT during initial 12h of P. xylostella challenge, whereas, they were not affected in LL. Also, MYB transcription factor expression and myrosinase activity in LL do not suggest a typical host response to a specialist insect. This preference-performance mismatch of P. xylostella on LL mediated by glucosinolate pattern suggests that this novel plant could be utilized in P. xylostella management. PMID:27457978

  12. Quantitative proteomics reveals the importance of nitrogen source to control glucosinolate metabolism in Arabidopsis thaliana and Brassica oleracea.

    PubMed

    Marino, Daniel; Ariz, Idoia; Lasa, Berta; Santamaría, Enrique; Fernández-Irigoyen, Joaquín; González-Murua, Carmen; Aparicio Tejo, Pedro M

    2016-05-01

    Accessing different nitrogen (N) sources involves a profound adaptation of plant metabolism. In this study, a quantitative proteomic approach was used to further understand how the model plant Arabidopsis thaliana adjusts to different N sources when grown exclusively under nitrate or ammonium nutrition. Proteome data evidenced that glucosinolate metabolism was differentially regulated by the N source and that both TGG1 and TGG2 myrosinases were more abundant under ammonium nutrition, which is generally considered to be a stressful situation. Moreover, Arabidopsis plants displayed glucosinolate accumulation and induced myrosinase activity under ammonium nutrition. Interestingly, these results were also confirmed in the economically important crop broccoli (Brassica oleracea var. italica). Moreover, these metabolic changes were correlated in Arabidopsis with the differential expression of genes from the aliphatic glucosinolate metabolic pathway. This study underlines the importance of nitrogen nutrition and the potential of using ammonium as the N source in order to stimulate glucosinolate metabolism, which may have important applications not only in terms of reducing pesticide use, but also for increasing plants' nutritional value. PMID:27085186

  13. Quantitative proteomics reveals the importance of nitrogen source to control glucosinolate metabolism in Arabidopsis thaliana and Brassica oleracea

    PubMed Central

    Marino, Daniel; Ariz, Idoia; Lasa, Berta; Santamaría, Enrique; Fernández-Irigoyen, Joaquín; González-Murua, Carmen; Aparicio Tejo, Pedro M.

    2016-01-01

    Accessing different nitrogen (N) sources involves a profound adaptation of plant metabolism. In this study, a quantitative proteomic approach was used to further understand how the model plant Arabidopsis thaliana adjusts to different N sources when grown exclusively under nitrate or ammonium nutrition. Proteome data evidenced that glucosinolate metabolism was differentially regulated by the N source and that both TGG1 and TGG2 myrosinases were more abundant under ammonium nutrition, which is generally considered to be a stressful situation. Moreover, Arabidopsis plants displayed glucosinolate accumulation and induced myrosinase activity under ammonium nutrition. Interestingly, these results were also confirmed in the economically important crop broccoli (Brassica oleracea var. italica). Moreover, these metabolic changes were correlated in Arabidopsis with the differential expression of genes from the aliphatic glucosinolate metabolic pathway. This study underlines the importance of nitrogen nutrition and the potential of using ammonium as the N source in order to stimulate glucosinolate metabolism, which may have important applications not only in terms of reducing pesticide use, but also for increasing plants’ nutritional value. PMID:27085186

  14. Glucosinolate biochemical diversity and innovation in the Brassicales.

    PubMed

    Mithen, Richard; Bennett, Richard; Marquez, Julietta

    2010-12-01

    Glucosinolates were analysed from herbarium specimens and living tissues from representative of all families of the Brassicales, following the phylogenetic schemes of Rodman et al. (1998) and Hall et al. (2002, 2004), including specimens of Akania, Setchellanthus, Emblingia, Stixis, Forchhammeria and members of the Capparaceae for which glucosinolate content had not previously been reported. The results are reviewed along with additional published data on glucosinolate content of members of the Brassicales. In addition to providing an overview of the evolution of glucosinolate biochemical diversity within the core Brassicales, there were three main findings. Firstly, the glucosinolate content of some 'orphan' taxa of the Brassicales, such as Setchellanthus and Emblingia were consistent with recent phylogentic analyses based upon DNA sequence comparisons, while further analyses of Tirania and Stixis is required. Secondly, methyl glucosinolate is found within the Capparaceae and Cleomaceae, but also, unexpectedly, within Forchhammeria, with implications for the biochemical and evolutionary origin of methyl glucosinolate and the phylogenetic relationships of Forchhammeria. Thirdly, whereas Old World Capparaceae contain methyl glucosinolate, New World Capparaceae, including New World Capparis, either contain methyl glucosinolates or glucosinolates of complex and unresolved structures, indicative of continued innovation in glucosinolate biosynthesis. These taxa may be productive sources of glucosinolate biosynthetic genes and alleles that are not found in the model plant Arabidopsis thaliana. PMID:20971483

  15. Glucosinolate and Amino Acid Biosynthesis in Arabidopsis1

    PubMed Central

    Field, Ben; Cardon, Guillermo; Traka, Maria; Botterman, Johan; Vancanneyt, Guy; Mithen, Richard

    2004-01-01

    Enzymes that catalyze the condensation of acetyl coenzyme A and 2-oxo acids are likely to be important in two distinct metabolic pathways in Arabidopsis. These are the synthesis of isopropylmalate, an intermediate of Leu biosynthesis in primary metabolism, and the synthesis of methylthioalkylmalates, intermediates of Met elongation in the synthesis of aliphatic glucosinolates (GSLs), in secondary metabolism. Four Arabidopsis genes in the ecotype Columbia potentially encode proteins that could catalyze these reactions. MAM1 and MAML are adjacent genes on chromosome 5 at the Gsl-elong locus, while MAML-3 and MAML-4 are at opposite ends of chr 1. The isopropylmalate synthase activity of each member of the MAM-like gene family was investigated by heterologous expression in an isopropylmalate synthase-null Escherichia coli mutant. Only the expression of MAML-3 restored the ability of the mutant to grow in the absence of Leu. A MAML knockout line (KO) lacked long-chain aliphatic GSLs, which were restored when the KO was transformed with a functional MAML gene. Variation in expression of MAML did not alter the total levels of Met-derived GSLs, but just the ratio of chain lengths. MAML overexpression in Columbia led to an increase in long-chain GSLs, and an increase in 3C GSLs. Moreover, plants overexpressing MAML contained at least two novel amino acids. One of these was positively identified via MS/MS as homo-Leu, while the other, with identical mass and fragmentation patterns, was likely to be homo-Ile. A MAML-4 KO did not exhibit any changes in GSL profile, but had perturbed soluble amino acid content. PMID:15155874

  16. Altering glucosinolate profiles modulates disease resistance in plants.

    PubMed

    Brader, Günter; Mikkelsen, Michael Dalgaard; Halkier, Barbara Ann; Tapio Palva, E

    2006-06-01

    Plant diseases are major contributing factors for crop loss in agriculture. Here, we show that Arabidopsis plants with high levels of novel glucosinolates (GSs) as a result of the introduction of single CYP79 genes exhibit altered disease resistance. Arabidopsis expressing CYP79D2 from cassava accumulated aliphatic isopropyl and methylpropyl GS, and showed enhanced resistance against the bacterial soft-rot pathogen Erwinia carotovora, whereas Arabidopsis expressing the sorghum CYP79A1 or over-expressing the endogenous CYP79A2 accumulated p-hydroxybenzyl or benzyl GS, respectively, and showed increased resistance towards the bacterial pathogen Pseudomonas syringae. In addition to the direct toxic effects of GS breakdown products, increased accumulation of aromatic GSs was shown to stimulate salicylic acid-mediated defenses while suppressing jasmonate-dependent defenses, as manifested in enhanced susceptibility to the fungus Alternaria brassicicola. Arabidopsis with modified GS profiles provide important tools for evaluating the biological effects of individual GSs and thereby show potential as biotechnological tools for the generation of plants with tailor-made disease resistance. PMID:16709192

  17. Flower vs. Leaf Feeding by Pieris brassicae: Glucosinolate-Rich Flower Tissues are Preferred and Sustain Higher Growth Rate

    PubMed Central

    Smallegange, R. C.; Blatt, S. E.; Harvey, J. A.; Agerbirk, N.; Dicke, M.

    2007-01-01

    Interactions between butterflies and caterpillars in the genus Pieris and plants in the family Brassicaceae are among the best explored in the field of insect–plant biology. However, we report here for the first time that Pieris brassicae, commonly assumed to be a typical folivore, actually prefers to feed on flowers of three Brassica nigra genotypes rather than on their leaves. First- and second-instar caterpillars were observed to feed primarily on leaves, whereas late second and early third instars migrated via the small leaves of the flower branches to the flower buds and flowers. Once flower feeding began, no further leaf feeding was observed. We investigated growth rates of caterpillars having access exclusively to either leaves of flowering plants or flowers. In addition, we analyzed glucosinolate concentrations in leaves and flowers. Late-second- and early-third-instar P. brassicae caterpillars moved upward into the inflorescences of B. nigra and fed on buds and flowers until the end of the final (fifth) instar, after which they entered into the wandering stage, leaving the plant in search of a pupation site. Flower feeding sustained a significantly higher growth rate than leaf feeding. Flowers contained levels of glucosinolates up to five times higher than those of leaves. Five glucosinolates were identified: the aliphatic sinigrin, the aromatic phenyethylglucosinolate, and three indole glucosinolates: glucobrassicin, 4-methoxyglucobrassicin, and 4-hydroxyglucobrassicin. Tissue type and genotype were the most important factors affecting levels of identified glucosinolates. Sinigrin was by far the most abundant compound in all three genotypes. Sinigrin, 4-hydroxyglucobrassicin, and phenylethylglucosinolate were present at significantly higher levels in flowers than in leaves. In response to caterpillar feeding, sinigrin levels in both leaves and flowers were significantly higher than in undamaged plants, whereas 4-hydroxyglucobrassicin leaf levels were

  18. Root Glucosinolate Profiles for Screening of Radish (Raphanus sativus L.) Genetic Resources.

    PubMed

    Yi, Gibum; Lim, Sooyeon; Chae, Won Byoung; Park, Jeong Eun; Park, Hye Rang; Lee, Eun Jin; Huh, Jin Hoe

    2016-01-13

    Radish (Raphanus sativus L.), a root vegetable, is rich in glucosinolates (GLs), which are beneficial secondary metabolites for human health. To investigate the genetic variations in GL content in radish roots and the relationship with other root phenotypes, we analyzed 71 accessions from 23 different countries for GLs using HPLC. The most abundant GL in radish roots was glucoraphasatin, a GL with four-carbon aliphatic side chain. The content of glucoraphasatin represented at least 84.5% of the total GL content. Indolyl GL represented only 3.1% of the total GL at its maximum. The principal component analysis of GL profiles with various root phenotypes showed that four different genotypes exist in the 71 accessions. Although no strong correlation with GL content and root phenotype was observed, the varied GL content levels demonstrate the genetic diversity of GL content, and the amount that GLs could be potentially improved by breeding in radishes. PMID:26672790

  19. Ensiling carinata meal with forages to decrease glucosinolate concentrations

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Carinata meal (CM) has high quality protein, but it also has high glucosinolate concentrations which limits its use as a feedstuff. Our objective was to determine if ensiling CM with forages would decrease glucosinolates without compromising fermentation. Two trials were conducted, one on ensiling C...

  20. Bioavailability of Glucosinolates and Their Breakdown Products: Impact of Processing.

    PubMed

    Barba, Francisco J; Nikmaram, Nooshin; Roohinejad, Shahin; Khelfa, Anissa; Zhu, Zhenzhou; Koubaa, Mohamed

    2016-01-01

    Glucosinolates are a large group of plant secondary metabolites with nutritional effects, and are mainly found in cruciferous plants. After ingestion, glucosinolates could be partially absorbed in their intact form through the gastrointestinal mucosa. However, the largest fraction is metabolized in the gut lumen. When cruciferous are consumed without processing, myrosinase enzyme present in these plants hydrolyzes the glucosinolates in the proximal part of the gastrointestinal tract to various metabolites, such as isothiocyanates, nitriles, oxazolidine-2-thiones, and indole-3-carbinols. When cruciferous are cooked before consumption, myrosinase is inactivated and glucosinolates transit to the colon where they are hydrolyzed by the intestinal microbiota. Numerous factors, such as storage time, temperature, and atmosphere packaging, along with inactivation processes of myrosinase are influencing the bioavailability of glucosinolates and their breakdown products. This review paper summarizes the assimilation, absorption, and elimination of these molecules, as well as the impact of processing on their bioavailability. PMID:27579302

  1. Bioavailability of Glucosinolates and Their Breakdown Products: Impact of Processing

    PubMed Central

    Barba, Francisco J.; Nikmaram, Nooshin; Roohinejad, Shahin; Khelfa, Anissa; Zhu, Zhenzhou; Koubaa, Mohamed

    2016-01-01

    Glucosinolates are a large group of plant secondary metabolites with nutritional effects, and are mainly found in cruciferous plants. After ingestion, glucosinolates could be partially absorbed in their intact form through the gastrointestinal mucosa. However, the largest fraction is metabolized in the gut lumen. When cruciferous are consumed without processing, myrosinase enzyme present in these plants hydrolyzes the glucosinolates in the proximal part of the gastrointestinal tract to various metabolites, such as isothiocyanates, nitriles, oxazolidine-2-thiones, and indole-3-carbinols. When cruciferous are cooked before consumption, myrosinase is inactivated and glucosinolates transit to the colon where they are hydrolyzed by the intestinal microbiota. Numerous factors, such as storage time, temperature, and atmosphere packaging, along with inactivation processes of myrosinase are influencing the bioavailability of glucosinolates and their breakdown products. This review paper summarizes the assimilation, absorption, and elimination of these molecules, as well as the impact of processing on their bioavailability. PMID:27579302

  2. QTL Analysis for Four Major Genes Involved in the Aliphatic Glucosinolate Pathways of Brassica Oleracea

    Technology Transfer Automated Retrieval System (TEKTRAN)

    We screened by PCR a doubled haploid broccoli Early Big BAC library for genes CYP79F1, CS-Lyase, S-GT, and GS-OH using BAC pools. For that purpose, we used primers based on conserved regions of Arabidopsis thaliana orthologs. We designed the primers from the Brassica database to amplify the whole ...

  3. Glucosinolate Breakdown in Arabidopsis: Mechanism, Regulation and Biological Significance

    PubMed Central

    Wittstock, Ute; Burow, Meike

    2010-01-01

    Glucosinolates are a group of thioglucosides in plants of the Brassicales order. Together with their hydrolytic enzymes, the myrosinases, they constitute the ‘mustard oil bomb’ involved in plant defense. Here we summarize recent studies in Arabidopsis that have provided molecular evidence that the glucosinolate-myrosinase system is much more than a ‘two-component defense system,’ and started to unravel the roles of different glucosinolate breakdown pathways in the context of plant responses to biotic and abiotic stresses. PMID:22303260

  4. Synthesis and anti-inflammatory activity of aromatic glucosinolates.

    PubMed

    Vo, Quan V; Trenerry, Craige; Rochfort, Simone; Wadeson, Jenny; Leyton, Carolina; Hughes, Andrew B

    2013-10-01

    Aromatic GLs are important members of the glucosinolate family of compounds because of their potential biological activity and medicinal properties. This study has shown success in the high yielding synthesis of some important aromatic GLs as well as the results of testing for anti-inflammatory properties of the synthetic GLs. 3,4-Dimethoxyphenylglucosinolate was found to be the most active anti-inflammatory of the seven glucosinolates assayed. PMID:23978357

  5. Effect of Brassicaceae seed meals with different glucosinolate profiles on Rhizoctonia root rot of wheat

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Tissues of plants in the family Brassicaceae contain glucosinolates, compounds whose hydrolysis results in the release of various bioactive products including isothiocyanates. The broad spectrum of biological activity of these glucosinolate hydrolysis products has led to the promotion of brassicace...

  6. Development of a reliable extraction and quantification method for glucosinolates in Moringa oleifera.

    PubMed

    Förster, Nadja; Ulrichs, Christian; Schreiner, Monika; Müller, Carsten T; Mewis, Inga

    2015-01-01

    Glucosinolates are the characteristic secondary metabolites of plants in the order Brassicales. To date the common DIN extraction 'desulfo glucosinolates' method remains the common procedure for determination and quantification of glucosinolates. However, the desulfation step in the extraction of glucosinolates from Moringa oleifera leaves resulted in complete conversion and degradation of the naturally occurring glucosinolates in this plant. Therefore, a method for extraction of intact Moringa glucosinolates was developed and no conversion and degradation of the different rhamnopyranosyloxy-benzyl glucosinolates was found. Buffered eluents (0.1 M ammonium acetate) were necessary to stabilize 4-α-rhamnopyranosyloxy-benzyl glucosinolate (Rhamno-Benzyl-GS) and acetyl-4-α-rhamnopyranosyloxy-benzyl glucosinolate isomers (Ac-Isomers-GS) during HPLC analysis. Due to the instability of intact Moringa glucosinolates at room temperature and during the purification process of single glucosinolates, influences of different storage (room temperature, frozen, thawing and refreezing) and buffer conditions on glucosinolate conversion were analysed. Conversion and degradations processes were especially determined for the Ac-Isomers-GS III. PMID:25053080

  7. Glucosinolates redox activities: can they act as antioxidants?

    PubMed

    Natella, Fausta; Maldini, Mariateresa; Leoni, Guido; Scaccini, Cristina

    2014-04-15

    Glucosinolates are a class of secondary plant metabolites particularly occurring in Cruciferae with potential health-promoting properties, as their hydrolysis products, isothiocyanates, possess chemopreventive and antioxidant activities. In the present study, we systematically studied the in vitro redox behaviour of 15 glucosinolates, by using a range of analytical methods measuring different activities: (i) radical scavenging activity toward peroxyl and toward ABTS radical (chain-breaking activity); (ii) capacity in modulating the in vitro resistance of human low-density lipoprotein (LDL) catalysed by copper (chelating and chain-breaking activity). Data obtained from different assays were compared and analysed by principal component analysis (PCA). PCA allowed us to identify a big cluster of glucosinolates (10 out 15 tested) that do not possess any antioxidant capacity; while, the other five glucosinolates showed moderate and specific antioxidant capacity. Notably, sinalbin and gluconasturtiin were highly active in scavenging ABTS radical and in protecting LDL from copper-catalysed oxidation, respectively. The overall results of this study indicate that just few glucosinolates can act as antioxidants. PMID:24295700

  8. 40 CFR 721.3364 - Aliphatic ether.

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Aliphatic ether. 721.3364 Section 721... Aliphatic ether. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified generically as an aliphatic ether (PMN P-93-1381) is subject to reporting under...

  9. 40 CFR 721.3364 - Aliphatic ether.

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... 40 Protection of Environment 31 2011-07-01 2011-07-01 false Aliphatic ether. 721.3364 Section 721... Aliphatic ether. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified generically as an aliphatic ether (PMN P-93-1381) is subject to reporting under...

  10. Synthesis and anti-inflammatory activity of indole glucosinolates.

    PubMed

    Vo, Quan V; Trenerry, Craige; Rochfort, Simone; Wadeson, Jenny; Leyton, Carolina; Hughes, Andrew B

    2014-01-15

    The nitronate and nitrovinyl methods to synthesize indole glucosinolates (GLs) have been investigated. The results were applied to generally the most prevalent natural indole glucosinolates to synthesize 4-methoxyglucobrassicin (MGB) and neo-glucobrassicin (NGB) in moderate overall yield for the first time. The anti-inflammatory activity of the synthetic indole GLs was determined by inhibition of TNF-α secretion in LPS-stimulated THP-1 cells. The data showed that glucobrassicin (GB) exhibited higher activity than other synthetic indolyl GLs. PMID:24360830

  11. Camelina sativa defatted seed meal contains both alkyl sulfinyl glucosinolates and quercetin that synergize bioactivity.

    PubMed

    Das, Nilanjan; Berhow, Mark A; Angelino, Donato; Jeffery, Elizabeth H

    2014-08-20

    Camelina sativa L. Crantz is under development as a novel oilseed crop, yet bioefficacy of camelina phytochemicals is unknown. Defatted camelina seed meal contains two major aliphatic glucosinolates (GSLs), glucoarabin (9-(methylsulfinyl)nonylglucosinolate; GSL 9) and glucocamelinin (10-(methylsulfinyl)decylglucosinolate; GSL 10), with traces of a third, 11(methylsulfinyl)undecylglucosinolate and several flavonoids, mostly quercetin glycosides. In Hepa1c1c7 cells, hydrolyzed GSLs (hGSLs) 9 and 10 upregulated the phase II detoxification enzyme quinone reductase (NQO1), with no effect on cytochrome P450 (CYP) 1A1 activity. Isobologram graphs revealed synergy of NQO1 induction for a combination of hGSL 9 and quercetin. These findings suggest that defatted camelina seed meal should be evaluated for anticancer activity, similar to broccoli and other Brassicaceae family members. Interestingly, synergy of NQO1 induction was also seen for physiologically relevant doses of sulforaphane (SF) and quercetin, two key bioactives present in broccoli. This suggests that SF within broccoli may be more potent than purified SF. PMID:25050614

  12. Glucosinolate Biosynthesis (Further Characterization of the Aldoxime-Forming Microsomal Monooxygenases in Oilseed Rape Leaves).

    PubMed Central

    Bennett, R. N.; Hick, A. J.; Dawson, G. W.; Wallsgrove, R. M.

    1995-01-01

    The initial steps in glucosinolate biosynthesis are thought to proceed from amino acids, via N-hydroxy amino acids, to aldoximes. We showed previously that microsomes from green leaves of oilseed rape (Brassica napus cv Bienvenu) contain two distinct monooxygenases that catalyze the conversion of homophenylalanine and dihomomethionine to their respective aldoximes. Further characterization of these enzymes has now demonstrated that the latter enzyme catalyzes the NADPH-dependent oxidative decarboxylation of two higher homologs of methionine, in addition to dihomomethionine. No activity was found for either enzyme with L-methionine, DL-homomethionine, L-phenylalanine, L-tyrosine, or L-tryptophan. Both of these rape monooxygenase activities are dependent on O2, not requiring any other O2 species or radical. The presence of an unoxidized sulfur atom and its relative position in the side chain of the aliphatic substrates are important for binding to the active site of the methionine-homolog enzyme. Neither enzyme has any characteristics of a cytochrome P450-type enzyme, and antiserum raised against cytochrome P450 reductase did not significantly inhibit monooxygenase activity. PMID:12228596

  13. Comparison of Glucosinolate Profiles in Different Tissues of Nine Brassica Crops.

    PubMed

    Bhandari, Shiva Ram; Jo, Jung Su; Lee, Jun Gu

    2015-01-01

    Glucosinolate (GSL) profiles and concentrations in various tissues (seeds, sprouts, mature root, and shoot) were determined and compared across nine Brassica species, including cauliflower, cabbage, broccoli, radish, baemuchae, pakchoi, Chinese cabbage, leaf mustard, and kale. The compositions and concentrations of individual GSLs varied among crops, tissues, and growth stages. Seeds had highest total GSL concentrations in most of crops, whereas shoots had the lowest GSL concentrations. Aliphatic GSL concentrations were the highest in seeds, followed by that in sprouts, shoots, and roots. Indole GSL concentration was the highest in the root or shoot tissues in most of the crops. In contrast, aromatic GSL concentrations were highest in roots. Of the nine crops examined, broccoli exhibited the highest total GSL concentration in seeds (110.76 µmol·g(-1)) and sprouts (162.19 µmol·g(-1)), whereas leaf mustard exhibited the highest total GSL concentration in shoots (61.76 µmol·g(-1)) and roots (73.61 µmol·g(-1)). The lowest GSL concentrations were observed in radish across all tissues examined. PMID:26334264

  14. Glucosinolate metabolism, functionality and breeding for the improvement of Brassicaceae vegetables

    PubMed Central

    Ishida, Masahiko; Hara, Masakazu; Fukino, Nobuko; Kakizaki, Tomohiro; Morimitsu, Yasujiro

    2014-01-01

    Unique secondary metabolites, glucosinolates (S-glucopyranosyl thiohydroximates), are naturally occurring S-linked glucosides found mainly in Brassicaceae plants. They are enzymatically hydrolyzed to produce sulfate ions, D-glucose, and characteristic degradation products such as isothiocyanates. The functions of glucosinolates in the plants remain unclear, but isothiocyanates possessing a pungent or irritating taste and odor might be associated with plant defense from microbes. Isothiocyanates have been studied extensively in experimental in vitro and in vivo carcinogenesis models for their cancer chemopreventive properties. The beneficial isothiocyanates, glucosinolates that are functional for supporting human health, have received attention from many scientists studying plant breeding, plant physiology, plant genetics, and food functionality. This review presents a summary of recent topics related with glucosinolates in the Brassica family, along with a summary of the chemicals, metabolism, and genes of glucosinolates in Brassicaceae. The bioavailabilities of isothiocyanates from certain functional glucosinolates and the importance of breeding will be described with emphasis on glucosinolates. PMID:24987290

  15. Glucosinolate metabolism, functionality and breeding for the improvement of Brassicaceae vegetables.

    PubMed

    Ishida, Masahiko; Hara, Masakazu; Fukino, Nobuko; Kakizaki, Tomohiro; Morimitsu, Yasujiro

    2014-05-01

    Unique secondary metabolites, glucosinolates (S-glucopyranosyl thiohydroximates), are naturally occurring S-linked glucosides found mainly in Brassicaceae plants. They are enzymatically hydrolyzed to produce sulfate ions, D-glucose, and characteristic degradation products such as isothiocyanates. The functions of glucosinolates in the plants remain unclear, but isothiocyanates possessing a pungent or irritating taste and odor might be associated with plant defense from microbes. Isothiocyanates have been studied extensively in experimental in vitro and in vivo carcinogenesis models for their cancer chemopreventive properties. The beneficial isothiocyanates, glucosinolates that are functional for supporting human health, have received attention from many scientists studying plant breeding, plant physiology, plant genetics, and food functionality. This review presents a summary of recent topics related with glucosinolates in the Brassica family, along with a summary of the chemicals, metabolism, and genes of glucosinolates in Brassicaceae. The bioavailabilities of isothiocyanates from certain functional glucosinolates and the importance of breeding will be described with emphasis on glucosinolates. PMID:24987290

  16. Guided desaturation of unactivated aliphatics

    NASA Astrophysics Data System (ADS)

    Voica, Ana-Florina; Mendoza, Abraham; Gutekunst, Will R.; Fraga, Jorge Otero; Baran, Phil S.

    2012-08-01

    The excision of hydrogen from an aliphatic carbon chain to produce an isolated olefin (desaturation) without overoxidation is one of the most impressive and powerful biosynthetic transformations for which there are no simple and mild laboratory substitutes. The versatility of olefins and the range of reactions they undergo are unsurpassed in functional group space. Thus, the conversion of a relatively inert aliphatic system into its unsaturated counterpart could open new possibilities in retrosynthesis. In this article, the invention of a directing group to achieve such a transformation under mild, operationally simple, metal-free conditions is outlined. This ‘portable desaturase’ (TzoCl) is a bench-stable, commercial entity (Aldrich, catalogue number L510092) that is facile to install on alcohol and amine functionalities to ultimately effect remote desaturation, while leaving behind a synthetically useful tosyl group.

  17. Aliphatic hydrocarbons of the fungi.

    NASA Technical Reports Server (NTRS)

    Weete, J. D.

    1972-01-01

    Review of studies of aliphatic hydrocarbons which have been recently detected in the spores of phytopathogenic fungi, and are found to be structurally very similar to the alkanes of higher plants. It appears that the hydrocarbon components of the few mycelial and yeast forms reported resemble the distribution found in bacteria. The occurence and distribution of these compounds in the fungi is discussed. Suggested functional roles of fungal spore alkanes are presented.

  18. Functional analysis of three BrMYB28 transcription factors controlling the biosynthesis of glucosinolates in Brassica rapa.

    PubMed

    Seo, Mi-Suk; Jin, Mina; Chun, Jin-Hyuk; Kim, Sun-Ju; Park, Beom-Seok; Shon, Seong-Han; Kim, Jung Sun

    2016-03-01

    Glucosinolates (GSLs) are secondary metabolites that have anticarcinogenic activity and play defense roles in plants of the Brassicaceae family. MYB28 is known as a transcription factor that regulates aliphatic GSL biosynthesis in Arabidopsis thaliana. Brassicaceae plants have three orthologous copies of AtMYB28 derived from recent genome triplication. These BrMYB28 genes have a high level of sequence homology, with 81-87% similarities in the coding DNA sequence compared to Arabidopsis. Overexpression of three paralogous BrMYB28 genes in transgenic Chinese cabbage increased the total GSL content in all T1 generation plants and in two inbred lines of homozygous T2 plants. The highest total GSL contents were detected in homozygous T2 lines overexpressing BrMYB28.1, which showed an approximate fivefold increase compared to that of nontransgenic plants. The homozygous T2 lines with overexpressed BrMYB28.1 also showed an increased content of aliphatic, indolic, and aromatic GSLs compared to that of nontransgenic plants. Furthermore, all of the three BrMYB28 genes were identified as negative regulators of BrAOP2 and positive regulators of BrGSL-OH in the homozygous T2 lines. These data indicate the regulatory mechanism of GSL biosynthesis in B. rapa is unlike that in A. thaliana. Our results will provide useful information for elucidating the regulatory mechanism of GSL biosynthesis in polyploid plants. PMID:26820138

  19. Combinatorics of aliphatic amino acids.

    PubMed

    Grützmann, Konrad; Böcker, Sebastian; Schuster, Stefan

    2011-01-01

    This study combines biology and mathematics, showing that a relatively simple question from molecular biology can lead to complicated mathematics. The question is how to calculate the number of theoretically possible aliphatic amino acids as a function of the number of carbon atoms in the side chain. The presented calculation is based on earlier results from theoretical chemistry concerning alkyl compounds. Mathematical properties of this number series are highlighted. We discuss which of the theoretically possible structures really occur in living organisms, such as leucine and isoleucine with a chain length of four. This is done both for a strict definition of aliphatic amino acids only involving carbon and hydrogen atoms in their side chain and for a less strict definition allowing sulphur, nitrogen and oxygen atoms. While the main focus is on proteinogenic amino acids, we also give several examples of non-proteinogenic aliphatic amino acids, playing a role, for instance, in signalling. The results are in agreement with a general phenomenon found in biology: Usually, only a small number of molecules are chosen as building blocks to assemble an inconceivable number of different macromolecules as proteins. Thus, natural biological complexity arises from the multifarious combination of building blocks. PMID:21120449

  20. Stability of glucosinolates and glucosinolate degradation products during storage of boiled white cabbage.

    PubMed

    Ciska, Ewa; Drabińska, Natalia; Narwojsz, Agnieszka; Honke, Joanna

    2016-07-15

    The aim of the study was to investigate the effect of storage on the contents of glucosinolates (GLS) and their degradation products in a boiled white cabbage. A 24h storage at 4 °C resulted in a decrease in GLS content (20-40%, depending on the cooking time applied) in the edible parts. The most significant losses were observed for sinigrin (20-45%), and the least for glucobrassicin (12-32%). Storage had a diversified effect on GLS breakdown products (indole-3-acetonitrile, indole-3-carbinol, ascorbigen and 3,3'-diindolylmethane released from glucobrassicin and 4-methylsulfinylbutanenitrile released from glucoiberin) in the boiled cabbage. The increase in the content of indole-3-acetonitrile, especially considerable within the first 24h of storage (and a simultaneous decrease in glucobrassicin) clearly indicates that degradation of GLS may occur during storage or cooling to 4 °C. PMID:26948623

  1. Analysis of Phenolics and Glucosinolates in Broccoli Seeds and Sprouts

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Plants from the crucifer family (Brassicaceae) have been touted for their health-enhancing effects when incorporated into diets of both humans and animals. Recently, a great deal of research attention has been focused on the glucosinolates, due to their high positive activity of their hydrolysis pr...

  2. Characterisation of aphid myrosinase and degradation studies of glucosinolates.

    PubMed

    Francis, Frédéric; Lognay, Georges; Wathelet, Jean-Paul; Haubruge, Eric

    2002-08-01

    Myrosinase from Brevicoryne brassicae was purified by ammonium sulfate fractionation, dialysis, and chromatography on a DEAE column. The chromatography yielded a single peak and a 115.6-fold purification. Further FPLC gel filtration gave a single peak at 120 kDa. Denaturing SDS/PAGE of the protein revealed a single band at 60 kDa, indicating that the native B. brassicae myrosinase is a dimer. Kinetic parameters towards 8 glucosinolates were calculated. Strong differences of V(max) and K(m) were observed depending on the substrate. Degradation products of each glucosinolate were identified and quantified by GC-MS and GLC-FID, respectively. Using both crude aphid homogenates and purified myrosinase, two unique hydroxyglucosinolates, 3-butenyl- and benzyl-isothiocyanates were identified from progoitrin ((2S)-2-hydroxybut-3-enyl-glucosinolate) and sinalbin (4-hydroxybenzyl-glucosinolate) degradation respectively. Addition of ascorbic acid to the reaction mixtures containing sinalbin and progoitrin caused the production of hydroxylated degradation products usually associated with plant myrosinase metabolisation. The occurrence of the myrosinase system in B. brassicae is discussed in terms of similar allelochemical adaptation between the herbivore and its host plant. PMID:12125058

  3. 'Moringa oleifera: study of phenolics and glucosinolates by mass spectrometry'.

    PubMed

    Maldini, Mariateresa; Maksoud, Salwa A; Natella, Fausta; Montoro, Paola; Petretto, Giacomo Luigi; Foddai, Marzia; De Nicola, Gina Rosalinda; Chessa, Mario; Pintore, Giorgio

    2014-09-01

    Moringa oleifera is a medicinal plant and an excellent dietary source of micronutrients (vitamins and minerals) and health-promoting phytochemicals (phenolic compounds, glucosinolates and isothiocyanates). Glucosinolates and isothiocyanates are known to possess anti-carcinogenic and antioxidant effects and have attracted great interest from both toxicological and pharmacological points of view, as they are able to induce phase 2 detoxification enzymes and to inhibit phase 1 activation enzymes. Phenolic compounds possess antioxidant properties and may exert a preventative effect in regards to the development of chronic degenerative diseases. The aim of this work was to assess the profile and the level of bioactive compounds in all parts of M. oleifera seedlings, by using different MS approaches. First, flow injection electrospray ionization mass spectrometry (FI-ESI-MS) fingerprinting techniques and chemometrics (PCA) were used to achieve the characterization of the different plant's organs in terms of profile of phenolic compounds and glucosinolates. Second, LC-MS and LC-MS/MS qualitative and quantitative methods were used for the identification and/or determination of phenolics and glucosinolates in M. oleifera. PMID:25230187

  4. Uptake and turn-over of glucosinolates sequestered in the sawfly Athalia rosae.

    PubMed

    Müller, Caroline; Wittstock, Ute

    2005-10-01

    Larvae of the sawfly Athalia rosae sequester glucosinolates from their various host plants of the Brassicaceae into their hemolymph for defensive purposes. We found that the glucosinolate concentration in the insect varies in a fluctuating manner during larval development. Analyses of larvae which had been offered diets with different glucosinolate profiles showed that there is an equilibrium between a rapid uptake of glucosinolates into the hemolymph and a continuous turn-over. Injection of glucotropaeolin into the hemolymph and ingestion of the same amount resulted in similar levels of intact glucosinolates recovered from larvae after different periods of time. This indicates that hemolymph glucosinolates are the principal source for glucosinolate degradation. Feeding experiments with [14C]-labeled glucotropaeolin revealed that the majority of the ingested glucosinolate is excreted as one or more unidentified metabolite(s) within 14 h. We found no indication for the presence of an insect myrosinase, or sulfatase in A. rosae, which have been shown to be involved in glucosinolate metabolism in other specialists feeding on Brassicaceae. Furthermore, the metabolism of sinalbin in A. rosae seems to result in different products than its metabolism in the caterpillar Pieris rapae. Obviously, A. rosae has yet another way of coping with the glucosinolates. PMID:16102424

  5. Glucosinolates and derived products in cruciferous vegetables: total glucosinolates by retention on anion exchange resin and enzymatic hydrolysis to measure released glucose.

    PubMed

    VanEtten, C H; Daxenbichler, M E

    1977-07-01

    Details are given for determining total glucosinolates in Cruciferae plants by a procedure measuring released glucose. The glucosinolates are separated from about 90% of other material in the plant extract by adsorption on an anion exchange resin. Then, by a selective thioglucosidase hydrolysis of the glucosinolates retained on the exchange resin, the glucose and aglucons are separated from other substances retained by the resin. Glucose is released into an aqueous medium and is equivalent to the total glucosinolates. The aglucons formed by the hydrolysis are extracted into methylene chloride and determined by gas-liquid chromatography. Based on 29 determinations of the glucose from sinigrin, analyzed under different conditions, accuracy of the total glucosinolate determination was 94.8 +/- 7.3%. The coefficient of variation, determined by duplicate analyses on extracts from 58 cabbage samples, was 4.6%. PMID:893313

  6. Determination of glucosinolates in 19 Chinese medicinal plants with spectrophotometry and high-pressure liquid chromatography.

    PubMed

    Hu, Ye; Liang, Hao; Yuan, Qipeng; Hong, Yuancheng

    2010-08-01

    Glucosinolates were evaluated in 19 traditional Chinese medicinal plants involved in seven different families: Brassicaceae, Capparaceae, Euphorbiaceae, Phytolaccaceae, Tropaeolaceae, Caricaceae and Rubiaceae. The total glucosinolate contents were determined by spectrophotometry. Results showed that the high contents of total glucosinolates were found in some herbs of Brassicaceae, Capparaceae and Euphorbiaceae families, while low total glucosinolate contents were observed in two Rubiaceae herbs. In addition, eight glucosinolates (glucoraphanin, glucoraphenin, sinalbin, sinigrin, progoitrin, 4-hydroglucobrassicin, glucoiberin and glucoibervirin) in these herbs were measured using HPLC, and the data showed that individual glucosinolates and their contents varied at different degrees among the distinct species. The highest contents of cancer-protective compounds were found in the seeds of Raphanus sativus L. (glucoraphenin), Sinapis alba (sinalbin) and Phyllanthus emblica L. (sinigrin). PMID:20645206

  7. The desert locust, Schistocerca gregaria, detoxifies the glucosinolates of Schouwia purpurea by desulfation.

    PubMed

    Falk, Kimberly L; Gershenzon, Jonathan

    2007-08-01

    Desert locusts (Schistocerca gregaria) occasionally feed on Schouwia purpurea, a plant that contains tenfold higher levels of glucosinolates than most other Brassicaceae. Whereas this unusually high level of glucosinolates is expected to be toxic and/or deterrent to most insects, locusts feed on the plant with no apparent ill effects. In this paper, we demonstrate that the desert locust, like larvae of the diamondback moth (Plutella xylostella), possesses a glucosinolate sulfatase in the gut that hydrolyzes glucosinolates to their corresponding desulfonated forms. These are no longer susceptible to cleavage by myrosinase, thus eliminating the formation of toxic glucosinolate hydrolysis products. Sulfatase is found throughout the desert locust gut and can catalyze the hydrolysis of all of the glucosinolates present in S. purpurea. The enzyme was detected in all larval stages of locusts as well as in both male and female adults feeding on this plant species. Glucosinolate sulfatase activity is induced tenfold when locusts are fed S. purpurea after being maintained on a glucosinolate-free diet, and activity declines when glucosinolates are removed from the locust diet. A detoxification system that is sensitive to the dietary levels of a plant toxin may minimize the physiological costs of toxin processing, especially for a generalist insect herbivore that encounters large variations in plant defense metabolites while feeding on different species. PMID:17619221

  8. Verticillium Suppression Is Associated with the Glucosinolate Composition of Arabidopsis thaliana Leaves

    PubMed Central

    Witzel, Katja; Hanschen, Franziska S.; Schreiner, Monika; Krumbein, Angelika; Ruppel, Silke; Grosch, Rita

    2013-01-01

    The soil-borne fungal pathogen Verticillium longisporum is able to penetrate the root of a number of plant species and spread systemically via the xylem. Fumigation of Verticillium contaminated soil with Brassica green manure is used as an environmentally friendly method for crop protection. Here we present a study focused on the potential role of glucosinolates and their breakdown products of the model plant Arabidopsis thaliana in suppressing growth of V. longisporum. For this purpose we analysed the glucosinolate composition of the leaves and roots of a set of 19 key accessions of A. thaliana. The effect of volatile glucosinolate hydrolysis products on the in vitro growth of the pathogen was tested by exposing the fungus to hydrated lyophilized plant tissue. Volatiles released from leaf tissue were more effective than from root tissue in suppressing mycelial growth of V. longisporum. The accessions varied in their efficacy, with the most effective suppressing mycelial growth by 90%. An analysis of glucosinolate profiles and their enzymatic degradation products revealed a correlation between fungal growth inhibition and the concentration of alkenyl glucosinolates, particularly 2-propenyl (2Prop) glucosinolate, respectively its hydrolysis products. Exposure of the fungus to purified 2Prop glucosinolate revealed that its suppressive activity was correlated with its concentration. Spiking of 2Prop glucosinolate to leaf material of one of the least effective A. thaliana accessions led to fungal growth suppression. It is suggested that much of the inhibitory effect observed for the tested accessions can be explained by the accumulation of 2Prop glucosinolate. PMID:24039726

  9. Isolation and identification of 4-α-rhamnosyloxy benzyl glucosinolate in Noccaea caerulescens showing intraspecific variation.

    PubMed

    de Graaf, Rob M; Krosse, Sebastian; Swolfs, Ad E M; te Brinke, Esra; Prill, Nadine; Leimu, Roosa; van Galen, Peter M; Wang, Yanli; Aarts, Mark G M; van Dam, Nicole M

    2015-02-01

    Glucosinolates are secondary plant compounds typically found in members of the Brassicaceae and a few other plant families. Usually each plant species contains a specific subset of the ∼ 130 different glucosinolates identified to date. However, intraspecific variation in glucosinolate profiles is commonly found. Sinalbin (4-hydroxybenzyl glucosinolate) so far has been identified as the main glucosinolate of the heavy metal accumulating plant species Noccaea caerulescens (Brassicaceae). However, a screening of 13 N. caerulescens populations revealed that in 10 populations a structurally related glucosinolate was found as the major component. Based on nuclear magnetic resonance (NMR) and mass spectrometry analyses of the intact glucosinolate as well as of the products formed after enzymatic conversion by sulfatase or myrosinase, this compound was identified as 4-α-rhamnosyloxy benzyl glucosinolate (glucomoringin). So far, glucomoringin had only been reported as the main glucosinolate of Moringa spp. (Moringaceae) which are tropical tree species. There was no apparent relation between the level of soil pollution at the location of origin, and the presence of glucomoringin. The isothiocyanate that is formed after conversion of glucomoringin is a potent antimicrobial and antitumor agent. It has yet to be established whether glucomoringin or its breakdown product have an added benefit to the plant in its natural habitat. PMID:25482220

  10. Effect of light conditions on the contents of glucosinolates in germinating seeds of white mustard, red radish, white radish, and rapeseed.

    PubMed

    Ciska, Ewa; Honke, Joanna; Kozłowska, Halina

    2008-10-01

    The study was aimed at determining the effect of light conditions on contents of glucosinolates (GLS) in germinating seeds of white mustard, red radish, white radish, and rapeseed. The seeds were germinated in light and dark, at 25 degrees C, for up to 7 days. As compared to the nongerminated seeds, in seeds exposed to light and germinated for 4, 5, 6, and 7 days the content of total GLS was observed to decrease by 30 to 70% depending on the species. Germination in conducted the dark for the respective periods of time resulted in decreases of total GLS not exceeding 25%. The changes in the concentration of total GLS were attributed to aliphatic GLS predominating in seeds, yet in the case of white mustard to sinalbin belonging to aralkyl glucosinolates. Although seeds germinated in the dark, as compared to those exposed to light, were characterized by a higher total content of indole GLS, the percentage contribution of that group of compounds in white mustard, red radish, and white radish remained at a similar level, irrespective of germination time. Only in the case of rapeseed was the percentage of the sum of indole GLS observed to increase from 17 to up to 45% once the seeds were exposed to light and to 50% once they were germinated in the dark. PMID:18771273

  11. A mode of action of glucosinolate-derived isothiocyanates: Detoxification depletes glutathione and cysteine levels with ramifications on protein metabolism in Spodoptera littoralis.

    PubMed

    Jeschke, Verena; Gershenzon, Jonathan; Vassão, Daniel Giddings

    2016-04-01

    Glucosinolates are activated plant defenses common in the order Brassicales that release isothiocyanates (ITCs) and other hydrolysis products upon tissue damage. The reactive ITCs are toxic to insects resulting in reduced growth, delayed development and occasionally mortality. Generalist lepidopteran larvae often detoxify ingested ITCs via conjugation to glutathione (GSH) and survive on low glucosinolate diets, but it is not known how this process influences other aspects of metabolism. We investigated the impact of the aliphatic 4-methylsulfinylbutyl-ITC (4msob-ITC, sulforaphane) on the metabolism of Spodoptera littoralis larvae, which suffer a significant growth decline on 4msob-ITC-containing diets while excreting ITC-glutathione conjugates and their derivatives in the frass. The most striking effects were a decrease of GSH in midgut tissue and hemolymph due to losses by conjugation to ITC during detoxification, and a decline of the GSH biosynthetic precursor cysteine. Protein content was likewise reduced by ITC treatment suggesting that protein is actively catabolized in an attempt to supply cysteine for GSH biosynthesis. The negative growth and protein effects were relieved by dietary supplementation with cystine. Other consequences of protein breakdown included deamination of amino acids with increased excretion of uric acid and elevated lipid content. Thus metabolic detoxification of ITCs provokes a cascade of negative effects on insects that result in reduced fitness. PMID:26855197

  12. Dielectric relaxations in aliphatic polyesters

    NASA Astrophysics Data System (ADS)

    Sen, Sudeepto

    2001-07-01

    The dielectric technique was used to study the relaxation processes of five linear aliphatic polyesters. The polyesters studied were poly (ethylene succinate/adipate) or PESA, poly (trimethylene succinate/adipate) or PTSA, poly (butylene succinate/adipate) or PBSA, poly (ethylene succinate) or PES, and poly (ethylene adipate) or PEA. Three of the polyesters were copolymers (PESA, PTSA, and PBSA), and the remaining two (PES and PEA) were homopolymers. Two of the five were amorphous (PESA and PTSA), and the remaining three (PBSA, PES, and PEA) were semicrystalline. All the five polyesters were synthesized in the laboratory using a poly-condensation reaction between a series of aliphatic diols and diesters. The succinic and adipic groups in the copolymers are in equimolar amounts. The polymers were characterized by differential scanning calorimetry and density measurements. Elemental analysis done on the polymers confirmed that their compositions matched theoretical estimates. The relaxation processes were studied dielectrically using an IMASS time domain dielectric spectrometer (TDS) and an HP 4284A LCR meter. Together they allowed a frequency range from 0.001 Hz to 1 MHz. Typically in the subglass region, good data were obtained between 0.01 Hz and 100 kHz. In the glass transition region, good data were occasionally available over the entire range. Two relaxation processes were detected in the subglass temperature region for all the polymers, and in the case of the copolymers PTSA and PBSA, they were also well resolved. Both the processes showed Arrhenius behavior with modest activation energies characteristic of subglass processes in general. They also progressively merged with increasing temperature, which implies a lower activation energy for the faster process which is consistent with the current understanding of relaxation phenomena. The glass transition region of all the polymers also showed a merging of the dominant alpha relaxation with the subglass

  13. De novo Transcriptome Analysis of Sinapis alba in Revealing the Glucosinolate and Phytochelatin Pathways

    PubMed Central

    Zhang, Xiaohui; Liu, Tongjin; Duan, Mengmeng; Song, Jiangping; Li, Xixiang

    2016-01-01

    Sinapis alba is an important condiment crop and can also be used as a phytoremediation plant. Though it has important economic and agronomic values, sequence data, and the genetic tools are still rare in this plant. In the present study, a de novo transcriptome based on the transcriptions of leaves, stems, and roots was assembled for S. alba for the first time. The transcriptome contains 47,972 unigenes with a mean length of 1185 nt and an N50 of 1672 nt. Among these unigenes, 46,535 (97%) unigenes were annotated by at least one of the following databases: NCBI non-redundant (Nr), Swiss-Prot, Kyoto Encyclopedia of Genes and Genomes (KEGG) pathway, Gene Ontology (GO), and Clusters of Orthologous Groups of proteins (COGs). The tissue expression pattern profiles revealed that 3489, 1361, and 8482 unigenes were predominantly expressed in the leaves, stems, and roots of S. alba, respectively. Genes predominantly expressed in the leaf were enriched in photosynthesis- and carbon fixation-related pathways. Genes predominantly expressed in the stem were enriched in not only pathways related to sugar, ether lipid, and amino acid metabolisms but also plant hormone signal transduction and circadian rhythm pathways, while the root-dominant genes were enriched in pathways related to lignin and cellulose syntheses, involved in plant-pathogen interactions, and potentially responsible for heavy metal chelating, and detoxification. Based on this transcriptome, 14,727 simple sequence repeats (SSRs) were identified, and 12,830 pairs of primers were developed for 2522 SSR-containing unigenes. Additionally, the glucosinolate (GSL) and phytochelatin metabolic pathways, which give the characteristic flavor and the heavy metal tolerance of this plant, were intensively analyzed. The genes of aliphatic GSLs pathway were predominantly expressed in roots. The absence of aliphatic GSLs in leaf tissues was due to the shutdown of BCAT4, MAM1, and CYP79F1 expressions. Glutathione was extensively

  14. De novo Transcriptome Analysis of Sinapis alba in Revealing the Glucosinolate and Phytochelatin Pathways.

    PubMed

    Zhang, Xiaohui; Liu, Tongjin; Duan, Mengmeng; Song, Jiangping; Li, Xixiang

    2016-01-01

    Sinapis alba is an important condiment crop and can also be used as a phytoremediation plant. Though it has important economic and agronomic values, sequence data, and the genetic tools are still rare in this plant. In the present study, a de novo transcriptome based on the transcriptions of leaves, stems, and roots was assembled for S. alba for the first time. The transcriptome contains 47,972 unigenes with a mean length of 1185 nt and an N50 of 1672 nt. Among these unigenes, 46,535 (97%) unigenes were annotated by at least one of the following databases: NCBI non-redundant (Nr), Swiss-Prot, Kyoto Encyclopedia of Genes and Genomes (KEGG) pathway, Gene Ontology (GO), and Clusters of Orthologous Groups of proteins (COGs). The tissue expression pattern profiles revealed that 3489, 1361, and 8482 unigenes were predominantly expressed in the leaves, stems, and roots of S. alba, respectively. Genes predominantly expressed in the leaf were enriched in photosynthesis- and carbon fixation-related pathways. Genes predominantly expressed in the stem were enriched in not only pathways related to sugar, ether lipid, and amino acid metabolisms but also plant hormone signal transduction and circadian rhythm pathways, while the root-dominant genes were enriched in pathways related to lignin and cellulose syntheses, involved in plant-pathogen interactions, and potentially responsible for heavy metal chelating, and detoxification. Based on this transcriptome, 14,727 simple sequence repeats (SSRs) were identified, and 12,830 pairs of primers were developed for 2522 SSR-containing unigenes. Additionally, the glucosinolate (GSL) and phytochelatin metabolic pathways, which give the characteristic flavor and the heavy metal tolerance of this plant, were intensively analyzed. The genes of aliphatic GSLs pathway were predominantly expressed in roots. The absence of aliphatic GSLs in leaf tissues was due to the shutdown of BCAT4, MAM1, and CYP79F1 expressions. Glutathione was extensively

  15. The Mark 5C VLBI Data System

    NASA Technical Reports Server (NTRS)

    Whitney, Alan; Ruszczyk, Chester; Romney, Jon; Owens, Ken

    2010-01-01

    The Mark 5C disk-based VLBI data system is being developed as the third-generation Mark 5 disk-based system, increasing the sustained data-recording rate capability to 4 Gbps. It is built on the same basic platform as the Mark 5A, Mark 5B and Mark 5B+ systems and will use the same 8-disk modules as earlier Mark 5 systems, although two 8-disk modules will be necessary to support the 4 Gbps rate. Unlike its earlier brethren, which use proprietary data interfaces, the Mark 5C will accept data from a standard 10 Gigabit Ethernet connection and be compatible with the emerging VLBI Data Interchange Format (VDIF) standard. Data sources for the Mark 5C system will be based on new digital backends now being developed, specifically the RDBE in the U.S. and the dBBC in Europe, as well as others. The Mark 5C system is being planned for use with the VLBI2010 system and will also be used by NRAO as part of the VLBA sensitivity upgrade program; it will also be available to the global VLBI community from Conduant. Mark 5C system specification and development is supported by Haystack Observatory, NRAO, and Conduant Corporation. Prototype Mark 5C systems are expected in early 2010.

  16. The Mark 5C VLBI Data System

    NASA Astrophysics Data System (ADS)

    Whitney, Alan; Ruszczyk, Chet; Romney, Jon; Owens, Kenneth

    2010-12-01

    The Mark 5C disk-based VLBI data system is being developed as the third-generation Mark 5 disk-based system, increasing the sustained data-recording rate capability to 4 Gbps. It is built on the same basic platform as the Mark 5A, Mark 5B and Mark 5B+ systems and will use the same 8-disk modules as earlier Mark 5 systems, although two 8-disk modules will be necessary to support the 4 Gbps rate. Unlike its earlier brethren, which use proprietary data interfaces, the Mark 5C will accept data from a standard 10 Gigabit Ethernet connection and be compatible with the emerging VLBI Data Interchange Format (VDIF) standard. Data sources for the Mark 5C system will be based on new digital backends now being developed, specifically the RDBE in the U.S. and the dBBC in Europe, as well as others. The Mark 5C system is being planned for use with the VLBI2010 system and will also be used by NRAO as part of the VLBA sensitivity upgrade program; it will also be available to the global VLBI community from Conduant. Mark 5C system specification and development is supported by Haystack Observatory, NRAO, and Conduant Corporation. Prototype Mark 5C systems are expected in early 2010.

  17. Glucosinolate and Desulfo-glucosinolate Metabolism by a Selection of Human Gut Bacteria.

    PubMed

    Luang-In, Vijitra; Albaser, Abdulhadi Ali; Nueno-Palop, Carmen; Bennett, Mark H; Narbad, Arjan; Rossiter, John T

    2016-09-01

    Glucosinolate (GSL) hydrolysis is mediated by the enzyme myrosinase which together with specifier proteins can give rise to isothiocyanates (ITCs), thiocyanates, and nitriles (NITs) in cruciferous plants. However, little is known about the metabolism of GSLs by the human gut flora. The aim of the work was to investigate the metabolic fates of sinigrin (SNG), glucotropaeolin (GTP), gluconasturtiin (GNT), and their corresponding desulfo-GSLs (DS-GSLs). Three human gut bacterial strains, Enterococcus casseliflavus CP1, Lactobacillus agilis R16, and Escherichia coli VL8, were chosen for this study. GNT was metabolized to completion within 24 h to phenethyl ITC and phenethyl NIT (PNIT) by all bacteria, except for L. agilis R16 which produced only PNIT. At least 80 % of GTP and SNG were metabolized by all bacteria within 24 h to the corresponding ITCs and NITs. The pH of media over time gradually became acidic for both L. agilis R16 and E. coli VL8, while for E. casseliflavus CP1 the media became slightly alkaline with NIT and ITC production occurring between pH 3.0 and 7.5. ITC production peaked between 4 and 10 h in most cases and gradually declined while NIT production increased and remained relatively constant over time. The total percentage products accounted for 3-53 % of the initial GSL. NITs were produced from DS-GSLs suggesting an alternative metabolism via desulfation for the food based GSLs. The metal ion dependency for NIT production for GNT and its DS form was investigated where it was shown that Fe(2+) increased NIT production, while Mg(2+) stimulated the formation of ITC. PMID:27301252

  18. A mechanistic perspective on process-induced changes in glucosinolate content in Brassica vegetables: a review.

    PubMed

    Nugrahedi, Probo Y; Verkerk, Ruud; Widianarko, Budi; Dekker, Matthijs

    2015-01-01

    Brassica vegetables are consumed mostly after processing, which is expected to give beneficial effects on the vegetable properties, such as improved palatability and bioavailability of nutrients, or shelf life extension. But processing also results to various changes in the content of health promoting phytochemicals like glucosinolates. This paper reviews the effects of processing on the glucosinolates content by using a mechanism approach underlying processing method employed. Cultural differences between Eastern and Western preparation practices and their possible effect on glucosinolate retention are highlighted. Boiling and blanching considerably reduce the glucosinolate content mainly due to mechanisms of cell lysis, diffusion, and leaching, and partly due to thermal and enzymatic degradation. Steaming, microwave processing, and stir frying either retain or slightly reduce the glucosinolates content due to low degrees of leaching; moreover, these methods seem to enhance extractability of glucosinolates from the plant tissue. Fermentation reduces the glucosinolate content considerably, but the underlying mechanisms are not yet studied in detail. Studying the changes of glucosinolates during processing by a mechanistic approach is shown to be valuable to understand the impact of processing and to optimize processing conditions for health benefits of these compounds. PMID:24915330

  19. Glucosinolate variation among six cultigens of broccoli grown in five diverse east coast locations

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Broccoli (Brassica oleracea var. italica) consumption has increased in the United States, driven at least partially by recognition that it is highly nutritious and contains high concentrations of glucosinolates (GS). Glucosinolates are secondary metabolites in broccoli that when digested have a det...

  20. Garlic Mustard (Alliaria petiolata) Glucosinolate Content Varies Across a Natural Light Gradient.

    PubMed

    Smith, Lauren M

    2015-05-01

    Garlic mustard is a well-known invader of deciduous forests of North America, yet the influence of environmental factors on garlic mustard allelochemical production is not well understood. Three experiments were conducted to detect interactions between one garlic mustard allelochemical (glucosinolate) production and light availability. First, to detect patterns of glucosinolate production across a natural light gradient, leaves and roots of mature plants and first-year rosettes were sampled in patches ranging from 100 to 2 % of full sun within an Indiana forest. Second, to determine whether genetic variation drives observed correlations between glucosinolate content and light, seed collected across light gradients within six sites was grown in a common garden and glucosinolate production was measured. Finally, to understand whether local adaptation occurred in garlic mustard's response to light, seed collected from defined light environments across six sites was grown under four light treatments. Results of the field sampling showed that mature plants' root glucosinolate content was elevated in high compared to low light. In the common garden experiment, however, there was no correlation between light availability at seed origin and constitutive glucosinolate content. Additionally, in the common light treatments, there was no evidence for local adaptation to light environment. Overall, the results indicate that plasticity in response to light, not genetic variation among plants growing in different light environments, generates correlations between glucosinolate content and light in the field. Since mature garlic mustard populations in high light may exhibit increased glucosinolate content, it makes them potential targets for management. PMID:25912227

  1. Lactic acid bacteria convert glucosinolates to nitriles efficiently yet differently from enterobacteriaceae.

    PubMed

    Mullaney, Jane A; Kelly, William J; McGhie, Tony K; Ansell, Juliet; Heyes, Julian A

    2013-03-27

    Glucosinolates from the genus Brassica can be converted into bioactive compounds known to induce phase II enzymes, which may decrease the risk of cancers. Conversion via hydrolysis is usually by the brassica enzyme myrosinase, which can be inactivated by cooking or storage. We examined the potential of three beneficial bacteria, Lactobacillus plantarum KW30, Lactococcus lactis subsp. lactis KF147, and Escherichia coli Nissle 1917, and known myrosinase-producer Enterobacter cloacae to catalyze the conversion of glucosinolates in broccoli extract. Enterobacteriaceae consumed on average 65% glucoiberin and 78% glucoraphanin, transforming them into glucoiberverin and glucoerucin, respectively, and small amounts of iberverin nitrile and erucin nitrile. The lactic acid bacteria did not accumulate reduced glucosinolates, consuming all at 30-33% and transforming these into iberverin nitrile, erucin nitrile, sulforaphane nitrile, and further unidentified metabolites. Adding beneficial bacteria to a glucosinolate-rich diet may increase glucosinolate transformation, thereby increasing host exposure to bioactives. PMID:23461529

  2. Diversity of Kale (Brassica oleracea var. sabellica): Glucosinolate Content and Phylogenetic Relationships.

    PubMed

    Hahn, Christoph; Müller, Anja; Kuhnert, Nikolai; Albach, Dirk

    2016-04-27

    Recently, kale has become popular due to nutritive components beneficial for human health. It is an important source of phytochemicals such as glucosinolates that trigger associated cancer-preventive activity. However, nutritional value varies among glucosinolates and among cultivars. Here, we start a systematic determination of the content of five glucosinolates in 25 kale varieties and 11 non-kale Brassica oleracea cultivars by HPLC-DAD-ESI-MS(n) and compare the profiles with results from the analysis of SNPs derived from a KASP genotyping assay. Our results demonstrate that the glucosinolate levels differ markedly among varieties of different origin. Comparison of the phytochemical data with phylogenetic relationships revealed that the common name kale refers to at least three different groups. German, American, and Italian kales differ morphologically and phytochemically. Landraces do not show outstanding glucosinolate levels. Our results demonstrate the diversity of kale and the importance of preserving a broad genepool for future breeding purposes. PMID:27028789

  3. Overexpression of Three Glucosinolate Biosynthesis Genes in Brassica napus Identifies Enhanced Resistance to Sclerotinia sclerotiorum and Botrytis cinerea.

    PubMed

    Zhang, Yuanyuan; Huai, Dongxin; Yang, Qingyong; Cheng, Yan; Ma, Ming; Kliebenstein, Daniel J; Zhou, Yongming

    2015-01-01

    Sclerotinia sclerotiorum and Botrytis cinerea are notorious plant pathogenic fungi with an extensive host range including Brassica crops. Glucosinolates (GSLs) are an important group of secondary metabolites characteristic of the Brassicales order, whose degradation products are proving to be increasingly important in plant protection. Enhancing the defense effect of GSL and their associated degradation products is an attractive strategy to strengthen the resistance of plants by transgenic approaches. We generated the lines of Brassica napus with three biosynthesis genes involved in GSL metabolic pathway (BnMAM1, BnCYP83A1 and BnUGT74B1), respectively. We then measured the foliar GSLs of each transgenic lines and inoculated them with S. sclerotiorum and B. cinerea. Compared with the wild type control, over-expressing BnUGT74B1 in B. napus increased the aliphatic and indolic GSL levels by 1.7 and 1.5 folds in leaves respectively; while over-expressing BnMAM1 or BnCYP83A1 resulted in an approximate 1.5-fold higher only in the aliphatic GSL level in leaves. The results of plant inoculation demonstrated that BnUGT74B1-overexpressing lines showed less severe disease symptoms and tissue damage compared with the wild type control, but BnMAM1 or BnCYP83A1-overexpressing lines showed no significant difference in comparison to the controls. These results suggest that the resistance to S. sclerotiorum and B. cinerea in B. napus could be enhanced through tailoring the GSL profiles by transgenic approaches or molecular breeding, which provides useful information to assist plant breeders to design improved breeding strategies. PMID:26465156

  4. Overexpression of Three Glucosinolate Biosynthesis Genes in Brassica napus Identifies Enhanced Resistance to Sclerotinia sclerotiorum and Botrytis cinerea

    PubMed Central

    Yang, Qingyong; Cheng, Yan; Ma, Ming; Kliebenstein, Daniel J.; Zhou, Yongming

    2015-01-01

    Sclerotinia sclerotiorum and Botrytis cinerea are notorious plant pathogenic fungi with an extensive host range including Brassica crops. Glucosinolates (GSLs) are an important group of secondary metabolites characteristic of the Brassicales order, whose degradation products are proving to be increasingly important in plant protection. Enhancing the defense effect of GSL and their associated degradation products is an attractive strategy to strengthen the resistance of plants by transgenic approaches. We generated the lines of Brassica napus with three biosynthesis genes involved in GSL metabolic pathway (BnMAM1, BnCYP83A1 and BnUGT74B1), respectively. We then measured the foliar GSLs of each transgenic lines and inoculated them with S. sclerotiorum and B. cinerea. Compared with the wild type control, over-expressing BnUGT74B1 in B. napus increased the aliphatic and indolic GSL levels by 1.7 and 1.5 folds in leaves respectively; while over-expressing BnMAM1 or BnCYP83A1 resulted in an approximate 1.5-fold higher only in the aliphatic GSL level in leaves. The results of plant inoculation demonstrated that BnUGT74B1-overexpressing lines showed less severe disease symptoms and tissue damage compared with the wild type control, but BnMAM1 or BnCYP83A1-overexpressing lines showed no significant difference in comparison to the controls. These results suggest that the resistance to S. sclerotiorum and B. cinerea in B. napus could be enhanced through tailoring the GSL profiles by transgenic approaches or molecular breeding, which provides useful information to assist plant breeders to design improved breeding strategies. PMID:26465156

  5. Oxygenases for aliphatic hydrocarbons and fatty acids

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Oxygenases catalyzing the insertion of oxygen into either aliphatic hydrocarbons or fatty acids have great similarity. There are two classes of oxygenases: monooxygenases and dioxygenases. Dioxygenase inserts both atoms of molecular oxygen into a substrate, whereas monooxygenase incorporates one a...

  6. Anaerobic digestion of aliphatic polyesters.

    PubMed

    Šmejkalová, Pavla; Kužníková, Veronika; Merna, Jan; Hermanová, Soňa

    2016-01-01

    Anaerobic processes for the treatment of plastic materials waste represent versatile and effective approach in environmental protection and solid waste management. In this work, anaerobic biodegradability of model aliphatic polyesters, poly(L-lactic acid) (PLA), and poly(ɛ-caprolactone) (PCL), in the form of powder and melt-pressed films with varying molar mass, was studied. Biogas production was explored in batch laboratory trials at 55 ± 1°C under a nitrogen atmosphere. The inoculum used was thermophilic digested sludge (total solids concentration of 2.9%) from operating digesters at the Central Waste Water Treatment Plant in Prague, Czech Republic. Methanogenic biodegradation of PCLs typically yielded from 54 to 60% of the theoretical biogas yield. The biodegradability of PLAs achieved from 56 to 84% of the theoretical value. High biogas yield (up to 677 mL/g TS) with high methane content (more than 60%), comparable with conventionally processed materials, confirmed the potential of polyester samples for anaerobic treatment in the case of their exploitation in agriculture or as a packaging material in the food industry. PMID:27191559

  7. Glucosinolate profiles change during the life cycle and mycorrhizal colonization in a Cd/Zn hyperaccumulator Thlaspi praecox (Brassicaceae).

    PubMed

    Pongrac, Paula; Vogel-Mikus, Katarina; Regvar, Marjana; Tolrà, Roser; Poschenrieder, Charlotte; Barceló, Juan

    2008-08-01

    Thlaspi praecox Wulfen (Brassicaceae) is a perennial Cd/Zn hyperaccumulating plant species that forms functional arbuscular mycorrhizal (AM) symbiosis. Glucosinolates (GS) were studied in different organs of field-collected T. praecox at differing plant developmental stages. Additionally, AM colonization was recorded. Total GS concentrations and profiles of nine individual GS varied during the plant life cycle. Novel individual GS that were related to specific developmental phases, mainly to flowering and seed production, were identified. The highest total GS and sinalbin concentrations in rosette leaves were found in the vegetative phase, possibly contributing to protection of young, palatable leaves. The lowest were found in roots during the flowering and the seeding phases. Increased total GS concentrations in roots and enhanced aliphatic GS, especially glucobrassicanapin, in the senescence phase may protect roots from herbivory during winter and early spring. The presence of glucotropaeolin and the absence of glucobrassicanapin in the flowering phase coincided with peak AM colonization. This is the first report on GS profiles in an AM and metal-hyperaccumulating plant. PMID:18584257

  8. Metabolic engineering of valine- and isoleucine-derived glucosinolates in Arabidopsis expressing CYP79D2 from Cassava.

    PubMed

    Mikkelsen, Michael Dalgaard; Halkier, Barbara Ann

    2003-02-01

    Glucosinolates are amino acid-derived natural products that, upon hydrolysis, typically release isothiocyanates with a wide range of biological activities. Glucosinolates play a role in plant defense as attractants and deterrents against herbivores and pathogens. A key step in glucosinolate biosynthesis is the conversion of amino acids to the corresponding aldoximes, which is catalyzed by cytochromes P450 belonging to the CYP79 family. Expression of CYP79D2 from cassava (Manihot esculenta Crantz.) in Arabidopsis resulted in the production of valine (Val)- and isoleucine-derived glucosinolates not normally found in this ecotype. The transgenic lines showed no morphological phenotype, and the level of endogenous glucosinolates was not affected. The novel glucosinolates were shown to constitute up to 35% of the total glucosinolate content in mature rosette leaves and up to 48% in old leaves. Furthermore, at increased concentrations of these glucosinolates, the proportion of Val-derived glucosinolates decreased. As the isothiocyanates produced from the Val- and isoleucine-derived glucosinolates are volatile, metabolically engineered plants producing these glucosinolates have acquired novel properties with great potential for improvement of resistance to herbivorous insects and for biofumigation. PMID:12586901

  9. Profiling of Glucosinolates and Flavonoids in Rorippa indica (Linn.) Hiern. (Cruciferae) by UHPLC-PDA-ESI/HRMSn

    PubMed Central

    2015-01-01

    An UHPLC-PDA-ESI/HRMSn profiling method was used to identify the glucosinolates and flavonoids of Rorippa indica (Cruciferae), a wild vegetable and Chinese herb used to treat cough, diarrhea, and rheumatoid arthritis. Thirty-three glucosinolates, more than 40 flavonol glycosides, and 18 other phenolic and common organic compounds were identified. The glucosinolates and polyphenols were separated by UHPLC. High-resolution deprotonated molecules provided high accuracy mass values that were used to determine formulas and provide putative identification of the glucosinolates and flavonoids. The fragments from multistage mass spectrometry were used to elucidate the structures. The concentrations of the main components were based on UV peak areas and molar relative response factors with a single calibration standard. This study found this plant to be a rich source for glucosinolates, containing 24 new glucosinolates, including 14 glucosylated glucosinolates that were previously unidentified. PMID:24893216

  10. Variable glucosinolate profiles of Cardamine pratensis (Brassicaceae) with equal chromosome numbers.

    PubMed

    Agerbirk, Niels; Olsen, Carl Erik; Chew, Frances S; Ørgaard, Marian

    2010-04-28

    A novel glucosinolate, 3-(hydroxymethyl)pentylglucosinolate, was present at high levels in Cardamine pratensis L. from eastern North America and in commercially obtained seeds, but not in C. pratensis plants from southern Scandinavia. Glucosinolates in a number of accessions of C. pratensis included glucosinolates with the side chains 1-methylethyl, 1-(hydroxymethyl)ethyl, 1-methylpropyl, 1-(hydroxymethyl)propyl, 3-methylpentyl, 3-(hydroxymethyl)pentyl, benzyl, 4-hydroxybenzyl, 4-methoxybenzyl, indol-3-ylmethyl (as well as its 1-methoxy, 4-hydroxy, and 4-methoxy derivatives) and the rare side chain 1,4-dimethoxyindol-3-ylmethyl. Substantial variation was observed for four biosynthetic characters: (i) extent of chain elongation of Ile-derived glucosinolates; (ii) biosynthesis of Phe/Tyr-derived glucosinolates in general; (iii) hydroxylation of branched-chain glucosinolates; and (iv) O-methylation of 4-hydroxybenzylglucosinolate (sinalbin). Cytological analysis of pollen mother cells and root tip cells in meiosis and mitosis established the chromosome number to be 2n = 30 for all accessions, irrespective of glucosinolate profile. PMID:20334382

  11. MCNPX version 2.5.c

    SciTech Connect

    Hendricks, J. S.

    2003-01-01

    MCNPX is a Fortran 90 Monte Carlo radiation transport computer code that transports all particles at all energies. It is a superset of MCNP4C3, and has many capabilities beyond MCNP4C3. These capabilities are summarized along with their quality guarantee and code availability. Then the user interface changes from MCNP are described. Finally, the n.ew capabilities of the latest version, MCNPX 2.5.c, are documented. Future plans and references are also provided.

  12. Sequestration of host plant glucosinolates in the defensive hemolymph of the sawfly Athalia rosae.

    PubMed

    Müller, C; Agerbirk, N; Olsen, C E; Boevé, J L; Schaffner, U; Brakefield, P M

    2001-12-01

    Interactions between insects and glucosinolate-containing plant species have been investigated for a long time. Although the glucosinolate-myrosinase system is believed to act as a defense mechanism against generalist herbivores and fungi, several specialist insects use these secondary metabolites for host plant finding and acceptance and can handle them physiologically. However, sequestration of glucosinolates in specialist herbivores has been less well studied. Larvae of the tumip sawfly Athalia rosae feed on several glucosinolate-containing plant species. When larvae are disturbed by antagonists, they release one or more small droplets of hemolymph from their integument. This "reflex bleeding" is used as a defense mechanism. Specific glucosinolate analysis, by conversion to desulfoglucosinolates and analysis of these by high-performance liquid chromatography coupled to diode array UV spectroscopy and mass spectrometry, revealed that larvae incorporate and concentrate the plant's characteristic glucosinolates from their hosts. Extracts of larvae that were reared on Sinapis alba contained sinalbin, even when the larvae were first starved for 22 hr and, thus, had empty guts. Hemolymph was analyzed from larvae that were reared on either S. alba, Brassica nigra, or Barbarea stricta. Leaves were analyzed from the same plants the larvae had fed on. Sinalbin (from S. alba), sinigrin (B. nigra), or glucobarbarin and glucobrassicin (B. stricta) were present in leaves in concentrations less than 1 micromol/g fresh weight, while the same glucosinolates could be detected in the larvae's hemolymph in concentrations between 10 and 31 micromol/g fresh weight, except that glucobrassicin was present only as a trace. In larval feces, only trace amounts of glucosinolates (sinalbin and sinigrin) could be detected. The glucosinolates were likewise found in freshly emerged adults, showing that the sequestered phytochemicals were transferred through the pupal stage. PMID:11789955

  13. The bifurcation of the cyanogenic glucoside and glucosinolate biosynthetic pathways.

    PubMed

    Clausen, Mette; Kannangara, Rubini M; Olsen, Carl E; Blomstedt, Cecilia K; Gleadow, Roslyn M; Jørgensen, Kirsten; Bak, Søren; Motawie, Mohammed S; Møller, Birger Lindberg

    2015-11-01

    The biosynthetic pathway for the cyanogenic glucoside dhurrin in sorghum has previously been shown to involve the sequential production of (E)- and (Z)-p-hydroxyphenylacetaldoxime. In this study we used microsomes prepared from wild-type and mutant sorghum or transiently transformed Nicotiana benthamiana to demonstrate that CYP79A1 catalyzes conversion of tyrosine to (E)-p-hydroxyphenylacetaldoxime whereas CYP71E1 catalyzes conversion of (E)-p-hydroxyphenylacetaldoxime into the corresponding geometrical Z-isomer as required for its dehydration into a nitrile, the next intermediate in cyanogenic glucoside synthesis. Glucosinolate biosynthesis is also initiated by the action of a CYP79 family enzyme, but the next enzyme involved belongs to the CYP83 family. We demonstrate that CYP83B1 from Arabidopsis thaliana cannot convert the (E)-p-hydroxyphenylacetaldoxime to the (Z)-isomer, which blocks the route towards cyanogenic glucoside synthesis. Instead CYP83B1 catalyzes the conversion of the (E)-p-hydroxyphenylacetaldoxime into an S-alkyl-thiohydroximate with retention of the configuration of the E-oxime intermediate in the final glucosinolate core structure. Numerous microbial plant pathogens are able to detoxify Z-oximes but not E-oximes. The CYP79-derived E-oximes may play an important role in plant defense. PMID:26361733

  14. Indole Glucosinolate Biosynthesis Limits Phenylpropanoid Accumulation in Arabidopsis thaliana

    PubMed Central

    2015-01-01

    Plants produce an array of metabolites (including lignin monomers and soluble UV-protective metabolites) from phenylalanine through the phenylpropanoid biosynthetic pathway. A subset of plants, including many related to Arabidopsis thaliana, synthesizes glucosinolates, nitrogen- and sulfur-containing secondary metabolites that serve as components of a plant defense system that deters herbivores and pathogens. Here, we report that the Arabidopsis thaliana reduced epidermal fluorescence5 (ref5-1) mutant, identified in a screen for plants with defects in soluble phenylpropanoid accumulation, has a missense mutation in CYP83B1 and displays defects in glucosinolate biosynthesis and in phenylpropanoid accumulation. CYP79B2 and CYP79B3 are responsible for the production of the CYP83B1 substrate indole-3-acetaldoxime (IAOx), and we found that the phenylpropanoid content of cyp79b2 cyp79b3 and ref5-1 cyp79b2 cyp79b3 plants is increased compared with the wild type. These data suggest that levels of IAOx or a subsequent metabolite negatively influence phenylpropanoid accumulation in ref5 and more importantly that this crosstalk is relevant in the wild type. Additional biochemical and genetic evidence indicates that this inhibition impacts the early steps of the phenylpropanoid biosynthetic pathway and restoration of phenylpropanoid accumulation in a ref5-1 med5a/b triple mutant suggests that the function of the Mediator complex is required for the crosstalk. PMID:25944103

  15. Aromatic Glucosinolate Biosynthesis Pathway in Barbarea vulgaris and its Response to Plutella xylostella Infestation

    PubMed Central

    Liu, Tongjin; Zhang, Xiaohui; Yang, Haohui; Agerbirk, Niels; Qiu, Yang; Wang, Haiping; Shen, Di; Song, Jiangping; Li, Xixiang

    2016-01-01

    The inducibility of the glucosinolate resistance mechanism is an energy-saving strategy for plants, but whether induction would still be triggered by glucosinolate-tolerant Plutella xylostella (diamondback moth, DBM) after a plant had evolved a new resistance mechanism (e.g., saponins in Barbara vulgaris) was unknown. In B. vulgaris, aromatic glucosinolates derived from homo-phenylalanine are the dominant glucosinolates, but their biosynthesis pathway was unclear. In this study, we used G-type (pest-resistant) and P-type (pest-susceptible) B. vulgaris to compare glucosinolate levels and the expression profiles of their biosynthesis genes before and after infestation by DBM larvae. Two different stereoisomers of hydroxylated aromatic glucosinolates are dominant in G- and P-type B. vulgaris, respectively, and are induced by DBM. The transcripts of genes in the glucosinolate biosynthesis pathway and their corresponding transcription factors were identified from an Illumina dataset of G- and P-type B. vulgaris. Many genes involved or potentially involved in glucosinolate biosynthesis were induced in both plant types. The expression patterns of six DBM induced genes were validated by quantitative PCR (qPCR), while six long-fragment genes were validated by molecular cloning. The core structure biosynthetic genes showed high sequence similarities between the two genotypes. In contrast, the sequence identity of two apparent side chain modification genes, the SHO gene in the G-type and the RHO in P-type plants, showed only 77.50% identity in coding DNA sequences and 65.48% identity in deduced amino acid sequences. The homology to GS-OH in Arabidopsis, DBM induction of the transcript and a series of qPCR and glucosinolate analyses of G-type, P-type and F1 plants indicated that these genes control the production of S and R isomers of 2-hydroxy-2-phenylethyl glucosinolate. These glucosinolates were significantly induced by P. xylostella larvae in both the susceptiple P

  16. Aromatic Glucosinolate Biosynthesis Pathway in Barbarea vulgaris and its Response to Plutella xylostella Infestation.

    PubMed

    Liu, Tongjin; Zhang, Xiaohui; Yang, Haohui; Agerbirk, Niels; Qiu, Yang; Wang, Haiping; Shen, Di; Song, Jiangping; Li, Xixiang

    2016-01-01

    The inducibility of the glucosinolate resistance mechanism is an energy-saving strategy for plants, but whether induction would still be triggered by glucosinolate-tolerant Plutella xylostella (diamondback moth, DBM) after a plant had evolved a new resistance mechanism (e.g., saponins in Barbara vulgaris) was unknown. In B. vulgaris, aromatic glucosinolates derived from homo-phenylalanine are the dominant glucosinolates, but their biosynthesis pathway was unclear. In this study, we used G-type (pest-resistant) and P-type (pest-susceptible) B. vulgaris to compare glucosinolate levels and the expression profiles of their biosynthesis genes before and after infestation by DBM larvae. Two different stereoisomers of hydroxylated aromatic glucosinolates are dominant in G- and P-type B. vulgaris, respectively, and are induced by DBM. The transcripts of genes in the glucosinolate biosynthesis pathway and their corresponding transcription factors were identified from an Illumina dataset of G- and P-type B. vulgaris. Many genes involved or potentially involved in glucosinolate biosynthesis were induced in both plant types. The expression patterns of six DBM induced genes were validated by quantitative PCR (qPCR), while six long-fragment genes were validated by molecular cloning. The core structure biosynthetic genes showed high sequence similarities between the two genotypes. In contrast, the sequence identity of two apparent side chain modification genes, the SHO gene in the G-type and the RHO in P-type plants, showed only 77.50% identity in coding DNA sequences and 65.48% identity in deduced amino acid sequences. The homology to GS-OH in Arabidopsis, DBM induction of the transcript and a series of qPCR and glucosinolate analyses of G-type, P-type and F1 plants indicated that these genes control the production of S and R isomers of 2-hydroxy-2-phenylethyl glucosinolate. These glucosinolates were significantly induced by P. xylostella larvae in both the susceptiple P

  17. Aliphatic polyamines in physiology and diseases.

    PubMed

    Ramani, D; De Bandt, J P; Cynober, L

    2014-02-01

    Aliphatic polyamines are a family of polycationic molecules derived from decarboxylation of the amino acid ornithine that classically comprise three molecules: putrescine, spermidine and spermine. In-cell polyamine homeostasis is tightly controlled at key steps of cell metabolism. Polyamines are involved in an array of cellular functions from DNA stabilization, and regulation of gene expression to ion channel function and, particularly, cell proliferation. As such, aliphatic polyamines play an essential role in rapidly dividing cells such as in the immune system and digestive tract. Because of their role in cell proliferation, polyamines are also involved in carcinogenesis, prompting intensive research into polyamine metabolism as a target in cancer therapy. More recently, another aliphatic polyamine, agmatine, the decarboxylated derivative of arginine, has been identified as a neurotransmitter in mammals, and investigations have focused on its effects in the CNS, notably as a neuroprotector in brain injury. PMID:24144912

  18. Aliphatic amines in the Murchison meteorite

    NASA Technical Reports Server (NTRS)

    Jungclaus, G.; Cronin, J. R.; Moore, C. B.; Yuen, G. U.

    1976-01-01

    The paper reports on the determination of aliphatic amines in water extracts of the Murchison meteorite. The amines were analyzed by gas chromatography both as the free amines and as 2,4-dinitrophenyl (DNP) derivatives. The results give evidence for the presence of all of the possible primary aliphatic monoamines (eight) with fewer than five carbon atoms. Two of the seven possible secondary or tertiary aliphatic monoamines were identified. The identified primary amines total 80 nmol per g meteorite, and seem to be chemically or physically trapped in the meteorite. Similarities between the water-extractable amines and amino acids suggest that (1) a simple carbon compound, methane, for example, is the precursor of meteorite amines and amino acids, and (2) both amines and amino acids are extracted from the meteorite both as such and in the form of acid-hydrolyzable derivative or precursor species.

  19. Effect of CO2 enrichment on the glucosinolate contents under different nitrogen levels in bolting stem of Chinese kale (Brassica alboglabra L.).

    PubMed

    La, Gui-xiao; Fang, Ping; Teng, Yi-bo; Li, Ya-juan; Lin, Xian-yong

    2009-06-01

    The effects of CO(2) enrichment on the growth and glucosinolate (GS) concentrations in the bolting stem of Chinese kale (Brassica alboglabra L.) treated with three nitrogen (N) concentrations (5, 10, and 20 mmol/L) were investigated. Height, stem thickness, and dry weights of the total aerial parts, bolting stems, and roots, as well as the root to shoot ratio, significantly increased as CO(2) concentration was elevated from 350 to 800 microl/L at each N concentration. In the edible part of the bolting stem, 11 individual GSs were identified, including 7 aliphatic and 4 indolyl GSs. GS concentration was affected by the elevated CO(2) concentration, N concentration, and CO(2)xN interaction. At 5 and 10 mmol N/L, the concentrations of aliphatic GSs and total GSs significantly increased, whereas those of indolyl GSs were not affected, by elevated atmospheric CO(2). However, at 20 mmol N/L, elevated CO(2) had no significant effects on the concentrations of total GSs and total indolyl GSs, but the concentrations of total aliphatic GSs significantly increased. Moreover, the bolting stem carbon (C) content increased, whereas the N and sulfur (S) contents decreased under elevated CO(2) concentration in the three N treatments, resulting in changes in the C/N and N/S ratios. Also the C/N ratio is not a reliable predictor of change of GS concentration, while the changes in N and S contents and the N/S ratio at the elevated CO(2) concentration may influence the GS concentration in Chinese kale bolting stems. The results demonstrate that high nitrogen supply is beneficial for the growth of Chinese kale, but not for the GS concentration in bolting stems, under elevated CO(2) condition. PMID:19489111

  20. Microbial degradation of aliphatic and aliphatic-aromatic co-polyesters.

    PubMed

    Shah, Aamer Ali; Kato, Satoshi; Shintani, Noboru; Kamini, Numbi Ramudu; Nakajima-Kambe, Toshiaki

    2014-04-01

    Biodegradable plastics (BPs) have attracted much attention since more than a decade because they can easily be degraded by microorganisms in the environment. The development of aliphatic-aromatic co-polyesters has combined excellent mechanical properties with biodegradability and an ideal replacement for the conventional nondegradable thermoplastics. The microorganisms degrading these polyesters are widely distributed in various environments. Although various aliphatic, aromatic, and aliphatic-aromatic co-polyester-degrading microorganisms and their enzymes have been studied and characterized, there are still many groups of microorganisms and enzymes with varying properties awaiting various applications. In this review, we have reported some new microorganisms and their enzymes which could degrade various aliphatic, aromatic, as well as aliphatic-aromatic co-polyesters like poly(butylene succinate) (PBS), poly(butylene succinate)-co-(butylene adipate) (PBSA), poly(ε-caprolactone) (PCL), poly(ethylene succinate) (PES), poly(L-lactic acid) (PLA), poly(3-hydroxybutyrate) and poly(3-hydoxybutyrate-co-3-hydroxyvalterate) (PHB/PHBV), poly(ethylene terephthalate) (PET), poly(butylene terephthalate) (PBT), poly(butylene adipate-co-terephthalate (PBAT), poly(butylene succinate-co-terephthalate) (PBST), and poly(butylene succinate/terephthalate/isophthalate)-co-(lactate) (PBSTIL). The mechanism of degradation of aliphatic as well as aliphatic-aromatic co-polyesters has also been discussed. The degradation ability of microorganisms against various polyesters might be useful for the treatment and recycling of biodegradable wastes or bioremediation of the polyester-contaminated environments. PMID:24522729

  1. Optimized analysis and quantification of glucosinolates from Camelina sativa seeds by reverse-phase liquid chromatography

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Gold-of-pleasure or false flax (Camelina sativa L. Crantz) presscake contains three relatively unique glucosinolates: glucoarabin (9-(methylsulfinyl) nonylglucosinolate)glucocamelinin (10-(methylsulfinyl)decylglucosinolate), and 11-(methylsulfinyl)undecylglucosinolate. Using defatted seed material...

  2. Glucosinolate Metabolites Required for an Arabidopsis Innate Immune Response*

    PubMed Central

    Clay, Nicole K.; Adio, Adewale M.; Denoux, Carine; Jander, Georg; Ausubel, Frederick M.

    2008-01-01

    Summary The perception of pathogen or microbe-associated molecular pattern molecules by plants triggers a basal defense response analogous to animal innate immunity, and is defined in part by the deposition of the glucan polymer callose at the cell wall at the site of pathogen contact. Transcriptional and metabolic profiling in Arabidopsis mutants, coupled with the monitoring of pathogen triggered callose deposition, have identified major roles in pathogen response for the plant hormone ethylene and the secondary metabolite 4-methoxy-indol-3-ylmethylglucosinolate. Two genes, PEN2 and PEN3, are also necessary for resistance to pathogens and are required for both callose deposition and glucosinolate activation, suggesting that the pathogen triggered callose response is required for resistance to microbial pathogens. Our study shows that well-studied plant metabolites, previously identified as important in avoiding damage by herbivores, are also required as a component of the plant defense response against microbial pathogens. PMID:19095898

  3. [Microbiological degradation of glucosinolates in defatted rapeseed meal].

    PubMed

    Huber, J; Kranz, G; Kreibich, G; Beining, K; Krüger, M; Weissbach, F

    1983-01-01

    During the degradation of thioglucosides in defatted rape seed meal (RES) microorganisms were found, whose ability to degrade glucosinolates (GSL) and vinyl thio-oxazolidone (VTO) was not known so far. The isolated microorganisms are two strains of bacteria of the species Bacillus cereus and the yeast Trichosporon cutaneum. The degradation of GSL and VTO in the cultural broths by the Bacillus cereus strains was the more complete the more other Gram-negative bacteria from RES were additionally present. Drinking tests with Wistar rats showed that here is a relation between the watersoluble and mainly bitter toxin substances of rape and their influence on the increase of the animals body weight. PMID:6684210

  4. HPLC-Based Method to Evaluate Kinetics of Glucosinolate Hydrolysis by Sinapis alba Myrosinase1

    PubMed Central

    Vastenhout, Kayla J.; Tornberg, Ruthellen H.; Johnson, Amanda L.; Amolins, Michael W.; Mays, Jared R.

    2014-01-01

    Isothiocyanates (ITCs) are one of several hydrolysis products of glucosinolates, plant secondary metabolites which are substrates for the thioglucohydrolase myrosinase. Recent pursuits toward the development of synthetic, non-natural ITCs have consequently led to an exploration of generating these compounds from non-natural glucosinolate precursors. Evaluation of the myrosinase-dependent conversion of select non-natural glucosinolates to non-natural ITCs cannot be accomplished using established UV-Vis spectroscopic methods. To overcome this limitation, an alternative HPLC-based analytical approach was developed where initial reaction velocities were generated from non-linear reaction progress curves. Validation of this HPLC method was accomplished through parallel evaluation of three glucosinolates with UV-Vis methodology. The results of this study demonstrate that kinetic data is consistent between both analytical methods and that the tested glucosinolates respond similarly to both Michaelis–Menten and specific activity analyses. Consequently, this work resulted in the complete kinetic characterization of three glucosinolates with Sinapis alba myrosinase, with results that were consistent with previous reports. PMID:25068719

  5. Cultivation conditions and selenium fertilization alter the phenolic profile, glucosinolate, and sulforaphane content of broccoli.

    PubMed

    Robbins, Rebecca J; Keck, Anna-Sigrid; Banuelos, Gary; Finley, John W

    2005-01-01

    Broccoli is a food often consumed for its potential health-promoting properties. The health benefits of broccoli are partly associated with secondary plant compounds that have bioactivity; glucosinolates and phenolic acids are two of the most abundant and important in broccoli. In an effort to determine how variety, stress, and production conditions affect the production of these bioactive components broccoli was grown in the greenhouse with and without selenium (Se) fertilization, and in the field under conventional or organic farming procedures and with or without water stress. High-performance liquid chromatography/mass spectrometry was used to separate and identify 12 primary phenolic compounds. Variety had a major effect: There was a preponderance of flavonoids in the Majestic variety, but hydroxycinnamic esters were relatively more abundant in the Legacy variety. Organic farming and water stress decreased the overall production of phenolics. Se fertilization increased glucosinolates in general, and sulforaphane in particular, up to a point; above that Se fertilization decreased glucosinolate production. Organic farming and water stress also decreased glucosinolate production. These data show environmental and genetic variation in phenolics and glucosinolates in broccoli, and warn that not all broccoli may contain all health-promoting bioactive components. They further show that selection for one bioactive component (Se) may decrease the content of other bioactive components such as phenolics and glucosinolates. PMID:16117613

  6. The fusion of genomes leads to more options: A comparative investigation on the desulfo-glucosinolate sulfotransferases of Brassica napus and homologous proteins of Arabidopsis thaliana.

    PubMed

    Hirschmann, Felix; Papenbrock, Jutta

    2015-06-01

    Sulfotransferases (SOTs) (EC 2.8.2.-) play a crucial role in the glucosinolate (Gl) biosynthesis, by catalyzing the final step of the core glucosinolate formation. In Arabidopsis thaliana the three desulfo (ds)-Gl SOTs AtSOT16, AtSOT17 and AtSOT18 were previously characterized, showing different affinities to ds-Gls. But can the knowledge about these SOTs be generally transferred to other Gl-synthesizing plants? It was investigated how many SOTs are present in the economically relevant crop plant Brassica napus L., and if it is possible to predict their characteristics by sequence analysis. The recently sequenced B. napus is a hybrid of Brassica rapa and Brassica oleracea. By database research, 71 putative functional BnSOT family members were identified and at least eleven of those are putative ds-Gl SOTs. Besides the homologs of AtSOT16 - 18, phylogenetic analyses revealed new subfamilies of ds-Gl SOTs, which are not present in A. thaliana. Three of the B. napus ds-Gl SOT proteins were expressed and purified, and characterized by determining the substrate affinities to different ds-Gls. Two of them, BnSOT16-a and BnSOT16-b, showed a significantly higher affinity to an indolic ds-Gl, similarly to AtSOT16. Additionally, BnSOT17-a was characterized and showed a higher affinity to long chained aliphatic Gls, similarly to AtSOT17. Identification of homologs to AtSOT18 was less reliable, because putative SOT18 sequences are more heterogeneous and confirmation of similar characteristics was not possible. PMID:25827495

  7. 40 CFR 721.10534 - Brominated aliphatic alcohol (generic).

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Brominated aliphatic alcohol (generic... Specific Chemical Substances § 721.10534 Brominated aliphatic alcohol (generic). (a) Chemical substance and... aliphatic alcohol (PMN P-12-260) is subject to reporting under this section for the significant new...

  8. 40 CFR 721.10534 - Brominated aliphatic alcohol (generic).

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Brominated aliphatic alcohol (generic... Specific Chemical Substances § 721.10534 Brominated aliphatic alcohol (generic). (a) Chemical substance and... aliphatic alcohol (PMN P-12-260) is subject to reporting under this section for the significant new...

  9. 40 CFR 721.3520 - Aliphatic polyglycidyl ether.

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Aliphatic polyglycidyl ether. 721.3520... Substances § 721.3520 Aliphatic polyglycidyl ether. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance aliphatic polyglycidyl ether (PMN P-89-1036) is subject...

  10. 40 CFR 721.3520 - Aliphatic polyglycidyl ether.

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... 40 Protection of Environment 31 2011-07-01 2011-07-01 false Aliphatic polyglycidyl ether. 721.3520... Substances § 721.3520 Aliphatic polyglycidyl ether. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance aliphatic polyglycidyl ether (PMN P-89-1036) is subject...

  11. 40 CFR 721.2270 - Aliphatic dicarboxylic acid salt.

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... 40 Protection of Environment 31 2011-07-01 2011-07-01 false Aliphatic dicarboxylic acid salt. 721... Substances § 721.2270 Aliphatic dicarboxylic acid salt. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified generically as aliphatic dicarboxylic...

  12. 40 CFR 721.2270 - Aliphatic dicarboxylic acid salt.

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Aliphatic dicarboxylic acid salt. 721... Substances § 721.2270 Aliphatic dicarboxylic acid salt. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified generically as aliphatic dicarboxylic...

  13. 40 CFR 721.2270 - Aliphatic dicarboxylic acid salt.

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Aliphatic dicarboxylic acid salt. 721... Substances § 721.2270 Aliphatic dicarboxylic acid salt. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified generically as aliphatic dicarboxylic...

  14. 40 CFR 721.2270 - Aliphatic dicarboxylic acid salt.

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Aliphatic dicarboxylic acid salt. 721... Substances § 721.2270 Aliphatic dicarboxylic acid salt. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified generically as aliphatic dicarboxylic...

  15. 40 CFR 721.6140 - Dialkyldithiophosphoric acid, aliphatic amine salt.

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ..., aliphatic amine salt. 721.6140 Section 721.6140 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY... Specific Chemical Substances § 721.6140 Dialkyldithiophosphoric acid, aliphatic amine salt. (a) Chemical... as a dialkyldithiophosphoric acid, aliphatic amine salt (P-90-1839) is subject to reporting...

  16. 40 CFR 721.6140 - Dialkyldithiophosphoric acid, aliphatic amine salt.

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ..., aliphatic amine salt. 721.6140 Section 721.6140 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY... Specific Chemical Substances § 721.6140 Dialkyldithiophosphoric acid, aliphatic amine salt. (a) Chemical... as a dialkyldithiophosphoric acid, aliphatic amine salt (P-90-1839) is subject to reporting...

  17. 40 CFR 721.6140 - Dialkyldithiophosphoric acid, aliphatic amine salt.

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ..., aliphatic amine salt. 721.6140 Section 721.6140 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY... Specific Chemical Substances § 721.6140 Dialkyldithiophosphoric acid, aliphatic amine salt. (a) Chemical... as a dialkyldithiophosphoric acid, aliphatic amine salt (P-90-1839) is subject to reporting...

  18. 40 CFR 721.6140 - Dialkyldithiophosphoric acid, aliphatic amine salt.

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ..., aliphatic amine salt. 721.6140 Section 721.6140 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY... Specific Chemical Substances § 721.6140 Dialkyldithiophosphoric acid, aliphatic amine salt. (a) Chemical... as a dialkyldithiophosphoric acid, aliphatic amine salt (P-90-1839) is subject to reporting...

  19. 40 CFR 721.6140 - Dialkyldithiophosphoric acid, aliphatic amine salt.

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ..., aliphatic amine salt. 721.6140 Section 721.6140 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY... Specific Chemical Substances § 721.6140 Dialkyldithiophosphoric acid, aliphatic amine salt. (a) Chemical... as a dialkyldithiophosphoric acid, aliphatic amine salt (P-90-1839) is subject to reporting...

  20. Renaissance of Aliphatic Polycarbonates: New Techniques and Biomedical Applications

    PubMed Central

    Xu, Jianwen; Feng, Ellva; Song, Jie

    2014-01-01

    Aliphatic polycarbonates were discovered a long time ago, with their conventional applications mostly limited to low molecular weight oligomeric intermediates for copolymerization with other polymers. Recent developments in polymerization techniques have overcome the difficulty in preparing high molecular weight aliphatic polycarbonates. These in turn, along with new functional monomers, have enabled the preparation of a wide range of aliphatic polycarbonates with diverse chemical compositions and structures. This review summarizes the latest polymerization techniques for preparing well-defined functional aliphatic polycarbonates, as well as the new applications of those aliphatic polycarbonates, esecially in the biomedical field. PMID:24994939

  1. QTL Analysis Using SNP Markers Developed by Next-Generation Sequencing for Identification of Candidate Genes Controlling 4-Methylthio-3-Butenyl Glucosinolate Contents in Roots of Radish, Raphanus sativus L

    PubMed Central

    Zou, Zhongwei; Ishida, Masahiko; Li, Feng; Kakizaki, Tomohiro; Suzuki, Sho; Kitashiba, Hiroyasu; Nishio, Takeshi

    2013-01-01

    SNP markers for QTL analysis of 4-MTB-GSL contents in radish roots were developed by determining nucleotide sequences of bulked PCR products using a next-generation sequencer. DNA fragments were amplified from two radish lines by multiplex PCR with six primer pairs, and those amplified by 2,880 primer pairs were mixed and sequenced. By assembling sequence data, 1,953 SNPs in 750 DNA fragments, 437 of which have been previously mapped in a linkage map, were identified. A linkage map of nine linkage groups was constructed with 188 markers, and five QTLs were detected in two F2 populations, three of them accounting for more than 50% of the total phenotypic variance being repeatedly detected. In the identified QTL regions, nine SNP markers were newly produced. By synteny analysis of the QTLs regions with Arabidopsis thaliana and Brassica rapa genome sequences, three candidate genes were selected, i.e., RsMAM3 for production of aliphatic glucosinolates linked to GSL-QTL-4, RsIPMDH1 for leucine biosynthesis showing strong co-expression with glucosinolate biosynthesis genes linked to GSL-QTL-2, and RsBCAT4 for branched-chain amino acid aminotransferase linked to GSL-QTL-1. Nucleotide sequences and expression of these genes suggested their possible function in 4MTB-GSL biosynthesis in radish roots. PMID:23308250

  2. Glucosinolates in Diplotaxis and Eruca leaves: diversity, taxonomic relations and applied aspects.

    PubMed

    D'Antuono, L Filippo; Elementi, Simona; Neri, Roberta

    2008-01-01

    Leaf glucosinolates of 42 Diplotaxis and 21 Eruca accessions were studied. Total content ranged from 0.25 to more than 70 g kg(-1) dry wt. The 13 clusters, defined on the basis of glucosinolate composition, belonged to two glucosinolate-rich groups, characterised by the prevalence of a single component, and one low-glucosinolate group, with a profile not dominated by any individual component. A sinigrin-rich cluster (D. ibicensis, D. berthautii, D. ilorcitana, D. siettiana, D. tenuisiliqua, D. brevisiliqua, and D. virgata) and a gluconapin-rich cluster (D. catholica, D.siifolia, D. virgata, and D. ollivieri) included all the species previously classified in the nigra phylogenetic lineage. D. virgata was confirmed to be a critical taxon, with one accession slightly diverging from the others. D. siifolia subsp. vicentina was separated from the others in a glucobrassicin-rich cluster. D. harra, a rather isolated representative of sub-genus Hesperidium, clustered together D. assurgens in a sinalbin-rich cluster. Another well defined cluster was represented by D. brachycarpa (gluconasturtin). The two sub-species of D. erucoides were well differentiated by their glucosinolate profile. The low glucosinolate species: D. tenuifolia, D. viminea, D. cretacea, D. muralis (subgenus Diplotaxis), and E. vesicaria, all previously included in the rapa/oleracea lineage, belonged to seven less defined clusters, mainly differing on the presence/absence or the relative abundance of some components (glucoraphanin, glucolepidin, 4-hydroxy-glucobrassicin, 4-phenylbutyl gls, glucoerucin and neoglucobrassicin). The data support previous taxonomic works. Glucosinolate-rich taxa, with well characterised profiles may be suitable for industrial uses, whereas the variability of edible D. tenuifolia and E. vesicaria may represent a basis for breeding horticultural types. PMID:17669448

  3. Sinapis phylogeny and evolution of glucosinolates and specific nitrile degrading enzymes.

    PubMed

    Agerbirk, Niels; Warwick, Suzanne I; Hansen, Paul R; Olsen, Carl E

    2008-12-01

    Levels of sinalbin (4-hydroxybenzylglucosinolate) and 28 other glucosinolates were determined in leaves and roots of 20 species that were either phylogenetically close to Sinapis alba, Sinapis arvensis, or Sinapis pubescens (tribe Brassiceae, Brassicaceae), or were expected to contain arylalkyl nitrilase activity. Comparison with a molecular phylogenetic tree based on ITS DNA sequences identified two separate occurrences of sinalbin. The first in a group of species related to S. alba (including members of the genera Coincya and Kremeriella); and the second in S. arvensis, nested among sinalbin deficient species. Significant 4-hydroxyphenylacetonitrile degrading enzyme activity was found in both S. alba and S. arvensis, but in S. alba the major product was the corresponding carboxylic acid, while in S. arvensis the major product was the amide. Both investigated enzyme activities, nitrilase and nitrile hydratase, were specific, accepting only certain arylacetonitriles such as 4-hydroxy and 4-methoxyphenylacetonitrile. Only the S. alba enzyme required an oxygen in para position of the substrate, as found in sinalbin. Indole-3-acetonitrile, arylcyanides, and arylpropionitriles were poor substrates. The nitrilase activity of S. alba was quantitatively comparable to that reported in the monocot Sorghum bicolor (believed to be involved in cyanogenic glycoside metabolism). Glucosinolates derived from methionine were found in all Sinapis clades. Glucosinolate patterns suggested a complex evolution of glucosinolates in the investigated species, with several apparent examples of abrupt changes in glucosinolate profiles including chain length variation and appearance of glucosinolates derived from branched-chain amino acids. NMR data for desulfated homosinalbin, 9-methylsulphonylnonylglucosinolate, 3-methylpentylglucosinolate and related glucosinolates are reported, and a facultative connection between sinalbin and specific nitrilases is suggested. PMID:18995873

  4. Photolysis of aryl chlorides with aliphatic amines

    SciTech Connect

    Bunce, N.J.

    1982-05-07

    Kinetic arguments show that the aliphatic amine assisted photodechlorinations of chlorides of the benzene, naphthalene, and biphenyl series take place mainly from the triplet excited state. Deuterium labeling studies have been used to determine the origin of the hydrogen atom which replaces chlorine when 4-chlorobiphenyl is photoreduced. Three pathways are inferred: hydrogen abstraction from the solvent and protonation both within the exciplex (or radical ion pair) and by external proton donors.

  5. Individual biotransformation rates in chlorinated aliphatic mixtures

    SciTech Connect

    Hughes, J.B.; Parkin, G.F.

    1996-02-01

    Anaerobic biotransformation of chlorinated aliphatics has been widely studied over the past decade, and anaerobic bioremediation is considered a promising technique for restoration of contaminated aquifers. Studies using batch cultures and continuously fed attached-growth systems investigated the effect of mixtures of chlorinated aliphatics on the anaerobic biotransformation rates of individual components of the mixture. Dichloromethane (DCM), chloroform (CF), and 1,1,1-trichloroethane (TCA) were selected for study because of their frequent detection in groundwater. Biotransformation of CF and TCA occurred in all systems. When CF and TCA were fed together, transformation rates for both aliphatics were lower than when fed individually. DCM generally had minor to negligible effects on the transformation of CF and TCA, but in one case, it caused a slight but statistically significant decrease in TCA transformation (p = 0.05). DCM transformation was not observed when fed individually or in mixtures to batch resting cultures, so the effect of CF and TCA on DCM transformation could not be determined.

  6. Biosynthetic Studies on Water-Soluble Derivative 5c (DTX5c)

    PubMed Central

    Vilches, Tamara S.; Norte, Manuel; Daranas, Antonio Hernández; Fernández, José J.

    2012-01-01

    The dinoflagellate Prorocentrum belizeanum is responsible for the production of several toxins involved in the red tide phenomenon known as Diarrhetic Shellfish Poisoning (DSP). In this paper we report on the biosynthetic origin of an okadaic acid water-soluble ester derivative, DTX5c, on the basis of the spectroscopical analysis of 13C enriched samples obtained by addition of labelled sodium [l-13C], [2-13C] acetate to artificial cultures of this dinoflagellate. PMID:23170080

  7. Comparative analysis of quantitative trait loci controlling glucosinolates, myrosinase and insect resistance in Arabidopsis thaliana.

    PubMed Central

    Kliebenstein, Daniel; Pedersen, Deana; Barker, Bridget; Mitchell-Olds, Thomas

    2002-01-01

    Evolutionary interactions among insect herbivores and plant chemical defenses have generated systems where plant compounds have opposing fitness consequences for host plants, depending on attack by various insect herbivores. This interplay complicates understanding of fitness costs and benefits of plant chemical defenses. We are studying the role of the glucosinolate-myrosinase chemical defense system in protecting Arabidopsis thaliana from specialist and generalist insect herbivory. We used two Arabidopsis recombinant inbred populations in which we had previously mapped QTL controlling variation in the glucosinolate-myrosinase system. In this study we mapped QTL controlling resistance to specialist (Plutella xylostella) and generalist (Trichoplusia ni) herbivores. We identified a number of QTL that are specific to one herbivore or the other, as well as a single QTL that controls resistance to both insects. Comparison of QTL for herbivory, glucosinolates, and myrosinase showed that T. ni herbivory is strongly deterred by higher glucosinolate levels, faster breakdown rates, and specific chemical structures. In contrast, P. xylostella herbivory is uncorrelated with variation in the glucosinolate-myrosinase system. This agrees with evolutionary theory stating that specialist insects may overcome host plant chemical defenses, whereas generalists will be sensitive to these same defenses. PMID:12019246

  8. Natural variation in cross-talk between glucosinolates and onset of flowering in Arabidopsis

    PubMed Central

    Jensen, Lea M.; Jepsen, Henriette S. K.; Halkier, Barbara A.; Kliebenstein, Daniel J.; Burow, Meike

    2015-01-01

    Naturally variable regulatory networks control different biological processes including reproduction and defense. This variation within regulatory networks enables plants to optimize defense and reproduction in different environments. In this study we investigate the ability of two enzyme-encoding genes in the glucosinolate pathway, AOP2 and AOP3, to affect glucosinolate accumulation and flowering time. We have introduced the two highly similar enzymes into two different AOPnull accessions, Col-0 and Cph-0, and found that the genes differ in their ability to affect glucosinolate levels and flowering time across the accessions. This indicated that the different glucosinolates produced by AOP2 and AOP3 serve specific regulatory roles in controlling these phenotypes. While the changes in glucosinolate levels were similar in both accessions, the effect on flowering time was dependent on the genetic background pointing to natural variation in cross-talk between defense chemistry and onset of flowering. This variation likely reflects an adaptation to survival in different environments. PMID:26442014

  9. GLS-Finder: A Platform for Fast Profiling of Glucosinolates in Brassica Vegetables.

    PubMed

    Sun, Jianghao; Zhang, Mengliang; Chen, Pei

    2016-06-01

    Mass spectrometry combined with related tandem techniques has become the most popular method for plant secondary metabolite characterization. We introduce a new strategy based on in-database searching, mass fragmentation behavior study, formula predicting for fast profiling of glucosinolates, a class of important compounds in brassica vegetables. A MATLAB script-based expert system computer program, "GLS-Finder", was developed. It is capable of qualitative and semi-quantitative analyses of glucosinolates in samples using data generated by ultrahigh-performance liquid chromatography-high-resolution accurate mass with multi-stage mass fragmentation (UHPLC-HRAM/MS(n)). A suite of bioinformatic tools was integrated into the "GLS-Finder" to perform raw data deconvolution, peak alignment, glucosinolate putative assignments, semi-quantitation, and unsupervised principal component analysis (PCA). GLS-Finder was successfully applied to identify intact glucosinolates in 49 commonly consumed Brassica vegetable samples in the United States. It is believed that this work introduces a new way of fast data processing and interpretation for qualitative and quantitative analyses of glucosinolates, where great efficacy was improved in comparison to identification manually. PMID:27181885

  10. Profiling of Glucosinolates and Flavonoids in Rorippa indica (Linn.) Hiern. (Cruciferae) by UHPLC-PDA-ESI/HRMSn.

    Technology Transfer Automated Retrieval System (TEKTRAN)

    An UHPLC-DAD-ESI/HRMSn profiling method was used to identify the glucosinolates and flavonoids of Rorippa montana (Cruciferae), a Chinese herb used to treat cough, diarrhea and rheumatoid arthritis. Thirty three glucosinolates, over 40 flavonol glycosides, and more than 20 other phenolic and common ...

  11. Cytosolic γ-Glutamyl Peptidases Process Glutathione Conjugates in the Biosynthesis of Glucosinolates and Camalexin in Arabidopsis[W][OA

    PubMed Central

    Geu-Flores, Fernando; Møldrup, Morten Emil; Böttcher, Christoph; Olsen, Carl Erik; Scheel, Dierk; Halkier, Barbara Ann

    2011-01-01

    The defense-related plant metabolites known as glucosinolates play important roles in agriculture, ecology, and human health. Despite an advanced biochemical understanding of the glucosinolate pathway, the source of the reduced sulfur atom in the core glucosinolate structure remains unknown. Recent evidence has pointed toward GSH, which would require further involvement of a GSH conjugate processing enzyme. In this article, we show that an Arabidopsis thaliana mutant impaired in the production of the γ-glutamyl peptidases GGP1 and GGP3 has altered glucosinolate levels and accumulates up to 10 related GSH conjugates. We also show that the double mutant is impaired in the production of camalexin and accumulates high amounts of the camalexin intermediate GS-IAN upon induction. In addition, we demonstrate that the cellular and subcellular localization of GGP1 and GGP3 matches that of known glucosinolate and camalexin enzymes. Finally, we show that the purified recombinant GGPs can metabolize at least nine of the 10 glucosinolate-related GSH conjugates as well as GS-IAN. Our results demonstrate that GSH is the sulfur donor in the biosynthesis of glucosinolates and establish an in vivo function for the only known cytosolic plant γ-glutamyl peptidases, namely, the processing of GSH conjugates in the glucosinolate and camalexin pathways. PMID:21712415

  12. GLS-Finder: An Automated Data-Mining System for Fast Profiling Glucosinolates and its Application in Brassica Vegetables

    Technology Transfer Automated Retrieval System (TEKTRAN)

    A rapid computer-aided program for profiling glucosinolates, “GLS-Finder", was developed. GLS-Finder is a Matlab script based expert system that is capable for qualitative and semi-quantitative analysis of glucosinolates in samples using data generated by ultra-high performance liquid chromatograph...

  13. Feeding on Leaves of the Glucosinolate Transporter Mutant gtr1gtr2 Reduces Fitness of Myzus persicae.

    PubMed

    Madsen, Svend Roesen; Kunert, Grit; Reichelt, Michael; Gershenzon, Jonathan; Halkier, Barbara Ann

    2015-11-01

    As aphids are a pest on various crops worldwide, a better understanding of the interaction between aphids and plant host defenses is required. The green peach aphid (Myzus persicae) feeds on a variety of plant species, including the model plant Arabidopsis thaliana (Arabidopsis), in which glucosinolates function as a major part of the chemical defense. Several studies have shown that glucosinolates play a role in interactions between Arabidopsis and the green peach aphid. In this work, we used a recently identified Arabidopsis glucosinolate transporter mutant (gtr1gtr2 dKO), with altered glucosinolate content in the vasculature, to investigate the role of defense compound transport in aphid infestation. By monitoring aphid performance on caged leaves and analyzing glucosinolates in leaf tissue and phloem sap, as well as inside aphids, we examined if a change in spatial distribution of glucosinolates within a leaf influences aphid performance. Based on reduced glucosinolate content in the phloem sap of the transporter mutant, we hypothesized that aphids would perform better on gtr1gtr2 dKO leaves compared to WT. Unexpectedly, aphids performed poorly on gtr1gtr2 dKO leaves. Our data suggest that higher glucosinolate content in tissues surrounding the phloem of the double transporter mutant may play a role in reducing aphid performance on this genotype. PMID:26511863

  14. Determination of glucosinolates in traditional Chinese herbs by high-performance liquid chromatography and electrospray ionization mass spectrometry.

    PubMed

    Lee, Kim-Chung; Cheuk, Man-Wai; Chan, Wan; Lee, Albert Wai-Ming; Zhao, Zhong-Zhen; Jiang, Zhi-Hong; Cai, Zongwei

    2006-12-01

    A reversed-phase HPLC method has been developed for determination of twelve intact glucosinolates--glucoiberin, glucocheirolin, progoitrin, sinigrin, epiprogoitrin, glucoraphenin, sinalbin, gluconapin, glucosibarin, glucotropaeolin, glucoerucin, and gluconasturtiin--in ten traditional Chinese plants. The samples were extracted with methanol and the extracts were cleaned on an activated Florisil column. A mobile phase gradient prepared from methanol and 30 mmol L(-1) ammonium acetate at pH 5.0 enabled baseline separation of the glucosinolates. Glucosinolate detection was confirmed by quadrupole time-of-flight tandem mass spectrometric analysis in negative-ionization mode. Detection limits ranged from 0.06 to 0.36 microg g(-1) when 5 g of dried plant was analyzed. Recoveries of the glucosinolates were better than 85% and precision (relative standard derivation, n = 3) ranged from 5.3 to 14.6%. Analysis of the glucosinolates provided scientific evidence enabling differentiation of three pairs of easily confused plants. PMID:17086388

  15. Myrosinase-dependent and -independent formation and control of isothiocyanate products of glucosinolate hydrolysis.

    PubMed

    Angelino, Donato; Dosz, Edward B; Sun, Jianghao; Hoeflinger, Jennifer L; Van Tassell, Maxwell L; Chen, Pei; Harnly, James M; Miller, Michael J; Jeffery, Elizabeth H

    2015-01-01

    Brassicales contain a myrosinase enzyme that hydrolyzes glucosinolates to form toxic isothiocyanates (ITC), as a defense against bacteria, fungi, insects and herbivores including man. Low levels of ITC trigger a host defense system in mammals that protects them against chronic diseases. Because humans typically cook their brassica vegetables, destroying myrosinase, there is a great interest in determining how human microbiota can hydrolyze glucosinolates and release them, to provide the health benefits of ITC. ITC are highly reactive electrophiles, binding reversibly to thiols, but accumulating and causing damage when free thiols are not available. We found that addition of excess thiols released protein-thiol-bound ITC, but that the microbiome supports only poor hydrolysis unless exposed to dietary glucosinolates for a period of days. These findings explain why 3-5 servings a week of brassica vegetables may provide health effects, even if they are cooked. PMID:26500669

  16. Myrosinase-dependent and –independent formation and control of isothiocyanate products of glucosinolate hydrolysis

    PubMed Central

    Angelino, Donato; Dosz, Edward B.; Sun, Jianghao; Hoeflinger, Jennifer L.; Van Tassell, Maxwell L.; Chen, Pei; Harnly, James M.; Miller, Michael J.; Jeffery, Elizabeth H.

    2015-01-01

    Brassicales contain a myrosinase enzyme that hydrolyzes glucosinolates to form toxic isothiocyanates (ITC), as a defense against bacteria, fungi, insects and herbivores including man. Low levels of ITC trigger a host defense system in mammals that protects them against chronic diseases. Because humans typically cook their brassica vegetables, destroying myrosinase, there is a great interest in determining how human microbiota can hydrolyze glucosinolates and release them, to provide the health benefits of ITC. ITC are highly reactive electrophiles, binding reversibly to thiols, but accumulating and causing damage when free thiols are not available. We found that addition of excess thiols released protein-thiol-bound ITC, but that the microbiome supports only poor hydrolysis unless exposed to dietary glucosinolates for a period of days. These findings explain why 3–5 servings a week of brassica vegetables may provide health effects, even if they are cooked. PMID:26500669

  17. 26 CFR 5c.103-3 - Leases and arbitrage.

    Code of Federal Regulations, 2010 CFR

    2010-04-01

    ... 26 Internal Revenue 14 2010-04-01 2010-04-01 false Leases and arbitrage. 5c.103-3 Section 5c.103-3...) TEMPORARY INCOME TAX REGULATIONS UNDER THE ECONOMIC RECOVERY TAX ACT OF 1981 § 5c.103-3 Leases and arbitrage... the section 168(f)(8) lease transaction....

  18. Differing mechanisms of simple nitrile formation on glucosinolate degradation in Lepidium sativum and Nasturtium officinale seeds.

    PubMed

    Williams, David J; Critchley, Christa; Pun, Sharon; Chaliha, Mridusmita; O'Hare, Timothy J

    2009-01-01

    Glucosinolates are sulphur-containing glycosides found in brassicaceous plants that can be hydrolysed enzymatically by plant myrosinase or non-enzymatically to form primarily isothiocyanates and/or simple nitriles. From a human health perspective, isothiocyanates are quite important because they are major inducers of carcinogen-detoxifying enzymes. Two of the most potent inducers are benzyl isothiocyanate (BITC) present in garden cress (Lepidium sativum), and phenylethyl isothiocyanate (PEITC) present in watercress (Nasturtium officinale). Previous studies on these salad crops have indicated that significant amounts of simple nitriles are produced at the expense of the isothiocyanates. These studies also suggested that nitrile formation may occur by different pathways: (1) under the control of specifier protein in garden cress and (2) by an unspecified, non-enzymatic path in watercress. In an effort to understand more about the mechanisms involved in simple nitrile formation in these species, we analysed their seeds for specifier protein and myrosinase activities, endogenous iron content and glucosinolate degradation products after addition of different iron species, specific chelators and various heat treatments. We confirmed that simple nitrile formation was predominantly under specifier protein control (thiocyanate-forming protein) in garden cress seeds. Limited thermal degradation of the major glucosinolate, glucotropaeolin (benzyl glucosinolate), occurred when seed material was heated to >120 degrees C. In the watercress seeds, however, we show for the first time that gluconasturtiin (phenylethyl glucosinolate) undergoes a non-enzymatic, iron-dependent degradation to a simple nitrile. On heating the seeds to 120 degrees C or greater, thermal degradation of this heat-labile glucosinolate increased simple nitrile levels many fold. PMID:19747700

  19. Possible evolution of alliarinoside biosynthesis from the glucosinolate pathway in Alliaria petiolata.

    PubMed

    Frisch, Tina; Møller, Birger L

    2012-05-01

    Nitrile formation in plants involves the activity of cytochrome P450s. Hydroxynitrile glucosides are widespread among plants but generally do not occur in glucosinolate producing species. Alliaria petiolata (garlic mustard, Brassicaceae) is the only species known to produce glucosinolates as well as a γ-hydroxynitrile glucoside. Furthermore, A. petiolata has been described to release diffusible cyanide, which indicates the presence of unidentified cyanogenic glucoside(s). Our research on A. petiolata addresses the molecular evolution of P450s. By integrating current knowledge about glucosinolate and hydroxynitrile glucoside biosynthesis in other species and new visions on recurrent evolution of hydroxynitrile glucoside biosynthesis, we propose a pathway for biosynthesis of the γ-hydroxynitrile glucoside, alliarinoside. Homomethionine and the corresponding oxime are suggested as shared intermediates in the biosynthesis of alliarinoside and 2-propenyl glucosinolate. The first committed step in the alliarinoside pathway is envisioned to be catalysed by a P450, which has been recruited to metabolize the oxime. Furthermore, alliarinoside biosynthesis is suggested to involve enzyme activities common to secondary modification of glucosinolates. Thus, we argue that biosynthesis of alliarinoside may be the first known case of a hydroxynitrile glucoside pathway having evolved from the glucosinolate pathway. An intriguing question is whether the proposed hydroxynitrile intermediate may also be converted to novel homomethionine-derived cyanogenic glucoside(s), which could release cyanide. Elucidation of the pathway for biosynthesis of alliarinoside and other putative hydroxynitrile glucosides in A. petiolata is envisioned to offer significant new knowledge on the emerging picture of P450 functional dynamics as a basis for recurrent evolution of pathways for bioactive natural product biosynthesis. PMID:22212644

  20. Transcriptome and Metabolome Analyses of Glucosinolates in Two Broccoli Cultivars Following Jasmonate Treatment for the Induction of Glucosinolate Defense to Trichoplusia ni (Hübner).

    PubMed

    Ku, Kang-Mo; Becker, Talon M; Juvik, John A

    2016-01-01

    Lepidopteran larvae growth is influenced by host plant glucosinolate (GS) concentrations, which are, in turn, influenced by the phytohormone jasmonate (JA). In order to elucidate insect resistance biomarkers to lepidopteran pests, transcriptome and metabolome analyses following JA treatments were conducted with two broccoli cultivars, Green Magic and VI-158, which have differentially induced indole GSs, neoglucobrassicin and glucobrassicin, respectively. To test these two inducible GSs on growth of cabbage looper (Trichoplusia ni), eight neonate cabbage looper larvae were placed onto each of three plants per JA treatments (0, 100, 200, 400 µM) three days after treatment. After five days of feeding, weight of larvae and their survival rate was found to decrease with increasing JA concentrations in both broccoli cultivars. JA-inducible GSs were measured by high performance liquid chromatography. Neoglucobrassicin in Green Magic and glucobrassicin in VI-158 leaves were increased in a dose-dependent manner. One or both of these glucosinolates and/or their hydrolysis products showed significant inverse correlations with larval weight and survival (five days after treatment) while being positively correlated with the number of days to pupation. This implies that these two JA-inducible glucosinolates can influence the growth and survival of cabbage looper larvae. Transcriptome profiling supported the observed changes in glucosinolate and their hydrolysis product concentrations following JA treatments. Several genes related to GS metabolism differentiate the two broccoli cultivars in their pattern of transcriptional response to JA treatments. Indicative of the corresponding change in indole GS concentrations, transcripts of the transcription factor MYB122, core structure biosynthesis genes (CYP79B2, UGT74B1, SUR1, SOT16, SOT17, and SOT18), an indole glucosinolate side chain modification gene (IGMT1), and several glucosinolate hydrolysis genes (TGG1, TGG2, and ESM1) were

  1. Transcriptome and Metabolome Analyses of Glucosinolates in Two Broccoli Cultivars Following Jasmonate Treatment for the Induction of Glucosinolate Defense to Trichoplusia ni (Hübner)

    PubMed Central

    Ku, Kang-Mo; Becker, Talon M.; Juvik, John A.

    2016-01-01

    Lepidopteran larvae growth is influenced by host plant glucosinolate (GS) concentrations, which are, in turn, influenced by the phytohormone jasmonate (JA). In order to elucidate insect resistance biomarkers to lepidopteran pests, transcriptome and metabolome analyses following JA treatments were conducted with two broccoli cultivars, Green Magic and VI-158, which have differentially induced indole GSs, neoglucobrassicin and glucobrassicin, respectively. To test these two inducible GSs on growth of cabbage looper (Trichoplusia ni), eight neonate cabbage looper larvae were placed onto each of three plants per JA treatments (0, 100, 200, 400 µM) three days after treatment. After five days of feeding, weight of larvae and their survival rate was found to decrease with increasing JA concentrations in both broccoli cultivars. JA-inducible GSs were measured by high performance liquid chromatography. Neoglucobrassicin in Green Magic and glucobrassicin in VI-158 leaves were increased in a dose-dependent manner. One or both of these glucosinolates and/or their hydrolysis products showed significant inverse correlations with larval weight and survival (five days after treatment) while being positively correlated with the number of days to pupation. This implies that these two JA-inducible glucosinolates can influence the growth and survival of cabbage looper larvae. Transcriptome profiling supported the observed changes in glucosinolate and their hydrolysis product concentrations following JA treatments. Several genes related to GS metabolism differentiate the two broccoli cultivars in their pattern of transcriptional response to JA treatments. Indicative of the corresponding change in indole GS concentrations, transcripts of the transcription factor MYB122, core structure biosynthesis genes (CYP79B2, UGT74B1, SUR1, SOT16, SOT17, and SOT18), an indole glucosinolate side chain modification gene (IGMT1), and several glucosinolate hydrolysis genes (TGG1, TGG2, and ESM1) were

  2. Spreading coefficients of aliphatic hydrocarbons on water

    SciTech Connect

    Takii, Taichi; Mori, Y.H. . Dept. of Mechanical Engineering)

    1993-11-01

    Experiments have been performed to determine the equilibrium spreading coefficients of some aliphatic hydrocarbons (C[sub 6]C[sub 10]) on water. The thickness of a discrete lens of each hydrocarbon sample floating on a stagnant water pool was measured interferometrically and used to calculate the spreading coefficient of the hydrocarbon with the aid of Langmuir's capillarity theory. The dependences of the spreading coefficient, thus observed, on temperature (0--50 C) and on the number of carbon atoms in the hydrocarbon molecule are in qualitative agreement with the predictions based on the Lifshitz theory of van der Waals forces.

  3. Aliphatic hydrocarbons of the Murchison meteorite

    NASA Technical Reports Server (NTRS)

    Cronin, John R.; Pizzarello, Sandra

    1990-01-01

    Hydrocarbon fractions from the Murchison meteorite were prepared using benzene-methanol as the extraction solvent, fractionated on silica gel columns, and analyzed using gas chromatography combined with mass spectrometry and IR and NMR techniques. Results indicate that the most abundant aliphatic hydrocarbon components of the Murchison meteorite are C15 to C30 branched-alkyl-substituted mono-, di-, and tricyclic alkanes. It is shown that the n-alkanes, methyl alkanes, and isoprenoid alkanes that are sometimes found in extracts of the Murchison meteorite are terrestrial contaminants.

  4. Glucosinolates in collard greens grown under three soil management practices.

    PubMed

    Antonious, George F

    2015-01-01

    Glucosinolates (GSLs, β-D-thioglucoside-N-hydroxysulfates) are polar compounds present in varying amounts in members of the Brassicaceae family. They suppress soil-borne pests due to the biofumigant properties of the highly toxic isothiocyanates present in Brassica vegetables. The objectives of this investigation were to: (1) assess variation in GSLs concentrations among collard plants grown under three soil management practices: sewage sludge (SS) mixed with native soil, chicken manure (CM) mixed with native soil, and no-mulch (NM) native soil, (2) quantify GSLs concentrations in collard roots, leaves, and stems at harvest for potential use of their crude extracts in plant protection, and (3) assess myrosinase activity in soil amended with CM and SS mixed with native soil. Separation of GSLs was accomplished by adsorption on a DEAE-Sephadex ion exchange resin using disposable pipette tips filled with DEAE, a weak base, with a net positive charge when ionized and exchange anions such as GSLs (hydrophilic plant secondary metabolites). Quantification of total GSLs was based on inactivation of collard endogenous myrosinase and liberation of the glucose moiety from the GSLs molecule by addition of standardized myrosinase and colorimetric determination of the liberated glucose moiety. Across all treatments, SS and CM increased soil organic matter content from 2.2% in native soil to 4.2 and 6.5%, respectively. GSLs concentrations were significantly greater in collard leaves (30.9 µmoles g(-1) fresh weight) compared to roots and stems (7.8 and 1.2 µmoles g(-1) fresh weight), respectively. Leaves of collard grown in soil amended with SS contained the greatest concentrations of GSLs compared to leaves of plants grown in CM and NM treatments. Accordingly, leaves of collard plants grown in soil amended with SS could play a significant role in sustainable agriculture as alternative tools for soil-borne disease management in conventional and organic agriculture. PMID

  5. Multifunctional aliphatic polyester nanofibers for tissue engineering.

    PubMed

    Zhan, Jianan; Singh, Anirudha; Zhang, Zhe; Huang, Ling; Elisseeff, Jennifer H

    2012-01-01

    Electrospun fibers based on aliphatic polyesters, such as poly(ε-caprolactone) (PCL), have been widely used in regenerative medicine and drug delivery applications due to their biocompatibility, low cost and ease of fabrication. However, these aliphatic polyester fibers are hydrophobic in nature, resulting in poor wettability, and they lack functional groups for decorating the scaffold with chemical and biological cues. Current strategies employed to overcome these challenges include coating and blending the fibers with bioactive components or chemically modifying the fibers with plasma treatment and reactants. In the present study, we report on designing multifunctional electrospun nanofibers based on the inclusion complex of PCL-α-cyclodextrin (PCL-α-CD), which provides both structural support and multiple functionalities for further conjugation of bioactive components. This strategy is independent of any chemical modification of the PCL main chain, and electrospinning of PCL-α-CD is as easy as electrospinning PCL. Here, we describe synthesis of the PCL-α-CD electrospun nanofibers, elucidate composition and structure, and demonstrate the utility of functional groups on the fibers by conjugating a fluorescent small molecule and a polymeric-nanobead to the nanofibers. Furthermore, we demonstrate the application of PCL-α-CD nanofibers for promoting osteogenic differentiation of human adipose-derived stem cells (hADSCs), which induced a higher level of expression of osteogenic markers and enhanced production of extracellular matrix (ECM) proteins or molecules compared with control PCL fibers. PMID:23507886

  6. Degradation of Biofumigant Isothiocyanates and Allyl Glucosinolate in Soil and Their Effects on the Microbial Community Composition

    PubMed Central

    Hanschen, Franziska S.; Yim, Bunlong; Winkelmann, Traud; Smalla, Kornelia; Schreiner, Monika

    2015-01-01

    Brassicales species rich in glucosinolates are used for biofumigation, a process based on releasing enzymatically toxic isothiocyanates into the soil. These hydrolysis products are volatile and often reactive compounds. Moreover, glucosinolates can be degraded also without the presence of the hydrolytic enzyme myrosinase which might contribute to bioactive effects. Thus, in the present study the stability of Brassicaceae plant-derived and pure glucosinolates hydrolysis products was studied using three different soils (model biofumigation). In addition, the degradation of pure 2-propenyl glucosinolate was investigated with special regard to the formation of volatile breakdown products. Finally, the influence of pure glucosinolate degradation on the bacterial community composition was evaluated using denaturing gradient gel electrophoresis of 16S rRNA gene amplified from total community DNA. The model biofumigation study revealed that the structure of the hydrolysis products had a significant impact on their stability in the soil but not the soil type. Following the degradation of pure 2-propenyl glucosinolate in the soils, the nitrile as well as the isothiocyanate can be the main degradation products, depending on the soil type. Furthermore, the degradation was shown to be both chemically as well as biologically mediated as autoclaving reduced degradation. The nitrile was the major product of the chemical degradation and its formation increased with iron content of the soil. Additionally, the bacterial community composition was significantly affected by adding pure 2-propenyl glucosinolate, the effect being more pronounced than in treatments with myrosinase added to the glucosinolate. Therefore, glucosinolates can have a greater effect on soil bacterial community composition than their hydrolysis products. PMID:26186695

  7. Modification of Leaf Glucosinolate Contents in Brassica oleracea by Divergent Selection and Effect on Expression of Genes Controlling Glucosinolate Pathway.

    PubMed

    Sotelo, Tamara; Velasco, Pablo; Soengas, Pilar; Rodríguez, Víctor M; Cartea, María E

    2016-01-01

    Modification of the content of secondary metabolites opens the possibility of obtaining vegetables enriched in these compounds related to plant defense and human health. We report the first results of a divergent selection for glucosinolate (GSL) content of the three major GSL in leaves: sinigrin (SIN), glucoiberin (GIB), and glucobrassicin (GBS) in order to develop six kale genotypes (Brassica oleracea var. acephala) with high (HSIN, HIGIB, HGBS) and low (LSIN, LGIB, LGBS) content. The aims were to determine if the three divergent selections were successful in leaves, how each divergent selection affected the content of the same GSLs in flower buds and seeds and to determine which genes would be involved in the modification of the content of the three GSL studied. The content of SIN and GIB after three cycles of divergent selection increased 52.5% and 77.68%, and decreased 51.9% and 45.33%, respectively. The divergent selection for GBS content was only successful and significant for decreasing the concentration, with a reduction of 39.04%. Mass selection is an efficient way of modifying the concentration of individual GSLs. Divergent selections realized in leaves had a side effect in the GSL contents of flower buds and seeds due to the novo synthesis in these organs and/or translocation from leaves. The results obtained suggest that modification in the SIN and GIB concentration by selection is related to the GSL-ALK locus. We suggest that this locus could be related with the indirect response found in the GBS concentration. Meantime, variations in the CYP81F2 gene expression could be the responsible of the variations in GBS content. The genotypes obtained in this study can be used as valuable materials for undertaking basic studies about the biological effects of the major GSLs present in kales. PMID:27471510

  8. Protection of humans by plant glucosinolates: efficiency of conversion of glucosinolates to isothiocyanates by the gastrointestinal microflora.

    PubMed

    Fahey, Jed W; Wehage, Scott L; Holtzclaw, W David; Kensler, Thomas W; Egner, Patricia A; Shapiro, Theresa A; Talalay, Paul

    2012-04-01

    Plant-based diets rich in crucifers are effective in preventing cancer and other chronic diseases. Crucifers contain very high concentrations of glucosinolates (GS; β-thioglucoside-N-hydroxysulfates). Although not themselves protective, GS are converted by coexisting myrosinases to bitter isothiocyanates (ITC) which defend plants against predators. Coincidentally, ITC also induce mammalian genes that regulate defenses against oxidative stress, inflammation, and DNA-damaging electrophiles. Consequently, the efficiency of conversion of GS to ITC may be critical in controlling the health-promoting benefits of crucifers. If myrosinase is heat-inactivated by cooking, the gastrointestinal microflora converts GS to ITC, a process abolished by enteric antibiotics and bowel cleansing. When single oral doses of GS were administered as broccoli sprout extracts (BSE) to two dissimilar populations (rural Han Chinese and racially mixed Baltimoreans) patterns of excretions of urinary dithiocarbamates (DTC) were very similar. Individual conversions in both populations varied enormously, from about 1% to more than 40% of dose. In contrast, administration of ITC (largely sulforaphane)-containing BSE resulted in uniformly high (70%-90%) conversions to urinary DTC. Despite the remarkably large range of conversion efficiencies between individuals, repeated determinations within individuals were much more consistent. The rates of urinary excretion (slow or fast) were unrelated to the ultimate magnitudes (low or high) of these conversions. Although no demographic factors affecting conversion efficiency have been identified, there are clearly diurnal variations: conversion of GS to DTC was greater during the day, but conversion of ITC to DTC was more efficient at night. PMID:22318753

  9. Modification of Leaf Glucosinolate Contents in Brassica oleracea by Divergent Selection and Effect on Expression of Genes Controlling Glucosinolate Pathway

    PubMed Central

    Sotelo, Tamara; Velasco, Pablo; Soengas, Pilar; Rodríguez, Víctor M.; Cartea, María E.

    2016-01-01

    Modification of the content of secondary metabolites opens the possibility of obtaining vegetables enriched in these compounds related to plant defense and human health. We report the first results of a divergent selection for glucosinolate (GSL) content of the three major GSL in leaves: sinigrin (SIN), glucoiberin (GIB), and glucobrassicin (GBS) in order to develop six kale genotypes (Brassica oleracea var. acephala) with high (HSIN, HIGIB, HGBS) and low (LSIN, LGIB, LGBS) content. The aims were to determine if the three divergent selections were successful in leaves, how each divergent selection affected the content of the same GSLs in flower buds and seeds and to determine which genes would be involved in the modification of the content of the three GSL studied. The content of SIN and GIB after three cycles of divergent selection increased 52.5% and 77.68%, and decreased 51.9% and 45.33%, respectively. The divergent selection for GBS content was only successful and significant for decreasing the concentration, with a reduction of 39.04%. Mass selection is an efficient way of modifying the concentration of individual GSLs. Divergent selections realized in leaves had a side effect in the GSL contents of flower buds and seeds due to the novo synthesis in these organs and/or translocation from leaves. The results obtained suggest that modification in the SIN and GIB concentration by selection is related to the GSL-ALK locus. We suggest that this locus could be related with the indirect response found in the GBS concentration. Meantime, variations in the CYP81F2 gene expression could be the responsible of the variations in GBS content. The genotypes obtained in this study can be used as valuable materials for undertaking basic studies about the biological effects of the major GSLs present in kales. PMID:27471510

  10. 40 CFR 721.2270 - Aliphatic dicarboxylic acid salt.

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Aliphatic dicarboxylic acid salt. 721... Substances § 721.2270 Aliphatic dicarboxylic acid salt. (a) Chemical substance and significant new uses... salt (PMN P-92-1352) is subject to reporting under this section for the significant new uses...

  11. 40 CFR 721.4497 - Aliphatic polyisocyanates (generic name).

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... 40 Protection of Environment 31 2011-07-01 2011-07-01 false Aliphatic polyisocyanates (generic name). 721.4497 Section 721.4497 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY (CONTINUED... Specific Chemical Substances § 721.4497 Aliphatic polyisocyanates (generic name). (a) Chemical...

  12. 40 CFR 721.4497 - Aliphatic polyisocyanates (generic name).

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Aliphatic polyisocyanates (generic name). 721.4497 Section 721.4497 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY (CONTINUED... Specific Chemical Substances § 721.4497 Aliphatic polyisocyanates (generic name). (a) Chemical...

  13. 40 CFR 721.4497 - Aliphatic polyisocyanates (generic name).

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Aliphatic polyisocyanates (generic name). 721.4497 Section 721.4497 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY (CONTINUED... Specific Chemical Substances § 721.4497 Aliphatic polyisocyanates (generic name). (a) Chemical...

  14. 40 CFR 721.4497 - Aliphatic polyisocyanates (generic name).

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Aliphatic polyisocyanates (generic name). 721.4497 Section 721.4497 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY (CONTINUED... Specific Chemical Substances § 721.4497 Aliphatic polyisocyanates (generic name). (a) Chemical...

  15. 40 CFR 721.4497 - Aliphatic polyisocyanates (generic name).

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Aliphatic polyisocyanates (generic name). 721.4497 Section 721.4497 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY (CONTINUED... Specific Chemical Substances § 721.4497 Aliphatic polyisocyanates (generic name). (a) Chemical...

  16. Epithiospecifier protein activity in broccoli: the link between terminal alkenyl glucosinolates and sulphoraphane nitrile.

    PubMed

    Williams, David J; Critchley, Christa; Pun, Sharon; Nottingham, Stephen; O'Hare, Timothy J

    2008-11-01

    The chemical nature of the hydrolysis products from the glucosinolate-myrosinase system depends on the presence or absence of supplementary proteins, such as epithiospecifier proteins (ESPs). ESPs (non-catalytic cofactors of myrosinase) promote the formation of epithionitriles from terminal alkenyl glucosinolates and as recent evidence suggests, simple nitriles at the expense of isothiocyanates. The ratio of ESP activity to myrosinase activity is crucial in determining the proportion of these nitriles produced on hydrolysis. Sulphoraphane, a major isothiocyanate produced in broccoli seedlings, has been found to be a potent inducer of phase 2 detoxification enzymes. However, ESP may also support the formation of the non-inductive sulphoraphane nitrile. Our objective was to monitor changes in ESP activity during the development of broccoli seedlings and link these activity changes with myrosinase activity, the level of terminal alkenyl glucosinolates and sulphoraphane nitrile formed. Here, for the first time, we show ESP activity increases up to day 2 after germination before decreasing again to seed activity levels at day 5. These activity changes paralleled changes in myrosinase activity and terminal alkenyl glucosinolate content. There is a significant relationship between ESP activity and the formation of sulforaphane nitrile in broccoli seedlings. The significance of these findings for the health benefits conferred by eating broccoli seedlings is briefly discussed. PMID:18977005

  17. Myrosinase-dependent and –independent formation and control of isothiocyanate products of glucosinolate hydrolysis

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Brassicales contain a myrosinase enzyme that hydrolyzes glucosinolates to form toxic isothiocyanates, as a defense against bacteria, fungi, insects and herbivores including man. Low levels of isothiocyanates trigger a host defense system in mammals that protects them against chronic diseases. Becaus...

  18. Barbarea vulgaris Glucosinolate Phenotypes Differentially Affect Performance and Preference of Two Different Species of Lepidopteran Herbivores

    PubMed Central

    Vet, Louise E. M.; van der Putten, Wim H.; van Dam, Nicole M.

    2008-01-01

    The composition of secondary metabolites and the nutritional value of a plant both determine herbivore preference and performance. The genetically determined glucosinolate pattern of Barbarea vulgaris can be dominated by either glucobarbarin (BAR-type) or by gluconasturtiin (NAS-type). Because of the structural differences, these glucosinolates may have different effects on herbivores. We compared the two Barbarea chemotypes with regards to the preference and performance of two lepidopteran herbivores, using Mamestra brassicae as a generalist and Pieris rapae as a specialist. The generalist and specialist herbivores did not prefer either chemotype for oviposition. However, larvae of the generalist M. brassicae preferred to feed and performed best on NAS-type plants. On NAS-type plants, 100% of the M. brassicae larvae survived while growing exponentially, whereas on BAR-type plants, M. brassicae larvae showed little growth and a mortality of 37.5%. In contrast to M. brassicae, the larval preference and performance of the specialist P. rapae was unaffected by plant chemotype. Total levels of glucosinolates, water soluble sugars, and amino acids of B. vulgaris could not explain the poor preference and performance of M. brassicae on BAR-type plants. Our results suggest that difference in glucosinolate chemical structure is responsible for the differential effects of the B. vulgaris chemotypes on the generalist herbivore. Electronic supplementary material The online version of this article (doi:10.1007/s10886-007-9424-9) contains supplementary material, which is available to authorized users. PMID:18213497

  19. [Determination of benzyl glucosinolate in Lepidium meyenii from different regions by HPLC].

    PubMed

    Tang, Lin; Yin, Hong-jun; Si, Cong-cong; Hu, Xiao-yan; Long, Zheng-hai

    2015-12-01

    The content of benzyl isothiocyanate (BITC) which as the enzymatic hydrolysis product of benzyl glucosinolate through thioglucosidase was determined by HPLC. The content of benzyl isothiocyanate (BITC) which as the enzymatic hydrolysis product of benzyl glucosinolate through thioglucosidase was determined by HPLC. The chromatography condition was as follows: Kaseisorb LC ODS 2000 (4.6 mm x 150 mm, 5 min) column with the mobile phase of acetonitrile(A)-water( B) under gradient elution (0-5 min, 3%-8% A; 5-9 min, 8%-48% A; 9-23 min, 48%-62% A; 23-28 min, 62%-99% A); the flow rate was 1.0 mL x min(-1) with 10 microL injection volume; detection wavelength was 246 nm and temperature of column was 40 degrees C. The content of benzyl glucosinolate was in the range of 10.76-17.91 g x L(-1). The method is simple, accurate and good reproducibility which can be used for the determination of benzyl glucosinolate in Lepidium meyenii, effectively. PMID:27141661

  20. Arbuscular mycorrhizal fungi affect glucosinolate and mineral element composition in leaves of Moringa oleifera.

    PubMed

    Cosme, Marco; Franken, Philipp; Mewis, Inga; Baldermann, Susanne; Wurst, Susanne

    2014-10-01

    Moringa is a mycorrhizal crop cultivated in the tropics and subtropics and appreciated for its nutritive and health-promoting value. As well as improving plant mineral nutrition, arbuscular mycorrhizal fungi (AMF) can affect plant synthesis of compounds bioactive against chronic diseases in humans. Rhizophagus intraradices and Funneliformis mosseae were used in a full factorial experiment to investigate the impact of AMF on the accumulation of glucosinolates, flavonoids, phenolic acids, carotenoids, and mineral elements in moringa leaves. Levels of glucosinolates were enhanced, flavonoids and phenolic acids were not affected, levels of carotenoids (including provitamin A) were species-specifically reduced, and mineral elements were affected differently, with only Cu and Zn being increased by the AMF. This study presents novel results on AMF effects on glucosinolates in leaves and supports conclusions that the impacts of these fungi on microelement concentrations in edible plants are species dependent. The nonspecific positive effects on glucosinolates and the species-specific negative effects on carotenoids encourage research on other AMF species to achieve general benefits on bioactive compounds in moringa. PMID:24706008

  1. Glucosinolate content and nematicidal activity of Brazilian wild mustard tissues against Meloidogyne incognita in tomato

    Technology Transfer Automated Retrieval System (TEKTRAN)

    The wild mustard (Brassica juncea L.), an invasive weed of winter crops in Brazil, was evaluated for glucosinolate content of its plant tissues and nematicidal activity of its dry leaf meal (LM), whole seed meal (WSM) and hexane defatted seed meal (DSM) against Meloidogyne incognita on tomato plants...

  2. Reduction of total glucosinolates in canola meal via thermal treatment and fungal bioprocessing

    Technology Transfer Automated Retrieval System (TEKTRAN)

    On a worldwide basis, canola (Brassica napus) meal is second only to soybean meal as a protein source for livestock. A general limitation of Brassica spp. meals is the presence of glucosinolates (GLS). GLS and the enzyme myrosinase are compartmentally stored separately in the plant. Upon disruption ...

  3. Development of a generalist predator, Podisus maculiventris, on glucosinolate sequestering and nonsequestering prey

    NASA Astrophysics Data System (ADS)

    van Geem, Moniek; Harvey, Jeffrey A.; Gols, Rieta

    2014-09-01

    Insect herbivores exhibit various strategies to counter the toxic effects of plant chemical defenses. These strategies include the detoxification, excretion, and sequestration of plant secondary metabolites. The latter strategy is often considered to provide an additional benefit in that it provides herbivores with protection against natural enemies such as predators. Profiles of sequestered chemicals are influenced by the food plants from which these chemicals are derived. We compared the effects of sequestration and nonsequestration of plant secondary metabolites in two specialist herbivores on the development of a generalist predator, Podisus maculiventris. Profiles of glucosinolates, secondary metabolites characteristic for the Brassicaceae, are known to differ considerably both inter- and intraspecifically. Throughout their immature (=nymphal) development, the predator was fed on larval stages of either sequestering (turnip sawfly, Athalia rosae) or nonsequestering (small cabbage white butterfly, Pieris rapae) prey that in turn had been feeding on plants originating from three wild cabbage ( Brassica oleracea) populations that have previously been shown to differ in their glucosinolate profiles. We compared survival, development time, and adult body mass as parameters for bug performance. Our results show that sequestration of glucosinolates by A. rosae only marginally affected the development of P. maculiventris. The effects of plant population on predator performance were variable. We suggest that sequestration of glucosinolates by A. rosae functions not only as a defensive mechanism against some predators, but may also be an alternative way of harmlessly dealing with plant allelochemicals.

  4. Involvement of Cytochrome P450 in Glucosinolate Biosynthesis in White Mustard (A Biochemical Anomaly).

    PubMed Central

    Bennett, R. N.; Kiddle, G.; Wallsgrove, R. M.

    1997-01-01

    One of the first steps in glucosinolate biosynthesis is the conversion of amino acids to their aldoximes. The biochemistry of this process is controversial, and several very different enzyme systems have been described. The major glucosinolate in white mustard (Sinapis alba) is sinalbin, which is derived from tyrosine via its aldoxime, and this conversion is catalyzed by a cytochrome P450 (Cyt P450) monooxygenase. Phenylethyl- and alkenylglucosinolates are also present in white mustard leaves, as are the enzymes catalyzing the relevant aldoxime formation from homophenylalanine and methionine homologs, respectively. These enzymes are similar to those found in Brassica sp. and are distinct from the tyrosine-dependent enzyme in that they contain no heme and are unaffected by Cyt P450 inhibitors. They are instead inhibited by the flavoprotein inhibitor diphenylene iodonium and by Cu2+. In both white mustard and oilseed rape (Brassica napus) methyl jasmonate specifically stimulates indolylglucosinolate biosynthesis and yet has no effect on sinalbin accumulation in either cotyledons or leaves of white mustard. White mustard appears to be unique among crucifers in having a Cyt P450 aldoxime-forming enzyme for biosynthesis of one glucosinolate, although it also contains all of the non-Cyt P450 enzyme systems found in other members of the family. Sinalbin biosynthesis in white mustard is therefore an inappropriate model system for the synthesis of other glucosinolates in crucifers, including canola and oilseed rape. PMID:12223771

  5. Involvement of Cytochrome P450 in Glucosinolate Biosynthesis in White Mustard (A Biochemical Anomaly).

    PubMed

    Bennett, R. N.; Kiddle, G.; Wallsgrove, R. M.

    1997-08-01

    One of the first steps in glucosinolate biosynthesis is the conversion of amino acids to their aldoximes. The biochemistry of this process is controversial, and several very different enzyme systems have been described. The major glucosinolate in white mustard (Sinapis alba) is sinalbin, which is derived from tyrosine via its aldoxime, and this conversion is catalyzed by a cytochrome P450 (Cyt P450) monooxygenase. Phenylethyl- and alkenylglucosinolates are also present in white mustard leaves, as are the enzymes catalyzing the relevant aldoxime formation from homophenylalanine and methionine homologs, respectively. These enzymes are similar to those found in Brassica sp. and are distinct from the tyrosine-dependent enzyme in that they contain no heme and are unaffected by Cyt P450 inhibitors. They are instead inhibited by the flavoprotein inhibitor diphenylene iodonium and by Cu2+. In both white mustard and oilseed rape (Brassica napus) methyl jasmonate specifically stimulates indolylglucosinolate biosynthesis and yet has no effect on sinalbin accumulation in either cotyledons or leaves of white mustard. White mustard appears to be unique among crucifers in having a Cyt P450 aldoxime-forming enzyme for biosynthesis of one glucosinolate, although it also contains all of the non-Cyt P450 enzyme systems found in other members of the family. Sinalbin biosynthesis in white mustard is therefore an inappropriate model system for the synthesis of other glucosinolates in crucifers, including canola and oilseed rape. PMID:12223771

  6. Development of a generalist predator, Podisus maculiventris, on glucosinolate sequestering and nonsequestering prey.

    PubMed

    van Geem, Moniek; Harvey, Jeffrey A; Gols, Rieta

    2014-09-01

    Insect herbivores exhibit various strategies to counter the toxic effects of plant chemical defenses. These strategies include the detoxification, excretion, and sequestration of plant secondary metabolites. The latter strategy is often considered to provide an additional benefit in that it provides herbivores with protection against natural enemies such as predators. Profiles of sequestered chemicals are influenced by the food plants from which these chemicals are derived. We compared the effects of sequestration and nonsequestration of plant secondary metabolites in two specialist herbivores on the development of a generalist predator, Podisus maculiventris. Profiles of glucosinolates, secondary metabolites characteristic for the Brassicaceae, are known to differ considerably both inter- and intraspecifically. Throughout their immature (=nymphal) development, the predator was fed on larval stages of either sequestering (turnip sawfly, Athalia rosae) or nonsequestering (small cabbage white butterfly, Pieris rapae) prey that in turn had been feeding on plants originating from three wild cabbage (Brassica oleracea) populations that have previously been shown to differ in their glucosinolate profiles. We compared survival, development time, and adult body mass as parameters for bug performance. Our results show that sequestration of glucosinolates by A. rosae only marginally affected the development of P. maculiventris. The effects of plant population on predator performance were variable. We suggest that sequestration of glucosinolates by A. rosae functions not only as a defensive mechanism against some predators, but may also be an alternative way of harmlessly dealing with plant allelochemicals. PMID:25008387

  7. Glucosinolates Are Mainly Absorbed Intact in Germfree and Human Microbiota-Associated Mice.

    PubMed

    Budnowski, Julia; Hanske, Laura; Schumacher, Fabian; Glatt, Hansruedi; Platz, Stefanie; Rohn, Sascha; Blaut, Michael

    2015-09-30

    Chemoprotective or genotoxic effects of glucosinolates occurring in Brassica vegetables are attributed to their hydrolysis products formed upon tissue damage by plant myrosinase. Since Brassica vegetables, in which myrosinase has been heat-inactivated, still display bioactivity, glucosinolate activation has been attributed to intestinal bacteria. The aim of this study was to investigate whether this is true. Glucoraphanin (172 mg/kg body weight) and neoglucobrassicin (297 mg/kg body weight) were administered intragastrically to germ free and human microbiota associated (HMA) mice. Approximately 30% of the applied doses of glucoraphanin and neoglucobrassicin were excreted unchanged in the urine of both germ free and HMA mice. Isothiocyanates, sulforaphane, and erucin, formed from glucoraphanin, were mainly excreted as urinary N-acetyl-l-cysteine conjugates. N-Methoxyindole-3-carbinol formed from neoglucobrassicin was observed in small amounts in both germ free and HMA mice. Formation of DNA adducts from neoglucobrassicin was also independent from bacterial colonization of the mice. Hence, intestinal bacteria are involved in the bioactivation of glucosinolates in the gut, but their contribution to glucosinolate transformation in HMA mice is apparently very small. PMID:26365197

  8. An Update on Potential Perspectives of Glucosinolates on Protection against Microbial Pathogens and Endocrine Dysfunctions in Humans.

    PubMed

    Baskar, Venkidasamy; Park, Se Won; Nile, Shivraj Hariram

    2016-10-01

    Glucosinolates are the major bioactive secondary metabolites found in the Brassicaceae family and studied extensively in biosynthetic and application perspectives. Because of their potential applications in the welfare of plants (protection against plant pathogens) and human life (prevention of cancer and other diseases), these compounds attracted much interest in the scientific community. In this review, we presented updates on glucosinolate derivatives in protection against microbial pathogens and endocrine related diseases in human. Further, the mechanism of action of glucosinolate derivatives and the strategies to improve their efficiency through modern approaches were discussed. Finally, the genetic enrichment of their contents in plant systems has also been discussed. PMID:25629545

  9. Methyl Jasmonate- and Light-Induced Glucosinolate and Anthocyanin Biosynthesis in Radish Seedlings.

    PubMed

    Al-Dhabi, Naif Abdullah; Arasu, Mariadhas Valan; Kim, Sun Ju; RomijUddin, Md; Park, Woo Tae; Lee, Sook Young; Park, Sang Un

    2015-07-01

    Radish sprouts and young seedlings are considered important dietary vegetables in Asian countries. In this study, we investigated the levels of glucosinolate and anthocyanin accumulation in radish seedlings in response to light and methyl jasmonate (MeJA) treatments. MeJA facilitated the accumulation of glucosinolate and anthocyanins under light conditions. The glucosinolate and anthocyanin contents in the radish seedlings that were exposed to light after MeJA treatment were higher than those of the seedlings that were grown in the dark without MeJA. At a concentration of 100 μM, MeJA led to the greatest accumulation of the most glucosinolates under both light and dark conditions. Under light conditions, the levels of glucoraphenin, glucoerucin, and glucotropaeolin accumulation were 1.53-, 1.60-, and 1.30-fold higher, respectively, than those of the control. Remarkable accumulations of glucobrassicin were observed under light conditions (4.4-, 6.7-, and 7.8-fold higher than that of the control following the application of 100, 300, and 500 μM MeJA, respectively). The level of cyanidin in the 300 μM MeJA-treated seedlings was double of that in the control without MeJA treatment. The highest level of pelargonidin was observed after treatment with 500 μM MeJA under light conditions; this level was 1.73 times higher than that in the control. A similar trend of anthocyaninaccumulation was observed in the radish seedlings following MeJA treatment under dark conditions, but the levels of anthocyanins were considerably lower in the seedlings that were grown in the dark. Our findings suggest that light and low concentrations of MeJA enhance the accumulations of glucosinolates and anthocyanins during the development of radish seedlings. PMID:26411013

  10. Rapid incorporation of glucosinolates as a strategy used by a herbivore to prevent activation by myrosinases.

    PubMed

    Abdalsamee, Mohamed K; Giampà, Marco; Niehaus, Karsten; Müller, Caroline

    2014-09-01

    Various plants have a binary defence system that consists of a substrate and a glucosidase, which is activated upon tissue disruption thereby forming reactive hydrolysis products. Insects feeding on such plants have to overcome this binary defence system or prevent the activation. In this study, we investigated the strategy used by a herbivore to deal with such binary defence. We studied, how the larvae of the sawfly Athalia rosae (Hymenoptera: Tenthredinidae) circumvent the activation of glucosinolates by myrosinase enzymes, which are found in their Brassicaceae host plants. Myrosinase activities were low in the front part of the larval gut but activities increased over the gut passage. In contrast, the glucosinolates were only highly concentrated in the first gut part and were rapidly incorporated into the haemolymph before the food reached the second half of the gut. Thus, the uptake and concentration of glucosinolates, i.e., sequestration, must occur in the front part of the gut. Using Matrix Assisted Laser Desorption Ionization-Mass Spectrometry Imaging (MALDI-MSI), we could demonstrate that the incorporated glucosinolate sinalbin circulates in the haemolymph where it accumulates around the Malpighian tubules. This study highlights the pivotal role of the gut of an adapted herbivore as a regulatory functional organ to cope with plant toxins. MALDI-MSI turned out as a highly useful technique to visualise glucosinolates in a herbivore, which has to deal with plants exhibiting a binary defence system, and may be applied to follow the fate of plant metabolites in other insect species in the future. PMID:25017143

  11. Induced production of 1-methoxy-indol-3-ylmethyl glucosinolate by jasmonic acid and methyl jasmonate in sprouts and leaves of pak choi (Brassica rapa ssp. chinensis).

    PubMed

    Wiesner, Melanie; Hanschen, Franziska S; Schreiner, Monika; Glatt, Hansruedi; Zrenner, Rita

    2013-01-01

    Pak choi plants (Brassica rapa ssp. chinensis) were treated with different signaling molecules methyl jasmonate, jasmonic acid, linolenic acid, and methyl salicylate and were analyzed for specific changes in their glucosinolate profile. Glucosinolate levels were quantified using HPLC-DAD-UV, with focus on induction of indole glucosinolates and special emphasis on 1-methoxy-indol-3-ylmethyl glucosinolate. Furthermore, the effects of the different signaling molecules on indole glucosinolate accumulation were analyzed on the level of gene expression using semi-quantitative realtime RT-PCR of selected genes. The treatments with signaling molecules were performed on sprouts and mature leaves to determine ontogenetic differences in glucosinolate accumulation and related gene expression. The highest increase of indole glucosinolate levels, with considerable enhancement of the 1-methoxy-indol-3-ylmethyl glucosinolate content, was achieved with treatments of sprouts and mature leaves with methyl jasmonate and jasmonic acid. This increase was accompanied by increased expression of genes putatively involved in the indole glucosinolate biosynthetic pathway. The high levels of indole glucosinolates enabled the plant to preferentially produce the respective breakdown products after tissue damage. Thus, pak choi plants treated with methyl jasmonate or jasmonic acid, are a valuable tool to analyze the specific protection functions of 1-methoxy-indole-3-carbinole in the plants defense strategy in the future. PMID:23873294

  12. Induced Production of 1-Methoxy-indol-3-ylmethyl Glucosinolate by Jasmonic Acid and Methyl Jasmonate in Sprouts and Leaves of Pak Choi (Brassica rapa ssp. chinensis)

    PubMed Central

    Wiesner, Melanie; Hanschen, Franziska S.; Schreiner, Monika; Glatt, Hansruedi; Zrenner, Rita

    2013-01-01

    Pak choi plants (Brassica rapa ssp. chinensis) were treated with different signaling molecules methyl jasmonate, jasmonic acid, linolenic acid, and methyl salicylate and were analyzed for specific changes in their glucosinolate profile. Glucosinolate levels were quantified using HPLC-DAD-UV, with focus on induction of indole glucosinolates and special emphasis on 1-methoxy-indol-3-ylmethyl glucosinolate. Furthermore, the effects of the different signaling molecules on indole glucosinolate accumulation were analyzed on the level of gene expression using semi-quantitative realtime RT-PCR of selected genes. The treatments with signaling molecules were performed on sprouts and mature leaves to determine ontogenetic differences in glucosinolate accumulation and related gene expression. The highest increase of indole glucosinolate levels, with considerable enhancement of the 1-methoxy-indol-3-ylmethyl glucosinolate content, was achieved with treatments of sprouts and mature leaves with methyl jasmonate and jasmonic acid. This increase was accompanied by increased expression of genes putatively involved in the indole glucosinolate biosynthetic pathway. The high levels of indole glucosinolates enabled the plant to preferentially produce the respective breakdown products after tissue damage. Thus, pak choi plants treated with methyl jasmonate or jasmonic acid, are a valuable tool to analyze the specific protection functions of 1-methoxy-indole-3-carbinole in the plants defense strategy in the future. PMID:23873294

  13. Validation of Alternatives to Aliphatic Isocyanate Polyurethanes

    NASA Technical Reports Server (NTRS)

    Curran, Jerome

    2007-01-01

    The National Aeronautics and Space Administration (NASA) Headquarters chartered the Acquisition Pollution Prevention (AP2) Office to coordinate agency activities affecting pollution prevention issues identified during system and component acquisition and sustainment processes. The primary objective of this effort is to demonstrate and validate alternatives to aliphatic isocyanate polyurethane coatings. Successful completion of this project will result in one or more isocyanate-free coating systems qualified for use at Air Force Space Command (AFSPC) and NASA centers participating in this study. The objective of this project is to qualify the candidates under the specifications for the standard system. This project will compare coating performance of the proposed alternatives to existing coating systems or standards.

  14. Polyimide nanofoams from aliphatic polyester based copolymers

    SciTech Connect

    Hedrick, J.L.; Carter, K.R.; Richter, R.; Russell, T.P.

    1996-10-01

    High temperature polymer foams were prepared using microphase separated block copolymers where the major component is thermally stable block and the minor component is thermally labile. Upon thermal treatment, the dispersed minor component undergoes thermolysis leaving pores the size and shape of which are dictated by the initial copolymer morphology. The driving force behind the survey of aliphatic polyesters as possible labile blocks stems from their quantitative degradation into low boiling, polar degradation products via a backbiting process. Block copolymers were prepared using either a monofunctional caprolactone or a valerolactone oligomer and a high T. polyimide. Microphase morphologies were observed in each case. Thermal decomposition of the polyester blocks was accomplished by a thermal treatment at 370{degrees}C for 5 h. Significant density reductions were measured, and the resulting foams showed pore sizes in the 60-70 {Angstrom} range.

  15. Stable isotope investigations of chlorinated aliphatic hydrocarbons.

    SciTech Connect

    Abrajano, T.; Heraty, L. J.; Holt, B. D.; Huang, L.; Sturchio, N. C.

    1999-06-01

    Stable isotope ratio measurements for carbon (C) and chlorine (Cl) can be used to elucidate the processes affecting transformation and transportation of chlorinated aliphatic hydrocarbons (CAHs) in the environment. Methods recently developed in our laboratory for isotopic analysis of CAHs have been applied to laboratory measurements of the kinetic isotope effects associated with aerobic degradation of dichloromethane (DCM) and with both anaerobic and aerobic cometabolic degradation of trichlomethene (TCE) in batch and column microbial cultures. These experimental determinations of fractionation factors are crucial for understanding the behavior of CAHs in complex natural systems, where the extent of biotransformation can be masked by dispersion and volatilization. We have also performed laboratory investigations of kinetic isotope effects accompanying evaporation of CAHs, as well as field investigations of natural attenuation and in situ remediation of CAHs in a number of contaminated shallow aquifers at sites operated by the federal government and the private sector.

  16. The Transcript and Metabolite Networks Affected by the Two Clades of Arabidopsis Glucosinolate Biosynthesis Regulators1[W

    PubMed Central

    Malitsky, Sergey; Blum, Eyal; Less, Hadar; Venger, Ilya; Elbaz, Moshe; Morin, Shai; Eshed, Yuval; Aharoni, Asaph

    2008-01-01

    In this study, transcriptomics and metabolomics data were integrated in order to examine the regulation of glucosinolate (GS) biosynthesis in Arabidopsis (Arabidopsis thaliana) and its interface with pathways of primary metabolism. Our genetic material for analyses were transgenic plants overexpressing members of two clades of genes (ALTERED TRYPTOPHAN REGULATION1 [ATR1]-like and MYB28-like) that regulate the aliphatic and indole GS biosynthetic pathways (AGs and IGs, respectively). We show that activity of these regulators is not restricted to the metabolic space surrounding GS biosynthesis but is tightly linked to more distal metabolic networks of primary metabolism. This suggests that with similarity to the regulators we have investigated here, other factors controlling pathways of secondary metabolism might also control core pathways of central metabolism. The relatively broad view of transcripts and metabolites altered in transgenic plants overexpressing the different factors underlined novel links of GS metabolism to additional metabolic pathways, including those of jasmonic acid, folate, benzoic acid, and various phenylpropanoids. It also revealed transcriptional and metabolic hubs in the “distal” network of metabolic pathways supplying precursors to GS biosynthesis and that overexpression of the ATR1-like clade genes has a much broader effect on the metabolism of indolic compounds than described previously. While the reciprocal, negative cross talk between the methionine and tryptophan pathways that generate GSs in Arabidopsis has been suggested previously, we now show that it is not restricted to AGs and IGs but includes additional metabolites, such as the phytoalexin camalexin. Combining the profiling data of transgenic lines with gene expression correlation analysis allowed us to propose a model of how the balance in the metabolic network is maintained by the GS biosynthesis regulators. It appears that ATR1/MYB34 is an important mediator between the

  17. Major Signaling Pathways Modulate Arabidopsis Glucosinolate Accumulation and Response to Both Phloem-Feeding and Chewing Insects1

    PubMed Central

    Mewis, Inga; Appel, Heidi M.; Hom, Amanda; Raina, Ramesh; Schultz, Jack C.

    2005-01-01

    Plant responses to enemies are coordinated by several interacting signaling systems. Molecular and genetic studies with mutants and exogenous signal application suggest that jasmonate (JA)-, salicylate (SA)-, and ethylene (ET)-mediated pathways modulate expression of portions of the defense phenotype in Arabidopsis (Arabidopsis thaliana), but have not yet linked these observations directly with plant responses to insect attack. We compared the glucosinolate (GS) profiles of rosette leaves of 4-week-old mutant and transgenic Arabidopsis (Columbia) plants compromised in these three major signaling pathways, and characterized responses by those plants to feeding by two phloem-feeding aphids (generalist Myzus persicae and specialist Brevicoryne brassicae) and one generalist caterpillar species (Spodoptera exigua Hubner). Blocked JA signaling in coronatine-insensitive (coi1) and enhanced expression of SA-signaled disease resistance in hypersensitive response-like (hrl1) mutants reduced constitutive GS concentrations, while blocking SA signaling at the mediator protein npr1 mutant (NPR) increased them. There was no significant impact on constitutive GS contents of blocking ET signaling (at ET resistant [etr1]) or reducing SA concentrations (nahG transgene). We found increased GS accumulation in response to insect feeding, which required functional NPR1 and ETR1 but not COI1 or SA. Insect feeding caused increases primarily in short-chain aliphatic methylsulfinyl GS. By contrast, responses to exogenous JA, a frequent experimental surrogate for insect attack, were characterized by an increase in indolyl GS. Insect performance, measured as population increase or weight increase, was negatively related to GS levels, but we found evidence that other, ET-regulated factors may also be influential. Plant resistance to (consumption by) S. exigua was not related to insect growth because some plant chemistries inhibited growth while others inhibited feeding. These major signaling

  18. Composites of vinyl polystyrylpyridine/bismaleimide-aliphatic ether copolymers

    NASA Technical Reports Server (NTRS)

    Heimbuch, Alvin H.; Rosser, Robert W.; Hsu, Ming-Ta S.

    1989-01-01

    An aliphatic ether bismaleimide was prepared and coreacted with a polyvinylstyrylpyridine (VPSP) oligomer. Studies showed that a controlled ratio of aliphatic to aromatic units in the polymer backbone improved both processibility and interlaminar shear properties for the carbon-fiber composite system. This modified resin was readily soluble in tetrahydrofuran, allowing for better fiber impregnation and thus enhancing adhesive properties and reproducibility. DSC studies have shown a lower cure temperature for the copolymer than for the neat aliphatic bismaleimide, and a glass transition temperature of 260 C, which is more than adequate for most applications. Limited measurements indicated an improvement in toughness (impact resistance).

  19. Ontogenetic changes of 2-propenyl and 3-indolylmethyl glucosinolates in Brassica carinata leaves as affected by water supply.

    PubMed

    Schreiner, Monika; Beyene, Blen; Krumbein, Angelika; Stützel, Hartmut

    2009-08-26

    Concentrations of 2-propenyl and 3-indolylmethyl glucosinolates in two lines of Brassica carinata (Holeta-1 and 37-A) were assessed during the vegetative life cycle under optimal or drought-inducing water supply conditions. In the well-watered treatment, 2-propenyl and 3-indolylmethyl glucosinolate concentrations remained almost constant from the 6-8 to the 15-16 leaf stage, whereas a drought-induced water supply led to a distinct increase of these glucosinolates. Generally, the 2-propenyl concentration was higher in Holeta-1 at each leaf stage under drought stress as compared with 37-A, indicating a B. carinata line-specific drought response. The drought-induced glucosinolate accumulation seems to be integrated in the plant's process of osmotic adjustment. It seems that under drought, there is a shift from primary to secondary metabolism, thereby promoting glucosinolate synthesis. Thus, by keeping the relative soil-water content below 80%, glucosinolate concentrations could be increased up to the 15-16 leaf stage, resulting in better plant nutritional quality of B. carinata. PMID:20349919

  20. A human homologue of monkey F5c

    PubMed Central

    Ferri, S.; Peeters, R.; Nelissen, K.; Vanduffel, W.; Rizzolatti, G.; Orban, G.A.

    2015-01-01

    Area F5c is a monkey premotor area housing mirror neurons which responds more strongly to grasping observation when the actor is visible than when only the actor's hand is visible. Here we used this characteristic fMRI signature of F5c in seven imaging experiments – one in macaque monkeys and six in humans – to identify the human homologue of monkey F5c. By presenting the two grasping actions (actor, hand) and varying the low level visual characteristics, we localized a putative human homologue of area F5c (phF5c) in the inferior part of precentral sulcus, bilaterally. In contrast to monkey F5c, phF5c is asymmetric, with a right-sided bias, and is activated more strongly during the observation of the later stages of grasping when the hand is close to the object. The latter characteristic might be related to the emergence, in humans, of the capacity to precisely copy motor acts performed by others, and thus imitation. PMID:25711137

  1. ANAEROBIC AND AEROBIC TREATMENT OF CHLORINATED ALIPHATIC COMPOUNDS

    EPA Science Inventory

    Biological degradation of 12 chlorinated aliphatic compounds (CACs) was assessed in bench-top reactors and in serum bottle tests. Three continuously mixed daily batch-fed reactor systems were evaluated: anaerobic, aerobic, and sequential-anaerobic-aerobic (sequential). Glucose,...

  2. m5C RNA and m5C DNA methyl transferases use different cysteine residues as catalysts.

    PubMed

    Liu, Y; Santi, D V

    2000-07-18

    A family of RNA m(5)C methyl transferases (MTases) containing over 55 members in eight subfamilies has been identified recently by an iterative search of the genomic sequence databases by using the known 16S rRNA m(5)C 967 MTase, Fmu, as an initial probe. The RNA m(5)C MTase family contained sequence motifs that were highly homologous to motifs in the DNA m(5)C MTases, including the ProCys sequence that contains the essential Cys catalyst of the functionally similar DNA-modifying enzymes; it was reasonable to assign the Cys nucleophile to be that in the conserved ProCys. The family also contained an additional conserved Cys residue that aligns with the nucleophilic catalyst in m(5)U54 tRNA MTase. Surprisingly, the mutant of the putative Cys catalyst in the ProCys sequence was active and formed a covalent complex with 5-fluorocytosine-containing RNA, whereas the mutant at the other conserved Cys was inactive and unable to form the complex. Thus, notwithstanding the highly homologous sequences and similar functions, the RNA m(5)C MTase uses a different Cys as a catalytic nucleophile than the DNA m(5)C MTases. The catalytic Cys seems to be determined, not by the target base that is modified, but by whether the substrate is DNA or RNA. The function of the conserved ProCys sequence in the RNA m(5)C MTases remains unknown. PMID:10899996

  3. m5C RNA and m5C DNA methyl transferases use different cysteine residues as catalysts

    PubMed Central

    Liu, Yaoquan; Santi, Daniel V.

    2000-01-01

    A family of RNA m5C methyl transferases (MTases) containing over 55 members in eight subfamilies has been identified recently by an iterative search of the genomic sequence databases by using the known 16S rRNA m5C 967 MTase, Fmu, as an initial probe. The RNA m5C MTase family contained sequence motifs that were highly homologous to motifs in the DNA m5C MTases, including the ProCys sequence that contains the essential Cys catalyst of the functionally similar DNA-modifying enzymes; it was reasonable to assign the Cys nucleophile to be that in the conserved ProCys. The family also contained an additional conserved Cys residue that aligns with the nucleophilic catalyst in m5U54 tRNA MTase. Surprisingly, the mutant of the putative Cys catalyst in the ProCys sequence was active and formed a covalent complex with 5-fluorocytosine-containing RNA, whereas the mutant at the other conserved Cys was inactive and unable to form the complex. Thus, notwithstanding the highly homologous sequences and similar functions, the RNA m5C MTase uses a different Cys as a catalytic nucleophile than the DNA m5C MTases. The catalytic Cys seems to be determined, not by the target base that is modified, but by whether the substrate is DNA or RNA. The function of the conserved ProCys sequence in the RNA m5C MTases remains unknown. PMID:10899996

  4. Evaluation of antibacterial activity of synthetic aliphatic and aromatic monoacylglycerols.

    PubMed

    Batovska, Daniela; Todorova, Iva; Parushev, Stoyan; Tsvetkova, Iva; Najdenski, Hristo; Ubukata, Makoto

    2008-01-01

    The antibacterial activity of synthetic aliphatic and aromatic monoacylglycerols (MAGs) was studied against two human pathogens: Staphylococcus aureus and Escherichia coli. The active compounds inhibited selectively S. aureus. The most active compounds amongst them were those with medium size aliphatic chain and aromatic MAGs with electron withdrawing substituents at the aryl ring. The introduction of one or two-carbon spacer between the aryl ring and the carboxylic function did not influence antibacterial effectiveness. PMID:19004249

  5. Process for producing peracids from aliphatic hydroxy carboxylic acids

    DOEpatents

    Chum, H.L.; Palasz, P.D.; Ratcliff, M.A.

    1984-12-20

    A process is described for producing peracids from lactic acid-containing solutions derived from biomass processing systems. It consists of adjusting the pH of the solution to about 8 to 9 and removing alkaline residue fractions therefrom to form a solution comprised substantially of lower aliphatic hydroxy acids. The solution is oxidized to produce volatile lower aliphatic aldehydes. The aldehydes are removed as they are generated and converted to peracids.

  6. Process for producing peracids from aliphatic hydroxy carboxylic acids

    DOEpatents

    Chum, Helena L.; Ratcliff, Matthew A.; Palasz, Peter D.

    1986-01-01

    A process for producing peracids from lactic acid-containing solutions derived from biomass processing systems comprising: adjusting the pH of the solution to about 8-9 and removing alkaline residue fractions therefrom to form a solution comprised substantially of lower aliphatic hydroxy acids; oxidizing the solution to produce volatile lower aliphatic aldehydes; removing said aldehydes as they are generated; and converting said aldehydes to peracids.

  7. Allelopathic effects of glucosinolate breakdown products in Hanza [Boscia senegalensis (Pers.) Lam.] processing waste water.

    PubMed

    Rivera-Vega, Loren J; Krosse, Sebastian; de Graaf, Rob M; Garvi, Josef; Garvi-Bode, Renate D; van Dam, Nicole M

    2015-01-01

    Boscia senegalensis is a drought resistant shrub whose seeds are used in West Africa as food. However, the seeds, or hanza, taste bitter which can be cured by soaking them in water for 4-7 days. The waste water resulting from the processing takes up the bitter taste, which makes it unsuitable for consumption. When used for irrigation, allelopathic effects were observed. Glucosinolates and their breakdown products are the potential causes for both the bitter taste and the allelopathic effects. The objectives of this study are to identify and quantify the glucosinolates present in processed and unprocessed hanza as well as different organs of B. senegalensis, to analyze the chemical composition of the processing water, and to pinpoint the causal agent for the allelopathic properties of the waste water. Hanza (seeds without testa), leaves, branches, unripe, and ripe fruits were collected in three populations and subjected to glucosinolate analyses. Methylglucosinolates (MeGSL) were identified in all plant parts and populations, with the highest concentrations being found in the hanza. The levels of MeGSLs in the hanza reduced significantly during the soaking process. Waste water was collected for 6 days and contained large amounts of macro- and micronutrients, MeGSL as well as methylisothiocyanate (MeITC), resulting from the conversion of glucosinolates. Waste water from days 1-3 (High) and 4-6 (Low) was pooled and used to water seeds from 11 different crops to weeds. The High treatment significantly delayed or reduced germination of all the plant species tested. Using similar levels of MeITC as detected in the waste water, we found that germination of a subset of the plant species was inhibited equally to the waste water treatments. This confirmed that the levels of methylisiothiocyanate in the waste water were sufficient to cause the allelopathic effect. This leads to the possibility of using hanza waste water in weed control programs. PMID:26236325

  8. Allelopathic effects of glucosinolate breakdown products in Hanza [Boscia senegalensis (Pers.) Lam.] processing waste water

    PubMed Central

    Rivera-Vega, Loren J.; Krosse, Sebastian; de Graaf, Rob M.; Garvi, Josef; Garvi-Bode, Renate D.; van Dam, Nicole M.

    2015-01-01

    Boscia senegalensis is a drought resistant shrub whose seeds are used in West Africa as food. However, the seeds, or hanza, taste bitter which can be cured by soaking them in water for 4–7 days. The waste water resulting from the processing takes up the bitter taste, which makes it unsuitable for consumption. When used for irrigation, allelopathic effects were observed. Glucosinolates and their breakdown products are the potential causes for both the bitter taste and the allelopathic effects. The objectives of this study are to identify and quantify the glucosinolates present in processed and unprocessed hanza as well as different organs of B. senegalensis, to analyze the chemical composition of the processing water, and to pinpoint the causal agent for the allelopathic properties of the waste water. Hanza (seeds without testa), leaves, branches, unripe, and ripe fruits were collected in three populations and subjected to glucosinolate analyses. Methylglucosinolates (MeGSL) were identified in all plant parts and populations, with the highest concentrations being found in the hanza. The levels of MeGSLs in the hanza reduced significantly during the soaking process. Waste water was collected for 6 days and contained large amounts of macro- and micronutrients, MeGSL as well as methylisothiocyanate (MeITC), resulting from the conversion of glucosinolates. Waste water from days 1–3 (High) and 4–6 (Low) was pooled and used to water seeds from 11 different crops to weeds. The High treatment significantly delayed or reduced germination of all the plant species tested. Using similar levels of MeITC as detected in the waste water, we found that germination of a subset of the plant species was inhibited equally to the waste water treatments. This confirmed that the levels of methylisiothiocyanate in the waste water were sufficient to cause the allelopathic effect. This leads to the possibility of using hanza waste water in weed control programs. PMID:26236325

  9. The Arabidopsis Epithiospecifier Protein Promotes the Hydrolysis of Glucosinolates to Nitriles and Influences Trichoplusia ni Herbivory

    PubMed Central

    Lambrix, Virginia; Reichelt, Michael; Mitchell-Olds, Thomas; Kliebenstein, Daniel J.; Gershenzon, Jonathan

    2001-01-01

    Glucosinolates are anionic thioglucosides that have become one of the most frequently studied groups of defensive metabolites in plants. When tissue damage occurs, the thioglucoside linkage is hydrolyzed by enzymes known as myrosinases, resulting in the formation of a variety of products that are active against herbivores and pathogens. In an effort to learn more about the molecular genetic and biochemical regulation of glucosinolate hydrolysis product formation, we analyzed leaf samples of 122 Arabidopsis ecotypes. A distinct polymorphism was observed with all ecotypes producing primarily isothiocyanates or primarily nitriles. The ecotypes Columbia (Col) and Landsberg erecta (Ler) differed in their hydrolysis products; therefore, the Col × Ler recombinant inbred lines were used for mapping the genes controlling this polymorphism. The major quantitative trait locus (QTL) affecting nitrile versus isothiocyanate formation was found very close to a gene encoding a homolog of a Brassica napus epithiospecifier protein (ESP), which causes the formation of epithionitriles instead of isothiocyanates during glucosinolate hydrolysis in the seeds of certain Brassicaceae. The heterologously expressed Arabidopsis ESP was able to convert glucosinolates both to epithionitriles and to simple nitriles in the presence of myrosinase, and thus it was more versatile than previously described ESPs. The role of ESP in plant defense is uncertain, because the generalist herbivore Trichoplusia ni (the cabbage looper) was found to feed more readily on nitrile-producing than on isothiocyanate-producing Arabidopsis. However, isothiocyanates are frequently used as recognition cues by specialist herbivores, and so the formation of nitriles instead of isothiocyanates may allow Arabidopsis to be less apparent to specialists. PMID:11752388

  10. Optimizing elicitation and seed priming to enrich broccoli and radish sprouts in glucosinolates.

    PubMed

    Baenas, Nieves; Villaño, Debora; García-Viguera, Cristina; Moreno, Diego A

    2016-08-01

    Elicitation is a cheaper and socially acceptable tool for improving plant food functionality. Our objective was to optimize the treatment doses of the elicitors: methyl jasmonate (MeJA), jasmonic acid (JA) and DL-methionine (MET), in order to find a successful and feasible treatment to produce broccoli and radish sprouts with enhanced levels of health-promoting glucosinolates. Also a priming of seeds as a novel strategy to trigger the glucosinolates content was carried out with water (control), MeJA (250μM), JA (250μM) and MET (10mM) before the elicitor exogenous treatment. The results showed that almost all treatments could enhance effectively the total glucosinolates content in the sprouts, achieving the most significant increases from 34% to 100% of increase in broccoli and from 45% to 118% of increase in radish sprouts after MeJA priming and treatments. Consequently, our work demonstrates the feasibility of using elicitors, such as plant stress hormones, by priming and exogenously, as a way of increase the phytochemical profile of these sprouts to enhance their consumption in the diet. PMID:26988507

  11. Effect of zinc and glucosinolates on nutritional quality of Noccaea caerulescens and infestation by Aleyrodes proletella.

    PubMed

    Asad, Saeed Ahmad; Young, Scott D; West, Helen M

    2015-04-01

    The Zn hyperaccumulating plant, Noccaea caerulescens, was grown under controlled conditions at a range of Zn concentrations (0-1000 mg kg(-1) dwt. soil) to determine the effectiveness of hyperaccumulation in deterring the cabbage whitefly, Aleyrodes proletella, and to establish the relationship between levels of foliar Zn and glucosinolates (organic defence compounds). Two weeks after introducing A. proletella adults to the plants, next generation nymphs were quantified. This sucking insect caused minimal damage to plant tissue and did not affect foliar glucosinolate levels. Foliar Zn concentrations increased with increasing soil Zn application and reached a maximum of ~7000 mg kg(-1). More whitefly nymphs were observed on plants as the foliar Zn concentration increased (up to ~3000 mg kg(-1)) after which numbers declined. Zn was an explanatory variable in accumulated generalised linear regression after the variation in the data due to C/N ratio had been accounted for. Nymph numbers declined with increasing C/N ratio and increased with increasing N concentration. The highest glucosinolate concentrations were in shoots with the lowest Zn concentrations; this is consistent with the 'trade-off' hypothesis which states that elemental defence mechanisms allow for lowered organic defences. PMID:25525711

  12. Influence of cabbage processing methods and prebiotic manipulation of colonic microflora on glucosinolate breakdown in man.

    PubMed

    Fuller, Zoë; Louis, Petra; Mihajlovski, Agnès; Rungapamestry, Vanessa; Ratcliffe, Brian; Duncan, Alan J

    2007-08-01

    Glucosinolate consumption from brassica vegetables has been implicated in reduction of cancer risk. The isothiocyanate breakdown products of glucosinolates appear to be particularly important as chemoprotective agents. Before consumption, brassica vegetables are generally cooked, causing the plant enzyme, myrosinase, to be denatured, influencing the profile of glucosinolate breakdown products produced. Some human intestinal microflora species show myrosinase-like activity (e.g. bifidobacteria). We aimed to increase bifidobacteria by offering a prebiotic (inulin) in a randomised crossover study. Six volunteers consumed inulin (10 g/d) for 21 d followed by a 21 d control period (no inulin). Treatment periods were reversed for the remaining six volunteers. During the last 5 d of each period two cabbage-containing meals were consumed. Total urine output was collected for 24 h following each meal. Cabbage was microwaved for 2 min (lightly cooked) or 5.5 min (fully cooked). Faecal samples were collected at the start and after the inulin and control treatments. Bifidobacteria were enumerated by real-time PCR. Allyl isothiocyanate production was quantified by measuring urinary excretion of allyl mercapturic acid (AMA). Bifidobacteria increased following prebiotic supplementation (P < 0.001) but there was no impact of this increase on AMA excretion. AMA excretion was greater following consumption of lightly cooked cabbage irrespective of prebiotic treatment (P < 0.001). In conclusion, the most effective way to increase isothiocyanate production may be to limit the length of time that brassica vegetables are cooked prior to consumption. PMID:17403273

  13. Influence of fermentation on glucosinolates and glucobrassicin degradation products in sauerkraut.

    PubMed

    Palani, Kalpana; Harbaum-Piayda, Britta; Meske, Diana; Keppler, Julia Katharina; Bockelmann, Wilhelm; Heller, Knut J; Schwarz, Karin

    2016-01-01

    A systematic investigation was carried out on the influence of fermentation on glucosinolates and their degradation products from fresh raw cabbage, throughout fermentation at 20 °C and storage at 4 °C. Glucosinolates were degraded dramatically between Day 2 and 5 of fermentation and by Day 7 there was no detectable amount of glucosinolates left. Fermentation led to formation of potential bioactive compounds ascorbigen (13.0 μmol/100 g FW) and indole-3-carbinol (4.52 μmol/100g FW) with their higher concentrations from Day 5 to Day 9. However, during storage indole-3-carbinol slowly degraded to 0.68 μmol/100 g FW, while ascorbigen was relatively stable from Week 4 until Week 8 at 6.78 μmol/100 g FW. In contrast, the content of indole-3-acetonitrile decreased rapidly during fermentation from 3.6 to 0.14 μmol/100 g FW. The results imply a maximum of health beneficial compounds after fermentation (7-9 days) in contrast to raw cabbage or stored sauerkraut. PMID:26213035

  14. Changes in the glucosinolate-myrosinase defense system in Brassica juncea cotyledons during seedling development.

    PubMed

    Wallace, S K; Eigenbrode, Sanford D

    2002-02-01

    Optimal defense theory (ODT) predicts that plant defenses will be allocated to plant organs and tissues in proportion to their relative fitness values and susceptibilities to attack. This study was designed to test ODT predictions on the myrosinase-glucosinolate defense system in Brassica juncea by examining the relationships between the fitness value of B. juncea cotyledons and the levels and effectiveness of cotyledon defenses. Specifically, we estimated fitness value of cotyledons during plant development by measuring plant growth and seed production after cotyledon damage or removal at successive seedling ages. Cotyledon removal within five days of emergence had a significant impact on growth and seed production, but cotyledon removal at later stages did not. Consistent with ODT, glucosinolate and myrosinase levels in cotyledons also declined with seedling age, as did relative defenses against a generalist herbivore, Spodoptera eridania, as estimated by bioassay. Declines in glucosinolates were as predicted by a passive, allometric dilution model based on cotyledon expansion. Declines in myrosinase activity were significantly more gradual than predicted by allometric dilution, suggesting active retention of myrosinase activity as young cotyledons expand. PMID:11925065

  15. Regulatory Network of Secondary Metabolism in Brassica rapa: Insight into the Glucosinolate Pathway

    PubMed Central

    Pino Del Carpio, Dunia; Basnet, Ram Kumar; Arends, Danny; Lin, Ke; De Vos, Ric C. H.; Muth, Dorota; Kodde, Jan; Boutilier, Kim; Bucher, Johan; Wang, Xiaowu; Jansen, Ritsert; Bonnema, Guusje

    2014-01-01

    Brassica rapa studies towards metabolic variation have largely been focused on the profiling of the diversity of metabolic compounds in specific crop types or regional varieties, but none aimed to identify genes with regulatory function in metabolite composition. Here we followed a genetical genomics approach to identify regulatory genes for six biosynthetic pathways of health-related phytochemicals, i.e carotenoids, tocopherols, folates, glucosinolates, flavonoids and phenylpropanoids. Leaves from six weeks-old plants of a Brassica rapa doubled haploid population, consisting of 92 genotypes, were profiled for their secondary metabolite composition, using both targeted and LC-MS-based untargeted metabolomics approaches. Furthermore, the same population was profiled for transcript variation using a microarray containing EST sequences mainly derived from three Brassica species: B. napus, B. rapa and B. oleracea. The biochemical pathway analysis was based on the network analyses of both metabolite QTLs (mQTLs) and transcript QTLs (eQTLs). Co-localization of mQTLs and eQTLs lead to the identification of candidate regulatory genes involved in the biosynthesis of carotenoids, tocopherols and glucosinolates. We subsequently focused on the well-characterized glucosinolate pathway and revealed two hotspots of co-localization of eQTLs with mQTLs in linkage groups A03 and A09. Our results indicate that such a large-scale genetical genomics approach combining transcriptomics and metabolomics data can provide new insights into the genetic regulation of metabolite composition of Brassica vegetables. PMID:25222144

  16. Identification of Candidate Genes for Seed Glucosinolate Content Using Association Mapping in Brassica napus L.

    PubMed

    Qu, Cun-Min; Li, Shi-Meng; Duan, Xiu-Jian; Fan, Jin-Hua; Jia, Le-Dong; Zhao, Hui-Yan; Lu, Kun; Li, Jia-Na; Xu, Xin-Fu; Wang, Rui

    2015-01-01

    Rapeseed contains glucosinolates, a toxic group of sulfur-containing glucosides, which play critical roles in defense against herbivores and microbes. However, the presence of glucosinolates in rapeseed reduces the value of the meal as feed for livestock. We performed association mapping of seed glucosinolate (GS) content using the 60K Brassica Infinium single nucleotide polymorphism (SNP) array in 520 oilseed rape accessions. A total of 11 peak SNPs significantly associated with GS content were detected in growing seasons of 2013 and 2014 and were located on B. napus chromosomes A08, A09, C03, and C09, respectively. Two associated regions of GS content covered by these markers were further verified, and three B. napus homologous genes involved in the biosynthesis and accumulation of GS were identified. These genes were multigene family members and were distributed on different chromosomes. Moreover, two genes (BnGRT2 and BnMYB28) associated with GS content were validated by the qRT-PCR analysis of their expression profiles. The further identification and functionalization of these genes will provide useful insight into the mechanism underlying GS biosynthesis and allocation in B. napus, and the associated SNPs markers could be helpful for molecular maker-assisted breeding for low seed GS in B. napus. PMID:26593950

  17. Transcriptional responses of Arabidopsis thaliana ecotypes with different glucosinolate profiles after attack by polyphagous Myzus persicae and oligophagous Brevicoryne brassicae.

    PubMed

    Kusnierczyk, Anna; Winge, Per; Midelfart, Herman; Armbruster, W Scott; Rossiter, John T; Bones, Atle Magnar

    2007-01-01

    Plants are equipped with a range of defence mechanisms against herbivorous insects. In cruciferous species, jasmonic acid, salicylic acid, and ethylene along with glucosinolates and their hydrolysis products play important roles in plant protection and plant-insect communication. In turn, a number of herbivores have adapted to plants that contain glucosinolates. As a result of adaptation to their host plants, specialized insects may elicit different plant-inducible responses than generalists. Oligonucleotide microarrays and qRT-PCR analysis were used to characterize transcriptional profiles of Arabidopsis thaliana plants in response to infestation with a generalist aphid, Myzus persicae, or a cruciferous plant specialist, Brevicoryne brassicae. To find possible differences and similarities in molecular responses between plants differing in predominant glucosinolate hydrolysis products, three ecotypes of A. thaliana were chosen: Wassilewskija (Ws), Cape Verde Islands (Cvi), and Landsberg erecta (Ler), which, respectively, produce mainly isothiocyanates, epithionitriles, and nitriles. In all three ecotypes, general stress-responsive genes, genes belonging to octadecanoid and indole glucosinolate synthesis pathways were induced upon both generalist and specialist attack. By contrast, transcription of myrosinases, enzymes hydrolysing glucosinolates, was suppressed. The induction of the jasmonic acid synthesis pathway was strongest in Cvi, while the up-regulation of the indole glucosinolate synthesis pathway was highest in Ler, suggesting a slightly different defence strategy in these two ecotypes. Specialist and generalist infestations caused statistically significant differential regulation of 60 genes in Ws and 21 in Cvi. Among these were jasmonic acid and tryptophan synthesis pathway enzymes, and pathogenesis related protein (PR1). Insect no-choice experiments revealed lowered fitness of B. brassicae on Ler and Cvi in comparison to Ws, but no ecotype

  18. Leaf and root glucosinolate profiles of Chinese cabbage (Brassica rapa ssp. pekinensis) as a systemic response to methyl jasmonate and salicylic acid elicitation.

    PubMed

    Zang, Yun-xiang; Ge, Jia-li; Huang, Ling-hui; Gao, Fei; Lv, Xi-shan; Zheng, Wei-wei; Hong, Seung-beom; Zhu, Zhu-jun

    2015-08-01

    Glucosinolates (GSs) are an important group of defensive phytochemicals mainly found in Brassicaceae. Plant hormones jasmonic acid (JA) and salicylic acid (SA) are major regulators of plant response to pathogen attack. However, there is little information about the interactive effect of both elicitors on inducing GS biosynthesis in Chinese cabbage (Brassica rapa ssp. pekinensis). In this study, we applied different concentrations of methyl jasmonate (MeJA) and/or SA onto the leaf and root of Chinese cabbage to investigate the time-course interactive profiles of GSs. Regardless of the site of the elicitation and the concentrations of the elicitors, the roots accumulated much more GSs and were more sensitive and more rapidly responsive to the elicitors than leaves. Irrespective of the elicitation site, MeJA had a greater inducing and longer lasting effect on GS accumulation than SA. All three components of indole GS (IGS) were detected along with aliphatic and aromatic GSs. However, IGS was a major component of total GSs that accumulated rapidly in both root and leaf tissues in response to MeJA and SA elicitation. Neoglucobrassicin (neoGBC) did not respond to SA but to MeJA in leaf tissue, while it responded to both SA and MeJA in root tissue. Conversion of glucobrassicin (GBC) to neoGBC occurred at a steady rate over 3 d of elicitation. Increased accumulation of 4-methoxy glucobrassicin (4-MGBC) occurred only in the root irrespective of the type of elicitors and the site of elicitation. Thus, accumulation of IGS is a major metabolic hallmark of SA- and MeJA-mediated systemic response systems. SA exerted an antagonistic effect on the MeJA-induced root GSs irrespective of the site of elicitation. However, SA showed synergistic and antagonistic effects on the MeJA-induced leaf GSs when roots and leaves are elicitated for 3 d, respectively. PMID:26238545

  19. Leaf and root glucosinolate profiles of Chinese cabbage (Brassica rapa ssp. pekinensis) as a systemic response to methyl jasmonate and salicylic acid elicitation*

    PubMed Central

    Zang, Yun-xiang; Ge, Jia-li; Huang, Ling-hui; Gao, Fei; Lv, Xi-shan; Zheng, Wei-wei; Hong, Seung-beom; Zhu, Zhu-jun

    2015-01-01

    Glucosinolates (GSs) are an important group of defensive phytochemicals mainly found in Brassicaceae. Plant hormones jasmonic acid (JA) and salicylic acid (SA) are major regulators of plant response to pathogen attack. However, there is little information about the interactive effect of both elicitors on inducing GS biosynthesis in Chinese cabbage (Brassica rapa ssp. pekinensis). In this study, we applied different concentrations of methyl jasmonate (MeJA) and/or SA onto the leaf and root of Chinese cabbage to investigate the time-course interactive profiles of GSs. Regardless of the site of the elicitation and the concentrations of the elicitors, the roots accumulated much more GSs and were more sensitive and more rapidly responsive to the elicitors than leaves. Irrespective of the elicitation site, MeJA had a greater inducing and longer lasting effect on GS accumulation than SA. All three components of indole GS (IGS) were detected along with aliphatic and aromatic GSs. However, IGS was a major component of total GSs that accumulated rapidly in both root and leaf tissues in response to MeJA and SA elicitation. Neoglucobrassicin (neoGBC) did not respond to SA but to MeJA in leaf tissue, while it responded to both SA and MeJA in root tissue. Conversion of glucobrassicin (GBC) to neoGBC occurred at a steady rate over 3 d of elicitation. Increased accumulation of 4-methoxy glucobrassicin (4-MGBC) occurred only in the root irrespective of the type of elicitors and the site of elicitation. Thus, accumulation of IGS is a major metabolic hallmark of SA- and MeJA-mediated systemic response systems. SA exerted an antagonistic effect on the MeJA-induced root GSs irrespective of the site of elicitation. However, SA showed synergistic and antagonistic effects on the MeJA-induced leaf GSs when roots and leaves are elicitated for 3 d, respectively. PMID:26238545

  20. Structure of pyrrhotite 5C (Fe9S10).

    PubMed

    Elliot, Alexander Dean

    2010-06-01

    The distribution of vacancies throughout the underlying NiAs structure of pyrrhotite 5C was analysed through the application of vacancy avoidance and the closeness condition in conjunction with order-disorder layering. Two crystallographically equivalent structure solutions (chiral enantiomers) were produced consisting of layers containing one vacancy in every eight iron sites broken by a fully occupied layer every fifth iron layer, and best described by monoclinic statistical models. The statistical 5C structures were verified using synchrotron powder diffraction data as well as published electron-diffraction patterns. An order-disorder structure description is proposed for the intermediate pyrrhotites of which pyrrhotite 5C is an end-member. PMID:20484798

  1. Flavor, glucosinolates, and isothiocyanates of nau (Cook's scurvy grass, Lepidium oleraceum) and other rare New Zealand Lepidium species.

    PubMed

    Sansom, Catherine E; Jones, Veronika S; Joyce, Nigel I; Smallfield, Bruce M; Perry, Nigel B; van Klink, John W

    2015-02-18

    The traditionally consumed New Zealand native plant nau, Cook's scurvy grass, Lepidium oleraceum, has a pungent wasabi-like taste, with potential for development as a flavor ingredient. The main glucosinolate in this Brassicaceae was identified by LC-MS and NMR spectroscopy as 3-butenyl glucosinolate (gluconapin, 7-22 mg/g DM in leaves). The leaves were treated to mimic chewing, and the headspace was analyzed by solid-phase microextraction and GC-MS. This showed that 3-butenyl isothiocyanate, with a wasabi-like flavor, was produced by the endogenous myrosinase. Different postharvest treatments were used to create leaf powders as potential flavor products, which were tasted and analyzed for gluconapin and release of 3-butenyl isothiocyanate. A high drying temperature (75 °C) did not give major glucosinolate degradation, but did largely inactivate the myrosinase, resulting in no wasabi-like flavor release. Drying at 45 °C produced more pungent flavor than freeze-drying. Seven other Lepidium species endemic to New Zealand were also analyzed to determine their flavor potential and also whether glucosinolates were taxonomic markers. Six contained mostly gluconapin, but the critically endangered Lepidium banksii had a distinct composition including isopropyl glucosinolate, not detected in the other species. PMID:25625566

  2. Variation and fitness costs for tolerance to different types of herbivore damage in Boechera stricta genotypes with contrasting glucosinolate structures

    PubMed Central

    Manzaneda, Antonio J.; Prasad, Kasavajhala V. S. K.; Mitchell-Olds, Thomas

    2010-01-01

    Summary Analyses of plant tolerance in response to different modes of herbivory are essential to understand plant defense evolution, yet are still scarce. Allocation costs and trade-offs between tolerance and plant chemical defenses may influence genetic variation for tolerance. However, variation in defenses occurs also for presence or absence of discrete chemical structures, yet, effects of intra-specific polymorphisms on tolerance to multiple herbivores have not been evaluated.Here, in a glasshouse experiment, we investigated variation for tolerance to different types of herbivory damage, and direct allocation costs in 10 genotypes of Boechera stricta (Brassicaceae), a wild relative of Arabidopsis, with contrasting foliar glucosinolate chemical structures (methionine-derived glucosinolates vs glucosinolates derived from branched-chain amino acids).We found significant genetic variation for tolerance to different types of herbivory. Structural variations in the glucosinolate profile did not influence tolerance to damage, but predicted plant fitness. Levels of constitutive and induced glucosinolates varied between genotypes with different structural profiles, but we did not detect any cost of tolerance explaining genetic variation in tolerance among genotypes.Trade-offs among plant tolerance to multiple herbivores may not explain the existence of intermediate levels of tolerance to damage in plants with contrasting chemical defensive profiles. PMID:20663059

  3. Insect Attraction versus Plant Defense: Young Leaves High in Glucosinolates Stimulate Oviposition by a Specialist Herbivore despite Poor Larval Survival due to High Saponin Content

    PubMed Central

    Badenes-Perez, Francisco R.; Gershenzon, Jonathan; Heckel, David G.

    2014-01-01

    Glucosinolates are plant secondary metabolites used in plant defense. For insects specialized on Brassicaceae, such as the diamondback moth, Plutella xylostella L. (Lepidoptera: Plutellidae), glucosinolates act as “fingerprints” that are essential in host plant recognition. Some plants in the genus Barbarea (Brassicaceae) contain, besides glucosinolates, saponins that act as feeding deterrents for P. xylostella larvae, preventing their survival on the plant. Two-choice oviposition tests were conducted to study the preference of P. xylostella among Barbarea leaves of different size within the same plant. P. xylostella laid more eggs per leaf area on younger leaves compared to older ones. Higher concentrations of glucosinolates and saponins were found in younger leaves than in older ones. In 4-week-old plants, saponins were present in true leaves, while cotyledons contained little or no saponins. When analyzing the whole foliage of the plant, the content of glucosinolates and saponins also varied significantly in comparisons among plants that were 4, 8, and 12 weeks old. In Barbarea plants and leaves of different ages, there was a positive correlation between glucosinolate and saponin levels. This research shows that, in Barbarea plants, ontogenetical changes in glucosinolate and saponin content affect both attraction and resistance to P. xylostella. Co-occurrence of a high content of glucosinolates and saponins in the Barbarea leaves that are most valuable for the plant, but are also the most attractive to P. xylostella, provides protection against this specialist herbivore, which oviposition behavior on Barbarea seems to be an evolutionary mistake. PMID:24752069

  4. Diversified glucosinolate metabolism: biosynthesis of hydrogen cyanide and of the hydroxynitrile glucoside alliarinoside in relation to sinigrin metabolism in Alliaria petiolata

    PubMed Central

    Frisch, Tina; Motawia, Mohammed S.; Olsen, Carl E.; Agerbirk, Niels; Møller, Birger L.; Bjarnholt, Nanna

    2015-01-01

    Alliaria petiolata (garlic mustard, Brassicaceae) contains the glucosinolate sinigrin as well as alliarinoside, a γ-hydroxynitrile glucoside structurally related to cyanogenic glucosides. Sinigrin may defend this plant against a broad range of enemies, while alliarinoside confers resistance to specialized (glucosinolate-adapted) herbivores. Hydroxynitrile glucosides and glucosinolates are two classes of specialized metabolites, which generally do not occur in the same plant species. Administration of [UL-14C]-methionine to excised leaves of A. petiolata showed that both alliarinoside and sinigrin were biosynthesized from methionine. The biosynthesis of alliarinoside was shown not to bifurcate from sinigrin biosynthesis at the oxime level in contrast to the general scheme for hydroxynitrile glucoside biosynthesis. Instead, the aglucon of alliarinoside was formed from metabolism of sinigrin in experiments with crude extracts, suggesting a possible biosynthetic pathway in intact cells. Hence, the alliarinoside pathway may represent a route to hydroxynitrile glucoside biosynthesis resulting from convergent evolution. Metabolite profiling by LC-MS showed no evidence of the presence of cyanogenic glucosides in A. petiolata. However, we detected hydrogen cyanide (HCN) release from sinigrin and added thiocyanate ion and benzyl thiocyanate in A. petiolata indicating an enzymatic pathway from glucosinolates via allyl thiocyanate and indole glucosinolate derived thiocyanate ion to HCN. Alliarinoside biosynthesis and HCN release from glucosinolate-derived metabolites expand the range of glucosinolate-related defenses and can be viewed as a third line of defense, with glucosinolates and thiocyanate forming protein being the first and second lines, respectively. PMID:26583022

  5. Foreign Language Professional Standards and CSL: Achieving the 5 C's

    ERIC Educational Resources Information Center

    Lear, Darcy W.; Abbott, Annie R.

    2008-01-01

    The professional standards in the field of foreign language pedagogy focus on communication, cultures, connections, comparisons, and communities. Using those 5 C's as a framework, the authors examine student success at satisfying those disciplinary standards through community service learning (CSL). Data is used to present a qualitative case…

  6. Investigation of the multifunctional gene AOP3 expands the regulatory network fine-tuning glucosinolate production in Arabidopsis

    PubMed Central

    Jensen, Lea M.; Kliebenstein, Daniel J.; Burow, Meike

    2015-01-01

    Quantitative trait loci (QTL) mapping studies enable identification of loci that are part of regulatory networks controlling various phenotypes. Detailed investigations of genes within these loci are required to ultimately understand the function of individual genes and how they interact with other players in the network. In this study, we use transgenic plants in combination with natural variation to investigate the regulatory role of the AOP3 gene found in GS-AOP locus previously suggested to contribute to the regulation of glucosinolate defense compounds. Phenotypic analysis and QTL mapping in F2 populations with different AOP3 transgenes support that the enzymatic function and the AOP3 RNA both play a significant role in controlling glucosinolate accumulation. Furthermore, we find different loci interacting with either the enzymatic activity or the RNA of AOP3 and thereby extend the regulatory network controlling glucosinolate accumulation. PMID:26442075

  7. Effects of industrial pre-freezing processing and freezing handling on glucosinolates and antioxidant attributes in broccoli florets.

    PubMed

    Cai, Congxi; Miao, Huiying; Qian, Hongmei; Yao, Leishuan; Wang, Bingliang; Wang, Qiaomei

    2016-11-01

    The effects of industrial pre-freezing processing and freezing handling on the contents of glucosinolates and antioxidants (vitamin C, polyphenols, carotenoid and chlorophyll), as well as the antioxidant capacity in broccoli (Brassica oleracea L. var. italica) florets were investigated in the present study. Our results showed that the glucosinolate accumulations were significantly decreased after pre-freezing processing, whereas elevated levels of phenols, carotenoids, chlorophyll, and also antioxidant capacity were observed in frozen broccoli florets. The contents of vitamin C remained constant during above mentioned processing. In conclusion, the current industrial freezing processing method is a good practice for the preservation of main antioxidant nutrients in broccoli florets, although some improvements in pre-freezing processing, such as steam blanching and ice-water cooling, are needed to attenuate the decrease in glucosinolate content. PMID:27211670

  8. Catalytic Asymmetric Hydroamination of Unactivated Internal Olefins to Aliphatic Amines

    PubMed Central

    Yang, Yang; Shi, Shi-Liang; Niu, Dawen; Liu, Peng; Buchwald, Stephen L.

    2015-01-01

    Catalytic assembly of enantiopure aliphatic amines from abundant and readily available precursors has long been recognized as a paramount challenge in synthetic chemistry. Herein, we describe a mild and general copper-catalyzed hydroamination that effectively converts unactivated internal olefins, an important yet unexploited class of abundant feedstock chemicals, into highly enantioenriched α-branched amines (≥ 96% enantiomeric excess) featuring two minimally differentiated aliphatic substituents. This method provides a powerful means to access a broad range of advanced, highly functionalized enantioenriched amines of interest in pharmaceutical research and other areas. PMID:26138973

  9. Enhancement of broccoli indole glucosinolates by methyl jasmonate treatment and effects on prostate carcinogenesis.

    PubMed

    Liu, Ann G; Juvik, John A; Jeffery, Elizabeth H; Berman-Booty, Lisa D; Clinton, Steven K; Erdman, John W

    2014-11-01

    Broccoli is rich in bioactive components, such as sulforaphane and indole-3-carbinol, which may impact cancer risk. The glucosinolate profile of broccoli can be manipulated through treatment with the plant stress hormone methyl jasmonate (MeJA). Our objective was to produce broccoli with enhanced levels of indole glucosinolates and determine its impact on prostate carcinogenesis. Brassica oleracea var. Green Magic was treated with a 250 μM MeJA solution 4 days prior to harvest. MeJA-treated broccoli had significantly increased levels of glucobrassicin, neoglucobrassicin, and gluconasturtiin (P < .05). Male transgenic adenocarcinoma of mouse prostate (TRAMP) mice (n = 99) were randomized into three diet groups at 5-7 weeks of age: AIN-93G control, 10% standard broccoli powder, or 10% MeJA broccoli powder. Diets were fed throughout the study until termination at 20 weeks of age. Hepatic CYP1A was induced with MeJA broccoli powder feeding, indicating biological activity of the indole glucosinolates. Following ∼ 15 weeks on diets, neither of the broccoli treatments significantly altered genitourinary tract weight, pathologic score, or metastasis incidence, indicating that broccoli powder at 10% of the diet was ineffective at reducing prostate carcinogenesis in the TRAMP model. Whereas broccoli powder feeding had no effect in this model of prostate cancer, our work demonstrates the feasibility of employing plant stress hormones exogenously to stimulate changes in phytochemical profiles, an approach that may be useful for optimizing bioactive component patterns in foods for chronic-disease-prevention studies. PMID:24983303

  10. The selective cytotoxicity of the alkenyl glucosinolate hydrolysis products and their presence in Brassica vegetables.

    PubMed

    Kadir, Nurul H A; David, Rhiannon; Rossiter, John T; Gooderham, Nigel J

    2015-08-01

    Cruciferous vegetable consumption correlates with reduced risk of cancer. This chemopreventative activity may involve glucosinolates and their hydrolysis products. Glucosinolate-derived isothiocyanates have been studied for their toxicity and chemopreventative properties, but other hydrolysis products (epithionitriles and nitriles) have not been thoroughly examined. We report that these hydrolysis products differ in their cytotoxicity to human cells, with toxicity most strongly associated with isothiocyanates rather than epithionitriles and nitriles. We explored mechanisms of this differential cytotoxicity by examining the role of oxidative metabolism, oxidative stress, mitochondrial permeability, reduced glutathione levels, cell cycle arrest and apoptosis. 2-Propenylisothiocyanate and 3-butenylisothiocyanate both inhibited cytochome P450 1A (CYP1A) enzyme activity in CYP expressing MCL-5 cells at high cytotoxic doses. Incubation of MCL-5 cells with non-cytotoxic doses of 2-propenylisothiocyanate for 24h resulted in a dose-dependent inhibition of ethoxyresorufin O-deethylase, yet failed to affect CYP1A1 mRNA expression indicating interference with enzyme activity rather than inhibition of transcription. Increased reactive oxygen species (ROS) production was observed only for 2-propenylisothiocyanate treatment. 2-Propenylisothiocyanate treatment lowered reduced glutathione levels whereas no changes were noted with 3,4-epithiobutylnitrile. Cell cycle analysis showed that 2-propenylisothiocyanate induced a G2/M block whereas other hydrolysis products showed only marginal effects. We found that 2-propenylisothiocyanate and 3-butenylisothiocyanate induced cell death predominantly via necrosis whereas, 3,4-epithiobutylnitrile promoted both necrosis and apoptosis. Thus the activity of glucosinolate hydrolysis products includes cytotoxicity that is compound-class specific and may contribute to their putative chemoprotection properties. PMID:26066520

  11. Applicability of the theory of thermodynamic similarity to predict the enthalpies of vaporization of aliphatic aldehydes

    NASA Astrophysics Data System (ADS)

    Esina, Z. N.; Korchuganova, M. R.

    2015-06-01

    The theory of thermodynamic similarity is used to predict the enthalpies of vaporization of aliphatic aldehydes. The predicted data allow us to calculate the phase diagrams of liquid-vapor equilibrium in a binary water-aliphatic aldehyde system.

  12. Introducing Aliphatic Substitution with a Discovery Experiment Using Competing Electrophiles

    ERIC Educational Resources Information Center

    Curran, Timothy P.; Mostovoy, Amelia J.; Curran, Margaret E.; Berger, Clara

    2016-01-01

    A facile, discovery-based experiment is described that introduces aliphatic substitution in an introductory undergraduate organic chemistry curriculum. Unlike other discovery-based experiments that examine substitution using two competing nucleophiles with a single electrophile, this experiment compares two isomeric, competing electrophiles…

  13. Selective stabilization of aliphatic organic carbon by iron oxide

    PubMed Central

    Adhikari, Dinesh; Yang, Yu

    2015-01-01

    Stabilization of organic matter in soil is important for natural ecosystem to sequestrate carbon and mitigate greenhouse gas emission. It is largely unknown what factors govern the preservation of organic carbon in soil, casting shadow on predicting the response of soil to climate change. Iron oxide was suggested as an important mineral preserving soil organic carbon. However, ferric minerals are subject to reduction, potentially releasing iron and decreasing the stability of iron-bound organic carbon. Information about the stability of iron-bound organic carbon in the redox reaction is limited. Herein, we investigated the sorptive interactions of organic matter with hematite and reductive release of hematite-bound organic matter. Impacts of organic matter composition and conformation on its sorption by hematite and release during the reduction reaction were analyzed. We found that hematite-bound aliphatic carbon was more resistant to reduction release, although hematite preferred to sorb more aromatic carbon. Resistance to reductive release represents a new mechanism that aliphatic soil organic matter was stabilized by association with iron oxide. Selective stabilization of aliphatic over aromatic carbon can greatly contribute to the widely observed accumulation of aliphatic carbon in soil, which cannot be explained by sorptive interactions between minerals and organic matter. PMID:26061259

  14. Triphosgene–Amine Base Promoted Chlorination of Unactivated Aliphatic Alcohols

    PubMed Central

    Villalpando, Andrés; Ayala, Caitlan E.; Watson, Christopher B.; Kartika, Rendy

    2014-01-01

    Unactivated α-branched primary and secondary aliphatic alcohols have been successfully transformed into their corresponding alkyl chlorides in high yields upon treatment with a mixture of triphosgene and pyridine in dichloromethane at reflux. These mild chlorination conditions are high yielding, stereospecific, and well tolerated by numerous sensitive functionalities. Furthermore, no nuisance waste products are generated in the course of the reactions. PMID:23496045

  15. Cloud condensation nuclei activity of aliphatic amine secondary aerosol

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Aliphatic amines can form secondary aerosol via oxidation with atmospheric radicals (e.g. hydroxyl radical and nitrate radical). The resulting particle composition can contain both secondary organic aerosol (SOA) and inorganic salts. The fraction of organic to inorganic materials in the particulate ...

  16. A thermostable transketolase evolved for aliphatic aldehyde acceptors.

    PubMed

    Yi, Dong; Saravanan, Thangavelu; Devamani, Titu; Charmantray, Franck; Hecquet, Laurence; Fessner, Wolf-Dieter

    2015-01-11

    Directed evolution of the thermostable transketolase from Geobacillus stearothermophilus based on a pH-based colorimetric screening of smart libraries yielded several mutants with up to 16-fold higher activity for aliphatic aldehydes and high enantioselectivity (>95% ee) in the asymmetric carboligation step. PMID:25415647

  17. 40 CFR 721.10199 - Substituted aliphatic amine (generic).

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... should be tested and approved for the gas/vapor substance (i.e., organic vapor, acid gas, or substance... combination cartridges, cartridges should be tested and approved for the gas/vapor substance (i.e., organic... Specific Chemical Substances § 721.10199 Substituted aliphatic amine (generic). (a) Chemical substance...

  18. 40 CFR 721.10199 - Substituted aliphatic amine (generic).

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... should be tested and approved for the gas/vapor substance (i.e., organic vapor, acid gas, or substance... combination cartridges, cartridges should be tested and approved for the gas/vapor substance (i.e., organic... Specific Chemical Substances § 721.10199 Substituted aliphatic amine (generic). (a) Chemical substance...

  19. 40 CFR 721.10199 - Substituted aliphatic amine (generic).

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... should be tested and approved for the gas/vapor substance (i.e., organic vapor, acid gas, or substance... combination cartridges, cartridges should be tested and approved for the gas/vapor substance (i.e., organic... Specific Chemical Substances § 721.10199 Substituted aliphatic amine (generic). (a) Chemical substance...

  20. 40 CFR 721.10199 - Substituted aliphatic amine (generic).

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... should be tested and approved for the gas/vapor substance (i.e., organic vapor, acid gas, or substance... combination cartridges, cartridges should be tested and approved for the gas/vapor substance (i.e., organic... Specific Chemical Substances § 721.10199 Substituted aliphatic amine (generic). (a) Chemical substance...

  1. 40 CFR 721.10608 - Aliphatic diisocyanate polymer with alkanediol and alkylglycol (generic).

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Aliphatic diisocyanate polymer with... Significant New Uses for Specific Chemical Substances § 721.10608 Aliphatic diisocyanate polymer with.... (1) The chemical substance identified generically as aliphatic diisocyanate polymer with...

  2. 40 CFR 721.10608 - Aliphatic diisocyanate polymer with alkanediol and alkylglycol (generic).

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Aliphatic diisocyanate polymer with... Significant New Uses for Specific Chemical Substances § 721.10608 Aliphatic diisocyanate polymer with.... (1) The chemical substance identified generically as aliphatic diisocyanate polymer with...

  3. 40 CFR 721.10289 - Hexanedioic acid polymer with aliphatic polyol dihydrogen phosphate aromatic ester (generic).

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... aliphatic polyol dihydrogen phosphate aromatic ester (generic). 721.10289 Section 721.10289 Protection of... polymer with aliphatic polyol dihydrogen phosphate aromatic ester (generic). (a) Chemical substance and... acid polymer with aliphatic polyol dihydrogen phosphate aromatic ester (PMN P-11-333) is subject...

  4. 40 CFR 721.10289 - Hexanedioic acid polymer with aliphatic polyol dihydrogen phosphate aromatic ester (generic).

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... aliphatic polyol dihydrogen phosphate aromatic ester (generic). 721.10289 Section 721.10289 Protection of... polymer with aliphatic polyol dihydrogen phosphate aromatic ester (generic). (a) Chemical substance and... acid polymer with aliphatic polyol dihydrogen phosphate aromatic ester (PMN P-11-333) is subject...

  5. 40 CFR 721.10289 - Hexanedioic acid polymer with aliphatic polyol dihydrogen phosphate aromatic ester (generic).

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... aliphatic polyol dihydrogen phosphate aromatic ester (generic). 721.10289 Section 721.10289 Protection of... polymer with aliphatic polyol dihydrogen phosphate aromatic ester (generic). (a) Chemical substance and... acid polymer with aliphatic polyol dihydrogen phosphate aromatic ester (PMN P-11-333) is subject...

  6. In vitro activity of glucosinolates and their degradation products against brassica-pathogenic bacteria and fungi.

    PubMed

    Sotelo, T; Lema, M; Soengas, P; Cartea, M E; Velasco, P

    2015-01-01

    Glucosinolates (GSLs) are secondary metabolites found in Brassica vegetables that confer on them resistance against pests and diseases. Both GSLs and glucosinolate hydrolysis products (GHPs) have shown positive effects in reducing soil pathogens. Information about their in vitro biocide effects is scarce, but previous studies have shown sinigrin GSLs and their associated allyl isothiocyanate (AITC) to be soil biocides. The objective of this work was to evaluate the biocide effects of 17 GSLs and GHPs and of leaf methanolic extracts of different GSL-enriched Brassica crops on suppressing in vitro growth of two bacterial (Xanthomonas campestris pv. campestris and Pseudomonas syringae pv. maculicola) and two fungal (Alternaria brassicae and Sclerotinia scletoriorum) Brassica pathogens. GSLs, GHPs, and methanolic leaf extracts inhibited the development of the pathogens tested compared to the control, and the effect was dose dependent. Furthermore, the biocide effects of the different compounds studied were dependent on the species and race of the pathogen. These results indicate that GSLs and their GHPs, as well as extracts of different Brassica species, have potential to inhibit pathogen growth and offer new opportunities to study the use of Brassica crops in biofumigation for the control of multiple diseases. PMID:25362058

  7. Isolation of a Microsomal Enzyme System Involved in Glucosinolate Biosynthesis from Seedlings of Tropaeolum majus L.

    PubMed Central

    Du, L.; Halkier, B. A.

    1996-01-01

    An in vitro system that converts phenylalanine to phenylacetaldoxime in the biosynthesis of the glucosinolate glucotropaeolin has been established in seedlings of Tropaeolum majus L. exposed to the combined treatment of jasmonic acid, ethanol, and light. The treatment resulted in a 9-fold induction, compared with untreated, dark-grown seedlings, of de novo biosynthesis measured as incorporation of radioactively labeled phenylalanine into glucotropaeolin. Formation of the inhibitory degradation product benzylisothiocyanate during tissue homogenization was prevented by inactivation of the thioglucosidase myrosinase by addition of 100 mM ascorbic acid to the isolation buffer. This allowed the isolation of a biosynthetically active microsomal preparation from the induced T. majus plant material. The enzyme, which catalyzes the conversion of phenylalanine to the corresponding oxime, was sensitive to cytochrome P450 inhibitors, indicating the involvement of a cytochrome P450 in the biosynthetic pathway. It has previously been shown that the oxime-producing enzyme in the biosynthesis of p-hydroxybenzylglucosinolate in Sinapis alba L. is dependent on cytochrome P450, whereas the oxime-producing enzymes in Brassica species have been suggested to be flavin monooxygenases or peroxidase-type enzymes. The result with T. majus provides additional experimental documentation for a similarity between the enzymes converting amino acids into the corresponding oximes in the biosynthesis of glucosinolates and cyanogenic glucosides. PMID:12226332

  8. Optimized extraction, separation and quantification of twelve intact glucosinolates in broccoli leaves.

    PubMed

    Ares, Ana M; Nozal, María J; Bernal, José L; Bernal, José

    2014-01-01

    A new method has been developed and validated to determine twelve intact glucosinolates (glucoiberin, GIB; glucoraphanin, GRA; glucoerucin GER; gluconapin, GNA; glucotropaeolin, GTL; glucobrassicin, GBC; gluconasturtiin, GST; glucoalyssin, ALY; 4-hydroxyglucobrassicin, 4-OH; 4-metoxyglucobrassicin, 4ME; neoglucobrassicin, NEO; sinigrin, SIN) in broccoli leaves using liquid chromatography (LC) coupled to diode array (DAD) and electrospray ionization mass spectrometry (ESI-MS) detection. An extraction procedure has also been proposed and optimized by means of statistical analysis (the Box-Behnken design and analysis of variance); this is based on the deactivation of myrosinase using a microwave and heated water. Low limits of detection and quantification were obtained, ranging from 10 to 72 μg/g with DAD and 0.01 to 0.23 μg/g with ESI-MS, and the resulting recovery values ranged from 87% to 106% in all cases. Finally, glucosinolates were analyzed in broccoli leaf samples from six different cultivars (Ramoso calabrese Parthenon, Marathon, Nubia, Naxos and Viola). PMID:24444907

  9. Identification and phytotoxicity of a new glucosinolate breakdown product from Meadowfoam (Limnanthes alba) seed meal.

    PubMed

    Intanon, Suphannika; Reed, Ralph L; Stevens, Jan F; Hulting, Andrew G; Mallory-Smith, Carol A

    2014-07-30

    Meadowfoam (Limnanthes alba Hartw. ex Benth.) is an oilseed crop grown in the Willamette Valley of Oregon. Meadowfoam seed meal (MSM), a byproduct after oil extraction, contains 2-4% glucosinolate (glucolimnanthin). Activated MSM, produced by adding freshly ground myrosinase-active meadowfoam seeds to MSM, facilitates myrosinase-mediated formation of glucosinolate-derived degradation products with herbicidal activity. In the activated MSM, glucolimnanthin was converted into 3-methoxybenzyl isothiocyanate ("isothiocyanate") within 24 h and was degraded by day three. 3-Methoxyphenylacetonitrile ("nitrile") persisted for at least 6 days. Methoxyphenylacetic acid (MPAA), a previously unknown metabolite of glucolimnanthin, appeared at day three. Its identity was confirmed by LC-UV and high resolution LC-MS/MS comparisons with a standard of MPAA. Isothiocyanate inhibited lettuce germination 8.5- and 14.4-fold more effectively than MPAA and nitrile, respectively. Activated MSM inhibited lettuce germination by 58% and growth by 72% compared with the control. Results of the study suggest that MSM has potential uses as a pre-emergence bioherbicide. PMID:24998843

  10. Herbicidal Activity of Glucosinolate Degradation Products in Fermented Meadowfoam (Limnanthes alba) Seed Meal

    PubMed Central

    STEVENS, JAN F.; REED, RALPH L.; ALBER, SUSAN; PRITCHETT, LARRY; MACHADO, STEPHEN

    2009-01-01

    Meadowfoam (Limnanthes alba) is an oilseed crop grown in western Oregon. After extraction of the oil from the seeds, the remaining seed meal contains 2-4% of the glucosinolate, glucolimnanthin. We investigated the effect of fermentation of seed meal on its chemical composition and the effect of the altered composition on downy brome (Bromus tectorum) coleoptile emergence. Incubation of enzyme-inactive seed meal with enzyme-active seeds (1% by weight) resulted in complete degradation of glucolimnanthin and formation of 3-methoxybenzyl isothiocyanate in 28% yield. Fermentation in the presence of an aqueous solution of FeSO4 (10 mM) resulted in the formation of 3-methoxyphenylacetonitrile and 2-(3-methoxyphenyl)ethanethioamide, a novel natural product. The formation of the isothiocyanate, the nitrile and the thioamide, as a total, correlated with an increase of herbicidal potency of seed meal (r2 = 0.96). The results of this study open new possibilities for the refinement of glucosinolate-containing seed meals for use as bioherbicides. PMID:19170637

  11. In Vitro Activity of Glucosinolates and Their Degradation Products against Brassica-Pathogenic Bacteria and Fungi

    PubMed Central

    Sotelo, T.; Lema, M.; Soengas, P.; Cartea, M. E.

    2014-01-01

    Glucosinolates (GSLs) are secondary metabolites found in Brassica vegetables that confer on them resistance against pests and diseases. Both GSLs and glucosinolate hydrolysis products (GHPs) have shown positive effects in reducing soil pathogens. Information about their in vitro biocide effects is scarce, but previous studies have shown sinigrin GSLs and their associated allyl isothiocyanate (AITC) to be soil biocides. The objective of this work was to evaluate the biocide effects of 17 GSLs and GHPs and of leaf methanolic extracts of different GSL-enriched Brassica crops on suppressing in vitro growth of two bacterial (Xanthomonas campestris pv. campestris and Pseudomonas syringae pv. maculicola) and two fungal (Alternaria brassicae and Sclerotinia scletoriorum) Brassica pathogens. GSLs, GHPs, and methanolic leaf extracts inhibited the development of the pathogens tested compared to the control, and the effect was dose dependent. Furthermore, the biocide effects of the different compounds studied were dependent on the species and race of the pathogen. These results indicate that GSLs and their GHPs, as well as extracts of different Brassica species, have potential to inhibit pathogen growth and offer new opportunities to study the use of Brassica crops in biofumigation for the control of multiple diseases. PMID:25362058

  12. The Antimicrobial effects of Glucosinolates Hydrolysis compounds on E. Coli O157:H12 into field soil

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Introduction: Soil can be a source of pre-harvest contamination of produce by pathogens. Natural antimicrobials such as glucosinolate-hydrolyzed products (GHP) found in Brassicaceae family crops can be used as a green manure to control enteric pathogens in soil. Purpose: The antimicrobial activit...

  13. Impact of selenium supply on se-methylselenocysteine and glucosinolates accumulation in selenium-biofortified brassica sprouts

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Brassica sprouts are widely marketed as functional foods. Here we examined the effects of Se treatment on the accumulation of anticancer compound Se-methylselenocysteine (SeMSCys) and glucosinolates in Brassica sprouts. Cultivars from the six most extensively consumed Brassica vegetables (broccoli, ...

  14. Glucosinolate-derived compounds as a green manure for controlling Escherichia coli O157:H7 and Salmonella in soil

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Plants from the Brassica family contain glucosinolate-derived compounds (GDC) which may act as natural antimicrobials in soil. Consequently, Brassica cover crops planted after harvest of the primary crop in the fall, and/or ntercropped during the growing season, could provide benefits derived from...

  15. Naturally-Occurring Glucosinolates, Glucoraphanin and Glucoerucin, are Antagonists to Aryl Hydrocarbon Receptor as Their Chemopreventive Potency.

    PubMed

    Abdull Razis, Ahmad Faizal; Noor, Noramaliza Mohd

    2015-01-01

    As a cytosolic transcription factor, the aryl hydrocarbon (Ah) receptor is involved in several patho- physiological events leading to immunosuppression and cancer; hence antagonists of the Ah receptor may possess chemoprevention properties. It is known to modulate carcinogen-metabolising enzymes, for instance the CYP1 family of cytochromes P450 and quinone reductase, both important in the biotransformation of many chemical carcinogens via regulating phase I and phase II enzyme systems. Utilising chemically-activated luciferase expression (CALUX) assay it was revealed that intact glucosinolates, glucoraphanin and glucoerucin, isolated from Brassica oleracea L. var. acephala sabellica and Eruca sativa ripe seeds, respectively, are such antagonists. Both glucosinolates were poor ligands for the Ah receptor; however, they effectively antagonised activation of the receptor by the avid ligand benzo[a]pyrene. Indeed, intact glucosinolate glucoraphanin was a more potent antagonist to the receptor than glucoerucin. It can be concluded that both glucosinolates effectively act as antagonists for the Ah receptor, and this may contribute to their established chemoprevention potency. PMID:26320454

  16. The crystal structure of the thiocyanate-forming protein from Thlaspi arvense, a kelch protein involved in glucosinolate breakdown.

    PubMed

    Gumz, Frauke; Krausze, Joern; Eisenschmidt, Daniela; Backenköhler, Anita; Barleben, Leif; Brandt, Wolfgang; Wittstock, Ute

    2015-09-01

    Kelch repeat-containing proteins are involved in diverse cellular processes, but only a small subset of plant kelch proteins has been functionally characterized. Thiocyanate-forming protein (TFP) from field-penny cress, Thlaspi arvense (Brassicaceae), is a representative of specifier proteins, a group of kelch proteins involved in plant specialized metabolism. As components of the glucosinolate-myrosinase system of the Brassicaceae, specifier proteins determine the profile of bioactive products formed when plant tissue is disrupted and glucosinolates are hydrolyzed by myrosinases. Here, we describe the crystal structure of TaTFP at a resolution of 1.4 Å. TaTFP crystallized as homodimer. Each monomer forms a six-blade β-propeller with a wide "top" and a narrower "bottom" opening with distinct strand-connecting loops protruding far beyond the lower propeller surface. Molecular modeling and mutational analysis identified residues for glucosinolate aglucone and Fe(2+) cofactor binding within these loops. As the first experimentally determined structure of a plant kelch protein, the crystal structure of TaTFP not only enables more detailed mechanistic studies on glucosinolate breakdown product formation, but also provides a new basis for research on the diverse roles and mechanisms of other kelch proteins in plants. PMID:26260516

  17. Taste detection of the non-volatile isothiocyanate moringin results in deterrence to glucosinolate-adapted insect larvae.

    PubMed

    Müller, Caroline; van Loon, Joop; Ruschioni, Sara; De Nicola, Gina Rosalinda; Olsen, Carl Erik; Iori, Renato; Agerbirk, Niels

    2015-10-01

    Isothiocyanates (ITCs), released from Brassicales plants after hydrolysis of glucosinolates, are known for their negative effects on herbivores but mechanisms have been elusive. The ITCs are initially present in dissolved form at the site of herbivore feeding, but volatile ITCs may subsequently enter the gas phase and all ITCs may react with matrix components. Deterrence to herbivores resulting from topically applied volatile ITCs in artificial feeding assays may hence lead to ambiguous conclusions. In the present study, the non-volatile ITC moringin (4-(α-L-rhamnopyranosyloxy)benzyl ITC) and its glucosinolate precursor glucomoringin were examined for effects on behaviour and taste physiology of specialist insect herbivores of Brassicales. In feeding bioassays, glucomoringin was not deterrent to larvae of Pieris napi (Lepidoptera: Pieridae) and Athalia rosae (Hymenoptera: Tenthredinidae), which are adapted to glucosinolates. Glucomoringin stimulated feeding of larvae of the related Pieris brassicae (Lepidoptera: Pieridae) and also elicited electrophysiological activity from a glucosinolate-sensitive gustatory neuron in the lateral maxillary taste sensilla. In contrast, the ITC moringin was deterrent to P. napi and P. brassicae at high levels and to A. rosae at both high and low levels when topically applied to cabbage leaf discs (either 12, 120 or 1200 nmol moringin per leaf disc of 1cm diameter). Survival of A. rosae was also significantly reduced when larvae were kept on leaves treated with moringin for several days. Furthermore, moringin elicited electrophysiological activity in a deterrent-sensitive neuron in the medial maxillary taste sensillum of P. brassicae, providing a sensory mechanism for the deterrence and the first known ITC taste response of an insect. In simulated feeding assays, recovery of moringin was high, in accordance with its non-volatile nature. Our results demonstrate taste-mediated deterrence of a non-volatile, natural ITC to glucosinolate

  18. Determination of aliphatic hydrocarbons in the alga Himanthalia elongata.

    PubMed

    Punín Crespo, M O; Lage Yusty, M A

    2004-02-01

    The algae considered new foods according to Regulation CE 258/97 need a guarantee of their healthfulness before being in the European market. In this work ten samples of the brown alga Himanthalia elongata have been analyzed with the aim of verifying the absence of aliphatic hydrocarbons, due to the ability of the macroalgae to capture lipophilic organic compounds of the marine water coming from accidental or continuous leaks of raw oil and refined products, which happen each year with the growth of the industrialization and the demand of energy. The fat of the samples were Soxhlet extracted using hexane:dichloromethane (1:1) for 7h. The organic fractions were purified using silica microcolumns. The identification and quantification of the aliphatic hydrocarbons have been carried out using gas chromatography (GC) with flame ionization detector (FID). The total hydrocarbon content was between 14.8 and 40.2 microg g(-1) dry weight. PMID:14759670

  19. Biodegradation of Trihalomethanes and Other Halogenated Aliphatic Compounds

    NASA Technical Reports Server (NTRS)

    Smith, G. B.

    1996-01-01

    The biological dehalogenation of common water pollutants such as trichloromethane (chloroform) and other halogenated aliphatic compounds was the subject of this project. Samples from diverse water environments such as from groundwater contaminated with halogenated compounds and wastewaters from regional treatment plants were studied to identify conditions that favor certain dehalogenation reactions over others. Gene probe analyses of DNA extracted from the dichlormethane-degrading wastewater indicated the presence of the gene coding for dichloromethane dehalogenase, indicating the genetic basis for the dechlorination activity observed. These studies indicate that methanogenic bacteria are the organisms responsible for the chloroform dechlorination. Dechlorination of a common chlorofluorocarbon (CFC-11) was identified in samples taken from a regional aquifer contaminated with halogenated aliphatic compounds.

  20. Aliphatics hydrocarbon content in surface sediment from Jakarta Bay, Indonesia

    NASA Astrophysics Data System (ADS)

    YAzis, M.; Asia, L.; Piram, A.; Doumenq, P.; Syakti, A. D.

    2016-02-01

    Sedimentary aliphatic hydrocarbons content have been studied quantitatively and qualitatively using GC/MS method in eight coastal stations located in the Jakarta Bay, North of Jakarta, Indonesia. The total concentrations n-alkanes have ranged from 480 μg.kg-1to 1,935 μg.kg-1sediment dry weight. Several ratios (e.g. CPI24-32, NAR, TAR, Pr/Phy, n-C17/Pr, n- C18/Phyt,n-C29/n-C17, Ʃn-alkanes/n-C16LMW/HMW, Paq and TMD) were used to evaluate the possible sources of terrestrial-marine inputs of these hydrocarbons in the sediments. The various origins of aliphatic hydrocarbons were generally biogenic, including both terrigenous and marine, with an anthropogenic pyrolytic contribution (petrogenic and biogenic combustion). Two stations (G,H) were thehighest concentration and had potential risk to environment

  1. Manganese-Mediated Coupling Reaction of Vinylarenes and Aliphatic Alcohols

    PubMed Central

    Zhang, Wei; Wang, Nai-Xing; Bai, Cui-Bing; Wang, Yan-Jing; Lan, Xing-Wang; Xing, Yalan; Li, Yi-He; Wen, Jia-Long

    2015-01-01

    Alcohols and alkenes are the most abundant and commonly used organic building blocks in the large-scale chemical synthesis. Herein, this is the first time to report a novel and operationally simple coupling reaction of vinylarenes and aliphatic alcohols catalyzed by manganese in the presence of TBHP (tert-butyl hydroperoxide). This coupling reaction provides the oxyalkylated products of vinylarenes with good regioselectivity and accomplishes with the principles of step-economies. A possible reaction mechanism has also been proposed. PMID:26470633

  2. 40 CFR 721.4490 - Capped aliphatic isocyanate.

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... reporting. (1) The chemical substance identified generically as a capped aliphatic isocyanate (PMN P-86-1146...) (concentration set at 0.1 percent), (f), (h)(1)(ii)(G), (h)(1)(iii)(A), (h)(1)(iii)(B), (h)(1)(iii)(D), and (h)(1...(h). (iv) Disposal. Requirements as specified in § 721.90 (a)(1), (a)(2), (b)(1), (b)(2), (c)(1),...

  3. 40 CFR 721.4490 - Capped aliphatic isocyanate.

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... reporting. (1) The chemical substance identified generically as a capped aliphatic isocyanate (PMN P-86-1146...) (concentration set at 0.1 percent), (f), (h)(1)(ii)(G), (h)(1)(iii)(A), (h)(1)(iii)(B), (h)(1)(iii)(D), and (h)(1...(h). (iv) Disposal. Requirements as specified in § 721.90 (a)(1), (a)(2), (b)(1), (b)(2), (c)(1),...

  4. 40 CFR 721.4490 - Capped aliphatic isocyanate.

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... reporting. (1) The chemical substance identified generically as a capped aliphatic isocyanate (PMN P-86-1146...) (concentration set at 0.1 percent), (f), (h)(1)(ii)(G), (h)(1)(iii)(A), (h)(1)(iii)(B), (h)(1)(iii)(D), and (h)(1...(h). (iv) Disposal. Requirements as specified in § 721.90 (a)(1), (a)(2), (b)(1), (b)(2), (c)(1),...

  5. 40 CFR 721.4490 - Capped aliphatic isocyanate.

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... reporting. (1) The chemical substance identified generically as a capped aliphatic isocyanate (PMN P-86-1146...) (concentration set at 0.1 percent), (f), (h)(1)(ii)(G), (h)(1)(iii)(A), (h)(1)(iii)(B), (h)(1)(iii)(D), and (h)(1...(h). (iv) Disposal. Requirements as specified in § 721.90 (a)(1), (a)(2), (b)(1), (b)(2), (c)(1),...

  6. Rhodium-Catalyzed Enantioselective Arylation of Aliphatic Imines.

    PubMed

    Kato, Naoya; Shirai, Tomohiko; Yamamoto, Yasunori

    2016-06-01

    Chiral rhodium(I)-catalyzed highly enantioselective arylation of aliphatic N-sulfonyl aldimines with arylboronic acids has been developed. This transformation is achieved by the use of a rhodium/bis(phosphoramidite) catalyst to give enantiomerically enriched α-branched amines (up to 99 % ee). In addition, this system enables efficient synthesis of (+)-NPS R-568 and Cinacalcet which are calcimimetic agents. PMID:27119262

  7. Mechanics of networks of aliphatic fibers in aqueous surfactant media

    NASA Astrophysics Data System (ADS)

    Zanchetta, Giuliano; Caggioni, Marco; Guida, Vincenzo; Trappe, Veronique

    2012-02-01

    We investigate the structural and rheological properties of aliphatic fibers dispersed in aqueous solutions of anionic surfactants, typically used in liquid detergents to provide yield stress. This system displays an onset to solid-like properties that depends on fiber concentration. In this contribution we will discuss how tuning the state of the surfactant background influences the fiber-fiber interactions and the mechanical properties of the gel.

  8. Aerobic microorganism for the degradation of chlorinated aliphatic hydrocarbons

    DOEpatents

    Fliermans, Carl B.

    1989-01-01

    A chlorinated aliphatic hydrocarbon-degrading microorganism, having American Type Culture Collection accession numbers ATCC 53570 and 53571, in a biologically pure culture aseptically collected from a deep subsurface habitat and enhanced, mineralizes trichloroethylene and tetrachloroethylene to HCl, H.sub.2 O and Co.sub.2 under aerobic conditions stimulated by methane, acetate, methanol, tryptone-yeast extract, propane and propane-methane.

  9. Manganese-Mediated Coupling Reaction of Vinylarenes and Aliphatic Alcohols.

    PubMed

    Zhang, Wei; Wang, Nai-Xing; Bai, Cui-Bing; Wang, Yan-Jing; Lan, Xing-Wang; Xing, Yalan; Li, Yi-He; Wen, Jia-Long

    2015-01-01

    Alcohols and alkenes are the most abundant and commonly used organic building blocks in the large-scale chemical synthesis. Herein, this is the first time to report a novel and operationally simple coupling reaction of vinylarenes and aliphatic alcohols catalyzed by manganese in the presence of TBHP (tert-butyl hydroperoxide). This coupling reaction provides the oxyalkylated products of vinylarenes with good regioselectivity and accomplishes with the principles of step-economies. A possible reaction mechanism has also been proposed. PMID:26470633

  10. Manganese-Mediated Coupling Reaction of Vinylarenes and Aliphatic Alcohols

    NASA Astrophysics Data System (ADS)

    Zhang, Wei; Wang, Nai-Xing; Bai, Cui-Bing; Wang, Yan-Jing; Lan, Xing-Wang; Xing, Yalan; Li, Yi-He; Wen, Jia-Long

    2015-10-01

    Alcohols and alkenes are the most abundant and commonly used organic building blocks in the large-scale chemical synthesis. Herein, this is the first time to report a novel and operationally simple coupling reaction of vinylarenes and aliphatic alcohols catalyzed by manganese in the presence of TBHP (tert-butyl hydroperoxide). This coupling reaction provides the oxyalkylated products of vinylarenes with good regioselectivity and accomplishes with the principles of step-economies. A possible reaction mechanism has also been proposed.

  11. Biodegradation of aliphatic vs. aromatic hydrocarbons in fertilized arctic soils

    USGS Publications Warehouse

    Braddock, J.F.

    1999-01-01

    A study was carried out to test a simple bioremediation treatment strategy in the Arctic and analyze the influence of fertilization the degradation of aliphatic and aromatic hydrocarbons, e.g., pristine, n-tetradecane, n-pentadecane, 2-methylnaphthalene, naphthalene, and acenaphthalene. The site was a coarse sand pad that once supported fuel storage tanks. Diesel-range organics concentrations were 250-860 mg/kg soil at the beginning of the study. Replicate field plots treated with fertilizer yielded final concentrations of 0, 50, 100, or 200 mg N/kg soil. Soil pH and soil-water potentials decreased due to fertilizer application. The addition of fertilizer considerably increased soil respiration potentials, but not the populations of microorganisms measured. Fertilizer addition also led to ??? 50% loss of measured aliphatic and aromatic hydrocarbons in surface and subsurface soils. For fertilized plots, hydrocarbon loss was not associated with the quantity of fertilizer added. Losses of aliphatic hydrocarbons were ascribed to biotic processes, while losses of aromatic hydrocarbons were due to biotic and abiotic processes.

  12. Conventional and modified hydrodistillation method for the extraction of glucosinolate hydrolytic products: a comparative account.

    PubMed

    Arora, Rohit; Singh, Bikram; Vig, Adarsh Pal; Arora, Saroj

    2016-01-01

    Eruca sativa is extensively used as raw and its oil is also used for cooking due to its exceptional flavour. The volatile nature of the hydrolytic products of glucosinolates makes the extraction difficult. The hydrodistillation method used previously yield very less amount of the extract as well as the absence of stirring in the round bottom flask causes burning of both the crushed seeds and the flask. To overcome these drawbacks, a method has been developed using magnetic stirrer and hot plate. The yield and composition of hydrolytic products in the extract with the modified method was increased along with an increase in the amount of major hydrolytic products as seen by GC-MS. This method thus has immense potential in pharmaceutical industries, due to the ease of extraction and isolation. PMID:27217994

  13. Nitrates and Glucosinolates as Strong Determinants of the Nutritional Quality in Rocket Leafy Salads

    PubMed Central

    Cavaiuolo, Marina; Ferrante, Antonio

    2014-01-01

    Rocket is an important leafy vegetable crop and a good source of antioxidants and anticancer molecules such as glucosinolates and other sulfur compounds. Rocket is also a hyper-accumulator of nitrates which have been considered for long time the main factors that cause gastro-intestinal cancer. In this review, the content of these compounds in rocket tissues and their levels at harvest and during storage are discussed. Moreover, the effect of these compounds in preventing or inducing human diseases is also highlighted. This review provides an update to all the most recent studies carried out on rocket encouraging the consumption of this leafy vegetable to reduce the risk of contracting cancer and other cardiovascular diseases. PMID:24736897

  14. Development of a liquid chromatography-electrospray ionization-tandem mass spectrometry method for the simultaneous analysis of intact glucosinolates and isothiocyanates in Brassicaceae seeds and functional foods.

    PubMed

    Franco, P; Spinozzi, S; Pagnotta, E; Lazzeri, L; Ugolini, L; Camborata, C; Roda, A

    2016-01-01

    A new high pressure liquid chromatography-electrospray ionization-tandem mass spectrometry method for the simultaneous determination of glucosinolates, as glucoraphanin and glucoerucin, and the corresponding isothiocyanates, as sulforaphane and erucin, was developed and applied to quantify these compounds in Eruca sativa defatted seed meals and enriched functional foods. The method involved solvent extraction, separation was achieved in gradient mode using water with 0.5% formic acid and acetonitrile with 0.5% formic acid and using a reverse phase C18 column. The electrospray ion source operated in negative and positive mode for the detection of glucosinolates and isothiocyanates, respectively, and the multiple reaction monitoring (MRM) was selected as acquisition mode. The method was validated following the ICH guidelines. Replicate experiments demonstrated a good accuracy (bias%<10%) and precision (CV%<10%). Detection limits and quantification limits are in the range of 1-400ng/mL for each analytes. Calibration curves were validated on concentration ranges from 0.05 to 50μg/mL. The method proved to be suitable for glucosinolates and isothiocyanates determination both in biomasses and in complex matrices such as food products enriched with glucosinolates, or nutraceutical bakery products. In addition, the developed method was applied to the simultaneous determination of glucosinolates and isothiocyanates in bakery product enriched with glucosinolates, to evaluate their thermal stability after different industrial processes from cultivation phases to consumer processing. PMID:26363943

  15. Cost-Benefit Analysis for Alternatives to Aliphatic Isocyanate Polyurethanes

    NASA Technical Reports Server (NTRS)

    Lewis, Pattie

    2007-01-01

    NASA and Air Force Space Command (AFSPC) have similar missions and therefore similar facilities and structures in similar environments. The standard practice for protecting metallic substrates in atmospheric environments is the application of an applied coating system. The most common topcoats used in coating systems are polyurethanes that contain isocyanates. Isocyanates are classified as potential human carcinogens and are known to cause cancer in animals. The primary objective of this effort was to demonstrate and validate alternatives to aliphatic isocyanate polyurethanes resulting in one or more isocyanate-free coatings qualified for use at AFSPC and NASA installations participating in this project. This Cost-Benefit Analysis (CBA) quantifies the estimated capital and process costs of coating alternatives and cost savings relative to the current coatings. The estimates in this CBA are to be used for assessing the relative merits of the selected alternatives. The actual economic effects at any specific facility will depend on the alternative material or technology implemented, the number of actual applications converted, future workloads, and other factors . The participants initially considered eighteen (18) alternative coatings as described in the Potential Alternatives Report entitled Potential Alternatives Report for Validation of Alternatives to Aliphatic Isocyanate Polyurethanes, prepared by ITB. Of those, 8 alternatives were selected for testing in accordance with the Joint Test Protocol entitled Joint Test Protocol for Validation of Alternatives to Aliphatic Isocyanate Polyurethanes, and the Field Test Plan entitled Field Evaluations Test Plan for Validation of Alternatives 10 Aliphatic Isocyanate Polyurethanes, both of which were prepared by ITB. A joint Test Report entitled Joint Test Report for Validation of Alternatives to Aliphatic Isocyanate Polyurethanes, prepared by ITB, documents the results of the laboratory and field testing, as well as any

  16. Phosphorylation at serine 52 and 635 does not alter the transport properties of glucosinolate transporter AtGTR1

    PubMed Central

    Jørgensen, Morten Egevang; Olsen, Carl Erik; Halkier, Barbara Ann; Nour-Eldin, Hussam Hassan

    2016-01-01

    Little is known about how plants regulate transporters of defense compounds. In A. thaliana, glucosinolates are transported between tissues by NPF2.10 (AtGTR1) and NPF2.11 (AtGTR2). Mining of the PhosPhat4.0 database showed two cytosol exposed phosphorylation sites for AtGTR1 and one membrane-buried phosphorylation site for AtGTR2. In this study, we investigate whether mutation of the two potential regulatory sites of AtGTR1 affected transport of glucosinolates in Xenopus oocytes. Characterization of AtGTR1 phosphorylation mutants showed that phosphorylation of AtGTR1 - at the two reported phosphorylation sites - is not directly involved in regulating AtGTR1 transport activity. We hypothesize a role for AtGTR1-phosphorylation in regulating protein-protein interactions. PMID:26340317

  17. Effect of Se treatment on glucosinolate metabolism and health-promoting compounds in the broccoli sprouts of three cultivars.

    PubMed

    Tian, Ming; Xu, Xiaoyun; Liu, Yanlong; Xie, Lin; Pan, Siyi

    2016-01-01

    Broccoli sprouts are natural functional foods for cancer prevention because of their high glucosinolate (GSL) content and high selenium (Se) accumulation capacity. The regulation mechanism of Se on GSL metabolism in broccoli sprouts was explored. In particular, the effects of Se treatment (100 μmol/L selenite and selenate) on the Se, sulfur (S), glucosinolate and sulforaphane contents; myrosinase activity and health-promoting compounds (ascorbic acid, anthocyanin, total phenolics and flavonoids) of three, 5 day old, cultivars were investigated. The treatment did not influence the total GSL and ascorbic acid contents; significantly increased the myrosinase activity and sulforaphane, anthocyanin and flavonoids contents; and decreased the total phenolics content. The increase in sulforaphane during early growth can be primarily attributed to the increased myrosinase activity caused by Se treatment. Broccoli sprouts with suitable selenite and selenate concentrations, in the early growth days, could be desirable for improved human health. PMID:26212985

  18. The influence of collection zone on glucosinolates, polyphenols and flavonoids contents and biological profiles of Capparis sicula ssp. sicula.

    PubMed

    Conforti, F; Marcotullio, M C; Menichini, F; Statti, G A; Vannutelli, L; Burini, G; Menichini, F; Curini, M

    2011-04-01

    This study aimed to evaluate the influence of collection zone on total phenol, flavonoid and glucosinolate contents and antioxidant and anti-inflammatory activities of caper (Capparis sicula ssp. sicula). This species has been characterized through the detection, isolation and quantitative evaluation of chemical markers (polyphenols, flavonoids and glucosinolates). The chemical investigation showed a different composition between the two collection zones. While the total amounts of phenolics and flavonoids of the two samples were quite the same, their high-performance liquid chromatography profiles were very different. In both samples, the most abundant aglycone was quercetin which accounted for 60% of total flavonoids. Nuclear magnetic resonance data analysis allowed the identification of two compounds: 3,5-dicaffeoylquinic and 4,5-dicaffeoylquinic acids which represented 6.67% and 15.94%, respectively, of the total amount of flavonoids in sample 1. In sample 2, these two acids were still present, but their percentages were much less (2.20% and 1.71%, respectively). As far as we know, this is the first report about the presence of dicaffeoylquinic acids in Capparis. With regard to glucosinolate content, sample 1 showed a higher content of glucosinolates. In both samples, glucocapparin was the most abundant compound. Antioxidant activity of the methanolic C. sicula extracts using diphenyl picrylhydrazyl, β-carotene bleaching test and oxygen radical absorbance capacity showed that the sample 2 was more active than 1. As regards the inhibition of NO production, the extracts from sample 2 were more active than those from sample 1. PMID:21436235

  19. Trade-off between constitutive and inducible resistance against herbivores is only partially explained by gene expression and glucosinolate production

    PubMed Central

    Rasmann, Sergio; Chassin, Estelle; Bilat, Julia; Glauser, Gaétan; Reymond, Philippe

    2015-01-01

    The hypothesis that constitutive and inducible plant resistance against herbivores should trade-off because they use the same resources and impose costs to plant fitness has been postulated for a long time. Negative correlations between modes of deployment of resistance and defences have been observed across and within species in common garden experiments. It was therefore tested whether that pattern of resistance across genotypes follows a similar variation in patterns of gene expression and chemical defence production. Using the genetically tractable model Arabidopsis thaliana and different modes of induction, including the generalist herbivore Spodoptera littoralis, the specialist herbivore Pieris brassicae, and jasmonate application, constitutive and inducibility of resistance was measured across seven A. thaliana accessions that were previously selected based on constitutive levels of defence gene expression. According to theory, it was found that modes of resistance traded-off among accessions, particularly against S. littoralis, in which accessions investing in high constitutive resistance did not increase it substantially after attack and vice-versa. Accordingly, the average expression of eight genes involved in glucosinolate production negatively predicted larval growth across the seven accessions. Glucosinolate production and genes related to defence induction on healthy and herbivore-damaged plants were measured next. Surprisingly, only a partial correlation between glucosinolate production, gene expression, and the herbivore resistance results was found. These results suggest that the defence outcome of plants against herbivores goes beyond individual molecules or genes but stands on a complex network of interactions. PMID:25716695

  20. Trade-off between constitutive and inducible resistance against herbivores is only partially explained by gene expression and glucosinolate production.

    PubMed

    Rasmann, Sergio; Chassin, Estelle; Bilat, Julia; Glauser, Gaétan; Reymond, Philippe

    2015-05-01

    The hypothesis that constitutive and inducible plant resistance against herbivores should trade-off because they use the same resources and impose costs to plant fitness has been postulated for a long time. Negative correlations between modes of deployment of resistance and defences have been observed across and within species in common garden experiments. It was therefore tested whether that pattern of resistance across genotypes follows a similar variation in patterns of gene expression and chemical defence production. Using the genetically tractable model Arabidopsis thaliana and different modes of induction, including the generalist herbivore Spodoptera littoralis, the specialist herbivore Pieris brassicae, and jasmonate application, constitutive and inducibility of resistance was measured across seven A. thaliana accessions that were previously selected based on constitutive levels of defence gene expression. According to theory, it was found that modes of resistance traded-off among accessions, particularly against S. littoralis, in which accessions investing in high constitutive resistance did not increase it substantially after attack and vice-versa. Accordingly, the average expression of eight genes involved in glucosinolate production negatively predicted larval growth across the seven accessions. Glucosinolate production and genes related to defence induction on healthy and herbivore-damaged plants were measured next. Surprisingly, only a partial correlation between glucosinolate production, gene expression, and the herbivore resistance results was found. These results suggest that the defence outcome of plants against herbivores goes beyond individual molecules or genes but stands on a complex network of interactions. PMID:25716695

  1. Structural studies of aliphatic substituted phthalocyanine-lipid multilayers.

    PubMed

    Zarbakhsh, Ali; Campana, Mario; Mills, David; Webster, John R P

    2010-10-01

    A Langmuir-Blodgett film of aliphatic substituted phthalocyanines on a C18 silane supporting layer coupled onto a silicon substrate has been investigated using neutron reflectometry. This multilayer structure is seen as a possible candidate for phthalocyanine-lipid biosensor devices. The results show the suitability of the C18 ligands as an anchoring layer for the phthalocyanines. The scattering length density profiles demonstrate the effectiveness of a lipid monolayer in partitioning the composition of phthalocyanine layers from that of the bulk liquid. The effectiveness of this barrier is a critical factor in the efficiency of such devices. PMID:20831252

  2. Decarboxylative Fluorination of Aliphatic Carboxylic Acids via Photoredox Catalysis

    PubMed Central

    Ventre, Sandrine; Petronijevic, Filip R.; MacMillan, David W. C.

    2016-01-01

    The direct conversion of aliphatic carboxylic acids to the corresponding alkyl fluorides has been achieved via visible light-promoted photoredox catalysis. This operationally simple, redox-neutral fluorination method is amenable to a wide variety of carboxylic acids. Photon-induced oxidation of carboxylates leads to the formation of carboxyl radicals, which upon rapid CO2-extrusion and F• transfer from a fluorinating reagent yield the desired fluoroalkanes with high efficiency. Experimental evidence indicates that an oxidative quenching pathway is operable in this broadly applicable fluorination protocol. PMID:25881929

  3. Aliphatic Polyethers: Classical Polymers for the 21st Century.

    PubMed

    Klein, Rebecca; Wurm, Frederik R

    2015-06-01

    Polyethers-polymers with the structural element (R'-O-R)n in their backbone--are an old class of polymers which were already used at the time of the ancient Egyptians. However, still today these materials are highly important with applications in all areas of our life, reaching from the automotive and paper industry to cosmetics and biomedical applications. In this Review, different aliphatic polyethers like poly(epoxide)s, poly(oxetane)s, and poly(tetrahydrofuran) are discussed. Special emphasis is placed on the history, the polymerization techniques (industrially and in academia), the properties, the applications as well as recent developments of these materials. PMID:25967116

  4. Different aliphatic dicarboxylates affected assemble of new coordination polymers constructed from flexible-rigid mixed ligands

    SciTech Connect

    Xu Xinxin; Ma Ying; Wang Enbo

    2007-11-15

    In this article, seven coordination polymers: [Cd(C{sub 5}H{sub 6}O{sub 4})(C{sub 10}H{sub 8}N{sub 2})]{sub n} (1), [Zn(C{sub 5}H{sub 6}O{sub 4})(C{sub 10}H{sub 8}N{sub 2})]{sub n} (2), [Cd(C{sub 6}H{sub 8}O{sub 4})(C{sub 10}H{sub 8}N{sub 2})]{sub n} (3), {l_brace}[Mn(C{sub 10}H{sub 8}N{sub 2})(H{sub 2}O){sub 4}] (C{sub 4}H{sub 4}O{sub 4}).4H{sub 2}O{r_brace}{sub n} (4), [Mn{sub 5}(C{sub 4}H{sub 4}O{sub 4}){sub 4}(O)]{sub n} (5), [Cd(C{sub 4}H{sub 4}O{sub 4})(C{sub 10}H{sub 8}N{sub 2})(H{sub 2}O)]{sub n} (6) and [Zn(C{sub 6}H{sub 6}O{sub 4})(C{sub 12}H{sub 8}N{sub 2})(H{sub 2}O)]{sub n} (7) were synthesized and characterized by single-crystallographic X-ray diffraction. Compounds 1 and 2 are two-dimensional layers connected by glutarate anions and 4,4'-bpy. Unlike compounds 1 and 2, compound 3 is a two-fold interpenetration network. Compound 4 is a one-dimensional chain-like structure, which is further extended to two-dimensional supramolecular layer structure with hydrogen bond. During the synthesis of compound 4, to our surprise, we got compound 5; compound 5 is an interesting three-dimensional network composed of pentanuclear Mn(II) building units and succinate anions. Compound 6 is also a two-dimensional supramolecular layer structure composed of one-dimensional chain-like structure with hydrogen bonds and {pi}-{pi} interactions. Compound 7 is also a one-dimensional chain-like structure, which is further connected with the same kind of interaction to generate two-dimensional supramolecular layer structure. Furthermore, compounds 1 and 2 both exhibit fluorescent property at room temperature. - Graphical abstract: Seven complexes composed by 3D metal ions, aliphatic acid ligand and rigid bidentate nitrogen ligands: 4,4'-bpy, 2,2'-bpy and 1,10'-phen. With the change of the carbon number of the backbone of aliphatic dicarboxylate ligand, we can synthesize different complexes with various structures.

  5. Polarized Raman spectra and intensities of aliphatic amino acids

    NASA Astrophysics Data System (ADS)

    Himmler, Hans J.; Eysel, Hans H.

    1989-01-01

    Raman spectra of aliphatic α- L-amino acids, glycine, alanine, and valine were re-investigated both in aqueous solution and deuterium oxide solution. The spectra were taken of the zwitterionic and of the completely deprotonated form of the amino acids. Spectra of leucine and isoleucine were studied in water at the isoelectric point. Spectra were recorded both with parallel and perpendicular polarization and the isotropic and anisotropic scattering components were isolated. The integrated intensities of CH stretch, CC stretch and carboxylate bend vibrations are discussed. Linear relations between the number of CC and CH bonds and the total scattered intensity in the appropriate spectral regions are observed. The sum over the carboxylate modes shows characteristic intensities for the first three members of the aliphatic amino acids. An increase of isotropic scattering of ϱ co 2 near 510 cm -1 with increasing chain length of the amino acid (or with increasing concentration) is interpreted as the result of micelle formation.

  6. Tailoring NO donors metallopharmaceuticals: ruthenium nitrosyl ammines and aliphatic tetraazamacrocycles.

    PubMed

    Tfouni, E; Doro, F G; Figueiredo, L E; Pereira, J C M; Metzker, G; Franco, D W

    2010-01-01

    The discovery of the involvement of nitric oxide (NO) in several physiological and pathophysiological processes launched a spectacular increase in studies in areas such as chemistry, biochemistry, and pharmacology. As a consequence, the development of NO donors or scavengers for regulation of its concentration and bioavailability in vivo is required. In this sense, ruthenium nitrosyl ammines and aliphatic tetraazamacrocyles have attracted a lot of attention due to their unique chemical properties. These complexes are water soluble and stable in solution, not to mention that they can deliver NO when photochemically or chemically activated by the reduction of the coordinated nitrosonium (NO+). The tuning of the energies of the charge transfer bands, the redox potential, and the specific rate constants of NO liberation, in both solution and matrices, is desirable for the achievement of selective NO delivery to biological targets, hence making the ruthenium ammines and aliphatic tetraazamacrocyles a quite versatile platform for biological application purposes. These ruthenium nitrosyls have shown to be active in firing neurons in mouse hippocampus, performing redox reactions in mitochondria, acting in blood pressure control, exhibiting cytotoxic activities against trypanosomatids (T.cruzi and L.major) and tumor cells. This tailoring approach is explored here, being heavily supported by the accumulated knowledge on the chemistry and photochemistry of ruthenium complexes, which allows NO donors/scavengers systems to be custom made designed. PMID:20846113

  7. Terrestrial ecotoxicity of short aliphatic protic ionic liquids.

    PubMed

    Peric, Brezana; Martí, Esther; Sierra, Jordi; Cruañas, Robert; Iglesias, Miguel; Garau, Maria Antonia

    2011-12-01

    A study of the ecotoxicity of different short aliphatic protic ionic liquids (PILs) on terrestrial organisms was conducted. Tests performed within the present study include those assessing the effects of PILs on soil microbial functions (carbon and nitrogen mineralization) and terrestrial plants. The results show that the nominal lowest-observed-adverse-effect concentration (LOAEC) values were 5,000 mg/kg (dry soil) for the plant test in two species (Lolium perenne, Allium cepa), 1,000 mg/kg (dry soil) for the plant test in one species (Raphanus sativus), and 10,000 mg/kg (dry soil) for carbon and nitrogen microbial transformation tests (all concentrations are nominal). Most of the median effective concentration values (EC50) were above 1,000 mg/kg (dry soil). Based on the obtained results, these compounds can be described as nontoxic for soil microbiota and the analyzed plants, and potentially biodegradable in soils, as can be deduced from the respirometric experiment. The toxicity rises with the increase of complexity of the PILs molecule (branch and length of aliphatic chain) among the three PILs analyzed. PMID:21935980

  8. Short-chain aliphatic ester synthesis using Thermobifida fusca cutinase.

    PubMed

    Su, Lingqia; Hong, Ruoyu; Guo, Xiaojie; Wu, Jing; Xia, Yongmei

    2016-09-01

    Short-chain aliphatic esters are commonly used as fruit flavorings in the food industry. In this study, Thermobifida fusca (T. fusca) cutinase was used for the synthesis of aliphatic esters, and the maximum yield of ethyl caproate reached 99.2% at a cutinase concentration of 50U/ml, 40°C, and water content of 0.5%, representing the highest ester yield to date. The cutinase-catalyzed esterification displayed strong tolerance for water content (up to 8%) and acid concentration (up to 0.8M). At substrate concentrations ⩽0.8M, the ester yield remained above 80%. Moreover, ester yields of more than 98% and 95% were achieved for acids of C3-C8 and alcohols of C1-C6, respectively, indicating extensive chain length selectivity of the cutinase. These results demonstrate the superior ability of T. fusca cutinase to catalyze the synthesis of short-chain esters. This study provides the basis for industrial production of short-chain esters using T. fusca cutinase. PMID:27041308

  9. Kinetics of bacterial growth on chlorinated aliphatic compounds

    SciTech Connect

    Wijngaard, A.J. van den; Wind, R.E.; Janssen, D.B. )

    1993-07-01

    Halogenated aliphatic compounds are frequent constituents of industrial waste gases. Because of the environmental and biological toxic effects of these compounds, there is a growing interest in technologies for their removal. Biological waste gas purification is an option if specialized bacterial strains that use halogenated aliphatics as sole carbon and energy sources can be used. Elimination efficiency of the compounds depends not only on the process technology but on the degradation properties of the bacterial strains. Important aspects of bacterial growth are the Monod half-saturation constant and the maximum growth rate. In this study the kinetic properties of the organisms (Ancylobacter aquaticus AD20 and AD25, Xanthobacter autotrophicus GJ10, Pseudomonas sp. strain AD1) weree measured during growth in continuous cultures and wer compared with the kinetic properties of the first catabolic enzyme involved in the degradation of the growth substrate. The results indicate that the growth of the strains examined followed Monod kinetics. Stains AD20 and GJ10 showed growth rates on DCE somewhat higher than predicted from the amount of haloalkane dehalogenase present in the cells, while strain AD25 was much lower. 33 refs., 3 figs., 4 tabs.

  10. Exogenous Methyl Jasmonate Treatment Increases Glucosinolate Biosynthesis and Quinone Reductase Activity in Kale Leaf Tissue

    PubMed Central

    Ku, Kang-Mo; Jeffery, Elizabeth H.; Juvik, John A.

    2014-01-01

    Methyl jasmonate (MeJA) spray treatments were applied to the kale varieties ‘Dwarf Blue Curled Vates’ and ‘Red Winter’ in replicated field plantings in 2010 and 2011 to investigate alteration of glucosinolate (GS) composition in harvested leaf tissue. Aqueous solutions of 250 µM MeJA were sprayed to saturation on aerial plant tissues four days prior to harvest at commercial maturity. The MeJA treatment significantly increased gluconasturtiin (56%), glucobrassicin (98%), and neoglucobrassicin (150%) concentrations in the apical leaf tissue of these genotypes over two seasons. Induction of quinone reductase (QR) activity, a biomarker for anti-carcinogenesis, was significantly increased by the extracts from the leaf tissue of these two cultivars. Extracts of apical leaf tissues had greater MeJA mediated increases in phenolics, glucosinolate concentrations, GS hydrolysis products, and QR activity than extracts from basal leaf tissue samples. The concentration of the hydrolysis product of glucoraphanin, sulforphane was significantly increased in apical leaf tissue of the cultivar ‘Red Winter’ in both 2010 and 2011. There was interaction between exogenous MeJA treatment and environmental conditions to induce endogenous JA. Correlation analysis revealed that indole-3-carbanol (I3C) generated from the hydrolysis of glucobrassicin significantly correlated with QR activity (r = 0.800, P<0.001). Concentrations required to double the specific QR activity (CD values) of I3C was calculated at 230 µM, which is considerably weaker at induction than other isothiocyanates like sulforphane. To confirm relationships between GS hydrolysis products and QR activity, a range of concentrations of MeJA sprays were applied to kale leaf tissues of both cultivars in 2011. Correlation analysis of these results indicated that sulforaphane, NI3C, neoascorbigen, I3C, and diindolylmethane were all significantly correlated with QR activity. Thus, increased QR activity may be due to

  11. Synthesis of pyrimido[4,5-c]azepine- and pyrimido[4,5-c]oxepine-based γ-secretase modulators.

    PubMed

    Wu, Yong-Jin; Zhang, Yunhui; Toyn, Jeremy H; Macor, John E; Thompson, Lorin A

    2016-03-15

    This Letter describes an efficient ring-closing metathesis approach to 2-chloro-4-amino-pyrimido[4,5-c]azepines and 2-chloro-4-amino-pyrimido[4,5-c]oxepines. These chlorides were applied to the synthesis of several potent γ-secretase modulators (GSMs). PMID:26898338

  12. Specific glucosinolate analysis reveals variable levels of epimeric glucobarbarins, dietary precursors of 5-phenyloxazolidine-2-thiones, in watercress types with contrasting chromosome numbers.

    PubMed

    Agerbirk, Niels; Olsen, Carl Erik; Cipollini, Don; Ørgaard, Marian; Linde-Laursen, Ib; Chew, Frances S

    2014-10-01

    Watercress obtained in food stores in the United States contained significant levels of epiglucobarbarin [(R)-2-hydroxy-2-phenylethylglucosinolate] and low levels of the 2S-epimer glucobarbarin identified by an HPLC+NMR+MS/MS approach. Typical combined levels were 4-7 μmol/g dry wt. The hydrolysis product, 5-phenyloxazolidine-2-thione (barbarin), was detected at similar levels as the precursor glucosinolates after autolysis of fresh watercress in water. Fragmentation patterns in MS(2) of reference desulfoglucosinolates were side chain specific and suitable for routine identification. Watercress was of two main glucosinolate chemotypes: Material from U.S. food stores had a complex profile including glucobarbarins, gluconasturtiin, indole glucosinolates and high levels (6-28 μmol/g dry wt.) of long-chain methylsulfinylalkyl and methylthioalkyl glucosinolates. Material from European food stores had a simple profile dominated by gluconasturtiin, with low levels of epiglucobarbarin and moderate levels of indole glucosinolates. Some wild U.S. material was similar to the U.S. food store type. Both types were found to be Nasturtium officinale by floral parts morphology. Cytological analysis of one U.S. food store accession indicated that it represented a chromosome-doubled variant within N. officinale. The nutritional consequences and invasive potential of the U.S. food store chemotype are discussed. PMID:25226408

  13. 40 CFR 721.7250 - Polyaziridinyl ester of an aliphatic alcohol (generic).

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... alcohol (generic). 721.7250 Section 721.7250 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY... Specific Chemical Substances § 721.7250 Polyaziridinyl ester of an aliphatic alcohol (generic). (a... generically as a polyaziridinyl ester of an aliphatic alcohol (PMN P-01-97) is subject to reporting under...

  14. 40 CFR 721.7250 - Polyaziridinyl ester of an aliphatic alcohol (generic).

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... alcohol (generic). 721.7250 Section 721.7250 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY... Specific Chemical Substances § 721.7250 Polyaziridinyl ester of an aliphatic alcohol (generic). (a... generically as a polyaziridinyl ester of an aliphatic alcohol (PMN P-01-97) is subject to reporting under...

  15. 40 CFR 721.7250 - Polyaziridinyl ester of an aliphatic alcohol (generic).

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... alcohol (generic). 721.7250 Section 721.7250 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY... Specific Chemical Substances § 721.7250 Polyaziridinyl ester of an aliphatic alcohol (generic). (a... generically as a polyaziridinyl ester of an aliphatic alcohol (PMN P-01-97) is subject to reporting under...

  16. 40 CFR 721.7250 - Polyaziridinyl ester of an aliphatic alcohol (generic).

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... alcohol (generic). 721.7250 Section 721.7250 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY... Specific Chemical Substances § 721.7250 Polyaziridinyl ester of an aliphatic alcohol (generic). (a... generically as a polyaziridinyl ester of an aliphatic alcohol (PMN P-01-97) is subject to reporting under...

  17. 40 CFR 721.9952 - Alkoxylated aliphatic diisocyanate allyl ether (generic).

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... allyl ether (generic). 721.9952 Section 721.9952 Protection of Environment ENVIRONMENTAL PROTECTION... New Uses for Specific Chemical Substances § 721.9952 Alkoxylated aliphatic diisocyanate allyl ether... identified generically as alkoxylated aliphatic diisocyanate allyl ether (PMN P-00-0353) is subject...

  18. 40 CFR 721.9952 - Alkoxylated aliphatic diisocyanate allyl ether (generic).

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... allyl ether (generic). 721.9952 Section 721.9952 Protection of Environment ENVIRONMENTAL PROTECTION... New Uses for Specific Chemical Substances § 721.9952 Alkoxylated aliphatic diisocyanate allyl ether... identified generically as alkoxylated aliphatic diisocyanate allyl ether (PMN P-00-0353) is subject...

  19. 40 CFR 721.2098 - Aliphatic polycarboxylic acid metal salt (generic).

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... (CONTINUED) TOXIC SUBSTANCES CONTROL ACT SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.2098 Aliphatic polycarboxylic acid metal salt (generic). (a) Chemical... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Aliphatic polycarboxylic acid...

  20. 40 CFR 721.10606 - Alkyl substituted alkanediol polymer with aliphatic and alicyclic diisocyanates (generic).

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Alkyl substituted alkanediol polymer... alkanediol polymer with aliphatic and alicyclic diisocyanates (generic). (a) Chemical substance and... substituted alkanediol polymer with aliphatic and alicyclic diisocyanates (PMN P-11-486) is subject...

  1. 40 CFR 721.10605 - Polyoxyalkylene ether, polymer with aliphatic diisocyanate, homopolymer, alkanol-blocked (generic).

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Polyoxyalkylene ether, polymer with..., polymer with aliphatic diisocyanate, homopolymer, alkanol-blocked (generic). (a) Chemical substance and... polyoxyalkylene ether, polymer with aliphatic diisocyanate, homopolymer, alkanol-blocked (PMN P-11-485) is...

  2. 40 CFR 721.10605 - Polyoxyalkylene ether, polymer with aliphatic diisocyanate, homopolymer, alkanol-blocked (generic).

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Polyoxyalkylene ether, polymer with..., polymer with aliphatic diisocyanate, homopolymer, alkanol-blocked (generic). (a) Chemical substance and... polyoxyalkylene ether, polymer with aliphatic diisocyanate, homopolymer, alkanol-blocked (PMN P-11-485) is...

  3. 40 CFR 721.10606 - Alkyl substituted alkanediol polymer with aliphatic and alicyclic diisocyanates (generic).

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Alkyl substituted alkanediol polymer... alkanediol polymer with aliphatic and alicyclic diisocyanates (generic). (a) Chemical substance and... substituted alkanediol polymer with aliphatic and alicyclic diisocyanates (PMN P-11-486) is subject...

  4. Preferences in removal of aliphatic and aromatic gasoline components by biofiltration under varied loading.

    PubMed

    Halecky, Martin; Paca, Jan; Kozliak, Evguenii I

    2012-01-01

    Removal of gasoline vapors from waste air was investigated in a bench-scale perlite biofilter for three aromatic-to-aliphatic mass ratios (62/38, 92/8 and 44/56) under different loads, varied by changing both the substrate inlet concentration and air flow rate. The measurement of concentration profiles along the bed height allowed for an assessment of interactions between the aromatic and aliphatic fractions of gasoline. Variations in both the inlet concentrations and empty bed residence time significantly influenced the removal of aliphatic gasoline components. Except for the lowest organic loads, the whole biofilter bed was required for achieving an acceptable removal efficiency of aliphatic hydrocarbons. The presence of large amounts of aromatics negatively impacted the removal of aliphatics. By contrast, the aromatic gasoline components were near-completely removed from any mixtures; the bulk of them were degraded in the first (out of three) biofilter section, even at high concentrations of aliphatic hydrocarbons. The observed effect was shown to be due to competitive interactions of aliphatic and aromatic components, which is consistent with the biological steps being rate limiting. Mass transfer, particularly for aliphatic components due to their high Henry's law constants, was shown to be rate-limiting under extreme scenarios, such as low loading rates and EBRT. PMID:22486669

  5. 40 CFR 721.2098 - Aliphatic polycarboxylic acid metal salt (generic).

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... salt (generic). 721.2098 Section 721.2098 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY... Specific Chemical Substances § 721.2098 Aliphatic polycarboxylic acid metal salt (generic). (a) Chemical... as an aliphatic polycarboxylic acid metal salt (PMN P-01-7) is subject to reporting under...

  6. 40 CFR 721.2098 - Aliphatic polycarboxylic acid metal salt (generic).

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... salt (generic). 721.2098 Section 721.2098 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY... Specific Chemical Substances § 721.2098 Aliphatic polycarboxylic acid metal salt (generic). (a) Chemical... as an aliphatic polycarboxylic acid metal salt (PMN P-01-7) is subject to reporting under...

  7. 40 CFR 721.2098 - Aliphatic polycarboxylic acid metal salt (generic).

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... salt (generic). 721.2098 Section 721.2098 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY... Specific Chemical Substances § 721.2098 Aliphatic polycarboxylic acid metal salt (generic). (a) Chemical... as an aliphatic polycarboxylic acid metal salt (PMN P-01-7) is subject to reporting under...

  8. 40 CFR 721.2098 - Aliphatic polycarboxylic acid metal salt (generic).

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... salt (generic). 721.2098 Section 721.2098 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY... Specific Chemical Substances § 721.2098 Aliphatic polycarboxylic acid metal salt (generic). (a) Chemical... as an aliphatic polycarboxylic acid metal salt (PMN P-01-7) is subject to reporting under...

  9. Antimicrobial activity of phenolics and glucosinolate hydrolysis products and their synergy with streptomycin against pathogenic bacteria.

    PubMed

    Saavedra, Maria J; Borges, Anabela; Dias, Carla; Aires, Alfredo; Bennett, Richard N; Rosa, Eduardo S; Simões, Manuel

    2010-05-01

    The purpose of the present study was to evaluate the in vitro antibacterial effects of different classes of important and common dietary phytochemicals (5 simple phenolics - tyrosol, gallic acid, caffeic acid, ferulic acid, and chlorogenic acid; chalcone - phloridzin; flavan-3-ol - (-) epicatechin; seco-iridoid - oleuropein glucoside; 3 glucosinolate hydrolysis products - allylisothiocyanate, benzylisothiocyanate and 2-phenylethylisothiocyanate) against Escherichia coli, Pseudomonas aeruginosa, Listeria monocytogenes and Staphylococcus aureus. Another objective of this study was to evaluate the effects of dual combinations of streptomycin with the different phytochemicals on antibacterial activity. A disc diffusion assay was used to evaluate the antibacterial activity of the phytochemicals and 3 standard antibiotics (ciprofloxacin, gentamicin and streptomycin) against the four bacteria. The antimicrobial activity of single compounds and dual combinations (streptomycin-phytochemicals) were quantitatively assessed by measuring the inhibitory halos. The results showed that all of the isothiocyanates had significant antimicrobial activities, while the phenolics were much less efficient. No antimicrobial activity was observed with phloridzin. In general P. aeruginosa was the most sensitive microorganism and L. monocytogenes the most resistant. The application of dual combinations demonstrated synergy between streptomycin and gallic acid, ferulic acid, chlorogenic acid, allylisothiocyanate and 2-phenylethylisothiocyanate against the Gram-negative bacteria. In conclusion, phytochemical products and more specifically the isothiocyanates were effective inhibitors of the in vitro growth of the Gram-negative and Gram-positive pathogenic bacteria. Moreover, they can act synergistically with less efficient antibiotics to control bacterial growth. PMID:20632977

  10. A statistical approach to the interpretation of aliphatic hydrocarbon distributions in marine sediments

    USGS Publications Warehouse

    Rapp, J.B.

    1991-01-01

    Q-mode factor analysis was used to quantitate the distribution of the major aliphatic hydrocarbon (n-alkanes, pristane, phytane) systems in sediments from a variety of marine environments. The compositions of the pure end members of the systems were obtained from factor scores and the distribution of the systems within each sample was obtained from factor loadings. All the data, from the diverse environments sampled (estuarine (San Francisco Bay), fresh-water (San Francisco Peninsula), polar-marine (Antarctica) and geothermal-marine (Gorda Ridge) sediments), were reduced to three major systems: a terrestrial system (mostly high molecular weight aliphatics with odd-numbered-carbon predominance), a mature system (mostly low molecular weight aliphatics without predominance) and a system containing mostly high molecular weight aliphatics with even-numbered-carbon predominance. With this statistical approach, it is possible to assign the percentage contribution from various sources to the observed distribution of aliphatic hydrocarbons in each sediment sample. ?? 1991.

  11. Feasibility study on the use of visible-near-infrared spectroscopy for the screening of individual and total glucosinolate contents in broccoli.

    PubMed

    Hernández-Hierro, José Miguel; Valverde, Juan; Villacreces, Salvador; Reilly, Kim; Gaffney, Michael; González-Miret, Maria Lourdes; Heredia, Francisco José; Downey, Gerard

    2012-08-01

    The potential of visible-near-infrared spectroscopy to determine selected individual and total glucosinolates in broccoli has been evaluated. Modified partial least-squares regression was used to develop quantitative models to predict glucosinolate contents. Both the whole spectrum and different spectral regions were separately evaluated to develop the quantitative models; in all cases the best results were obtained using the near-infrared zone between 2000 and 2498 nm. These models have been externally validated for the screening of glucoraphanin, glucobrassicin, 4-methoxyglucobrassicin, neoglucobrassicin, and total glucosinolates contents. In addition, discriminant partial least-squares was used to distinguish between two possible broccoli cultivars and showed a high degree of accuracy. In the case of the qualitative analysis, best results were obtained using the whole spectrum (i.e., 400-2498 nm) with a correct classification rate of 100% in external validation being obtained. PMID:22780224

  12. Mass spectrometry study of the sublimation of aliphatic dipeptides

    NASA Astrophysics Data System (ADS)

    Badelin, V. G.; Tyunina, E. Yu.; Krasnov, A. V.; Tyunina, V. V.; Giricheva, N. I.; Girichev, A. V.

    2012-03-01

    The sublimation of glycyl-L-α-alanine (Gly-Ala), L-α-alanyl-L-α-alanine (Ala-Ala), and DL-α-alanyl-DL-α-valine (Ala-Val) aliphatic dipeptides is studied by electron ionization mass spectrometry in combination with Knudsen effusion. The temperature range in which substances sublime as monomer molecular forms is determined. Enthalpies of sublimation Δs H°( T) are determined for Gly-Ala, Ala-Ala, and Ala-Val. It is shown that the enthalpy of sublimation of dipeptides increases with an increase in the side hydrocarbon radical. The unknown Δs H°(298) values for 17 amino acids and nine dipeptides are estimated using the proposed "structure-property" correlation model, in which the geometry and electron characteristics of molecules are used as structural descriptors.

  13. Aqueous infrared carboxylate absorbances: Aliphatic di-acids

    USGS Publications Warehouse

    Cabaniss, S.E.; Leenheer, J.A.; McVey, I.F.

    1998-01-01

    Aqueous attenuated total reflectance Fourier transform infrared (ATR-FTIR) spectra of 18 aliphatic di-carboxylic acids are reported as a function of pH. The spectra show isosbestic points and intensity changes which indicate that Beer's law is obeyed, and peak frequencies lie within previously reported ranges for aqueous carboxylates and pure carboxylic acids. Intensity sharing from the symmetric carboxylate stretch is evident in many cases, so that bands which are nominally due to alkyl groups show increased intensity at higher pH. The asymmetric stretch of the HA- species is linearly related to the microscopic acidity constant of the H2A species, with ??pK 2 intervening atoms). The results suggest that aqueous ATR-FTIR may be able to estimate 'intrinsic' pKa values of carboxylic acids, in addition to providing quantitative estimates of ionization. ?? 1998 Elsevier Science B.V. All rights reserved.

  14. Sodium hypochlorite oxidation of petroleum aliphatic contaminants in calcareous soils.

    PubMed

    Picard, François; Chaouki, Jamal

    2016-02-01

    This research project investigated the sodium hypochlorite (NaClO) oxidation of aliphatic petroleum contaminants (C10-C50) in a calcareous soil (average 5473 ppm C10-C50, 15 wt% Ca), which had been excavated from a contaminated industrial site. The decontamination objective was to lower the C10-C50 concentration to 700 ppm. CO2 acidity was used in the project to boost the NaClO oxidation yield and seems to have played a role in desorbing the natural organic matter. The experimental conditions were a 2- to 16-h reaction time, at room temperature, with a 1 to 12.5 wt% NaClO oxidative solution and a fixed 2:1 solution-to-soil ratio. With a 3 wt% NaClO solution and with a CO2 overhead, the NaClO dosage requirement was maintained below 60 g NaClO/g of oxidized C10-C50 over the entire decontamination range. The strong chlorine smell remaining after the reaction was completed suggests that part of the NaClO requirement can be recycled. Except traces of chloroform, there were no regulation-listed organochloride contaminants detected on either the treated soil samples or leachates and the total count of chlorinated compounds in treated soil samples was below the detection limit of 250 mg/kg. The NaClO oxidation mechanism on aliphatic substrates might be triggered by transition metals, such as manganese, but no attempt has been made to investigate the oxidation mechanism. Further investigations would include a constant-fed NaClO system and other techniques to lower the required NaClO dosage. PMID:26702553

  15. Identification of Proteins Possibly Involved in Glucosinolate Metabolism in L. agilis R16 and E. coli VL8.

    PubMed

    Luang-In, Vijitra; Narbad, Arjan; Cebeci, Fatma; Bennett, Mark; Rossiter, John T

    2015-04-01

    This study was aimed to identify sinigrin-induced bacterial proteins potentially involved in the metabolism of glucosinolate in two glucosinolate-metabolising bacteria Lactobacillus agilis R16 and Escherichia coli VL8. Sinigrin (2 mM) was used to induce the proteins in both bacteria under anaerobic incubation for 8 h at 30 °C for L. agilis R16 and 37 °C for E. coli VL8 and the controls without sinigrin were performed. Allyl isothiocyanate and allyl nitrile as two degradation products of sinigrin were detected in sinigrin-induced cultures of L. agilis R16 (27% total products) and E. coli VL8 (38% total products) from a complete sinigrin degradation in 8 h for both bacteria. 2D gel electrophoresis was conducted to identify induced proteins with at least twofold increased abundance. Sinigrin-induced L. agilis R16 and the control produced 1561 and 1543 protein spots, respectively. For E. coli VL8, 1363 spots were detected in sinigrin-induced and 1354 spots in the control. A combination of distinct proteins and upregulated proteins of 32 and 35 spots in L. agilis R16 and E. coli VL8, respectively were detected upon sinigrin induction. Of these, 12 and 16 spots from each bacterium respectively were identified by LC-MS/MS. In both bacteria most of the identified proteins are involved in carbohydrate metabolism, oxidoreduction system and sugar transport while the minority belong to purine metabolism, hydrolysis, and proteolysis. This indicated that sinigrin induction led to the expressions of proteins with similar functions in both bacteria and these proteins may play a role in bacterial glucosinolate metabolism. PMID:25805049

  16. Proposed Criteria for Assessing the Efficacy of Cancer Reduction by Plant Foods Enriched in Carotenoids, Glucosinolates, Polyphenols and Selenocompounds

    PubMed Central

    FINLEY, JOHN W.

    2005-01-01

    • Background and Aims The cancer-protective properties of vegetable consumption are most likely mediated through ‘bioactive compounds’ that induce a variety of physiologic functions including acting as direct or indirect antioxidants, regulating enzymes and controlling apoptosis and the cell cycle. The ‘functional food’ industry has produced and marketed foods enriched with bioactive compounds, but there are no universally accepted criteria for judging efficacy of the compounds or enriched foods. • Scope Carotenoids, glucosinolates, polyphenols and selenocompounds are families of bioactive compounds common to vegetables. Although numerous studies have investigated the agricultural and human health implications of enriching foods with one or more of these compounds, inadequate chemical identification of compounds, lack of relevant endpoints and inconsistencies in mechanistic hypotheses and experimental methodologies leave many critical gaps in our understanding of the benefits of such compounds. This review proposes a decision-making process for determining whether there is reasonable evidence of efficacy for the both the compound and the enriched food. These criteria have been used to judge the evidence of efficacy for cancer prevention by carotenoids, polyphenols, glucosinolates and selenocompounds. • Conclusions The evidence of efficacy is weak for carotenoids and polyphenols; the evidence is stronger for glucosinolates and lycopene, but production of enriched foods still is premature. Additionally there is unacceptable variability in the amount and chemical form of these compounds in plants. The evidence of efficacy for selenocompounds is strong, but the clinical study that is potentially the most convincing is still in progress; also the variability in amount and chemical form of Se in plants is a problem. These gaps in understanding bioactive compounds and their health benefits should not serve to reduce research interest but should, instead

  17. 26 CFR 5c.168(f)(8)-5 - Term of lease.

    Code of Federal Regulations, 2010 CFR

    2010-04-01

    ... 26 Internal Revenue 14 2010-04-01 2010-04-01 false Term of lease. 5c.168(f)(8)-5 Section 5c.168(f... Term of lease. (a) Term of lease—Basic rules. To qualify as a lease under section 168(f)(8) and § 5c.168 (f)(8)-1 (a), the lease agreement must provide for a term that does not exceed the maximum...

  18. New insight on aliphatic linkages in the macromolecular organic fraction of Orgueil and Murchison meteorites through ruthenium tetroxide oxidation

    NASA Astrophysics Data System (ADS)

    Remusat, Laurent; Derenne, Sylvie; Robert, François

    2005-09-01

    Ruthenium tetroxide oxidation was used to examine the macromolecular insoluble organic matter (IOM) from the Orgueil and Murchison meteorites and especially to characterize the aliphatic linkages. Already applied to various terrestrial samples, ruthenium tetroxide is a selective oxidant which destroys aromatic units, converting them into CO 2, and yields aliphatic and aromatic acids. In our experiment on chondritic IOM, it produces mainly short aliphatic diacids and polycarboxylic aromatic acids. Some short hydroxyacids are also detected. Aliphatic diacids are interpreted as aliphatic bridges between aromatic units in the chemical structure, and polycarboxylic aromatic acids are the result of the fusion of polyaromatic units. The product distribution shows that aliphatic links are short with numerous substitutions. No indigenous monocarboxylic acid was detected, showing that free aliphatic chains must be very short (less than three carbon atoms). The hydroxyacids are related to the occurrence of ester and ether functional groups within the aliphatic bridges between the aromatic units. This technique thus allows us to characterize in detail the aliphatic linkages of the IOMs, and the derived conclusions are in agreement with spectroscopic, pyrolytic, and degradative results previously reported. Compared to terrestrial samples, the aliphatic part of chondritic IOM is shorter and highly substituted. Aromatic units are smaller and more cross-linked than in coals, as already proposed from NMR data. Orgueil and Murchison IOM exhibit some tiny differences, especially in the length of aliphatic chains.

  19. Structures and energies of coadsorbed CO and H2 on Fe5C2(001), Fe5C2(110), and Fe5C2(100).

    PubMed

    Cao, Dong-Bo; Zhang, Fu-Qiang; Li, Yong-Wang; Wang, Jianguo; Jiao, Haijun

    2005-06-01

    Density functional theory calculations have been carried out on the CO/H2 coadsorption on the (001), (110), and (100) surfaces of Fe5C2 for the understanding of the Fischer-Tropsch synthesis (FTS) mechanism. The stable surface species changes with the variation of the H2 and CO coverage. Along with dissociated hydrogen and adsorbed CO in 2-, 3-, and 4-fold configurations, methylidyne (C(s)H) (C(s), surface carbon), ketenylidene (C(s)CO), ketenyl (C(s)HCO), ketene (C(s)H2CO), and carbon suboxide (C(s)C2O2) are computed as thermodynamically stable surface species on Fe5C2(001) and Fe5C2(110) containing both surface iron and carbon atoms. These surface carbon species can be considered as the preliminary stages for FTS. On Fe5C2(100) with only iron atoms on the surface layer, the stable surface species is dissociated hydrogen and CO with top and 2-fold configurations. The bonding nature of these adsorbed carbon species has been analyzed. PMID:16852330

  20. Glucosinolate-derived isothiocyanates impact mitochondrial function in fungal cells and elicit an oxidative stress response necessary for growth recovery

    PubMed Central

    Calmes, Benoit; N’Guyen, Guillaume; Dumur, Jérome; Brisach, Carlos A.; Campion, Claire; Iacomi, Béatrice; Pigné, Sandrine; Dias, Eva; Macherel, David; Guillemette, Thomas; Simoneau, Philippe

    2015-01-01

    Glucosinolates are brassicaceous secondary metabolites that have long been considered as chemical shields against pathogen invasion. Isothiocyanates (ITCs), are glucosinolate-breakdown products that have negative effects on the growth of various fungal species. We explored the mechanism by which ITCs could cause fungal cell death using Alternaria brassicicola, a specialist Brassica pathogens, as model organism. Exposure of the fungus to ICTs led to a decreased oxygen consumption rate, intracellular accumulation of reactive oxygen species (ROS) and mitochondrial-membrane depolarization. We also found that two major regulators of the response to oxidative stress, i.e., the MAP kinase AbHog1 and the transcription factor AbAP1, were activated in the presence of ICTs. Once activated by ICT-derived ROS, AbAP1 was found to promote the expression of different oxidative-response genes. This response might play a significant role in the protection of the fungus against ICTs as mutants deficient in AbHog1 or AbAP1 were found to be hypersensitive to these metabolites. Moreover, the loss of these genes was accompanied by a significant decrease in aggressiveness on Brassica. We suggest that the robust protection response against ICT-derived oxidative stress might be a key adaptation mechanism for successful infection of host plants by Brassicaceae-specialist necrotrophs like A. brassicicola. PMID:26089832

  1. Profiles of Glucosinolates, Their Hydrolysis Products, and Quinone Reductase Inducing Activity from 39 Arugula (Eruca sativa Mill.) Accessions.

    PubMed

    Ku, Kang-Mo; Kim, Moo Jung; Jeffery, Elizabeth H; Kang, Young-Hwa; Juvik, John A

    2016-08-31

    Glucosinolates, their hydrolysis product concentrations, and the quinone reductase (QR) inducing activity of extracts of leaf tissue were assayed from 39 arugula (Eruca sativa Mill.) accessions. Arugula accessions from Mediterranean countries (n = 16; Egypt, Greece, Italy, Libya, Spain, and Turkey) and Northern Europe (n = 2; Poland and United Kingdom) were higher in glucosinolates and their hydrolysis products, especially glucoraphanin and sulforaphane, compared to those from Asia (n = 13; China, India, and Pakistan) and Middle East Asia (n = 8; Afghanistan, Iran, and Israel). The QR inducing activity was also the highest in Mediterranean and Northern European arugula accessions, possibly due to a significant positive correlation between sulforaphane and QR inducing activity (r = 0.54). No nitrile hydrolysis products were found, suggesting very low or no epithiospecifier protein activity from these arugula accessions. Broad sense heritability (H(2)) was estimated to be 0.91-0.98 for glucoinolates, 0.55-0.83 for their hydrolysis products, and 0.90 for QR inducing activity. PMID:27523193

  2. From Amino Acid to Glucosinolate Biosynthesis: Protein Sequence Changes in the Evolution of Methylthioalkylmalate Synthase in Arabidopsis[W][OA

    PubMed Central

    de Kraker, Jan-Willem; Gershenzon, Jonathan

    2011-01-01

    Methylthioalkylmalate synthase (MAM) catalyzes the committed step in the side chain elongation of Met, yielding important precursors for glucosinolate biosynthesis in Arabidopsis thaliana and other Brassicaceae species. MAM is believed to have evolved from isopropylmalate synthase (IPMS), an enzyme involved in Leu biosynthesis, based on phylogenetic analyses and an overlap of catalytic abilities. Here, we investigated the changes in protein structure that have occurred during the recruitment of IPMS from amino acid to glucosinolate metabolism. The major sequence difference between IPMS and MAM is the absence of 120 amino acids at the C-terminal end of MAM that constitute a regulatory domain for Leu-mediated feedback inhibition. Truncation of this domain in Arabidopsis IPMS2 results in loss of Leu feedback inhibition and quaternary structure, two features common to MAM enzymes, plus an 8.4-fold increase in the kcat/Km for a MAM substrate. Additional exchange of two amino acids in the active site resulted in a MAM-like enzyme that had little residual IPMS activity. Hence, combination of the loss of the regulatory domain and a few additional amino acid exchanges can explain the evolution of MAM from IPMS during its recruitment from primary to secondary metabolism. PMID:21205930

  3. Determination of volatile glucosinolate degradation products in seed coat, stem and in vitro cultures of Moringa peregrina (Forssk.) Fiori.

    PubMed

    Dehshahri, S; Afsharypuor, S; Asghari, G; Mohagheghzadeh, A

    2012-01-01

    Moringaceae, a monogeneric family in Capparales (glucosinolate-containing species), includes 14 species. One of them is Moringa peregrina (Forssk.) Fiori., a small tree, which grows in south east of Iran. Volatile constituents of seed coat and stem of M. peregrina were determined by GC and GC/MS. Moreover, extracts of seed and different cultured cells were analyzed by TLC and GC. Three volatile isothiocyanates including isopropyl isothiocyanate (4.2%), sec-butyl isothiocyanate (< 0.1%) and isobutyl isothiocyanate (92.9%) were found in the volatile oil of the stem , while only two volatile isothiocyanates namely isopropyl isothiocyanate (7.0%) and isobutyl isothiocyanate (51.5%) were determined in the seed coat of the tree. For the first time, the callus and suspension cultures of M. peregrina were initiated and established successfully on Murashige and Skoog medium, containing plant growth hormones. Different precursors and elicitors were fed to the cultures to induce glucosinolates production. This is the first report of in vitro culture production of M. peregrina. There was no production of volatile isothiocyanates in M. peregrina callus and suspension cultures with different treatments. PMID:23181080

  4. Mutation of the Glucosinolate Biosynthesis Enzyme Cytochrome P450 83A1 Monooxygenase Increases Camalexin Accumulation and Powdery Mildew Resistance

    PubMed Central

    Liu, Simu; Bartnikas, Lisa M.; Volko, Sigrid M.; Ausubel, Frederick M.; Tang, Dingzhong

    2016-01-01

    Small secondary metabolites, including glucosinolates and the major phytoalexin camalexin, play important roles in immunity in Arabidopsis thaliana. We isolated an Arabidopsis mutant with increased resistance to the powdery mildew fungus Golovinomyces cichoracearum and identified a mutation in the gene encoding cytochrome P450 83A1 monooxygenase (CYP83A1), which functions in glucosinolate biosynthesis. The cyp83a1-3 mutant exhibited enhanced defense responses to G. cichoracearum and double mutant analysis showed that this enhanced resistance requires NPR1, EDS1, and PAD4, but not SID2 or EDS5. In cyp83a1-3 mutants, the expression of genes related to camalexin synthesis increased upon G. cichoracearum infection. Significantly, the cyp83a1-3 mutant also accumulated higher levels of camalexin. Decreasing camalexin levels by mutation of the camalexin synthetase gene PAD3 or the camalexin synthesis regulator AtWRKY33 compromised the powdery mildew resistance in these mutants. Consistent with these observations, overexpression of PAD3 increased camalexin levels and enhanced resistance to G. cichoracearum. Taken together, our data indicate that accumulation of higher levels of camalexin contributes to increased resistance to powdery mildew. PMID:26973671

  5. The glucosinolate breakdown product indole-3-carbinol acts as an auxin antagonist in roots of Arabidopsis thaliana.

    PubMed

    Katz, Ella; Nisani, Sophia; Yadav, Brijesh S; Woldemariam, Melkamu G; Shai, Ben; Obolski, Uri; Ehrlich, Marcelo; Shani, Eilon; Jander, Georg; Chamovitz, Daniel A

    2015-05-01

    The glucosinolate breakdown product indole-3-carbinol functions in cruciferous vegetables as a protective agent against foraging insects. While the toxic and deterrent effects of glucosinolate breakdown on herbivores and pathogens have been studied extensively, the secondary responses that are induced in the plant by indole-3-carbinol remain relatively uninvestigated. Here we examined the hypothesis that indole-3-carbinol plays a role in influencing plant growth and development by manipulating auxin signaling. We show that indole-3-carbinol rapidly and reversibly inhibits root elongation in a dose-dependent manner, and that this inhibition is accompanied by a loss of auxin activity in the root meristem. A direct interaction between indole-3-carbinol and the auxin perception machinery was suggested, as application of indole-3-carbinol rescues auxin-induced root phenotypes. In vitro and yeast-based protein interaction studies showed that indole-3-carbinol perturbs the auxin-dependent interaction of Transport Inhibitor Response (TIR1) with auxin/3-indoleacetic acid (Aux/IAAs) proteins, further supporting the possibility that indole-3-carbinol acts as an auxin antagonist. The results indicate that chemicals whose production is induced by herbivory, such as indole-3-carbinol, function not only to repel herbivores, but also as signaling molecules that directly compete with auxin to fine tune plant growth and development. PMID:25758811

  6. Germination stimulants of Phelipanche ramosa in the rhizosphere of Brassica napus are derived from the glucosinolate pathway.

    PubMed

    Auger, Bathilde; Pouvreau, Jean-Bernard; Pouponneau, Karinne; Yoneyama, Kaori; Montiel, Grégory; Le Bizec, Bruno; Yoneyama, Koichi; Delavault, Philippe; Delourme, Régine; Simier, Philippe

    2012-07-01

    Phelipanche ramosa is a major parasitic weed of Brassica napus. The first step in a host-parasitic plant interaction is stimulation of parasite seed germination by compounds released from host roots. However, germination stimulants produced by B. napus have not been identified yet. In this study, we characterized the germination stimulants that accumulate in B. napus roots and are released into the rhizosphere. Eight glucosinolate-breakdown products were identified and quantified in B. napus roots by gas chromatography-mass spectrometry. Two (3-phenylpropanenitrile and 2-phenylethyl isothiocyanate [2-PEITC]) were identified in the B. napus rhizosphere. Among glucosinolate-breakdown products, P. ramosa germination was strongly and specifically triggered by isothiocyanates, indicating that 2-PEITC, in particular, plays a key role in the B. napus-P. ramosa interaction. Known strigolactones were not detected by ultraperformance liquid chromatography-tandem mass spectrometry, and seed of Phelipanche and Orobanche spp. that respond to strigolactones but not to isothiocyanates did not germinate in the rhizosphere of B. napus. Furthermore, both wild-type and strigolactone biosynthesis mutants of Arabidopsis thaliana Atccd7 and Atccd8 induced similar levels of P. ramosa seed germination, suggesting that compounds other than strigolactone function as germination stimulants for P. ramosa in other Brassicaceae spp. Our results open perspectives on the high adaptation potential of root-parasitic plants under host-driven selection pressures. PMID:22414435

  7. In vitro antiproliferative activity of isothiocyanates and nitriles generated by myrosinase-mediated hydrolysis of glucosinolates from seeds of cruciferous vegetables.

    PubMed

    Nastruzzi, C; Cortesi, R; Esposito, E; Menegatti, E; Leoni, O; Iori, R; Palmieri, S

    2000-08-01

    A comparison of the effect of isothiocyanates and nitriles derived from some glucosinolates, namely, epi-progoitrin, sinalbin, glucotropaeolin, glucocheirolin, and glucoraphenin, on human erythroleukemic in vitro cultured cells was studied. Many studies have in fact evidenced that a consumption of vegetable containing glucosinolates could reduce the development of colorectal cancer. In the experimental conditions used, the production of isothiocyanates and nitriles from glucosinolates is almost quantitative as confirmed by HPLC or GC-MS analysis. The obtained results demonstrated that in general nitriles are considerably less potent than the corresponding isothiocyanates in inhibiting cancer cell growth. Particularly, the isothiocyanates inhibitory activity on K562 cells growth is higher in the case of products derived from epi-progoitrin, glucotropaeolin, glucoraphenin, and glucocheirolin; while for nitriles the higher activity in inhibiting K562 cells growth is showed by sinalbin-derived product. Considering the antiproliferative activity found for isothiocyanates and nitriles, further studies will be aimed to the possible application of glucosinolate-derived products as chemopreventive cancer agents for the reduction of colorectal cancer. PMID:10956152

  8. Assessing the anticancer compounds Se-methylselenocysteine and glucosinolates in Se-biofortified broccoli (brassica oleracea L. var. italica) sprouts and florets

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Broccoli (Brassica oleracea L. var. italica) is a rich source of chemopreventive compounds. Here, we evaluated and compared the effect of selenium (Se) treatment on the accumulation of anticancer compound Se-methylselenocysteine (SeMSCys) and glucosinolates in broccoli sprouts and florets. Total Se ...

  9. Field Evaluations Test Plan for Validation of Alternatives to Aliphatic Isocyanate Polyurethanes

    NASA Technical Reports Server (NTRS)

    Lewis, Pattie

    2005-01-01

    The objective of this project is to qualify candidate alternatives to Aliphatic Isocyanate Polyurethane coatings under the specifications for the standard system. This project will compare coating performance of the proposed alternatives to existing coating systems or standards.

  10. Project Summary. IN-SITU AQUIFER RESTORATION OF CHLORINATED ALIPHATICS BY METHANOTROPHIC BACTERIA

    EPA Science Inventory

    This project evaluated the potential of an innovative approach to aquifer restoration: enhanced in-situ biotransformation of chlorinated aliphatic solvents by a bacterial community grown on methane under aerobic conditions. The target chlorinated compounds were trichloroethene (...

  11. ANAEROBIC TRANSFORMATION OF CHLORINATED ALIPHATIC HYDROCARBONS IN A SAND AQUIFER BASED ON SPATIAL CHEMICAL DISTRIBUTIONS

    EPA Science Inventory

    We estimated the distribution of chlorinated aliphatic hydrocarbons (CAHs) from groundwater samples collected along three transects in a sand aquifer. richloroethylene (TCE) leaked and contaminated the aquifer probably more than a decade before we collected the measurements. he d...

  12. CHEMICAL DISTRIBUTION AND ANAEROBIC TRANSFORMATION OF CHLORINATED ALIPHATIC HYDROCARBONS IN A SAND AQUIFER

    EPA Science Inventory

    We estimated the distribution of chlorinated aliphatic hydrocarbons (CAHS) from groundwater samples collected along three transects in a sand aquifer. richloroethylene (TCE) leaked and contaminated the aquifer probably more than a decade before we collected the measurements. he d...

  13. Process for the synthesis of aliphatic alcohol-containing mixtures

    DOEpatents

    Greene, M.I.; Gelbein, A.P.

    1984-10-16

    A process for the synthesis of mixtures which include saturated aliphatic alcohols is disclosed. In the first step of the process, the first catalyst activation stage, a catalyst, which comprises the oxides of copper, zinc, aluminum, potassium and one or two additional metals selected from the group consisting of chromium, magnesium, cerium, cobalt, thorium and lanthanum, is partially activated. In this step, a reducing gas stream, which includes hydrogen and at least one inert gas, flows past the catalyst at a space velocity of up to 5,000 liters (STP) per hour, per kilogram of catalyst. The partially activated catalyst is then subjected to the second step of the process, second-stage catalyst activation. In this step, the catalyst is contacted by an activation gas stream comprising hydrogen and carbon monoxide present in a volume ratio of 0.5:1 and 4:1, respectively, at a temperature of 200 to 450 C and a pressure of between 35 and 200 atmospheres. The activation gas flows at a space velocity of from 1,000 to 20,000 liters (STP) per hour, per kilogram of catalyst. Second-stage activation continues until the catalyst is contacted with at least 500,000 liters (STP) of activation gas per kilogram of catalyst. The fully activated catalyst, in the third step of the process, contacts a synthesis gas stream comprising hydrogen and carbon monoxide.

  14. Process for the synthesis of aliphatic alcohol-containing mixtures

    DOEpatents

    Greene, Marvin I.; Gelbein, Abraham P.

    1984-01-01

    A process for the synthesis of mixtures which include saturated aliphatic alcohols is disclosed. In the first step of the process, the first catalyst activation stage, a catalyst, which comprises the oxides of copper, zinc, aluminum, potassium and one or two additional metals selected from the group consisting of chromium, magnesium, cerium, cobalt, thorium and lanthanum, is partially activated. In this step, a reducing gas stream, which includes hydrogen and at least one inert gas, flows past the catalyst at a space velocity of up to 5,000 liters (STP) per hour, per kilogram of catalyst. The partially activated catalyst is then subjected to the second step of the process, second-stage catalyst activation. In this step, the catalyst is contacted by an activation gas stream comprising hydrogen and carbon monoxide present in a volume ratio of 0.5:1 and 4:1, respectively, at a temperature of 200.degree. to 450.degree. C. and a pressure of between 35 and 200 atmospheres. The activation gas flows at a space velocity of from 1,000 to 20,000 liters (STP) per hour, per kilogram of catalyst. Second-stage activation continues until the catalyst is contacted with at least 500,000 liters (STP) of activation gas per kilogram of catalyst. The fully activated catalyst, in the third step of the process, contacts a synthesis gas stream comprising hydrogen and carbon monoxide.

  15. Shape memory polymers based on uniform aliphatic urethane networks

    SciTech Connect

    Wilson, T S; Bearinger, J P; Herberg, J L; Marion III, J E; Wright, W J; Evans, C L; Maitland, D J

    2007-01-19

    Aliphatic urethane polymers have been synthesized and characterized, using monomers with high molecular symmetry, in order to form amorphous networks with very uniform supermolecular structures which can be used as photo-thermally actuable shape memory polymers (SMPs). The monomers used include hexamethylene diisocyanate (HDI), trimethylhexamethylenediamine (TMHDI), N,N,N{prime},N{prime}-tetrakis(hydroxypropyl)ethylenediamine (HPED), triethanolamine (TEA), and 1,3-butanediol (BD). The new polymers were characterized by solvent extraction, NMR, XPS, UV/VIS, DSC, DMTA, and tensile testing. The resulting polymers were found to be single phase amorphous networks with very high gel fraction, excellent optical clarity, and extremely sharp single glass transitions in the range of 34 to 153 C. Thermomechanical testing of these materials confirms their excellent shape memory behavior, high recovery force, and low mechanical hysteresis (especially on multiple cycles), effectively behaving as ideal elastomers above T{sub g}. We believe these materials represent a new and potentially important class of SMPs, and should be especially useful in applications such as biomedical microdevices.

  16. Aliphatic hydrocarbons in Great Barrier Reef organisms and environment

    NASA Astrophysics Data System (ADS)

    Coates, M.; Connell, D. W.; Bodero, J.; Miller, G. J.; Back, R.

    1986-07-01

    This investigation was undertaken to assess the chemical nature, occurrence, and possible origin of petroleum hydrocarbons in the Great Barrier Reef ecosystem. Aliphatic hydrocarbons in surface sediments, water, and a suite of seven species from widely separated coral reefs in the Great Barrier Reef area were analysed by gas chromatography, and by gas chromatography coupled with mass spectrometry. The hydrocarbons found were substantially of biogenic origin. The major components were n-pentadecane, n-heptadecane, pristane and mono-alkenes based on heptadecane, and were believed to originate from benthic algae and phytoplankton. There was no evidence to suggest that lipid content had any influence on hydrocarbon content. Hydrocarbons from the organisms and sediments have characteristic composition patterns which would be altered by the presence of petroleum hydrocarbons. An unresolved complex mixture, usually considered indicative of petroleum contamination, was found in greater than trace amounts only in Holothuria (sea cucumber) and Acropora (coral) from the Capricorn Group, and in some sediment samples from the Capricorn Group and Lizard Island area.

  17. KIF5C S176 Phosphorylation Regulates Microtubule Binding and Transport Efficiency in Mammalian Neurons

    PubMed Central

    Padzik, Artur; Deshpande, Prasannakumar; Hollos, Patrik; Franker, Mariella; Rannikko, Emmy H.; Cai, Dawen; Prus, Piotr; Mågård, Mats; Westerlund, Nina; Verhey, Kristen J.; James, Peter; Hoogenraad, Casper C.; Coffey, Eleanor T.

    2016-01-01

    Increased phosphorylation of the KIF5 anterograde motor is associated with impaired axonal transport and neurodegeneration, but paradoxically also with normal transport, though the details are not fully defined. JNK phosphorylates KIF5C on S176 in the motor domain; a site that we show is phosphorylated in brain. Microtubule pelleting assays demonstrate that phosphomimetic KIF5C(1-560)S176D associates weakly with microtubules compared to KIF5C(1-560)WT. Consistent with this, 50% of KIF5C(1-560)S176D shows diffuse movement in neurons. However, the remaining 50% remains microtubule bound and displays decreased pausing and increased bidirectional movement. The same directionality switching is observed with KIF5C(1-560)WT in the presence of an active JNK chimera, MKK7-JNK. Yet, in cargo trafficking assays where peroxisome cargo is bound, KIF5C(1-560)S176D-GFP-FRB transports normally to microtubule plus ends. We also find that JNK increases the ATP hydrolysis of KIF5C in vitro. These data suggest that phosphorylation of KIF5C-S176 primes the motor to either disengage entirely from microtubule tracks as previously observed in response to stress, or to display improved efficiency. The final outcome may depend on cargo load and motor ensembles. PMID:27013971

  18. 26 CFR 5c.103-1 - Leases and capital expenditures.

    Code of Federal Regulations, 2011 CFR

    2011-04-01

    ... 26 Internal Revenue 14 2011-04-01 2010-04-01 true Leases and capital expenditures. 5c.103-1 Section 5c.103-1 Internal Revenue INTERNAL REVENUE SERVICE, DEPARTMENT OF THE TREASURY (CONTINUED) INCOME...-1 Leases and capital expenditures. For purposes of section 103(b)(6)(D) and §...

  19. Silver-Catalyzed Decarboxylative Allylation of Aliphatic Carboxylic Acids in Aqueous Solution.

    PubMed

    Cui, Lei; Chen, He; Liu, Chao; Li, Chaozhong

    2016-05-01

    Direct decarboxylative radical allylation of aliphatic carboxylic acids is described. With K2S2O8 as the oxidant and AgNO3 as the catalyst, the reactions of aliphatic carboxylic acids with allyl sulfones in aqueous CH3CN solution gave the corresponding alkenes in satisfactory yields under mild conditions. This site-specific allylation method is applicable to all primary, secondary, and tertiary alkyl acids and exhibits wide functional group compatibility. PMID:27065060

  20. THE CARRIERS OF THE INTERSTELLAR UNIDENTIFIED INFRARED EMISSION FEATURES: AROMATIC OR ALIPHATIC?

    SciTech Connect

    Li Aigen; Draine, B. T. E-mail: draine@astro.princeton.edu

    2012-12-01

    The unidentified infrared emission (UIE) features at 3.3, 6.2, 7.7, 8.6, and 11.3 {mu}m, commonly attributed to polycyclic aromatic hydrocarbon (PAH) molecules, have been recently ascribed to coal- or kerogen-like organic nanoparticles with a mixed aromatic-aliphatic structure. However, we show in this Letter that this hypothesis is inconsistent with observations. We estimate the aliphatic fraction of the UIE carriers based on the observed intensities of the 3.4 {mu}m and 6.85 {mu}m emission features by attributing them exclusively to aliphatic C-H stretch and aliphatic C-H deformation vibrational modes, respectively. We derive the fraction of carbon atoms in aliphatic form to be <15%. We conclude that the UIE emitters are predominantly aromatic, with aliphatic material at most a minor part of the UIE carriers. The PAH model is consistent with astronomical observations and PAHs dominate the strong UIE bands.

  1. Synthesis of novel naphthoquinone aliphatic amides and esters and their anticancer evaluation.

    PubMed

    Kongkathip, Boonsong; Akkarasamiyo, Sunisa; Hasitapan, Komkrit; Sittikul, Pichamon; Boonyalai, Nonlawat; Kongkathip, Ngampong

    2013-02-01

    Fourteen new naphthoquinone aliphatic amides and seventeen naphthoquinone aliphatic esters were synthesized in nine to ten steps from 1-hydroxy-2-naphthoic acid with 9-25% overall yield for the amides, and 16-21% overall yield for the esters. The key step of the amide synthesis is a coupling reaction between amine and various aliphatic acids using 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMTMM) as a coupling agent while for the ester synthesis, DCC/DMAP or CDI was used as the coupling reagent between aliphatic acids and naphthoquinone alcohol. Both naphthoquinone amides and esters were evaluated for their anticancer activity against KB cells. It was found that naphthoquinone aliphatic amides showed stronger anticancer activity than those of the esters when the chains are longer than 7-carbon atoms. The optimum chain of amides is expected to be 16-carbon atoms. In addition, naphthoquinone aliphatic esters with α-methyl on the ester moiety possessed much stronger anticancer activity than the straight chains. Decatenation assay revealed that naphthoquinone amide with 16-carbon atoms chain at 15 μM and 20 μM can completely inhibit hTopoIIα activity while at 10 μM the enzyme activity was moderately inhibited. Molecular docking result also showed the same trend as the cytotoxicity and decatenation assay. PMID:23313636

  2. A Theoretical Study on the Vibrational Spectra of Polycyclic Aromatic Hydrocarbon Molecules with Aliphatic Sidegroups

    NASA Astrophysics Data System (ADS)

    Sadjadi, SeyedAbdolreza; Zhang, Yong; Kwok, Sun

    2015-03-01

    The role of aliphatic side groups in the formation of astronomical unidentified infrared emission (UIE) features is investigated by applying the density functional theory to a series of molecules with mixed aliphatic-aromatic structures. The effects of introducing various aliphatic groups to a fixed polycyclic aromatic hydrocarbon (PAH) core (ovalene) are studied. Simulated spectra for each molecule are produced by applying a Drude profile at T = 500 K while the molecule is kept at its electronic ground state. The vibrational normal modes are classified using a semi-quantitative method. This allows us to separate the aromatic and aliphatic vibrations, and therefore provides clues to what types of vibrations are responsible for the emissions bands at different wavelengths. We find that many of the UIE bands are not pure aromatic vibrational bands but may represent coupled vibrational modes. The effects of aliphatic groups on the formation of the 8 μm plateau are quantitatively determined. The vibrational motions of methyl (-CH3) and methylene (-CH2 -) groups can cause the merging of the vibrational bands of the parent PAH and the forming of broad features. These results suggest that aliphatic structures can play an important role in the UIE phenomenon.

  3. The UNC5C Netrin Receptor Regulates Dorsal Guidance Of Mouse Hindbrain Axons

    PubMed Central

    Kim, Doyeun; Ackerman, Susan L.

    2011-01-01

    The cerebellum receives its input from multiple precerebellar nuclei located in the brainstem, and sends processed information to other brain structures via the cerebellar deep neurons. Guidance molecules that regulate the complex migrations of precerebellar neurons and the initial guidance of their leading processes have been identified. However, the molecules necessary for dorsal guidance of precerebellar axons to the developing cerebellum, or for guidance of decussating axons of the deep nuclei are not known. To determine whether Unc5c plays a role in the dorsal guidance of precerebellar and deep cerebellar axons, we studied axonal trajectories of these neurons in Unc5c-/- mice. Our results show that Unc5c is expressed broadly in the precerebellar and deep cerebellar neurons. Unc5c deletion disrupted long-range dorsal guidance of inferior olivary and pontine axons after crossing the midline. In addition, dorsal guidance of the axons from the medial deep cerebellar and external cuneate neurons was affected in Unc5c-/- mice, as were anterior migrations of pontine neurons. Coincident with the guidance defects of their axons, degeneration of neurons in external cuneate nucleus and subdivisions of inferior olivary nucleus was observed in Unc5c-/- mice. Lastly, transgenic expression of Unc5c in deep neurons and pontine neurons by the Atoh1 promoter rescued defects of the medial deep cerebellar and pontine axons observed in Unc5c-/- embryos, demonstrating that Unc5c acts cell autonomously in the guidance of these axons. Our results suggest that Unc5c plays a broad role in dorsal guidance of axons in the developing hindbrain. PMID:21307253

  4. Controlled oxidation of aliphatic CH bonds in metallo-monooxygenases: mechanistic insights derived from studies on deuterated and fluorinated hydrocarbons.

    PubMed

    Chen, Yao-Sheng; Luo, Wen-I; Yang, Chung-Ling; Tu, Yi-Jung; Chang, Chun-Wei; Chiang, Chih-Hsiang; Chang, Chi-Yao; Chan, Sunney I; Yu, Steve S-F

    2014-05-01

    The control over the regio- and/or stereo-selective aliphatic CH oxidation by metalloenzymes is of great interest to scientists. Typically, these enzymes invoke host-guest chemistry to sequester the substrates within the protein pockets, exploiting sizes, shapes and specific interactions such as hydrogen-bonding, electrostatic forces and/or van der Waals interactions to control the substrate specificity, regio-specificity and stereo-selectivity. Over the years, we have developed a series of deuterated and fluorinated variants of these hydrocarbon substrates as probes to gain insights into the controlled CH oxidations of hydrocarbons facilitated by these enzymes. In this review, we illustrate the application of these designed probes in the study of three monooxygenases: (i) the particulate methane monooxygenase (pMMO) from Methylococcus capsulatus (Bath), which oxidizes straight-chain C1-C5 alkanes and alkenes to form their corresponding 2-alcohols and epoxides, respectively; (ii) the recombinant alkane hydroxylase (AlkB) from Pseudomonas putida GPo1, which oxidizes the primary CH bonds of C5-C12 linear alkanes; and (iii) the recombinant cytochrome P450 from Bacillus megaterium, which oxidizes C12-C20 fatty acids at the ω-1, ω-2 or ω-3 CH positions. PMID:24629413

  5. Aliphatic polyester block polymers: renewable, degradable, and sustainable.

    PubMed

    Hillmyer, Marc A; Tolman, William B

    2014-08-19

    Nearly all polymers are derived from nonrenewable fossil resources, and their disposal at their end of use presents significant environmental problems. Nonetheless, polymers are ubiquitous, key components in myriad technologies and are simply indispensible for modern society. An important overarching goal in contemporary polymer research is to develop sustainable alternatives to "petro-polymers" that have competitive performance properties and price, are derived from renewable resources, and may be easily and safely recycled or degraded. Aliphatic polyesters are particularly attractive targets that may be prepared in highly controlled fashion by ring-opening polymerization of bioderived lactones. However, property profiles of polyesters derived from single monomers (homopolymers) can limit their applications, thus demanding alternative strategies. One such strategy is to link distinct polymeric segments in an A-B-A fashion, with A and B chosen to be thermodynamically incompatible so that they can self-organize on a nanometer-length scale and adopt morphologies that endow them with tunable properties. For example, such triblock copolymers can be useful as thermoplastic elastomers, in pressure sensitive adhesive formulations, and as toughening modifiers. Inspired by the tremendous utility of petroleum-derived styrenic triblock copolymers, we aimed to develop syntheses and understand the structure-property profiles of sustainable alternatives, focusing on all renewable and all readily degradable aliphatic polyester triblocks as targets. Building upon oxidation chemistry reported more than a century ago, a constituent of the peppermint plant, (-)-menthol, was converted to the ε-caprolactone derivative menthide. Using a diol initiator and controlled catalysis, menthide was polymerized to yield a low glass transition temperature telechelic polymer (PM) that was then further functionalized using the biomass-derived monomer lactide (LA) to yield fully renewable PLA

  6. Pharmacological activities of cilantro's aliphatic aldehydes against Leishmania donovani.

    PubMed

    Donega, Mateus A; Mello, Simone C; Moraes, Rita M; Jain, Surendra K; Tekwani, Babu L; Cantrell, Charles L

    2014-12-01

    Leishmaniasis is a chronic infectious disease caused by different Leishmania species. Global occurrences of this disease are primarily limited to tropical and subtropical regions. Treatments are available; however, patients complain of side effects. Different species of plants have been screened as a potential source of new drugs against leishmaniasis. In this study, we investigated the antileishmanial activity of cilantro (Coriandrum sativum) essential oil and its main components: (E)-2-undecenal, (E)-2-decenal, (E)-2-dodecenal, decanal, dodecanal, and tetradecanal. The essential oil of C. sativum leaves inhibits growth of Leishmani donovani promastigotes in culture with an IC50 of 26.58 ± 6.11 µg/mL. The aliphatic aldehydes (E)-2-decenal (7.85 ± 0.28 µg/mL), (E)-2-undecenal (2.81 ± 0.21 µg/mL), and (E)-2-dodecenal (4.35 ± 0.15 µg/mL), all isolated from C. sativum essential oil, are effective inhibitors of in vitro cultures of L. donovani promastigotes. Aldehydes (E)-2-decenal, (E)-2-undecenal, and (E)-2-dodecenal were also evaluated against axenic amastigotes and IC50 values were determined to be 2.47 ± 0.25 µg/mL, 1.25 ± 0.11 µg/mL, and 4.78 ± 1.12 µg/mL, respectively. (E)-2-Undecenal and (E)-2-dodecenal demonstrated IC50 values of 5.65 ± 0.19 µg/mL and 9.60 ± 0.89 µg/mL, respectively, against macrophage amastigotes. These cilantro compounds showed no cytotoxicity against THP-1 macrophages. PMID:25340465

  7. Mutations in the intellectual disability gene KDM5C reduce protein stability and demethylase activity

    PubMed Central

    Brookes, Emily; Laurent, Benoit; Õunap, Katrin; Carroll, Renee; Moeschler, John B.; Field, Michael; Schwartz, Charles E.; Gecz, Jozef; Shi, Yang

    2015-01-01

    Mutations in KDM5C are an important cause of X-linked intellectual disability in males. KDM5C encodes a histone demethylase, suggesting that alterations in chromatin landscape may contribute to disease. We used primary patient cells and biochemical approaches to investigate the effects of patient mutations on KDM5C expression, stability and catalytic activity. We report and characterize a novel nonsense mutation, c.3223delG (p.V1075Yfs*2), which leads to loss of KDM5C protein. We also characterize two KDM5C missense mutations, c.1439C>T (p.P480L) and c.1204G>T (p.D402Y) that are compatible with protein production, but compromise stability and enzymatic activity. Finally, we demonstrate that a c.2T>C mutation in the translation initiation codon of KDM5C results in translation re-start and production of a N-terminally truncated protein (p.M1_E165del) that is unstable and lacks detectable demethylase activity. Patient fibroblasts do not show global changes in histone methylation but we identify several up-regulated genes, suggesting local changes in chromatin conformation and gene expression. This thorough examination of KDM5C patient mutations demonstrates the utility of examining the molecular consequences of patient mutations on several levels, ranging from enzyme production to catalytic activity, when assessing the functional outcomes of intellectual disability mutations. PMID:25666439

  8. Separation and conductimetric detection of C1-C7 aliphatic monocarboxylic acids and C1-C7 aliphatic monoamines on unfunctionized polymethacrylate resin columns.

    PubMed

    Ohta, Kazutoku; Towata, Atsuya; Ohashi, Masayoshi; Takeuchi, Toyohide

    2004-06-11

    The application of unfunctionized polymethacrylate resin (TSKgel G3000PWXL) as a stationary phase in liquid chromatography with conductimetric detection for C1-C7 aliphatic monocarboxylic acids (formic acid, acetic acid, propionic acid, butyric acid, isovaleric acid, valeric acid, 3,3-dimethylbutyric acid, 4-methylvaleric acid, hexanoic acid, 2-methylhexanoic acid, 5-methylhexanoic acid and heptanoic acid) and C1-C7 aliphatic monoamines (methylamine, ethylamine, propylamine, isobutylamine, butylamine, isoamylamine, amylamine, 1,3-dimethylbutylamine, hexylamine, 2-heptylamine and heptylamine) was attempted with C8 aliphatic monocarboxylic acids (2-propylvaleric acid, 2-ethylhexanoic acid, 2-methylheptanoic acid and octanoic acid) and C8 aliphatic monoamines (1,5-dimethylhexylamine, 2-ethylhexylamine, 1-methylheptylamine and octylamine) as eluents, respectively. Using 1 mM 2-methylheptanoic acid at pH 4.0 as the eluent, excellent separation and relatively high sensitive detection for these C1-C7 carboxylic acids were achieved on a TSKgel G3000PWXL column (150 mm x 6 mm i.d.) in 60 min. Using 2 mM octylamine at pH 11.0 as the eluent, excellent separation and relatively high sensitive detection for these C1-C7 amines were also achieved on the TSKgel G3000PWXL column in 60 min. PMID:15250420

  9. A rare case of cervical facet joint and synovial cyst at C5/C6.

    PubMed

    Phan, Kevin; Mobbs, Ralph J

    2016-07-01

    Lumbar synovial cysts are uncommon, and particularly rare at cervical levels. We report a 40-year-old woman who presented with pain distribution in the typical C6 dermatome. MRI revealed a right-sided large extradural cystic lesion adjacent to the C5/C6 facet joint that was hyperintense on T2-weighted MRI and hypointense on T1-weighted MRI. The patient underwent posterior cervical surgery at the C5/C6 level which involved posterior decompressive unilateral laminotomy and excision of the C5/C6 facet joint cyst. Following complete facetectomy of the right C5/C6 facet joint and exposure of the C6 nerve throughout its foraminal course, instrumented fusion was performed. Following the procedure, the patient had an uneventful recovery with relief of her radicular symptoms at follow-up clinical review. PMID:26916905

  10. Synthesis of NaB5C bulk ceramics by reaction sintering

    NASA Astrophysics Data System (ADS)

    Morito, Haruhiko; Anzai, Jun; Kimura, Takuma; Yamane, Hisanori

    2015-09-01

    Bulk ceramics of NaB5C were prepared by heating compact bodies of amorphous boron (B) and carbon black (C) powders with Na at 1073 K. The obtained bulk ceramics retained the rectangular shape of their original compacts. The obtained samples had a density of 80.1 ± 0.6% of the theoretical density of NaB5C. NaB5C bulk ceramics were also prepared by heating compacts comprised of B and C powders and Na. The addition of Na to the starting compact bodies increased the relative bulk density to 83.5 ± 0.4%. A fracture bending strength of 195 MPa was measured for the NaB5C bulk sample prepared from the compact of Na, B, and C.

  11. Strong ion-exchange centrifugal partition chromatography as an efficient method for the large-scale purification of glucosinolates.

    PubMed

    Toribio, Alix; Nuzillard, Jean-Marc; Renault, Jean-Hugues

    2007-11-01

    The glucosinolates sinalbin and glucoraphanin were purified by strong ion-exchange displacement centrifugal partition chromatography (SIXCPC). The optimized conditions involved the biphasic solvent system ethyl acetate/n-butanol/water (3:2:5, v/v), the lipophilic anion-exchanger Aliquat 336 (trioctylmethylammonium chloride, 160 and 408 mM) and a sodium iodide solution (80 and 272 mM) as displacer. Amounts as high as 2.4 g of sinalbin and 2.6g of glucoraphanin were obtained in one step in 2.5 and 3.5h respectively, starting from 12 and 25 g of mustard and broccoli seed aqueous extracts, using a laboratory scale CPC column (200 mL inner volume). PMID:17904564

  12. Arabidopsis HARMLESS TO OZONE LAYER protein methylates a glucosinolate breakdown product and functions in resistance to Pseudomonas syringae pv. maculicola.

    PubMed

    Nagatoshi, Yukari; Nakamura, Tatsuo

    2009-07-17

    Almost all of the chlorine-containing gas emitted from natural sources is methyl chloride (CH(3)Cl), which contributes to the destruction of the stratospheric ozone layer. Tropical and subtropical plants emit substantial amounts of CH(3)Cl. A gene involved in CH(3)Cl emission from Arabidopsis was previously identified and designated HARMLESS TO OZONE LAYER (hereafter AtHOL1) based on the mutant phenotype. Our previous studies demonstrated that AtHOL1 and its homologs, AtHOL2 and AtHOL3, have S-adenosyl-l-methionine-dependent methyltransferase activities. However, the physiological functions of AtHOLs have yet to be elucidated. In the present study, our comparative kinetic analyses with possible physiological substrates indicated that all of the AtHOLs have low activities toward chloride. AtHOL1 was highly reactive to thiocyanate (NCS(-)), a pseudohalide, synthesizing methylthiocyanate (CH(3)SCN) with a very high k(cat)/K(m) value. We demonstrated in vivo that substantial amounts of NCS(-) were synthesized upon tissue damage in Arabidopsis and that NCS(-) was largely derived from myrosinase-mediated hydrolysis of glucosinolates. Analyses with the T-DNA insertion Arabidopsis mutants (hol1, hol2, and hol3) revealed that only hol1 showed increased sensitivity to NCS(-) in medium and a concomitant lack of CH(3)SCN synthesis upon tissue damage. Bacterial growth assays indicated that the conversion of NCS(-) into CH(3)SCN dramatically increased antibacterial activities against Arabidopsis pathogens that normally invade the wound site. Furthermore, hol1 seedlings showed an increased susceptibility toward an Arabidopsis pathogen, Pseudomonas syringae pv. maculicola. Here we propose that AtHOL1 is involved in glucosinolate metabolism and defense against phytopathogens. Moreover, CH(3)Cl synthesized by AtHOL1 could be considered a byproduct of NCS(-) metabolism. PMID:19419967

  13. PPP2R5C Couples Hepatic Glucose and Lipid Homeostasis

    PubMed Central

    Cheng, Yong-Sheng; Seibert, Oksana; Klöting, Nora; Dietrich, Arne; Straßburger, Katrin; Fernández-Veledo, Sonia; Vendrell, Joan J.; Zorzano, Antonio; Blüher, Matthias; Herzig, Stephan; Berriel Diaz, Mauricio; Teleman, Aurelio A.

    2015-01-01

    In mammals, the liver plays a central role in maintaining carbohydrate and lipid homeostasis by acting both as a major source and a major sink of glucose and lipids. In particular, when dietary carbohydrates are in excess, the liver converts them to lipids via de novo lipogenesis. The molecular checkpoints regulating the balance between carbohydrate and lipid homeostasis, however, are not fully understood. Here we identify PPP2R5C, a regulatory subunit of PP2A, as a novel modulator of liver metabolism in postprandial physiology. Inactivation of PPP2R5C in isolated hepatocytes leads to increased glucose uptake and increased de novo lipogenesis. These phenotypes are reiterated in vivo, where hepatocyte specific PPP2R5C knockdown yields mice with improved systemic glucose tolerance and insulin sensitivity, but elevated circulating triglyceride levels. We show that modulation of PPP2R5C levels leads to alterations in AMPK and SREBP-1 activity. We find that hepatic levels of PPP2R5C are elevated in human diabetic patients, and correlate with obesity and insulin resistance in these subjects. In sum, our data suggest that hepatic PPP2R5C represents an important factor in the functional wiring of energy metabolism and the maintenance of a metabolically healthy state. PMID:26440364

  14. Process for removing halogenated aliphatic and aromatic compounds from petroleum products

    DOEpatents

    Googin, John M.; Napier, John M.; Travaglini, Michael A.

    1983-01-01

    A process for removing halogenated aliphatic and aromatic compounds, e.g., polychlorinated biphenyls, from petroleum products by solvent extraction. The halogenated aliphatic and aromatic compounds are extracted from a petroleum product into a polar solvent by contacting the petroleum product with the polar solvent. The polar solvent is characterized by a high solubility for the extracted halogenated aliphatic and aromatic compounds, a low solubility for the petroleum product and considerable solvent power for polyhydroxy compound. The preferred polar solvent is dimethylformamide. A miscible compound, such as, water or a polyhydroxy compound, is added to the polar extraction solvent to increase the polarity of the polar extraction solvent. The halogenated aliphatic and aromatic compounds are extracted from the highly-polarized mixture of water or polyhydroxy compound and polar extraction solvent into a low polar or nonpolar solvent by contacting the water or polyhydroxy compound-polar solvent mixture with the low polar or nonpolar solvent. The halogenated aliphatic and aromatic compounds and the low polar or nonpolar solvent are separated by physical means, e.g., vacuum evaporation. The polar and nonpolar solvents are recovered from recycling. The process can easily be designed for continuous operation. Advantages of the process include that the polar solvent and a major portion of the nonpolar solvent can be recycled, the petroleum products are reclaimable and the cost for disposing of waste containing polychlorinated biphenyls is significantly reduced.

  15. Process for removing halogenated aliphatic and aromatic compounds from petroleum products

    DOEpatents

    Googin, J.M.; Napier, J.M.; Travaglini, M.A.

    1983-09-20

    A process is described for removing halogenated aliphatic and aromatic compounds, e.g., polychlorinated biphenyls, from petroleum products by solvent extraction. The halogenated aliphatic and aromatic compounds are extracted from a petroleum product into a polar solvent by contacting the petroleum product with the polar solvent. The polar solvent is characterized by a high solubility for the extracted halogenated aliphatic and aromatic compounds, a low solubility for the petroleum product and considerable solvent power for polyhydroxy compound. The preferred polar solvent is dimethylformamide. A miscible compound, such as, water or a polyhydroxy compound, is added to the polar extraction solvent to increase the polarity of the polar extraction solvent. The halogenated aliphatic and aromatic compounds are extracted from the highly-polarized mixture of water or polyhydroxy compound and polar extraction solvent into a low polar or nonpolar solvent by contacting the water or polyhydroxy compound-polar solvent mixture with the low polar or nonpolar solvent. The halogenated aliphatic and aromatic compounds and the low polar or nonpolar solvent are separated by physical means, e.g., vacuum evaporation. The polar and nonpolar solvents are recovered from recycling. The process can easily be designed for continuous operation. Advantages of the process include that the polar solvent and a major portion of the nonpolar solvent can be recycled, the petroleum products are reclaimable and the cost for disposing of waste containing polychlorinated biphenyls is significantly reduced. 1 fig.

  16. Manganese-catalyzed late-stage aliphatic C-H azidation.

    PubMed

    Huang, Xiongyi; Bergsten, Tova M; Groves, John T

    2015-04-29

    We report a manganese-catalyzed aliphatic C-H azidation reaction that can efficiently convert secondary, tertiary, and benzylic C-H bonds to the corresponding azides. The method utilizes aqueous sodium azide solution as the azide source and can be performed under air. Besides its operational simplicity, the potential of this method for late-stage functionalization has been demonstrated by successful azidation of various bioactive molecules with yields up to 74%, including the important drugs pregabalin, memantine, and the antimalarial artemisinin. Azidation of celestolide with a chiral manganese salen catalyst afforded the azide product in 70% ee, representing a Mn-catalyzed enantioselective aliphatic C-H azidation reaction. Considering the versatile roles of organic azides in modern chemistry and the ubiquity of aliphatic C-H bonds in organic molecules, we envision that this Mn-azidation method will find wide application in organic synthesis, drug discovery, and chemical biology. PMID:25871027

  17. Transformations of 1- and 2-carbon halogenated aliphatic organic compounds under methanogenic conditions.

    PubMed Central

    Bouwer, E J; McCarty, P L

    1983-01-01

    Several 1- and 2-carbon halogenated aliphatic organic compounds present at low concentrations (less than 100 micrograms/liter) were degraded under methanogenic conditions in batch bacterial cultures and in a continuous-flow methanogenic fixed-film laboratory-scale column. Greater than 90% degradation was observed within a 2-day detention time under continuous-flow methanogenic conditions with acetate as a primary substrate. Carbon-14 measurements indicated that chloroform, carbon tetrachloride, and 1,2-dichloroethane were almost completely oxidized to carbon dioxide, confirming removal by biooxidation. The initial step in the transformations of tetrachloroethylene and 1,1,2,2-tetrachloroethane to nonchlorinated end products appeared to be reductive dechlorination to trichloroethylene and 1,1,2-trichloroethane, respectively. Transformations of the brominated aliphatic compounds appear to be the result of both biological and chemical processes. The data suggest that transformations of halogenated aliphatic compounds can occur under methanogenic conditions in the environment. PMID:6859849

  18. Aliphatic Hydrocarbons in Surface Sediments of Willapa Bay and Grays Harbor, Washington

    USGS Publications Warehouse

    Rapp, J.B.; Kvenvolden, K.A.; Clifton, H.E.

    1982-01-01

    Willapa Bay and Grays Harbor are two adjacent estuaries along the coast of Washington state. Willapa Bay is a recreational area minimally affected by industry; Grays Harbor, on the other hand, is moderately industrialized. Aliphatic hydrocarbons in surface sediments from these two estuaries reflect the differences in human activities. For example, the mean concentration of aliphatic hydrocarbons for seven stations in Willapa Bay is 1,000 ?g/g (relative to organic carbon) while in Grays Harbor this mean concentration for six stations is 1,900 ?g/g. The difference is attributed mainly to the greater urban and industrial pollution in Grays Harbor. The gas chromatographic records of aliphatic hydrocarbons also reflect the extent of hydrocarbon pollution by the presence of a chromatographically unresolved mixture of hydrocarbons. This kind of mixture is more evident in sediments from Grays Harbor, and in both estuaries it is more concentrated in sediments collected nearest to urban centers.

  19. Seasonal distribution of aliphatic hydrocarbons in the Vaza Barris Estuarine System, Sergipe, Brazil.

    PubMed

    Barbosa, José Carlos S; Santos, Lukas G G V; Sant'Anna, Mércia V S; Souza, Michel R R; Damasceno, Flaviana C; Alexandre, Marcelo R

    2016-03-15

    The seasonal assessment of anthropogenic activities in the Vaza Barris estuarine river system, located in the Sergipe state, northeastern Brazil, was performed using the aliphatic hydrocarbon distribution. The aliphatic hydrocarbon and isoprenoid (Pristane and Phytane) concentrations ranged between 0.19μgg(-1) and 8.5μgg(-1) of dry weight. Data were analyzed using Kruskal-Wallis test, with significance level set at p<0.05, and no seasonality distribution change was observed. The Carbon Preference Index (CPI), associated with n-alkanes/n-C16, Low Molecular Weight/High Molecular Weight ratio (LMW/HMW) and Terrigenous to Aquatic Ratio (TAR) suggested biogenic input of aliphatic hydrocarbons for most samples, with significant contribution of higher plants. PMID:26837270

  20. The effect of aliphatic fuel constituents on the biodegradation of polycyclic aromatic hydrocarbons

    SciTech Connect

    Gamerdinger, A.P.

    1995-12-01

    In petroleum-derived waste, n-alkanes are often codeposited with polycyclic aromatic hydrocarbons (PAHs). The impact of aliphatic fuel constituents on the biodegradation of the more toxic PAHs is considered. Biodegradation of naphthalene by a Coryneform bacteria was examined in biphasic, slurry systems containing and aliphatic solvent in addition to the aqueous phase. The effect of solvent hydrophobicity was evaluated by varying the solvent treatment; a homologous series of n-alkanes was used. Relative to an aqueous system (no solvent), the extent of naphthalene degradation was enhanced in the presence of decane, dodecane, and hexadecane. Biodegradation was apparent, but decreased in the presence of octane, and was completely absent in the presence of hexane. The impact of aliphatic constituents on PAH biodegradation is a function of solvent hydrophobicity. The results indicate that the presence of multiple chemical constituents in complex systems modifies bioavailability and biodegradation.

  1. Enzymatic degradation of aliphatic nitriles by Rhodococcus rhodochrous BX2, a versatile nitrile-degrading bacterium.

    PubMed

    Fang, Shumei; An, Xuejiao; Liu, Hongyuan; Cheng, Yi; Hou, Ning; Feng, Lu; Huang, Xinning; Li, Chunyan

    2015-06-01

    Nitriles are common environmental pollutants, and their removal has attracted increasing attention. Microbial degradation is considered to be the most acceptable method for removal. In this work, we investigated the biodegradation of three aliphatic nitriles (acetonitrile, acrylonitrile and crotononitrile) by Rhodococcus rhodochrous BX2 and the expression of their corresponding metabolic enzymes. This organism can utilize all three aliphatic nitriles as sole carbon and nitrogen sources, resulting in the complete degradation of these compounds. The degradation kinetics were described using a first-order model. The degradation efficiency was ranked according to t1/2 as follows: acetonitrile>trans-crotononitrile>acrylonitrile>cis-crotononitrile. Only ammonia accumulated following the three nitriles degradation, while amides and carboxylic acids were transient and disappeared by the end of the assay. mRNA expression and enzyme activity indicated that the tested aliphatic nitriles were degraded via both the inducible NHase/amidase and the constitutive nitrilase pathways, with the former most likely preferred. PMID:25746475

  2. Classical-Reaction-Driven Stereo- and Regioselective C(sp(3) )-H Functionalization of Aliphatic Amines.

    PubMed

    Mahato, Sujit; Jana, Chandan K

    2016-06-01

    A large variety of synthetic methods have been developed for the synthesis of functionalized aliphatic amines because of their broad spectrum of application. Metallic reagents/catalysts and/or toxic oxidants are involved in most of the cases. Direct CH functionalization of aliphatic amines via their classical condensation reactions with suitable carbonyl compounds is advantageous because this method avoids hazardous metallic reagents, toxic oxidants and pre-activation/pre-functionalization step(s). In this account, the concept of direct CH functionalization of aliphatic amines based on the classical condensation-isomerization-addition (CIA) strategy followed by recent contributions from our ongoing research in the field along with relevant examples from other groups are described. Successes in stereo- and regioselective CC and CO bond formation via direct α- as well as β-C(sp(3) )-H functionalization are discussed. PMID:27185195

  3. The glucosinolate-myrosinase system in nasturtium (Tropaeolum majus L.): variability of biochemical parameters and screening for clones feasible for pharmaceutical utilization.

    PubMed

    Kleinwächter, Maik; Schnug, Ewald; Selmar, Dirk

    2008-12-10

    Leaves of Tropaeolum majus L. contain high amounts of the glucosinolate glucotropaeolin. They are used in traditional medicine to treat infections of the urinary tract. When Tropaeolum leaves are consumed, glucotropaeolin is hydrolyzed to yield mustard oils, which are absorbed in the intestine and excreted in the urine, exhibiting their antimicrobial activity. For a corresponding phytopharmacon, a sufficiently high glucotropaeolin concentration is required and any degradation of glucosinolates while drying must be minimized, i.e. the post mortal cleavage by myrosinases, which are activated by ascorbic acid. In extensive screenings, the dominant parameters determining the glucotropaeolin content in the dried leaves were quantified. It turned out that the glucotropaeolin concentration in the dried leaves represented the most suitable screening parameter. The screening of several hundred Tropaeolum plants resulted in the selection of eight high-yield varieties, from which in vitro plants had been generated and propagated as a source for large field trials. PMID:18986152

  4. Growth temperature affects sensory quality and contents of glucosinolates, vitamin C and sugars in swede roots (Brassica napus L. ssp. rapifera Metzg.).

    PubMed

    Johansen, Tor J; Hagen, Sidsel F; Bengtsson, Gunnar B; Mølmann, Jørgen A B

    2016-04-01

    Swede is a root vegetable grown under a range of growth conditions that may influence the product quality. The objective of this controlled climate study was to find the effect of growth temperature on sensory quality and the contents of glucosinolates, vitamin C and soluble sugars. High temperature (21 °C) enhanced the intensities of sensory attributes like pungent odour, bitterness, astringency and fibrousness, while low temperature (9 °C) was associated with acidic odour, sweet taste, crispiness and juiciness. Ten glucosinolates were quantified, with progoitrin as the dominant component followed by glucoberteroin, both with highest content at 21 °C. Vitamin C also had its highest content at 21 °C, while the total sugar content was lowest at this temperature. In conclusion, the study demonstrated clear effects of growth temperature on sensory quality and some chemical properties of swede and indicated a good eating quality of swedes grown at low temperatures. PMID:26593487

  5. The polymorphic hMSH5 C85T allele augments radiotherapy-induced spermatogenic impairment.

    PubMed

    Zhu, Y; Gao, G; Xia, L; Li, X; Wu, X; Her, C; Xu, K

    2016-09-01

    The hMSH5 C85T polymorphism (encoding hMSH5 P29S) is associated with male infertility and radiation-induced apoptotic response. To date, however, the potential association of hMSH5 C85T polymorphism with DNA damage accumulation in spermatozoa of cancer patients treated with radiotherapy is largely unknown. We investigated hMSH5 C85T allele and genotype frequencies, routine semen analysis and sperm DNA Fragmentation Index (DFI) in 113 testicular germ cell tumor (TGCT) patients before and after radiotherapy. The hMSH5 C85T allele is not associated with the occurrence of TGCT. However, in comparison with the CC genotype, TGCT patients with the CT + TT genotypes showed significantly altered sperm counts, sperm morphology and DFI after radiotherapy. Finally, the results of the DSB repair assay demonstrated that hMSH5 P29S could enhance radiotherapy-induced DNA damage by unleashing error-prone non-homologous end joining. Together, our studies indicate that the hMSH5 C85T variation could have an impact on the severity of radiotherapy-provoked long-term side effects through compromising the repair of radiation-induced DNA lesions. PMID:27370712

  6. Friction differences between aliphatic and aromatic structures in lubrication of titanium

    NASA Technical Reports Server (NTRS)

    Buckley, D. H.

    1975-01-01

    Sliding friction experiments were conducted with a titanium (0001) single crystal surface with various adsorbed aliphatic and aromatic compounds containing the same number of carbon atoms. An Auger emission spectroscopy analysis was used to monitor the presence of the organic lubricating compounds. Results of the investigation indicate that hexane and benzene give the same friction coefficients over a range of loads. At light loads the friction decreased with an increase in the halogen atom size where the halogens chlorine, bromine, and iodine are incorporated into the benzene molecular structure. The aliphatic compounds chlorohexane and bromohexane exhibited lower friction coefficients than the aromatic structures chlorobenzene and bromobenzene.

  7. An Iminium Salt Organocatalyst for Selective Aliphatic C-H Hydroxylation.

    PubMed

    Wang, Daoyong; Shuler, William G; Pierce, Conor J; Hilinski, Michael K

    2016-08-01

    The first examples of catalysis of aliphatic C-H hydroxylation by an iminium salt are presented. The method allows the selective organocatalytic hydroxylation of unactivated 3° C-H bonds at room temperature using hydrogen peroxide as the terminal oxidant. Hydroxylation of an unactivated 2° C-H bond is also demonstrated. Furthermore, improved functional group compatibility over other catalytic methods is reported in the form of selectivity for aliphatic C-H hydroxylation over alcohol oxidation. On the basis of initial mechanistic studies, an oxaziridinium species is proposed as the active oxidant. PMID:27391543

  8. Evaluation of biological value and appraisal of polyphenols and glucosinolates from organic baby-leaf salads as antioxidants and antimicrobials against important human pathogenic bacteria.

    PubMed

    Aires, Alfredo; Marques, Esperança; Carvalho, Rosa; Rosa, Eduardo A S; Saavedra, Maria J

    2013-01-01

    The present investigation has been carried out to investigate the biological role of four different types of baby-leaf salads and to study their potential as natural sources of antioxidants and antimicrobials against several isolates from important human pathogenic bacteria. Four single types of salads (green lettuce, red lettuce, rucola and watercress) and two mixtures [(1) red lettuce+green lettuce; (2) green lettuce + red lettuce + watercress + rucola] were assayed. The HPLC analysis revealed interesting levels of polyphenols and glucosinolates. The results showed a significant variation (p < 0.05) of polyphenols and glucosinolates with plant material. Nine different types of polyphenols grouped in three major classes were found: gallic acid, chlorogenic acid, caffeic acid and dicaffeoyltartaric acid (phenolic acids); quercitin-3-O-rutinoside, quercitin-3-O-rhamnoside, luteolin-7-O-glucoside and isorhamnetin (flavonoids); and cyanidin-3-glucoside (anthocyanins). Only three different glucosinolates were found: glucoraphanin; gluconasturtiin and 4-methoxy-glucobrassicin. A positive correlation was detected between polyphenol contents and antioxidant activity. Red lettuce and mixture 1 were the baby-leaf salads with the highest antioxidant potential. As for the antimicrobial activity, the results showed a selective effect of chemicals against Gram-positive and Gram-negative bacteria and Enterococcus faecalis and Staphylococcus aureus were the bacteria most affected by the phytochemicals. Based on the results achieved baby-leaf salads represent an important source of natural antioxidants and antimicrobial substances. PMID:23603948

  9. Profiling glucosinolates and phenolics in vegetative and reproductive tissues of the multi-purpose trees Moringa oleifera L. (horseradish tree) and Moringa stenopetala L.

    PubMed

    Bennett, Richard N; Mellon, Fred A; Foidl, Nikolaus; Pratt, John H; Dupont, M Susan; Perkins, Lionel; Kroon, Paul A

    2003-06-01

    Moringa species are important multi-purpose tropical crops, as human foods and for medicine and oil production. There has been no previous comprehensive analysis of the secondary metabolites in Moringa species. Tissues of M. oleifera from a wide variety of sources and M. stenopetala from a single source were analyzed for glucosinolates and phenolics (flavonoids, anthocyanins, proanthocyanidins, and cinnamates). M. oleifera and M. stenopetala seeds only contained 4-(alpha-l-rhamnopyranosyloxy)-benzylglucosinolate at high concentrations. Roots of M. oleifera and M. stenopetala had high concentrations of both 4-(alpha-l-rhamnopyranosyloxy)-benzylglucosinolate and benzyl glucosinolate. Leaves from both species contained 4-(alpha-l-rhamnopyranosyloxy)-benzylglucosinolate and three monoacetyl isomers of this glucosinolate. Only 4-(alpha-l-rhamnopyranosyloxy)-benzylglucosinolate was detected in M. oleifera bark tissue. M. oleifera leaves contained quercetin-3-O-glucoside and quercetin-3-O-(6' '-malonyl-glucoside), and lower amounts of kaempferol-3-O-glucoside and kaempferol-3-O-(6' '-malonyl-glucoside). M. oleifera leaves also contained 3-caffeoylquinic acid and 5-caffeoylquinic acid. Leaves of M. stenopetala contained quercetin 3-O-rhamnoglucoside (rutin) and 5-caffeoylquinic acid. Neither proanthocyanidins nor anthocyanins were detected in any of the tissues of either species. PMID:12769522

  10. Mid-infrared spectral characteristics of lipid molecular structures in Brassica carinata seeds: relationship to oil content, fatty acid and glucosinolate profiles, polyphenols, and condensed tannins.

    PubMed

    Xin, Hangshu; Khan, Nazir A; Falk, Kevin C; Yu, Peiqiang

    2014-08-13

    The objectives of this study were to quantify lipid-related inherent molecular structures using a Fourier transform infrared spectroscopy (FT-IR) technique and determine their relationship to oil content, fatty acid and glucosinolate profile, total polyphenols, and condensed tannins in seeds from newly developed yellow-seeded and brown-seeded Brassica carinata lines. Canola seeds were used as a reference. The lipid-related molecular spectral band intensities were strongly correlated to the contents of oil, fatty acids, glucosinolates, and polyphenols. The regression equations gave relatively high predictive power for the estimation of oil (R² = 0.99); all measured fatty acids (R² > 0.80), except C14:0, C20:3n-3, C22:2n-9, and C22:2n-6; 3-butenyl, 2-OH-3-butenyl, 4-OH-3-CH3-indolyl, and total glucosinolates (R² > 0.686); and total polyphenols (R² = 0.935). However, further study is required to obtain predictive equations based on large numbers of samples from diverse sources to illustrate the general applicability of these regression equations. PMID:25046077

  11. KIF5C, a novel neuronal kinesin enriched in motor neurons.

    PubMed

    Kanai, Y; Okada, Y; Tanaka, Y; Harada, A; Terada, S; Hirokawa, N

    2000-09-01

    Kinesin superfamily proteins (KIFs) are the molecular motors conveying cargos along microtubules. KIF5s, the heavy chains of conventional kinesin (KHC), are originally identified members of KIFs, and neuronal KIF5A and ubiquitous KIF5B have been identified so far. In the present work, we cloned a novel member of KIF5, KIF5C, and generated specific antibodies against three KIF5s to investigate their distribution and functions. KIF5A showed pan-neuronal distribution in the nervous system. KIF5B showed a glial cell distribution pattern in general; however, interestingly, its expression was strongly upregulated in axon-elongating neurons, such as olfactory primary neurons and mossy fibers. KIF5C was also a neuronal KIF5 like KIF5A but was highly expressed in lower motor neurons in 2-week-old or older mice, suggesting its important roles in the maintenance of motor neurons rather than in their formation, such as axonal elongation. Because a large part of KIF5s in adult motor neurons were expected to be KIF5C, we generated mice lacking the kif5C gene to investigate the functions of KIF5C in neurons in living animals. The mutant mice showed smaller brain size but were viable and did not show gross changes in the nervous system. Closer examinations revealed the relative loss of motor neurons to sensory neurons. Because three KIF5s showed high similarity in the amino acid sequence, could rescue the KIF5B mutant cells, and could form heterodimers, we think that there are functional redundancy among the three KIF5s and that KIF5A and KIF5B prevented the KIF5C null mice from the severe phenotype. PMID:10964943

  12. SELECTIVE ENUMERATION OF AROMATIC AND ALIPHATIC HYDROCARBON DEGRADING BACTERIA BY A MOST-PROBABLE-NUMBER PROCEDURE

    EPA Science Inventory

    A most-portable-number (MPN) procedure was developed to separately enumerate aliphatic and aromatic hydrocarbon degrading bacteria, because most of the currently available methods are unable to distinguish between these two groups. Separate 96-well microtiter plates are used to ...

  13. Decrease of aliphatic CHs from diatoms by in situ heating infrared microspectroscopy

    NASA Astrophysics Data System (ADS)

    Alipour, Leila; Nakashima, Satoru

    2016-04-01

    In situ heating IR microspectroscopy at 260-300°C under air and N2 conditions has been conducted on diatom frustules to examine aliphatic CH losses during heating, simulating their changes with burial-diagenesis. Assuming a reaction model made up of two first-order kinetic relations, reaction rate constants k1 and k2 and activation energies (Ea) were evaluated for aliphatic CHs. The rate constants for loss of aliphatic CHs of diatom frustules under air and N2 flow are much larger, with much smaller activation energies (57-109 kJ/mol: air; 14-44 kJ/mol: N2), than those for conventional hydrocarbon generation reactions from kerogens (170-370 kJ/mol) studied at higher temperatures (350-450°C). The CH decrease rates are somewhat different from the amide I decrease (protein degradation) rates. The obtained results suggest that organic transformation reactions including degradation of aliphatic CHs inside the diatom silica frustules might be quite different from those of kerogens separated from the biological structures.

  14. Joint Test Protocol for Validation of Alternatives to Aliphatic Isocyanate Polyurethanes

    NASA Technical Reports Server (NTRS)

    Lewis, Pattie

    2005-01-01

    The primary objective of this effort is to demonstrate and validate alternatives to aliphatic isocyanate polyurethanes. Successful completion of this project will result in one or more isocyanate-free coatings qualified for use at AFSPC and NASA installations participating in this project.

  15. PRECONCENTRATION OF ALIPHATIC AMINES FROM WATER DETERMINED BY CAPILLARY ELECTROPHORESIS WITH INDIRECT UV DETECTION

    EPA Science Inventory

    Preconcentration methodology based on adsorption chromatographies for enriching aliphatic amines (c1 to C4 substituted primary, secondary, and tertiary) and alkanolamines in water was studied by free zone capillary electrophoresis (CZE)with indirect UV detection. The solid-phase ...

  16. Modification of eucalyptus pulp fiber using silane coupling agents with aliphatic side chains of different length

    Technology Transfer Automated Retrieval System (TEKTRAN)

    The objective of this work was to evaluate the effect of three silane coupling agents with different aliphatic chain lengths on the hydrophobicity of eucalyptus pulp fiber. The three silanes coupling agents used (isobutyltrimethoxysilane, methyltrimethoxysilane, and n-octyltriethoxysilane [OTES]) we...

  17. 40 CFR 721.530 - Substituted aliphatic acid halide (generic name).

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... substance and significant new uses subject to reporting. (1) The chemical substance substituted aliphatic acid halide (PMN P-84-491) is subject to reporting under this section for the significant new uses... (CONTINUED) TOXIC SUBSTANCES CONTROL ACT SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses...

  18. 40 CFR 721.530 - Substituted aliphatic acid halide (generic name).

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... substance and significant new uses subject to reporting. (1) The chemical substance substituted aliphatic acid halide (PMN P-84-491) is subject to reporting under this section for the significant new uses... (CONTINUED) TOXIC SUBSTANCES CONTROL ACT SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses...

  19. Mass spectral analysis of C3 and C4 aliphatic amino acid derivatives.

    NASA Technical Reports Server (NTRS)

    Lawless, J. G.; Chadha, M. S.

    1971-01-01

    Diagnostic criteria are obtained for the distinction of alpha, beta, gamma, and N-methyl isomers of the C3 and C4 aliphatic amino acids, using mass spectral analysis of the derivatives of these acids. The use of deuterium labeling has helped in the understanding of certain fragmentation pathways.

  20. PATTERN RECOGNITION ANALYSIS OF A SET OF MUTAGENIC ALIPHATIC N-NITROSAMINES

    EPA Science Inventory

    A set of 21 mutagenic aliphatic N-nitrosamines were subjected to a pattern recognition analysis using ADAPT software. Four descriptors based on molecular connectivity, geometry and sigma charge on nitrogen were capable of achieving a 100% classification using the linear learning ...

  1. Spectrofluorimetric evaluation of total aliphatic and aromatic amines in well waters and wastewaters

    SciTech Connect

    Djozan, D.; Faraj-Zadeh, M.A.

    1998-09-01

    Aliphatic and aromatic amines are important metabolic intermediates in decomposition processes and are distributed in wastewaters. Monitoring of these compounds in the water samples can indicate whether the environmental waters are contaminated with wastewaters. A simple and rapid spectrofluorimetric method is described for the determination of aliphatic and aromatic amines on the basis of ammonia and aniline, respectively. Aromatic amines in samples were reacted at pH 5.5 with fluram immobilized on an Octadecylsilane Solid Phase Extraction (ODS-SPE) cartridge. The produced pyrrolinones were adsorbed on SPE and separated from the aliphatic amines. Analysis of these compounds was carried out by elution of SPE with 1 ml Tetrahydrofuran (THF) and determination of fluorescence intensity at excitation wavelength 400 nm and emission wavelength 475 nm. Aliphatic amines after passing from SPE were collected and reacted with fluram at pH 9.2, and extracted into dichloromethane at pH 3 and quantitated fluorimetrically. Linear dynamic ranges and detection limits (LOD) were 1-20, 0.43 mg l{sup {minus}1} and 1-200, 0.39 {micro}g l{sup {minus}1} for ammonia and aniline, respectively. The proposed method was successfully applied for the evaluation of these compounds in local well waters and municipality wastewaters.

  2. Copper-catalyzed aliphatic C-H amination with an amidine moiety.

    PubMed

    Chen, Hui; Sanjaya, Stephen; Wang, Yi-Feng; Chiba, Shunsuke

    2013-01-01

    A method for amination of aliphatic C-H bonds of N-alkylamidines is described that utilizes Cu(OAc)(2) as the catalyst in the presence of PhI(OAc)(2) and K(3)PO(4). The resulting products, dihydroimidazoles and tetrahydropyrimidines, could be converted into the corresponding diamines by hydride reduction. PMID:23252919

  3. Ruthenium/Imidazolylphosphine catalysis: hydrogenation of aliphatic and aromatic nitriles to form amines.

    PubMed

    Werkmeister, Svenja; Junge, Kathrin; Wendt, Bianca; Spannenberg, Anke; Jiao, Haijun; Bornschein, Christoph; Beller, Matthias

    2014-04-01

    A convenient and efficient catalyst system for the hydrogenation of aliphatic nitriles towards the corresponding primary amines in high to excellent yields is presented. In addition, aromatic nitriles are reduced smoothly, too. The use of low catalyst loadings and molecular hydrogen make this protocol an attractive methodology. PMID:24615766

  4. IN-SITU AQUIFER RESTORATION OF CHLORINATED ALIPHATICS BY METHANOTROPHIC BACTERIA

    EPA Science Inventory

    This project evaluated the potential of enhanced in-situ biotransformation of chlorinated aliphatic solvents by a bacterial community grown on methane under aerobic conditions. The target chlorinated compounds were trichloroethene (TCE), cis-and trans-1,2-dichloroethene (DCE), an...

  5. 26 CFR 5c.103-2 - Leases and industrial development bonds.

    Code of Federal Regulations, 2011 CFR

    2011-04-01

    ... 26 Internal Revenue 14 2011-04-01 2010-04-01 true Leases and industrial development bonds. 5c.103....103-2 Leases and industrial development bonds. For purposes of section 103(b)(2), the determination of whether an obligation constitutes an industrial development bond shall be made without regard to...

  6. 26 CFR 5c.103-2 - Leases and industrial development bonds.

    Code of Federal Regulations, 2010 CFR

    2010-04-01

    ... 26 Internal Revenue 14 2010-04-01 2010-04-01 false Leases and industrial development bonds. 5c.103....103-2 Leases and industrial development bonds. For purposes of section 103(b)(2), the determination of whether an obligation constitutes an industrial development bond shall be made without regard to...

  7. 26 CFR 5c.103-2 - Leases and industrial development bonds.

    Code of Federal Regulations, 2013 CFR

    2013-04-01

    ... 26 Internal Revenue 14 2013-04-01 2013-04-01 false Leases and industrial development bonds. 5c.103....103-2 Leases and industrial development bonds. For purposes of section 103(b)(2), the determination of whether an obligation constitutes an industrial development bond shall be made without regard to...

  8. 26 CFR 5c.103-2 - Leases and industrial development bonds.

    Code of Federal Regulations, 2014 CFR

    2014-04-01

    ... 26 Internal Revenue 14 2014-04-01 2013-04-01 true Leases and industrial development bonds. 5c.103....103-2 Leases and industrial development bonds. For purposes of section 103(b)(2), the determination of whether an obligation constitutes an industrial development bond shall be made without regard to...

  9. 26 CFR 5c.103-2 - Leases and industrial development bonds.

    Code of Federal Regulations, 2012 CFR

    2012-04-01

    ... 26 Internal Revenue 14 2012-04-01 2012-04-01 false Leases and industrial development bonds. 5c.103....103-2 Leases and industrial development bonds. For purposes of section 103(b)(2), the determination of whether an obligation constitutes an industrial development bond shall be made without regard to...

  10. 26 CFR 5c.168(f)(8)-1 - Special rules for leases.

    Code of Federal Regulations, 2010 CFR

    2010-04-01

    ... 26 Internal Revenue 14 2010-04-01 2010-04-01 false Special rules for leases. 5c.168(f)(8)-1....168(f)(8)-1 Special rules for leases. (a) In general. Section 168(f)(8) of the Internal Revenue Code of 1954 provides special rules for characterizing certain agreements as leases and characterizing...

  11. 26 CFR 5c.103-1 - Leases and capital expenditures.

    Code of Federal Regulations, 2010 CFR

    2010-04-01

    ... 26 Internal Revenue 14 2010-04-01 2010-04-01 false Leases and capital expenditures. 5c.103-1...-1 Leases and capital expenditures. For purposes of section 103(b)(6)(D) and § 1.103-10(b)(2)(iv)(b... subject to a lease shall be made without regard to the characterization of the transaction as a...

  12. 9 CFR 381.221 - Designation of States under paragraph 5(c) of the Act.

    Code of Federal Regulations, 2010 CFR

    2010-01-01

    ... CFR Sections Affected, which appears in the Finding Aids section of the printed volume and on GPO... 9 Animals and Animal Products 2 2010-01-01 2010-01-01 false Designation of States under paragraph 5(c) of the Act. 381.221 Section 381.221 Animals and Animal Products FOOD SAFETY AND...

  13. 26 CFR 5c.168(f)(8)-4 - Minimum investment of lessor.

    Code of Federal Regulations, 2014 CFR

    2014-04-01

    ... 26 Internal Revenue 14 2014-04-01 2013-04-01 true Minimum investment of lessor. 5c.168(f)(8)-4....168(f)(8)-4 Minimum investment of lessor. (a) Minimum investment. Under section 168(f)(8)(B)(ii), an... has a minimum at risk investment which, at the time the property is placed in service under the...

  14. 26 CFR 5c.168(f)(8)-4 - Minimum investment of lessor.

    Code of Federal Regulations, 2011 CFR

    2011-04-01

    ... 26 Internal Revenue 14 2011-04-01 2010-04-01 true Minimum investment of lessor. 5c.168(f)(8)-4....168(f)(8)-4 Minimum investment of lessor. (a) Minimum investment. Under section 168(f)(8)(B)(ii), an... has a minimum at risk investment which, at the time the property is placed in service under the...

  15. 26 CFR 5c.168(f)(8)-4 - Minimum investment of lessor.

    Code of Federal Regulations, 2012 CFR

    2012-04-01

    ... 26 Internal Revenue 14 2012-04-01 2012-04-01 false Minimum investment of lessor. 5c.168(f)(8)-4....168(f)(8)-4 Minimum investment of lessor. (a) Minimum investment. Under section 168(f)(8)(B)(ii), an... has a minimum at risk investment which, at the time the property is placed in service under the...

  16. 26 CFR 5c.168(f)(8)-4 - Minimum investment of lessor.

    Code of Federal Regulations, 2013 CFR

    2013-04-01

    ... 26 Internal Revenue 14 2013-04-01 2013-04-01 false Minimum investment of lessor. 5c.168(f)(8)-4....168(f)(8)-4 Minimum investment of lessor. (a) Minimum investment. Under section 168(f)(8)(B)(ii), an... has a minimum at risk investment which, at the time the property is placed in service under the...

  17. 26 CFR 5c.168(f)(8)-4 - Minimum investment of lessor.

    Code of Federal Regulations, 2010 CFR

    2010-04-01

    ... 26 Internal Revenue 14 2010-04-01 2010-04-01 false Minimum investment of lessor. 5c.168(f)(8)-4....168(f)(8)-4 Minimum investment of lessor. (a) Minimum investment. Under section 168(f)(8)(B)(ii), an... has a minimum at risk investment which, at the time the property is placed in service under the...

  18. Channel Catfish, Ictalurus punctatus, ubiquitin carboxy-terminal hydrolase L5 cDNA

    Technology Transfer Automated Retrieval System (TEKTRAN)

    The ubiquitin-proteasome cycle is a complex, non-lysosomal biochemical process for intracellular protein degradation. This process involves many enzymes. One of them is ubiquitin carboxy-terminal hydrolase (UCT). In this report, we cloned, sequenced and characterized the channel catfish UCT L5 cDNA....

  19. Evaluation of the colorectal cancer risk conferred by rare UNC5C alleles

    PubMed Central

    Küry, Sébastien; Garrec, Céline; Airaud, Fabrice; Breheret, Flora; Guibert, Virginie; Frenard, Cécile; Jiao, Shuo; Bonneau, Dominique; Berthet, Pascaline; Bossard, Céline; Ingster, Olivier; Cauchin, Estelle; Bezieau, Stéphane

    2014-01-01

    AIM: To evaluate the risk associated with variants of the UNC5C gene recently suspected to predispose to familial colorectal cancer (CRC). METHODS: We screened patients with familial CRC forms as well as patients with sporadic CRCs. In a first time, we analyzed exon 11 of the UNC5C gene in 120 unrelated patients with suspected hereditary CRC, 58 patients with suspected Lynch-associated cancer or polyposis, and 132 index cases of Lynch syndrome families with a characterized mutation in a DNA mismatch repair (MMR). Next, 1023 patients with sporadic CRC and 1121 healthy individuals were screened for the variants identified in patients with familial cancer. RESULTS: Of 120 patients with familial CRC of unknown etiology, one carried the previously reported mis-sense mutation p.Arg603Cys (R603C) and another exhibited the unreported variant of unknown significance p.Thr617Ile (T617I). The p.Ala628Lys (A628K) mutation previously described as the main UNC5C risk variant for familial CRC was not detected in any cases of familial CRC of unknown etiology, but was present in a patient with familial gastric cancer and in two Lynch syndrome patients in co-occurrence with MMR mutations. A statistically non-significant increase in cancer risk was identified in familial CRC and/or other Lynch-associated cancers (1/178 patients vs 2/1121 healthy controls, OR = 3.2, 95%CI: 0.29-35.05, P = 0.348) and in sporadic CRCs (4/1023 patients vs 2/1121 healthy controls, OR = 2.2, 95%CI: 0.40-12.02, P = 0.364). CONCLUSION: We confirm that UNC5C mutations are very rare in familial and sporadic CRCs, but further investigations are needed to justify routine UNC5C testing for diagnostic purposes. PMID:24415873

  20. Biodegradation of individual and multiple chlorinated aliphatic hydrocarbons by methane-oxidizing cultures.

    PubMed Central

    Chang, H L; Alvarez-Cohen, L

    1996-01-01

    The microbial degradation of chlorinated and nonchlorinated methanes, ethanes, and ethanes by a mixed methane-oxidizing culture grown under chemostat and batch conditions is evaluated and compared with that by two pure methanotrophic strains: CAC1 (isolated from the mixed culture) and Methylosinus trichosporium OB3b. With the exception of 1,1-dichloroethylene, the transformation capacity (Tc) for each chlorinated aliphatic hydrocarbon was generally found to be in inverse proportion to its chlorine content within each aliphatic group (i.e., methanes, ethanes, and ethenes), whereas similar trends were not observed for degradation rate constants. Tc trends were similar for all methane-oxidizing cultures tested. None of the cultures were able to degrade the fully chlorinated aliphatics such as perchloroethylene and carbon tetrachloride. Of the four cultures tested, the chemostat-grown mixed culture exhibited the highest Tc for trichloroethylene, cis-1,2-dichloroethylene, tetrachloroethane, 1,1,1-trichloroethane, and 1,2-dichloroethane, whereas the pure batch-grown OB3b culture exhibited the highest Tc for all other compounds tested. The product toxicity of chlorinated aliphatic hydrocarbons in a mixture containing multiple compounds was cumulative and predictable when using parameters measured from the degradation of individual compounds. The Tc for each chlorinated aliphatic hydrocarbon in a mixture (Tcmix) and the total Tc for the mixture (sigma Tcmix) are functions of the individual Tc, the initial substrate concentration (S0), and the first-order rate constant (k/Ks) of each compound in the mixture, indicating the importance of identifying the properties and compositions of all potentially degradable compounds in a contaminant mixture. PMID:8795228

  1. Modification of oil and glucosinolate content in canola seeds with altered expression of Brassica napus LEAFY COTYLEDON1.

    PubMed

    Elahi, Nosheen; Duncan, Robert W; Stasolla, Claudio

    2016-03-01

    Over the last few decades, research focusing on canola (Brassica napus L.) seed oil content and composition has expanded. Oil production and accumulation are influenced by genes participating in embryo and seed development. The Arabidopsis LEAFY COTYLEDON1 (LEC1) is a well characterized regulator of embryo development that also enhances the expression of genes involved in fatty acid (FA) synthesis. B. napus lines over-expressing or down-regulating BnLEC1 were successfully generated by Agrobacterium-mediated transformation. The constitutive expression of BnLEC1 in B. napus var. Polo, increased seed oil content by 7-16%, while the down-regulation of BnLEC1 in B. napus var. Topas reduced oil content by 9-12%. Experimental manipulation of BnLEC1 caused transcriptional changes in enzymes participating in sucrose metabolism, glycolysis, and FA biosynthesis, suggesting an enhanced carbon flux towards FA biosynthesis in tissues over-expressing BnLEC1. The increase in oil content induced by BnLEC1 was not accompanied by alterations in FA composition, oil nutritional value or glucosinolate (GLS) levels. Suppression of BnLEC1 reduced seed oil accumulation and elevated the level of GLS possibly through the transcriptional regulation of BnST5a (Sulphotransferase5a), the last GLS biosynthetic enzyme. Collectively, these findings demonstrate that experimental alterations of BnLEC1 expression can be used to influence oil production and quality in B. napus. PMID:26773545

  2. Glucosinolates in Brassica vegetables: the influence of the food supply chain on intake, bioavailability and human health.

    PubMed

    Verkerk, Ruud; Schreiner, Monika; Krumbein, Angelika; Ciska, Ewa; Holst, Birgit; Rowland, Ian; De Schrijver, Remi; Hansen, Magnor; Gerhäuser, Clarissa; Mithen, Richard; Dekker, Matthijs

    2009-09-01

    Glucosinolates (GLSs) are found in Brassica vegetables. Examples of these sources include cabbage, Brussels sprouts, broccoli, cauliflower and various root vegetables (e.g. radish and turnip). A number of epidemiological studies have identified an inverse association between consumption of these vegetables and the risk of colon and rectal cancer. Animal studies have shown changes in enzyme activities and DNA damage resulting from consumption of Brassica vegetables or isothiocyanates, the breakdown products (BDP) of GLSs in the body. Mechanistic studies have begun to identify the ways in which the compounds may exert their protective action but the relevance of these studies to protective effects in the human alimentary tract is as yet unproven. In vitro studies with a number of specific isothiocyanates have suggested mechanisms that might be the basis of their chemoprotective effects. The concentration and composition of the GLSs in different plants, but also within a plant (e.g. in the seeds, roots or leaves), can vary greatly and also changes during plant development. Furthermore, the effects of various factors in the supply chain of Brassica vegetables including breeding, cultivation, storage and processing on intake and bioavailability of GLSs are extensively discussed in this paper. PMID:19035553

  3. Genome Wide Association Mapping in Arabidopsis thaliana Identifies Novel Genes Involved in Linking Allyl Glucosinolate to Altered Biomass and Defense

    PubMed Central

    Francisco, Marta; Joseph, Bindu; Caligagan, Hart; Li, Baohua; Corwin, Jason A.; Lin, Catherine; Kerwin, Rachel E.; Burow, Meike; Kliebenstein, Daniel J.

    2016-01-01

    A key limitation in modern biology is the ability to rapidly identify genes underlying newly identified complex phenotypes. Genome wide association studies (GWAS) have become an increasingly important approach for dissecting natural variation by associating phenotypes with genotypes at a genome wide level. Recent work is showing that the Arabidopsis thaliana defense metabolite, allyl glucosinolate (GSL), may provide direct feedback regulation, linking defense metabolism outputs to the growth, and defense responses of the plant. However, there is still a need to identify genes that underlie this process. To start developing a deeper understanding of the mechanism(s) that modulate the ability of exogenous allyl GSL to alter growth and defense, we measured changes in plant biomass and defense metabolites in a collection of natural 96 A. thaliana accessions fed with 50 μM of allyl GSL. Exogenous allyl GSL was introduced exclusively to the roots and the compound transported to the leaf leading to a wide range of heritable effects upon plant biomass and endogenous GSL accumulation. Using natural variation we conducted GWAS to identify a number of new genes which potentially control allyl responses in various plant processes. This is one of the first instances in which this approach has been successfully utilized to begin dissecting a novel phenotype to the underlying molecular/polygenic basis. PMID:27462337

  4. Influence of seasonal variation and methyl jasmonate mediated induction of glucosinolate biosynthesis on quinone reductase activity in broccoli florets.

    PubMed

    Ku, Kang Mo; Jeffery, Elizabeth H; Juvik, John A

    2013-10-01

    Methyl jasmonate spray treatments (250 μM) were utilized to alter glucosinolate composition in the florets of the commercial broccoli F1 hybrids 'Pirate', 'Expo', 'Green Magic', 'Imperial', and 'Gypsy' grown in replicated field plantings in 2009 and 2010. MeJA treatment significantly increased glucoraphanin (11%), gluconasturtiin (59%), and neoglucobrassicin (248%) concentrations and their hydrolysis products including sulforaphane (152%), phenethyl isothiocyanate (318%), N-methoxyindole-3-carbinol (313%), and neoascorbigen (232%) extracted from florets of these genotypes over two seasons. Increased quinone reductase (QR) activity was significantly correlated with increased levels of sulforaphane, N-methoxyindole-3-carbinol, and neoascorbigen. Partitioning experiment-wide trait variances indicated that the variability in concentrations of sulforaphane (29%), neoascorbigen (48%), and QR activity (72%) was influenced by year-associated weather variables, whereas variation in neoglucobrassicin (63%) and N-methoxyindole-3-carbinol (46%) concentrations was primarily attributed to methyl jasmonate treatment. These results suggest that methyl jasmonate treatment can enhance QR inducing activity by increased hydrolysis of glucoraphanin into sulforaphane and the hydrolysis products of neoglucobrassicin. PMID:24032372

  5. Synthesis of oxazolo[4,5-c]quinoline TRPV1 antagonists.

    PubMed

    Voight, Eric A; Daanen, Jerome F; Kort, Michael E

    2010-12-17

    An efficient synthesis of 2-amino-oxazolo[4,5-c]quinoline TRPV1 antagonists is described via a thiourea formation/carbodiimide cyclization sequence. Synthetic route optimization eliminates intermediate isolations and facilitates the rapid preparation of a series of novel pentacyclic TRPV1 antagonists. From this series, compound (S)-4 was identified as a potent and selective ligand for the TRPV1 ion channel. PMID:21090730

  6. 28. Details for reinforcing L5 C56 span 6. Photographic ...

    Library of Congress Historic Buildings Survey, Historic Engineering Record, Historic Landscapes Survey

    28. Details for reinforcing L5 - C5-6 span 6. Photographic copy of drawing no. B-2-645-2, C.P.R. Algoma District-Thessalon Subdivision, Bridge no. 134.06-International Bridge at Sault Ste. Marie Bridge (from Canadian National Railroad, Sault Ste. Marie, Michigan). Delineator unknown, January 9, 1933. - Sault Ste. Marie International Railroad Bridge, Spanning Soo Locks at St. Marys Falls Canal, Sault Ste. Marie, Chippewa County, MI

  7. Activating mutations in the NT5C2 nucleotidase gene drive chemotherapy resistance in relapsed ALL

    PubMed Central

    Tzoneva, Gannie; Garcia, Arianne Perez; Carpenter, Zachary; Khiabanian, Hossein; Tosello, Valeria; Allegretta, Maddalena; Paietta, Elisabeth; Racevskis, Janis; Rowe, Jacob M.; Tallman, Martin S.; Paganin, Maddalena; Basso, Giuseppe; Hof, Jana; Kirschner-Schwabe, Renate; Palomero, Teresa; Rabadan, Raul; Ferrando, Adolfo

    2013-01-01

    Acute lymphoblastic leukemia (ALL) is an aggressive hematological tumor resulting from the malignant transformation of lymphoid progenitors. Despite intensive chemotherapy, 20% of pediatric and over 50% of adult ALL patients fail to achieve a complete remission or relapse after intensified chemotherapy, making disease relapse and resistance to therapy the most significant challenge in the treatment of this disease1,2. Using whole exome sequencing, here we identify mutations in the cytosolic 5'-nucleotidase II gene (NT5C2), which encodes a 5'-nucleotidase enzyme responsible for inactivation of nucleoside analog chemotherapy drugs, in 20/103 (19%) relapse T-ALLs and in 1/35 (3%) relapse B-precursor ALLs analyzed. NT5C2 mutant proteins show increased nucleotidase activity in vitro and conferred resistance to chemotherapy with 6-mercaptopurine and 6-thioguanine when expressed in ALL lymphoblasts. These results support a prominent role for activating mutations in NT5C2 and increased nucleoside analog metabolism in disease progression and chemotherapy resistance in ALL. PMID:23377281

  8. Effect of Cr on electronic and magnetic properties of χ-carbide (Fe,Cr)5C2

    NASA Astrophysics Data System (ADS)

    Wang, B.; Zhang, Q.; Zhang, Z. F.; Lv, Z. Q.; Fu, W. T.

    2015-10-01

    From density-function theory calculation, the structural, electronic and magnetic properties of χ-carbides (Fe,Cr)5C2 are investigated. With the increase of Cr content in χ-carbides (Fe,Cr)5C2, the formation energy of χ carbide gradually decrease and energy stability of them increase. The formation energy of Cr5C2 is -0.354 eV/f.u, and the stability of Cr5C2 is higher than other χ carbides (Fe,Cr)5C2, Mn5C2 and Fe5C2. There exists charges transfer from metal cation (Fe/Cr) to C atoms in χ-carbides, and this reveals an ionic contribution to the bonds. The addition of Cr decreases the magnetic moments of χ carbide, and the magnetic moments (Ms) of Cr2Cr2FeC2 and Cr5C2 are 0 μB/f.u., while it expresses opposite magnetic characters of the same atom at different sites in the other χ type (Fe,Cr)5C2 carbides. The 3d states of metal atoms in the majority states (up) move to above the Femi level and some metal atoms (Fe/Cr) in χ type (Fe,Cr)5C2 are undergone the anti-ferromagnetic transformation.

  9. Self-assembly of short peptides composed of only aliphatic amino acids and a combination of aromatic and aliphatic amino acids.

    PubMed

    Subbalakshmi, Chilukuri; Manorama, Sunkara V; Nagaraj, Ramakrishnan

    2012-05-01

    The morphology of structures formed by the self-assembly of short N-terminal t-butyloxycarbonyl (Boc) and C-terminal methyl ester (OMe) protected and Boc-deprotected hydrophobic peptide esters was investigated. We have observed that Boc-protected peptide esters composed of either only aliphatic hydrophobic amino acids or aliphatic hydrophobic amino acids in combination with aromatic amino acids, formed highly organized structures, when dried from methanol solutions. Transmission and scanning electron microscopic images of the peptides Boc-Ile-Ile-OMe, Boc-Phe-Phe-Phe-Ile-Ile-OMe and Boc-Trp-Ile-Ile-OMe showed nanotubular structures. Removal of the Boc group resulted in disruption of the ability to form tubular structures though spherical aggregates were formed. Both Boc-Leu-Ile-Ile-OMe and H-Leu-Ile-Ile-OMe formed only spherical nanostructures. Dynamic light scattering studies showed that aggregates of varying dimensions were present in solution suggesting that self-assembly into ordered structures is facilitated by aggregation in solution. Fourier transform infrared spectroscopy and circular dichroism spectroscopy data show that although all four of the protected peptides adopt well-defined tertiary structures, upon removal of the Boc group, only H-Phe-Phe-Phe-Ile-Ile-OMe had the ability to adopt β-structure. Our results indicate that hydrophobic interaction is a very important determinant for self-assembly and presence of charged and aromatic amino acids in a peptide is not necessary for self-assembly. PMID:22431418

  10. Plants as Biofactories: Postharvest Stress-Induced Accumulation of Phenolic Compounds and Glucosinolates in Broccoli Subjected to Wounding Stress and Exogenous Phytohormones

    PubMed Central

    Villarreal-García, Daniel; Nair, Vimal; Cisneros-Zevallos, Luis; Jacobo-Velázquez, Daniel A.

    2016-01-01

    Broccoli contains high levels of bioactive molecules and is considered a functional food. In this study, postharvest treatments to enhance the concentration of glucosinolates and phenolic compounds were evaluated. Broccoli whole heads were wounded to obtain florets and wounded florets (florets cut into four even pieces) and stored for 24 h at 20 °C with or without exogenous ethylene (ET, 1000 ppm) or methyl jasmonate (MeJA, 250 ppm). Whole heads were used as a control for wounding treatments. Regarding glucosinolate accumulation, ET selectively induced the 4-hydroxylation of glucobrassicin in whole heads, resulting in ∼223% higher 4-hydroxyglucobrassicin than time 0 h samples. Additionally, glucoraphanin was increased by ∼53% in whole heads treated with ET, while neoglucobrassicin was greatly accumulated in wounded florets treated with ET or MeJA, showing increases of ∼193 and ∼286%, respectively. On the other hand, although only whole heads stored without phytohormones showed higher concentrations of phenolic compounds, which was reflected in ∼33, ∼30, and ∼46% higher levels of 1,2,2-trisinapoylgentiobose, 1,2-diferulolylgentiobiose, and 1,2-disinapoyl-2-ferulolylgentiobiose, respectively; broccoli florets stored under air control conditions showed enhanced concentrations of 3-O-caffeoylquinic acid, 1,2-disinapoylgentiobiose, and 1,2-disinapoyl-2-ferulolylgentiobiose (∼22, ∼185, and ∼65% more, respectively). Furthermore, exogenous ET and MeJA impeded individual phenolics accumulation. Results allowed the elucidation of simple and effective postharvest treatment to enhance the content of individual glucosinolates and phenolic compounds in broccoli. The stressed-broccoli tissue could be subjected to downstream processing in order to extract and purify bioactive molecules with applications in the dietary supplements, agrochemical and cosmetics markets. PMID:26904036

  11. Colorless triphenylamine-based aliphatic thermoset epoxy for multicolored and near-infrared electrochromic applications.

    PubMed

    Chuang, Ya-Wen; Yen, Hung-Ju; Wu, Jia-Hao; Liou, Guey-Sheng

    2014-03-12

    In this study, two novel colorless thermoset epoxy resins with anodically electrochromism were prepared from the thermal curing of two triphenylamine-based diamine monomers, 4,4'-diamino-4″-methoxytriphenylamine (1) and N,N'-bis(4-aminophenyl)-N,N'-di(4-methoxylphenyl)-1,4-phenylenediamine (2) with aliphatic epoxy triglycidyl isocyanurate, respectively. The resulting thermoset epoxy resins showed excellent softening temperature (Ts, 270 and 280 °C) due to the rigid structure and highly crosslinking density. In addition, novel colorless epoxy resin films revealed good reversible electrochemical oxidation and interesting multi-electrochromic behavior with high contrast ratio both in visible and near-infrared regions. The aliphatic thermoset epoxy resins also exhibited high transparency in visible region as colorless and great potential for practical electrochromic applications. PMID:24456516

  12. Synthesis and Bioactivity of 5-Substituted-2-furoyl Diacylhydazide Derivatives with Aliphatic Chain

    PubMed Central

    Cui, Zining; Li, Xinghai; Tian, Fang; Yan, Xiaojing

    2014-01-01

    A series of 5-substituted-2-furoyl diacylhydazide derivatives with aliphatic chain were designed and synthesized. Their structures were characterized by IR, 1H NMR, elemental analysis, and X-ray single crystal diffraction. The anti-tumor bioassay revealed that some title compounds exhibited promising activity against the selected cancer cell lines, especially against the human promyelocytic leukemic cells (HL-60). Their fungicidal tests indicated that most of the title compounds showed significant anti-fungal activity. The preliminary structure-activity relationship showed that the aliphatic chain length and differences in the R2 group had obvious effects on the anti-tumor and anti-fungal activities. The bioassay results demonstrated that the title compounds hold great promise as novel lead compounds for further drug discovery. PMID:24853128

  13. Determination of aliphatic organic acids by high-performance liquid chromatography with pulsed electrochemical detection.

    PubMed

    Casella, Innocenzo G; Gatta, Maria

    2002-01-01

    A new ion exclusion HPLC procedure accomplished with a pulsed electrochemical detection for the determination of several common aliphatic acids is described. A triple-step waveform of the applied potentials, based on the formation/inhibition of PtOH species on the electrode surface, is successfully used for sensitive detection of several aliphatic acids in flowing systems avoiding pre- or postcolumn derivatization and/or cleanup procedures. Under optimal chromatographic conditions (i.e., 50 mM HClO(4)) the proposed method allowed detection limits between 0.5 and 7 microM for all investigated acids, and the dynamic linear range spanned generally over 1 or 2 orders of magnitude. Determination of citric, malic, tartaric, lactic, formic, and acetic acids in several foods and beverages was performed, in approximately 15 min, without the necessity of any sample pretreatment. PMID:11754537

  14. Spacecraft Maximum Allowable Concentrations (SMACs) for C3 to C8 Aliphatic Saturated Aldehydes

    NASA Technical Reports Server (NTRS)

    Langford, Shannon D.

    2007-01-01

    Spacecraft maximum allowable concentrations (SMACs) for C3 to C8, straight-chain, aliphatic aldehydes have been previously assessed and have been documented in volume 4 of Spacecraft Maximum Allowable Concentrations for Selected Airborne Contaminants (James, 2000). These aldehydes as well as associated physical properties are shown in Table 1. The C3 to C8 aliphatic aldehydes can enter the habitable compartments and contaminate breathing air of spacecraft by several routes including incomplete oxidation of alcohols in the Environmental Control and Life Support System (ECLSS) air revitalization subsystem, as a byproduct of human metabolism, through materials off-gassing, or during food preparation. These aldehydes have been detected in the atmosphere of manned space vehicles in the past. Analysis performed by NASA of crew cabin air samples from the Russian Mir Space Station revealed the presence of C3 to C8 aldehydes at concentrations peaking at approximately 0.1 mg/cu m.

  15. Friction of iron lubricated with aliphatic and aromatic hydrocarbons and halogenated analogs

    NASA Technical Reports Server (NTRS)

    Buckley, D. H.

    1976-01-01

    The influence of oxygen and various organic molecules on the reduction of the friction of an iron (011) single crystal surface was investigated. A comparison was made between aliphatic and aromatic structures, all of which contained six carbon atoms, and among various halogen atoms. Results of the investigation indicate that hexane and benzene give similar friction coefficients over a range of loads except at very light loads. At light loads, the friction decreased with an increase in the load where the halogens fluorine and chlorine are incorporated into the benzene molecular structure; however, over the same load range when bromine and iodine were present, the friction was relatively unchanged. The aliphatic compound chlorohexane exhibited lower friction coefficients than the aromatic structure chlorobenzene at very light loads. With the brominated benzene structures, however, friction was essentially the same. Oxygen was more effective in reducing friction than were the simple hydrocarbons.

  16. Source apportionment of urban particulate aliphatic and polynuclear aromatic hydrocarbons (PAHs) using multivariate methods.

    PubMed

    Kavouras, I G; Koutrakis, P; Tsapakis, M; Lagoudaki, E; Stephanou, E G; Von Baer, D; Oyola, P

    2001-06-01

    Samples of organic aerosol were collected in Santiago de Chile. An activated-charcoal diffusion denuder was used to strip out organic vapors prior to particle collection. Both polynuclear aromatic hydrocarbons (PAHs) and aliphatic hydrocarbons were determined using gas chromatography/mass spectrometry (GC/MS). Organic particle sources were resolved using both concentration diagnostic ratios and multivariate methods such as hierarchical cluster analysis (HCA) and factor analysis (FA). Four factors were identified based on the loadings of PAHs and n-alkanes and were attributed to the following sources: (1) high-temperature combustion of fuels; (2) fugitive emissions from oil residues; (3) biogenic sources; and (4) unburned fuels. Multilinear regression (MLR) analysis was used to determine emission profiles and contributions of the sources. The reconstructed concentrations of particle phase aliphatic and polynuclear aromatic hydrocarbons were in good agreement (R2 > 0.70) with those measured in Santiago de Chile. PMID:11414034

  17. Semi-metallic Be5C2 monolayer global minimum with quasi-planar pentacoordinate carbons and negative Poisson's ratio.

    PubMed

    Wang, Yu; Li, Feng; Li, Yafei; Chen, Zhongfang

    2016-01-01

    Designing new materials with novel topological properties and reduced dimensionality is always desirable for material innovation. Here we report the design of a two-dimensional material, namely Be5C2 monolayer on the basis of density functional theory computations. In Be5C2 monolayer, each carbon atom binds with five beryllium atoms in almost the same plane, forming a quasi-planar pentacoordinate carbon moiety. Be5C2 monolayer appears to have good stability as revealed by its moderate cohesive energy, positive phonon modes and high melting point. It is the lowest-energy structure with the Be5C2 stoichiometry in two-dimensional space and therefore holds some promise to be realized experimentally. Be5C2 monolayer is a gapless semiconductor with a Dirac-like point in the band structure and also has an unusual negative Poisson's ratio. If synthesized, Be5C2 monolayer may find applications in electronics and mechanics. PMID:27139572

  18. Semi-metallic Be5C2 monolayer global minimum with quasi-planar pentacoordinate carbons and negative Poisson's ratio

    NASA Astrophysics Data System (ADS)

    Wang, Yu; Li, Feng; Li, Yafei; Chen, Zhongfang

    2016-05-01

    Designing new materials with novel topological properties and reduced dimensionality is always desirable for material innovation. Here we report the design of a two-dimensional material, namely Be5C2 monolayer on the basis of density functional theory computations. In Be5C2 monolayer, each carbon atom binds with five beryllium atoms in almost the same plane, forming a quasi-planar pentacoordinate carbon moiety. Be5C2 monolayer appears to have good stability as revealed by its moderate cohesive energy, positive phonon modes and high melting point. It is the lowest-energy structure with the Be5C2 stoichiometry in two-dimensional space and therefore holds some promise to be realized experimentally. Be5C2 monolayer is a gapless semiconductor with a Dirac-like point in the band structure and also has an unusual negative Poisson's ratio. If synthesized, Be5C2 monolayer may find applications in electronics and mechanics.

  19. Semi-metallic Be5C2 monolayer global minimum with quasi-planar pentacoordinate carbons and negative Poisson's ratio

    PubMed Central

    Wang, Yu; Li, Feng; Li, Yafei; Chen, Zhongfang

    2016-01-01

    Designing new materials with novel topological properties and reduced dimensionality is always desirable for material innovation. Here we report the design of a two-dimensional material, namely Be5C2 monolayer on the basis of density functional theory computations. In Be5C2 monolayer, each carbon atom binds with five beryllium atoms in almost the same plane, forming a quasi-planar pentacoordinate carbon moiety. Be5C2 monolayer appears to have good stability as revealed by its moderate cohesive energy, positive phonon modes and high melting point. It is the lowest-energy structure with the Be5C2 stoichiometry in two-dimensional space and therefore holds some promise to be realized experimentally. Be5C2 monolayer is a gapless semiconductor with a Dirac-like point in the band structure and also has an unusual negative Poisson's ratio. If synthesized, Be5C2 monolayer may find applications in electronics and mechanics. PMID:27139572

  20. TRANSFORMATIONS OF HALOGENATED ALIPHATIC COMPOUNDS: OXIDATION, REDUCTION, SUBSTITUTION, AND DEHYDROHALOGENATION REACTIONS OCCUR ABIOTICALLY OR IN MICROBIAL AND MAMMALIAN SYSTEMS

    EPA Science Inventory

    The current understanding of abiotic and biotic chemistry of halogenated aliphatic compounds is systematized and summarized. Knowledge of abiotic transformations can provide a conceptual framework for understanding biologically mediated transformations. Most abiotic transformatio...

  1. Unique gas and hydrocarbon adsorption in a highly porous metal-organic framework made of extended aliphatic ligands.

    PubMed

    Li, Kunhao; Lee, Jeongyong; Olson, David H; Emge, Thomas J; Bi, Wenhua; Eibling, Matthew J; Li, Jing

    2008-12-14

    High and unique gas and hydrocarbon adsorption in a highly stable guest-free microporous metal-organic framework constructed on rigid aliphatic ligands, H(2)bodc and ted, is reported in this work. PMID:19082093

  2. BIOTRANSFORMATION OF MIXTURES OF CHLORINATED ALIPHATIC HYDROCARBONS BY AN ACETATE-GROWN METHANOGENIC ENRICHMENT CULTURE. (R825549C053)

    EPA Science Inventory

    Biotransformation of chlorinated aliphatic hydrocarbons under anaerobic conditions has received considerable attention due to the prevalence of these compounds as groundwater contaminants. However, information concerning the impact of mixtures of chlorinated compounds on their...

  3. DETERMINATION OF ALIPHATIC AMINES IN WATER USING DERIVATIZATION WITH FLUORESCEIN ISOTHIOCYANATE AND CAPILLARY ELECTROPHORESIS/LASER-INDUCED FLUORESCENCE DETECTION.

    EPA Science Inventory

    Detection-oriented derivatization of aliphatic amines and amine functional groups in coumpounds of environmental interest was studied using fluorescein isothiocyanate (FITC) with separation/determination by capillary electrophoresis/laser-induced fluorescence. Determinative level...

  4. SPITZER'S VIEW ON AROMATIC AND ALIPHATIC HYDROCARBON EMISSION IN HERBIG Ae STARS

    SciTech Connect

    Acke, B.; Waters, L. B. F. M.; Bouwman, J.; Juhasz, A.; Henning, Th.; Van den Ancker, M. E.; Meeus, G.; Tielens, A. G. G. M.

    2010-07-20

    The chemistry of astronomical hydrocarbons, responsible for the well-known infrared emission features detected in a wide variety of targets, remains enigmatic. Here we focus on the group of young intermediate-mass Herbig Ae stars. We have analyzed the aliphatic and polycyclic aromatic hydrocarbon (PAH) emission features in the infrared spectra of a sample of 53 Herbig Ae stars, obtained with the Infrared Spectrograph aboard the Spitzer Space Telescope. We confirm that the PAH-to-stellar luminosity ratio is higher in targets with a flared dust disk. However, a few sources with a flattened dust disk still show relatively strong PAH emission. Since PAH molecules trace the gas disk, this indicates that gas disks may still be flared, while the dust disk has settled due to grain growth. There are indications that the strength of the 11.3 {mu}m feature also depends on dust disk structure, with flattened disks being less bright in this feature. We confirm that the CC bond features at 6.2 and 7.8 {mu}m shift to redder wavelengths with decreasing stellar effective temperature. Moreover, we show that this redshift is accompanied by a relative increase of aliphatic CH emission and a decrease of the aromatic 8.6 {mu}m CH feature strength. Cool stars in our sample are surrounded by hydrocarbons with a high aliphatic/aromatic CH ratio and a low aromatic CH/CC ratio, and vice versa for the hot stars. We conclude that, while the overall hydrocarbon emission strength depends on the dust disk's geometry, the relative differences seen in the IR emission features in disks around Herbig Ae stars are mainly due to chemical differences of the hydrocarbon molecules induced by the stellar UV field. Strong UV flux reduces the aliphatic component and emphasizes the spectral signature of the aromatic molecules in the IR spectra.

  5. Gas phase heterogeneous catalytic oxidation of alkanes to aliphatic ketones and/or other oxygenates

    SciTech Connect

    Lin, Manhua; Wang, Xiang; Yeom, Younghoon

    2015-03-17

    A catalyst, its method of preparation and its use for producing aliphatic ketones by subjecting alkanes C.sub.3 to C.sub.9 to a gas phase catalytic oxidation in the presence of air or oxygen, and, optionally, steam and/or one or more diluting gases. The catalyst comprises a catalytically active mixed metal oxide phase and a suitable support material onto and/or into which the active catalytic phase id dispersed.

  6. Gas phase heterogeneous catalytic oxidation of alkanes to aliphatic ketones and/or other oxygenates

    SciTech Connect

    Lin, Manhua; Wang, Xiang; Yeom, Younghoon

    2015-09-29

    A catalyst, its method of preparation and its use for producing aliphatic ketones by subjecting alkanes C.sub.3 to C.sub.9 to a gas phase catalytic oxidation in the presence of air or oxygen, and, optionally, steam and/or one or more diluting gases. The catalyst comprises a catalytically active mixed metal oxide phase and a suitable support material onto and/or into which the active catalytic phase is dispersed.

  7. Diverse Asymmetric Hydrofunctionalization of Aliphatic Internal Alkenes through Catalytic Regioselective Hydroboration.

    PubMed

    Xi, Yumeng; Hartwig, John F

    2016-06-01

    We report a two-step strategy for diverse hydrofunctionalizations of aliphatic internal alkenes with high regioselectivity and enantioselectivity. This process comprises a copper-catalyzed asymmetric hydroboration and subsequent stereospecific derivatizations of the secondary boronates. By this strategy, a range of compounds, such as amides, alkyl fluorides and bromides, alcohols, aldehydes, arenes, and heteroarenes, were synthesized from an internal alkene with high regioselectivity and enantioselectivity. Computational studies provide insight into the origins of these selectivities. PMID:27167490

  8. Coefficients of caffeine distribution in aliphatic alcohol-ammonium sulfate-water systems

    NASA Astrophysics Data System (ADS)

    Korenman, Ya. I.; Krivosheeva, O. A.; Mokshina, N. Ya.

    2012-11-01

    The extraction of caffeine with aliphatic alcohols C3-C9 from aqueous solutions in the presence of a salting-out agent (ammonium sulfate) is studied. Quantitative characteristics of extraction are calculated: the distribution coefficients ( D) and the degree of recovery ( R, %). Relations are found between log D of caffeine and the length of the hydrocarbon radical in the alcohol molecule, along with certain physicochemical properties of the extragents.

  9. Selective photometric method for the determination of aliphatic amines in air

    SciTech Connect

    Yarym-Agaeva, N.T.; Putilina, O.N.

    1986-09-01

    This paper presents a sensitive, selective, rapid and simple method to determine aliphatic amines in air that insures an operational analysis procedure. The authors used consecutive reactions with hypochlorite and iodide in the presence of starch, proposed for the determination of ethylamine and diethylamine in the liquid phase for the study of the kinetics of the hydrolysis of N-ethylmaleamic and N,N-diethylmaleamic acid. The method is selective in the presence of aromatic amines, isocyanates and ammonia.

  10. IUPAC-NIST Solubility Data Series. 96. Amines with Water Part 3. Non-Aliphatic Amines

    NASA Astrophysics Data System (ADS)

    Góral, Marian; Shaw, David G.; Mański, Andrzej; Wiśniewska-Gocłowska, Barbara; Oracz, Paweł

    2012-12-01

    The mutual solubilities and related liquid-liquid equilibria of 36 binary systems of non-aliphatic amines with water are exhaustively and critically reviewed. Reports of experimental determination of solubility that appeared in the primary literature prior to the end of 2010 are compiled. For 13 systems, sufficient data are available to allow critical evaluation. All data are expressed as mass percent and mole fraction as well as the originally reported units.

  11. Ambient temperature catalyst-free light-induced preparation of macrocyclic aliphatic polyesters.

    PubMed

    Josse, Thomas; Altintas, Ozcan; Oehlenschlaeger, Kim K; Dubois, Philippe; Gerbaux, Pascal; Coulembier, Olivier; Barner-Kowollik, Christopher

    2014-02-25

    The light induced, catalyst-free ambient temperature preparation of macrocyclic aliphatic polyesters is pioneered. Based on the photo-induced Diels-Alder reaction of orthoquinodimethane and acrylate moieties, cyclic polyesters of high purity are readily synthesized. Considering the high tolerance to functional groups and the orthogonality of the ligation, the reported protocol can be easily transferred to a large range of polymers, complex topologies (tadpole, sun-shaped, jellyfish, etc.) and applications. PMID:24413149

  12. Triphosgene-Pyridine Mediated Stereoselective Chlorination of Acyclic Aliphatic 1,3-Diols†

    PubMed Central

    Villalpando, Andrés; Saputra, Mirza A.; Tugwell, Thomas H.; Kartika, Rendy

    2015-01-01

    We describe a strategy to chlorinate stereocomplementary acyclic aliphatic 1,3-diols using a mixture of triphosgene and pyridine. While 1,3-anti diols readily led to 1,3-anti dichlorides, 1,3-syn diols must be converted to 1,3-syn diol monosilylethers to access the corresponding 1,3-syn dichlorides. These dichlorination protocols were operationally simple, very mild, and readily tolerated by advanced synthetic intermediates. PMID:26323232

  13. Chlorinated aliphatic and aromatic VOC decomposition in air mixture by using electron beam irradiation

    NASA Astrophysics Data System (ADS)

    Chmielewski, A. G.; Sun, Yong-Xia; Bułka, S.; Zimek, Z.

    2004-09-01

    Chlorinated aliphatic and aromatic hydrocarbons, which are emitted from coal power station and waste incinerators, are very harmful to the environment and human health. Recent studies show that chlorinated aliphatic and aromatic hydrocarbons are suspected to be the precursors of dioxin's formation. Dioxin's emission into atmosphere will cause severe environmental problems by ecology contamination. l,4-dichlorobenzene(l,4-DCB) and cis-dichloroethylene( cis-DCE) were chosen as representative chlorinated aromatic and aliphatic compounds, respectively. Their decomposition was investigated by electron beam irradiation. The experiments were carried out "in batch" system. It is found that over 97% cis-DCE is decomposed having an initial concentration of 661 ppm. G-values of cis-DCE decomposition vary from 10 to 28 (molecules/100 eV) for initial concentration of 270-1530 ppm cis-DCE. The decomposition is mainly caused by secondary electron attachment and Cl addition reactions. Comparing with cis-DCE, 1,4-DCB decomposition needs higher absorbed dose. G-value of 1,4-DCB is below 4 molecules/100 eV.

  14. Aliphatic, Cyclic, and Aromatic Organic Acids, Vitamins, and Carbohydrates in Soil: A Review

    PubMed Central

    Vranova, Valerie; Rejsek, Klement; Formanek, Pavel

    2013-01-01

    Organic acids, vitamins, and carbohydrates represent important organic compounds in soil. Aliphatic, cyclic, and aromatic organic acids play important roles in rhizosphere ecology, pedogenesis, food-web interactions, and decontamination of sites polluted by heavy metals and organic pollutants. Carbohydrates in soils can be used to estimate changes of soil organic matter due to management practices, whereas vitamins may play an important role in soil biological and biochemical processes. The aim of this work is to review current knowledge on aliphatic, cyclic, and aromatic organic acids, vitamins, and carbohydrates in soil and to identify directions for future research. Assessments of organic acids (aliphatic, cyclic, and aromatic) and carbohydrates, including their behaviour, have been reported in many works. However, knowledge on the occurrence and behaviour of D-enantiomers of organic acids, which may be abundant in soil, is currently lacking. Also, identification of the impact and mechanisms of environmental factors, such as soil water content, on carbohydrate status within soil organic matter remains to be determined. Finally, the occurrence of vitamins in soil and their role in biological and biochemical soil processes represent an important direction for future research. PMID:24319374

  15. The influence of chemical composition of aliphatic-aromatic copolyesters on their properties

    SciTech Connect

    Wojtczak, Malgorzata; Galeski, Andrzej; Piorkowska, Ewa; Dutkiewicz, Slawomir

    2014-05-15

    The chain microstructure and properties of a series of aliphatic-aromatic copolyesters in a range of compositions from 10 to 100% of aromatic components were studied by examining melting and crystallization behaviors, dynamic mechanical response, morphology, wide- (WAXS) and small-angle X-ray scattering (SAXS), and tensile deformation. Chain microstructure was analyzed by {sup 1}H NMR. The results indicate that most of copolyesters used in this study have essentially random distribution of comonomers. Copolyesters with more than 30 mol% of aromatic part crystallize with a crystal structure characteristic for homopolymer poly(butylene terephthalate) (PBT). However, some of the reflections from crystal planes are shifted towards lower diffraction angles as compared to butylene terephthalate homoplymer. The phase transition temperatures decrease with increasing aliphatic content. By means of polarized light microscopy (PLM), small-angle light scattering (SALS) and SAXS, crystallization behavior of a selected aliphatic-aromatic copolyester was further explored. Selected copolyester crystallizes in the form of thin fibrous crystals, few nanometers thick, which is the main factor influencing the depression of its melting temperature.

  16. Olfactory discrimination ability for aliphatic esters in squirrel monkeys and humans.

    PubMed

    Laska, M; Freyer, D

    1997-08-01

    Using a behavioral paradigm designed to simulate olfactory-guided foraging, the ability of five squirrel monkeys to distinguish iso-amyl acetate from n- and iso-forms of other acetic esters (ethyl acetate to decyl acetate) and from other esters carrying the iso-amyl group (iso-amyl propionate to iso-amyl capronate) was investigated. We found (i) that all five animals were clearly able to discriminate between all odor pairs tested; (ii) a significant negative correlation between discrimination performance and structural similarity of odorants in terms of differences in carbon chain length of both the aliphatic alcohol group and the aliphatic acid group of the esters; and (iii) that iso- and n-amyl acetate were perceived as qualitatively similar despite different steric conformation. Using a triple-forced choice procedure, 20 human subjects were tested on the same tasks in parallel and showed a very similar pattern of discrimination performance compared with the squirrel monkeys. Thus, the results of this study provide evidence of well-developed olfactory discrimination ability in squirrel monkeys for aliphatic esters and support the assumption that human and non-human primates may share common principles of odor quality perception. PMID:9279468

  17. New synthetic aliphatic sulfonamido-quaternary ammonium salts as anticancer chemotherapeutic agents.

    PubMed

    Song, Doona; Yang, Jee Sun; Oh, Changmok; Cui, Shuolin; Kim, Bo-Kyung; Won, Misun; Lee, Jang-ik; Kim, Hwan Mook; Han, Gyoonhee

    2013-11-01

    RhoB is expressed during tumor cell proliferation, survival, invasion, and metastasis. In malignant progression, the expression levels of RhoB are commonly attenuated. RhoB is known to be linked to the regulation of the PI3K/Akt survival pathways. Based on aliphatic amido-quaternary ammonium salts that induce apoptosis via up-regulation of RhoB, we synthesized novel aliphatic sulfonamido-quaternary ammonium salts. These new synthetic compounds were evaluated for their biological activities using an in vitro RhoB promoter assay in HeLa cells, and in a growth inhibition assay using human cancer cell lines including PC-3, NUGC-3, MDA-MB-231, ACHN, HCT-15, and NCI-H23. Compound 5b (ethyl-dimethyl-{3-[methyl-(tetradecane-1-sulfonyl)-amino]-propyl}-ammonium; iodide) was the most promising anticancer agent in the series, based upon the potency of growth inhibition and RhoB promotion. These new aliphatic sulfonamido-quaternary ammonium salts could be a valuable series for development of new anticancer chemotherapeutic agents. PMID:24095759

  18. Exploring mild enzymatic sustainable routes for the synthesis of bio-degradable aromatic-aliphatic oligoesters.

    PubMed

    Pellis, Alessandro; Guarneri, Alice; Brandauer, Martin; Acero, Enrique Herrero; Peerlings, Henricus; Gardossi, Lucia; Guebitz, Georg M

    2016-05-01

    The application of Candida antarctica lipase B in enzyme-catalyzed synthesis of aromatic-aliphatic oligoesters is here reported. The aim of the present study is to systematically investigate the most favorable conditions for the enzyme catalyzed synthesis of aromatic-aliphatic oligomers using commercially available monomers. Reaction conditions and enzyme selectivity for polymerization of various commercially available monomers were considered using different inactivated/activated aromatic monomers combined with linear polyols ranging from C2 to C12 . The effect of various reaction solvents in enzymatic polymerization was assessed and toluene allowed to achieve the highest conversions for the reaction of dimethyl isophthalate with 1,4-butanediol and with 1,10-decanediol (88 and 87% monomer conversion respectively). Mw as high as 1512 Da was obtained from the reaction of dimethyl isophthalate with 1,10-decanediol. The obtained oligomers have potential applications as raw materials in personal and home care formulations, for the production of aliphatic-aromatic block co-polymers or can be further functionalized with various moieties for a subsequent photo- or radical polymerization. PMID:26762794

  19. Kinetics of acid-catalyzed aldol condensation reactions of aliphatic aldehydes

    NASA Astrophysics Data System (ADS)

    Casale, Mia T.; Richman, Aviva R.; Elrod, Matthew J.; Garland, Rebecca M.; Beaver, Melinda R.; Tolbert, Margaret A.

    Field observations of atmospheric aerosols have established that organic compounds compose a large fraction of the atmospheric aerosol mass. However, the physical/chemical pathway by which organic compounds are incorporated into atmospheric aerosols remains unclear. The potential role of acid-catalyzed reactions of organic compounds on acidic aerosols has been explored as a possible chemical pathway for the incorporation of organic material into aerosols. In the present study, ultraviolet-visible (UV-vis) spectroscopy was used to monitor the kinetics of formation of the products of the acid-catalyzed aldol condensation reaction of a range of aliphatic aldehydes (C 2-C 8). The experiments were carried out at various sulfuric acid concentrations and a range of temperatures in order to estimate the rate constants of such reactions on sulfuric acid aerosols under tropospheric conditions. The rate constants were generally found to decrease as the chain length of the aliphatic aldehyde increased (except for acetaldehyde, which had an unusually small rate constant), increase as a function of sulfuric acid concentration as predicted by excess acidity theory, and showed normal Arrhenius behavior as a function of temperature. While the kinetic data are generally consistent with previous laboratory reports of aldehyde reactivity in various sulfuric acid media, the aldol condensation reactions involving aliphatic aldehydes do not appear fast enough to be responsible for significant transfer of organic material into atmospheric aerosols.

  20. Aliphatic, cyclic, and aromatic organic acids, vitamins, and carbohydrates in soil: a review.

    PubMed

    Vranova, Valerie; Rejsek, Klement; Formanek, Pavel

    2013-01-01

    Organic acids, vitamins, and carbohydrates represent important organic compounds in soil. Aliphatic, cyclic, and aromatic organic acids play important roles in rhizosphere ecology, pedogenesis, food-web interactions, and decontamination of sites polluted by heavy metals and organic pollutants. Carbohydrates in soils can be used to estimate changes of soil organic matter due to management practices, whereas vitamins may play an important role in soil biological and biochemical processes. The aim of this work is to review current knowledge on aliphatic, cyclic, and aromatic organic acids, vitamins, and carbohydrates in soil and to identify directions for future research. Assessments of organic acids (aliphatic, cyclic, and aromatic) and carbohydrates, including their behaviour, have been reported in many works. However, knowledge on the occurrence and behaviour of D-enantiomers of organic acids, which may be abundant in soil, is currently lacking. Also, identification of the impact and mechanisms of environmental factors, such as soil water content, on carbohydrate status within soil organic matter remains to be determined. Finally, the occurrence of vitamins in soil and their role in biological and biochemical soil processes represent an important direction for future research. PMID:24319374

  1. Self-assembled aliphatic chain extended polyurethane nanobiohybrids: emerging hemocompatible biomaterials for sustained drug delivery.

    PubMed

    Mishra, Abhinay; Singh, Sunil K; Dash, Debabrata; Aswal, Vinod K; Maiti, Biswajit; Misra, Manjusri; Maiti, Pralay

    2014-05-01

    Novel polyurethanes (PUs) have been synthesized using an aliphatic diisocyanate and aliphatic chain extenders with varying chain length. Nanocomposites of PUs have been prepared by dispersing 2-D nanoclay in poly-ol followed by prepolymerization and subsequent chain extension using various chain extenders. Systematic improvement in toughness and adequate enhancement in stiffness in the presence of nanoclay has been observed for PUs with longer chain extenders, and these new classes of nanocomposites exhibit no toughness-stiffness trade-off. Bottom-up self-assembly starting from the molecular level to micron-scale crystallite has been revealed through electronic structure calculation, X-ray diffraction, small-angle neutron scattering, atomic force microscopy and optical images. The role of hydrogen bonding has been revealed for this type of supramolecular assembly, and in the presence of organically modified nanoclay hydrogen bonding contributes to the formation of bigger clusters of nanocomposites. Controlled biodegradation of PU and its nanocomposites has been investigated in enzymatic media. Biocompatibility of these novel nanocomposites has been extensively verified through platelet adhesion, aggregation and hemolysis assay. Sustained drug delivery by biocompatible pristine PU and its nanocomposites has been demonstrated either by controlling the crystallite size of the polyurethane through alteration of the aliphatic chain length of the extender or by incorporating disc-like nanoclay, creating a tortuous path that results in delayed diffusion. Hence, the developed nanohybrids are potential biomaterials for tissue engineering and drug delivery. PMID:24374322

  2. Mechanisms and modeling of halogenated aliphatic contaminant adsorption by carbon nanotubes.

    PubMed

    Apul, Onur Guven; Zhou, Yang; Karanfil, Tanju

    2015-09-15

    This paper examines the adsorption of environmentally relevant halogenated aliphatic compounds using single-walled (SWCNT) and multi-walled carbon nanotubes (MWCNT), and the development of linear solvation-energy relationships (LSER) to examine those adsorption mechanisms. The poly-parameter LSER model was also compared to those previously generated for the adsorption of aromatic compounds by CNTs. The adsorption affinity of aliphatic compounds was greater on the SWCNT than MWCNT with similar oxygen contents. This was attributed to the pore-filling mechanism that was enhanced by higher micropore volume of the SWCNT bundles over the MWCNT bundles. LSER models showed that, at higher concentrations, B (the hydrogen bond accepting ability) was the most influential descriptor for both SWCNT and MWCNT. Other important descriptors were V followed by P, both of which exhibited a positive correlation with adsorption, indicating that their size and polarizability favors adsorption. The contribution of these descriptors to overall adsorption was 2-3 times less than the B. In comparison, V was the most important descriptor in the aromatic compound LSER models. This difference indicates that adsorbate hydrophobicity greatly affects the adsorption of aromatic compounds by CNTs, whereas, aliphatic compounds are affected by both the hydrophobic driving force and other interactions. PMID:25897695

  3. Kinetics of aerobic cometabolic biodegradation of chlorinated and brominated aliphatic hydrocarbons: A review.

    PubMed

    Jesus, João; Frascari, Dario; Pozdniakova, Tatiana; Danko, Anthony S

    2016-05-15

    This review analyses kinetic studies of aerobic cometabolism (AC) of halogenated aliphatic hydrocarbons (HAHs) from 2001-2015 in order to (i) compare the different kinetic models proposed, (ii) analyse the estimated model parameters with a focus on novel HAHs and the identification of general trends, and (iii) identify further research needs. The results of this analysis show that aerobic cometabolism can degrade a wide range of HAHs, including HAHs that were not previously tested such as chlorinated propanes, highly chlorinated ethanes and brominated methanes and ethanes. The degree of chlorine mineralization was very high for the chlorinated HAHs. Bromine mineralization was not determined for studies with brominated aliphatics. The examined research period led to the identification of novel growth substrates of potentially high interest. Decreasing performance of aerobic cometabolism were found with increasing chlorination, indicating the high potential of aerobic cometabolism in the presence of medium- and low-halogenated HAHs. Further research is needed for the AC of brominated aliphatic hydrocarbons, the potential for biofilm aerobic cometabolism processes, HAH-HAH mutual inhibition and the identification of the enzymes responsible for each aerobic cometabolism process. Lastly, some indications for a possible standardization of future kinetic studies of HAH aerobic cometabolism are provided. PMID:26874310

  4. Regulation of Pathogen-Triggered Tryptophan Metabolism in Arabidopsis thaliana by MYB Transcription Factors and Indole Glucosinolate Conversion Products.

    PubMed

    Frerigmann, Henning; Piślewska-Bednarek, Mariola; Sánchez-Vallet, Andrea; Molina, Antonio; Glawischnig, Erich; Gigolashvili, Tamara; Bednarek, Paweł

    2016-05-01

    MYB34, MYB51, and MYB122 transcription factors are known as decisive regulators of indolic glucosinolate (IG) biosynthesis with a strong impact on expression of genes encoding CYP79B2 and CYP79B3 enzymes that redundantly convert tryptophan to indole-3-acetaldoxime (IAOx). This intermediate represents a branching point for IG biosynthesis, and pathways leading to camalexin and indole-carboxylic acids (ICA). Here we investigate how these MYBs affect the pathogen-triggered Trp metabolism. Our experiments indicated that these three MYBs affect not only IG production but also constitutive biosynthesis of other IAOx-derived metabolites. Strikingly, the PENETRATION 2 (PEN2)-dependent IG-metabolism products, which are absent in myb34/51/122 and pen2 mutants, were indispensable for full flg22-mediated induction of other IAOx-derived compounds. However, gene induction and accumulation of ICAs and camalexin upon pathogen infection was not compromised in myb34/51/122 plants, despite strongly reduced IG levels. Hence, in comparison with cyp79B2/B3, which lacks all IAOx-derived metabolites, we found myb34/51/122 an ideal tool to analyze IG contribution to resistance against the necrotrophic fungal pathogen Plectosphaerella cucumerina. The susceptibility of myb34/51/122 was similar to that of pen2, but much lower than susceptibility of cyp79B2/B3, indicating that MYB34/51/122 contribute to resistance toward P. cucumerina exclusively through IG biosynthesis, and that PEN2 is the main leaf myrosinase activating IGs in response to microbial pathogens. PMID:26802248

  5. Regulatory elements mediating transcription from the Drosophila melanogaster actin 5C proximal promoter.

    PubMed Central

    Chung, Y T; Keller, E B

    1990-01-01

    The major cytoskeletal actin gene of Drosophila melanogaster, the actin 5C gene, has two promoters, the proximal one of which controls constitutive synthesis of actin in all growing tissues. To locate regulatory elements required for constitutive activity of the proximal promoter, mutants of this promoter were fused to the bacterial chloramphenicol acetyltransferase gene and assayed for transient expression activity in cultured Drosophila embryonic Schneider line 2 cells. An essential regulatory element has been located 313 base pairs upstream from the cap site. Deletion of this element lowered expression to one-third of the wild-type level. The element has the sequence AAGTTGTAGTTG, as shown by protein-binding footprinting with the reagent methidiumpropyl-EDTA-Fe(II). This element is probably not a general one, since it was not detected in a search of the published 5'-flanking sequences of 27 Drosophila genes. In addition to this regulatory element, there are five GAGA elements in the actin 5C proximal promoter, some or all of which are essential for the promoter activity as shown by an in vivo competition assay. Although this promoter has no classical TATA element, there is an essential promoter region about 35 base pairs upstream from the cap site that could be a TATA surrogate. The promoter also shows sequences homologous to the alcohol dehydrogenase factor 1-binding site and to the core of the vertebrate serum response element, but mutations of these sites did not affect promoter activity in transient expression assays. Images PMID:2104658

  6. Quieting Weinberg 5C: a case study in hospital noise control.

    PubMed

    MacLeod, Mark; Dunn, Jeffrey; Busch-Vishniac, Ilene J; West, James E; Reedy, Anita

    2007-06-01

    Weinberg 5C of Johns Hopkins Hospital is a very noisy hematological cancer unit in a relatively new building of a large medical campus. Because of the requirements for dealing with immuno-suppressed patients, options for introducing sound absorbing materials are limited. In this article, a case study of noise control in a hospital, the sound environment in the unit before treatment is described, the chosen noise control approach of adding custom-made sound absorbing panels is presented, and the impact of the noise control installation is discussed. The treatment of Weinberg 5C involved creating sound absorbing panels of 2-in.-thick fiberglass wrapped in an anti-bacterial fabric. Wallpaper paste was used to hold the fabric to the backing of the fiberglass. Installation of these panels on the ceiling and high on corridor walls had a dramatic effect. The noise on the unit (as measured by the equivalent sound pressure level) was immediately reduced by 5 dB(A) and the reverberation time dropped by a factor of over 2. Further, this drop in background noise and reverberation time understates the dramatic impact of the change. Surveys of staff and patients before and after the treatment indicated a change from viewing the unit as very noisy to a view of the unit as relatively quiet. PMID:17552702

  7. Relationship of the FKBP5 C/T polymorphism with dysfunctional attitudes predisposing to depression.

    PubMed

    Suzuki, Akihito; Matsumoto, Yoshihiko; Sadahiro, Ryoichi; Enokido, Masanori; Goto, Kaoru; Otani, Koichi

    2014-08-01

    FK506-binding protein 51 (FKBP5) is a co-chaperone of the glucocorticoid receptor, and plays an important role in the negative feedback regulation of the hypothalamic-pituitary-adrenal axis. The C/T single nucleotide polymorphism in the intron 2 of the FKBP5 gene affects cortisol secretion, and has been implicated in the pathophysiology of depression. In this study, the relationship of the FKBP5 C/T polymorphism with dysfunctional attitudes predisposing to depression was examined. The subjects were 300 healthy Japanese. The FKBP5 genotypes were determined by a real-time PCR and cycling probe technology for SNP typing. Dysfunctional attitudes were assessed by the 24-item version of the Dysfunctional Attitude Scale (DAS-24), which has the Achievement, Self-control, and Dependency subscales. DAS-24 total scores were significantly higher in the group with the T allele than in that without this allele (p=0.001). Regarding the subscales, scores of the Achievement (p=0.003) and Self-control (p=0.009) subscales, but not those of the Dependency subscale, were significantly higher in the former group than in the latter group. The present study suggests that the FKBP5 C/T polymorphism is implicated in formation of dysfunctional attitudes, especially those about achievement and self-control. PMID:24889341

  8. Multistimuli-Regulated Photochemothermal Cancer Therapy Remotely Controlled via Fe5C2 Nanoparticles.

    PubMed

    Yu, Jing; Ju, Yanmin; Zhao, Lingyun; Chu, Xin; Yang, Wenlong; Tian, Yonglu; Sheng, Fugeng; Lin, Jian; Liu, Fei; Dong, Yunhe; Hou, Yanglong

    2016-01-26

    Stimuli-controlled drug delivery and release is of great significance in cancer therapy, making a stimuli-responsive drug carrier highly demanded. Herein, a multistimuli-controlled drug carrier was developed by coating bovine serum albumin on Fe5C2 nanoparticles (NPs). With a high loading of the anticancer drug doxorubicin, the nanoplatform provides a burst drug release when exposed to near-infrared (NIR) light or acidic conditions. In vitro experiment demonstrated a NIR-regulated cell inhibition that is ascribed from cellular uptake of the carrier and the combination of photothermal therapy and enhanced drug release. The carrier is also magnetic-field-responsive, which enables targeted drug delivery under the guidance of a magnetic field and monitors the theranostic effect by magnetic resonance imaging. In vivo synergistic effect demonstrates that the magnetic-driven accumulation of NPs can induce a complete tumor inhibition without appreciable side effects to the treated mice by NIR irradiation, due to the combined photochemotherapy. Our results highlight the great potential of Fe5C2 NPs as a remote-controlled platform for photochemothermal cancer therapy. PMID:26602632

  9. Structure-Based Design of β5c Selective Inhibitors of Human Constitutive Proteasomes.

    PubMed

    Xin, Bo-Tao; de Bruin, Gerjan; Huber, Eva M; Besse, Andrej; Florea, Bogdan I; Filippov, Dmitri V; van der Marel, Gijsbert A; Kisselev, Alexei F; van der Stelt, Mario; Driessen, Christoph; Groll, Michael; Overkleeft, Herman S

    2016-08-11

    This work reports the development of highly potent and selective inhibitors of the β5c catalytic activity of human constitutive proteasomes. The work describes the design principles, large hydrophobic P3 residue and small hydrophobic P1 residue, that led to the synthesis of a panel of peptide epoxyketones; their evaluation and the selection of the most promising compounds for further analyses. Structure-activity relationships detail how in a logical order the β1c/i, β2c/i, and β5i activities became resistant to inhibition as compounds were diversified stepwise. The most effective compounds were obtained as a mixture of cis- and trans-biscyclohexyl isomers, and enantioselective synthesis resolved this issue. Studies on yeast proteasome structures complexed with some of the compounds provide a rationale for the potency and specificity. Substitution of the N-terminus in the most potent compound for a more soluble equivalent led to a cell-permeable molecule that selectively and efficiently blocks β5c in cells expressing both constitutive proteasomes and immunoproteasomes. PMID:27438186

  10. 26 CFR 5c.168(f)(8)-8 - Loss of section 168(f)(8) protection; recapture.

    Code of Federal Regulations, 2012 CFR

    2012-04-01

    ... 26 Internal Revenue 14 2012-04-01 2012-04-01 false Loss of section 168(f)(8) protection; recapture. 5c.168(f)(8)-8 Section 5c.168(f)(8)-8 Internal Revenue INTERNAL REVENUE SERVICE, DEPARTMENT OF THE TREASURY (CONTINUED) INCOME TAX (CONTINUED) TEMPORARY INCOME TAX REGULATIONS UNDER THE ECONOMIC...

  11. 26 CFR 5c.168(f)(8)-8 - Loss of section 168(f)(8) protection; recapture.

    Code of Federal Regulations, 2013 CFR

    2013-04-01

    ... 26 Internal Revenue 14 2013-04-01 2013-04-01 false Loss of section 168(f)(8) protection; recapture. 5c.168(f)(8)-8 Section 5c.168(f)(8)-8 Internal Revenue INTERNAL REVENUE SERVICE, DEPARTMENT OF THE TREASURY (CONTINUED) INCOME TAX (CONTINUED) TEMPORARY INCOME TAX REGULATIONS UNDER THE ECONOMIC...

  12. 26 CFR 5c.168(f)(8)-8 - Loss of section 168(f)(8) protection; recapture.

    Code of Federal Regulations, 2014 CFR

    2014-04-01

    ... 26 Internal Revenue 14 2014-04-01 2013-04-01 true Loss of section 168(f)(8) protection; recapture. 5c.168(f)(8)-8 Section 5c.168(f)(8)-8 Internal Revenue INTERNAL REVENUE SERVICE, DEPARTMENT OF THE TREASURY (CONTINUED) INCOME TAX (CONTINUED) TEMPORARY INCOME TAX REGULATIONS UNDER THE ECONOMIC...

  13. 26 CFR 5c.168(f)(8)-7 - Reporting of income, deductions and investment tax credit; at risk rules.

    Code of Federal Regulations, 2014 CFR

    2014-04-01

    ... tax credit; at risk rules. 5c.168(f)(8)-7 Section 5c.168(f)(8)-7 Internal Revenue INTERNAL REVENUE... investment tax credit; at risk rules. (a) In general. The fact that the lessor's payments of interest and...) The fair market value of the property at the end of the lease term determined at the beginning of...

  14. 26 CFR 5c.168(f)(8)-7 - Reporting of income, deductions and investment tax credit; at risk rules.

    Code of Federal Regulations, 2013 CFR

    2013-04-01

    ... tax credit; at risk rules. 5c.168(f)(8)-7 Section 5c.168(f)(8)-7 Internal Revenue INTERNAL REVENUE... investment tax credit; at risk rules. (a) In general. The fact that the lessor's payments of interest and...) The fair market value of the property at the end of the lease term determined at the beginning of...

  15. 26 CFR 5c.168(f)(8)-7 - Reporting of income, deductions and investment tax credit; at risk rules.

    Code of Federal Regulations, 2012 CFR

    2012-04-01

    ... tax credit; at risk rules. 5c.168(f)(8)-7 Section 5c.168(f)(8)-7 Internal Revenue INTERNAL REVENUE... investment tax credit; at risk rules. (a) In general. The fact that the lessor's payments of interest and...) The fair market value of the property at the end of the lease term determined at the beginning of...

  16. 26 CFR 5c.168(f)(8)-7 - Reporting of income, deductions and investment tax credit; at risk rules.

    Code of Federal Regulations, 2011 CFR

    2011-04-01

    ... tax credit; at risk rules. 5c.168(f)(8)-7 Section 5c.168(f)(8)-7 Internal Revenue INTERNAL REVENUE... investment tax credit; at risk rules. (a) In general. The fact that the lessor's payments of interest and... lease term. For this purpose, fair market value shall be determined without taking into account...

  17. 26 CFR 5c.168(f)(8)-7 - Reporting of income, deductions and investment tax credit; at risk rules.

    Code of Federal Regulations, 2010 CFR

    2010-04-01

    ... tax credit; at risk rules. 5c.168(f)(8)-7 Section 5c.168(f)(8)-7 Internal Revenue INTERNAL REVENUE... investment tax credit; at risk rules. (a) In general. The fact that the lessor's payments of interest and... lease term. For this purpose, fair market value shall be determined without taking into account...

  18. Effects of Organic and Waste-Derived Fertilizers on Yield, Nitrogen and Glucosinolate Contents, and Sensory Quality of Broccoli (Brassica oleracea L. var. italica).

    PubMed

    Øvsthus, Ingunn; Breland, Tor Arvid; Hagen, Sidsel Fiskaa; Brandt, Kirsten; Wold, Anne-Berit; Bengtsson, Gunnar B; Seljåsen, Randi

    2015-12-23

    Organic vegetable production attempts to pursue multiple goals concerning influence on environment, production resources, and human health. In areas with limited availability of animal manure, there is a need for considering various off-farm nutrient resources for such production. Different organic and waste-derived fertilizer materials were used for broccoli production at two latitudes (58° and 67°) in Norway during two years. The fertilizer materials were applied at two rates of total N (80 and 170 kg ha(-1)) and compared with mineral fertilizer (170 kg ha(-1)) and no fertilizer. Broccoli yield was strongly influenced by fertilizer materials (algae meal < unfertilized control < sheep manure < extruded shrimp shell < anaerobically digested food waste < mineral fertilizer). Yield, but not glucosinolate content, was linearly correlated with estimated potentially plant-available N. However, extruded shrimp shell and mineral NPK fertilizer gave higher glucosinolate contents than sheep manure and no fertilizer. Sensory attributes were less affected by fertilizer material and plant-available N. PMID:26553169

  19. Stilbene 5c, A Microtubule Poison with Vascular Disrupting Properties That Induces Multiple Modes of Growth Arrest and Cell Death

    PubMed Central

    Alotaibi, M.R.; Asnake, B.; Xu, Di; Beckman, M.J.; Durrant, D; Simoni, D; Baruchello, R; Lee, R. M.; Schwartz, E.L.; Gewirtz, D.A.

    2013-01-01

    The stilbene derivative, cis-3, 4’, 5-trimethoxy-3’-aminostilbene (stilbene 5c), is a potentially potent antitumor agent that acts via binding to the colchicine-binding site in tubulin. The current studies were designed to investigate the effectiveness of stilbene 5c against the HCT-116 human colon cancer cell line and B16/F10 melanoma cells as well as human endothelial cell formation and tumor perfusion. Stilbene 5c produced a time-dependent decrease in cell viability in both cell lines and the capacity of the cells to proliferate was not restored upon removal of the drug. Treatment with stilbene 5c also promoted both senescence and autophagy in both cell lines. TUNEL and annexin 5 staining indicated that apoptosis also occurs in stilbene 5c-treated HCT-116 cells, but not in B16/F10 melanoma cells. DAPI staining revealed morphological changes in the cell nuclei (binucleated and micronucleated cells) indicative of mitotic catastrophe in HCT-116 cells but not in the B16/F10 melanoma cells. p53-null HCT-116 cells demonstrated a similar growth arrest/cell death response to stilbene as p53-wild type HCT-116 cells. Stilbene 5c also completely inhibited human endothelial cell tube formation on Matrigel, consistent with potential anti-angiogenic actions. Using a new method developed for monitoring the pharmacodynamic effects of stilbene 5c in vivo, we found that a single injection of stilbene 5c reduced tumor perfusion by 65% at 4 hours, returning to baseline by 24 hours, while subsequent daily injections of stilbene 5c produced progressively larger reductions and smaller rebounds. This work indicates that stilbene 5c could potentially be effective against melanoma and colon cancer through the promotion of multiple modes of growth arrest and cell death coupled with anti-angiogenic and antivascular actions. PMID:24144631

  20. Stilbene 5c, a microtubule poison with vascular disrupting properties that induces multiple modes of growth arrest and cell death.

    PubMed

    Alotaibi, M R; Asnake, B; Di, Xu; Beckman, M J; Durrant, D; Simoni, D; Baruchello, R; Lee, R M; Schwartz, E L; Gewirtz, D A

    2013-12-15

    The stilbene derivative, cis-3,4',5-trimethoxy-3'-aminostilbene (stilbene 5c), is a potentially potent antitumor agent that acts via binding to the colchicine-binding site in tubulin. The current studies were designed to investigate the effectiveness of stilbene 5c against the HCT-116 human colon cancer cell line and B16/F10 melanoma cells as well as human endothelial cell tube formation and tumor perfusion. Stilbene 5c produced a time-dependent decrease in cell viability in both cell lines and the capacity of the cells to proliferate was not restored upon removal of the drug. Treatment with stilbene 5c also promoted both senescence and autophagy in both cell lines. TUNEL and annexin 5 staining indicated that apoptosis also occurs in stilbene 5c-treated HCT-116 cells, but not in B16/F10 melanoma cells. DAPI staining revealed morphological changes in the cell nuclei (binucleated and micronucleated cells) indicative of mitotic catastrophe in HCT-116 cells but not in the B16/F10 melanoma cells. p53-null HCT-116 cells demonstrated a similar growth arrest/cell death response to stilbene as p53-wild type HCT-116 cells. Stilbene 5c also completely inhibited human endothelial cell tube formation on Matrigel, consistent with potential anti-angiogenic actions. Using a new method developed for monitoring the pharmacodynamic effects of stilbene 5c in vivo, we found that a single injection of stilbene 5c reduced tumor perfusion by 65% at 4h, returning to baseline by 24h, while subsequent daily injections of stilbene 5c produced progressively larger reductions and smaller rebounds. This work indicates that stilbene 5c could potentially be effective against melanoma and colon cancer through the promotion of multiple modes of growth arrest and cell death coupled with anti-angiogenic and antivascular actions. PMID:24144631

  1. Metabolic responses of resting man immersed in 25. 5 C and 33 C water

    SciTech Connect

    Weihl, A.C.; Langworthy, H.C.; Manalaysay, A.R.; Layton, R.P.

    1981-02-01

    This study was undertaken to determine the hormonal responses to disabling hypothermia as a result of cold water immersion. Thermally unprotected male divers trained by the U.S. Navy were subjected to total body immersion in water at 25.5 C and 33 C. Plasma epinephrine, norepinephrine, growth hormone, and cortisol were measured. Other variables monitored included oxygen consumption, carbon dioxide production, minute ventilation, and rectal temperature. Immersion without cold stress caused suppression of plasma epinephrine without affecting plasma norepinephrine. Cold stress combined with immersion caused a significant increase in plasma norepinephrine in the absence of other indicators of a generalized stress reaction. The degree of chilling seen in this study will produce disabling hypothermia within 1-2 h and may be shown initially only by an increase in plasma norepinephrine.

  2. Difunctional and heterocyclic products from the ozonolysis of conjugated C sub 5 -C sub 8 cyclodienes

    SciTech Connect

    Griesbaum, K.; In Chan Jung; Mertens, H. )

    1990-11-23

    Ozonolyses of the conjugated C{sub 5}-C{sub 8} cyclodienes 1a-d in methanol, followed by reduction with DMS, have been examined. Monoozonolyses gave the corresponding unsaturated dialdehydes 2e as the primary products. In subsequent reactions, the dialdehydes 2e derived from the monoozonolyses of 1a, 1b, and 1c gave in high yields the heterocyclic compounds 7, 8k, and 9k, respectively. Diozonolyses of 1a-d gave the corresponding dialdehydes 3e as the primary products. In subsequent reactions, the dialdehydes 3e derived from 1b and 1c gave the heterocyclic compounds 8l, and 9l, respectively. In addition, aldehydes 2e and 3e underwent partial acetalization reactions with methanol.

  3. Multiple hydroxyphenethyl glucosinolate isomers and their tandem mass spectrometric distinction in a geographically structured polymorphism in the crucifer Barbarea vulgaris.

    PubMed

    Agerbirk, Niels; Olsen, Carl Erik; Heimes, Christine; Christensen, Stina; Bak, Søren; Hauser, Thure P

    2015-07-01

    Two distinct glucosinolate (GSL) chemotypes (P and G-types) of Barbarea vulgaris (Brassicaceae) were known from southern Scandinavia, but whether the types were consistent in a wider geographic area was not known. Populations (26) from Eastern and Central Europe were analyzed for GSLs in order to investigate whether the two types were consistent in this area. Most (21) could be attributed to one of the previously described GSL profile types, the P-type (13 populations) and the G-type (8 populations), based on differences in the stereochemistry of 2-hydroxylation, presence or absence of phenolic glucobarbarin derivatives, and qualitative differences in indole GSL decoration (tested for a subset of 8+6 populations only). The distinction agreed with previous molecular genetic analysis of the same individuals. Geographically, the P-type typically occurred in Eastern Europe while the G-type mainly occurred in Central Europe. Of the remaining five populations, minor deviations were observed in some individuals from two populations genetically assigned to the G-type, and a hybrid population from Finland contained an additional dihydroxyphenethyl GSL isomer attributed to a combinatorial effect of P-type and G-type genes. Major exceptions to the typical GSL profiles were observed in two populations: (1) A G-type population from Slovenia deviated by a high frequency of a known variant in glucobarbarin biosynthesis ('NAS form') co-occurring with usual G-type individuals. (2) A population from Caucasus exhibited a highly deviating GSL profile dominated by p-hydroxyphenethyl GSL that was insignificant in other accessions, as well as two GSLs investigated by NMR, m-hydroxyphenethylGSL and a partially identified m,p disubstituted hydroxy-methoxy derivative of phenethylGSL. Tandem HPLC-MS of seven NMR-identified desulfoGSLs was carried out and interpreted for increased certainty in peak identification and as a tool for partial structure elucidation. The distinct, geographically

  4. Potential Alternatives Report for Validation of Alternatives to Aliphatic Isocyanate Polyurethanes

    NASA Technical Reports Server (NTRS)

    Lewis, pattie

    2011-01-01

    Identifying and selecting alternative materials and technologies that have the potential to reduce the identified HazMats and hazardous air pollutants (HAPs), while incorporating sound corrosion prevention and control technologies, is a complicated task due to the fast pace at which new technologies emerge and rules change. The alternatives are identified through literature searches, electronic database and Internet searches, surveys, and/or personal and professional contacts. Available test data was then compiled on the proposed alternatives to determine if the materials meet the test objectives or if further)laboratory or field-testing will be required. After reviewing technical information documented in the PAR, government representatives, technical representatives from the affected facilities, and other stakeholders involved in the process will select the list of viable alternative coatings for consideration and testing under the project's Joint Test Protocol entitled Joint Test Protocol for Validation of Alternatives to Aliphatic Isocyanate Polyurethanes and Field Test Plan entitled Field Evaluations Test Plan for Validation of Alternatives to Aliphatic Isocyanate Polyurethanes, both prepared by ITB. Test results will be reported in a Joint Test Report upon completion oftesting. The selection rationale and conclusions are documented in this PAR. A cost benefit analysis will be prepared to quantify the estimated capital and process costs of coating alternatives and cost savings relative to the current coating processes, however, some initial cost data has been included in this PAR. For this coatings project, isocyanates, as found in aliphatic isocyanate polyurethanes, were identified as the target HazMat to be eliminated. Table 1-1 lists the target HazMats, the related process and application, current specifications, and affected programs.

  5. Methyl oleate deoxygenation for production of diesel fuel aliphatic hydrocarbons over Pd/SBA-15 catalysts

    PubMed Central

    2013-01-01

    Background Catalytic deoxygenation is a prominent process for production of renewable fuels from vegetable oil. In this work, deoxygenation of technical grade methyl oleate to diesel fuel aliphatic hydrocarbons (C15 – C18) is evaluated with several parameters including temperature, hydrogen pressure and reaction time in a stirred batch reactor over Pd/SBA-15 catalysts. Results Two different SBA-15 morphologies i.e. spherelike and necklacelike structures have been synthesize as supports for Pd active metal. It is found that Pd dispersion on necklacelike SBA-15 is higher than that of spherelike SBA-15. Notably, higher Pd dispersion on necklacelike SBA-15 provides significant deoxygenation efficiency as compared to Pd/SBA-15-spherelike. Results show that H2 pressures greatly determine the total ester conversion and selectivity to C15 – C18 aliphatic hydrocarbons. Total ester conversions with 55< selectivity to n-heptadecane are achieved using Pd/SBA-15-necklacelike at 270°C and 60 bar H2 pressure within 6 h reaction time. Gas phase study reveals that formation of C17 is generated via indirect decarbonylation when the reaction time is prolonged. Conclusions Pd/SBA-15-necklacelike catalyst exhibits good catalytic performance with high selectivity to diesellike aliphatic hydrocarbons (C15 – C18). The physicochemical properties of the Pd supported on different SBA-15 morphologies influence the deoxygenation activity of the catalysts. Furthermore, the reaction pathways are governed by the H2 pressure as well as reaction duration. PMID:24011181

  6. The galactic distribution of aliphatic hydrocarbons in the diffuse interstellar medium

    NASA Technical Reports Server (NTRS)

    Sandford, Scott A.; Pendleton, Yvonne J.; Allamandola, Louis J.

    1995-01-01

    The infrared absorption feature near 2950(exp -1) (3.4 micron), characteristic of dust in the diffuse interstellar medium (ISM), is attributed to C-H stretching vibrations of aliphatic hydrocarbons. We show here that the strength of the band does not scale linearly with visual extinction everywhere, but instead increases more rapidly for objects near the center of the Galaxy, a behavior that parallels that of the Si-O stretching band due to silicate materials in the diffuse ISM. This implies that the grains responsible for the diffuse medium aliphatic C-H and silicate Si-O stretching bands are different from those responsible for much of the observed visual extinction. It also suggests that the distribution of the carbonaceous component of the diffuse ISM is not uniform throughout the Galaxy, but instead may increase in density toward the center of the Galaxy. The similar behavior of the C-H and Si-O stretching bands suggests that these two components may be coupled, perhaps in the form of silicate-core, organic-mantle grains. Several possible models of the distribution of this material are presented and it is demonstrated that the inner parts of the Galaxy has a carrier density that is 5 to 35 times higher than in the local ISM. Depending on the model used, the density of aliphatic material in the local ISM is found to be about 1 to 2 -CH3 groups m(exp -3) and about 2 to 5 -CH2- groups m(exp -3). These densities are consistent with the strengths of the 2955 and 2925 cm(exp -1) (3.4 micron) band being described by the relations A(sub nu)/tau(sub 2955 cm(exp -1)) = 270 +/- 40 and A(sub nu)/tau(sub 2925 cm(exp -1)) = 250 +/- 40 in the local diffuse ISM.

  7. The Galactic Distribution of Aliphatic Hydrocarbons in the Diffuse Interstellar Medium

    NASA Technical Reports Server (NTRS)

    Sandford, Scott A.; Pendleton, Yvonne J.; Allamandola, Louis J.

    1995-01-01

    The infrared absorption feature near 2950/ cm (3.4 microns), characteristic of dust in the diffuse interstellar medium (ISM), is attributed to C-H stretching vibrations of aliphatic hydrocarbons. We show here that the strength of the band does not scale linearly with visual extinction everywhere, but instead increases more rapidly for objects near the center of the Galaxy, a behavior that parallels that of the Si-O stretching band due to silicate materials in the diffuse ISM. This implies that the grains responsible for the diffuse medium aliphatic C-H and silicate Si-O stretching bands are different from those responsible for much of the observed visual extinction. It also suggests that the distribution of the carbonaceous component of the diffuse ISM is not uniform throughout the Galaxy, but instead may increase in density toward the center of the Galaxy. The similar behavior of the C-H and Si-O stretching bands suggests that these two components may be coupled, perhaps in the form of silicate-core, organic-mantle grains. Several possible models of the distribution of this material are presented and it is demonstrated that the inner parts of the Galaxy has a carrier density that is 5 to 35 times higher than in the local ISM. Depending on the model used, the density of aliphatic material in the local ISM is found to be about 1 to 2 -CH3 groups /cc and about 2 to 5 -CH2- groups/cc. These densities are consistent with the strengths of the 2955 and 2925/ cm (3.38 and 3.42 microns) subfeatures (due to -CH3 and -CH2- groups, respectively) within the overall 2950/ cm (3.4 microns) band being described by the relations A(sub upsilon)/tau(sub 2925/cm) = 270 +/- 40 and A(sub upsilon)/tau(sub 2925/cm) = 250 +/- 40 in the local diffuse ISM.

  8. Palladium-catalysed C-H activation of aliphatic amines to give strained nitrogen heterocycles

    NASA Astrophysics Data System (ADS)

    McNally, Andrew; Haffemayer, Benjamin; Collins, Beatrice S. L.; Gaunt, Matthew J.

    2014-06-01

    The development of new chemical transformations based on catalytic functionalization of unactivated C-H bonds has the potential to simplify the synthesis of complex molecules dramatically. Transition metal catalysis has emerged as a powerful tool with which to convert these unreactive bonds into carbon-carbon and carbon-heteroatom bonds, but the selective transformation of aliphatic C-H bonds is still a challenge. The most successful approaches involve a `directing group', which positions the metal catalyst near a particular C-H bond, so that the C-H functionalization step occurs via cyclometallation. Most directed aliphatic C-H activation processes proceed through a five-membered-ring cyclometallated intermediate. Considering the number of new reactions that have arisen from such intermediates, it seems likely that identification of distinct cyclometallation pathways would lead to the development of other useful chemical transformations. Here we report a palladium-catalysed C-H bond activation mode that proceeds through a four-membered-ring cyclopalladation pathway. The chemistry described here leads to the selective transformation of a methyl group that is adjacent to an unprotected secondary amine into a synthetically versatile nitrogen heterocycle. The scope of this previously unknown bond disconnection is highlighted through the development of C-H amination and carbonylation processes, leading to the synthesis of aziridines and β-lactams (respectively), and is suggestive of a generic C-H functionalization platform that could simplify the synthesis of aliphatic secondary amines, a class of small molecules that are particularly important features of many pharmaceutical agents.

  9. Adsorption properties of hyperbranched aliphatic polyester grafted attapulgite towards heavy metal ions.

    PubMed

    Liu, Peng; Wang, Tingmei

    2007-10-01

    The AB(2) type monomer, 2,2-bis (hydroxymethyl) propionic acid (bis-MPA), was successfully grafted from the surfaces of the amino groups modified attapulgite nano-fibrillar clay (A-ATP) via a melt polycondensation method with p-toluenesulfonic acid (p-TSA) as catalyst. The competitive adsorption properties of the hyperbranched aliphatic polyester grafted attapulgite (HAPE-ATP) towards the heavy metal ions (Cu(II), Hg(II), Zn(II), and Cd(II)) were investigated preliminarily. PMID:17467898

  10. Use of aliphatic hydrocarbons in feed to decrease body burdens of lipophilic toxicants in livestock

    SciTech Connect

    Rozman, K.; Rozman, T.; Griem, H.; Nieman, I.J.; Smith, G.S.

    1982-01-01

    Sheep were contaminated with hexachlorobenzene and then fed a conventional diet with or without 5% mineral oil or hexadecane. Similar to nonruminant species, both treatments enhanced fecal excretion of hexachlorobenzene about 3-fold and reduced levels of hexachlorobenzene stored in adipose tissue. Normal digestive functions of the animals, including fiber digestion by rumen microbes, were not affected by the administration of the aliphatic hydrocarbons. Dietary administration of mineral oil could be an inexpensive way to save livestock contaminated with toxic lipophilic compounds, such as many pesticides and industrial chemicals.

  11. The fumigant and repellent activity of aliphatic lactones against Pediculus humanus capitis (Anoplura: Pediculidae).

    PubMed

    Toloza, Ariel Ceferino; Zygadlo, Julio; Mougabure-Cueto, Gastón; Zerba, Eduardo; Faillaci, Silvina; Picollo, María Inés

    2006-02-01

    New alternative insecticides are necessary for the chemical control of head lice. In this study the fumigant knockdown time 50% (KT50) and repellency index (RI) of three aliphatic lactones was compared with two essential oils and DDVP, against permethrin-resistance Pediculus humanus capitis from Argentina. In the fumigant assay, none of the lactones were effective compared to the highest activity of eucalyptus (KT50 15.53 m). In the repellency test, the three lactones were equally or more effective (RI ranging from 60.50 to 76.68) than the positive control (piperonal). These lactones are promising as head lice repellents. PMID:16699710

  12. Iron-Catalyzed Oxyfunctionalization of Aliphatic Amines at Remote Benzylic C-H Sites.

    PubMed

    Mbofana, Curren T; Chong, Eugene; Lawniczak, James; Sanford, Melanie S

    2016-09-01

    We report the development of an iron-catalyzed method for the selective oxyfunctionalization of benzylic C(sp(3))-H bonds in aliphatic amine substrates. This transformation is selective for benzylic C-H bonds that are remote (i.e., at least three carbons) from the amine functional group. High site selectivity is achieved by in situ protonation of the amine with trifluoroacetic acid, which deactivates more traditionally reactive C-H sites that are α to nitrogen. The scope and synthetic utility of this method are demonstrated via the synthesis and derivatization of a variety of amine-containing, biologically active molecules. PMID:27529646

  13. Aliphatic and polycyclic aromatic hydrocarbons in sediments of the Slovenian coastal area (Gulf of Trieste, northern Adriatic).

    PubMed

    Bajt, Oliver

    2012-12-01

    The distribution and sources of aliphatic and polycyclic aromatic hydrocarbons (PAH) were determined in sediments at seven sites around the Slovenian coastal area. The potential toxicological significance was also assessed using biological thresholds. The results of the analyses showed higher concentrations of hydrocarbons in the Port of Koper and in the Marina of Portoroz. The influence of pollution was also evident in rather higher concentrations of hydrocarbons in the surrounding area in the Bays of Koper and Piran. Concentrations of hydrocarbons decrease toward the central part of the Gulf of Trieste. The major component of the aliphatic fraction was the unresolved complex mixture. Concentrations of the total resolved aliphatic hydrocarbons were in a range from 689 to 3,164 ng g(-1). Concentrations of the total PAHs were between 330 and 1,173 ng g(-1). Polycyclic aromatic hydrocarbons are primarily of pyrolytic origin with some smaller contributions of the petrogenic, while the aliphatic are mostly of petrogenic origin with significant amounts of biogenic derived compounds of terrestrial and marine origin. Strong evidence of the diagenetic origin of perylene in the investigated area was also found. Quite a good linear relationship between PAH concentration and TOC and between aliphatic hydrocarbon concentrations and TOC was observed. The principal component analysis showed differences between the nearshore and offshore sites. In general, the investigated area is moderately contaminated by hydrocarbons. Concentrations of PAHs, hydrocarbons of high concern, are below the levels (effects range low and the effects range median) associated with adverse biological effects. PMID:22270593

  14. Process for removing halogenated aliphatic and aromatic compounds from petroleum products. [Polychlorinated biphenyls; methylene chloride; perchloroethylene; trichlorofluoroethane; trichloroethylene; chlorobenzene

    DOEpatents

    Googin, J.M.; Napier, J.M.; Travaglini, M.A.

    1982-03-31

    A process for removing halogenated aliphatic and aromatic compounds, e.g., polychlorinated biphenyls, from petroleum products by solvent extraction. The halogenated aliphatic and aromatic compounds are extracted from a petroleum product into a polar solvent by contracting the petroleum product with the polar solvent. The polar solvent is characterized by a high solubility for the extracted halogenated aliphatic and aromatic compounds, a low solubility for the petroleum product and considerable solvent power for polyhydroxy compound. The preferred polar solvent is dimethylformamide. A miscible polyhydroxy compound, such as, water, is added to the polar extraction solvent to increase the polarity of the polar extraction solvent. The halogenated aliphatic and aromatic compounds are extracted from the highly-polarized mixture of polyhydroxy compound and polar extraction solvent into a low polar or nonpolar solvent by contacting the polyhydroxy compound-polar solvent mixture with the low polar or nonpolar solvent. The halogenated aliphatic and aromatic compounds in the low polar or nonpolar solvent by physical means, e.g., vacuum evaporation. The polar and nonpolar solvents are recovered for recycling. The process can easily be designed for continuous operation. Advantages of the process include that the polar solvent and a major portion of the nonpolar solvent can be recycled, the petroleum products are reclaimable and the cost for disposing of waste containing polychlorinated biphenyls is significantly reduced. 2 tables.

  15. Fabrication of n-type nickel doped B{sub 5}C{sub 1+{delta}} homojunction and heterojunction diodes

    SciTech Connect

    Hwang, S.; Yang, K.; Dowben, P.A.; Ahmad, A.A.; Ianno, N.J.; Li, J.Z.; Lin, J.Y.; Jiang, H.X.; McIlroy, D.N.

    1997-02-01

    We have successfully nickel doped a boron carbide (B{sub 5}C) alloy film. The nickel doped boron-carbide (Ni-B{sub 5}C{sub 1+{delta}}) thin films were fabricated from a single source carborane cage molecule and nickelocene [Ni(C{sub 5}H{sub 5}){sub 2}] using plasma enhanced chemical vapor deposition. Nickel doping transforms the highly resistive undoped film from a p-type material to an n-type material. This has been verified from the characteristics of diodes constructed of Ni-B{sub 5}C{sub 1+{delta}} on both n-type silicon and p-type B{sub 5}C. The homojunction diodes exhibit excellent rectifying properties over a wide range of temperatures. {copyright} {ital 1997 American Institute of Physics.}

  16. Evidence of high sea level during isotope stage 5c in Queensland, Australia

    NASA Astrophysics Data System (ADS)

    Pickett, J. W.; Thompson, C. H.; Kelley, R. A.; Roman, D.

    1985-07-01

    Thirty-nine species of scleractinian corals have been recovered from under a high dune on the western (mainland) side of North Stradbroke Island, eastern Australia. The corals are associated with thin intertidal sediments and their good condition implies burial in situ and preservation in a saturated zone. Most likely this occurred as the coast prograded and a large dune advanced into the littoral zone, burying intertidal sediments and coral. The species assemblage indicates a sheltered environment but one open to the ocean without wide fluctuations in salinity. Three species yielded a mean {230Th}/{234U} age of 105,000 yr B.P. which is significantly younger than the nearest Pleistocene corals at Evans Head, New South Wales. The corals provide evidence of a sea stand near present sea level during isotope Stage 5c, which is considerably higher than previously suggested for this period. Their good condition implies that the overlying parabolic dune is of comparable age and formed during that high stand of sea level. Also, the isotope age provides a maximum period for the development of giant podzols in the podzol chronosequences on coastal dunes in southern Queensland.

  17. Positive and negative regulatory elements mediating transcription from the Drosophila melanogaster actin 5C distal promoter.

    PubMed Central

    Chung, Y T; Keller, E B

    1990-01-01

    The major cytoskeletal actin gene of Drosophila melanogaster, the actin 5C gene, has two promoters, the distal one of which controls synthesis of actin in a tissue- and developmental stage-specific manner. This very strong promoter has widely been used for expression of heterologous genes in cultured cells. To locate functional regulatory elements in this distal promoter, mutants of the promoter were fused to the bacterial chloramphenicol acetyltransferase gene and assayed for transient expression activity in cultured Drosophila embryonic Schneider line 2 cells. The results showed that the upstream end of the promoter extends to 522 bp from the transcription start site. In addition, there are two remote activating regions about 2 kb upstream. Between -522 and -379 are two regions that exert a strong negative effect. Downstream from these negative regions are at least six positive regions and a TATA element. The strongest positive determinant of the promoter was identified at -320 as AAAATGTG by footprinting and by a replacement experiment. When the relevant region was replaced by a synthetic sequence containing this element in a random context, the transient expression activity was restored. The sequence TGTATG located at -355 was also identified as a positive element by a similar replacement approach. Apparently the very high activity of this promoter is the result of the combined activities of multiple factors. Images PMID:2123290

  18. Quantitative separation of aliphatic and aromatic hydrocarbons using silver ion--silica solid-phase extraction

    PubMed

    Bennett; Larter

    2000-03-01

    A solid-phase extraction (SPE) method employing silver nitrate impregnated silica has been developed and evaluated for the separation of defined aliphatic and aromatic hydrocarbons from crude oils. The versatility of the SPE method is demonstrated using a light crude oil from the North Sea and a heavy crude oil from Orcutt field (Monterey, California, U.S.A.). The coefficients of variation for a number of geochemical parameters measured on both aliphatic and aromatic hydrocarbons were excellent. The separation efficiency of SPE is demonstrated using quantification of monoaromatic steroid hydrocarbons which are notoriously difficult to efficiently sequester into the aromatic hydrocarbon fraction using traditional liquid chromatographic procedure. The selectivity and efficiency of the SPE technique is comparable with that of silica gel TLC. However, losses of volatile compounds such as naphthalene are limited during SPE since the sample remains in solvent. We conclude that solid-phase extraction affords rapid sample turnover suitable for processing large sample numbers with high reproducibility. PMID:10739209

  19. Two new aliphatic lactones from the fruits of Coriandrum sativum L.

    PubMed Central

    2012-01-01

    Background The present paper describes the isolation and characterization of two new aliphatic δ-lactones along with three glycerides and n-nonadecanyl cetoleate from the fruits of Coriandrum sativum L. (Apiaceae). The structures of all the isolated phytoconstituents have been established on the basis of spectral data analysis and chemical reactions. Results Phytochemical investigation of the methanolic extract of C. sativum L. (Apiaceae) fruits resulted in the isolation of two new aliphatic δ-lactones characterized as 2α-n-heptatriacont-(Z)-3-en-1,5-olide (1) (coriander lactone) and 2α-n-tetracont-(Z,Z)-3,26-dien-18α-ol-1,5-olide (2) (hydroxy coriander lactone) together with glyceryl-1,2-dioctadec-9,12-dienoate-3-octadec-9-enoate (3); glyceryl-1,2,3-trioctadecanoate (4); n-nonadecanyl-n-docos-11-enoate (5) and oleiyl glucoside (6). Conclusions Phytochemical investigation of the methanolic extract of C. sativum gave coriander lactone and hydroxy coriander lactone as the new phytoconstituents. PMID:22800677

  20. Halides with Fifteen Aliphatic C-H···Anion Interaction Sites.

    PubMed

    Shi, Genggongwo; Aliakbar Tehrani, Zahra; Kim, Dongwook; Cho, Woo Jong; Youn, Il-Seung; Lee, Han Myoung; Yousuf, Muhammad; Ahmed, Nisar; Shirinfar, Bahareh; Teator, Aaron J; Lastovickova, Dominika N; Rasheed, Lubna; Lah, Myoung Soo; Bielawski, Christopher W; Kim, Kwang S

    2016-01-01

    Since the aliphatic C-H···anion interaction is relatively weak, anion binding using hydrophobic aliphatic C-H (Cali-H) groups has generally been considered not possible without the presence of additional binding sites that contain stronger interactions to the anion. Herein, we report X-ray structures of organic crystals that feature a chloride anion bound exclusively by hydrophobic Cali-H groups. An X-ray structure of imidazolium-based scaffolds using Cali-H···A(-) interactions (A(-) = anion) shows that a halide anion is directly interacting with fifteen Cali-H groups (involving eleven hydrogen bonds, two bidentate hydrogen-bond-type binding interactions and two weakly hydrogen-bonding-like binding interactions). Additional supporting interactions and/or other binding sites are not observed. We note that such types of complexes may not be rare since such high numbers of binding sites for an anion are also found in analogous tetraalkylammonium complexes. The Cali-H···A(-) interactions are driven by the formation of a near-spherical dipole layer shell structure around the anion. The alternating layers of electrostatic charge around the anion arise because the repulsions between weakly positively charged H atoms are reduced by the presence of the weakly negatively charged C atoms connected to H atoms. PMID:27444513

  1. Exploring 3D structural influences of aliphatic and aromatic chemicals on α-cyclodextrin binding.

    PubMed

    Linden, Lukas; Goss, Kai-Uwe; Endo, Satoshi

    2016-04-15

    Binding of solutes to macromolecules is often influenced by steric effects caused by the 3D structures of both binding partners. In this study, the 1:1 α-cyclodextrin (αCD) binding constants (Ka1) for 70 organic chemicals were determined to explore the solute-structural effects on the αCD binding. Ka1 was measured using a three-part partitioning system with either a headspace or a passive sampler serving as the reference phase. The Ka1 values ranged from 1.08 to 4.97 log units. The results show that longer linear aliphatic chemicals form more stable complexes than shorter ones, and that the position of the functional group has a strong influence on Ka1, even stronger than the type of the functional group. Comparison of linear and variously branched aliphatic chemicals indicates that having a sterically unhindered alkyl chain is favorable for binding. These results suggest that only one alkyl chain can enter the binding cavity. Relatively small aromatic chemicals such as 1,3-dichlorobenzene bind to αCD well, while larger ones like tetrachlorobenzene and 3-ring aromatic chemicals show only a weak interaction with αCD, which can be explained by cavity exclusion. The findings of this study help interpret cyclodextrin binding data and facilitate the understanding of binding processes to macromolecules. PMID:26826354

  2. New aliphatic glycerophosphoryl-containing polyurethanes: synthesis, platelet adhesion and elution cytotoxicity studies.

    PubMed

    Acetti, Daniela; D'Arrigo, Paola; Giordano, Carmen; Macchi, Piero; Servi, Stefano; Tessaro, Davide

    2009-04-01

    in this study new poly(ether)urethanes (PeUs) based on aliphatic diisocyanates were synthesized with phospholipid-like residues as chain extenders. The primary objective was to prepare new polyurethanes from diisocyanates that are less toxic than the aromatic ones widely used in medical-grade polyurethanes, in order to investigate the effect of the different aromatic or aliphatic hard segment content on the final properties of the materials. Some glycerophospho residues were simultaneously introduced to enhance the hemocompatibility of these materials. Polymers were prepared by a conventional two-step solution polymerization procedure using hexamethylene diisocyanate (HDi) and dodecametilendiisocyanate (DDi) and poly(1,4-butanediol) with molecular weight 1000 to form prepolymers, which were subsequently polymerized with 1-glycerophosphorylcholine (1-GPC) or glycerophosphorylserine (GPS) to act as chain extenders. The reference polymers bearing 1,4-butandiol (BD) were also synthesized. The polymers obtained were characterized by fourier transform infrared spectroscopy (fT-iR), nuclear magnetic resonance (1H nmR), and differential scanning calorimetry (DSC). The hemocompatibility of synthesized segmented polyurethanes was preliminarily investigated by platelet-rich plasma contact studies and related scanning electron microscopy (Sem) photographs as well as by cell viability assay after cell exposure to material elutions to assess the effect of any toxic leachables coming out from the samples. Two of the polymers gave interesting results, suggesting the desirability of further investigation into their possible use in biomedical devices. PMID:19569028

  3. Computation of Bond Dissociation Energies for Removal of Nitrogen Dioxide Groups in Certain Aliphatic Nitro Compounds

    NASA Astrophysics Data System (ADS)

    Shao, Ju-Xiang; Cheng, Xin-Lu; Yang, Xiang-Dong; Xiang, Shi-Kai

    2006-04-01

    Bond dissociation energies for removal of nitrogen dioxide groups in 10 aliphatic nitro compounds, including nitromethane, nitroethylene, nitroethane, dinitromethane, 1-nitropropane, 2-nitropropane, 1-nitrobutane, 2-methyl-2-nitropropane, nitropentane, and nitrohexane, are calculated using the highly accurate complete basis set (CBS-Q) and the three hybrid density functional theory (DFT) methods B3LYP, B3PW91 and B3P86 with 6-31G** basis set. By comparing the computed bond dissociation energies and experimental results, we find that the B3LYP/6-31G** and B3PW91/6-31G** methods are incapable of predicting the satisfactory bond dissociation energy (BDE). However, B3P86/6-31G** and CBS-Q computations are capable of giving the calculated BDEs, which are in extraordinary agreement with the experimental data. Nevertheless, since CBS-Q computational demands increase rapidly with the number of containing atoms in molecules, larger molecules soon become prohibitively expensive. Therefore, we suggest to take the B3P86/6-31G** method as a reliable method of computing the BDEs for removal of the NO2 groups in the aliphatic nitro compounds.

  4. Halides with Fifteen Aliphatic C–H···Anion Interaction Sites

    NASA Astrophysics Data System (ADS)

    Shi, Genggongwo; Aliakbar Tehrani, Zahra; Kim, Dongwook; Cho, Woo Jong; Youn, Il-Seung; Lee, Han Myoung; Yousuf, Muhammad; Ahmed, Nisar; Shirinfar, Bahareh; Teator, Aaron J.; Lastovickova, Dominika N.; Rasheed, Lubna; Lah, Myoung Soo; Bielawski, Christopher W.; Kim, Kwang S.

    2016-07-01

    Since the aliphatic C–H···anion interaction is relatively weak, anion binding using hydrophobic aliphatic C–H (Cali–H) groups has generally been considered not possible without the presence of additional binding sites that contain stronger interactions to the anion. Herein, we report X-ray structures of organic crystals that feature a chloride anion bound exclusively by hydrophobic Cali–H groups. An X-ray structure of imidazolium-based scaffolds using Cali–H···A‑ interactions (A‑ = anion) shows that a halide anion is directly interacting with fifteen Cali–H groups (involving eleven hydrogen bonds, two bidentate hydrogen-bond-type binding interactions and two weakly hydrogen-bonding-like binding interactions). Additional supporting interactions and/or other binding sites are not observed. We note that such types of complexes may not be rare since such high numbers of binding sites for an anion are also found in analogous tetraalkylammonium complexes. The Cali–H···A‑ interactions are driven by the formation of a near-spherical dipole layer shell structure around the anion. The alternating layers of electrostatic charge around the anion arise because the repulsions between weakly positively charged H atoms are reduced by the presence of the weakly negatively charged C atoms connected to H atoms.

  5. Direct nitration and azidation of aliphatic carbons by an iron-dependent halogenase

    PubMed Central

    Chang, Wei-chen; Layne, Andrew P; Miles, Linde A; Krebs, Carsten

    2014-01-01

    Iron-dependent halogenases employ cis-halo-Fe(IV)-oxo (haloferryl) complexes to functionalize unactivated aliphatic carbon centers, a capability elusive to synthetic chemists. Halogenation requires (1) coordination of a halide anion (Cl− or Br−) to the enzyme's Fe(II) cofactor; (2) coupled activation of O2 and decarboxylation of α-ketoglutarate to generate the haloferryl intermediate; (3) abstraction of hydrogen (H•) from the substrate by the ferryl oxo group; and (4) transfer of the cis halogen as Cl• or Br• to the substrate radical. This enzymatic solution to an unsolved chemical challenge is potentially generalizable to installation of other functional groups, provided that the corresponding anions can support the four requisite steps. We show here that the wild-type halogenase SyrB2 can indeed direct aliphatic nitration and azidation reactions by the same chemical logic. The discovery and enhancement by mutagenesis of these previously unknown reaction types suggests unrecognized or untapped versatility in ferryl-mediated enzymatic C–H-bond activation. PMID:24463698

  6. Anaerobic biotransformation of chlorinated aliphatic hydrocarbons: Ugly duckling to beautiful swan

    SciTech Connect

    Parkin, G.F.

    1999-10-01

    For many years anaerobic biological processes were reputed to be more sensitive than aerobic processes to toxic substances such as chlorinated aliphatic hydrocarbons (CAH) and thus a poor choice for treating water containing these compounds. This was especially true for water containing perchloroethylene (PCE) or trichloroethylene (TCE) because vinyl chloride, a human carcinogen, is produced when these two compounds are degraded anaerobically. Aerobic treatment with organisms containing oxygenase enzyme systems, which could fortuitously degrade a wide variety of chlorinated aliphatics (but not PCE), was favored. Recently, however, several enrichments and organisms have been isolated that will convert PCE and TCE into ethene and ethane, as shown by field data. Because of this evidence, anaerobic processes are now considered a significant alternative treatment for CAH contamination. Recent work at the University of Iowa, Iowa City, has focused on the effect of mixtures of CAHs on biotransformation of individual organic compounds and the potential for a combined methanogen-iron (Fe(0)) system to improve CAH bioremediation. At the concentration ranges tested, the presence of a mixture of CAHs seems to decrease rate of transformation of individual organics. However, there are important exceptions; in some cases a mixture of CAHs seems to facilitate transformation of an individual organic compound. Combination of an active methanogenic population with Fe(0) increases the rate and extent of transformation of carbon tetrachloride and chloroform. Results with PCE and 1,1,1-trichloroethane are less clear.

  7. Mixed aromatic-aliphatic organic nanoparticles as carriers of unidentified infrared emission features

    NASA Astrophysics Data System (ADS)

    Kwok, Sun; Zhang, Yong

    2011-11-01

    Unidentified infrared emission bands at wavelengths of 3-20 micrometres are widely observed in a range of environments in our Galaxy and in others. Some features have been identified as the stretching and bending modes of aromatic compounds, and are commonly attributed to polycyclic aromatic hydrocarbon molecules. The central argument supporting this attribution is that single-photon excitation of the molecule can account for the unidentified infrared emission features observed in `cirrus' clouds in the diffuse interstellar medium. Of the more than 160 molecules identified in the circumstellar and interstellar environments, however, not one is a polycyclic aromatic hydrocarbon molecule. The detections of discrete and broad aliphatic spectral features suggest that the carrier of the unidentified infrared emission features cannot be a pure aromatic compound. Here we report an analysis of archival spectroscopic observations and demonstrate that the data are most consistent with the carriers being amorphous organic solids with a mixed aromatic-aliphatic structure. This structure is similar to that of the organic materials found in meteorites, as would be expected if the Solar System had inherited these organic materials from interstellar sources.

  8. Hyperbranched Aliphatic Polyester Modified Activated Carbon Particles with Homogenized Surface Groups

    NASA Astrophysics Data System (ADS)

    Liu, Peng; Zhang, Liuxue

    The hyperbranched aliphatic polyester grafted activated carbon (HAPE-AC), was successfully prepared by the simple "one-pot" method. The surface functional groups of commercial activated carbon particles were homogenized to hydroxyl groups by being oxidized with nitric acid and then reduced with lithium tetrahydroaluminate (LiAlH4) at first. Secondly, the surface hydroxyl groups were used as the active sites for the solution polycondensation of the AB2 monomer, 2, 2-bis(hydroxymethyl)propionic acid (bis-MPA), with the catalysis of p-toluenesulfonic acid (p-TSA). The homogenization of the surface groups of the activated carbon particles and the graft polymerization of the hyperbranched aliphatic polyester were investigated by X-ray photoelectron spectroscopy (XPS) technique. The products were also characterized with Fourier transform infrared (FT-IR) and scanning electron microscope (SEM). The competitive adsorption properties of the products toward the heavy metal ions (Cu(II), Hg(II), Zn(II), and Cd(II)) also proved the translations of the surface groups.

  9. Determination of aliphatic aldehydes by liquid chromatography with pulsed amperometric detection.

    PubMed

    Casella, Innocenzo G; Contursi, Michela

    2005-01-21

    An electrochemical detection method for short-chain saturated and unsaturated aliphatic aldehydes separated by liquid chromatography in moderately acidic medium is described. A triple-step waveform of the potentials applied to the polycrystalline platinum electrode, is proposed for sensitive detection of aliphatic aldehydes in flowing streams avoiding tedious pre- or post-column derivatization and/or cleanup procedures. The influences of the perchloric acid concentration and dissolved oxygen in the mobile phase, on the amperometric and chromatographic performance were evaluated and considered in terms of sensitivity and selectivity. Under the optimised experimental conditions (i.e., deoxygenated 50mM HClO4) the proposed analytical method allowed detection limits between 0.2 microM for acrolein and 2.5 microM for valeraldehyde. Regression analysis of calibration data indicates that responses for all investigated compounds are linear over about 2 orders of magnitude above the LOD, with correlation coefficients >0.990. The method was successfully applied to the determination of formaldehyde, acetaldehyde, propionaldehyde and acrolein in real matrices such as spiked water and red wines with good mean recoveries (81-97%). PMID:15700464

  10. Mixed aromatic-aliphatic organic nanoparticles as carriers of unidentified infrared emission features.

    PubMed

    Kwok, Sun; Zhang, Yong

    2011-11-01

    Unidentified infrared emission bands at wavelengths of 3-20 micrometres are widely observed in a range of environments in our Galaxy and in others. Some features have been identified as the stretching and bending modes of aromatic compounds, and are commonly attributed to polycyclic aromatic hydrocarbon molecules. The central argument supporting this attribution is that single-photon excitation of the molecule can account for the unidentified infrared emission features observed in 'cirrus' clouds in the diffuse interstellar medium. Of the more than 160 molecules identified in the circumstellar and interstellar environments, however, not one is a polycyclic aromatic hydrocarbon molecule. The detections of discrete and broad aliphatic spectral features suggest that the carrier of the unidentified infrared emission features cannot be a pure aromatic compound. Here we report an analysis of archival spectroscopic observations and demonstrate that the data are most consistent with the carriers being amorphous organic solids with a mixed aromatic-aliphatic structure. This structure is similar to that of the organic materials found in meteorites, as would be expected if the Solar System had inherited these organic materials from interstellar sources. PMID:22031328

  11. Aliphatic esters as targets of esterase activity in the parsnip webworm (Depressaria pastinacella).

    PubMed

    Zangerl, Arthur R; Liao, Ling-Hsiu; Jogesh, Tania; Berenbaum, May R

    2012-02-01

    As a specialist on the reproductive structures of Pastinaca sativa and species in the related genus Heracleum, the parsnip webworm (Depressaria pastinacella) routinely encounters a distinctive suite of phytochemicals in hostplant tissues. Little is known, however, about the detoxification mechanisms upon which this species relies to metabolize these compounds. In this study, larval guts containing hostplant tissues were homogenized, and metabolism was determined by incubating reactions with and without NADPH and analyzing for substrate disappearance and product appearance by gas chromatography-mass spectrometry. Using this approach, we found indications of carboxylesterase activity, in the form of appropriate alcohol metabolites for three aliphatic esters in hostplant tissues-octyl acetate, octyl butyrate, and hexyl butyrate. Involvement of webworm esterases in hostplant detoxification subsequently was confirmed with metabolism assays with pure compounds. This study is the first to implicate esterases in lepidopteran larval midgut metabolism of aliphatic esters, ubiquitous constituents of flowers and fruits. In addition, this method confirmed that webworms detoxify furanocoumarins and myristicin in their hostplants via cytochrome P450-mediated metabolism, and demonstrated that these enzymes also metabolize the coumarin osthol and the fatty acid derivative palmitolactone. PMID:22350520

  12. Kinetics of Acid-Catalyzed Aldol Condensation Reactions of Aliphatic Aldehydes

    NASA Astrophysics Data System (ADS)

    Elrod, M. J.; Casale, M. T.; Richman, A. R.; Beaver, M. R.; Garland, R. M.; Tolbert, M. A.

    2006-12-01

    While it is well established that organic compounds compose a large fraction of the atmospheric aerosol mass, the mechanisms through which organics are incorporated into atmospheric aerosols are not well understood. Acid-catalyzed reactions of compounds with carbonyl groups have recently been suggested as important pathways for transfer of volatile organics into acidic aerosols. In the present study, ultraviolet-visible (UV-Vis) spectroscopy was used to monitor the kinetics of formation of the products of the aldol condensation reaction of a range of aliphatic aldehydes (C2-C8) The experiments were carried out at various sulfuric acid concentrations and a range of temperatures in order to estimate the rate constants of such reactions on sulfuric acid aerosols under tropospheric conditions. The rate constants were generally found to decrease as the chain length of the aliphatic aldehyde increased (except for acetaldehyde, which had an unusually small rate constant), increase as a function of sulfuric acid concentration as predicted by excess acidity theory, and showed normal Arrhenius behavior as a function of temperature.

  13. Halides with Fifteen Aliphatic C–H···Anion Interaction Sites

    PubMed Central

    Shi, Genggongwo; Aliakbar Tehrani, Zahra; Kim, Dongwook; Cho, Woo Jong; Youn, Il-Seung; Lee, Han Myoung; Yousuf, Muhammad; Ahmed, Nisar; Shirinfar, Bahareh; Teator, Aaron J.; Lastovickova, Dominika N.; Rasheed, Lubna; Lah, Myoung Soo; Bielawski, Christopher W.; Kim, Kwang S.

    2016-01-01

    Since the aliphatic C–H···anion interaction is relatively weak, anion binding using hydrophobic aliphatic C–H (Cali–H) groups has generally been considered not possible without the presence of additional binding sites that contain stronger interactions to the anion. Herein, we report X-ray structures of organic crystals that feature a chloride anion bound exclusively by hydrophobic Cali–H groups. An X-ray structure of imidazolium-based scaffolds using Cali–H···A− interactions (A− = anion) shows that a halide anion is directly interacting with fifteen Cali–H groups (involving eleven hydrogen bonds, two bidentate hydrogen-bond-type binding interactions and two weakly hydrogen-bonding-like binding interactions). Additional supporting interactions and/or other binding sites are not observed. We note that such types of complexes may not be rare since such high numbers of binding sites for an anion are also found in analogous tetraalkylammonium complexes. The Cali–H···A− interactions are driven by the formation of a near-spherical dipole layer shell structure around the anion. The alternating layers of electrostatic charge around the anion arise because the repulsions between weakly positively charged H atoms are reduced by the presence of the weakly negatively charged C atoms connected to H atoms. PMID:27444513

  14. Chiroptical study of α-aliphatic amino acid films in the vacuum ultraviolet region.

    PubMed

    Tanaka, Masahito; Yagi-Watanabe, Kazutoshi; Kaneko, Fusae; Nakagawa, Kazumichi

    2010-11-11

    A series of natural circular dichroism (CD) and absorption spectra for films of α-aliphatic amino acids--such as alanine, aminobutyric acid, norvaline, norleucine, valine, leucine, and isoleucine--in the vacuum ultraviolet (VUV) region were observed with the absolute values of optical constants at the undulator-based CD beamline TERAS BL5. Preliminary predictions of some CD spectra were also performed, based on quantum-chemical calculations using the crystal structure. Although the absorption spectra show similar features to each other, significant differences between the CD spectra were found, especially in the 7-8 eV region. The CD spectra of aliphatic amino acids with branched alkyl groups in the side-chain--such as valine, leucine, and isoleucine--exhibit strong negative CD peaks in this energy region. In contrast, the corresponding CD peaks were weak or absent in the spectra of amino acids with straight alkyl groups. Our simple calculation, and the absorption spectra of alkanes, suggest that this difference partly originates from the contribution of the alkyl group. Clear discrepancies between the CD spectra of these amino acids in solutions and those in the solid state were also observed; this is probably caused by the different molecular structures in each state. Our results clearly indicated that CD spectra in the VUV region were very sensitive to the conformations of chiral molecules. PMID:20958008

  15. Competitive Oxidation and Reduction of Aliphatic Alcohols over (WO3)3 Clusters

    SciTech Connect

    Kim, Yu K.; Dohnalek, Zdenek; Kay, Bruce D.; Rousseau, Roger J.

    2009-06-04

    The reactions of C1 to C4 aliphatic alcohols over (WO3)3 clusters were studied experimentally and theoretically using temperature-programmed desorption, infrared reflection-absorption spectroscopy and density functional theory. The results reveal that all C1 to C4 aliphatic alcohols readily react with (WO3)3 clusters by heterolytic cleavage of the RO-H bond to give alkoxy (RO ) bound to W(VI) centers and a proton (H+) attached to the terminal oxygen atom of a tungstyl group (W=O). Two protons adsorbed onto the cluster readily react with the doubly-bonded oxygen to from a water molecule that desorbs at 200-300 K and the alkoxy that undergoes decomposition at higher temperatures into the corresponding alkene, aldehyde, and/or ether. Our theory predicts that all three channels proceed over the W(VI) Lewis acid site with energy barriers of 30-40 kcal/mol, where dehydration is favored over the others. We also present further analysis of the yield and reaction temperature as a function of the alkyl substituents and discuss the origin of the reaction selectivity among the three reaction channels.

  16. The Amyloid-β-SDR5C1(ABAD) Interaction Does Not Mediate a Specific Inhibition of Mitochondrial RNase P

    PubMed Central

    Vilardo, Elisa; Rossmanith, Walter

    2013-01-01

    The amyloid-β peptide (Aβ) is suggested to cause mitochondrial dysfunction in Alzheimer’s disease. The mitochondrial dehydrogenase SDR5C1 (also known as ABAD) was shown to bind Aβ and was proposed to thereby mediate mitochondrial toxicity, but the molecular mechanism has not been clarified. We recently identified SDR5C1 as an essential component of human mitochondrial RNase P and its associated tRNA:m1R9 methyltransferase, the enzymes responsible for tRNA 5′-end processing and methylation of purines at tRNA position 9, respectively. With this work we investigated whether SDR5C1’s role as a subunit of these two tRNA-maturation activities represents the mechanistic link between Aβ and mitochondrial dysfunction. Using recombinant enzyme components, we tested RNase P and methyltransferase activity upon titration of Aβ. Micromolar concentrations of monomeric or oligomerized Aβ were required to inhibit tRNA 5′-end processing and position 9 methylation catalyzed by the SDR5C1-containing enzymes, yet similar concentrations of Aβ also inhibited related RNase P and methyltransferase activities, which do not contain an SDR5C1 homolog. In conclusion, the proposed deleterious effect of Aβ on mitochondrial function cannot be explained by a specific inhibition of mitochondrial RNase P or its tRNA:m1R9 methyltransferase subcomplex, and the molecular mechanism of SDR5C1-mediated Aβ toxicity remains unclear. PMID:23755257

  17. Preparation of monomeric (Me[sub 5]C[sub 5])[sub 2]VO and (Me[sub 5]C[sub 5])[sub 2]Ti(O)(L) and their decomposition to (Me[sub 5]C[sub 5])[sub 4]M[sub 4]([mu]-O)[sub 6

    SciTech Connect

    Smith, M.R. III; Matsunaga, P.T.; Andersen, R.A. )

    1993-07-28

    Nitrous oxide is a convenient source of oxygen atoms for the synthesis of oxometallocenes (and the products derived there from) as well as for the insertion of oxygen into metal-hydrogen or -carbon bonds. In this communication we show that (Me[sub 5]C[sub 5])[sub 2]VO and (Me[sub 5]C[sub 5])[sub 2]-Ti(O)(L), where L is pyridine or a substituted pyridine, can be isolated in reactions between nitrous oxide and the metallocenes and that they decompose to the known tetranuclear materials (Me[sub 5]C[sub 5])[sub 4]V[sub 4]([mu]-O)[sub 6] and (Me[sub 5]C[sub 5])[sub 4]([mu]-O)[sub 6]. 18 refs., 2 figs.

  18. Direct β-C(sp(3))-H Functionalization of Aliphatic Amines to α,β-Unsaturated Imines, Aldehydes, and Chromenes.

    PubMed

    Mandal, Sumana; Mahato, Sujit; Jana, Chandan K

    2015-08-01

    A metal-free method for direct β-C(sp(3))-H functionalization of aliphatic amine was developed. The method is based on a reaction that yields enamine directly from the corresponding aliphatic amine, which otherwise requires the aid of metallic reagent and/or external oxidant. The reaction is operationally simple, general, and highly efficient in functionalizing both cyclic and acyclic amines. Structurally diverse unsaturated imines were obtained from N-heterocycles, while acyclic amines provided 2-alkyl cinnamaldehyde and benzopyran derivatives with excellent E/Z-selectivity. PMID:26204435

  19. Synthesis and biological evaluation of novel aliphatic amido-quaternary ammonium salts for anticancer chemotherapy: part II.

    PubMed

    Yang, Jee Sun; Song, Doona; Ko, Won Jin; Kim, Bunyea; Kim, Bo-Kyung; Park, Song-Kyu; Won, Misun; Lee, Kiho; Lee, Kyeong; Kim, Hwan Mook; Han, Gyoonhee

    2013-05-01

    A series of novel aliphatic amido-quaternary ammonium salts were synthesized and evaluated for their anticancer effects involving induction of RhoB. Most of these compounds, featuring open-ring forms of aliphatic amido-quaternary ammonium salts, exhibited potent anti-proliferative activities in human cancer cell lines, including PC-3, NUGC-3, MDA-MB-231, ACHN, HCT-15, and NCI-H23. In further evaluation, the representative compound N,N-diethyl-N-(2-(N-methyltetradecanamido)ethyl)prop-2-en-1-aminium bromide (3b) exhibited potent pro-apoptotic activity, through RhoB activation, in HeLa cells. PMID:23567950

  20. Complete genome of Zhongshania aliphaticivorans SM-2(T), an aliphatic hydrocarbon-degrading bacterium isolated from tidal flat sediment.

    PubMed

    Jia, Baolei; Jeong, Hye Im; Kim, Kyung Hyun; Jeon, Che Ok

    2016-05-20

    Zhongshania aliphaticivorans SM-2(T), a degrader of aliphatic hydrocarbons, is a Gram-negative, rod-shaped, flagellated, facultatively aerobic bacterium. Here, we report the genome sequence of strain SM-2(T), which has a size of 4,204,359bp with 44 tRNAs, 9 rRNAs, and 3664 protein-coding genes. In addition, several genes encoding aliphatic hydrocarbon degraders (alkane 1-monooxygenase, haloalkane dehalogenase, and cytochrome P450) were detected in the genome shedding light on the function of pollutants degradation. PMID:27034022